CN118475549A - Compound, organic electroluminescent element, and electronic device - Google Patents

Abstract

A compound represented by the following general formulA (1C-A).In the general formulA (1C-A), 1 of R ₄～R₈ and R ₁₀～R₁₂ is A group represented by the general formulA (1D-A), R ₁～R₃、R₉ and R ₄～R₈ and R ₁₀～R₁₂ are hydrogen atoms or substituents, etc., at least one of R ₂₁～R₃₀ is A group other than A hydrogen atom, in the case where R ₁₁ is A group represented by the general formulA (1D), R ₁₂ is A hydrogen atom or phenyl, in the case where R ₁₂ is A group represented by the general formulA (1D), R ₁₁ is A hydrogen atom or phenyl, in the general formulA (1D), 1 of R ₂₁～R₃₀ represents A bonding position to A benzo [ A ] anthracycline in the general formulA (1C), and in the case where R ₂₁～R₃₀ in the general formulA (1D) which does not form A ring is A hydrogen atom or A substituent, etc.

Description

Compound, organic electroluminescent element and electronic device

Technical Field

The invention relates to a compound, an organic electroluminescent element and an electronic device.

Background Art

Organic electroluminescent elements (hereinafter sometimes referred to as "organic EL elements") are used in full-color displays such as mobile phones and televisions. When voltage is applied to an organic EL element, holes are injected from the anode into the light-emitting layer, and electrons are injected from the cathode into the light-emitting layer. Then, in the light-emitting layer, the injected holes and electrons recombine to form excitons. At this time, according to the statistical law of electron spin, singlet excitons are generated at a ratio of 25%, and triplet excitons are generated at a ratio of 75%.

In order to improve the performance of organic EL elements, various studies have been conducted on compounds used in organic EL elements (see, for example, Patent Documents 1 and 2). Examples of the performance of organic EL elements include brightness, emission wavelength, chromaticity, luminous efficiency, driving voltage, and lifespan.

Prior art literature

Patent Literature

Patent Document 1: International Publication No. 2021/132535

Patent Document 2: International Publication No. 2009/081774

Summary of the invention

Problem that the invention aims to solve

One of the objects of the present invention is to provide a compound capable of improving the life of an organic electroluminescent element, an organic electroluminescent element comprising the compound, and an electronic device equipped with the organic electroluminescent element.

Another object of the present invention is to provide an organic electroluminescent element having an improved lifespan and an electronic device equipped with the organic electroluminescent element.

Means used to solve problems

According to one embodiment of the present invention, a compound represented by the following general formula (1C-A) is provided.

【Chemical formula 1】

(In the above general formula (1C-A),

One of R ₄ to R ₈ and R ₁₀ to R ₁₂ is a group represented by the above general formula (1D-A),

R ₁ to R ₃ , R ₉ , and R ₄ to R ₈ and R ₁₀ to R ₁₂ other than the group represented by the above general formula (1D-A) are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C(=O)R ₈₀₁ ,

-COOR ₈₀₂ ,

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

When R ₁₁ is a group represented by the above general formula (1D-A), R ₁₂ is a hydrogen atom or a substituted or unsubstituted phenyl group,

When R ₁₂ is a group represented by the above general formula (1D-A), R ₁₁ is a hydrogen atom or a substituted or unsubstituted phenyl group,

In the above general formula (1D-A), one of R ₂₁ to R ₃₀ represents a bonding position to the benz[a]anthracene ring in the above general formula (1C-A), and one or more groups of two or more adjacent R ₂₁ to R ₃₀ in the above general formula (1D-A) that are not the bonding position are included.

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R 21 to R 30 in the above general formula (1D-A) that are not bonded to the benz[a]anthracene ring in the above general formula (1C-A), do not form the above substituted or unsubstituted monocyclic ring, and do not form the above _substituted or _{unsubstituted} condensed ring are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁₎ (R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

wherein at least one of R ₂₁ to R ₃₀ is a group other than a hydrogen atom,

In the compound represented by the above general formula (1C-A), R ₉₀₁ , R ₉₀₂ , R ₉₀₃ , R ₉₀₄ , R ₉₀₅ , R ₉₀₆ , R ₉₀₇ , R ₈₀₁ and R ₈₀₂ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

When there are a plurality of R ₉₀₁ , the plurality of R ₉₀₁ are the same as or different from each other.

When there are multiple R ₉₀₂ , the multiple R ₉₀₂ are the same as or different from each other.

When there are multiple R ₉₀₃ , the multiple R ₉₀₃ are the same as or different from each other.

When there are a plurality of R ₉₀₄ , the plurality of R ₉₀₄ are the same as or different from each other.

When there are multiple R ₉₀₅ , the multiple R ₉₀₅ are the same as or different from each other.

When there are multiple R ₉₀₆ , the multiple R ₉₀₆ are the same as or different from each other.

When there are a plurality of R ₉₀₇ , the plurality of R ₉₀₇ are the same as or different from each other.

When there are multiple _R801 , the multiple _R801 are the same as or different from each other.

When there are multiple R ₈₀₂ , the multiple R ₈₀₂ are the same as or different from each other.)

According to one embodiment of the present invention, a compound represented by the following general formula (1C-B) is provided.

【Chemical formula 2】

(In the above general formula (1C-B),

One of R ₄ to R ₆ , R ₈ and R ₁₀ to R ₁₂ is a group represented by the above general formula (1D-B),

R ₁ to R ₃ , R ₇ , R ₉ , and R ₄ to R ₆ , R ₈ and R ₁₀ to R ₁₂ other than the group represented by the above general formula (1D-B) are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C(=O)R ₈₀₁ ,

-COOR ₈₀₂ ,

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

When R ₁₁ is a group represented by the above general formula (1D-B), R ₁₂ is a hydrogen atom or an unsubstituted phenyl group,

When R ₁₂ is a group represented by the above general formula (1D-B), R ₁₁ is a substituted or unsubstituted phenyl group,

In the above general formula (1D-B), one of R ₂₁ to R ₃₀ represents a bonding position to the benz[a]anthracene ring in the above general formula (1C-B), and one or more groups of two or more adjacent R ₂₁ to R ₃₀ in the above general formula (1D-B) that are not the bonding position are included.

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R 21 to R 30 in the above general formula (1D-B) that are not bonded to the benz[a]anthracene ring in the above general formula (1C-B), do not form the above substituted or unsubstituted monocyclic ring, and do not form the above _substituted or _{unsubstituted} condensed ring are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

In the compound represented by the above general formula (1C-B), R ₉₀₁ , R ₉₀₂ , R ₉₀₃ , R ₉₀₄ , R ₉₀₅ , R ₉₀₆ , R ₉₀₇ , R ₈₀₁ and R ₈₀₂ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

When there are a plurality of R ₉₀₁ , the plurality of R ₉₀₁ are the same as or different from each other.

When there are multiple R ₉₀₂ , the multiple R ₉₀₂ are the same as or different from each other.

When there are multiple R ₉₀₃ , the multiple R ₉₀₃ are the same as or different from each other.

When there are a plurality of R ₉₀₄ , the plurality of R ₉₀₄ are the same as or different from each other.

When there are multiple R ₉₀₅ , the multiple R ₉₀₅ are the same as or different from each other.

When there are multiple R ₉₀₆ , the multiple R ₉₀₆ are the same as or different from each other.

When there are a plurality of R ₉₀₇ , the plurality of R ₉₀₇ are the same as or different from each other.

When there are multiple _R801 , the multiple _R801 are the same as or different from each other.

When there are multiple R ₈₀₂ , the multiple R ₈₀₂ are the same as or different from each other.)

According to one embodiment of the present invention, a compound represented by the following general formula (1C-C) is provided.

【Chemical formula 3】

(In the above general formula (1C-C),

One of R ₄ to R ₈ and R ₁₀ to R ₁₂ is a group represented by the above general formula (1D-C),

R ₁ to R ₃ , R ₉ , and R ₄ to R ₈ and R ₁₀ to R ₁₂ other than the group represented by the above general formula (1D-C) are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C(=O)R ₈₀₁ ,

-COOR ₈₀₂ ,

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

When R ₁₁ is a group represented by the above general formula (1D-C), R ₁₂ is a hydrogen atom or a substituted or unsubstituted phenyl group,

When R ₁₂ is a group represented by the above general formula (1D-C), R ₁₁ is a hydrogen atom or a substituted or unsubstituted phenyl group,

In the above general formula (1D-C), one of R ₂₂ , R ₂₃ , R ₂₅ , R ₂₇ , R ₂₈ and R ₃₀ represents a bonding position to the benzo[a]anthracene ring in the above general formula (1C-C), and one or more of the group consisting of R ₂₁ , R ₂₄ , R ₂₆ and R ₂₉ , and two or more adjacent ones of R ₂₂ , R ₂₃ , R ₂₅ , R ₂₇ , R ₂₈ and R ₃₀ in the above general formula (1D-C) that are not the bonding position.

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R 21 to R 30 in the above general formula (1D-C) that are not bonded to the benz[a]anthracene ring in the above general formula (1C-C), that do not form the above substituted or unsubstituted monocyclic ring, and that do not form the above _substituted or _{unsubstituted} condensed ring are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

In the compound represented by the above general formula (1C-C), R ₉₀₁ , R ₉₀₂ , R ₉₀₃ , R ₉₀₄ , R ₉₀₅ , R ₉₀₆ , R ₉₀₇ , R ₈₀₁ and R ₈₀₂ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

When there are a plurality of R ₉₀₁ , the plurality of R ₉₀₁ are the same as or different from each other.

When there are multiple R ₉₀₂ , the multiple R ₉₀₂ are the same as or different from each other.

When there are multiple R ₉₀₃ , the multiple R ₉₀₃ are the same as or different from each other.

When there are a plurality of R ₉₀₄ , the plurality of R ₉₀₄ are the same as or different from each other.

When there are multiple R ₉₀₅ , the multiple R ₉₀₅ are the same as or different from each other.

When there are multiple R ₉₀₆ , the multiple R ₉₀₆ are the same as or different from each other.

When there are a plurality of R ₉₀₇ , the plurality of R ₉₀₇ are the same as or different from each other.

When there are multiple _R801 , the multiple _R801 are the same as or different from each other.

When there are multiple R ₈₀₂ , the multiple R ₈₀₂ are the same as or different from each other.)

According to one embodiment of the present invention, there is provided an organic electroluminescent device comprising the compound according to one embodiment of the present invention.

According to one embodiment of the present invention, there is provided an organic electroluminescent element comprising an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein at least one of the organic layers contains the compound according to one embodiment of the present invention.

According to one embodiment of the present invention, an organic electroluminescent element is provided, which comprises an anode, a cathode and an organic layer arranged between the anode and the cathode, wherein the organic layer has a light-emitting region, the light-emitting region comprises a first light-emitting layer and a second light-emitting layer, the first light-emitting layer comprises a first compound represented by the following general formula (1C), and the second light-emitting layer comprises a second compound.

【Chemical formula 4】

(In the above general formula (1C),

One of R ₄ to R ₈ and R ₁₀ to R ₁₂ is a group represented by the above general formula (1D),

R ₁ to R ₃ , R ₉ , and R ₄ to R ₈ and R ₁₀ to R ₁₂ other than the group represented by the above general formula (1D) are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C(=O)R ₈₀₁ ,

-COOR ₈₀₂ ,

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

When R ₁₁ is a group represented by the above general formula (1D), R ₁₂ is a hydrogen atom or a substituted or unsubstituted phenyl group,

When R ₁₂ is a group represented by the above general formula (1D), R ₁₁ is a hydrogen atom or a substituted or unsubstituted phenyl group,

In the above general formula (1D), one of R ₂₁ to R ₃₀ represents a bonding position to the benz[a]anthracene ring in the above general formula (1C), and one or more groups consisting of two or more adjacent ones of R ₂₁ to R ₃₀ in the above general formula (1D) that are not the bonding position are present.

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₂₁ to R 30 in the above general formula (1D) which are not bonded to the benz[a]anthracene ring in the above general formula (1C), do not form the above substituted or unsubstituted monocyclic ring, and do not form the above substituted or _{unsubstituted} condensed ring, are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

In the compound represented by the above general formula (1C), R ₉₀₁ , R ₉₀₂ , R ₉₀₃ , R ₉₀₄ , R ₉₀₅ , R ₉₀₆ , R ₉₀₇ , R ₈₀₁ and R ₈₀₂ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

When there are a plurality of R ₉₀₁ , the plurality of R ₉₀₁ are the same as or different from each other.

When there are multiple R ₉₀₂ , the multiple R ₉₀₂ are the same as or different from each other.

When there are multiple R ₉₀₃ , the multiple R ₉₀₃ are the same as or different from each other.

When there are a plurality of R ₉₀₄ , the plurality of R ₉₀₄ are the same as or different from each other.

When there are multiple R ₉₀₅ , the multiple R ₉₀₅ are the same as or different from each other.

When there are multiple R ₉₀₆ , the multiple R ₉₀₆ are the same as or different from each other.

When there are a plurality of R ₉₀₇ , the plurality of R ₉₀₇ are the same as or different from each other.

When there are multiple _R801 , the multiple _R801 are the same as or different from each other.

When there are multiple R ₈₀₂ , the multiple R ₈₀₂ are the same as or different from each other.)

According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescent element according to one aspect of the present invention.

According to one aspect of the present invention, there can be provided a compound capable of improving the life of an organic electroluminescent element, an organic electroluminescent element including the compound, and an electronic device equipped with the organic electroluminescent element.

According to one aspect of the present invention, an organic electroluminescent element having an improved life and an electronic device equipped with the organic electroluminescent element can be provided.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 is a diagram showing a schematic configuration of an example of an organic electroluminescent element according to an embodiment of the present invention.

FIG. 2 is a diagram showing a schematic configuration of another example of an organic electroluminescent element according to an embodiment of the present invention.

DETAILED DESCRIPTION

[definition]

In this specification, the hydrogen atom is meant to include isotopes having different numbers of neutrons, namely, protium, deuterium, and tritium.

In the present specification, in chemical structural formulas, a bondable position that does not clearly show a symbol such as "R" or "D" representing a deuterium atom is assumed to be bonded with a hydrogen atom, that is, a protium atom, a deuterium atom, or a tritium atom.

In this specification, the number of ring carbons refers to the number of carbon atoms among the atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a condensed ring compound, a bridged ring compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are bonded in a ring shape. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring carbons. The "number of ring carbons" recorded below is set in the same manner unless otherwise stated. For example, the number of ring carbons of a benzene ring is 6, the number of ring carbons of a naphthalene ring is 10, the number of ring carbons of a pyridine ring is 5, and the number of ring carbons of a furan ring is 4. In addition, for example, the number of ring carbons of 9,9-diphenylfluorenyl is 13, and the number of ring carbons of 9,9'-spirobifluorenyl is 25.

In addition, when a substituent such as an alkyl group is substituted on a benzene ring, the carbon number of the alkyl group is not included in the ring carbon number of the benzene ring. Therefore, the ring carbon number of the benzene ring substituted with an alkyl group is 6. In addition, when a substituent such as an alkyl group is substituted on a naphthalene ring, the carbon number of the alkyl group is not included in the ring carbon number of the naphthalene ring. Therefore, the ring carbon number of the naphthalene ring substituted with an alkyl group is 10.

In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a condensed ring compound, a bridged ring compound, a carbocyclic compound, and a heterocyclic compound) in which atoms are cyclically bonded. Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate the bonds of atoms constituting the ring) and atoms contained in a substituent when the ring is substituted by a substituent are not included in the number of ring atoms. The "number of ring atoms" recorded below is set in the same manner as long as it is not recorded separately. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms bonded to a pyridine ring or atoms constituting a substituent is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring bonded with a hydrogen atom or a substituent is 6. In addition, for example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring atoms of the quinazoline ring. Therefore, the number of ring atoms of the quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

In this specification, "carbon number XX to YY" in the expression "substituted or unsubstituted ZZ group with carbon number XX to YY" means the carbon number of the ZZ group when it is unsubstituted, and does not include the carbon number of the substituent when it is substituted. Here, "YY" is greater than "XX", "XX" means an integer greater than 1, and "YY" means an integer greater than 2.

In this specification, "the number of atoms XX to YY" in the expression "a substituted or unsubstituted ZZ group having an atomic number of XX to YY" means the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of the substituent when substituted. Here, "YY" is greater than "XX", "XX" means an integer greater than 1, and "YY" means an integer greater than 2.

In the present specification, an unsubstituted ZZ group means a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group means a case where a "substituted or unsubstituted ZZ group" is a "substituted ZZ group".

In the present specification, "unsubstituted" in the expression "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group is not replaced by a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom or a tritium atom.

In addition, in the present specification, "substituted" when expressing "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced by a substituent. "Substituted" when expressing "BB group substituted by AA group" also means that one or more hydrogen atoms in the BB group are replaced by an AA group.

"Substituents described in this specification"

The substituents described in the present specification are described below.

The number of ring carbon atoms of the "unsubstituted aryl group" described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise described in the present specification.

The number of ring atoms of the "unsubstituted heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise described in the present specification.

The carbon number of the "unsubstituted alkyl group" described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise described in the present specification.

The carbon number of the "unsubstituted alkenyl group" described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise described in the present specification.

The number of carbon atoms in the "unsubstituted alkynyl group" described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise described in the present specification.

The number of ring carbon atoms of the "unsubstituted cycloalkyl group" described in the present specification is 3 to 50, preferably 3 to 20, and more preferably 3 to 6, unless otherwise described in the present specification.

The number of ring carbon atoms of the "unsubstituted arylene group" described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise described in the present specification.

The number of ring atoms of the "unsubstituted divalent heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise described in the present specification.

The carbon number of the "unsubstituted alkylene group" described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise described in the present specification.

"Substituted or unsubstituted aryl"

As specific examples of "substituted or unsubstituted aryl" described in this specification (specific example group G1), the following unsubstituted aryl (specific example group G1A) and substituted aryl (specific example group G1B) can be cited. (Here, unsubstituted aryl refers to the case where "substituted or unsubstituted aryl" is "unsubstituted aryl", and substituted aryl refers to the case where "substituted or unsubstituted aryl" is "substituted aryl".) In this specification, when only "aryl" is expressed, both "unsubstituted aryl" and "substituted aryl" are included.

"Substituted aryl" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl" are replaced by a substituent. Examples of "substituted aryl" include groups in which one or more hydrogen atoms of an "unsubstituted aryl" are replaced by a substituent in the following specific example group G1A, and examples of substituted aryl in the following specific example group G1B. It should be noted that the examples of "unsubstituted aryl" and "substituted aryl" listed here are only examples, and the "substituted aryl" described in this specification also includes groups in which the hydrogen atom bonded to the carbon atom of the aryl itself in the "substituted aryl" in the following specific example group G1B is further replaced by a substituent, and groups in which the hydrogen atom of the substituent in the "substituted aryl" in the following specific example group G1B is further replaced by a substituent.

Unsubstituted aryl (specific example group G1A):

Phenyl,

p-Biphenyl,

m-Biphenyl,

o-Biphenyl,

4-terphenyl-4-yl,

4-terphenyl-3-yl,

4-terphenyl-2-yl,

4-terphenyl-1,

m-terphenyl-3-yl,

m-terphenyl-2-yl,

o-terphenyl-4-yl,

o-terphenyl-3-yl,

o-terphenyl-2-yl,

1-naphthyl,

2-naphthyl,

Anthracene,

Benzanthryl,

Fiki,

Triphenylene,

Phenyl,

Pyrene

base,

Benzo base,

Triphenylene,

Benzotriphenylene,

Tetraphenylene,

Pentaphenyl,

Fluorene,

9,9'-spirobifluorenyl,

Benzofluorenyl,

Dibenzofluorenyl,

Fluoranthene,

Benzofluoranthene,

Perylene and

A monovalent aromatic group derived by removing one hydrogen atom from the ring structure represented by the following general formula (TEMP-1) to (TEMP-15).

【Chemical formula 5】

【Chemical formula 6】

Substituted aryl (specific example group G1B):

o-Toluyl,

m-Toluene

p-Tolyl,

p-Xylyl,

m-Xylyl,

o-Xylyl,

p-Isopropylphenyl,

m-isopropylphenyl,

o-isopropylphenyl,

4-tert-Butylphenyl,

m-tert-butylphenyl,

o-tert-butylphenyl,

3,4,5-Trimethylphenyl,

9,9-dimethylfluorenyl,

9,9-diphenylfluorenyl,

9,9-bis(4-methylphenyl)fluorenyl,

9,9-bis(4-isopropylphenyl)fluorenyl,

9,9-bis(4-tert-butylphenyl)fluorenyl,

Cyanophenyl,

Triphenylsilylphenyl,

Trimethylsilylphenyl,

Phenyl naphthyl,

Naphthylphenyl and

A group in which one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the above general formulae (TEMP-1) to (TEMP-15) are replaced with a substituent.

"Substituted or unsubstituted heterocyclic group"

The "heterocyclic group" described in the present specification is a cyclic group containing at least one heteroatom among the ring-forming atoms. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom and a boron atom.

The "heterocyclic group" described in the present specification is a monocyclic group or a condensed ring group.

The "heterocyclic group" described in the present specification is an aromatic heterocyclic group or a non-aromatic heterocyclic group.

As specific examples of the "substituted or unsubstituted heterocyclic group" described in the present specification (specific example group G2), the following unsubstituted heterocyclic groups (specific example group G2A) and substituted heterocyclic groups (specific example group G2B) can be cited. (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In the present specification, when only "heterocyclic group" is expressed, both "unsubstituted heterocyclic group" and "substituted heterocyclic group" are included.

"Substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced by a substituent. Specific examples of "substituted heterocyclic group" include groups in which hydrogen atoms of the "unsubstituted heterocyclic group" of the following specific example group G2A are substituted, and examples of substituted heterocyclic groups of the following specific example group G2B are mentioned. It should be noted that the examples of "unsubstituted heterocyclic group" and "substituted heterocyclic group" listed here are only examples, and the "substituted heterocyclic group" recorded in this specification also includes groups in which hydrogen atoms bonded to ring atoms of the heterocyclic group itself in the "substituted heterocyclic group" of the specific example group G2B are further replaced by substituents, and groups in which hydrogen atoms of substituents in the "substituted heterocyclic group" of the specific example group G2B are further replaced by substituents.

Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing nitrogen atoms (specific example group G2A1), unsubstituted heterocyclic groups containing oxygen atoms (specific example group G2A2), unsubstituted heterocyclic groups containing sulfur atoms (specific example group G2A3), and monovalent heterocyclic groups derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4).

Specific example group G2B includes, for example, the following heterocyclic groups containing nitrogen atom substitution (specific example group G2B1), oxygen atom substitution (specific example group G2B2), sulfur atom substitution (specific example group G2B3), and a group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from a ring structure represented by the following general formula (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4).

Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1):

Pyrrolyl,

Imidazole,

Pyrazolyl,

triazolyl, tetrazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, isoindolyl, indolizinyl, quinolizinyl, quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, benzimidazolyl, indazolyl, phenanthrolinyl, phenanthridinyl, acridinyl, phenazinyl, carbazolyl,

Benzocarbazolyl,

Morpholinyl,

Phenoxazine,

Phenothiazine,

Azacarbazolyl, and

Diazacarbazolyl.

Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2):

Furanyl,

Oxazolyl,

Isoxazolyl,

Oxadiazolyl,

Cuckoo ton base,

Benzofuranyl,

Isobenzofuranyl,

Dibenzofuranyl,

Naphthobenzofuranyl,

Benzoxazolyl,

Benzisoxazolyl,

Phenoxazine,

Morpholinyl,

dinaphthofuranyl,

Azadibenzofuranyl,

Diazadibenzofuranyl,

Azanaphthobenzofuranyl and

Diazinobenzofuranyl.

Unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3):

Thienyl,

Thiazolyl,

Isothiazolyl,

Thiadiazole,

benzothienyl,

Isobenzothienyl,

dibenzothienyl,

naphthobenzothienyl,

Benzothiazolyl,

Benzisothiazolyl,

Phenothiazine,

dinaphthothienyl,

azadibenzothienyl,

diazadibenzothienyl,

azanaphthobenzothienyl and

diazanaphthobenzothienyl.

A monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure represented by the following general formula (TEMP-16) to (TEMP-33) (Specific example group G2A4):

【Chemical formula 7】

【Chemical formula 8】

In the above general formulae (TEMP-16) to (TEMP-33), _XA and _YA are each independently an oxygen atom, a sulfur atom, NH or CH ₂ , wherein at least one of _XA and _YA is an oxygen atom, a sulfur atom or NH.

In the above general formulas (TEMP-16) to (TEMP-33), when at least one of _XA and _YA is NH or CH2, the monovalent heterocyclic group derived from the ring structure represented by the above general formulas (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from these NH or CH2.

Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1):

(9-phenyl)carbazolyl,

(9-biphenyl)carbazolyl,

(9-phenyl)phenylcarbazolyl,

(9-naphthyl)carbazolyl,

Diphenylcarbazole-9-yl,

Phenylcarbazol-9-yl,

Methylbenzimidazolyl,

Ethylbenzimidazolyl,

Phenyl triazine,

Biphenyl triazine,

Diphenyltriazine,

Phenylquinazolinyl, and

Biphenylquinazolinyl.

Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):

Phenyldibenzofuranyl,

Methyldibenzofuranyl,

tert-Butyldibenzofuranyl and

The monovalent residue of spiro[9H-xanthen-9,9'-[9H]fluorene].

Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):

Phenyldibenzothiophene,

Methyldibenzothiophene,

tert-Butyldibenzothienyl and

The monovalent residue of spiro[9H-thioxanthen-9,9'-[9H]fluorene].

· Groups in which one or more hydrogen atoms of the monovalent heterocyclic group derived from the ring structure represented by the above general formulae (TEMP-16) to (TEMP-33) are replaced with substituents (Specific example group G2B4):

The above-mentioned “one or more hydrogen atoms of the monovalent heterocyclic group” means one or more hydrogen atoms selected from the group consisting of hydrogen atoms bonded to ring-constituting carbon atoms of the monovalent heterocyclic group, hydrogen atoms bonded to nitrogen atoms when at least one of _XA and _YA is NH, and hydrogen atoms of a methylene group when one of _XA and _YA is _CH2 .

"Substituted or unsubstituted alkyl"

As specific examples of "substituted or unsubstituted alkyl" described in this specification (specific example group G3), the following unsubstituted alkyl (specific example group G3A) and substituted alkyl (specific example group G3B) can be cited. (Here, unsubstituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl refers to the case where "substituted or unsubstituted alkyl" is "substituted alkyl".) Hereinafter, when only "alkyl" is expressed, both "unsubstituted alkyl" and "substituted alkyl" are included.

"Substituted alkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkyl" are replaced by a substituent. Specific examples of "substituted alkyl" include groups in which one or more hydrogen atoms in the following "unsubstituted alkyl" (specific example group G3A) are replaced by a substituent, and examples of substituted alkyl (specific example group G3B) can be cited. In the present specification, the alkyl group in "unsubstituted alkyl" refers to a chain alkyl group. Therefore, "unsubstituted alkyl" includes "unsubstituted alkyl" as a straight chain and "unsubstituted alkyl" as a branched chain. It should be noted that the examples of "unsubstituted alkyl" and "substituted alkyl" listed here are only examples, and the "substituted alkyl" recorded in the present specification also includes groups in which the hydrogen atoms of the alkyl group itself in the "substituted alkyl" of the specific example group G3B are further replaced by a substituent, and groups in which the hydrogen atoms of the substituent in the "substituted alkyl" of the specific example group G3B are further replaced by a substituent.

Unsubstituted alkyl (specific example group G3A):

methyl,

Ethyl,

n-propyl,

Isopropyl,

n-Butyl,

Isobutyl,

sec-butyl and

Tert-butyl.

Substituted alkyl (specific example group G3B):

Heptafluoropropyl (including isomers),

Pentafluoroethyl,

2,2,2-Trifluoroethyl and

Trifluoromethyl.

"Substituted or unsubstituted alkenyl"

As specific examples of "substituted or unsubstituted alkenyl" described in this specification (specific example group G4), the following unsubstituted alkenyl (specific example group G4A) and substituted alkenyl (specific example group G4B) can be cited. (Here, unsubstituted alkenyl refers to the case where "substituted or unsubstituted alkenyl" is "unsubstituted alkenyl", and "substituted alkenyl" refers to the case where "substituted or unsubstituted alkenyl" is "substituted alkenyl".) In this specification, when simply expressed as "alkenyl", both "unsubstituted alkenyl" and "substituted alkenyl" are included.

"Substituted alkenyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl" are replaced by a substituent. Specific examples of "substituted alkenyl" include the following "unsubstituted alkenyl" (specific example group G4A) groups with substituents and examples of substituted alkenyl (specific example group G4B). It should be noted that the examples of "unsubstituted alkenyl" and "substituted alkenyl" listed here are only examples, and the "substituted alkenyl" recorded in this specification also includes groups in which the hydrogen atoms of the alkenyl itself in the "substituted alkenyl" of the specific example group G4B are further replaced by a substituent and groups in which the hydrogen atoms of the substituent in the "substituted alkenyl" of the specific example group G4B are further replaced by a substituent.

Unsubstituted alkenyl (specific example Group G4A):

Vinyl,

Allyl,

1-Butenyl,

2-Butenyl and

3-Butenyl.

Substituted alkenyl (specific example group G4B):

1,3-Butadienyl,

1-Methylvinyl,

1-methylallyl,

1,1-dimethylallyl,

2-Methylallyl and

1,2-Dimethylallyl.

As specific examples of "substituted or unsubstituted alkynyl" described in this specification (specific example group G5), the following unsubstituted alkynyl (specific example group G5A) etc. can be cited. (Here, unsubstituted alkynyl refers to the case where "substituted or unsubstituted alkynyl" is "unsubstituted alkynyl".) When simply expressed as "alkynyl" below, both "unsubstituted alkynyl" and "substituted alkynyl" are included.

"Substituted alkynyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkynyl" are replaced by a substituent. Specific examples of "substituted alkynyl" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl" (specific example group G5A) are replaced by a substituent.

Unsubstituted alkynyl (specific example group G5A):

Ethynyl.

"Substituted or unsubstituted cycloalkyl"

As specific examples of "substituted or unsubstituted cycloalkyl" described in the present specification (specific example group G6), the following unsubstituted cycloalkyl (specific example group G6A) and substituted cycloalkyl (specific example group G6B) can be cited. (Here, unsubstituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and substituted cycloalkyl refers to the case where "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl".) In the present specification, when only "cycloalkyl" is expressed, both "unsubstituted cycloalkyl" and "substituted cycloalkyl" are included.

"Substituted cycloalkyl" refers to a group in which one or more hydrogen atoms in an "unsubstituted cycloalkyl" are replaced by a substituent. Specific examples of "substituted cycloalkyl" include the following "unsubstituted cycloalkyl" (specific example group G6A) in which one or more hydrogen atoms are replaced by a substituent, and examples of substituted cycloalkyl (specific example group G6B). It should be noted that the examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" listed here are only examples, and the "substituted cycloalkyl" recorded in this specification also includes the group in which one or more hydrogen atoms bonded to the carbon atoms of the cycloalkyl itself in the "substituted cycloalkyl" of the specific example group G6B are replaced by a substituent, and the group in which the hydrogen atom of the substituent in the "substituted cycloalkyl" of the specific example group G6B is further replaced by a substituent.

Unsubstituted cycloalkyl (specific example group G6A):

Cyclopropyl,

Cyclobutyl,

Cyclopentyl,

Cyclohexyl,

1-adamantyl,

2-adamantyl,

1-Norbornyl and

2-Norborneol.

Substituted cycloalkyl (specific example group G6B):

4-Methylcyclohexyl.

· "a group represented by -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ )"

Specific examples of the group represented by -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ) described in the present specification (specific example group G7) include:

-Si(G1)(G1)(G1),

-Si(G1)(G2)(G2),

-Si(G1)(G1)(G2),

-Si(G2)(G2)(G2),

-Si(G3)(G3)(G3) and

-Si(G6)(G6)(G6). Here,

G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

A plurality of G1's in -Si(G1)(G1)(G1) are the same as or different from each other.

Multiple G2 in -Si(G1)(G2)(G2) are the same as or different from each other.

A plurality of G1's in -Si(G1)(G1)(G2) are the same as or different from each other.

Multiple G2s in -Si(G2)(G2)(G2) are the same as or different from each other.

Multiple G3 in -Si(G3)(G3)(G3) are the same as or different from each other.

Multiple G6's in -Si(G6)(G6)(G6) are the same as or different from each other.

· "the group represented by -O-(R ₉₀₄ )"

Specific examples of the group represented by -O-(R ₉₀₄ ) described in the present specification (specific example group G8) include

-O(G1),

-O(G2),

-O(G3) and

-O(G6).

Here,

G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

· "the group represented by -S-(R ₉₀₅ )"

Specific examples of the group represented by -S-(R ₉₀₅ ) described in the present specification (specific example group G9) include

-S(G1),

-S(G2),

-S(G3) and

-S(G6).

Here,

G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

· "a group represented by -N(R ₉₀₆ )(R ₉₀₇ )"

Specific examples of the group represented by -N(R ₉₀₆ )(R ₉₀₇ ) described in the present specification (specific example group G10) include

-N(G1)(G1),

-N(G2)(G2),

-N(G1)(G2),

-N(G3)(G3) and

-N(G6)(G6).

Here,

G1 is the "substituted or unsubstituted aryl group" described in Specific Example Group G1.

G2 is the "substituted or unsubstituted heterocyclic group" described in Specific Example Group G2.

G3 is the "substituted or unsubstituted alkyl group" described in Specific Example Group G3.

G6 is the "substituted or unsubstituted cycloalkyl group" described in Specific Example Group G6.

- A plurality of G1's in N(G1)(G1) are the same as or different from each other.

- Multiple G2 in N(G2)(G2) are the same as or different from each other.

- The multiple G3 in N(G3)(G3) are the same as or different from each other.

- A plurality of G6's in N(G6)(G6) are the same as or different from each other.

