CN119053611A

CN119053611A - Compound, material for organic electroluminescent element, and electronic device

Info

Publication number: CN119053611A
Application number: CN202380034908.1A
Authority: CN
Inventors: 皮特·穆勒; 西前祐一; 梅拉·伊尔汗; 安德烈·比特林
Original assignee: Idemitsu Kosan Co Ltd
Current assignee: Idemitsu Kosan Co Ltd
Priority date: 2022-04-28
Filing date: 2023-04-27
Publication date: 2024-11-29
Also published as: WO2023210737A1; KR20250006077A

Abstract

A compound represented by the general formula (1).In the above general formula (1), the ring A1, the ring B1, and the ring C1 are each independently a substituted or unsubstituted ring, X is an oxygen atom, a sulfur atom, a substituent, or the like, a broken line of U1 is bonded to the ring B1 to form a ring, or is bonded to the ring C1 to form a ring, U1 is an oxygen atom, a sulfur atom, N (R ₁₁₁), or B (R ₁₁₂), V1 is N (R ₁₁₃)、B(R₁₁₄), or C (=o), U1 and V1 are different from each other, and R ₁₁₁、R₁₁₂、R₁₁₃ and R ₁₁₄ are each independently a hydrogen atom, a substituent, or the like.

Description

Compound, material for organic electroluminescent element, and electronic device

Technical Field

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

Background

When a voltage is applied to an organic electroluminescent element (hereinafter, sometimes referred to as an "organic EL element"), holes are injected from the anode to the light-emitting layer, and electrons are injected from the cathode to 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 rule of electron spin, singlet excitons are generated at a proportion of 25%, and triplet excitons are generated at a proportion of 75%.

Although organic EL elements of a fluorescence type using luminescence derived from singlet excitons have been applied to full-color displays of mobile phones, televisions, and the like, it is said that internal quantum efficiency of 25% is a limit thereof. Accordingly, studies are being conducted to improve the performance of the organic EL element.

For example, patent documents 1 to 4 disclose cyclic boron compounds as compounds usable for organic electroluminescent devices.

Prior art literature

Patent literature

Patent document 1 International publication No. 2015/102118

Patent document 2 Korean patent application No. 10-2094830

Patent document 3 International publication No. 2020/2173229

Patent document 4 Chinese patent application publication No. 111471064 specification

Disclosure of Invention

Problems to be solved by the invention

In order to improve the performance of electronic devices such as displays, further improvement in the performance of organic EL elements is desired. Examples of the performance of the organic EL element include luminance, emission wavelength, half-width, chromaticity, emission efficiency, driving voltage, and lifetime. For example, a blue light-emitting material is required to be a compound that exhibits an emission peak wavelength in a desired wavelength band in a fluorescence spectrum waveform.

An object of the present invention is to provide a compound that improves element efficiency in the case of being used as a blue light-emitting material among light-emitting materials for organic EL elements. The present invention also provides a material for an organic electroluminescent element, and an electronic device having the organic electroluminescent element, each of which contains a compound that improves element efficiency when used as a blue light-emitting material among light-emitting materials for an organic EL element.

Means for solving the problems

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

[ Chemical formula 1]

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

Ring A1, ring B1 and ring C1 are each independently

Substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or

A substituted or unsubstituted aromatic heterocycle having 6 to 50 ring members,

In the case where the ring A1 has 2 or more substituents, 1 or more groups among groups formed by adjacent 2 or more substituents

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

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

Is not bonded with each other and is not bonded with each other,

In the case where the ring B1 has 2 or more substituents, 1 or more groups among groups formed by adjacent 2 or more substituents

Is not bonded with each other and is not bonded with each other,

In the case where the ring C1 has 2 or more substituents, 1 or more groups among groups formed by adjacent 2 or more substituents

Is not bonded with each other and is not bonded with each other,

The substituent when ring A1 has a substituent, the substituent when ring B1 has a substituent, and the substituent when ring C1 has a substituent are each independently

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

Substituted or unsubstituted cycloalkyl having 3 to 50 ring-forming carbon atoms,

A group represented by-N (R ₁₃₁)(R₁₃₂),

A group represented by Si (R ₁₃₃)(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C (=O) R ₁₃₈ a group,