"Halogen atoms"

Specific examples of the "halogen atom" described in the present specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

"Substituted or unsubstituted fluoroalkyl"

The "substituted or unsubstituted fluoroalkyl group" described in the present specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting an alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting an alkyl group in a "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). The carbon number of the "unsubstituted fluoroalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise described in the present specification. The "substituted fluoroalkyl group" refers to a group in which one or more hydrogen atoms of a "fluoroalkyl group" are replaced with a substituent. It should be noted that the "substituted fluoroalkyl group" described in the present specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in a "substituted fluoroalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl group" (specific example group G3) are replaced with fluorine atoms.

"Substituted or unsubstituted haloalkyl"

The "substituted or unsubstituted haloalkyl group" described in the present specification refers to a group in which at least one hydrogen atom bonded to a carbon atom constituting an alkyl group in a "substituted or unsubstituted alkyl group" is replaced with a halogen atom, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting an alkyl group in a "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The carbon number of the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise described in the present specification. The "substituted haloalkyl group" refers to a group in which one or more hydrogen atoms of a "haloalkyl group" are replaced with a substituent. It should be noted that the "substituted haloalkyl group" described in the present specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in a "substituted haloalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of a substituent in a "substituted haloalkyl group" are further replaced with a substituent. Specific examples of "unsubstituted haloalkyl" include groups in which one or more hydrogen atoms in the above-mentioned "alkyl" (specific example group G3) are replaced with halogen atoms. A haloalkyl group is sometimes referred to as a halogenated alkyl group.

"Substituted or unsubstituted alkoxy"

A specific example of the "substituted or unsubstituted alkoxy group" described in the present specification is a group represented by -O(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The carbon number of the "unsubstituted alkoxy group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise described in the present specification.

"Substituted or unsubstituted alkylthio"

A specific example of the "substituted or unsubstituted alkylthio group" described in the present specification is a group represented by -S(G3), where G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3. The carbon number of the "unsubstituted alkylthio group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise described in the present specification.

"Substituted or unsubstituted aryloxy group"

A specific example of the "substituted or unsubstituted aryloxy group" described in the present specification is a group represented by -O(G1), where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of ring carbon atoms of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise described in the present specification.

"Substituted or unsubstituted arylthio"

A specific example of the "substituted or unsubstituted arylthio group" described in the present specification is a group represented by -S(G1), where G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. The number of ring carbon atoms of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise described in the present specification.

"Substituted or unsubstituted trialkylsilyl"

A specific example of a "trialkylsilyl group" described in the present specification is a group represented by -Si(G3)(G3)(G3), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3. A plurality of G3's in -Si(G3)(G3)(G3) may be identical to or different from each other. The number of carbon atoms in each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise described in the present specification.

"Substituted or unsubstituted aralkyl"

A specific example of the "substituted or unsubstituted aralkyl group" described in the present specification is a group represented by -(G3)-(G1), wherein G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1. Therefore, the "aralkyl group" is a group in which the hydrogen atom of the "alkyl group" is replaced by the "aryl group" as a substituent, and is one embodiment of the "substituted alkyl group". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group", and the carbon number of the "unsubstituted aralkyl group" is 7 to 50, preferably 7 to 30, and more preferably 7 to 18, unless otherwise described in the present specification.

Specific examples of the “substituted or unsubstituted aralkyl group” include benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylisopropyl, 2-phenylisopropyl, phenyl tert-butyl, α-naphthylmethyl, 1-α-naphthylethyl, 2-α-naphthylethyl, 1-α-naphthylisopropyl, 2-α-naphthylisopropyl, β-naphthylmethyl, 1-β-naphthylethyl, 2-β-naphthylethyl, 1-β-naphthylisopropyl and 2-β-naphthylisopropyl.

The substituted or unsubstituted aryl group described in the present specification is preferably phenyl, p-biphenyl, m-biphenyl, o-biphenyl, p-terphenyl-4-yl, p-terphenyl-3-yl, p-terphenyl-2-yl, m-terphenyl-4-yl, m-terphenyl-3-yl, m-terphenyl-2-yl, o-terphenyl-4-yl, o-terphenyl-3-yl, o-terphenyl-2-yl, 1-naphthyl, 2-naphthyl, anthracenyl, phenanthrenyl, pyrenyl, fluorenyl, 9,9'-spirobifluorenyl, 9,9-dimethylfluorenyl and 9,9-diphenylfluorenyl, etc.

The substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidyl group, a triazine group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group or 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzofuranyl group benzothiophene, azadibenzothiophene, diazadibenzothiophene, (9-phenyl)carbazol ((9-phenyl)carbazol-1-yl, (9-phenyl)carbazol-2-yl, (9-phenyl)carbazol-3-yl or (9-phenyl)carbazol-4-yl), (9-biphenyl)carbazol, (9-phenyl)phenylcarbazol, diphenylcarbazol-9-yl, phenylcarbazol-9-yl, phenyltriazine, biphenyltriazine, diphenyltriazine, phenyldibenzofuranyl and phenyldibenzothiophene, etc.

In the present specification, the carbazolyl group is specifically any of the following groups unless otherwise described in the present specification.

【Chemical formula 9】

In the present specification, the (9-phenyl)carbazolyl group is specifically any of the following groups unless otherwise specified in the present specification.

【Chemical formula 10】

In the above general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a bonding position.

In the present specification, the dibenzofuranyl group and the dibenzothienyl group are specifically any of the following groups unless otherwise specified in the present specification.

【Chemical formula 11】

In the above general formulas (TEMP-34) to (TEMP-41), * represents a bonding position.

The substituted or unsubstituted alkyl group described in the present specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, or the like, unless otherwise described in the present specification.

"Substituted or unsubstituted arylene group"

Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted aryl group" by removing one hydrogen atom on the aryl ring. Specific examples of the "substituted or unsubstituted arylene group" (specific example group G12) include divalent groups derived from the "substituted or unsubstituted aryl group" described in specific example group G1 by removing one hydrogen atom on the aryl ring.

"Substituted or unsubstituted divalent heterocyclic group"

Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted heterocyclic group" by removing one hydrogen atom on the heterocyclic ring. Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include divalent groups derived from the "substituted or unsubstituted heterocyclic group" described in specific example group G2 by removing one hydrogen atom on the heterocyclic ring.

"Substituted or unsubstituted alkylene"

Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived from the above-mentioned "substituted or unsubstituted alkyl group" by removing one hydrogen atom on the alkyl chain. Specific examples of the "substituted or unsubstituted alkylene group" (specific example group G14) include divalent groups derived from the "substituted or unsubstituted alkyl group" described in specific example group G3 by removing one hydrogen atom on the alkyl chain.

The substituted or unsubstituted arylene group described in the present specification is preferably any one of the following general formulae (TEMP-42) to (TEMP-68) unless otherwise described in the present specification.

【Chemical formula 12】

【Chemical formula 13】

In the above general formulae (TEMP-42) to (TEMP-52), Q ₁ to Q ₁₀ are each independently a hydrogen atom or a substituent.

In the above general formulas (TEMP-42) to (TEMP-52), * represents a bonding position.

【Chemical formula 14】

In the above general formulae (TEMP-53) to (TEMP-62), Q ₁ to Q ₁₀ are each independently a hydrogen atom or a substituent.

Formulas _Q9 and _Q10 may be bonded to each other via a single bond to form a ring.

In the above general formulas (TEMP-53) to (TEMP-62), * represents a bonding position.

【Chemical formula 15】

In the above general formulae (TEMP-63) to (TEMP-68), Q ₁ to Q ₈ are each independently a hydrogen atom or a substituent.

In the above general formulas (TEMP-63) to (TEMP-68), * represents a bonding position.

The substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the following general formulae (TEMP-69) to (TEMP-102) unless otherwise described in the present specification.

【Chemical formula 16】

【Chemical formula 17】

【Chemical formula 18】

In the above general formulae (TEMP-69) to (TEMP-82), Q ₁ to Q ₉ are each independently a hydrogen atom or a substituent.

【Chemical formula 19】

【Chemical formula 20】

【Chemical formula 21】

【Chemical formula 22】

In the above general formulae (TEMP-83) to (TEMP-102), Q ₁ to Q ₈ are each independently a hydrogen atom or a substituent.

The above is the description of the “substituents described in the present specification”.

・"When bonding to form a ring"

In the present specification, the expression "one or more groups consisting of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other" means the case where "one or more groups consisting of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted monocyclic ring", the case where "one or more groups consisting of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted condensed ring", and the case where "one or more groups consisting of two or more adjacent groups ... are not bonded to each other".

Hereinafter, the case of "one or more of the groups consisting of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted monocyclic ring" and the case of "one or more of the groups consisting of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted condensed ring" in this specification (hereinafter, these cases are sometimes collectively referred to as "cases of bonding to form a ring.") are explained. The case of an anthracene compound represented by the following general formula (TEMP-103) in which the mother skeleton is an anthracene ring is explained as an example.

【Chemical formula 23】

For example, in the case of “one or more groups of two or more adjacent groups among _R921 to _R930 are bonded to each other to form a ring”, the group consisting of two adjacent groups as one group refers to the group of _R921 and _R922 , the group of _R922 and _R923 , the group of _R923 and _R924 , the group of _R924 and _R930 , the group of _R930 and _R925 , the group of _R925 and _R926 , the group of _R926 and _R927 , the group of _R927 and _R928 , the group of _R928 and _R929 , and the group of _R929 and _R921 .

The above-mentioned "one or more groups" means that two or more groups of the above-mentioned groups consisting of two or more adjacent groups can simultaneously form a ring. For example, when _R921 and _R922 are bonded to each other to form a ring _QA and _R925 and _R926 are bonded to each other to form a ring _QB , the anthracene compound represented by the above-mentioned general formula (TEMP-103) is represented by the following general formula (TEMP-104).

【Chemical formula 24】

The case where "a group consisting of two or more adjacent groups" forms a ring includes not only the case where a group consisting of "two" adjacent groups is bonded as in the above example, but also the case where a group consisting of "three or more" adjacent groups is bonded. For example, R ₉₂₁ and R ₉₂₂ are bonded to each other to form a ring Q _A , and R ₉₂₂ and R ₉₂₃ are bonded to each other to form a ring Q _C , and a group consisting of three adjacent groups (R ₉₂₁ , R ₉₂₂ and R ₉₂₃ ) are bonded to each other to form a ring and fused to the anthracene mother skeleton. In this case, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q _A and ring Q _C share R ₉₂₂ .

【Chemical formula 25】

In the "monocyclic ring" or "condensed ring" formed, as the structure of the ring formed only, it can be a saturated ring or an unsaturated ring. Even if "one group of two adjacent groups" forms a "monocyclic ring" or a "condensed ring", the "monocyclic ring" or "condensed ring" can also form a saturated ring or an unsaturated ring. For example, the ring Q _A and the ring Q _B formed in the above-mentioned general formula (TEMP-104) are each a "monocyclic ring" or a "condensed ring". In addition, the ring Q A and the ring Q _C formed in the above-mentioned general formula (TEMP-105) are "condensed rings". The ring Q _A and the ring Q _C of the above-mentioned general formula (TEMP-105) form a condensed ring by fusing the ring Q _A and the ring Q _C. If the ring Q _A of the above-mentioned general formula (TMEP-104) is a benzene _ring , the ring Q _A is a monocyclic ring. If the ring Q _A of the above-mentioned general formula (TMEP-104) is a naphthalene ring, the ring Q _A is a condensed ring.

The "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.

Specific examples of the aromatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G1 are terminated with hydrogen atoms.

Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified as specific examples in Specific Example Group G2 are terminated with hydrogen atoms.

Specific examples of the aliphatic hydrocarbon ring include structures in which the groups exemplified as specific examples in Specific Example Group G6 are terminated with hydrogen atoms.

"Forming a ring" means that a ring is formed only by multiple atoms of the parent skeleton, or a ring is formed by multiple atoms of the parent skeleton and one or more other optional elements. For example, the ring Q _A formed by R ₉₂₁ and R ₉₂₂ bonded to each other as shown in the general formula (TEMP-104) refers to a ring formed by the carbon atom of the anthracene skeleton bonded by R ₉₂₁ , the carbon atom of the anthracene skeleton bonded by R ₉₂₂ , and one or more optional elements. As a specific example, in the case of forming the ring Q _A by R ₉₂₁ and R ₉₂₂ , in the case of a monocyclic unsaturated ring formed by the carbon atom of the anthracene skeleton bonded by R ₉₂₁ , the carbon atom of the anthracene skeleton bonded by R ₉₂₂ , and 4 carbon atoms, the ring formed by R ₉₂₁ and R ₉₂₂ is a benzene ring.

Here, "optional element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur as long as it is not otherwise described in this specification. In the optional element (for example, in the case of carbon or nitrogen), the bond that does not form a ring can be terminated by hydrogen atoms or the like, or can be replaced by an "optional substituent" described later. When an optional element other than carbon is included, the ring formed is a heterocycle.

Unless otherwise specified in the present specification, the number of "one or more optional elements" constituting a monocyclic or condensed ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.

Unless otherwise specified in the present specification, "monocyclic ring" is preferred among "monocyclic ring" and "condensed ring".

In the present specification, unless otherwise specified, among "saturated ring" and "unsaturated ring", "unsaturated ring" is preferred.

Unless otherwise specified in the present specification, a "monocyclic ring" is preferably a benzene ring.

Unless otherwise specified in the present specification, the "unsaturated ring" is preferably a benzene ring.

In the case of "one or more groups consisting of two or more adjacent groups ... are "bonded to each other to form a substituted or unsubstituted single ring" or "bonded to each other to form a substituted or unsubstituted condensed ring", unless otherwise stated in the present specification, it is preferably one or more groups consisting of two or more adjacent groups ... are bonded to each other to form a substituted or unsubstituted "unsaturated ring" formed by multiple atoms of the parent skeleton and at least one element selected from the group consisting of carbon, nitrogen, oxygen and sulfur.

When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, the "optional substituent" described later. Specific examples of the substituent when the above-mentioned "monocyclic ring" or "condensed ring" has a substituent are the substituents described in the above-mentioned "substituents described in the present specification".

When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described later. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above-mentioned "substituents described in the present specification".

The above is an explanation of the case where "one or more groups of two or more adjacent groups of ... are bonded to each other to form a substituted or unsubstituted single ring" and the case where "one or more groups of two or more adjacent groups of ... are bonded to each other to form a substituted or unsubstituted condensed ring" ("the case where they are bonded to form a ring").

·Substituents when expressed as "substituted or unsubstituted"

In one embodiment of the present specification, the substituent described as "substituted or unsubstituted" (sometimes referred to as "optional substituent" in the present specification) is selected from, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms,

unsubstituted alkenyl having 2 to 50 carbon atoms,

unsubstituted alkynyl having 2 to 50 carbon atoms,

unsubstituted cycloalkyl having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ )、

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms, cyano, nitro,

unsubstituted aryl group having 6 to 50 ring carbon atoms and

Unsubstituted heterocyclic group having 5 to 50 ring atoms

The groups in the group etc.

Here, R ₉₀₁ to R ₉₀₇ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

When there are two or more R ₉₀₁ , the two or more R ₉₀₁ are the same as or different from each other.

When there are two or more R ₉₀₂ , the two or more R ₉₀₂ are the same as or different from each other.

When there are two or more R ₉₀₃ , the two or more R ₉₀₃ are the same as or different from each other.

When there are two or more R ₉₀₄ , the two or more R ₉₀₄ are the same as or different from each other.

When there are two or more R ₉₀₅ , the two or more R ₉₀₅ are the same as or different from each other.

When there are two or more R ₉₀₆ , the two or more R ₉₀₆ are the same as or different from each other.

When there are two or more R _{907 s} , the two or more R _{907 s} are the same as or different from each other.

In one embodiment, the substituents described as "substituted or unsubstituted" are selected from

an alkyl group having 1 to 50 carbon atoms,

An aryl group having 6 to 50 ring carbon atoms and

A group selected from the group consisting of heterocyclic groups having 5 to 50 ring atoms.

In one embodiment, the substituents described as "substituted or unsubstituted" are selected from

an alkyl group having 1 to 18 carbon atoms,

An aryl group having 6 to 18 ring carbon atoms and

A group selected from the group consisting of heterocyclic groups having 5 to 18 ring atoms.

Specific examples of each of the above optional substituents are the same as the specific examples of the substituents described in the above section "substituents described in the present specification".

Unless otherwise stated in the present specification, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated five-membered ring, a substituted or unsubstituted saturated six-membered ring, a substituted or unsubstituted unsaturated five-membered ring, or a substituted or unsubstituted unsaturated six-membered ring, more preferably a benzene ring.

Unless otherwise specified in the present specification, an optional substituent may further have a substituent. The substituent further possessed by the optional substituent is the same as the above-mentioned optional substituent.

In this specification, the numerical range expressed using "AA to BB" means a range including the numerical value AA described before "AA to BB" as the lower limit value and the numerical value BB described after "AA to BB" as the upper limit value.

[First embodiment]

(Compound)

The compound according to this embodiment is a compound represented by the following general formula (1C-A).

【Chemical formula 26】

(In the above general formula (1C-A),

One of R ₄ to R ₈ and R ₁₀ to R ₁₂ is a group represented by the above general formula (1D-A),

R ₁ to R ₃ , R ₉ , and R ₄ to R ₈ and R ₁₀ to R ₁₂ other than the group represented by the above general formula (1D-A) are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C(=O)R ₈₀₁ ,

-COOR ₈₀₂ ,

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

When R ₁₁ is a group represented by the above general formula (1D-A), R ₁₂ is a hydrogen atom or a substituted or unsubstituted phenyl group,

When R ₁₂ is a group represented by the above general formula (1D-A), R ₁₁ is a hydrogen atom or a substituted or unsubstituted phenyl group,

In the above general formula (1D-A), one of R ₂₁ to R ₃₀ represents a bonding position to the benz[a]anthracene ring in the above general formula (1C-A), and one or more groups of two or more adjacent R ₂₁ to R ₃₀ in the above general formula (1D-A) that are not the bonding position are included.

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R 21 to R 30 in the above general formula (1D-A) that are not bonded to the benz[a]anthracene ring in the above general formula (1C-A), do not form the above substituted or unsubstituted monocyclic ring, and do not form the above _substituted or _{unsubstituted} condensed ring are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

wherein at least one of R ₂₁ to R ₃₀ is a group other than a hydrogen atom,

In the compound represented by the above general formula (1C-A), R ₉₀₁ , R ₉₀₂ , R ₉₀₃ , R ₉₀₄ , R ₉₀₅ , R ₉₀₆ , R ₉₀₇ , R ₈₀₁ and R ₈₀₂ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

When there are a plurality of R ₉₀₁ , the plurality of R ₉₀₁ are the same as or different from each other.

When there are multiple R ₉₀₂ , the multiple R ₉₀₂ are the same as or different from each other.

When there are multiple R ₉₀₃ , the multiple R ₉₀₃ are the same as or different from each other.

When there are a plurality of R ₉₀₄ , the plurality of R ₉₀₄ are the same as or different from each other.

When there are multiple R ₉₀₅ , the multiple R ₉₀₅ are the same as or different from each other.

When there are multiple R ₉₀₆ , the multiple R ₉₀₆ are the same as or different from each other.

When there are a plurality of R ₉₀₇ , the plurality of R ₉₀₇ are the same as or different from each other.

When there are multiple _R801 , the multiple _R801 are the same as or different from each other.

When there are multiple R ₈₀₂ , the multiple R ₈₀₂ are the same as or different from each other.)

In the compounds involved in this embodiment, it is also preferred that at least one of R 21 to R 30 in the general formula (1D-A) that is not a bonding position to the benz[a]anthracene ring in the general formula (1C-A), does not form the substituted or unsubstituted monocyclic ring, does not form the substituted or unsubstituted condensed ring and is not a hydrogen atom is a substituted or unsubstituted aromatic group having ₆ to ₅₀ ring carbon atoms.

In the compounds involved in this embodiment, it is also preferred that at least one of R 21 to R 30 in the general formula (1D-A) that is not a bonding position with the benz[a]anthracene ring in the general formula (1C-A), does not form the substituted or unsubstituted monocyclic ring, does not form the _substituted or unsubstituted condensed ring and _is not a hydrogen atom is a substituted or unsubstituted phenyl group.

In the compound involved in this embodiment, it is also preferred that the group represented by the above-mentioned general formula (1D-A) is a group represented by the following general formula (1D-A1), general formula (1D-A2) or general formula (1D-A3).

【Chemical formula 27】

(In the above general formula (1D-A1),

One or more of the groups consisting of two or more adjacent ones of R ₂₁ to R ₂₉

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₂₁ to R ₂₉ which do not form the above substituted or unsubstituted monocyclic ring and do not form the above substituted or unsubstituted condensed ring are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

wherein at least one of R ₂₁ to R ₂₉ is a group other than a hydrogen atom,

* represents the bonding position to the benz[a]anthracene ring in the above general formula (1C-A),

In the above general formula (1D-A2),

One or more of the groups consisting of two or more adjacent ones of R ₂₁ to R ₂₈ and R ₃₀

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₂₁ to R ₂₈ and R ₃₀ which do not form the above substituted or unsubstituted monocyclic ring and do not form the above substituted or unsubstituted condensed ring are each independently the same as R ₂₁ to R ₂₉ in the above general formula (1D-A1),

wherein at least one of R ₂₁ to R ₂₈ and R ₃₀ is a group other than a hydrogen atom,

* represents the bonding position to the benz[a]anthracene ring in the above general formula (1C-A),

In the above general formula (1D-A3),

One or more of the group consisting of two or more adjacent ones of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ which do not form the above-mentioned substituted or unsubstituted monocyclic ring and do not form the above-mentioned substituted or unsubstituted condensed ring are each independently the same as R ₂₁ to R ₂₉ in the above-mentioned general formula (1D-A1).

wherein at least one of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ is a group other than a hydrogen atom,

* represents the bonding position to the benz[a]anthracene ring in the above general formula (1C-A).

In the compounds involved in the present embodiment, it is also preferred that the groups represented by the general formula (1D-A1), the general formula (1D-A2) or the general formula (1D-A3) do not form the substituted or unsubstituted monocyclic ring, do not form the substituted or unsubstituted condensed ring and are not a hydrogen atom, and at least one of R ₂₁ to R ₂₉ in the general formula (1D-A1), at least one of R ₂₁ to R ₂₈ and R ₃₀ in the general formula (1D-A2), or at least one of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ in the general formula (1D-A3) is a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms.

In the compounds involved in the present embodiment, it is also preferred that the groups represented by the general formula (1D-A1), the general formula (1D-A2) or the general formula (1D-A3) do not form the substituted or unsubstituted monocyclic ring, do not form the substituted or unsubstituted condensed ring and are not hydrogen atoms, at least one of R ₂₁ to R ₂₉ in the general formula (1D-A1), at least one of R ₂₁ to R ₂₈ and R ₃₀ in the general formula (1D-A2), or at least one of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ in the general formula (1D-A3) are substituted or unsubstituted phenyl groups.

In the compound according to this embodiment, it is also preferred that the group represented by the general formula (1D-A) is a group represented by the general formula (1D-A1).

In the compound according to this embodiment, it is also preferred that one of R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ is a group represented by the above general formula (1D-A).

In the compound according to this embodiment, it is also preferred that one of R ₆ , R ₇ , R ₁₁ and R ₁₂ is a group represented by the above-mentioned general formula (1D-A).

In the compound according to this embodiment, it is also preferred that R ₁₁ is a group represented by the above-mentioned general formula (1D-A).

Among the compounds according to this embodiment, compounds wherein R ₁₂ is a group represented by the above-mentioned general formula (1D-A) are also preferred.

In the compound involved in this embodiment, it is also preferred that R ₁₁ is a group represented by the above general formula (1D-A) and R ₁₂ is an unsubstituted phenyl group, or R ₁₂ is a group represented by the above general formula (1D-A) and R ₁₁ is an unsubstituted phenyl group.

In the compound according to this embodiment, it is also preferred that R ₁₁ is a group represented by the above general formula (1D-A) and R ₁₂ is an unsubstituted phenyl group.

In the compound according to this embodiment, it is also preferred that R ₁₂ is a group represented by the above general formula (1D-A) and R ₁₁ is an unsubstituted phenyl group.

The compound according to this embodiment is also preferably a compound represented by the following general formula (1C-A-1).

The compound according to this embodiment is also preferably a compound represented by the following general formula (1C-A-2).

【Chemical formula 28】

【Chemical formula 29】

(R ₁ to R ₁₁ in the above general formula (1C-A-1) and R ₁ to R ₁₀ and R ₁₂ in the above general formula (1C-A-2) are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C(=O)R ₈₀₁ ,

-COOR ₈₀₂ ,

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

In the above general formulae (1C-A-1) and (1C-A-2), R ₂₁ to R ₂₈ and R ₃₀ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

In which, at least one of R ₂₁ to R ₂₈ and R ₃₀ is a group other than a hydrogen atom.)

In the compound according to this embodiment, it is also preferred that R ₁₂ is a hydrogen atom.

The compound according to this embodiment preferably has one or more deuterium atoms in the molecule.

In the compound according to this embodiment, it is also preferred that at least one of R ₁ to R ₃ and R ₉ when they are hydrogen atoms, R ₄ to R ₈ and R ₁₀ to R ₁₂ when they are hydrogen atoms other than the group represented by the general formula (1D-A), and R ₂₁ to R ₃₀ when they are hydrogen atoms is a deuterium atom.

In the compound according to this embodiment, it is also preferred that R ₁ to R ₃ and R ₉ when they are hydrogen atoms, R ₄ to R ₈ and R ₁₀ to R ₁₂ when they are hydrogen atoms other than the group represented by the general formula (1D-A), and R ₂₁ to R ₃₀ when they are hydrogen atoms are all deuterium atoms.

In the compound involved in the present embodiment, it is also preferred that when R ₁ to R ₃ and R ₉ when they are groups other than hydrogen atoms, R ₄ to R ₈ and R ₁₀ to R ₁₂ when they are groups other than hydrogen atoms except the group represented by the above general formula (1D-A), and R ₂₁ to R ₃₀ when they are groups other than hydrogen atoms each have a hydrogen atom, at least one of the hydrogen atoms is a deuterium atom.

In the compound involved in this embodiment, it is also preferred that when R ₁ to R ₃ and R ₉ when they are groups other than hydrogen atoms, R ₄ to R ₈ and R ₁₀ to R ₁₂ when they are groups other than hydrogen atoms except the group represented by the above general formula (1D-A), and R ₂₁ to R ₃₀ when they are groups other than hydrogen atoms each have a hydrogen atom, the hydrogen atom is preferably a deuterium atom.

In the compound according to this embodiment, when one of R ₅ , R ₆ , R ₇ and R ₈ is a group represented by the above general formula (1D-A), it is also preferred that R ₂ and R ₃ are hydrogen atoms.

Among the compounds according to the present embodiment, compounds not containing a heteroatom in the molecule are also preferred.

In the compound according to the present embodiment, it is also preferred that all the groups described as "substituted or unsubstituted" are "unsubstituted" groups, and all the rings described as "substituted or unsubstituted" are "unsubstituted" rings.

·Method for producing the compound according to this embodiment

The compound involved in this embodiment can be produced according to the synthesis method described in the Examples described below. In addition, the compound involved in this embodiment can also be produced by following the synthesis method by using a known substitution reaction and raw materials corresponding to the target substance.

Specific examples of the compounds according to this embodiment

As specific examples of the compounds involved in this embodiment, for example, compounds falling within the scope of the compounds involved in this embodiment among the compounds exemplified in the compound represented by the general formula (1C) as the first compound used in the organic electroluminescent element involved in the fourth embodiment described later are specific examples of the compounds involved in this embodiment.

[Second Embodiment]

(Compound)

The compound according to this embodiment is a compound represented by the following general formula (1C-B).

【Chemical formula 30】

(In the above general formula (1C-B),

One of R ₄ to R ₆ , R ₈ and R 1 ₀ to R ₁₂ is a group represented by the above general formula (1D-B),

R ₁ to R ₃ , R ₇ , R ₉ , and R ₄ to R ₆ , R ₈ and R ₁₀ to R ₁₂ other than the group represented by the above general formula (1D-B) are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C(=O)R ₈₀₁ ,

-COOR ₈₀₂ ,

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

When R ₁₁ is a group represented by the above general formula (1D-B), R ₁₂ is a hydrogen atom or an unsubstituted phenyl group,

When R ₁₂ is a group represented by the above general formula (1D-B), R ₁₁ is a substituted or unsubstituted phenyl group,

In the above general formula (1D-B), one of R ₂₁ to R ₃₀ represents a bonding position to the benz[a]anthracene ring in the above general formula (1C-B), and one or more groups of two or more adjacent R ₂₁ to R ₃₀ in the above general formula (1D-B) that are not the bonding position are included.

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R 21 to R 30 in the above general formula (1D-B) that are not bonded to the benz[a]anthracene ring in the above general formula (1C-B), do not form the above substituted or unsubstituted monocyclic ring, and do not form the above _substituted or _{unsubstituted} condensed ring are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

In the compound represented by the above general formula (1C-B), R ₉₀₁ , R ₉₀₂ , R ₉₀₃ , R ₉₀₄ , R ₉₀₅ , R ₉₀₆ , R ₉₀₇ , R ₈₀₁ and R ₈₀₂ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

When there are a plurality of R ₉₀₁ , the plurality of R ₉₀₁ are the same as or different from each other.

When there are multiple R ₉₀₂ , the multiple R ₉₀₂ are the same as or different from each other.

When there are multiple R ₉₀₃ , the multiple R ₉₀₃ are the same as or different from each other.

When there are a plurality of R ₉₀₄ , the plurality of R ₉₀₄ are the same as or different from each other.

When there are multiple R ₉₀₅ , the multiple R ₉₀₅ are the same as or different from each other.

When there are multiple R ₉₀₆ , the multiple R ₉₀₆ are the same as or different from each other.

When there are a plurality of R ₉₀₇ , the plurality of R ₉₀₇ are the same as or different from each other.

When there are multiple _R801 , the multiple _R801 are the same as or different from each other.

When there are multiple R ₈₀₂ , the multiple R ₈₀₂ are the same as or different from each other.)

In the compounds involved in this embodiment, it is also preferred that at least one of R 21 to R 30 in the general formula (1D-B) that is not a bonding position to the benz[a]anthracene ring in _the general formula (1C-B) and does not form the substituted or unsubstituted monocyclic ring and the _substituted or unsubstituted condensed ring is a group other than a hydrogen atom.

In the compounds involved in this embodiment, it is also preferred that in the group represented by the general formula (1D-B), at least one of R 21 to R 30 in the general formula (1D-B) that is not a bonding position to the benz[a]anthracene ring in _the general formula (1C-B) and does not form the substituted or _{unsubstituted} monocyclic ring and does not form the substituted or unsubstituted condensed ring is a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms.

In the compounds involved in this embodiment, it is also preferred that at least one of R 21 to R 30 in the general formula (1D-B) that is not a bonding position to the benz[a]anthracene ring in _the general formula (1C-B) and does not form the substituted or unsubstituted monocyclic ring and the _substituted or unsubstituted condensed ring is a substituted or unsubstituted phenyl group.

In the compound involved in this embodiment, it is also preferred that the group represented by the above-mentioned general formula (1D-B) is a group represented by the following general formula (1D-B1), general formula (1D-B2) or general formula (1D-B3).

【Chemical formula 31】

(In the above general formula (1D-B1),

One or more of the groups consisting of two or more adjacent ones of R ₂₁ to R ₂₉

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₂₁ to R ₂₉ which do not form the above substituted or unsubstituted monocyclic ring and do not form the above substituted or unsubstituted condensed ring are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

* represents the bonding position to the benz[a]anthracene ring in the above general formula (1C-B),

In the above general formula (1D-B2),

One or more of the groups consisting of two or more adjacent ones of R ₂₁ to R ₂₈ and R ₃₀

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₂₁ to R ₂₈ and R ₃₀ which do not form the above-mentioned substituted or unsubstituted monocyclic ring and do not form the above-mentioned substituted or unsubstituted condensed ring are each independently the same as R ₂₁ to R ₂₉ in the above-mentioned general formula (1D-B1),

* represents the bonding position to the benz[a]anthracene ring in the above general formula (1C-B),

In the above general formula (1D-B3),

One or more of the group consisting of two or more adjacent ones of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ which do not form the above substituted or unsubstituted monocyclic ring and do not form the above substituted or unsubstituted condensed ring are each independently the same as R ₂₁ to R ₂₉ in the above general formula (1D-B1).

* represents the bonding position to the benz[a]anthracene ring in the above general formula (1C-B).

In the compounds involved in the present embodiment, it is also preferred that in the groups represented by the general formula (1D-B1), the general formula (1D-B2) or the general formula (1D-B3), at least one of R ₂₁ to R ₂₉ in the general formula (1D-B1) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, at least one of R ₂₁ to R ₂₈ and R ₃₀ in the general formula (1D-B2), or at least one of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ in the general formula (1D-B3) is a group other than a hydrogen atom.

In the compounds involved in the present embodiment, it is also preferred that in the groups represented by the general formula (1D-B1), the general formula (1D-B2) or the general formula (1D-B3), at least one of R ₂₁ to R ₂₉ in the general formula (1D-B1) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, at least one of R ₂₁ to R ₂₈ and R ₃₀ in the general formula (1D-B2), or at least one of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ in the general formula (1D-B3) is a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms.

In the compounds involved in the present embodiment, it is also preferred that in the groups represented by the general formula (1D-B1), the general formula (1D-B2) or the general formula (1D-B3), at least one of R ₂₁ to R ₂₉ in the general formula (1D-B1) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, at least one of R ₂₁ to R ₂₈ and R ₃₀ in the general formula (1D-B2), or at least one of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ in the general formula (1D-B3) is a substituted or unsubstituted phenyl group.

In the compound according to this embodiment, it is also preferred that the group represented by the general formula (1D-B) is a group represented by the general formula (1D-B1).

In the compound according to this embodiment, it is also preferred that one of R ₅ , R ₆ , R ₈ , R ₁₁ and R ₁₂ is a group represented by the above general formula (1D-B).

In the compound according to this embodiment, it is also preferred that one of R ₆ , R ₁₁ and R ₁₂ is a group represented by the above-mentioned general formula (1D-B).

In the compound according to this embodiment, it is also preferred that R ₁₁ is a group represented by the above-mentioned general formula (1D-B).

In the compound according to this embodiment, it is also preferred that R ₁₂ is a group represented by the above-mentioned general formula (1D-B).

In the compound involved in this embodiment, it is also preferred that R ₁₁ is a group represented by the above general formula (1D-B) and R ₁₂ is an unsubstituted phenyl group, or R ₁₂ is a group represented by the above general formula (1D-B) and R ₁₁ is an unsubstituted phenyl group.

In the compound according to this embodiment, it is also preferred that R ₁₁ is a group represented by the above general formula (1D-B), and R ₁₂ is an unsubstituted phenyl group.

In the compound according to this embodiment, it is also preferred that R ₁₂ is a group represented by the above general formula (1D-B), and R ₁₁ is an unsubstituted phenyl group.

The compound according to the present embodiment is also preferably a compound represented by the following general formula (1C-B-1).

The compound according to the present embodiment is also preferably a compound represented by the following general formula (1C-B-2).

【Chemical formula 32】

【Chemical formula 33】

(R ₁ to R ₁₀ in the above general formula (1C-B-1) and R ₁ to R ₁₀ in the above general formula (1C-B-2) are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C(=O)R ₈₀₁ ,

-COOR ₈₀₂ ,

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

In the above general formulae (1C-B-1) and (1C-B-2), R ₂₁ to R ₂₈ and R ₃₀ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

In the above general formula (1C-B-1), R ₁₁ is a substituted or unsubstituted phenyl group,

In the above general formula (1C-B-2), R ₁₂ is a hydrogen atom or an unsubstituted phenyl group.

In the compound according to this embodiment, it is also preferred that R ₇ and R ₁₂ are hydrogen atoms.

The compound according to this embodiment also preferably has one or more deuterium atoms in the molecule.

In the compound according to this embodiment, it is also preferred that at least one of R ₁ to R ₃ , R ₇ , and R ₉ when they are hydrogen atoms, R ₄ to R ₆ , R ₈ , and R ₁₀ to R ₁₂ when they are hydrogen atoms other than the group represented by the general formula (1D-B), and R ₂₁ to R ₃₀ when they are hydrogen atoms is a deuterium atom.

In the compound according to this embodiment, it is also preferred that R ₁ to R ₃ , R ₇ , and R ₉ when they are hydrogen atoms, R ₄ to R ₆ , R ₈ , and R ₁₀ to R ₁₂ when they are hydrogen atoms other than the group represented by the general formula (1D-B), and R ₂₁ to R ₃₀ when they are hydrogen atoms are all deuterium atoms.

In the compound involved in the present embodiment, it is also preferred that when R ₁ to R ₃ , R ₇ , R ₉ when they are groups other than hydrogen atoms, R ₄ to R ₈ and R ₁₀ to R ₁₂ when they are groups other than hydrogen atoms except the group represented by the above general formula (1D-B), and R ₂₁ to R ₃₀ when they are groups other than hydrogen atoms each have a hydrogen atom, at least one of the hydrogen atoms is a deuterium atom.

In the compound involved in this embodiment, it is also preferred that when R ₁ to R ₃ , R ₇ , and R ₉ when they are groups other than hydrogen atoms, and R ₄ to R ₈ and R ₁₀ to R ₁₂ when they are groups other than hydrogen atoms except the group represented by the above general formula (1D-B), and R ₂₁ to R ₃₀ when they are groups other than hydrogen atoms each have a hydrogen atom, the hydrogen atom is preferably a deuterium atom.

Among the compounds according to the present embodiment, compounds not containing a heteroatom in the molecule are also preferred.

In the compound according to the present embodiment, it is also preferred that all the groups described as "substituted or unsubstituted" are "unsubstituted" groups, and all the rings described as "substituted or unsubstituted" are "unsubstituted" rings.

·Method for producing the compound according to this embodiment

The compound involved in this embodiment can be produced according to the synthesis method described in the Examples described below. In addition, the compound involved in this embodiment can also be produced by following the synthesis method by using a known substitution reaction and raw materials corresponding to the target substance.

Specific examples of the compounds according to this embodiment

As specific examples of the compounds involved in this embodiment, for example, compounds falling within the scope of the compounds involved in this embodiment among the compounds exemplified in the compound represented by the general formula (1C) as the first compound used in the organic electroluminescent element involved in the fourth embodiment described later are specific examples of the compounds involved in this embodiment.

[Third Embodiment]

(Compound)

The compound according to this embodiment is a compound represented by the following general formula (1C-C).

【Chemical formula 34】

(In the above general formula (1C-C),

One of R ₄ to R ₈ and R ₁₀ to R ₁₂ is a group represented by the above general formula (1D-C),

R ₁ to R ₃ , R ₉ , and R ₄ to R ₈ and R ₁₀ to R ₁₂ other than the group represented by the above general formula (1D-C) are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C(=O)R ₈₀₁ ,

-COOR ₈₀₂ ,

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

When R ₁₁ is a group represented by the above general formula (1D-C), R ₁₂ is a hydrogen atom or a substituted or unsubstituted phenyl group,

When R ₁₂ is a group represented by the above general formula (1D-C), R ₁₁ is a hydrogen atom or a substituted or unsubstituted phenyl group,

In the above general formula (1D-C), one of R ₂₂ , R ₂₃ , R ₂₅ , R ₂₇ , R ₂₈ and R ₃₀ represents a bonding position to the benzo[a]anthracene ring in the above general formula (1C-C), and one or more of the group consisting of R ₂₁ , R ₂₄ , R ₂₆ and R ₂₉ , and two or more adjacent ones of R ₂₂ , R ₂₃ , R ₂₅ , R ₂₇ , R ₂₈ and R ₃₀ in the above general formula (1D-C) that are not the bonding position.

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R 21 to R 30 in the above general formula (1D-C) that are not bonded to the benz[a]anthracene ring in the above general formula (1C-C), that do not form the above substituted or unsubstituted monocyclic ring, and that do not form the above _substituted or _{unsubstituted} condensed ring are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

In the compound represented by the above general formula (1C-C), R ₉₀₁ , R ₉₀₂ , R ₉₀₃ , R ₉₀₄ , R ₉₀₅ , R ₉₀₆ , R ₉₀₇ , R ₈₀₁ and R ₈₀₂ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

When there are a plurality of R ₉₀₁ , the plurality of R ₉₀₁ are the same as or different from each other.

When there are multiple R ₉₀₂ , the multiple R ₉₀₂ are the same as or different from each other.

When there are multiple R ₉₀₃ , the multiple R ₉₀₃ are the same as or different from each other.

When there are a plurality of R ₉₀₄ , the plurality of R ₉₀₄ are the same as or different from each other.

When there are multiple R ₉₀₅ , the multiple R ₉₀₅ are the same as or different from each other.

When there are multiple R ₉₀₆ , the multiple R ₉₀₆ are the same as or different from each other.

When there are a plurality of R ₉₀₇ , the plurality of R ₉₀₇ are the same as or different from each other.

When there are multiple _R801 , the multiple _R801 are the same as or different from each other.

When there are multiple R ₈₀₂ , the multiple R ₈₀₂ are the same as or different from each other.)

In the compound involved in this embodiment, it is also preferred that in the group represented by the general formula (1D-C), at least one of R 21 to R 30 in the general formula (1D-C) that is not a bonding position to the benz[a]anthracene ring in _the general formula (1C-C) and does not form the substituted or _{unsubstituted} monocyclic ring and does not form the substituted or unsubstituted condensed ring is a group other than a hydrogen atom.

In the compound involved in this embodiment, it is also preferred that in the group represented by the general formula (1D-C), at least one of R 21 to R 30 in the general formula (1D-C) that is not a bonding position to the benz[a]anthracene ring in _the general formula (1C-C) and does not form the substituted or _{unsubstituted} monocyclic ring and does not form the substituted or unsubstituted condensed ring is a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms.

In the compound involved in this embodiment, it is also preferred that at least one of R 21 to R 30 in the general formula (1D-C) that is not a bonding position to the benz[a]anthracene ring in _the general formula (1C-C) and does not form the substituted or _{unsubstituted} monocyclic ring and the substituted or unsubstituted condensed ring is the substituted or unsubstituted phenyl group.

In the compound according to the present embodiment, it is also preferred that the group represented by the general formula (1D-C) is a group represented by the following general formula (1D-C1) or general formula (1D-C3).

【Chemical formula 35】

(In the above general formula (1D-C1),

One or more of the groups consisting of two or more adjacent ones of R ₂₁ to R ₂₉

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₂₁ to R ₂₉ which do not form the above substituted or unsubstituted monocyclic ring and do not form the above substituted or unsubstituted condensed ring are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

* represents the bonding position to the benz[a]anthracene ring in the above general formula (1C-C),

In the above general formula (1D-C3),

One or more of the group consisting of two or more adjacent ones of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ which do not form the above-mentioned substituted or unsubstituted monocyclic ring and do not form the above-mentioned substituted or unsubstituted condensed ring are each independently the same as R ₂₁ to R ₂₉ in the above-mentioned general formula (1D-C1),

* represents the bonding position to the benz[a]anthracene ring in the above general formula (1C-C).

In the compounds involved in the present embodiment, it is also preferred that at least one of R ₂₁ to R ₂₉ in the general formula (1D-C1) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring in the group represented by the general formula (1D-C1) _or the _general formula (1D-C3) is _a group other than _a hydrogen atom.

In the compounds involved in the present embodiment, it is also preferred that at least one of R 21 to R 29 in the general formula (1D-C1) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring in the group represented by the general formula (1D-C1) or the general formula (1D-C3), or at least one of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ in the general formula (1D-C3) is a substituted _or unsubstituted aromatic group _having 6 to 50 ring carbon atoms.

In the compounds involved in the present embodiment, it is also preferred that at least one of R 21 to R 29 in the general formula (1D-C1) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring in the group represented by the general formula (1D-C1) or the general formula (1D-C3) is _a substituted or unsubstituted phenyl group _{, or at least one of R 21 to} R ₂₇ , R ₂₉ and R ₃₀ in the general formula (1D-C3).

In the compound according to the present embodiment, it is also preferred that the group represented by the general formula (1D-C) is a group represented by the general formula (1D-C1).

In the compound according to this embodiment, it is also preferred that one of R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ is a group represented by the above general formula (1D-C).

In the compound according to this embodiment, it is also preferred that one of R ₆ , R ₇ , R ₁₁ and R ₁₂ is a group represented by the above-mentioned general formula (1D-C).

In the compound according to this embodiment, it is also preferred that R ₁₁ is a group represented by the above-mentioned general formula (1D-C).

In the compound according to this embodiment, it is also preferred that R ₁₂ is a group represented by the above-mentioned general formula (1D-C).

In the compound involved in this embodiment, it is also preferred that R ₁₁ is a group represented by the above general formula (1D-C) and R ₁₂ is an unsubstituted phenyl group, or R ₁₂ is a group represented by the above general formula (1D-C) and R ₁₁ is an unsubstituted phenyl group.

In the compound according to this embodiment, it is also preferred that R ₁₁ is a group represented by the above general formula (1D-C), and R ₁₂ is an unsubstituted phenyl group.

In the compound according to this embodiment, it is also preferred that R ₁₂ is a group represented by the above general formula (1D-C), and R ₁₁ is an unsubstituted phenyl group.

The compound according to the present embodiment is also preferably a compound represented by the following general formula (1C-C-1).

The compound according to the present embodiment is also preferably a compound represented by the following general formula (1C-C-2).

【Chemical formula 36】

【Chemical formula 37】

(R ₁ to R ₁₁ in the above general formula (1C-C-1) and R ₁ to R ₁₀ and R ₁₂ in the above general formula (1C-C-2) are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C(=O)R ₈₀₁ ,

-COOR ₈₀₂ ,

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

In the above general formulae (1C-C-1) and (1C-C-2), R ₂₁ to R ₂₉ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

In the compound according to this embodiment, it is also preferred that R ₁₂ is a hydrogen atom.

The compound according to this embodiment also preferably has one or more deuterium atoms in the molecule.

In the compound according to this embodiment, it is also preferred that at least one of R ₁ to R ₃ and R ₉ when they are hydrogen atoms, R ₄ to R ₈ and R ₁₀ to R ₁₂ when they are hydrogen atoms other than the group represented by the general formula (1D-C), and R ₂₁ to R ₃₀ when they are hydrogen atoms is a deuterium atom.

In the compound according to this embodiment, it is also preferred that R ₁ to R ₃ and R ₉ when they are hydrogen atoms, R ₄ to R ₈ and R ₁₀ to R ₁₂ when they are hydrogen atoms other than the group represented by the general formula (1D-C), and R ₂₁ to R ₃₀ when they are hydrogen atoms are all deuterium atoms.

In the compound involved in the present embodiment, it is also preferred that when R ₁ to R ₃ and R ₉ when they are groups other than hydrogen atoms, R ₄ to R ₈ and R ₁₀ to R ₁₂ when they are groups other than hydrogen atoms except the group represented by the above general formula (1D-C), and R ₂₁ to R ₃₀ when they are groups other than hydrogen atoms each have a hydrogen atom, at least one of the hydrogen atoms is a deuterium atom.

In the compound involved in this embodiment, it is also preferred that when R ₁ to R ₃ and R ₉ when they are groups other than hydrogen atoms, R ₄ to R ₈ and R ₁₀ to R ₁₂ when they are groups other than hydrogen atoms except the group represented by the above general formula (1D-C), and R ₂₁ to R ₃₀ when they are groups other than hydrogen atoms each have a hydrogen atom, the hydrogen atom is preferably a deuterium atom.

Among the compounds according to the present embodiment, compounds not containing a heteroatom in the molecule are also preferred.

In the compound according to the present embodiment, it is also preferred that all the groups described as "substituted or unsubstituted" are "unsubstituted" groups, and all the rings described as "substituted or unsubstituted" are "unsubstituted" rings.

·Method for producing the compound according to this embodiment

The compound involved in this embodiment can be produced according to the synthesis method described in the Examples described below. In addition, the compound involved in this embodiment can also be produced by following the synthesis method by using a known substitution reaction and raw materials corresponding to the target substance.

Specific examples of the compounds according to this embodiment

As specific examples of the compounds involved in this embodiment, for example, compounds falling within the scope of the compounds involved in this embodiment among the compounds exemplified in the compound represented by the general formula (1C) as the first compound used in the organic electroluminescent element involved in the fourth embodiment described later are specific examples of the compounds involved in this embodiment.

[Fourth Embodiment]

(Organic electroluminescent element)

The organic EL element according to this embodiment will be described.

The organic EL device according to this embodiment contains the compound according to the first embodiment, the second embodiment, or the third embodiment in one embodiment.

The organic EL element involved in this embodiment has an anode, a cathode and an organic layer disposed between the anode and the cathode in one embodiment. The organic layer includes at least one layer formed by an organic compound. Alternatively, the organic layer is formed by stacking a plurality of layers formed by organic compounds. The organic layer may also include an inorganic compound.

In one aspect of the organic EL device according to the present embodiment, at least one of the organic layers contains the compound according to the first embodiment.

In one aspect of the organic EL device according to the present embodiment, at least one of the organic layers contains the compound according to the second embodiment.

In one aspect of the organic EL device according to the present embodiment, at least one of the organic layers contains the compound according to the third embodiment.

In the organic EL element of the present embodiment, it is preferred that at least one of the organic layers has a light-emitting region. In the organic EL element of the present embodiment, the light-emitting region preferably contains at least one light-emitting layer. In one embodiment, the light-emitting layer contains a compound represented by the above general formula (1C-A). In one embodiment, the light-emitting layer contains a compound represented by the above general formula (1C-B). In one embodiment, the light-emitting layer contains a compound represented by the above general formula (1C-C).

It is also preferred that the organic EL element involved in this embodiment has an anode, a cathode and a light-emitting region arranged between the above-mentioned anode and the above-mentioned cathode, the above-mentioned light-emitting region includes a first light-emitting layer and a second light-emitting layer, the above-mentioned first light-emitting layer contains the compound represented by the above-mentioned general formula (1C-A) as the first compound, and the above-mentioned second light-emitting layer contains the second compound.

In the organic EL device of this embodiment, the compound represented by the general formula (1C-A) and the second compound are different compounds from each other.

It is also preferred that the organic EL element involved in this embodiment has an anode, a cathode and a light-emitting region arranged between the above-mentioned anode and the above-mentioned cathode, the above-mentioned light-emitting region includes a first light-emitting layer and a second light-emitting layer, the above-mentioned first light-emitting layer contains the compound represented by the above-mentioned general formula (1C-B) as the first compound, and the above-mentioned second light-emitting layer contains the second compound.

In the organic EL device of this embodiment, the compound represented by the general formula (1C-B) and the second compound are different compounds from each other.

It is also preferred that the organic EL element involved in the present embodiment has an anode, a cathode and a light-emitting region arranged between the above-mentioned anode and the above-mentioned cathode, the above-mentioned light-emitting region includes a first light-emitting layer and a second light-emitting layer, the above-mentioned first light-emitting layer contains the compound represented by the above-mentioned general formula (1C-C) as the first compound, and the above-mentioned second light-emitting layer contains the second compound.

In the organic EL device of this embodiment, the compound represented by the general formula (1C-C) and the second compound are different compounds from each other.

The organic EL element involved in this embodiment, in one scenario, has an anode, a cathode and an organic layer arranged between the above-mentioned anode and the above-mentioned cathode, the above-mentioned organic layer has a light-emitting region, the above-mentioned light-emitting region includes a first light-emitting layer and a second light-emitting layer, the above-mentioned first light-emitting layer contains a first compound represented by the following general formula (1C), and the above-mentioned second light-emitting layer contains a second compound.

【Chemical formula 38】

(In the above general formula (1C),

One of R ₄ to R ₈ and R ₁₀ to R ₁₂ is a group represented by the above general formula (1D),

R ₁ to R ₃ , R ₉ , and R ₄ to R ₈ and R ₁₀ to R ₁₂ other than the group represented by the above general formula (1D) are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C(=O)R ₈₀₁ ,

-COOR ₈₀₂ ,

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

When R ₁₁ is a group represented by the above general formula (1D), R ₁₂ is a hydrogen atom or a substituted or unsubstituted phenyl group,

When R ₁₂ is a group represented by the above general formula (1D), R ₁₁ is a hydrogen atom or a substituted or unsubstituted phenyl group,

In the above general formula (1D), one of R ₂₁ to R ₃₀ represents a bonding position to the benz[a]anthracene ring in the above general formula (1C), and one or more groups consisting of two or more adjacent ones of R ₂₁ to R ₃₀ in the above general formula (1D) that are not the bonding position are present.

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₂₁ to R 30 in the above general formula (1D) which are not bonded to the benz[a]anthracene ring in the above general formula (1C), do not form the above substituted or unsubstituted monocyclic ring, and do not form the above substituted or _{unsubstituted} condensed ring, are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

In the compound represented by the above general formula (1C), R ₉₀₁ , R ₉₀₂ , R ₉₀₃ , R ₉₀₄ , R ₉₀₅ , R ₉₀₆ , R ₉₀₇ , R ₈₀₁ and R ₈₀₂ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

When there are a plurality of R ₉₀₁ , the plurality of R ₉₀₁ are the same as or different from each other.

When there are multiple R ₉₀₂ , the multiple R ₉₀₂ are the same as or different from each other.

When there are multiple R ₉₀₃ , the multiple R ₉₀₃ are the same as or different from each other.

When there are a plurality of R ₉₀₄ , the plurality of R ₉₀₄ are the same as or different from each other.

When there are multiple R ₉₀₅ , the multiple R ₉₀₅ are the same as or different from each other.

When there are multiple R ₉₀₆ , the multiple R ₉₀₆ are the same as or different from each other.

When there are a plurality of R ₉₀₇ , the plurality of R ₉₀₇ are the same as or different from each other.

When there are multiple _R801 , the multiple _R801 are the same as or different from each other.

When there are multiple R ₈₀₂ , the multiple R ₈₀₂ are the same as or different from each other.)

In the organic electroluminescent element involved in one aspect of the present embodiment, it is also preferred that at least one of R ₂₁ to R ₃₀ in the general formula (1D) which is not a bonding position to the benz[a]anthracene ring in the general formula (1C) and does not form the substituted or unsubstituted monocyclic ring and the substituted or unsubstituted condensed ring is a group other than a hydrogen atom.

In the organic electroluminescent element involved in one aspect of the present embodiment, it is also preferred that at least one of R ₂₁ to R ₃₀ in the general formula (1D) which is not a bonding position to the benz[a]anthracene ring in the general formula (1C) and does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In the organic electroluminescent element involved in one aspect of the present embodiment, it is also preferred that at least one of R ₂₁ to R ₃₀ in the general formula (1D) which is not a bonding position to the benz[a]anthracene ring in the general formula (1C) and does not form the substituted or unsubstituted monocyclic ring and the substituted or unsubstituted condensed ring is a substituted or unsubstituted phenyl group.

In the organic electroluminescent element according to one aspect of the present embodiment, it is also preferred that the group represented by the general formula (1D) is a group represented by the following general formula (1D-1), general formula (1D-2) or general formula (1D-3).

【Chemical formula 39】

(In the above general formula (1D-1),

One or more of the groups consisting of two or more adjacent ones of R ₂₁ to R ₂₉

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₂₁ to R ₂₉ which do not form the above substituted or unsubstituted monocyclic ring and do not form the above substituted or unsubstituted condensed ring are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

* represents the bonding position to the benz[a]anthracene ring in the above general formula (1C),

In the above general formula (1D-2),

One or more of the groups consisting of two or more adjacent ones of R ₂₁ to R ₂₈ and R ₃₀

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₂₁ to R ₂₈ and R ₃₀ which do not form the above-mentioned substituted or unsubstituted monocyclic ring and do not form the above-mentioned substituted or unsubstituted condensed ring are each independently the same as R ₂₁ to R ₂₉ in the above-mentioned general formula (1D-1),

* represents the bonding position to the benz[a]anthracene ring in the above general formula (1C),

In the above general formula (1D-3),

One or more of the group consisting of two or more adjacent ones of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ which do not form the above-mentioned substituted or unsubstituted monocyclic ring and do not form the above-mentioned substituted or unsubstituted condensed ring are each independently the same as R ₂₁ to R ₂₉ in the above-mentioned general formula (1D-1),

* represents the bonding position to the benz[a]anthracene ring in the above general formula (1C).

In the organic electroluminescent element involved in one scheme of the present embodiment, it is also preferred that at least one of R ₂₁ to R ₂₉ in the general formula (1D-1) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, at least one of R ₂₁ to R ₂₈ and R ₃₀ in the general formula (1D-2), or at least one of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ in the general formula (1D-3) is a group other than a hydrogen atom.

In the organic electroluminescent element involved in one scheme of the present embodiment, it is also preferred that at least one of R ₂₁ to R ₂₉ in the general formula (1D-1) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, at least one of R ₂₁ to R ₂₈ and R ₃₀ in the general formula (1D-2), or at least one of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ in the general formula (1D-3) is a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms.

In the organic electroluminescent element involved in one scheme of the present embodiment, it is also preferred that at least one of R ₂₁ to R ₂₉ in the general formula (1D-1) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, at least one of R ₂₁ to R ₂₈ and R ₃₀ in the general formula (1D-2), or at least one of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ in the general formula (1D-3) is a substituted or unsubstituted phenyl group.

In the organic electroluminescent device according to one aspect of the present embodiment, it is also preferred that the group represented by the general formula (1D) is a group represented by the general formula (1D-1).

In the organic electroluminescent device according to one aspect of the present embodiment, it is also preferred that, in the compound represented by the general formula (1C), one of R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ is a group represented by the general formula (1D).

In the organic electroluminescent device according to one aspect of the present embodiment, it is also preferred that, in the compound represented by the general formula (1C), one of R ₆ , R ₇ , R ₁₁ and R ₁₂ is a group represented by the general formula (1D).

In the organic electroluminescent device according to one aspect of the present embodiment, it is also preferred that, in the compound represented by the above general formula (1C), R ₁₁ is a group represented by the above general formula (1D).

In the organic electroluminescent device according to one aspect of the present embodiment, it is also preferred that, in the compound represented by the above general formula (1C), R ₁₂ is a group represented by the above general formula (1D).

In the organic electroluminescent element involved in one scheme of the present embodiment, it is also preferred that, in the compound represented by the above general formula (1C), R ₁₁ is the group represented by the above general formula (1D) and R ₁₂ is an unsubstituted phenyl group, or R ₁₂ is the group represented by the above general formula (1D) and R ₁₁ is an unsubstituted phenyl group.

In the organic electroluminescent device according to one aspect of the present embodiment, it is also preferred that, in the compound represented by the general formula (1C), R ₁₁ is a group represented by the general formula (1D), and R ₁₂ is an unsubstituted phenyl group.

In the organic electroluminescent device according to one aspect of the present embodiment, it is also preferred that, in the compound represented by the general formula (1C), R ₁₂ is a group represented by the general formula (1D), and R ₁₁ is an unsubstituted phenyl group.

In the organic electroluminescent device according to one aspect of the present embodiment, the compound represented by the general formula (1C) is preferably also a compound represented by the following general formula (1C-1).

In the organic electroluminescent device according to one aspect of the present embodiment, the compound represented by the general formula (1C) is preferably a compound represented by the following general formula (1C-2).

【Chemical formula 40】

【Chemical formula 41】

(R ₁ to R ₁₁ in the above general formula (1C-1) and R ₁ to R ₁₀ and R ₁₂ in the above general formula (1C-2) are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C(=O)R ₈₀₁ ,

-COOR ₈₀₂ ,

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

In the above general formulae (1C-1) and (1C-2), R ₂₁ to R ₂₈ and R ₃₀ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

In the organic electroluminescent device according to one aspect of the present embodiment, it is also preferred that, in the compound represented by the general formula (1C), R ₁₂ is a group represented by the general formula (1D), and R ₁₁ is a hydrogen atom.

In the organic electroluminescent device according to one aspect of the present embodiment, it is also preferred that R ₁₂ is a group represented by the above general formula (1D), and R ₁₁ is a substituted or unsubstituted phenyl group.

In the organic electroluminescent device according to one aspect of the present embodiment, it is also preferred that, in the compound represented by the general formula (1C), R ₁ to R ₃ , R ₉ , and R ₄ to R ₈ and R ₁₀ to R ₁₂ other than the group represented by the general formula (1D) are each independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In the organic electroluminescent element involved in one aspect of the present embodiment, it is also preferred that R 21 to R ₃₀ in the general formula (1D) which are not bonded to the benz[a]anthracene ring in the general formula (1C) and do not form the substituted or unsubstituted monocyclic ring and the substituted or unsubstituted condensed ring are each independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to ₅₀ ring carbon atoms.

The organic electroluminescent device according to one aspect of the present embodiment is also preferably a compound containing no hetero atom in the molecule.

In the organic electroluminescent device according to one aspect of the present embodiment, it is also preferred that the groups described as "substituted or unsubstituted" are all "unsubstituted" groups, and the rings described as "substituted or unsubstituted" are all "unsubstituted" rings.

In the organic electroluminescent device according to one aspect of the present embodiment, it is also preferred that R ₁₂ in the compound represented by the general formula (1C) is a hydrogen atom.

In the organic electroluminescent device according to one aspect of the present embodiment, it is also preferred that the compound represented by the general formula (1C) has one or more deuterium atoms in the molecule.

In the organic electroluminescent device according to one aspect of the present embodiment, it is also preferred that, in the compound represented by the general formula (1C), at least one of R ₁ to R ₃ and R ₉ when they are hydrogen atoms, R ₄ to R ₈ and R ₁₀ to R ₁₂ which are hydrogen atoms other than the group represented by the general formula (1D), and R ₂₁ to R ₃₀ when they are hydrogen atoms is a deuterium atom.

In the organic electroluminescent device according to one aspect of the present embodiment, it is also preferred that, in the compound represented by the general formula (1C), R ₁ to R ₃ and R ₉ when they are hydrogen atoms, R ₄ to R ₈ and R ₁₀ to R ₁₂ which are hydrogen atoms other than the group represented by the general formula (1D), and R ₂₁ to R ₃₀ when they are hydrogen atoms are all deuterium atoms.

In the organic electroluminescent device according to one aspect of the present embodiment, it is also preferred that, in the compound represented by the general formula (1C), when R ₁ to R ₃ and R ₉ when they are groups other than hydrogen atoms, R ₄ to R ₈ and R ₁₀ to R ₁₂ which are groups other than hydrogen atoms except the group represented by the general formula (1D), and R ₂₁ to R ₃₀ when they are groups other than hydrogen atoms each have a hydrogen atom, at least one of the hydrogen atoms is a deuterium atom.

In the organic electroluminescent device according to one aspect of the present embodiment, it is also preferred that, in the compound represented by the general formula (1C), when R ₁ to R ₃ and R ₉ when they are groups other than hydrogen atoms, R ₄ to R ₈ and R ₁₀ to R ₁₂ which are groups other than hydrogen atoms except the group represented by the general formula (1D), and R ₂₁ to R ₃₀ when they are groups other than hydrogen atoms each have a hydrogen atom, the hydrogen atom is preferably a deuterium atom.

In the organic electroluminescent device according to one aspect of this embodiment, R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₀ , R ₁₁ or R ₁₂ in the compound represented by the general formula (1C) is a group represented by the general formula (1D).

In the organic electroluminescent device according to one aspect of this embodiment, R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₀ , R ₁₁ or R ₁₂ in the compound represented by the general formula (1C-A) is a group represented by the general formula (1D-A).

In the organic electroluminescent device according to one aspect of this embodiment, R ₄ , R ₅ , R ₆ , R ₈ , R ₁₀ , R ₁₁ or R ₁₂ in the compound represented by the general formula (1C-B) is a group represented by the general formula (1D-B).

In the organic electroluminescent device according to one aspect of this embodiment, R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₀ , R ₁₁ or R ₁₂ in the compound represented by the general formula (1C-C) is a group represented by the general formula (1D-C).

When R ₄ , R ₅ , R ₆ , R ₇ , R ₈ , R ₁₀ , R ₁₁ or R ₁₂ which is a position with a higher electron density of HOMO and LUMO or a position with a smaller singlet energy S1 is any one group selected from the group represented by the above general formula (1D), the group represented by the above general formula (1D-A) and the group represented by the above general formula (1D-C), the excitation resistance is easily improved and the life of the organic EL element is easily extended.

When R ₄ , R ₅ , R ₆ , R ₈ , R ₁₀ , R ₁₁ or R ₁₂ , which is a position with higher electron density of HOMO and LUMO or a site with smaller singlet energy S1, is a group represented by the above general formula (1D-B), excitation resistance is easily improved and the life of the organic EL element is easily prolonged.

In the case where the first compound used in the first light-emitting layer has a structure in which the group represented by the general formula (1D), the group represented by the general formula (1D-A), the group represented by the general formula (1D-B) or the group represented by the general formula (1D-C) is directly connected to the benzo[a]anthracene ring, it is believed that the triplet energy _T1 is distributed on both the benzo[a]anthracene ring and the pyrene skeleton in the group represented by the general formula (1D), the group represented by the general formula (1D-A), the group represented by the general formula (1D-B) and the group represented by the general formula (1D-C), thereby extending the life.

·Method for producing a compound represented by general formula (1C)

The compound represented by the general formula (1C) can be prepared by the synthesis method described in the Examples below. Alternatively, the compound represented by the general formula (1C) can also be prepared by following the synthesis method using known substitution reactions and raw materials corresponding to the target substance.

Specific examples of compounds represented by general formula (1C)

Specific examples of the compound represented by the general formula (1C) include the following compounds. However, the present invention is not limited to these specific examples. In this specification, a deuterium atom is marked as D in a chemical formula, and a protium atom is marked as H or omitted.

【Chemical formula 42】

【Chemical formula 43】

【Chemical formula 44】

【Chemical formula 45】

【Chemical formula 46】

【Chemical formula 47】

【Chemical formula 48】

【Chemical formula 49】

【Chemical formula 50】

【Chemical formula 51】

【Chemical formula 52】

【Chemical formula 53】

【Chemical formula 54】

【Chemical formula 55】

【Chemical formula 56】

【Chemical formula 57】

【Chemical formula 58】

【Chemical formula 59】

【Chemical formula 60】

【Chemical formula 61】

【Chemical formula 62】

【Chemical formula 63】

【Chemical formula 64】

When the light-emitting region includes a first light-emitting layer and a second light-emitting layer, the organic EL element involved in this embodiment may, for example, have an anode, a first light-emitting layer, a second light-emitting layer and a cathode in sequence, or the order of the first light-emitting layer and the second light-emitting layer may be reversed and the anode, the second light-emitting layer, the first light-emitting layer and the cathode may be sequentially provided.

When the light-emitting region includes the first light-emitting layer and the second light-emitting layer, the organic EL element according to this embodiment preferably includes the second light-emitting layer between the anode and the cathode, and the first light-emitting layer is arranged between the anode and the second light-emitting layer.

When the light-emitting region includes a first light-emitting layer and a second light-emitting layer, the organic EL element according to this embodiment preferably includes the first light-emitting layer between the anode and the cathode, and the second light-emitting layer is arranged between the anode and the first light-emitting layer.

(Light emission wavelength of organic EL element)

The organic EL element according to the present embodiment preferably emits light having a maximum peak wavelength of 500 nm or less, and more preferably emits light having a wavelength of 430 nm to 480 nm or less, when the element is driven.

The maximum peak wavelength of light emitted by the organic EL element when the element is driven is determined as follows. The spectral emission brightness spectrum when a voltage is applied to the organic EL element so that the current density reaches 10 mA/ ^cm2 is measured using a spectral emission brightness meter CS-2000 (manufactured by Konica Minolta). In the obtained spectral emission brightness spectrum, the peak wavelength of the luminescence spectrum with the maximum luminous intensity is measured and taken as the maximum peak wavelength (unit: nm).

The method for determining the maximum peak wavelength of a compound in this specification is as follows. A toluene solution of 10 ^-6 mol/L or more and 10 ^-5 mol/L or less of the compound to be determined is prepared and added to a quartz colorimetric cell, and the luminescence spectrum of the sample is measured at room temperature (300K) (the vertical axis is set as luminescence intensity, and the horizontal axis is set as wavelength). The luminescence spectrum can be measured by a spectrofluorophotometer (device name: F-7000) manufactured by Hitachi High-Tech Scientific Co., Ltd. It should be noted that the luminescence spectrum measuring device is not limited to the device used here.

In the emission spectrum, the peak wavelength of the emission spectrum with the maximum emission intensity is referred to as the maximum emission peak wavelength. It should be noted that in this specification, the maximum peak wavelength may be referred to as the fluorescence emission maximum peak wavelength (FL-peak).

In the organic EL element involved in this embodiment, the organic layer can be composed only of a light-emitting layer, and as an organic layer, it can also have at least one layer selected from a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole blocking layer and an electron blocking layer.

In the organic EL element according to this embodiment, it is preferred that a hole transport layer be provided between the anode and the light emitting region.

In the organic EL element involved in the present embodiment, when the light-emitting region includes the first light-emitting layer and the second light-emitting layer and the stacking order of the first light-emitting layer and the second light-emitting layer is the order of the first light-emitting layer and the second light-emitting layer from the anode side, it is preferred that a hole transport layer be provided between the anode and the first light-emitting layer. In addition, when the stacking order of the first light-emitting layer and the second light-emitting layer is the order of the second light-emitting layer and the first light-emitting layer from the anode side, it is preferred that a hole transport layer be provided between the anode and the second light-emitting layer.

In the organic EL device according to this embodiment, it is preferable to have an electron transport layer between the cathode and the light emitting region.

In the organic EL element involved in the present embodiment, when the light-emitting region includes the first light-emitting layer and the second light-emitting layer and the stacking order of the first light-emitting layer and the second light-emitting layer is the order of the first light-emitting layer and the second light-emitting layer from the anode side, it is preferred that an electron transport layer be provided between the cathode and the second light-emitting layer. In addition, when the stacking order of the first light-emitting layer and the second light-emitting layer is the order of the second light-emitting layer and the first light-emitting layer from the anode side, it is preferred that an electron transport layer be provided between the cathode and the first light-emitting layer.

FIG. 1 schematically shows a configuration of an example of an organic EL element according to the present embodiment.

The organic EL element 1A shown in FIG1 includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10A disposed between the anode 3 and the cathode 4. The organic layer 10A includes a hole transport region 6, a light emitting region 5A, and an electron transport region 7 in order from the anode 3 side. The hole transport region 6 includes a hole injection layer 61 and a hole transport layer 62 in order from the anode 3 side. The light emitting region 5A includes one light emitting layer 5. The electron transport region 7 includes an electron transport layer 71 and an electron injection layer 72 in order from the light emitting region 5A side.

(Luminous layer)

The light-emitting layer 5 contains the compound according to the first embodiment, the compound according to the second embodiment, or the compound according to the third embodiment.

In the organic EL device 1A, the compound contained in the light-emitting layer 5 is preferably a compound represented by the above-mentioned general formula (1C-A).

In the organic EL device 1A, the compound contained in the light-emitting layer 5 is also preferably a compound represented by the above-mentioned general formula (1C-B).

In the organic EL device 1A, the compound contained in the light-emitting layer 5 is also preferably a compound represented by the above-mentioned general formula (1C-C).

(Luminescent Compound)

In the organic EL device 1A, the light-emitting layer 5 also preferably further contains a light-emitting compound (preferably a fluorescent compound).

The luminescent compound contained in the luminescent layer 5 can be selected from

The compound represented by the following general formula (3),

The compound represented by the following general formula (4),

The compound represented by the following general formula (5),

The compound represented by the following general formula (6),

The compound represented by the following general formula (7),

The compound represented by the following general formula (8),

The compound represented by the following general formula (9), and

One or more compounds represented by the following general formula (10).

(Compound represented by general formula (3))

The compound represented by the general formula (3) will be described.

【Chemical formula 65】

(In the above general formula (3),

One or more of a group consisting of two or more adjacent ones of R ₃₀₁ to R ₃₁₀

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

At least one of R ₃₀₁ to R ₃₁₀ is a monovalent group represented by the following general formula (31),

R ₃₀₁ to R ₃₁₀ which do not form the above-mentioned monocyclic ring, do not form the above-mentioned condensed ring and are not the monovalent group represented by the following general formula (31) are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

【Chemical formula 66】

(In the above general formula (31),

Ar ₃₀₁ and Ar ₃₀₂ are each independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

L ₃₀₁ ～L ₃₀₃ are each independently

single bond,

a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms,

* represents the bonding position in the pyrene ring in the above general formula (3).

In the luminescent compound, R ₉₀₁ , R ₉₀₂ , R ₉₀₃ , R ₉₀₄ , R ₉₀₅ , R ₉₀₆ and R ₉₀₇ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

Preferably, it is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

When there are a plurality of R ₉₀₁ , the plurality of R ₉₀₁ are the same as or different from each other.

When there are multiple R ₉₀₂ , the multiple R ₉₀₂ are the same as or different from each other.

When there are multiple R ₉₀₃ , the multiple R ₉₀₃ are the same as or different from each other.

When there are a plurality of R ₉₀₄ , the plurality of R ₉₀₄ are the same as or different from each other.

When there are multiple R ₉₀₅ , the multiple R ₉₀₅ are the same as or different from each other.

When there are multiple R ₉₀₆ , the multiple R ₉₀₆ are the same as or different from each other.

When there are a plurality of R ₉₀₇ , the plurality of R _{907 s} may be the same as or different from each other.

In the above general formula (3), it is preferred that two of R ₃₀₁ to R ₃₁₀ are groups represented by the above general formula (31).

In one embodiment, the compound represented by the general formula (3) is a compound represented by the following general formula (33).

【Chemical formula 67】

(In the above general formula (33),

R ₃₁₁ to R ₃₁₈ are each independently the same as R ₃₀₁ to R ₃₁₀ in the above general formula (3) which are not monovalent groups represented by the above general formula (31),

L ₃₁₁ ～L ₃₁₆ are each independently

single bond,

a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms,

Ar ₃₁₂ , Ar ₃₁₃ , Ar ₃₁₅ and Ar ₃₁₆ are each independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

In the above general formula (31), L ₃₀₁ is preferably a single bond, and L ₃₀₂ and L ₃₀₃ are preferably single bonds.

In one embodiment, the compound represented by the general formula (3) is represented by the following general formula (34) or (35).

【Chemical formula 68】

(In the above general formula (34),

R ₃₁₁ to R ₃₁₈ are each independently the same as R ₃₀₁ to R ₃₁₀ in the above general formula (3) which are not monovalent groups represented by the above general formula (31),

L ₃₁₂ , L ₃₁₃ , L ₃₁₅ and L ₃₁₆ are each independently the same as L ₃₁₂ , L ₃₁₃ , L ₃₁₅ and L ₃₁₆ in the above general formula (33).

Ar ₃₁₂ , Ar ₃₁₃ , Ar ₃₁₅ and Ar ₃₁₆ are independently the same as Ar ₃₁₂ , Ar ₃₁₃ , Ar ₃₁₅ and Ar ₃₁₆ in the above general formula (33).

【Chemical formula 69】

(In the above general formula (35),

R ₃₁₁ to R ₃₁₈ are each independently the same as R ₃₀₁ to R ₃₁₀ in the above general formula (3) which are not monovalent groups represented by the above general formula (31),

Ar ₃₁₂ , Ar ₃₁₃ , Ar ₃₁₅ and Ar ₃₁₆ are independently the same as Ar ₃₁₂ , Ar ₃₁₃ , Ar ₃₁₅ and Ar ₃₁₆ in the above general formula (33).

In the above general formula (31), at least one of Ar ₃₀₁ and Ar ₃₀₂ is preferably a group represented by the following general formula (36).

In the above-mentioned general formulae (33) to (35), it is preferred that at least one of Ar ₃₁₂ and Ar ₃₁₃ is a group represented by the following general formula (36).

In the above-mentioned general formulae (33) to (35), it is preferred that at least one of Ar ₃₁₅ and Ar ₃₁₆ is a group represented by the following general formula (36).

【Chemical formula 70】

(In the above general formula (36),

X ₃ represents an oxygen atom or a sulfur atom,

One or more of the groups consisting of two or more adjacent ones of R ₃₂₁ to R ₃₂₇

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₃₂₁ to R ₃₂₇ which do not form the above-mentioned monocyclic ring and do not form the above-mentioned condensed ring are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

* indicates the bonding position with L ₃₀₂ , L ₃₀₃ , L ₃₁₂ , L ₃₁₃ , L ₃₁₅ or L _316. )

_X3 is preferably an oxygen atom.

Preferably, at least one of R ₃₂₁ to R ₃₂₇ is

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

In the above general formula (31), it is preferred that Ar ₃₀₁ is a group represented by the above general formula (36), and Ar ₃₀₂ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In the above general formulae (33) to (35), it is preferred that Ar ₃₁₂ is a group represented by the above general formula (36), and Ar ₃₁₃ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In the above general formulae (33) to (35), it is preferred that Ar ₃₁₅ is a group represented by the above general formula (36), and Ar ₃₁₆ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, the compound represented by the above general formula (3) is represented by the following general formula (37).

【Chemical formula 71】

(In the above general formula (37),

R ₃₁₁ to R ₃₁₈ are each independently the same as R ₃₀₁ to R ₃₁₀ in the above general formula (3) which are not monovalent groups represented by the above general formula (31),

One or more of the groups consisting of two or more adjacent ones of R ₃₂₁ to R ₃₂₇

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

One or more of the group consisting of two or more adjacent ones of R ₃₄₁ to R ₃₄₇

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₃₂₁ to R ₃₂₇ and R ₃₄₁ to R ₃₄₇ which do not form the above-mentioned monocyclic ring and do not form the above-mentioned condensed ring are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

R ₃₃₁ to R ₃₃₅ and R ₃₅₁ to R ₃₅₅ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms, cyano, nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

As specific examples of the compound represented by the general formula (3), for example, the following compounds can be mentioned.

【Chemical formula 72】

【Chemical formula 73】

【Chemical formula 74】

【Chemical formula 75】

【Chemical formula 76】

(Compound represented by general formula (4))

The compound represented by the general formula (4) will be described.

【Chemical formula 77】

(In the above general formula (4),

Z is independently CRa or a nitrogen atom,

Ring A1 and ring A2 are each independently

A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms,

When there are multiple Ra, one or more groups of two or more adjacent Ra are included.

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

n21 and n22 are each independently 0, 1, 2, 3 or 4,

When there are multiple Rb, one or more groups of two or more adjacent Rb

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

When there are multiple Rc, one or more groups of two or more adjacent Rc

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

Ra, Rb and Rc which do not form the above-mentioned monocyclic ring and do not form the above-mentioned condensed ring are each independently

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

The "aromatic hydrocarbon ring" of the A1 ring and the A2 ring has the same structure as the compound obtained by introducing a hydrogen atom into the above-mentioned "aryl group".

The "aromatic hydrocarbon ring" of the A1 ring and the A2 ring contains two carbon atoms in the condensed bicyclic structure at the center of the above general formula (4) as ring-constituting atoms.

Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms" include compounds obtained by introducing a hydrogen atom into the "aryl group" described in Specific Example Group G1.

The "heterocycle" of the A1 ring and the A2 ring has the same structure as the compound obtained by introducing a hydrogen atom into the above-mentioned "heterocyclic group".

The "heterocycle" of the A1 ring and the A2 ring contains two carbon atoms in the central condensed bicyclic structure of the above general formula (4) as ring-constituting atoms.

Specific examples of the "substituted or unsubstituted heterocycle having 5 to 50 ring atoms" include compounds in which a hydrogen atom is introduced into the "heterocyclic group" described in Specific Example Group G2.

Rb is bonded to any of the carbon atoms forming the aromatic hydrocarbon ring as the A1 ring, or is bonded to any of the atoms forming the heterocyclic ring as the A1 ring.

Rc is bonded to any of the carbon atoms forming the aromatic hydrocarbon ring as the A2 ring, or is bonded to any of the atoms forming the heterocyclic ring as the A2 ring.

Among Ra, Rb and Rc, at least one is preferably a group represented by the following general formula (4a), and at least two are more preferably groups represented by the following general formula (4a).

【Chemical formula 78】

*-L ₄₀₁ -Ar ₄₀₁ (4a)

(In the above general formula (4a),

L ₄₀₁

single bond,

a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms,

Ar ₄₀₁

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or

A group represented by the following general formula (4b).

【Chemical formula 79】

(In the above general formula (4b),

_L402 and _L403 are each independently

single bond,

a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or

a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms,

Composed of Ar ₄₀₂ and Ar ₄₀₃

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

Ar ₄₀₂ and Ar ₄₀₃ which do not form the above-mentioned monocyclic ring and do not form the above-mentioned condensed ring are each independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

In one embodiment, the compound represented by the general formula (4) is represented by the following general formula (42).

【Chemical formula 80】

(In the above general formula (42),

One or more of a group consisting of two or more adjacent ones of R ₄₀₁ to R ₄₁₁

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₄₀₁ to R ₄₁₁ which do not form the above-mentioned monocyclic ring and do not form the above-mentioned condensed ring are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

Among R ₄₀₁ to R ₄₁₁ , at least one is preferably a group represented by the above general formula (4a), and at least two are more preferably groups represented by the above general formula (4a).

It is preferred that R ₄₀₄ and R ₄₁₁ are groups represented by the above-mentioned general formula (4a).

In one embodiment, the compound represented by the general formula (4) is a compound in which the structure represented by the following general formula (4-1) or (4-2) is bonded to the A1 ring.

In one embodiment, the compound represented by the general formula (42) is a compound in which a structure represented by the following general formula (4-1) or (4-2) is bonded to the ring to which R ₄₀₄ to R ₄₀₇ are bonded.

【Chemical formula 81】

(In the above general formula (4-1), the two * are each independently bonded to a ring-constituting carbon atom of the aromatic hydrocarbon ring or a ring-constituting atom of the heterocyclic ring as the A1 ring in the above general formula (4), or to any one of R ₄₀₄ to R ₄₀₇ in the above general formula (42),

The three * in the general formula (4-2) are each independently bonded to a ring-constituting carbon atom of the aromatic hydrocarbon ring or a ring-constituting atom of the heterocyclic ring as the A1 ring in the general formula (4), or to any one of R ₄₀₄ to R ₄₀₇ in the general formula (42),

One or more of a group consisting of two or more adjacent ones of R ₄₂₁ to R ₄₂₇

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

One or more of a group consisting of two or more adjacent ones of R ₄₃₁ to R ₄₃₈

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₄₂₁ to R ₄₂₇ and R ₄₃₁ to R ₄₃₈ which do not form the above-mentioned monocyclic ring and do not form the above-mentioned condensed ring are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

In one embodiment, the compound represented by the general formula (4) is a compound represented by the following general formula (41-3), general formula (41-4) or general formula (41-5).

【Chemical formula 82】

【Chemical formula 83】

【Chemical formula 84】

(In the above general formula (41-3), general formula (41-4) and general formula (41-5),

The A1 ring has the same definition as in the above general formula (4),

R ₄₂₁ to R ₄₂₇ are each independently the same as R ₄₂₁ to R ₄₂₇ in the above general formula (4-1),

R ₄₄₀ to R ₄₄₈ are each independently the same as R ₄₀₁ to R ₄₁₁ in the above general formula (42).

In one embodiment, the substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms as the A1 ring of the general formula (41-5) is

A substituted or unsubstituted naphthalene ring, or

A substituted or unsubstituted fluorene ring.

In one embodiment, the substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms as the A1 ring of the general formula (41-5) is

a substituted or unsubstituted dibenzofuran ring,

A substituted or unsubstituted carbazole ring, or

A substituted or unsubstituted dibenzothiophene ring.

In one embodiment, the compound represented by the general formula (4) or the general formula (42) is selected from the group consisting of compounds represented by the following general formulas (461) to (467).

【Chemical formula 85】

【Chemical formula 86】

【Chemical formula 87】

【Chemical formula 88】

【Chemical formula 89】

(In the above general formula (461), general formula (462), general formula (463), general formula (464), general formula (465), general formula (466) and general formula (467),

R ₄₂₁ to R ₄₂₇ are each independently the same as R ₄₂₁ to R ₄₂₇ in the above general formula (4-1),

R ₄₃₁ to R ₄₃₈ are each independently the same as R ₄₃₁ to R ₄₃₈ in the above general formula (4-2),

R ₄₄₀ to R ₄₄₈ and R ₄₅₁ to R ₄₅₄ are each independently the same as R ₄₀₁ to R ₄₁₁ in the above general formula (42),

_X4 is an oxygen atom, _NR801 , or C( _R802 )( _R803 ),

R ₈₀₁ , R ₈₀₂ and R ₈₀₃ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

Preferably, it is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

When there are multiple _R801 , the multiple _R801 are the same as or different from each other.

When there are multiple R ₈₀₂ , the multiple R ₈₀₂ are the same as or different from each other.

When there are multiple _R803 , the multiple _R803 are the same as or different from each other.)

In one embodiment, in the compound represented by the above general formula (42), one or more groups consisting of two or more adjacent groups among R ₄₀₁ to R ₄₁₁ are bonded to each other to form a substituted or unsubstituted monocyclic ring, or are bonded to each other to form a substituted or unsubstituted condensed ring. This embodiment is described in detail in the form of a compound represented by the following general formula (45).

(Compound represented by general formula (45))

The compound represented by the general formula (45) is described.

【Chemical formula 90】

(In the above general formula (45),

Two or more groups selected from the group consisting of _R461 and _R462 , the group consisting of _R462 and _R463 , the group consisting of _R464 and _R465 , the group consisting of _R465 and _R466 , the group consisting of _R466 and _R467 , the group consisting of _R468 and _R469 , the group consisting of _R469 and _R470 , and the group consisting of _R470 and _R471 are bonded to each other to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed ring,

in,

The group consisting of R ₄₆₁ and R ₄₆₂ and the group consisting of R ₄₆₂ and R ₄₆₃ do not simultaneously form a ring;

The group consisting of R ₄₆₄ and R ₄₆₅ and the group consisting of R ₄₆₅ and R ₄₆₆ do not simultaneously form a ring;

The group consisting of R ₄₆₅ and R ₄₆₆ and the group consisting of R ₄₆₆ and R ₄₆₇ do not simultaneously form a ring;

The group consisting of R ₄₆₈ and R ₄₆₉ and the group consisting of R ₄₆₉ and R ₄₇₀ do not simultaneously form a ring; and

The group consisting of R ₄₆₉ and R ₄₇₀ and the group consisting of R ₄₇₀ and R ₄₇₁ do not simultaneously form a ring,

Two or more rings formed by R ₄₆₁ to R ₄₇₁ are identical to or different from each other,

R ₄₆₁ to R ₄₇₁ which do not form the above-mentioned monocyclic ring and do not form the above-mentioned condensed ring are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

In the above general formula (45), _Rn and Rn ₊₁ (n represents an integer selected from 461, 462, 464 to 466 and 468 to 470) are bonded to each other to form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed ring together with the two ring carbon atoms to which _Rn and Rn ₊₁ are bonded. The ring is preferably composed of atoms selected from carbon atoms, oxygen atoms, sulfur atoms and nitrogen atoms, and the number of atoms in the ring is preferably 3 to 7, more preferably 5 or 6.

The number of the above-mentioned ring structures in the compound represented by the general formula (45) is, for example, 2, 3 or 4. The two or more ring structures may each be present on the same benzene ring on the mother skeleton of the general formula (45), or may be present on different benzene rings. For example, when there are three ring structures, one ring structure may be present on each of the three benzene rings of the general formula (45).

Examples of the ring structure in the compound represented by the general formula (45) include structures represented by the following general formulae (451) to (460).

【Chemical formula 91】

(In the above general formulas (451) to (457),

*1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14 represent the two ring-forming carbon atoms to which R _n and R _n+1 are bonded, respectively.

The ring-forming carbon atom to which R _n is bonded may be any one of the two ring-forming carbon atoms represented by *1 and *2, *3 and *4, *5 and *6, *7 and *8, *9 and *10, *11 and *12, and *13 and *14.

_X45 is C( _R4512 )( _R4513 ), _NR4514 , an oxygen atom or a sulfur atom,

One or more of the group consisting of two or more adjacent ones of _R4501 to _R4506 and _R4512 to _R4513

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₄₅₀₁ to R ₄₅₁₄ which do not form the above-mentioned monocyclic ring and do not form the above-mentioned condensed ring are each independently the same as R ₄₆₁ to R ₄₇₁ in the above-mentioned general formula (45).

【Chemical formula 92】

(In the above general formulas (458) to (460),

*1 and *2 as well as *3 and *4 represent the two ring-forming carbon atoms to which R _n and R _n+1 are bonded, respectively.

The ring-forming carbon atom to which R _n is bonded may be any one of the two ring-forming carbon atoms represented by *1 and *2 or *3 and *4.

_X45 is C( _R4512 )( _R4513 ), _NR4514 , an oxygen atom or a sulfur atom,

One or more of the group consisting of two or more adjacent ones of _R4512 to _R4513 and _R4515 to _R4525

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₄₅₁₂ to R ₄₅₁₃ , R ₄₅₁₅ to R ₄₅₂₁ and R ₄₅₂₂ to R ₄₅₂₅ , and R ₄₅₁₄ which do not form the above-mentioned monocyclic ring and do not form the above-mentioned condensed ring are each independently the same as R ₄₆₁ to R ₄₇₁ in the above-mentioned general formula (45).

In the above general formula (45), at least one of R ₄₆₂ , R ₄₆₄ , R ₄₆₅ , R ₄₇₀ and R ₄₇₁ (preferably at least one of R ₄₆₂ , R ₄₆₅ and R ₄₇₀ , more preferably R ₄₆₂ ) is preferably a group that does not form a ring structure.

(i) in the above general formula (45), when the ring structure formed by R _n and R _n+1 has a substituent,

(ii) R ₄₆₁ to R ₄₇₁ in the above general formula (45) which do not form a ring structure and

(iii) In the above general formulae (451) to (460), R ₄₅₀₁ to R ₄₅₁₄ and R ₄₅₁₅ to R ₄₅₂₅ are each independently preferably

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-N(R ₉₀₆ )(R ₉₀₇ ),

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or

Any group selected from the group consisting of groups represented by the following general formulae (461) to (464).

【Chemical formula 93】

(In the above general formulas (461) to (464),

R _d is independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

_X46 is C( _R801 )( _R802 ), _NR803 , an oxygen atom or a sulfur atom,

R ₈₀₁ , R ₈₀₂ and R ₈₀₃ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

Preferably, it is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

When there are multiple _R801 , the multiple _R801 are the same as or different from each other.

When there are multiple R ₈₀₂ , the multiple R ₈₀₂ are the same as or different from each other.

When there are multiple R ₈₀₃ , the multiple R ₈₀₃ are the same as or different from each other.

p1 is 5,

p2 is 4,

p3 is 3,

p4 is 7,

In the above general formulae (461) to (464), * each independently represents a bonding position to the ring structure.

In the light-emitting compound, R ₉₀₁ to R ₉₀₇ are the same as defined above.

In one embodiment, the compound represented by the general formula (45) is represented by any one of the following general formulae (45-1) to (45-6).

【Chemical formula 94】

【Chemical formula 95】

(In the above general formulas (45-1) to (45-6),

Rings d to i are each independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed ring,

R ₄₆₁ to R ₄₇₁ are each independently the same as R ₄₆₁ to R ₄₇₁ in the above general formula (45).

In one embodiment, the compound represented by the general formula (45) is represented by any one of the following general formulae (45-7) to (45-12).

【Chemical formula 96】

【Chemical formula 97】

(In the above general formulas (45-7) to (45-12),

Rings d to f, k, and j are each independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed ring,

R ₄₆₁ to R ₄₇₁ are each independently the same as R ₄₆₁ to R ₄₇₁ in the above general formula (45).

In one embodiment, the compound represented by the general formula (45) is represented by any one of the following general formulae (45-13) to (45-21).

【Chemical formula 98】

【Chemical formula 99】

【Chemical Formula 100】

(In the above general formulas (45-13) to (45-21),

Rings d to k are each independently a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed ring,

R ₄₆₁ to R ₄₇₁ are each independently the same as R ₄₆₁ to R ₄₇₁ in the above general formula (45).

When the ring g or the ring h further has a substituent, examples of the substituent include:

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

The group represented by the above general formula (461),

The group represented by the above general formula (463), or

The group represented by the above general formula (464).

In one embodiment, the compound represented by the general formula (45) is represented by any one of the following general formulae (45-22) to (45-25).

【Chemical Formula 101】

(In the above general formulas (45-22) to (45-25),

_X46 and _X47 are each independently C( _R801 )( _R802 ), _NR803 , an oxygen atom or a sulfur atom,

R ₄₆₁ to R ₄₇₁ and R ₄₈₁ to R ₄₈₈ each independently have the same meanings as R ₄₆₁ to R ₄₇₁ in the above general formula (45).

R ₈₀₁ , R ₈₀₂ and R ₈₀₃ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

Preferably, it is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

When there are multiple _R801 , the multiple _R801 are the same as or different from each other.

When there are multiple R ₈₀₂ , the multiple R ₈₀₂ are the same as or different from each other.

When there are multiple _R803 , the multiple _R803 are the same as or different from each other.)

In one embodiment, the compound represented by the above general formula (45) is represented by the following general formula (45-26).

【Chemical Formula 102】

(In the above general formula (45-26),

_X46 is C( _R801 )( _R802 ), _NR803 , an oxygen atom or a sulfur atom,

R ₄₆₃ , R ₄₆₄ , R ₄₆₇ , R ₄₆₈ , R ₄₇₁ and R ₄₈₁ to R ₄₉₂ are each independently the same as R ₄₆₁ to R ₄₇₁ in the above general formula (45).

R ₈₀₁ , R ₈₀₂ and R ₈₀₃ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

Preferably, it is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

When there are multiple _R801 , the multiple _R801 are the same as or different from each other.

When there are multiple R ₈₀₂ , the multiple R ₈₀₂ are the same as or different from each other.

When there are multiple _R803 , the multiple _R803 are the same as or different from each other.)

As specific examples of the compound represented by the general formula (4), for example, the following compounds can be given: In the following specific examples, Ph represents a phenyl group, and D represents a deuterium atom.

【Chemical Formula 103】

【Chemical Formula 104】

【Chemical Formula 105】

【Chemical formula 106】

【Chemical formula 107】

【Chemical formula 108】

【Chemical formula 109】

【Chemical Formula 110】

【Chemical Formula 111】

【Chemical Formula 112】

(Compound represented by general formula (5))

The compound represented by the general formula (5) is described below. The compound represented by the general formula (5) corresponds to the compound represented by the general formula (41-3) described above.

【Chemical formula 113】

(In the above general formula (5),

One or more of the group consisting of two or more adjacent ones of R ₅₀₁ to R ₅₀₇ and R ₅₁₁ to R ₅₁₇

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₅₀₁ to R ₅₀₇ and R ₅₁₁ to R ₅₁₇ which do not form the above-mentioned monocyclic ring and do not form the above-mentioned condensed ring are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

R ₅₂₁ and R ₅₂₂ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

“One of the groups consisting of two or more adjacent groups of R ₅₀₁ to R ₅₀₇ and R ₅₁₁ to R ₅₁₇ ” includes, for example, the group consisting of R ₅₀₁ and R ₅₀₂ , the group consisting of R ₅₀₂ and R ₅₀₃ , the group consisting of R ₅₀₃ and R ₅₀₄ , the group consisting of R ₅₀₅ and R ₅₀₆ , the group consisting of R ₅₀₆ and R ₅₀₇ , the group consisting of R ₅₀₁ , R ₅₀₂ and R ₅₀₃ , and the like.

In one embodiment, at least one, preferably two, of R ₅₀₁ to R ₅₀₇ and R ₅₁₁ to R ₅₁₇ are a group represented by -N(R ₉₀₆ )(R ₉₀₇ ).

In one embodiment, R ₅₀₁ to R ₅₀₇ and R ₅₁₁ to R ₅₁₇ are each independently

Hydrogen atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

In one embodiment, the compound represented by the general formula (5) is a compound represented by the following general formula (52).

【Chemical formula 114】

(In the above general formula (52),

One or more of the group consisting of two or more adjacent ones of R ₅₃₁ to R ₅₃₄ and R ₅₄₁ to R ₅₄₄

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₅₃₁ to R ₅₃₄ , R ₅₄₁ to R ₅₄₄ , and R ₅₅₁ and R ₅₅₂ which do not form the above-mentioned monocyclic ring and do not form the above-mentioned condensed ring are each independently

Hydrogen atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

R ₅₆₁ to R ₅₆₄ are each independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

In one embodiment, the compound represented by the general formula (5) is a compound represented by the following general formula (53).

【Chemical Formula 115】

(In the above general formula (53), R ₅₅₁ , R ₅₅₂ and R ₅₆₁ to R ₅₆₄ are each independently synonymous with R ₅₅₁ , R ₅₅₂ and R ₅₆₁ to R ₅₆₄ in the above general formula (52).)

In one embodiment, R ₅₆₁ to R ₅₆₄ in the general formula (52) and the general formula (53) are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms (preferably a phenyl group).

In one embodiment, R ₅₂₁ and R ₅₂₂ in the above general formula (5), and R ₅₅₁ and R ₅₅₂ in the above general formulas (52) and (53) are hydrogen atoms.

In one embodiment, the substituents in the above general formula (5), general formula (52) and general formula (53) when expressed as "substituted or unsubstituted" are

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

As specific examples of the compound represented by the general formula (5), for example, the following compounds can be mentioned.

【Chemical formula 116】

【Chemical formula 117】

【Chemical formula 118】

【Chemical formula 119】

【Chemical Formula 120】

【Chemical Formula 121】

【Chemical formula 122】

【Chemical Formula 123】

【Chemical formula 124】

【Chemical formula 125】

【Chemical formula 126】

【Chemical formula 127】

【Chemical formula 128】

【Chemical formula 129】

【Chemical Formula 130】

【Chemical Formula 131】

【Chemical formula 132】

(Compound represented by general formula (6))

The compound represented by the general formula (6) is described.

【Chemical formula 133】

(In the above general formula (6),

Ring a, ring b and ring c are each independently

A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms,

R ₆₀₁ and R ₆₀₂ each independently do not form a substituted or unsubstituted heterocyclic ring, or are bonded to the above-mentioned a ring, b ring or c ring to form a substituted or unsubstituted heterocyclic ring,

R ₆₀₁ and R ₆₀₂ which do not form the above substituted or unsubstituted heterocyclic ring are each independently

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

The rings a, b and c are rings fused to the fused bicyclic structure at the center of the general formula (6) consisting of a boron atom and two nitrogen atoms (a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms).

The "aromatic hydrocarbon ring" of the a ring, the b ring and the c ring has the same structure as the compound in which a hydrogen atom is introduced into the above-mentioned "aryl group".

The "aromatic hydrocarbon ring" of the a ring contains three carbon atoms in the condensed bicyclic structure at the center of the above general formula (6) as ring-constituting atoms.

The "aromatic hydrocarbon ring" of the b ring and the c ring contains two carbon atoms in the condensed bicyclic structure at the center of the above general formula (6) as ring-constituting atoms.

Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms" include compounds obtained by introducing a hydrogen atom into the "aryl group" described in Specific Example Group G1.

The "heterocycle" of the a ring, b ring and c ring has the same structure as a compound obtained by introducing a hydrogen atom into the above-mentioned "heterocyclic group".

The "heterocycle" of the a ring contains three carbon atoms in the fused bicyclic structure at the center of the general formula (6) as ring-forming atoms. The "heterocycle" of the b ring and the c ring contains two carbon atoms in the fused bicyclic structure at the center of the general formula (6) as ring-forming atoms. Specific examples of the "substituted or unsubstituted heterocycle having 5 to 50 ring atoms" include compounds obtained by introducing hydrogen atoms into the "heterocyclic group" described in the specific example group G2.

R ₆₀₁ and R ₆₀₂ may each independently bond to the a ring, b ring or c ring to form a substituted or unsubstituted heterocyclic ring. The heterocyclic ring in this case includes a nitrogen atom on the fused two-ring structure in the center of the general formula (6). The heterocyclic ring in this case may also include heteroatoms other than nitrogen atoms. Specifically, R ₆₀₁ and R ₆₀₂ bond to the a ring, b ring or c ring, and specifically, the atoms constituting the a ring, b ring or c ring bond to the atoms constituting R ₆₀₁ and R _602. For example, R ₆₀₁ may also bond to the a ring to form a nitrogen-containing heterocyclic ring fused with a ring containing R ₆₀₁ and a ring fused with two rings (or more than three rings). As specific examples of the nitrogen-containing heterocyclic ring, compounds corresponding to heterocyclic groups containing two or more nitrogen rings fused in the specific example group G2 may be cited.

The case where R ₆₀₁ is bonded to the b ring, the case where R ₆₀₂ is bonded to the a ring, and the case where R ₆₀₂ is bonded to the c ring are the same as above.

In one embodiment, the ring a, ring b and ring c in the general formula (6) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms.

In one embodiment, the ring a, ring b and ring c in the general formula (6) are each independently a substituted or unsubstituted benzene ring or a naphthalene ring.

In one embodiment, R ₆₀₁ and R ₆₀₂ in the above general formula (6) are each independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

It is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, the compound represented by the general formula (6) is a compound represented by the following general formula (62).

【Chemical formula 134】

(In the above general formula (62),

R _601A is bonded to one or more selected from R ₆₁₁ and R ₆₂₁ to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring,

R _602A is bonded to one or more selected from R ₆₁₃ and R ₆₁₄ to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring,

R _601A and R _602A which do not form the above substituted or unsubstituted heterocyclic ring are each independently

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

One or more of a group consisting of two or more adjacent ones of R ₆₁₁ to R ₆₂₁

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₆₁₁ to R ₆₂₁ which do not form the above substituted or unsubstituted heterocyclic ring, the above monocyclic ring, or the above condensed ring are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

R _601A and R _602A in the above general formula (62) are groups corresponding to R ₆₀₁ and R ₆₀₂ in the above general formula (6), respectively.

For example, R _601A and R ₆₁₁ may be bonded to form a nitrogen-containing heterocyclic ring containing a ring thereof and a benzene ring corresponding to the a ring, which is fused to two rings (or three or more rings). Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the heterocyclic group containing nitrogen and having two or more rings fused in the specific example group G2. The case where R _601A is bonded to R ₆₂₁ , the case where R _602A is bonded to R ₆₁₃ , and the case where R _602A is bonded to R ₆₁₄ are the same as above.

One or more of the groups consisting of two or more adjacent ones of R ₆₁₁ to R ₆₂₁ may be

bonded to each other to form a substituted or unsubstituted monocyclic ring, or

They are bonded to each other to form a substituted or unsubstituted condensed ring.

For example, R ₆₁₁ and R ₆₁₂ may bond to form a structure in which a benzene ring, indole ring, pyrrole ring, benzofuran ring or benzothiophene ring is condensed with the six-membered ring to which they are bonded, and the formed condensed ring becomes a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring or a dibenzothiophene ring.

In one embodiment, R ₆₁₁ to R ₆₂₁ not participating in the ring formation are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

In one embodiment, R ₆₁₁ to R ₆₂₁ not participating in the ring formation are each independently

Hydrogen atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

In one embodiment, R ₆₁₁ to R ₆₂₁ not participating in the ring formation are each independently

Hydrogen atoms, or

A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, R ₆₁₁ to R ₆₂₁ not participating in the ring formation are each independently

Hydrogen atoms, or

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

At least one of R ₆₁₁ to R ₆₂₁ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, the compound represented by the above general formula (62) is a compound represented by the following general formula (63).

【Chemical formula 135】

(In the above general formula (63),

R ₆₃₁ and R ₆₄₆ are bonded to form a substituted or unsubstituted heterocyclic ring, or do not form a substituted or unsubstituted heterocyclic ring,

R ₆₃₃ and R ₆₄₇ are bonded to form a substituted or unsubstituted heterocyclic ring, or do not form a substituted or unsubstituted heterocyclic ring,

R ₆₃₄ and R ₆₅₁ are bonded to form a substituted or unsubstituted heterocyclic ring, or do not form a substituted or unsubstituted heterocyclic ring,

R ₆₄₁ and R ₆₄₂ are bonded to form a substituted or unsubstituted heterocyclic ring, or do not form a substituted or unsubstituted heterocyclic ring,

One or more of a group consisting of two or more adjacent groups of R ₆₃₁ to R ₆₅₁

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₆₃₁ to R ₆₅₁ which do not form the above substituted or unsubstituted heterocyclic ring, the above monocyclic ring, or the above condensed ring are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

R ₆₃₁ may be bonded to R ₆₄₆ to form a substituted or unsubstituted heterocyclic ring. For example, R ₆₃₁ may be bonded to R ₆₄₆ to form a nitrogen-containing heterocyclic ring fused with a benzene ring to which R ₆₄₆ is bonded, a ring containing N, and three or more fused benzene rings corresponding to the a ring. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to the heterocyclic group containing nitrogen and three or more fused rings in Specific Example Group G2. The cases where R ₆₃₃ is bonded to R ₆₄₇ , the cases where R ₆₃₄ is bonded to R ₆₅₁ , and the cases where R ₆₄₁ is bonded to R ₆₄₂ are the same as above.

In one embodiment, R ₆₃₁ to R ₆₅₁ not involved in ring formation are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

In one embodiment, R ₆₃₁ to R ₆₅₁ not involved in ring formation are each independently

Hydrogen atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

In one embodiment, R ₆₃₁ to R ₆₅₁ not involved in ring formation are each independently

Hydrogen atoms, or

A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, R ₆₃₁ to R ₆₅₁ not involved in ring formation are each independently

Hydrogen atoms, or

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

At least one of R ₆₃₁ to R ₆₅₁ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, the compound represented by the above general formula (63) is a compound represented by the following general formula (63A).

【Chemical formula 136】

(In the above general formula (63A),

R ₆₆₁

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

R ₆₆₂ to R ₆₆₅ are each independently

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, R ₆₆₁ to R ₆₆₅ are each independently

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, R ₆₆₁ to R ₆₆₅ are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, the compound represented by the above general formula (63) is a compound represented by the following general formula (63B).

【Chemical formula 137】

(In the above general formula (63B),

R ₆₇₁ and R ₆₇₂ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-N(R ₉₀₆ )(R ₉₀₇ ), or

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

R ₆₇₃ to R ₆₇₅ are each independently

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-N(R ₉₀₆ )(R ₉₀₇ ), or

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, the compound represented by the above general formula (63) is a compound represented by the following general formula (63B').

【Chemical formula 138】

(In the above general formula (63B'), R ₆₇₂ to R ₆₇₅ are independently the same as R ₆₇₂ to R ₆₇₅ in the above general formula (63B).)

In one embodiment, at least one of R ₆₇₁ to R ₆₇₅ is

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-N(R ₉₀₆ )(R ₉₀₇ ), or

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment,

R ₆₇₂

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

-N(R ₉₀₆ )(R ₉₀₇ ), or

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

R ₆₇₁ and R ₆₇₃ to R ₆₇₅ are each independently

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

-N(R ₉₀₆ )(R ₉₀₇ ), or

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, the compound represented by the above general formula (63) is a compound represented by the following general formula (63C).

【Chemical formula 139】

(In the above general formula (63C),

R ₆₈₁ and R ₆₈₂ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

R ₆₈₃ to R ₆₈₆ are each independently

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, the compound represented by the above general formula (63) is a compound represented by the following general formula (63C').

【Chemical formula 140】

(In the above general formula (63C'), R ₆₈₃ to R ₆₈₆ each independently have the same meanings as R ₆₈₃ to R ₆₈₆ in the above general formula (63C).)

In one embodiment, R ₆₈₁ to R ₆₈₆ are each independently

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, R ₆₈₁ to R ₆₈₆ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

For the compound represented by the general formula (6), the a ring, the b ring and the c ring can be first bonded by a connecting group (a group containing NR ₆₀₁ and a group containing NR ₆₀₂ ) to produce an intermediate (first reaction), and then the a ring, the b ring and the c ring can be bonded by a connecting group (a group containing a boron atom) to produce a final product (second reaction). In the first reaction, an amination reaction such as the Buchwald-Hartwig reaction can be applied. In the second reaction, a tandem hetero Friedel-Crafts reaction can be applied.

Specific examples of the compound represented by the general formula (6) are described below. These are merely illustrative and the compound represented by the general formula (6) is not limited to the following specific examples.

【Chemical formula 141】

【Chemical formula 142】

【Chemical formula 143】

【Chemical formula 144】

【Chemical formula 145】

【Chemical formula 146】

【Chemical formula 147】

【Chemical formula 148】

【Chemical formula 149】

【Chemical formula 150】

【Chemical formula 151】

【Chemical formula 152】

【Chemical formula 153】

【Chemical formula 154】

【Chemical formula 155】

【Chemical formula 156】

【Chemical formula 157】

【Chemical formula 158】

(Compound represented by general formula (7))

The compound represented by the general formula (7) is described.

【Chemical formula 159】

【Chemical formula 160】

(In the above general formula (7),

The r ring is a ring represented by the above general formula (72) or (73) fused at any position of the adjacent ring,

The q ring and the s ring are each independently a ring represented by the above general formula (74) fused at any position of the adjacent rings,

The p ring and the t ring are each independently a structure represented by the above general formula (75) or general formula (76) fused at any position of the adjacent rings,

X ₇ is an oxygen atom, a sulfur atom or NR ₇₀₂ .

When there are multiple R ₇₀₁ , the adjacent multiple R ₇₀₁

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₇₀₁ and R ₇₀₂ which do not form the above monocyclic ring and do not form the above condensed ring are each independently

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

Ar ₇₀₁ and Ar ₇₀₂ are each independently

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

L ₇₀₁

a substituted or unsubstituted alkylene group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenylene group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynylene group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkylene group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

ml is 0, 1 or 2,

m2 is 0, 1, 2, 3 or 4,

m3 is each independently 0, 1, 2 or 3,

m4 are each independently 0, 1, 2, 3, 4 or 5,

When there are plural R ₇₀₁ , the plural R ₇₀₁ are the same as or different from each other.

When there are multiple _X7 , the multiple _X7 are the same or different from each other.

When there are plural R ₇₀₂ , the plural R ₇₀₂ are the same as or different from each other.

When there are a plurality of Ar ₇₀₁ , the plurality of Ar ₇₀₁ may be identical to or different from each other.

When there are a plurality of Ar ₇₀₂ , the plurality of Ar ₇₀₂ may be identical to or different from each other.

When there are multiple _L701 , the multiple _L701 are the same as or different from each other.)

In the general formula (7), each of the p ring, q ring, r ring, s ring and t ring is fused to the adjacent ring so as to share two carbon atoms. The position and direction of fusion are not limited, and fusion can be performed at any position and direction.

In one embodiment, in the above general formula (72) or general formula (73) as the r ring, m1=0 or m2=0.

In one embodiment, the compound represented by the general formula (7) is represented by any one of the following general formulas (71-1) to (71-6).

【Chemical formula 161】

【Chemical formula 162】

【Chemical formula 163】

【Chemical formula 164】

【Chemical formula 165】

【Chemical formula 166】

(In the above general formulae (71-1) to (71-6), R ₇₀₁ , X ₇ , Ar ₇₀₁ , Ar ₇₀₂ , L ₇₀₁ , m1 and m3 have the same meanings as R ₇₀₁ , X ₇ , Ar ₇₀₁ , Ar ₇₀₂ , L ₇₀₁ , m1 and m3 in the above general formula (7), respectively.)

In one embodiment, the compound represented by the general formula (7) is represented by any one of the following general formulas (71-11) to (71-13).

【Chemical formula 167】

【Chemical formula 168】

【Chemical formula 169】

(In the above general formulae (71-11) to (71-13), R ₇₀₁ , X ₇ , Ar ₇₀₁ , Ar ₇₀₂ , L ₇₀₁ , m1, m3 and m4 have the same meanings as R ₇₀₁ , X ₇ , Ar ₇₀₁ , Ar ₇₀₂ , L ₇₀₁ , m1, m3 and m4 in the above general formula (7), respectively.

In one embodiment, the compound represented by the general formula (7) is represented by any one of the following general formulae (71-21) to (71-25).

【Chemical formula 170】

【Chemical formula 171】

【Chemical formula 172】

【Chemical formula 173】

【Chemical formula 174】

(In the above general formulae (71-21) to (71-25), R ₇₀₁ , X ₇ , Ar ₇₀₁ , Ar ₇₀₂ , L ₇₀₁ , m1 and m4 have the same meanings as R ₇₀₁ , X ₇ , Ar ₇₀₁ , Ar ₇₀₂ , L ₇₀₁ , m1 and m4 in the above general formula (7), respectively.)

In one embodiment, the compound represented by the general formula (7) is represented by any one of the following general formulas (71-31) to (71-33).

【Chemical formula 175】

【Chemical formula 176】

【Chemical formula 177】

(In the above general formulae (71-31) to (71-33), R ₇₀₁ , X ₇ , Ar ₇₀₁ , Ar ₇₀₂ , L ₇₀₁ , and m2 to m4 have the same meanings as R ₇₀₁ , X ₇ , Ar ₇₀₁ , Ar ₇₀₂ , L ₇₀₁ , and m2 to m4 in the above general formula (7), respectively.)

In one embodiment, Ar ₇₀₁ and Ar ₇₀₂ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, one of Ar ₇₀₁ and Ar ₇₀₂ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the other of Ar ₇₀₁ and Ar ₇₀₂ is a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

Specific examples of the compound represented by the general formula (7) include the following compounds.

【Chemical formula 178】

【Chemical formula 179】

【Chemical formula 180】

【Chemical formula 181】

【Chemical formula 182】

【Chemical formula 183】

(Compound represented by general formula (8))

The compound represented by the general formula (8) is described.

【Chemical formula 184】

(In the above general formula (8),

At least one of _R801 and _R802 , _R802 and _R803 , and _R803 and _R804 is bonded to each other to form a divalent group represented by the following general formula (82):

At least one of _R805 and _R806 , _R806 and _R807 , and _R807 and _R808 is bonded to each other to form a divalent group represented by the following general formula (83).

【Chemical formula 185】

(At least one of R ₈₀₁ to R ₈₀₄ and R ₈₁₁ to R ₈₁₄ which do not form a divalent group represented by the above general formula (82) is a monovalent group represented by the following general formula (84),

At least one of R ₈₀₅ to R ₈₀₈ and R ₈₂₁ to R ₈₂₄ which do not form a divalent group represented by the above general formula (83) is a monovalent group represented by the following general formula (84),

X ₈ is an oxygen atom, a sulfur atom, or NR ₈₀₉ ,

R ₈₀₁ to R ₈₀₈ which do not form a divalent group represented by the general formula (82) and the general formula (83) and are not a monovalent group represented by the general formula (84), R ₈₁₁ to R ₈₁₄ and R ₈₂₁ to R ₈₂₄ which are not a monovalent group represented by the general formula (84), and R ₈₀₉ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

【Chemical formula 186】

(In the above general formula (84),

Ar ₈₀₁ and Ar ₈₀₂ are each independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

L ₈₀₁ ～L ₈₀₃ are each independently

single bond,

a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,

a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or

a divalent linking group formed by bonding 2 to 4 groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms,

The * in the above general formula (84) represents the bonding position to the ring structure represented by the above general formula (8), the group represented by the general formula (82) or the general formula (83).

In the general formula (8), the positions at which the divalent group represented by the general formula (82) and the divalent group represented by the general formula (83) are formed are not particularly limited, and the groups can be formed at possible positions of R ₈₀₁ to R ₈₀₈ .

In one embodiment, the compound represented by the general formula (8) is represented by any one of the following general formulas (81-1) to (81-6).

【Chemical formula 187】

【Chemical formula 188】

【Chemical formula 189】

(In the above general formulas (81-1) to (81-6),

_X8 has the same meaning as _X8 in the above general formula (8),

At least two of R ₈₀₁ to R ₈₂₄ are monovalent groups represented by the above general formula (84),

R ₈₀₁ to R ₈₂₄ which are not monovalent groups represented by the general formula (84) above are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

In one embodiment, the compound represented by the general formula (8) is represented by any one of the following general formulas (81-7) to (81-18).

【Chemical formula 190】

【Chemical formula 191】

【Chemical formula 192】

【Chemical formula 193】

【Chemical formula 194】

【Chemical formula 195】

(In the above general formulas (81-7) to (81-18),

_X8 has the same meaning as _X8 in the above general formula (8),

* is a single bond bonded to the monovalent group represented by the above general formula (84),

R ₈₀₁ to R ₈₂₄ are each independently the same as R ₈₀₁ to R ₈₂₄ in the above-mentioned general formulae (81-1) to (81-6) which are monovalent groups other than those represented by the above-mentioned general formula (84).

R ₈₀₁ to R ₈₀₈ which do not form a divalent group represented by the general formula (82) and the general formula (83) and are not a monovalent group represented by the general formula (84), and R ₈₁₁ to R ₈₁₄ and R ₈₂₁ to R ₈₂₄ which are not a monovalent group represented by the general formula (84) are preferably each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

The monovalent group represented by the general formula (84) is preferably represented by the following general formula (85) or (86).

【Chemical formula 196】

(In the above general formula (85),

R ₈₃₁ to R ₈₄₀ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

The * in the above general formula (85) has the same meaning as the * in the above general formula (84).

【Chemical formula 197】

(In the above general formula (86),

Ar ₈₀₁ , L ₈₀₁ and L ₈₀₃ have the same meanings as Ar ₈₀₁ , L ₈₀₁ and L ₈₀₃ in the above general formula (84).

HAr ₈₀₁ has a structure represented by the following general formula (87).

【Chemical formula 198】

(In the above general formula (87),

X ₈₁ is an oxygen atom or a sulfur atom,

Any one of R ₈₄₁ to R ₈₄₈ is a single bond bonded to L ₈₀₃ ,

R ₈₄₁ to R ₈₄₈ which are not single bonds are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

Specific examples of the compound represented by the general formula (8) include the compounds described in International Publication No. 2014/104144 and the compounds shown below.

【Chemical formula 199】

【Chemical Formula 200】

【Chemical Formula 201】

【Chemical Formula 202】

【Chemical Formula 203】

【Chemical formula 204】

(Compound represented by general formula (9))

The compound represented by the general formula (9) is described.

【Chemical Formula 205】

(In the above general formula (9),

Ring _A91 and Ring _A92 are each independently

a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms,

One or more rings selected from the group consisting of ring _A91 and ring _A92

Bonded to * of the structure represented by the following general formula (92).

【Chemical formula 206】

(In the above general formula (92),

A ₉₃ ring is

a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms,

_X9 is _NR93 , C( _R94 )( _R95 ), Si( _R96 )( _R97 ), Ge( _R98 )( _R99 ), an oxygen atom, a sulfur atom or a selenium atom,

R ₉₁ and R ₉₂

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₉₁ and R ₉₂ , and R ₉₃ to R ₉₉ which do not form the above-mentioned monocyclic ring and the above-mentioned condensed ring, are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

One or more rings selected from the _A91 ring and the _A92 ring are bonded to the * of the structure represented by the general formula (92). That is, in one embodiment, the ring-forming carbon atom of the above aromatic hydrocarbon ring of the _A91 ring or the ring-forming atom of the above heterocyclic ring is bonded to the * of the structure represented by the general formula (92). In addition, in one embodiment, the ring-forming carbon atom of the above aromatic hydrocarbon ring of the _A92 ring or the ring-forming atom of the above heterocyclic ring is bonded to the * of the structure represented by the general formula (92).

In one embodiment, the group represented by the following general formula (93) is bonded to one or both of the _A91 ring and the _A92 ring.

【Chemical formula 207】

(In the above general formula (93),

Ar ₉₁ and Ar ₉₂ are each independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

L ₉₁ to L ₉₃ are each independently

single bond,

a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,

a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms, or

a divalent linking group formed by bonding 2 to 4 groups selected from the group consisting of a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms and a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atoms,

In the above general formula (93), * represents the bonding position to either the _A91 ring or the _A92 ring.

In one embodiment, in addition to the _A91 ring, the above-mentioned aromatic hydrocarbon ring ring carbon atom or the above-mentioned heterocyclic ring ring atom of the _A92 ring is bonded to the * of the structure represented by the above-mentioned general formula (92). In this case, the structures represented by the above-mentioned general formula (92) may be the same or different from each other.

In one embodiment, R ₉₁ and R ₉₂ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, R ₉₁ and R ₉₂ are bonded to each other to form a fluorene structure.

In one embodiment, Ring A ₉₁ and Ring A ₉₂ are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring.

In one embodiment, Ring A ₉₃ is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring.

In one embodiment, X ₉ is an oxygen atom or a sulfur atom.

As specific examples of the compound represented by the general formula (9), for example, the following compounds can be mentioned.

【Chemical formula 208】

【Chemical formula 209】

【Chemical Formula 210】

【Chemical Formula 211】

(Compound represented by general formula (10))

The compound represented by the general formula (10) is described.

【Chemical Formula 212】

【Chemical Formula 213】

(In the above general formula (10),

_Ax1 ring is a ring represented by the above general formula (10a) fused at any position of the adjacent ring,

The _Ax2 ring is a ring represented by the above general formula (10b) fused at any position of the adjacent ring,

In the above general formula (10b), the two * are bonded to any position of the Ax ₃ ring.

_XA and _XB are each independently C(R ₁₀₀₃ )(R ₁₀₀₄ ), Si(R ₁₀₀₅ )(R ₁₀₀₆ ), an oxygen atom or a sulfur atom,

Ax ₃ ring is

A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms,

Ar ₁₀₀₁

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

R ₁₀₀₁ to R ₁₀₀₆ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

mx1 is 3, mx2 is 2,

A plurality of R ₁₀₀₁ are the same as or different from each other,

A plurality of R ₁₀₀₂ are the same as or different from each other,

ax is 0, 1, or 2,

When ax is 0 or 1, the structures in the brackets shown by "3-ax" are the same or different from each other.

When ax is 2, a plurality of Ar ₁₀₀₁ are identical to or different from each other.)

In one embodiment, Ar ₁₀₀₁ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. In one embodiment, Ax ₃ is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, such as a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or a substituted or unsubstituted anthracene ring.

In one embodiment, R ₁₀₀₃ and R ₁₀₀₄ are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, ax is 1.

As specific examples of the compound represented by the general formula (10), the following compounds can be mentioned.

【Chemical formula 214】

In one embodiment, the light-emitting layer 5 contains as a light-emitting compound a

The compound represented by the above general formula (4),

The compound represented by the above general formula (5),

The compound represented by the above general formula (6), and

One or more compounds represented by the following general formula (63a).

【Chemical Formula 215】

(In the above general formula (63a),

R ₆₃₁ and R ₆₄₆ bond to form a substituted or unsubstituted heterocyclic ring, or do not form a substituted or unsubstituted heterocyclic ring.

R ₆₃₃ and R ₆₄₇ bond to form a substituted or unsubstituted heterocyclic ring, or do not form a substituted or unsubstituted heterocyclic ring.

R ₆₃₄ and R ₆₅₁ bond to form a substituted or unsubstituted heterocyclic ring, or do not form a substituted or unsubstituted heterocyclic ring.

R ₆₄₁ and R ₆₄₂ bond to form a substituted or unsubstituted heterocyclic ring, or do not form a substituted or unsubstituted heterocyclic ring.

One or more sets of two or more adjacent ones from R ₆₃₁ to R ₆₅₁

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₆₃₁ to R ₆₅₁ which do not form the above substituted or unsubstituted heterocyclic ring, the above monocyclic ring, or the above condensed ring are each independently

Hydrogen atoms,

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

Among them, at least one of R ₆₃₁ to R ₆₅₁ that does not form the above-mentioned substituted or unsubstituted heterocyclic ring, does not form the above-mentioned monocyclic ring, and does not form the above-mentioned condensed ring is

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

In one embodiment, the compound represented by the general formula (4) is a compound represented by the general formula (41-3), the general formula (41-4) or the general formula (41-5), wherein the A1 ring in the general formula (41-5) is a substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms or a substituted or unsubstituted fused heterocycle having 8 to 50 ring atoms.

In one embodiment, the substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms in the general formula (41-3), the general formula (41-4), and the general formula (41-5) is

a substituted or unsubstituted naphthalene ring,

A substituted or unsubstituted anthracene ring, or

a substituted or unsubstituted fluorene ring,

The substituted or unsubstituted fused heterocyclic ring having 8 to 50 ring atoms is

a substituted or unsubstituted dibenzofuran ring,

A substituted or unsubstituted carbazole ring, or

A substituted or unsubstituted dibenzothiophene ring.

In one embodiment, the substituted or unsubstituted fused aromatic hydrocarbon ring having 10 to 50 ring carbon atoms in the general formula (41-3), the general formula (41-4) or the general formula (41-5) is

A substituted or unsubstituted naphthalene ring, or

a substituted or unsubstituted fluorene ring,

The substituted or unsubstituted fused heterocyclic ring having 8 to 50 ring atoms is

a substituted or unsubstituted dibenzofuran ring,

A substituted or unsubstituted carbazole ring, or

A substituted or unsubstituted dibenzothiophene ring.

In one embodiment, the compound represented by the general formula (4) is selected from

The compound represented by the following general formula (461),

The compound represented by the following general formula (462),

The compound represented by the following general formula (463),

The compound represented by the following general formula (464),

The compound represented by the following general formula (465),

The compound represented by the following general formula (466), and

The group consisting of compounds represented by the following general formula (467).

【Chemical Formula 216】

【Chemical Formula 217】

【Chemical formula 218】

【Chemical formula 219】

【Chemical Formula 220】

(In the above general formulas (461) to (467),

One or more of the group consisting of two or more adjacent ones of R ₄₂₁ to R ₄₂₇ , R ₄₃₁ to R ₄₃₆ , R ₄₄₀ to R ₄₄₈ and R ₄₅₁ to R ₄₅₄

bonded to each other to form a substituted or unsubstituted monocyclic ring,

bonded to each other to form a substituted or unsubstituted condensed ring, or

Not bonded to each other,

R ₄₃₇ , R ₄₃₈ , and R ₄₂₁ to R ₄₂₇ , R ₄₃₁ to R ₄₃₆ , R ₄₄₀ to R ₄₄₈ and R ₄₅₁ to R ₄₅₄ which do not form the above-mentioned monocyclic ring and do not form the above-mentioned condensed ring are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

_X4 is an oxygen atom, _NR801 , or C( _R802 )( _R803 ),

R ₈₀₁ , R ₈₀₂ and R ₈₀₃ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

Preferably, it is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,

When there are multiple _R801 , the multiple _R801 are the same as or different from each other.

When there are multiple R ₈₀₂ , the multiple R ₈₀₂ are the same as or different from each other.

When there are multiple _R803 , the multiple _R803 are the same as or different from each other.)

In one embodiment, R ₄₂₁ to R ₄₂₇ and R ₄₄₀ to R ₄₄₈ are each independently

Hydrogen atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

In one embodiment, R ₄₂₁ -R ₄₂₇ and R ₄₄₀ -R ₄₄₇ are each independently selected from

Hydrogen atoms,

a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, and

A group consisting of a substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

In one embodiment, the compound represented by the general formula (41-3) is a compound represented by the following general formula (41-3-1).

【Chemical Formula 221】

(In the above general formula (41-3-1), R ₄₂₃ , R ₄₂₅ , R ₄₂₆ , R _{442 , R 444} and R ₄₄₅ are independently the same as R ₄₂₃ , R ₄₂₅ , R ₄₂₆ , R ₄₄₂ , R ₄₄₄ and R ₄₄₅ in the above general formula ( _41-3 ).)

In one embodiment, the compound represented by the general formula (41-3) is a compound represented by the following general formula (41-3-2).

【Chemical Formula 222】

(In the above general formula (41-3-2), R ₄₂₁ to R ₄₂₇ and R ₄₄₀ to R ₄₄₈ are independently the same as R ₄₂₁ to R ₄₂₇ and R ₄₄₀ to R ₄₄₈ in the above general formula (41-3),

In this case, at least one of R ₄₂₁ to R ₄₂₇ and R ₄₄₀ to R ₄₄₆ is a group represented by -N(R ₉₀₆ )(R ₉₀₇ ).

In one embodiment, any two of R ₄₂₁ to R ₄₂₇ and R ₄₄₀ to R ₄₄₆ in the general formula (41-3-2) are groups represented by -N(R ₉₀₆ )(R ₉₀₇ ).

In one embodiment, the compound represented by the general formula (41-3-2) is a compound represented by the following formula (41-3-3).

【Chemical Formula 223】

(In the above general formula (41-3-3), R ₄₂₁ to R ₄₂₄ , R ₄₄₀ to R ₄₄₃ , R ₄₄₇ and R ₄₄₈ are each independently synonymous with R ₄₂₁ to R ₄₂₄ , R ₄₄₀ to R ₄₄₃ , R ₄₄₇ and R ₄₄₈ in the above general formula (41-3),

_RA , _RB , _RC and _RD are each independently

a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 18 ring atoms.

In one embodiment, the compound represented by the general formula (41-3-3) is a compound represented by the following formula (41-3-4).

【Chemical formula 224】

(In the above general formula (41-3-4), R ₄₄₇ , R ₄₄₈ , _RA , RB , _RC and _RD are independently the same as R ₄₄₇ , R ₄₄₈ , _RA , _RB , _RC and _RD in the above general formula ( _41-3-3 ).)

In one embodiment, _RA , _RB , _RC and _RD are each independently a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.

In one embodiment, _RA , _RB , _RC and _RD are each independently substituted or unsubstituted phenyl.

In one embodiment, R ₄₄₇ and R ₄₄₈ are hydrogen atoms.

In the organic EL element 1A, the light-emitting compound contained in the light-emitting layer 5 is preferably a compound that emits light with a maximum peak wavelength of 500 nm or less, and more preferably a compound that emits light at 430 nm to 480 nm.

In the organic EL element 1A, the light-emitting compound contained in the light-emitting layer 5 is preferably a compound that emits fluorescence with a maximum peak wavelength of 500 nm or less, and more preferably a compound that emits fluorescence at 430 nm to 480 nm.

In the organic EL element 1A, when the light-emitting layer 5 includes the compound involved in the first embodiment and the light-emitting compound, the compound involved in the first embodiment is preferably a main material (sometimes also called a matrix material), and the light-emitting compound is preferably a dopant material (sometimes also called a guest material, an emitter or a light-emitting material).

In the organic EL element 1A, when the light-emitting layer 5 contains the compound involved in the second embodiment and the light-emitting compound, the compound involved in the second embodiment is preferably a main material (sometimes also called a matrix material), and the light-emitting compound is preferably a dopant material (sometimes also called a guest material, an emitter or a light-emitting material).

In the organic EL element 1A, when the light-emitting layer 5 contains the compound involved in the third embodiment and a light-emitting compound, the compound involved in the third embodiment is preferably a main material (sometimes also called a matrix material), and the light-emitting compound is preferably a dopant material (sometimes also called a guest material, an emitter or a light-emitting material).

In this specification, the term "host material" refers to, for example, a material whose content is "50% by mass or more of a layer".

Therefore, for example, in the case of the organic EL element 1A, the content of the compound represented by the general formula (1A) in the light-emitting layer 5 is 50% by mass or more of the total mass of the light-emitting layer.

Therefore, for example, in the case of the organic EL element 1A, the content of the compound represented by the general formula (1C) in the light-emitting layer 5 is 50% by mass or more of the total mass of the light-emitting layer.

(Thickness of the light-emitting layer)

The film thickness of the luminescent layer 5 is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and further preferably 10 nm or more and 50 nm or less. If the film thickness of the luminescent layer is 5 nm or more, it is easy to form the luminescent layer and easy to adjust the chromaticity. If the film thickness of the luminescent layer is 50 nm or less, it is easy to suppress the rise of the driving voltage.

(Content ratio of compound in light-emitting layer)

When the light-emitting layer 5 contains the compound according to the first embodiment and a light-emitting compound, the contents of the compound according to the first embodiment and the light-emitting compound in the light-emitting layer 5 are preferably in the following ranges, for example.

The content of the compound according to the first embodiment is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less.

The content of the light-emitting compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and even more preferably 1% by mass or more and 5% by mass or less.

However, the upper limit of the total content of the compound according to the first embodiment and the light-emitting compound in the light-emitting layer 5 is 100 mass %.

When the light-emitting layer 5 contains the compound according to the second embodiment and a light-emitting compound, the contents of the compound according to the second embodiment and the light-emitting compound in the light-emitting layer 5 are preferably in the following ranges, for example.

The content of the compound according to the second embodiment is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less.

The content of the light-emitting compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and even more preferably 1% by mass or more and 5% by mass or less.

However, the upper limit of the total content of the compound according to the second embodiment and the light-emitting compound in the light-emitting layer 5 is 100 mass %.

When the light-emitting layer 5 contains the compound according to the third embodiment and a light-emitting compound, the contents of the compound according to the third embodiment and the light-emitting compound in the light-emitting layer 5 are preferably in the following ranges, for example.

The content of the compound according to the third embodiment is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less.

The content of the light-emitting compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and even more preferably 1% by mass or more and 5% by mass or less.

However, the upper limit of the total content of the compound according to the third embodiment and the light-emitting compound in the light-emitting layer 5 is 100 mass %.

It should be noted that this embodiment does not exclude the inclusion of materials other than the compound and the light-emitting compound according to the first embodiment in the light-emitting layer 5 .

The light-emitting layer 5 may contain only one kind of the compound according to the first embodiment, or may contain two or more kinds thereof. The light-emitting layer 5 may contain only one kind of the light-emitting compound, or may contain two or more kinds thereof.

In addition, this embodiment does not exclude the inclusion of materials other than the compound according to the second embodiment and the light-emitting compound in the light-emitting layer 5 .

The compound according to the second embodiment may be contained in the light-emitting layer 5 in the form of one or more. The light-emitting layer 5 may be contained in the form of one or more.

In addition, this embodiment does not exclude the inclusion of materials other than the compound and the light-emitting compound according to the third embodiment in the light-emitting layer 5 .

The light-emitting layer 5 may contain only one kind of the compound according to the third embodiment, or may contain two or more kinds thereof. The light-emitting layer 5 may contain only one kind of the light-emitting compound, or may contain two or more kinds thereof.

FIG. 2 schematically shows the structure of another example of the organic EL element according to the present embodiment.

2 is different from the organic EL element 1A in that the organic layer 10B includes the first light-emitting region 5B, and is the same as the organic EL element 1A in other respects. The first light-emitting region 5B includes a first light-emitting layer 51 and a second light-emitting layer 52 in this order from the anode 3 side.

The first light-emitting layer 51 contains a first compound, and the second light-emitting layer 52 contains a second compound. The first compound and the second compound are different compounds from each other.

(First Compound)

In one embodiment of the organic EL device 1B, the first compound is the compound according to the first embodiment.

In one aspect of the organic EL device according to the present embodiment, the first compound may be a compound represented by the above-mentioned general formula (1C-A).

In one embodiment of the organic EL device 1B, the first compound is the compound according to the second embodiment.

In one aspect of the organic EL device according to the present embodiment, the first compound may be a compound represented by the above-mentioned general formula (1C-B).

In one embodiment of the organic EL device 1B, the first compound is the compound according to the third embodiment.

In one aspect of the organic EL device according to the present embodiment, the first compound may be a compound represented by the above-mentioned general formula (1C-C).

In one embodiment of the organic EL device 1B, the first compound is a compound represented by the above-mentioned general formula (1C).

(Second Compound)

In the organic EL device 1B, the second compound is preferably a compound represented by the following general formula (2).

【Chemical Formula 225】

(In the above general formula (2),

R ₂₀₁ to R ₂₀₈ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C(=O)R ₈₀₁ ,

-COOR ₈₀₂ ,

Halogen atoms,

Cyano,

Nitro,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms,

_L201 and _L202 are each independently

single bond,

a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

Ar ₂₀₁ and Ar ₂₀₂ are each independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

(In the second compound according to this embodiment, R ₉₀₁ , R ₉₀₂ , R ₉₀₃ , R ₉₀₄ , R ₉₀₅ , R ₉₀₆ , R ₉₀₇ , R ₈₀₁ and R ₈₀₂ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms; when there are multiple _R901s , the multiple _R901s are the same or different from each other; when there are multiple _R902s , the multiple _R902s are the same or different from each other; when there are multiple _R903s , the multiple _R903s are the same or different from each other; when there are multiple _R904s , the multiple _R904s are the same or different from each other; when there are multiple _R905s , the multiple _R905s are the same or different from each other; when there are multiple _R906s , the multiple _R906s are the same or different from each other; when there are multiple _R907s , the multiple _R907s are the same or different from each other; when there are multiple _R801s , the multiple _R801s are the same or different from each other; when there are multiple _R802s , the multiple _R802s are the same or different from each other.) In the organic EL element according to this embodiment, it is preferred that

R ₂₀₁ to R ₂₀₈ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),

-O-(R ₉₀₄ ),

-S-(R ₉₀₅ ),

-N(R ₉₀₆ )(R ₉₀₇ ),

a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C(=O)R ₈₀₁ ,

-COOR ₈₀₂ ,

Halogen atoms,

Cyano or

Nitro,

_L201 and _L202 are each independently

single bond,

a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or

a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,

Ar ₂₀₁ and Ar ₂₀₂ are each independently

a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

In the organic EL element according to this embodiment, it is preferred that:

_L201 and _L202 are each independently

Single key, or

a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms,

Ar ₂₀₁ and Ar ₂₀₂ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In the organic EL element according to this embodiment, it is preferred that:

Ar ₂₀₁ and Ar ₂₀₂ are each independently

Phenyl,

Naphthyl,

Fiki,

Biphenyl,

Terphenyl,

Diphenylfluorenyl,

Dimethylfluorenyl,

Benzodiphenylfluorenyl,

Benzodimethylfluorenyl,

Dibenzofuranyl,

Dibenzothiophene,

naphthobenzofuranyl, or

Naphthobenzothienyl.

In the organic EL element involved in this embodiment, the second compound represented by the general formula (2) is preferably a compound represented by the following general formula (201), general formula (202), general formula (203), general formula (204), general formula (205), general formula (206), general formula (207), general formula (208) or general formula (209).

【Chemical formula 226】

【Chemical formula 227】

【Chemical formula 228】

【Chemical formula 229】

【Chemical Formula 230】

【Chemical Formula 231】

【Chemical formula 232】

【Chemical Formula 233】

【Chemical formula 234】

(In the above general formulas (201) to (209),

L ₂₀₁ and Ar ₂₀₁ have the same meanings as L ₂₀₁ and Ar ₂₀₁ in the above general formula (2),

R ₂₀₁ to R ₂₀₈ are each independently the same as R ₂₀₁ to R ₂₀₈ in the above general formula (2).

The second compound represented by the above general formula (2) is also preferably a compound represented by the following general formula (221), general formula (222), general formula (223), general formula (224), general formula (225), general formula (226), general formula (227), general formula (228) or general formula (229).

【Chemical Formula 235】

【Chemical formula 236】

【Chemical formula 237】

【Chemical formula 238】

【Chemical formula 239】

【Chemical Formula 240】

【Chemical Formula 241】

【Chemical formula 242】

【Chemical formula 243】

(In the above general formula (221), general formula (222), general formula (223), general formula (224), general formula (225), general formula (226), general formula (227), general formula (228) and general formula (229),

R ₂₀₁ and R ₂₀₃ to R ₂₀₈ are each independently the same as R ₂₀₁ and R ₂₀₃ to R ₂₀₈ in the above general formula (2),

L ₂₀₁ and Ar ₂₀₁ have the same meanings as L ₂₀₁ and Ar ₂₀₁ in the above general formula (2),

_L203 has the same meaning as _L201 in the above general formula (2),

_L203 and _L201 are the same as or different from each other,

Ar ₂₀₃ has the same meaning as Ar ₂₀₁ in the above general formula (2),

Ar ₂₀₃ and Ar ₂₀₁ are the same as or different from each other.)

The second compound represented by the above general formula (2) is also preferably a compound represented by the following general formula (241), general formula (242), general formula (243), general formula (244), general formula (245), general formula (246), general formula (247), general formula (248) or general formula (249).

【Chemical formula 244】

【Chemical Formula 245】

【Chemical formula 246】

【Chemical formula 247】

【Chemical formula 248】

【Chemical formula 249】

【Chemical Formula 250】

【Chemical Formula 251】

【Chemical formula 252】

(In the above general formula (241), general formula (242), general formula (243), general formula (244), general formula (245), general formula (246), general formula (247), general formula (248) and general formula (249),

R ₂₀₁ , R ₂₀₂ and R ₂₀₄ to R ₂₀₈ are each independently the same as R ₂₀₁ , R ₂₀₂ and R ₂₀₄ to R ₂₀₈ in the above general formula (2),

L ₂₀₁ and Ar ₂₀₁ have the same meanings as L ₂₀₁ and Ar ₂₀₁ in the above general formula (2),

_L203 has the same meaning as _L201 in the above general formula (2),

_L203 and _L201 are the same as or different from each other,

Ar ₂₀₃ has the same meaning as Ar ₂₀₁ in the above general formula (2),

Ar ₂₀₃ and Ar ₂₀₁ are the same as or different from each other.)

In the second compound represented by the general formula (2), preferably, R ₂₀₁ to R ₂₀₈ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

A group represented by -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ).

Preferably, L ₂₀₁ is

Single key, or

an unsubstituted arylene group having 6 to 22 ring carbon atoms,

Ar ₂₀₁ is a substituted or unsubstituted aryl group having 6 to 22 ring carbon atoms.

In the organic EL element according to this embodiment,

In the second compound represented by the general formula (2), preferably, R ₂₀₁ to R ₂₀₈ are each independently

Hydrogen atoms,

a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or

A group represented by -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ).

In the organic EL element according to this embodiment,

In the second compound represented by the above general formula (2), R ₂₀₁ to R ₂₀₈ are preferably hydrogen atoms.

In the above-mentioned second compound, the groups described as "substituted or unsubstituted" are all preferably "unsubstituted" groups.

In the organic EL device according to the present embodiment, for example, Ar ₂₀₁ in the second compound represented by the general formula (2) is a substituted or unsubstituted dibenzofuranyl group.

In the organic EL device according to the present embodiment, for example, Ar ₂₀₁ in the second compound represented by the general formula (2) is an unsubstituted dibenzofuranyl group.

In the organic EL device according to this embodiment, for example, the second compound represented by the general formula (2) contains at least one hydrogen atom, and at least one of the hydrogen atom is deuterium.

In the organic EL device according to this embodiment, for example, _L201 in the second compound represented by the general formula (2) is TEMP-63 to TEMP-68.

【Chemical formula 253】

In the organic EL device according to this embodiment, for example, Ar ₂₀₁ in the second compound represented by the general formula (2) is selected from substituted or unsubstituted anthracene,

Benzanthryl,

Fiki,

Triphenylene,

Phenyl,

Pyrene

base,

Benzo base,

Triphenylene,

Benzotriphenylene,

Tetraphenylene,

Pentaphenyl,

Fluoranthene,

Benzofluoranthene, and

At least one group selected from the group consisting of perylenyl.

In the organic EL device according to this embodiment, for example, Ar ₂₀₁ in the second compound represented by the general formula (2) is a substituted or unsubstituted fluorenyl group.

In the organic EL device according to this embodiment, for example, Ar ₂₀₁ in the second compound represented by the general formula (2) is a substituted or unsubstituted xanthene group.

In the organic EL device according to this embodiment, for example, _Ar2O1 in the second compound represented by the general formula (2) is a benzoxanthenyl group.

(Method for producing the second compound)

The second compound can be produced by a known method. Alternatively, the second compound can be produced by following a known method by using a known substitution reaction and raw materials corresponding to the target substance.

(Specific example of the second compound)

Specific examples of the second compound include the following compounds. However, the present invention is not limited to these specific examples of the second compound.

【Chemical formula 254】

【Chemical formula 255】

【Chemical formula 256】

【Chemical formula 257】

【Chemical formula 258】

【Chemical formula 259】

【Chemical Formula 260】

【Chemical Formula 261】

【Chemical formula 262】

【Chemical formula 263】

【Chemical formula 264】

【Chemical formula 265】

【Chemical formula 266】

【Chemical formula 267】

【Chemical formula 268】

【Chemical formula 269】

【Chemical Formula 270】

【Chemical Formula 271】

【Chemical formula 272】

【Chemical formula 273】

【Chemical formula 274】

【Chemical Formula 275】

【Chemical formula 276】

【Chemical formula 277】

【Chemical formula 278】

【Chemical formula 279】

(First Light Emitting Compound and Second Light Emitting Compound)

In the organic EL element 1B, the first light-emitting layer 51 also preferably further contains a first light-emitting compound (preferably a fluorescent compound).

In the organic EL element 1B, the second light-emitting layer 52 also preferably further contains a second light-emitting compound (preferably a fluorescent compound).

When the first light-emitting layer 51 contains a first light-emitting compound and the second light-emitting layer 52 contains a second light-emitting compound, the first light-emitting compound and the second light-emitting compound may be the same as or different from each other.

Examples of the first light-emitting compound and the second light-emitting compound include the same light-emitting compounds as exemplified in the organic EL element 1A.

In one embodiment, in the organic EL element 1B, at least one compound selected from the group consisting of the first light-emitting compound in the first light-emitting layer 51 and the second light-emitting compound in the second light-emitting layer 52 includes

The compound represented by the above general formula (4),

The compound represented by the above general formula (5),

The compound represented by the above general formula (6), and

One or more compounds selected from the group consisting of compounds represented by the above general formula (63a).

In one embodiment, the substituents in the above formulae when expressed as "substituted or unsubstituted" are

unsubstituted alkyl having 1 to 50 carbon atoms,

unsubstituted alkenyl having 2 to 50 carbon atoms,

unsubstituted alkynyl having 2 to 50 carbon atoms,

unsubstituted cycloalkyl having 3 to 50 ring carbon atoms,

-Si(R _901a )(R _902a )(R _903a ),

-O-(R _904a ),

-S-(R _905a ),

-N(R _906a )(R _907a ),

Halogen atoms,

Cyano,

Nitro,

unsubstituted aryl group having 6 to 50 ring carbon atoms, or

an unsubstituted heterocyclic group having 5 to 50 ring atoms,

R _901a to R _907a are each independently

Hydrogen atoms,

unsubstituted alkyl having 1 to 50 carbon atoms,

unsubstituted aryl group having 6 to 50 ring carbon atoms, or

an unsubstituted heterocyclic group having 5 to 50 ring atoms,

When there are two or more R _901a , the two or more R _901a are the same as or different from each other.

When there are two or more R _902a , the two or more R _902a are the same as or different from each other.

When there are two or more R _903a , the two or more R _903a are the same as or different from each other.

When there are two or more R _904a , the two or more R _904a are the same as or different from each other.

When there are two or more R _905a , the two or more R _905a are the same as or different from each other.

When there are two or more R _906a , the two or more R _906a are the same as or different from each other.

When there are two or more R _907a , the two or more R _907a are the same as or different from each other.

In one embodiment, the substituents in the above formulae when expressed as "substituted or unsubstituted" are

unsubstituted alkyl having 1 to 50 carbon atoms,

unsubstituted aryl group having 6 to 50 ring carbon atoms, or

An unsubstituted heterocyclic group having 5 to 50 ring atoms.

In one embodiment, the substituents in the above formulae when expressed as "substituted or unsubstituted" are

unsubstituted alkyl having 1 to 18 carbon atoms,

unsubstituted aryl group having 6 to 18 ring carbon atoms, or

An unsubstituted heterocyclic group having 5 to 18 ring atoms.

In the organic EL element 1B, the first light-emitting compound contained in the first light-emitting layer 51 is preferably a compound that emits light with a maximum peak wavelength of 500 nm or less, and more preferably a compound that emits light at 430 nm to 480 nm.

In the organic EL element 1B, the first light-emitting compound contained in the first light-emitting layer 51 is preferably a compound that emits fluorescence with a maximum peak wavelength of 500 nm or less, and more preferably a compound that emits fluorescence at a wavelength of 430 nm to 480 nm.

In the organic EL element 1B, the second light-emitting compound contained in the second light-emitting layer 52 is preferably a compound that emits light with a maximum peak wavelength of 500 nm or less, and more preferably a compound that emits light at 430 nm to 480 nm.

In the organic EL element 1B, the second light-emitting compound contained in the second light-emitting layer 52 is preferably a compound that emits fluorescence with a maximum peak wavelength of 500 nm or less, and more preferably a compound that emits fluorescence at a wavelength of 430 nm to 480 nm.

In the organic EL element 1B, when the first light-emitting layer 51 includes the first compound and the first light-emitting compound, the first compound is preferably a host material, and the first light-emitting compound is preferably a dopant material.

In the organic EL device 1B, the triplet energy T ₁ (H1) of the first compound and the triplet energy T ₁ (H2) of the second compound preferably satisfy the relationship of the following mathematical formula (Mathematical Formula 1).

T ₁ (H1)>T ₁ (H2)…(Formula 1)

In the past, Triplet-Triplet-Annihilation (sometimes referred to as TTA) has been known as a technology for improving the luminous efficiency of organic EL elements. TTA is a mechanism in which triplet excitons collide with triplet excitons to generate singlet excitons. It should be noted that, as described in International Publication No. 2010/134350, the TTA mechanism is sometimes also referred to as the TTF mechanism.

The TTF phenomenon is explained. Holes injected from the anode and electrons injected from the cathode recombine in the light-emitting layer to generate excitons. As is known in the past, the spin state is a ratio of 25% for singlet excitons and 75% for triplet excitons. In previously known fluorescent elements, 25% of singlet excitons emit light when they relax to the ground state, and the remaining 75% of triplet excitons do not emit light but return to the ground state through a thermal deactivation process. Therefore, it is said that the theoretical limit of the internal quantum efficiency of conventional fluorescent elements is 25%.

On the other hand, the behavior of triplet excitons generated inside organic matter has been studied theoretically. According to SM Bachilo et al. (J. Phys. Chem. A, 104, 7711 (2000)), if it is assumed that high-order excitons such as quintet state immediately return to triplet state, when the density of triplet excitons (hereinafter referred to as ³ A ^* ) gradually increases, triplet excitons collide with each other and a reaction shown in the following formula occurs. Here, ¹ A represents the ground state, and ¹ A ^* represents the lowest excited singlet exciton.

³ A*+ ³ A*→(4/9) ¹ A+(1/9) ¹ A*+(13/9) ³ A*

That is, it becomes 5 ³ A ^* →4 ¹ A + 1A ^* , and it is predicted that among the 75% of triplet excitons generated initially, 1/5, or 20%, will change to singlet excitons. Therefore, the singlet excitons that contribute in the form of light become 40%, which is obtained by adding 75% × (1/5) = 15% to the 25% generated initially. At this time, the ratio of light emission derived from TTF in the total light emission intensity (TTF ratio) becomes 15/40, or 37.5%. In addition, if the 75% of triplet excitons generated initially collide with each other to generate singlet excitons (2 triplet excitons generate 1 singlet exciton), a very high internal quantum efficiency of 62.5% can be obtained by adding 75% × (1/2) = 37.5% to the 25% of singlet excitons generated initially. At this time, the TTF ratio is 37.5/62.5 = 60%.

According to the organic EL element involved in this embodiment, it is considered that for triplet excitons generated by the recombination of holes and electrons in the first light-emitting layer, even if there are excess carriers at the interface between the first light-emitting layer and the directly connected organic layer, the triplet excitons present at the interface between the first light-emitting layer and the organic layer are not easily quenched. For example, in the case where the recombination region is locally present at the interface between the first light-emitting layer and the hole transport layer or the electron blocking layer, quenching caused by excess electrons can be considered. On the other hand, in the case where the recombination region is locally present at the interface between the first light-emitting layer and the electron transport layer or the hole blocking layer, quenching caused by excess holes can be considered.

The organic EL element 1B includes at least two light-emitting layers (i.e., a first light-emitting layer 51 and a second light-emitting layer 52) that satisfy a prescribed relationship. The triplet energy T ₁ (H1) of the first compound in the first light-emitting layer 51 and the triplet energy T ₁ (H2) of the second compound in the second light-emitting layer 52 are provided in such a manner as to satisfy the relationship of the above-mentioned mathematical formula (Mathematical Formula 1). The triplet excitons generated in the first light-emitting layer 51 are not quenched by excess carriers and move to the second light-emitting layer 52. In addition, the reverse movement from the second light-emitting layer 52 to the first light-emitting layer 51 can be suppressed. As a result, in the second light-emitting layer 52, the TTF mechanism is exhibited to efficiently generate singlet excitons, and the luminous efficiency is improved.

In this way, the organic EL element 1B has a first light-emitting layer 51 that mainly generates triplet excitons, and a second light-emitting layer 52 that effectively utilizes triplet excitons moved from the first light-emitting layer 51 and mainly exhibits the TTF mechanism as different regions. As the second compound in the second light-emitting layer 52, a compound having a smaller triplet energy than the first compound in the first light-emitting layer is used, and the triplet energy difference is set, thereby improving the luminous efficiency.

(Triplet energy T ₁ )

As a method for measuring the triplet energy T ₁ , the following method can be mentioned.

The compound to be measured was dissolved in EPA (diethyl ether: isopentane: ethanol = 5: 5: 2 (volume ratio)) to a concentration of 10 ^-5 mol/L or more and 10 ^-4 mol/L or less to prepare a solution, and the solution was added to a quartz colorimetric cell as a measurement sample. For the measurement sample, the phosphorescence spectrum was measured at a low temperature (77 [K]) (the vertical axis was the phosphorescence emission intensity, and the horizontal axis was the wavelength). For the rise tangent on the short wavelength side of the phosphorescence spectrum, the energy calculated based on the wavelength value λ _edge [nm] of the intersection of the tangent and the horizontal axis according to the following conversion formula (F1) was taken as the triplet energy T ₁ .

Conversion formula (F1): T ₁ [eV] = 1239.85/λ _edge

The tangent line for the rise of the short wavelength side of the phosphorescence spectrum is drawn as follows. When moving on the spectrum curve from the short wavelength side of the phosphorescence spectrum to the maximum value on the shortest wavelength side among the maximum values of the spectrum, the tangent line at each point on the curve is considered toward the long wavelength side. The slope of the tangent line increases as the curve rises (i.e., as the vertical axis increases). The tangent line drawn at the point where the slope value takes the maximum value (i.e., the tangent line at the inflection point) is used as the tangent line for the rise of the short wavelength side of the phosphorescence spectrum.

It should be noted that the maximum point with a peak intensity of less than 15% of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and the tangent drawn at the point where the slope value is the maximum value that is closest to the maximum value on the shortest wavelength side is used as the tangent of the rise on the short wavelength side of the phosphorescence spectrum.

Phosphorescence can be measured using a spectrofluorophotometer model F-4500 manufactured by Hitachi High-Technologies Co., Ltd. The measuring device is not limited thereto, and the measurement can be performed by combining a cooling device, a low-temperature container, an excitation light source, and a light receiving device.

In the organic EL element 1B, when the first light-emitting layer 51 contains the first compound and the first light-emitting compound, the singlet energy S ₁ (H1) of the first compound and the singlet energy S ₁ (D3) of the first light-emitting compound preferably satisfy the relationship expressed by the following equation (Equation 2).

S ₁ (H1)>S ₁ (D3)…(Formula 2)

(Singlet energy S1)

As a method for measuring the singlet energy _S1 using a solution (sometimes referred to as a solution method), the following method can be mentioned.

A toluene solution of the compound to be measured at 10 ^-5 mol/L or more and 10 ^-4 mol/L or less was prepared and added to a quartz colorimetric cell, and the absorption spectrum of the sample was measured at room temperature (300K) (the vertical axis was the absorption intensity, and the horizontal axis was the wavelength). A tangent line on the long wavelength side of the absorption spectrum was drawn, and the wavelength value λ _edge [nm] of the intersection of the tangent line and the horizontal axis was substituted into the conversion formula (F2) shown below to calculate the singlet energy S ₁ .

Conversion formula (F2): S ₁ [eV] = 1239.85/λedge

As an absorption spectrum measuring device, for example, a spectrophotometer manufactured by Hitachi, Ltd. (device name: U3310) can be cited, but the device is not limited thereto.

The tangent line for the long wavelength side of the absorption spectrum is drawn as follows. When moving along the long wavelength direction on the spectrum curve from the maximum value on the longest wavelength side among the maximum values of the absorption spectrum, the tangent line at each point on the curve is considered. As the curve falls (that is, as the value of the vertical axis decreases), the slope of the tangent line repeatedly decreases and then increases. The tangent line drawn at the point where the slope value is the minimum on the longest wavelength side (excluding the case where the absorbance is less than 0.1) is used as the tangent line for the long wavelength side of the absorption spectrum.

It should be noted that a maximum point where the absorbance value is 0.2 or less is not included in the above-mentioned maximum value on the longest wavelength side.

In the organic EL element 1B, when the second light-emitting layer 52 contains the second compound and the second light-emitting compound, the second compound is preferably a host material, and the second light-emitting compound is preferably a dopant material.

In the organic EL element 1B, when the second light-emitting layer 52 contains the second compound and the second light-emitting compound, the singlet energy S ₁ (H2) of the second compound and the singlet energy S ₁ (D4) of the second light-emitting compound preferably satisfy the relationship of the following formula (Formula 3).

S ₁ (H2)>S ₁ (D4)…(Formula 3)

It is preferred that the first light-emitting layer 51 and the second light-emitting layer 52 do not contain a phosphorescent material (dopant material).

In addition, the first light-emitting layer 51 and the second light-emitting layer 52 preferably do not contain a heavy metal complex and a phosphorescent rare earth metal complex. Here, examples of the heavy metal complex include an iridium complex, an osmium complex, and a platinum complex.

In addition, the first light-emitting layer 51 and the second light-emitting layer 52 also preferably do not contain a metal complex.

(Thickness of the light-emitting layer)

The thickness of the first light-emitting layer 51 and the second light-emitting layer 52 in the organic EL element 1B is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and further preferably 10 nm or more and 50 nm or less. If the thickness of the light-emitting layer is 5 nm or more, it is easy to form the light-emitting layer and easy to adjust the chromaticity. If the thickness of the light-emitting layer is 50 nm or less, it is easy to suppress the increase of the driving voltage.

(Content ratio of compound in light-emitting layer)

When the first light-emitting layer 51 contains the first compound and the first light-emitting compound, the contents of the first compound and the first light-emitting compound in the first light-emitting layer 51 are preferably in the following ranges, for example.

The content of the first compound is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less.

The content of the first light-emitting compound is preferably 1 mass % to 10 mass %, more preferably 1 mass % to 7 mass %, and even more preferably 1 mass % to 5 mass %.

However, the upper limit of the total content of the first compound and the first light-emitting compound in the first light-emitting layer 51 is 100 mass %.

It should be noted that this embodiment does not exclude the inclusion of materials other than the first compound and the first light-emitting compound in the first light-emitting layer 51 .

The first light-emitting layer 51 may contain only one kind of the first compound, or may contain two or more kinds of the first compound. The first light-emitting layer 51 may contain only one kind of the first light-emitting compound, or may contain two or more kinds of the first compound.

When the second light-emitting layer 52 contains the second compound and the second light-emitting compound, the contents of the second compound and the second light-emitting compound in the second light-emitting layer 52 are preferably in the following ranges, for example.

The content of the second compound is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and even more preferably 95% by mass or more and 99% by mass or less.

The content of the second light-emitting compound is preferably 1 mass % to 10 mass %, more preferably 1 mass % to 7 mass %, and even more preferably 1 mass % to 5 mass %.

However, the upper limit of the total content of the second compound and the second light-emitting compound in the second light-emitting layer 52 is 100 mass %.

It should be noted that this embodiment does not exclude the inclusion of materials other than the second compound and the second light-emitting compound in the second light-emitting layer 52 .

The second light-emitting layer 52 may contain only one type of the second compound, or may contain two or more types of the second compound. The second light-emitting layer 52 may contain only one type of the second light-emitting compound, or may contain two or more types of the second compound.

In the organic EL element 1B, it is also preferable that the first light-emitting layer 51 and the second light-emitting layer 52 are directly in contact with each other.

In the organic EL element 1B, when “the first light-emitting layer 51 and the second light-emitting layer 52 are directly in contact with each other”, the layer structure of “the first light-emitting layer 51 and the second light-emitting layer 52 are directly in contact with each other” may include any one of the following schemes (LS1), (LS2) and (LS3).

(LS1) A scheme in which a region in which a first compound as a main material (hereinafter sometimes referred to as "first main material") and a second compound as a main material (hereinafter sometimes referred to as "second main material") are mixed is generated during the vapor deposition process of the compound involved in the first light-emitting layer 51 and the vapor deposition process of the compound involved in the second light-emitting layer 52, and the region exists at the interface between the first light-emitting layer 51 and the second light-emitting layer 52.

(LS2) In the case where the first light-emitting layer 51 and the second light-emitting layer 52 contain light-emitting compounds, a region in which the first main material, the second main material and the light-emitting compound are mixed is generated during the vapor deposition process of the compound involved in the first light-emitting layer 51 and the vapor deposition process of the compound involved in the second light-emitting layer 52, and the region exists at the interface between the first light-emitting layer 51 and the second light-emitting layer 52.

(LS3) In the case where the first light-emitting layer 51 and the second light-emitting layer 52 contain light-emitting compounds, a region formed by the light-emitting compound, a region formed by the first main material, or a region formed by the second main material is generated during the vapor deposition process of the compound involved in the first light-emitting layer 51 and the vapor deposition process of the compound involved in the second light-emitting layer 52, and the region exists at the interface between the first light-emitting layer 51 and the second light-emitting layer 52.

When the organic EL element 1B includes a third light-emitting layer, it is preferred that the first light-emitting layer 51 and the second light-emitting layer 52 are directly in contact with each other, and the second light-emitting layer 52 and the third light-emitting layer are directly in contact with each other.

In the organic EL element 1B, when "the second light-emitting layer 52 is directly in contact with the third light-emitting layer", the layer structure of "the second light-emitting layer 52 is directly in contact with the third light-emitting layer" may include, for example, any one of the following schemes (LS4), (LS5) and (LS6).

(LS4) A scheme in which a region where the second main material and the third main material (the main material contained in the third light-emitting layer) are mixed is generated during the vapor deposition process of the compound involved in the second light-emitting layer 52 and the vapor deposition process of the compound involved in the third light-emitting layer, and the region exists at the interface between the second light-emitting layer 52 and the third light-emitting layer.

(LS5) In the case where the second light-emitting layer 52 and the third light-emitting layer contain light-emitting compounds, a region in which the second main material, the third main material and the light-emitting compound are mixed is generated during the vapor deposition process of the compound involved in the second light-emitting layer 52 and the vapor deposition process of the compound involved in the third light-emitting layer, and the region exists at the interface between the second light-emitting layer 52 and the third light-emitting layer.

(LS6) In the case where the second light-emitting layer 52 and the third light-emitting layer contain light-emitting compounds, a region formed by the light-emitting compound, a region formed by the second main material, or a region formed by the third main material is generated during the vapor deposition process of the compound involved in the second light-emitting layer 52 and the vapor deposition process of the compound involved in the third light-emitting layer, and the region exists at the interface between the second light-emitting layer 52 and the third light-emitting layer.

The organic EL element 1B also preferably further has an interlayer.

When the organic EL element 1B has an intervening layer, the intervening layer is preferably disposed between the first light-emitting layer 51 and the second light-emitting layer 52 .

(Interlayer)

The interlayer is preferably an undoped layer. The interlayer preferably does not contain metal atoms.

The interlayer comprises an interlayer material. The interlayer material is preferably not a light-emitting compound.

The interlayer material is not particularly limited, but is preferably a material other than a light-emitting compound.

Examples of interlayer materials include: 1) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, and phenanthroline derivatives; 2) carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, and the like; 3) Aromatic amine compounds such as triarylamine derivatives or condensed polycyclic aromatic amine derivatives.

The interlayer material may be one or both of the first compound contained in the first light-emitting layer 51 and the second compound contained in the second light-emitting layer 52 .

When the interlayer contains a plurality of interlayer materials, the content of each interlayer material is preferably 10% by mass or more of the total mass of the interlayer.

In the interlayer, the content of the above-mentioned interlayer material is preferably more than 60 mass % of the total mass of the interlayer, the content is more preferably more than 70 mass % of the total mass of the interlayer, the content is further preferably more than 80 mass % of the total mass of the interlayer, the content is further preferably more than 90 mass % of the total mass of the interlayer, and the content is particularly preferably more than 95 mass % of the total mass of the interlayer.

The interlayer may include only one interlayer material, or may include two or more interlayer materials.

When the interlayer contains two or more interlayer materials, the upper limit of the total content of the two or more interlayer materials is 100 mass %.

It should be noted that this embodiment does not exclude the inclusion of materials other than the interlayer material in the interlayer.

The interlayer may be composed of a single layer or a stack of two or more layers.

The thickness of the interlayer is not particularly limited, but is preferably 3 nm to 15 nm, and more preferably 5 nm to 10 nm, per layer.

The configuration of each layer common to the organic EL element 1A and the organic EL element 1B will be further described. In the following, reference numerals may be omitted.

(Substrate)

The substrate 2 is used as a support of the organic EL element. As the substrate 2, for example, glass, quartz, plastic, etc. can be used. In addition, a flexible substrate can be used. A flexible substrate refers to a (flexible) substrate that can be bent. For example, a plastic substrate can be mentioned. As materials forming the plastic substrate, for example, polycarbonate, polyarylate, polyether sulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, polyethylene naphthalate, etc. can be mentioned. In addition, an inorganic vapor-deposited film can also be used.

(anode)

The anode 3 formed on the substrate preferably uses a metal, alloy, conductive compound, and a mixture thereof with a large work function (specifically, 4.0 eV or more). Specifically, for example, indium oxide-tin oxide (ITO: IndiumTinOxide, indium tin oxide), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, graphene, etc. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti) or nitrides of metal materials (such as titanium nitride) can be cited.

These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target to which zinc oxide of 1 mass % or more and 10 mass % or less is added relative to indium oxide. In addition, for example, indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target containing 0.5 mass % or more and 5 mass % or less of tungsten oxide and 0.1 mass % or more and 1 mass % or less of zinc oxide relative to indium oxide. In addition, it can also be produced by vacuum evaporation, coating, inkjet, spin coating, etc.

Among the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that can easily inject holes regardless of the work function of the anode. Therefore, materials that can be used as electrode materials (such as metals, alloys, conductive compounds and mixtures thereof, and also including elements belonging to the first or second group of the periodic table) can be used.

It is also possible to use elements belonging to the first or second group of the periodic table as materials with a small work function, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing them (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing them. It should be noted that when using alkali metals, alkaline earth metals, and alloys containing them to form an anode, a vacuum evaporation method or a sputtering method can be used. In addition, when using silver paste, a coating method, an inkjet method, etc. can be used.

(cathode)

The cathode 4 preferably uses a metal, alloy, conductive compound, and a mixture thereof with a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to the first or second group of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), and alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys thereof (e.g., MgAg, AlLi), and rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys thereof.

It should be noted that when an alkali metal, an alkaline earth metal, or an alloy containing them is used to form the cathode, a vacuum deposition method or a sputtering method may be used. In addition, when a silver paste or the like is used, a coating method or an inkjet method may be used.

It should be noted that, by providing an electron injection layer, a cathode can be formed using various conductive materials such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, regardless of the size of the work function. These conductive materials can be formed into films using sputtering, inkjet, spin coating, etc.

(Hole Injection Layer)

The hole injection layer 61 is a layer containing a substance having high hole injectability. Examples of substances having high hole injectability include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.

In addition, as substances with high hole injection properties, low molecular weight organic compounds such as 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(4-diphenylaminophenyl)-N-phenylamino]biphenyl (abbreviation: DPAB), 4,4'-bis(N-{4-[N'-(3-methylphenyl)-N'-phenylamino]phenyl}-N-phenylamino)biphenyl (abbreviation: DNTPD), 1,3,5-tris[N-(4-diphenylaminophenyl)-N-phenylamino]phenyl] Aromatic amine compounds such as 3-[(1-phenyl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazole-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), 3-[N-(1-naphthyl)-N-(9-phenylcarbazole-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1), and dipyrazino[2,3-f:20,30-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN).

In addition, as a substance with high hole injection properties, a polymer compound (oligomer, dendrimer, polymer, etc.) can also be used. For example, poly (N-vinyl carbazole) (abbreviated as: PVK), poly (4-vinyl triphenylamine) (abbreviated as: PVTPA), poly [N- (4-{N'-[4-(4-diphenylamino) phenyl] phenyl-N'-phenylamino} phenyl) methacrylamide] (abbreviated as: PTPDMA), poly [N, N'-bis (4-butylphenyl) -N, N'-bis (phenyl) benzidine] (abbreviated as: Poly-TPD) and other polymer compounds can be mentioned. In addition, a polymer compound to which an acid is added, such as poly (3, 4-ethylenedioxythiophene) / poly (styrene sulfonic acid) (PEDOT / PSS), polyaniline / poly (styrene sulfonic acid) (PAni / PSS) and the like can also be used.

(Hole Transport Layer)

The hole transport layer 62 is a layer containing a substance with high hole transport properties. The hole transport layer 62 can use aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. Specifically, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviated as: NPB), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviated as: TPD), 4-phenyl-4'-(9-phenylfluorene-9-yl)triphenylamine (abbreviated as: BAFLP), 4,4'-bis[N-(9,9-dimethylfluorene-2-yl)-N -phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4"-tris(N,N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4"-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), 4,4'-bis[N-(spiro-9,9'-bifluorene-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) and the like. The substances described here are mainly substances having a hole mobility of 10 ^-6 cm ² /(V·s) or more.

Carbazole derivatives such as CBP, 9-[4-(N-carbazolyl)]phenyl-10-phenylanthracene (CzPA), 9-phenyl-3-[4-(10-phenyl-9-anthracenyl)phenyl]-9H-carbazole (PCzPA), and anthracene derivatives such as t-BuDNA, DNA, and DPAnth may also be used in the hole transport layer 62. Polymer compounds such as poly(N-vinylcarbazole) (abbreviated as PVK) and poly(4-vinyltriphenylamine) (abbreviated as PVTPA) may also be used.

It should be noted that any substance other than these may be used as long as it has a higher hole transport property than electrons. It should be noted that the layer containing a substance with a high hole transport property may be not only a single layer but also a stack of two or more layers formed of the above substances.

(Electron Transport Layer)

The electron transport layer 71 is a layer containing a substance with high electron transport properties. The electron transport layer 71 can use 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymer compounds. Specifically, as low-molecular organic compounds, metal complexes such as Alq, tris(4-methyl-8-hydroxyquinoline)aluminum (abbreviation: Almq ₃ ), bis(10-hydroxybenzo[h]quinoline)beryllium (abbreviation: BeBq ₂ ), BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition, in addition to the metal complex, heteroaromatic compounds such as 2-(4-biphenyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazole-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenyl)-1,2,4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs) can also be used. In this embodiment, a benzimidazole compound can be suitably used. The substances described here are mainly substances with an electron mobility of ^{10-6 cm2} /(V·s) or more. It should be noted that as long as the electron transport property is higher than the hole transport property, substances other than the above can also be used as the electron transport layer. In addition, the electron transport layer can also be composed of a single layer or a stack of two or more layers formed by the above substances.

In addition, a polymer compound may be used in the electron transport layer 71. For example, poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviated as PF-Py), poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviated as PF-BPy), etc. may be used.

(Electron Injection Layer)

The electron injection layer 72 is a layer containing a substance with high electron injection properties. Alkali metals, alkaline earth metals, or compounds thereof such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), and lithium oxide (LiOx) can be used in the electron injection layer 72. In addition, a material obtained by adding an alkali metal, an alkaline earth metal, or a compound thereof to a substance having electron transport properties can also be used. Specifically, a material obtained by adding magnesium (Mg) to Alq can be used. It should be noted that electron injection from the cathode can be performed more efficiently at this time.

Alternatively, a composite material mixed with an organic compound and an electron donor (donor) can also be used in the electron injection layer 72. Such a composite material has excellent electron injection and electron transport properties because electrons are generated in the organic compound by the electron donor. At this time, as an organic compound, it is preferably a material with excellent transmission of the generated electrons. Specifically, for example, the above-mentioned substances (metal complexes, heteroaromatic compounds, etc.) constituting the electron transport layer can be used. As an electron donor, it is a substance that shows electron donating properties for organic compounds. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and lithium, cesium, magnesium, calcium, erbium, ytterbium, etc. can be cited. In addition, alkali metal oxides and alkaline earth metal oxides are preferred, and lithium oxide, calcium oxide, barium oxide, etc. can be cited. In addition, a Lewis base such as magnesium oxide can also be used. In addition, organic compounds such as tetrathiafulvalene (abbreviated as: TTF) can also be used.

(Layer Formation Method)

The method for forming each layer of the organic EL element of this embodiment is not limited except for those specifically mentioned above, and known methods such as dry film forming methods such as vacuum evaporation, sputtering, plasma, and ion plating, and wet film forming methods such as spin coating, immersion, flow coating, and inkjet can be used.

(Film Thickness)

The thickness of each organic layer of the organic EL element of this embodiment is not limited except for the cases specifically mentioned above. Generally speaking, if the film thickness is too thin, defects such as pinholes are easily generated, and if the film thickness is too thick, a high applied voltage is required, and the efficiency is deteriorated. Therefore, the film thickness of each organic layer of the organic EL element is preferably in the range of several nm to 1 μm.

According to this embodiment, an organic electroluminescent element having an improved life can be provided.

[Fifth Embodiment]

(Electronic equipment)

The electronic device involved in this embodiment is equipped with any of the organic EL elements in the above-mentioned embodiments. As electronic devices, for example, display devices and light-emitting devices can be cited. As display devices, for example, display components (such as organic EL panel modules, etc.), televisions, mobile phones, tablet computers, and personal computers can be cited. As light-emitting devices, for example, lighting and vehicle lamps can be cited.

[Variations of Embodiments]

It should be noted that the present invention is not limited to the above-described embodiments, and modifications, improvements, etc. within the scope that can achieve the object of the present invention are included in the present invention.

For example, the light-emitting layer is not limited to 1 or 2 layers, and a plurality of light-emitting layers exceeding 2 may be stacked. In the case where the organic EL element has a plurality of light-emitting layers exceeding 2, for example, other light-emitting layers other than the light-emitting layers described in the above-mentioned embodiments may be fluorescent light-emitting layers, or phosphorescent light-emitting layers utilizing light emission based on electron transition directly from a triplet excited state to a ground state.

When the organic EL element has a plurality of light-emitting layers, these light-emitting layers may be provided adjacent to each other, or a so-called tandem type organic EL element may be formed by stacking a plurality of light-emitting units with intervening spaces therebetween.

In addition, for example, a blocking layer may be provided adjacent to at least one of the anode side and the cathode side of the light-emitting layer. The blocking layer is preferably disposed in contact with the light-emitting layer to block at least any one of holes, electrons, and excitons.

For example, when a blocking layer is disposed in contact with the cathode side of the light-emitting layer, the blocking layer transports electrons and prevents holes from reaching a layer (e.g., an electron transport layer) that is closer to the cathode side than the blocking layer. When an organic EL element includes an electron transport layer, the blocking layer is preferably included between the light-emitting layer and the electron transport layer.

In addition, when a blocking layer is disposed in contact with the anode side of the light-emitting layer, the blocking layer transports holes and prevents electrons from reaching a layer (e.g., a hole transport layer) that is closer to the anode side than the blocking layer. When the organic EL element includes a hole transport layer, it is preferred that the blocking layer be included between the light-emitting layer and the hole transport layer.

In order to prevent the excitation energy from leaking from the light-emitting layer to its peripheral layers, a blocking layer may be provided adjacent to the light-emitting layer to prevent the excitons generated in the light-emitting layer from moving to layers closer to the electrode side than the blocking layer (e.g., electron transport layer and hole transport layer).

It is preferred that the light-emitting layer is in contact with the blocking layer.

In addition, the specific structure and shape in the implementation of the present invention may be set to other structures and the like within the scope that can achieve the purpose of the present invention.

Example

The present invention is further described in detail below with reference to examples, but the present invention is not limited to these examples.

<Compound>

The structures of the compound represented by the general formula (1C) and the compound represented by the general formula (1C-B) used in the production of the organic EL device according to the Examples are shown below.

【Chemical Formula 280】

【Chemical Formula 281】

The structures of the compound represented by the general formula (1C), the compound represented by the general formula (1C-A), and the compound represented by the general formula (1C-B) used in the production of the organic EL device according to the Examples are shown below.

【Chemical formula 282】

The structures of the compound represented by the general formula (1C), the compound represented by the general formula (1C-B), and the compound represented by the general formula (1C-C) used in the production of the organic EL device according to the Examples are shown below.

【Chemical formula 283】

The structures of comparative compounds used in the production of organic EL devices according to Comparative Examples are shown below.

【Chemical formula 284】

The structures of other compounds used in the organic EL devices according to Examples and Comparative Examples are shown below.

【Chemical formula 285】

【Chemical formula 286】

【Chemical formula 287】

<Fabrication of Organic EL Devices>

An organic EL device was produced and evaluated as follows.

[Example 1-1]

A 25 mm x 75 mm x 1.1 mm thick glass substrate with an ITO (Indium Tin Oxide) transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The thickness of the ITO transparent electrode was 130 nm.

The cleaned glass substrate with transparent electrode lines was mounted on a substrate holder of a vacuum deposition device, and compound HIL-1 was first deposited on the surface on which the transparent electrode lines were formed so as to cover the transparent electrode, thereby forming a hole injection layer (HI) with a thickness of 5 nm.

After the hole injection layer was formed, compound HTL-1 was evaporated to form a first hole transport layer with a film thickness of 80 nm.

After the formation of the first hole transport layer, compound EBL-1 was evaporated to form a second hole transport layer (also referred to as an electron blocking layer) with a film thickness of 10 nm.

Compound BH1-1 as the first compound and compound BD-1 as the first luminescent compound were co-evaporated on the second hole transport layer so that the proportion of compound BH1-1 was 98 mass % and the proportion of compound BD-1 was 2 mass %, forming a first luminescent layer with a film thickness of 12.5 nm.

Compound BH-2 as the second compound and compound BD-1 as the second luminescent compound were co-evaporated on the first luminescent layer so that the ratio of compound BH-2 was 98 mass % and the ratio of compound BD-1 was 2 mass %, forming a second luminescent layer with a film thickness of 12.5 nm.

Compound aET-1 was evaporated on the second light-emitting layer to form a first electron transport layer (also referred to as a hole blocking layer) with a thickness of 10 nm.

Compound bET-1 was evaporated on the first electron transport layer to form a second electron transport layer with a thickness of 15 nm.

LiF was evaporated on the second electron transport layer to form an electron injection layer with a thickness of 1 nm.

Metal Al was evaporated on the electron injection layer to form a cathode with a film thickness of 80 nm.

The component configuration of Example 1-1 is shown in simplified form as follows.

ITO(130)/HIL-1(5)/HTL-1(80)/EBL-1(10)/BH1-1: BD-1 (12.5, 98%: 2%)/BH-2: BD-1 (12.5, 98%: 2%)/aET-1(10)/bET-1(15)/LiF(1)/Al(80)

In addition, the numbers in parentheses represent film thickness (unit: nm).

Similarly, the numbers expressed as percentages in parentheses (98%:2%) represent the ratio (mass %) of compound BH1-1 or compound BH-2 to compound BD-1 in the first light-emitting layer or the second light-emitting layer.

[Example 1-2 to Example 1-10]

The organic EL devices of Examples 1-2 to 1-10 were each produced in the same manner as in Example 1-1, except that the first compound of the first light-emitting layer was changed to a compound described in Table 1.

[Comparative Example 1-1]

The organic EL device of Comparative Example 1-1 was produced in the same manner as in Example 1-1, except that the first compound of the first light-emitting layer was changed to the compound described in Table 1.

[Example 2-1]

A 25 mm x 75 mm x 1.1 mm thick glass substrate with an ITO (Indium Tin Oxide) transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The thickness of the ITO transparent electrode was 130 nm.

The cleaned glass substrate with transparent electrode lines is installed on the substrate frame of the vacuum evaporation device. First, compound HTL-2 and compound HIL-2 are co-evaporated on the surface on the side where the transparent electrode lines are formed in a manner to cover the transparent electrode so that the proportion of compound HTL-2 is 90 mass% and the proportion of compound HIL-2 is 10 mass%, thereby forming a hole injection layer (HI) with a film thickness of 10 nm.

After the hole injection layer was formed, the compound HTL-2 was evaporated to form a first hole transport layer with a film thickness of 85 nm.

After the formation of the first hole transport layer, compound EBL-2 was evaporated to form a second hole transport layer (also referred to as an electron blocking layer) with a film thickness of 5 nm.

Compound BH1-1 as the first compound and compound BD-2 as the first luminescent compound were co-evaporated on the second hole transport layer so that the proportion of compound BH1-1 was 98 mass % and the proportion of compound BD-2 was 2 mass %, thereby forming a first luminescent layer with a thickness of 10 nm.

Compound BH-2-4 as the second compound and compound BD-2 as the second luminescent compound were co-evaporated on the first luminescent layer so that the ratio of compound BH-2-4 was 98 mass % and the ratio of compound BD-2 was 2 mass %, forming a second luminescent layer with a film thickness of 10 nm.

Compound aET-2 was evaporated on the second light-emitting layer to form a first electron transport layer (also referred to as a hole blocking layer) with a thickness of 5 nm.

Compound bET-2 and compound Liq were co-evaporated on the first electron transport layer so that the ratio of compound bET-2 was 50% by mass and the ratio of compound Liq was 50% by mass, forming an electron transport layer with a film thickness of 25 nm. Liq is the abbreviation of (8-quinolinolato)lithium.

Liq was vapor-deposited on the second electron transport layer to form an electron injection layer having a film thickness of 1 nm.

Metal Al was evaporated on the electron injection layer to form a cathode with a film thickness of 80 nm.

The component structure of Example 2-1 is shown in simplified form as follows.

ITO(130)/HTL-2:HIL-2(10,90%:10%)/HTL-2(85)/EBL-2(5)/BH1-1:BD-2(10,98%:2 %)/BH-2-4: BD-2 (10, 98%: 2%)/aET-2 (5)/bET-2: Liq (25, 50%: 50%)/Liq (1)/Al (80)

In addition, the numbers in parentheses represent film thickness (unit: nm).

Similarly, the numbers expressed as percentages in parentheses (90%:10%) indicate the ratio (mass %) of the compound HTL-2 to the compound HIL-2.

Similarly, the numbers expressed as percentages in parentheses (98%:2%) represent the ratio (mass %) of compound BH1-1 or compound BH-2-4 to compound BD-2 in the first light-emitting layer or the second light-emitting layer.

[Example 2-2 to Example 2-4]

Each of the organic EL devices of Examples 2-2 to 2-4 was produced in the same manner as in Example 2-1, except that the first compound of the first light-emitting layer was changed to a compound described in Table 2.

[Comparative Example 2-1]

The organic EL device of Comparative Example 2-1 was produced in the same manner as in Example 2-1, except that the first compound of the first light-emitting layer was changed to the compound described in Table 2.

[Example 3-1]

A 25 mm x 75 mm x 1.1 mm thick glass substrate with an ITO (Indium Tin Oxide) transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The thickness of the ITO transparent electrode was 130 nm.

The cleaned glass substrate with transparent electrode lines is installed on the substrate frame of the vacuum evaporation device. First, compound HTL-2 and compound HIL-2 are co-evaporated on the surface on the side where the transparent electrode lines are formed in a manner to cover the transparent electrode so that the proportion of compound HTL-2 is 90 mass% and the proportion of compound HIL-2 is 10 mass%, thereby forming a hole injection layer (HI) with a film thickness of 10 nm.

After the hole injection layer was formed, the compound HTL-2 was evaporated to form a first hole transport layer with a film thickness of 85 nm.

After the formation of the first hole transport layer, compound EBL-2 was evaporated to form a second hole transport layer (also referred to as an electron blocking layer) with a film thickness of 5 nm.

On the second hole transport layer, compound BH1-1 as the first compound and compound BD-3 as the first luminescent compound were co-evaporated so that the ratio of compound BH1-1 was 98 mass % and the ratio of compound BD-3 was 2 mass %, forming a first luminescent layer with a thickness of 10 nm.

Compound BH-2-4 as the second compound and compound BD-3 as the second luminescent compound were co-evaporated on the first luminescent layer so that the ratio of compound BH-2-4 was 98 mass % and the ratio of compound BD-3 was 2 mass %, thereby forming a second luminescent layer with a film thickness of 10 nm.

Compound aET-2 was evaporated on the second light-emitting layer to form a first electron transport layer (also referred to as a hole blocking layer) with a thickness of 5 nm.

On the first electron transport layer, compound bET-2 and compound Liq were co-evaporated so that the ratio of compound bET-2 was 50 mass % and the ratio of compound Liq was 50 mass %, thereby forming an electron transport layer with a film thickness of 25 nm.

Liq was vapor-deposited on the second electron transport layer to form an electron injection layer having a film thickness of 1 nm.

Metal Al was evaporated on the electron injection layer to form a cathode with a film thickness of 80 nm.

The component structure of Example 3-1 is shown in simplified form as follows.

ITO(130)/HTL-2:HIL-2(10,90%:10%)/HTL-2(85)/EBL-2(5)/BH1-1:BD-3(10,98%:2 %)/BH-2-4: BD-3 (10, 98%: 2%)/aET-2 (5)/bET-2: Liq (25, 50%: 50%)/Liq (1)/Al (80)

In addition, the numbers in parentheses represent film thickness (unit: nm).

Similarly, the numbers expressed as percentages in parentheses (90%:10%) indicate the ratio (mass %) of the compound HTL-2 to the compound HIL-2.

Similarly, the numbers expressed as percentages in parentheses (98%:2%) represent the ratio (mass %) of compound BH1-1 or compound BH-2-4 to compound BD-3 in the first light-emitting layer or the second light-emitting layer.

[Example 3-2 to Example 3-4]

The organic EL devices of Examples 3-2 to 3-4 were each produced in the same manner as in Example 3-1, except that the first compound of the first light-emitting layer was changed to a compound described in Table 3.

[Comparative Example 3-1]

The organic EL device of Comparative Example 3-1 was produced in the same manner as in Example 3-1, except that the first compound of the first light-emitting layer was changed to the compound described in Table 3.

<Evaluation of Organic EL Devices>

The organic EL devices produced in Examples 1-1 to 1-10, Examples 2-1 to 2-4, Examples 3-1 to 3-4, and Comparative Examples 1-1, 2-1, and 3-1 were evaluated as follows.

Lifespan (LT95)

A voltage was applied to the obtained organic EL device so that the current density was 50 mA/cm ² , and the time until the luminance reached 95% of the initial luminance (LT95 (unit: hours)) was measured. The luminance was measured using a spectrophotometer CS-2000 (manufactured by Konica Minolta Co., Ltd.).

Table 1 shows the measured values of LT95 of each example (Example 1-1 to Example 1-10 and Comparative Example 1-1) and "LT95 (relative value)" (unit: %) calculated by the following mathematical formula (Mathematical formula 1X). LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 1-1) × 100 ... (Mathematical formula 1X)

Table 2 shows the measured values of LT95 of each example (Example 2-1 to Example 2-4 and Comparative Example 2-1) and "LT95 (relative value)" (unit: %) calculated by the following mathematical formula (Mathematical formula 2X). LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 2-1) × 100 ... (Mathematical formula 2X)

Table 3 shows the measured values of LT95 of each example (Example 3-1 to Example 3-4 and Comparative Example 3-1) and "LT95 (relative value)" (unit: %) calculated by the following mathematical formula (Mathematical formula 3X). LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 3-1) × 100 ... (Mathematical formula 3X)

【Table 1】

【Table 2】

【Table 3】

The organic EL elements of Examples 1-1 to 3-4 using the compound represented by the general formula (1C-A), the compound represented by the general formula (1C-B), the compound represented by the general formula (1C-C) and the compound represented by the general formula (1C) have a longer lifespan than the organic EL elements of Comparative Examples 1-1 to 3-1.

<Evaluation of Compounds>

(Triplet energy T ₁ )

The compound to be measured was dissolved in EPA (diethyl ether: isopentane: ethanol = 5: 5: 2 (volume ratio)) to a concentration of 10 μmol/L to prepare a solution, and the solution was added to a quartz colorimetric cell as a measurement sample. For the measurement sample, the phosphorescence spectrum was measured at a low temperature (77 [K]) (the vertical axis was set to phosphorescence emission intensity, and the horizontal axis was set to wavelength). For the rise tangent on the short wavelength side of the phosphorescence spectrum, the energy calculated based on the wavelength value λ _edge [nm] of the intersection of the tangent and the horizontal axis according to the following conversion formula (F1) was taken as the triplet energy T _1. The results are shown in Tables 1 and 2.

It should be noted that the triplet energy _T1 may have an error of about 0.02 eV depending on the measurement conditions.

Conversion formula (F1): T ₁ [eV] = 1239.85/λ _edge

The tangent line for the rise of the short wavelength side of the phosphorescence spectrum is drawn as follows. When moving on the spectrum curve from the short wavelength side of the phosphorescence spectrum to the maximum value on the shortest wavelength side among the maximum values of the spectrum, the tangent line at each point on the curve is considered toward the long wavelength side. The slope of the tangent line increases as the curve rises (that is, as the vertical axis increases). The tangent line drawn at the point where the slope value takes the maximum value (that is, the tangent line at the inflection point) is used as the tangent line for the rise of the short wavelength side of the phosphorescence spectrum.

It should be noted that the maximum point with a peak intensity of less than 15% of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and the tangent drawn at the point where the slope value is the maximum value that is closest to the maximum value on the shortest wavelength side is used as the tangent of the rise on the short wavelength side of the phosphorescence spectrum.

For the measurement of phosphorescence, a spectrofluorophotometer model F-4500 manufactured by Hitachi High-Technologies Corporation was used.

(Singlet energy S ₁ )

A 10 μmol/L toluene solution of the compound to be measured was prepared and added to a quartz colorimetric cell, and the absorption spectrum of the sample was measured at room temperature (300K) (the vertical axis is the absorption intensity, and the horizontal axis is the wavelength). For the downward tangent line on the long wavelength side of the absorption spectrum, the wavelength value λedge [nm] of the intersection of the tangent line and the horizontal axis was substituted into the conversion formula (F2) shown below to calculate the singlet energy S ₁ . The results are shown in Tables 1 and 2.

Conversion formula (F2): S ₁ [eV] = 1239.85/λedge

As an absorption spectrum measuring apparatus, a spectrophotometer manufactured by Hitachi, Ltd. (apparatus name: U3310) was used.

The tangent line for the long wavelength side of the absorption spectrum is drawn as follows. When moving along the long wavelength direction on the spectrum curve from the maximum value on the longest wavelength side among the maximum values of the absorption spectrum, the tangent line at each point on the curve is considered. As the curve falls (that is, as the value of the vertical axis decreases), the slope of the tangent line repeatedly decreases and then increases. The tangent line drawn at the point where the slope value is the minimum on the longest wavelength side (excluding the case where the absorbance is less than 0.1) is used as the tangent line for the long wavelength side of the absorption spectrum.

It should be noted that a maximum point where the absorbance value is 0.2 or less is not included in the above-mentioned maximum value on the longest wavelength side.

(Maximum peak wavelength of the compound)

The maximum peak wavelength λ of the compound is measured by the following method.

A 5 μmol/L toluene solution of the compound to be measured is prepared and added to a quartz colorimetric cell, and the luminescence spectrum of the sample is measured at room temperature (300K) (the vertical axis is set as the luminescence intensity, and the horizontal axis is set as the wavelength). In this embodiment, the luminescence spectrum is measured using a spectrofluorophotometer (device name: F-7000) manufactured by Hitachi High-Tech Scientific Co., Ltd. It should be noted that the luminescence spectrum measuring device is not limited to the device used here. In the luminescence spectrum, the peak wavelength of the luminescence spectrum with the maximum luminescence intensity is set to the maximum peak wavelength λ.

The maximum peak wavelength λ of compound BD-1 is 452 nm.

The maximum peak wavelength λ of the compound BD-2 is 455 nm.

The maximum peak wavelength λ of the compound BD-3 is 457 nm.

<Synthesis of Compounds>

[Synthesis Example 1: Synthesis of Compound BH1-1]

Compound BH1-1 was synthesized using the following synthetic route.

【Chemical formula 288】

(Synthesis of Compound BH1-1)

Under an argon atmosphere, 5.44 g (20.0 mmol) of intermediate 1-A, 5.62 g (20.0 mmol) of intermediate 1-B, 0.46 g (0.4 mmol) of diAmphos palladium dichloride (2), 30.0 ml (60.0 mmol) of 2M sodium carbonate aqueous solution and 1,2-dimethoxyethane (100 ml) were placed in a flask and heated under reflux with stirring for 8 hours. After stirring, the mixture was cooled to room temperature (25° C.), and the solvent was then distilled off. The obtained solid was purified by silica gel chromatography to obtain 5.4 g (yield 63%) of a white solid.

The white solid was identified as compound BH1-1 by LC-MS analysis (liquid chromatography mass spectrometry).

[Synthesis Example 2: Synthesis of Compound BH1-3]

Compound BH1-3 was synthesized using the following synthetic route.

【Chemical formula 289】

(Synthesis of Intermediate 3-B)

In the synthesis of compound BH1-1, intermediate 3-B was synthesized by the same method as the synthesis method of compound BH1-1, except that intermediate 3-A and phenylboronic acid were used instead of intermediate 1-A and intermediate 1-B, to obtain 7.0 g (yield 87%) of a white solid.

The white solid was identified as Intermediate 3-B by LC-MS analysis (liquid chromatography mass spectrometry).

【Chemical formula 290】

(Synthesis of Intermediate 3-C)

Under an argon atmosphere, 7.0 g (23.0 mmol) of intermediate 3-B, 4.1 g (23.0 mmol) of N-bromosuccinimide (NBS) and 115 ml of dichloromethane were placed in a flask and stirred and heated under reflux for 48 hours. After cooling to room temperature (25°C), the solvent was distilled off and the obtained residue was purified by silica gel chromatography to obtain 5.6 g (yield 64%) of a white solid.

The white solid was identified as Intermediate 3-C by LC-MS analysis (liquid chromatography mass spectrometry).

【Chemical formula 291】

(Synthesis of Compound BH1-3)

In the synthesis of compound BH1-1, except that intermediates 3-C and 3-D were used instead of intermediates 1-A and 1-B, compound BH1-3 was synthesized by the same method as the synthesis method of compound BH1-1 to obtain 0.6 g of a light yellow solid (yield 25%).

The pale yellow solid was identified as compound BH1-3 by LC-MS analysis (liquid chromatography mass spectrometry).

[Synthesis Example 3: Synthesis of Compound BH1-4]

Compound BH1-4 was synthesized using the following synthetic route.

【Chemical formula 292】

(Synthesis of Compound BH1-4)

Under an argon atmosphere, compound BH1-3: 5.7 g (11.3 mmol) and o-dichlorobenzene: 100 ml were placed in a flask, and after being completely dissolved while stirring at room temperature, benzene-d6: 50 ml was added, and stirred at 10°C for 5 minutes. Then, trifluoromethanesulfonic acid: 1.99 ml (22.5 mmol) was added, and stirred at 10°C for 2 hours. Then, heavy water 200 ml was added, and stirred for further 15 minutes. After stirring, the water layer was removed and the remaining organic layer was concentrated. The obtained solid was purified by silica gel chromatography to obtain 0.5 g of a light yellow solid (yield 24%).

The pale yellow solid was identified as compound BH1-4 by LC-MS analysis (liquid chromatography mass spectrometry).

[Synthesis Example 4: Synthesis of Compound BH1-5]

Compound BH1-5 was synthesized using the following synthetic route.

【Chemical formula 293】

(Synthesis of Compound BH1-5)

Compound BH1-1 was synthesized by the same method as compound BH1-1 except that intermediates 3-C and 5-D were used instead of intermediates 1-A and 1-B to obtain 0.9 g (yield 47%) of a pale yellow solid.

The pale yellow solid was identified as compound BH1-5 by LC-MS analysis (liquid chromatography mass spectrometry).

[Synthesis Example 5: Synthesis of Compound BH1-6]

Compound BH1-6 was synthesized using the following synthetic route.

【Chemical formula 294】

(Synthesis of Compound BH1-6)

Compound BH1-1 was synthesized by the same method as that of compound BH1-1 except that intermediates 3-C and 6-D were used instead of intermediates 1-A and 1-B to obtain 1.1 g (yield 49%) of a pale yellow solid.

The pale yellow solid was identified as compound BH1-6 by LC-MS analysis (liquid chromatography mass spectrometry).

[Synthesis Example 6: Synthesis of Compound BH1-7]

Compound BH1-7 was synthesized using the following synthetic route.

【Chemical formula 295】

(Synthesis of Intermediate 7-B)

Under argon atmosphere, intermediate 7-A: 11.6g (43.2mmol) and dichloromethane: 215ml were put into a flask. After the solution was cooled to 0°C, pyridine: 4.4ml (56.1mmol) was added dropwise to the system. Then, trifluoromethanesulfonic anhydride: 9.2ml (56.1mmol) was added dropwise to the system and stirred directly for 1 hour.

After stirring for 6 hours while returning to room temperature (25°C), ice water was added to the reaction solution, the aqueous layer was removed after sufficient stirring, the remaining organic layer was concentrated, and the residue was purified by silica gel chromatography to obtain 21.3 g of a white solid (yield 73%).

The white solid was identified as Intermediate 7-B by LC-MS analysis (liquid chromatography mass spectrometry).

(Synthesis of Intermediate 7-D)

Compound BH1-1 was synthesized by the same method as that of compound BH1-1 except that intermediates 7-B and 7-C were used instead of intermediates 1-A and 1-B to obtain 19.3 g (yield 87%) of a white solid.

The white solid was identified as Intermediate 7-D by LC-MS analysis (liquid chromatography mass spectrometry).

(Synthesis of Intermediate 7-E)

Under an argon atmosphere, (methoxymethyl) triphenylphosphonium chloride: 28.1g, tetrahydrofuran: 130ml were put into a flask and stirred for 5 minutes, then tert-butoxide potassium 1mol/L tetrahydrofuran solution: 82ml was added and stirred at room temperature for 1.5 hours. Then, a solution of intermediate 7-D: 21.1g dissolved in tetrahydrofuran: 342ml was added to the system and stirred at room temperature for 3 hours. After that, the precipitated solid was filtered and the filtrate was concentrated. The obtained residue was purified by silica gel chromatography to obtain 22.5g of a white solid (yield 98%).

The white solid was identified as Intermediate 7-E by LC-MS analysis (liquid chromatography mass spectrometry).

(Synthesis of Intermediate 7-F)

Under an argon atmosphere, 22.5 g of intermediate 7-E and 684 ml of dichloromethane were placed in a flask and stirred at 0°C for 5 minutes. Then, 7 ml of methanesulfonic acid was added and stirred at 0°C for 3 hours. After that, the mixture was washed with a saturated sodium bicarbonate aqueous solution, the aqueous layer was removed, and the organic layer was concentrated. The obtained residue was purified by silica gel chromatography to obtain 9.4 g of a white solid (yield 45%).

The white solid was identified as Intermediate 7-F by LC-MS analysis (Liquid Chromatography Mass Spectrometry).

(Synthesis of Intermediate 7-G)

Under argon atmosphere, intermediate 7-F: 6.5 g (19.8 mmol), bis(pinacolato)diboron 10.0 g (39.5 mmol), palladium (II) acetate: 0.09 g (0.4 mmol), XPhos: 0.75 g (1.6 mmol), potassium acetate 5.82 g (59.3 mmol) and 1,4-dioxane 100 mL were added to a flask and stirred at 100 ° C for 7 hours. After stirring, it was cooled to room temperature. After cooling, the organic layer was washed with saturated brine and dried by adding sodium sulfate. After drying, it was filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography to obtain 5.7 g of a white solid (yield 41%).

The white solid was identified as Intermediate 7-G by LC-MS analysis (liquid chromatography mass spectrometry).

(Synthesis of Compound BH1-7)

Compound BH1-1 was synthesized by the same method as compound BH1-1 except that intermediates 7-G and 7-H were used instead of intermediates 1-A and 1-B to obtain 1.9 g (yield 25%) of a pale yellow solid.

The pale yellow solid was identified as compound BH1-7 by LC-MS analysis (liquid chromatography mass spectrometry).

[Synthesis Example 7: Synthesis of Compound BH1-8]

Compound BH1-8 was synthesized using the following synthetic route.

【Chemical formula 296】

(Synthesis of Compound BH1-8)

Compound BH1-4 was synthesized by the same method as that of compound BH1-4 except that compound BH1-7 was used instead of compound BH1-3, thereby obtaining 0.2 g (yield 43%) of a light yellow solid.

The pale yellow solid was identified as compound BH1-8 by LC-MS analysis (liquid chromatography mass spectrometry).

[Synthesis Example 8: Synthesis of Compound BH1-9]

Compound BH1-9 was synthesized using the following synthetic route.

【Chemical formula 297】

(Synthesis of Compound BH1-9)

Compound BH1-1 was synthesized by the same method as that of compound BH1-1 except that intermediates 3-A and 6-D were used instead of intermediates 1-A and 1-B to obtain 3.4 g (yield 82%) of a pale yellow solid.

The pale yellow solid was identified as compound BH1-9 by LC-MS analysis (liquid chromatography mass spectrometry).

[Synthesis Example 9: Synthesis of Compound BH1-10]

Compound BH1-10 was synthesized using the following synthetic route.

【Chemical formula 298】

(Synthesis of Compound BH1-10)

Compound BH1-1 was synthesized by the same method as that of compound BH1-1 except that intermediates 3-A and 10-D were used instead of intermediates 1-A and 1-B to obtain 2.2 g (yield 77%) of a pale yellow solid.

The pale yellow solid was identified as compound BH1-10 by LC-MS analysis (liquid chromatography mass spectrometry).

[Synthesis Example 10: Synthesis of Compound BH1-11]

Compound BH1-11 was synthesized using the following synthetic route.

【Chemical formula 299】

(Synthesis of Compound BH1-11)

Compound BH1-1 was synthesized by the same method as that of compound BH1-1 except that intermediates 3-C and 10-D were used instead of intermediates 1-A and 1-B to obtain 1.7 g (yield 40%) of a pale yellow solid.

The pale yellow solid was identified as compound BH1-11 by LC-MS analysis (liquid chromatography mass spectrometry).

Explanation of symbols

1A, 1B...organic EL element, 2...substrate, 3...anode, 4...cathode, 5A, 5B...light-emitting region, 5...light-emitting layer, 51...first light-emitting layer, 52...second light-emitting layer, 6...hole transport region, 61...hole injection layer, 62...hole transport layer, 7...electron transport region, 71...electron transport layer, 72...electron injection layer.

Claims (89)

1. A compound represented by the following general formula (1C-A), In the general formula (1C-A), One of R ₄ to R ₈ and R ₁₀ to R ₁₂ is a group represented by the general formula (1D-A), R ₁ to R ₃ , R ₉ , and R ₄ to R ₈ and R ₁₀ to R ₁₂ other than the group represented by the general formula (1D-A) are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ), -O-(R ₉₀₄ ), -S-(R ₉₀₅ ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R ₈₀₁ , -COOR ₈₀₂ , Halogen atoms, Cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, When R ₁₁ is a group represented by the general formula (1D-A), R ₁₂ is a hydrogen atom or a substituted or unsubstituted phenyl group, When R ₁₂ is a group represented by the general formula (1D-A), R ₁₁ is a hydrogen atom or a substituted or unsubstituted phenyl group, In the general formula (1D-A), one of R ₂₁ to R ₃₀ represents a bonding position to the benz[a]anthracene ring in the general formula (1C-A), and one or more groups of two or more adjacent R ₂₁ to R ₃₀ in the general formula (1D-A) that are not the bonding position are present. bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or Not bonded to each other, R2 1 to R 30 in the general formula (1D-A) that are not bonded to the benz[a]anthracene ring in the general formula (1C-A), that do not form the substituted or unsubstituted monocyclic ring, and that do not form the substituted _{or unsubstituted} condensed ring are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ), -O-(R ₉₀₄ ), -S-(R ₉₀₅ ), -N(R ₉₀₆ )(R ₉₀₇ ), Halogen atoms, Cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, wherein at least one of R ₂₁ to R ₃₀ is a group other than a hydrogen atom, In the compound represented by the general formula (1C-A), R ₉₀₁ , R ₉₀₂ , R ₉₀₃ , R ₉₀₄ , R ₉₀₅ , R ₉₀₆ , R ₉₀₇ , R ₈₀₁ and R ₈₀₂ are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, When there are a plurality of R ₉₀₁ , the plurality of R ₉₀₁ are the same as or different from each other. When there are multiple R ₉₀₂ , the multiple R ₉₀₂ are the same as or different from each other. When there are multiple R ₉₀₃ , the multiple R ₉₀₃ are the same as or different from each other. When there are a plurality of R ₉₀₄ , the plurality of R ₉₀₄ are the same as or different from each other. When there are multiple R ₉₀₅ , the multiple R ₉₀₅ are the same as or different from each other. When there are multiple R ₉₀₆ , the multiple R ₉₀₆ are the same as or different from each other. When there are a plurality of R ₉₀₇ , the plurality of R ₉₀₇ are the same as or different from each other. When there are multiple _R801 , the multiple _R801 are the same as or different from each other. When there are a plurality of R ₈₀₂ , the plurality of R ₈₀₂ are the same as or different from each other. 2. The compound according to claim 1, wherein In the group represented by the general formula (1D-A), at least one of R 21 to R 30 in the general formula (1D-A) that is not _a bonding position to the benz[a]anthracene ring in the general formula (1C-A), does not form the substituted or unsubstituted monocyclic ring, does not form the _substituted or unsubstituted condensed ring, and is not a hydrogen atom is a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms. 3. The compound according to claim 1 or 2, wherein In the group represented by the general formula (1D-A), at least one of R 21 to R 30 in the general formula (1D-A) that is not _a bonding position to the benz[a]anthracene ring in the general formula (1C-A), does not form the substituted or unsubstituted monocyclic ring, does not form _the substituted or unsubstituted condensed ring, and is not a hydrogen atom is a substituted or unsubstituted phenyl group. 4. The compound according to any one of claims 1 to 3, wherein The group represented by the general formula (1D-A) is a group represented by the following general formula (1D-A1), general formula (1D-A2) or general formula (1D-A3), In the general formula (1D-A1), One or more of the groups consisting of two or more adjacent ones of R ₂₁ to R ₂₉ bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or Not bonded to each other, R ₂₁ to R ₂₉ which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ), -O-(R ₉₀₄ ), -S-(R ₉₀₅ ), -N(R ₉₀₆ )(R ₉₀₇ ), Halogen atoms, Cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, wherein at least one of R ₂₁ to R ₂₉ is a group other than a hydrogen atom, * represents the bonding position to the benz[a]anthracene ring in the general formula (1C-A), In the general formula (1D-A2), One or more of the groups consisting of two or more adjacent ones of R ₂₁ to R ₂₈ and R ₃₀ bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or Not bonded to each other, R ₂₁ to R ₂₈ and R ₃₀ that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently the same as R ₂₁ to R ₂₉ in the general formula (1D-A1), wherein at least one of R ₂₁ to R ₂₈ and R ₃₀ is a group other than a hydrogen atom, * represents the bonding position to the benz[a]anthracene ring in the general formula (1C-A), In the general formula (1D-A3), One or more of the group consisting of two or more adjacent ones of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or Not bonded to each other, R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ which do not form the substituted or unsubstituted monocyclic ring and the substituted or unsubstituted condensed ring are independently the same as R ₂₁ to R ₂₉ in the general formula (1D-A1). wherein at least one of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ is a group other than a hydrogen atom, * represents the bonding position to the benz[a]anthracene ring in the general formula (1C-A). 5. The compound according to claim 4, wherein In the group represented by the general formula (1D-A1), the general formula (1D-A2) or the general formula (1D-A3), which does not form the substituted or unsubstituted monocyclic ring, does not form the substituted or unsubstituted condensed ring and is not a hydrogen atom, at least one of R ₂₁ to R ₂₉ in the general formula (1D-A1), at least one of R ₂₁ to R ₂₈ and R ₃₀ in the general formula (1D-A2), or at least one of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ in the general formula (1D-A3) is a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms. 6. The compound according to claim 4 or 5, wherein In the group represented by the general formula (1D-A1), the general formula (1D-A2) or the general formula (1D-A3), which does not form the substituted or unsubstituted monocyclic ring, does not form the substituted or unsubstituted condensed ring and is not a hydrogen atom, at least one of R ₂₁ to R ₂₉ in the general formula (1D-A1), at least one of R ₂₁ to R ₂₈ and R ₃₀ in the general formula (1D-A2), or at least one of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ in the general formula (1D-A3) is a substituted or unsubstituted phenyl group. 7. The compound according to any one of claims 4 to 6, wherein The group represented by the general formula (1D-A) is the group represented by the general formula (1D-A1). 8. The compound according to any one of claims 1 to 7, wherein One of R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ is a group represented by the general formula (1D-A). 9. The compound according to claim 8, wherein One of R ₆ , R ₇ , R ₁₁ and R ₁₂ is a group represented by the general formula (1D-A). 10. The compound according to claim 9, wherein R ₁₁ is a group represented by the general formula (1D-A). 11. The compound according to claim 9, wherein R ₁₂ is a group represented by the general formula (1D-A). 12. The compound according to claim 9, wherein R ₁₁ is a group represented by the general formula (1D-A), and R ₁₂ is an unsubstituted phenyl group; Alternatively, R ₁₂ is a group represented by the general formula (1D-A), and R ₁₁ is an unsubstituted phenyl group. 13. The compound according to claim 12, wherein R ₁₁ is a group represented by the general formula (1D-A), and R ₁₂ is an unsubstituted phenyl group. 14. The compound according to claim 12, wherein R ₁₂ is a group represented by the general formula (1D-A), and R ₁₁ is an unsubstituted phenyl group. 15. The compound according to any one of claims 1 to 14, wherein _R12 is a hydrogen atom. 16. The compound according to any one of claims 1 to 15, wherein There are one or more deuterium atoms in the molecule. 17. The compound according to any one of claims 1 to 16, wherein When one of R ₅ , R ₆ , R ₇ and R ₈ is a group represented by the general formula (1D-A), R ₂ and R ₃ are hydrogen atoms. 18. A compound represented by the following general formula (1C-B), In the general formula (1C-B), One of R ₄ to R ₆ , R ₈ and R ₁₀ to R ₁₂ is a group represented by the general formula (1D-B), R ₁ to R ₃ , R ₇ , R ₉ , and R ₄ to R ₆ , R ₈ and R ₁₀ to R ₁₂ other than the group represented by the general formula (1D-B) are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ), -O-(R ₉₀₄ ), -S-(R ₉₀₅ ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R ₈₀₁ , -COOR ₈₀₂ , Halogen atoms, Cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, When R ₁₁ is a group represented by the general formula (1D-B), R ₁₂ is a hydrogen atom or an unsubstituted phenyl group, When R ₁₂ is a group represented by the general formula (1D-B), R ₁₁ is a substituted or unsubstituted phenyl group, In the general formula (1D-B), one of R ₂₁ to R ₃₀ represents a bonding position to the benz[a]anthracene ring in the general formula (1C-B), and one or more groups of two or more adjacent R ₂₁ to R ₃₀ in the general formula (1D-B) that are not the bonding position are present. bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or Not bonded to each other, R 21 to R 30 in the general formula (1D-B) that are not bonded to the benz[a]anthracene ring in the general formula (1C-B), that do not form the substituted or unsubstituted monocyclic ring, and that do not form the _substituted or _{unsubstituted} condensed ring are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ), -O-(R ₉₀₄ ), -S-(R ₉₀₅ ), -N(R ₉₀₆ )(R ₉₀₇ ), Halogen atoms, Cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In the compound represented by the general formula (1C-B), R ₉₀₁ , R ₉₀₂ , R ₉₀₃ , R ₉₀₄ , R ₉₀₅ , R ₉₀₆ , R ₉₀₇ , R ₈₀₁ and R ₈₀₂ are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, When there are a plurality of R ₉₀₁ , the plurality of R ₉₀₁ are the same as or different from each other. When there are multiple R ₉₀₂ , the multiple R ₉₀₂ are the same as or different from each other. When there are multiple R ₉₀₃ , the multiple R ₉₀₃ are the same as or different from each other. When there are a plurality of R ₉₀₄ , the plurality of R ₉₀₄ are the same as or different from each other. When there are multiple R ₉₀₅ , the multiple R ₉₀₅ are the same as or different from each other. When there are multiple R ₉₀₆ , the multiple R ₉₀₆ are the same as or different from each other. When there are a plurality of R ₉₀₇ , the plurality of R ₉₀₇ are the same as or different from each other. When there are multiple _R801 , the multiple _R801 are the same as or different from each other. When there are a plurality of R ₈₀₂ , the plurality of R ₈₀₂ are the same as or different from each other. 19. The compound according to claim 18, wherein In the group represented by the general formula (1D-B), at least one of R 21 to R 30 in the general formula (1D-B) that is not a bonding position to the benz[a]anthracene ring in the general formula (1C-B) and that does not form the substituted or unsubstituted monocyclic ring and does not _form the _substituted or unsubstituted condensed ring is a group other than a hydrogen atom. 20. The compound according to claim 18 or 19, wherein In the group represented by the general formula (1D-B), at least one of R 21 to R 30 in the general formula (1D-B) that is not a bonding position to the benz[a]anthracene ring in the general formula (1C-B) and does not form the substituted or unsubstituted monocyclic ring and _does not form the _substituted or unsubstituted condensed ring is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. 21. The compound according to claim 20, wherein In the group represented by the general formula (1D-B), at least one of R 21 to R 30 in the general formula (1D-B) that is not a bonding position to the benz[a]anthracene ring in the general formula (1C-B) and that does not form the substituted or unsubstituted monocyclic ring and does not _form the _substituted or unsubstituted condensed ring is a substituted or unsubstituted phenyl group. 22. The compound according to any one of claims 18 to 21, wherein The group represented by the general formula (1D-B) is a group represented by the following general formula (1D-B1), general formula (1D-B2) or general formula (1D-B3), In the general formula (1D-B1), One or more of the groups consisting of two or more adjacent ones of R ₂₁ to R ₂₉ bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or Not bonded to each other, R ₂₁ to R ₂₉ which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ), -O-(R ₉₀₄ ), -S-(R ₉₀₅ ), -N(R ₉₀₆ )(R ₉₀₇ ), Halogen atoms, Cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, * represents the bonding position to the benz[a]anthracene ring in the general formula (1C-B), In the general formula (1D-B2), One or more of the groups consisting of two or more adjacent ones of R ₂₁ to R ₂₈ and R ₃₀ bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or Not bonded to each other, R ₂₁ to R ₂₈ and R ₃₀ that do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently the same as R ₂₁ to R ₂₉ in the general formula (1D-B1), * represents the bonding position to the benz[a]anthracene ring in the general formula (1C-B), In the general formula (1D-B3), One or more of the group consisting of two or more adjacent ones of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or Not bonded to each other, _R21 to _R27 , _R29 and _R30 which do not form the substituted or unsubstituted monocyclic ring and the substituted or unsubstituted condensed ring are independently the same as _R21 to _R29 in the general formula (1D-B1). * represents the bonding position to the benz[a]anthracene ring in the general formula (1C-B). 23. The compound according to claim 22, wherein In the groups represented by the general formula (1D-B1), the general formula (1D-B2) or the general formula (1D-B3), at least one of R ₂₁ to R ₂₉ in the general formula (1D-B1) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, at least one of R ₂₁ to R ₂₈ and R ₃₀ in the general formula (1D-B2), or at least one of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ in the general formula (1D-B3) is a group other than a hydrogen atom. 24. The compound according to claim 22 or 23, wherein In the groups represented by the general formula (1D-B1), the general formula (1D-B2) or the general formula (1D-B3), at least one of R ₂₁ to R ₂₉ in the general formula (1D-B1) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, at least one of R ₂₁ to R ₂₈ and R ₃₀ in the general formula (1D-B2), or at least one of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ in the general formula (1D-B3) is a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms. 25. The compound according to claim 24, wherein In the groups represented by the general formula (1D-B1), the general formula (1D-B2) or the general formula (1D-B3), at least one of R ₂₁ to R ₂₉ in the general formula (1D-B1) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, at least one of R ₂₁ to R ₂₈ and R ₃₀ in the general formula (1D-B2), or at least one of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ in the general formula (1D-B3) is a substituted or unsubstituted phenyl group. 26. The compound according to any one of claims 22 to 24, wherein The group represented by the general formula (1D-B) is the group represented by the general formula (1D-B1). 27. The compound according to any one of claims 18 to 26, wherein One of R ₅ , R ₆ , R ₈ , R ₁₁ and R ₁₂ is a group represented by the general formula (1D-B). 28. The compound according to claim 27, wherein One of R ₆ , R ₁₁ and R ₁₂ is a group represented by the general formula (1D-B). 29. The compound according to claim 28, wherein R ₁₁ is a group represented by the general formula (1D-B). 30. The compound according to claim 28, wherein R ₁₂ is a group represented by the general formula (1D-B). 31. The compound according to claim 28, wherein R ₁₁ is a group represented by the general formula (1D-B), and R ₁₂ is an unsubstituted phenyl group; Alternatively, R ₁₂ is a group represented by the general formula (1D-B), and R ₁₁ is an unsubstituted phenyl group. 32. The compound according to claim 31, wherein R ₁₁ is a group represented by the general formula (1D-B), and R ₁₂ is an unsubstituted phenyl group. 33. The compound according to claim 31, wherein R ₁₂ is a group represented by the general formula (1D-B), and R ₁₁ is an unsubstituted phenyl group. 34. The compound according to any one of claims 18 to 33, wherein _R7 and _R12 are hydrogen atoms. 35. The compound according to any one of claims 18 to 34, wherein There are one or more deuterium atoms in the molecule. 36. A compound represented by the following general formula (1C-C), In the general formula (1C-C), One of R ₄ to R ₈ and R ₁₀ to R ₁₂ is a group represented by the general formula (1D-C), R ₁ to R ₃ , R ₉ , and R ₄ to R ₈ and R ₁₀ to R ₁₂ other than the group represented by the general formula (1D-C) are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ), -O-(R ₉₀₄ ), -S-(R ₉₀₅ ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R ₈₀₁ , -COOR ₈₀₂ , Halogen atoms, Cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, When R ₁₁ is a group represented by the general formula (1D-C), R ₁₂ is a hydrogen atom or a substituted or unsubstituted phenyl group, When R ₁₂ is a group represented by the general formula (1D-C), R ₁₁ is a hydrogen atom or a substituted or unsubstituted phenyl group, In the general formula (1D-C), one of R ₂₂ , R ₂₃ , R ₂₅ , R ₂₇ , R ₂₈ and R ₃₀ represents a bonding position to the benzo[a]anthracene ring in the general formula (1C-C), and one or more of the group consisting of R ₂₁ , R ₂₄ , R ₂₆ and R ₂₉ , and two or more adjacent ones of R ₂₂ , R ₂₃ , R ₂₅ , R ₂₇ , R ₂₈ and R ₃₀ in the general formula (1D-C) that are not the bonding position. bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or Not bonded to each other, R 21 to R 30 in the general formula (1D-C) that are not bonded to the benz[a]anthracene ring in the general formula (1C-C), that do not form the substituted or unsubstituted monocyclic ring, and that do not form the _substituted or _{unsubstituted} condensed ring are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ), -O-(R ₉₀₄ ), -S-(R ₉₀₅ ), -N(R ₉₀₆ )(R ₉₀₇ ), Halogen atoms, Cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In the compound represented by the general formula (1C-C), R ₉₀₁ , R ₉₀₂ , R ₉₀₃ , R ₉₀₄ , R ₉₀₅ , R ₉₀₆ , R ₉₀₇ , R ₈₀₁ and R ₈₀₂ are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, When there are a plurality of R ₉₀₁ , the plurality of R ₉₀₁ are the same as or different from each other. When there are multiple R ₉₀₂ , the multiple R ₉₀₂ are the same as or different from each other. When there are multiple R ₉₀₃ , the multiple R ₉₀₃ are the same as or different from each other. When there are a plurality of R ₉₀₄ , the plurality of R ₉₀₄ are the same as or different from each other. When there are multiple R ₉₀₅ , the multiple R ₉₀₅ are the same as or different from each other. When there are multiple R ₉₀₆ , the multiple R ₉₀₆ are the same as or different from each other. When there are a plurality of R ₉₀₇ , the plurality of R ₉₀₇ are the same as or different from each other. When there are multiple _R801 , the multiple _R801 are the same as or different from each other. When there are a plurality of R ₈₀₂ , the plurality of R ₈₀₂ are the same as or different from each other. 37. The compound according to claim 36, wherein In the group represented by the general formula (1D-C), at least one of R 21 to R 30 in the general formula (1D-C) that is not a bonding position to the benz[a]anthracene ring in the general formula (1C-C) and that does not form the substituted or unsubstituted monocyclic ring and does _{not form} the substituted or unsubstituted condensed ring is a group other than a hydrogen atom. 38. The compound according to claim 36 or 37, wherein In the group represented by the general formula (1D-C), at least one of R 21 to R 30 in the general formula (1D-C) that is not a bonding position to the benz[a]anthracene ring in the general formula (1C-C) and does not form the substituted or unsubstituted monocyclic ring and _does not form the _substituted or unsubstituted condensed ring is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. 39. The compound according to claim 38, wherein In the group represented by the general formula (1D-C), at least one of R 21 to R 30 in the general formula (1D-C) that is not a bonding position to the benz[a]anthracene ring in the general formula (1C-C) and does not form the substituted or unsubstituted monocyclic ring and the _substituted or _{unsubstituted} condensed ring is the substituted or unsubstituted phenyl group. 40. The compound according to any one of claims 36 to 39, wherein The group represented by the general formula (1D-C) is a group represented by the following general formula (1D-C1) or general formula (1D-C3), In the general formula (1D-C1), One or more of the groups consisting of two or more adjacent ones of R ₂₁ to R ₂₉ bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or Not bonded to each other, R ₂₁ to R ₂₉ which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ), -O-(R ₉₀₄ ), -S-(R ₉₀₅ ), -N(R ₉₀₆ )(R ₉₀₇ ), Halogen atoms, Cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, * represents the bonding position to the benz[a]anthracene ring in the general formula (1C-C), In the general formula (1D-C3), One or more of the group consisting of two or more adjacent ones of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or Not bonded to each other, R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ which do not form the substituted or unsubstituted monocyclic ring and the substituted or unsubstituted condensed ring are independently the same as R ₂₁ to R ₂₉ in the general formula (1D-C1). * represents the bonding position to the benz[a]anthracene ring in the general formula (1C-C). 41. The compound according to claim 40, wherein In the group represented by the general formula (1D-C1) or the general formula (1D-C3), at least one of R ₂₁ to R ₂₉ in the general formula (1D-C1) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, or at least one of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ in the general formula (1D-C3) is a group other than a hydrogen atom. 42. The compound according to claim 40 or 41, wherein In the group represented by the general formula (1D-C1) or the general formula (1D-C3), at least one of R ₂₁ to R ₂₉ in the general formula (1D-C1) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, or at least one of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ in the general formula (1D-C3) is a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms. 43. The compound according to claim 42, wherein In the group represented by the general formula (1D-C1) or the general formula (1D-C3), at least one of R ₂₁ to R ₂₉ in the general formula (1D-C1) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, or at least one of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ in the general formula (1D-C3) is a substituted or unsubstituted phenyl group. 44. The compound according to any one of claims 40 to 43, wherein The group represented by the general formula (1D-C) is the group represented by the general formula (1D-C1). 45. The compound according to any one of claims 36 to 44, wherein One of R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ is a group represented by the general formula (1D-C). 46. The compound according to claim 45, wherein One of R ₆ , R ₇ , R ₁₁ and R ₁₂ is a group represented by the general formula (1D-C). 47. The compound according to claim 46, wherein R ₁₁ is a group represented by the general formula (1D-C). 48. The compound according to claim 46, wherein R ₁₂ is a group represented by the general formula (1D-C). 49. The compound according to claim 46, wherein R ₁₁ is a group represented by the general formula (1D-C), and R ₁₂ is an unsubstituted phenyl group; Alternatively, R ₁₂ is a group represented by the general formula (1D-C), and R ₁₁ is an unsubstituted phenyl group. 50. The compound according to claim 49, wherein R ₁₁ is a group represented by the general formula (1D-C), and R ₁₂ is an unsubstituted phenyl group. 51. The compound according to claim 49, wherein R ₁₂ is a group represented by the general formula (1D-C), and R ₁₁ is an unsubstituted phenyl group. 52. The compound according to any one of claims 36 to 51, wherein _R12 is a hydrogen atom. 53. The compound according to any one of claims 36 to 52, wherein There are one or more deuterium atoms in the molecule. 54. The compound according to any one of claims 1 to 53, wherein All groups described as "substituted or unsubstituted" are "unsubstituted" groups. The ring described as "substituted or unsubstituted" is an "unsubstituted" ring. 55. An organic electroluminescent device comprising the compound according to any one of claims 1 to 54. 56. The organic electroluminescent element according to claim 55, which has anode, cathode, and an organic layer disposed between the anode and the cathode, At least one of the organic layers contains the compound. 57. The organic electroluminescent element according to claim 56, wherein The organic layer has a light-emitting region, The light-emitting region comprises at least one light-emitting layer, The light-emitting layer contains the compound. 58. The organic electroluminescent element according to claim 57, wherein The light-emitting region includes a first light-emitting layer and a second light-emitting layer, The first light-emitting layer contains the compound as a first compound, and the second light-emitting layer contains a second compound. 59. The organic electroluminescent element according to claim 58, wherein The triplet energy T ₁ (H1) of the first compound and the triplet energy T ₁ (H2) of the second compound satisfy the relationship of the following mathematical formula (Mathematical formula 1): T ₁ (H1)>T ₁ (H2)...(Mathematical formula 1). 60. The organic electroluminescent element according to claim 58 or 59, wherein: The first light-emitting layer is directly in contact with the second light-emitting layer. 61. The organic electroluminescent element according to any one of claims 58 to 60, wherein The first light-emitting layer is disposed between the anode and the second light-emitting layer. 62. The organic electroluminescent element according to any one of claims 58 to 61, wherein The first light-emitting layer contains a first light-emitting compound, The second light-emitting layer contains a second light-emitting compound, The first light-emitting compound and the second light-emitting compound are each independently a compound that emits light with a maximum peak wavelength of 500 nm or less. 63. The organic electroluminescent element according to any one of claims 57 to 62, wherein A hole transport layer is provided between the anode and the light emitting region. 64. The organic electroluminescent element according to any one of claims 57 to 63, wherein An electron transport layer is provided between the cathode and the light emitting region. 65. An organic electroluminescent element having anode, cathode, and an organic layer disposed between the anode and the cathode, The organic layer has a light-emitting region, The light-emitting region includes a first light-emitting layer and a second light-emitting layer, The first light-emitting layer contains a first compound represented by the following general formula (1C): The second light-emitting layer contains a second compound, In the general formula (1C), One of R ₄ to R ₈ and R ₁₀ to R ₁₂ is a group represented by the general formula (1D), R ₁ to R ₃ , R ₉ , and R ₄ to R ₈ and R ₁₀ to R ₁₂ other than the group represented by the general formula (1D) are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ), -O-(R ₉₀₄ ), -S-(R ₉₀₅ ), a substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms, -C(=O)R ₈₀₁ , -COOR ₈₀₂ , Halogen atoms, Cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, When R ₁₁ is a group represented by the general formula (1D), R ₁₂ is a hydrogen atom or a substituted or unsubstituted phenyl group, When R ₁₂ is a group represented by the general formula (1D), R ₁₁ is a hydrogen atom or a substituted or unsubstituted phenyl group, In the general formula (1D), one of _R21 to _R30 represents a bonding position to the benz[a]anthracene ring in the general formula (1C), and one or more groups of two or more adjacent ones of _R21 to _R30 in the general formula (1D) that are not the bonding position are present. bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or Not bonded to each other, R ₂₁ to R 30 in the general formula (1D) that are not bonded to the benz[a]anthracene ring in the general formula (1C), that do not form the substituted or unsubstituted monocyclic ring, and that do not form the substituted or _{unsubstituted} condensed ring are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ), -O-(R ₉₀₄ ), -S-(R ₉₀₅ ), -N(R ₉₀₆ )(R ₉₀₇ ), Halogen atoms, Cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, In the compound represented by the general formula (1C), R ₉₀₁ , R ₉₀₂ , R ₉₀₃ , R ₉₀₄ , R ₉₀₅ , R ₉₀₆ , R ₉₀₇ , R ₈₀₁ and R ₈₀₂ are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, When there are a plurality of R ₉₀₁ , the plurality of R ₉₀₁ are the same as or different from each other. When there are multiple R ₉₀₂ , the multiple R ₉₀₂ are the same as or different from each other. When there are multiple R ₉₀₃ , the multiple R ₉₀₃ are the same as or different from each other. When there are a plurality of R ₉₀₄ , the plurality of R ₉₀₄ are the same as or different from each other. When there are multiple R ₉₀₅ , the multiple R ₉₀₅ are the same as or different from each other. When there are multiple R ₉₀₆ , the multiple R ₉₀₆ are the same as or different from each other. When there are a plurality of R ₉₀₇ , the plurality of R ₉₀₇ are the same as or different from each other. When there are multiple _R801 , the multiple _R801 are the same as or different from each other. When there are a plurality of R ₈₀₂ , the plurality of R ₈₀₂ are the same as or different from each other. 66. The organic electroluminescent element according to claim 65, wherein In the group represented by the general formula (1D), at least one of R 21 to R 30 in the general formula (1D) that is not a bonding position to the benz[ _a ]anthracene ring in the general formula (1C) and does not form the substituted or unsubstituted monocyclic ring and the substituted or _{unsubstituted} condensed ring is a group other than a hydrogen atom. 67. The organic electroluminescent element according to claim 65 or 66, wherein In the group represented by the general formula (1D), at least one of R 21 to R 30 in the general formula (1D) that is not a bonding position to the benz[ _a ]anthracene ring in the general formula (1C) and does not form the substituted or unsubstituted monocyclic ring and the substituted or unsubstituted condensed ring is a substituted or unsubstituted aryl group _having 6 to 50 ring carbon atoms. 68. The organic electroluminescent element according to claim 67, wherein In the group represented by the general formula (1D), at least one of R 21 to R 30 in the general formula (1D) that is not a bonding position to the benz[ _a ]anthracene ring in the general formula (1C) and does not form the substituted or unsubstituted monocyclic ring and the substituted or _{unsubstituted} condensed ring is a substituted or unsubstituted phenyl group. 69. The organic electroluminescent element according to any one of claims 65 to 68, wherein The group represented by the general formula (1D) is a group represented by the following general formula (1D-1), general formula (1D-2) or general formula (1D-3), In the general formula (1D-1), One or more of the groups consisting of two or more adjacent ones of R ₂₁ to R ₂₉ bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or Not bonded to each other, R ₂₁ to R ₂₉ which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently Hydrogen atoms, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ), -O-(R ₉₀₄ ), -S-(R ₉₀₅ ), -N(R ₉₀₆ )(R ₉₀₇ ), Halogen atoms, Cyano, Nitro, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, * represents the bonding position to the benz[a]anthracene ring in the general formula (1C), In the general formula (1D-2), One or more of the groups consisting of two or more adjacent ones of R ₂₁ to R ₂₈ and R ₃₀ bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or Not bonded to each other, R ₂₁ to R ₂₈ and R ₃₀ which do not form the substituted or unsubstituted monocyclic ring and the substituted or unsubstituted condensed ring are independently the same as R ₂₁ to R ₂₉ in the general formula (1D-1), * represents the bonding position to the benz[a]anthracene ring in the general formula (1C), In the general formula (1D-3), One or more of the group consisting of two or more adjacent ones of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ bonded to each other to form a substituted or unsubstituted monocyclic ring, bonded to each other to form a substituted or unsubstituted condensed ring, or Not bonded to each other, R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ which do not form the substituted or unsubstituted monocyclic ring and the substituted or unsubstituted condensed ring are independently the same as R ₂₁ to R ₂₉ in the general formula (1D-1). * represents the bonding position to the benz[a]anthracene ring in the general formula (1C). 70. The organic electroluminescent element according to claim 69, wherein: In the groups represented by the general formula (1D-1), the general formula (1D-2) or the general formula (1D-3), at least one of R ₂₁ to R ₂₉ in the general formula (1D-1) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, at least one of R ₂₁ to R ₂₈ and R ₃₀ in the general formula (1D-2), or at least one of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ in the general formula (1D-3) is a group other than a hydrogen atom. 71. The organic electroluminescent element according to claim 69 or 70, wherein In the groups represented by the general formula (1D-1), the general formula (1D-2) or the general formula (1D-3), at least one of R ₂₁ to R ₂₉ in the general formula (1D-1) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, at least one of R ₂₁ to R ₂₈ and R ₃₀ in the general formula (1D-2), or at least one of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ in the general formula (1D-3) is a substituted or unsubstituted aromatic group having 6 to 50 ring carbon atoms. 72. The organic electroluminescent element according to claim 71, wherein In the groups represented by the general formula (1D-1), the general formula (1D-2) or the general formula (1D-3), at least one of R ₂₁ to R ₂₉ in the general formula (1D-1) that does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring, at least one of R ₂₁ to R ₂₈ and R ₃₀ in the general formula (1D-2), or at least one of R ₂₁ to R ₂₇ , R ₂₉ and R ₃₀ in the general formula (1D-3) is a substituted or unsubstituted phenyl group. 73. The organic electroluminescent element according to any one of claims 69 to 72, wherein The group represented by the general formula (1D) is the group represented by the general formula (1D-1). 74. The organic electroluminescent element according to any one of claims 65 to 73, wherein One of R ₅ , R ₆ , R ₇ , R ₈ , R ₁₁ and R ₁₂ is a group represented by the general formula (1D). 75. The organic electroluminescent element according to claim 74, wherein: One of R ₆ , R ₇ , R ₁₁ and R ₁₂ is a group represented by the general formula (1D). 76. The organic electroluminescent element according to claim 75, wherein: R ₁₁ is a group represented by the general formula (1D). 77. The organic electroluminescent element according to claim 75, wherein: R ₁₂ is a group represented by the general formula (1D). 78. The organic electroluminescent element according to claim 75, wherein: R ₁₁ is a group represented by the general formula (1D), and R ₁₂ is an unsubstituted phenyl group; Alternatively, R ₁₂ is a group represented by the general formula (1D), and R ₁₁ is an unsubstituted phenyl group. 79. The organic electroluminescent element according to claim 78, wherein R ₁₁ is a group represented by the general formula (1D), and R ₁₂ is an unsubstituted phenyl group. 80. The organic electroluminescent element according to claim 78, wherein R ₁₂ is a group represented by the general formula (1D), and R ₁₁ is an unsubstituted phenyl group. 81. The organic electroluminescent element according to any one of claims 65 to 81, wherein _R12 is a hydrogen atom. 82. The organic electroluminescent element according to any one of claims 65 to 81, wherein There are one or more deuterium atoms in the molecule. 83. The organic electroluminescent element according to any one of claims 65 to 82, wherein The triplet energy T ₁ (H1) of the first compound and the triplet energy T ₁ (H2) of the second compound satisfy the relationship of the following mathematical formula (Mathematical formula 1): T ₁ (H1)>T ₁ (H2)...(Mathematical formula 1). 84. The organic electroluminescent element according to any one of claims 65 to 83, wherein The first light-emitting layer is directly in contact with the second light-emitting layer. 85. The organic electroluminescent element according to any one of claims 65 to 84, wherein The first light-emitting layer is disposed between the anode and the second light-emitting layer. 86. The organic electroluminescent element according to any one of claims 65 to 85, wherein The first light-emitting layer contains a first light-emitting compound, The second light-emitting layer contains a second light-emitting compound, The first light-emitting compound and the second light-emitting compound are each independently a compound that emits light with a maximum peak wavelength of 500 nm or less. 87. The organic electroluminescent element according to any one of claims 65 to 86, wherein A hole transport layer is provided between the anode and the light emitting region. 88. The organic electroluminescent element according to any one of claims 65 to 87, wherein An electron transport layer is provided between the cathode and the light emitting region. 89. An electronic device comprising the organic electroluminescent element according to any one of claims 55 to 88.