A group represented by COOR ₁₃₉,

Halogen atom,

Cyano group,

Nitro group,

-A group represented by P (=O) (R ₁₄₀)(R₁₄₁),

A group represented by Ge (R ₁₄₂)(R₁₄₃)(R₁₄₄),

A group represented by (R ₁₄₅)(R₁₄₆),

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

X is

An oxygen atom,

A sulfur atom,

N(R₁₀₁)、

Si (R ₁₀₂)(R₁₀₃), or

C(R₁₀₄)(R₁₀₅),

R ₁₀₁ is

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by Si (R ₁₃₃)(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C (=O) R ₁₃₈ a group,

A group represented by COOR ₁₃₉,

Halogen atom,

Cyano group,

Nitro group,

-A group represented by P (=O) (R ₁₄₀)(R₁₄₁),

A group represented by Ge (R ₁₄₂)(R₁₄₃)(R₁₄₄),

A group represented by (R ₁₄₅₎(R₁₄₆),

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members, or

A group represented by the following general formula (3),

Dashed line of U1

Is bonded to ring B1 to form a substituted or unsubstituted monocyclic ring,

Is bonded to the ring B1 to form a substituted or unsubstituted condensed ring,

To form a substituted or unsubstituted monocyclic ring by bonding to ring C1, or

Is bonded to the ring C1 to form a substituted or unsubstituted condensed ring,

U1 is

An oxygen atom,

A sulfur atom,

N (R ₁₁₁), or

B(R₁₁₂),

V1 is

N(R₁₁₃)、

B (R ₁₁₄), or

C(=O),

U1 and V1 are different from each other,

R ₁₀₂～R₁₀₅、R₁₁₁～R₁₁₄ and R ₁₃₁～R₁₄₆ are each independently of the other

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

Where there are plural R ₁₃₁, plural R ₁₃₁ are the same or different from each other,

Where there are plural R ₁₃₂, plural R ₁₃₂ are the same or different from each other,

Where there are plural R ₁₃₃, plural R ₁₃₃ are the same or different from each other,

Where there are plural R ₁₃₄, plural R ₁₃₄ are the same or different from each other,

Where there are plural R ₁₃₅, plural R ₁₃₅ are the same or different from each other,

Where there are plural R ₁₃₆, plural R ₁₃₆ are the same or different from each other,

Where there are plural R ₁₃₇, plural R ₁₃₇ are the same or different from each other,

Where there are plural R ₁₃₈, plural R ₁₃₈ are the same or different from each other,

Where there are plural R ₁₃₉, plural R ₁₃₉ are the same or different from each other,

Where there are plural R ₁₄₀, plural R ₁₄₀ are the same or different from each other,

Where there are plural R ₁₄₁, plural R ₁₄₁ are the same or different from each other,

Where there are plural R ₁₄₂, plural R ₁₄₂ are the same or different from each other,

Where there are plural R ₁₄₃, plural R ₁₄₃ are the same or different from each other,

Where there are plural R ₁₄₄, plural R ₁₄₄ are the same or different from each other,

Where there are plural R ₁₄₅, plural R ₁₄₅ are the same or different from each other,

In the case where there are plural R ₁₄₆, plural R ₁₄₆ are the same or different from each other. )

[ Chemical formula 2]

(In the above-mentioned general formula (3),

Dashed line of U2

Is bonded to ring A1 to form a substituted or unsubstituted monocyclic ring,

Is bonded to the ring A1 to form a substituted or unsubstituted condensed ring,

To form a substituted or unsubstituted monocyclic ring by bonding to ring B1, or

Is bonded to the ring B1 to form a substituted or unsubstituted condensed ring,

U2 is

An oxygen atom,

A sulfur atom,

N (R ₁₂₁), or

B(R₁₂₂),

V2 is

N(R₁₂₃)、

B (R ₁₂₄), or

C(=O),

U2 and V2 are different from each other,

R ₁₂₁～R₁₂₄ are each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

U1 in the above general formula (1) and U2 in the above general formula (3) are the same or different from each other,

V1 in the above general formula (1) and V2 in the above general formula (3) are the same or different from each other,

* V represents a bonding position to X in the general formula (1). )

According to an aspect of the present invention, there is provided a material for an organic electroluminescent element, which comprises the compound according to an aspect of the present invention described above.

According to an aspect of the present invention, there is provided an organic electroluminescent element having a cathode, an anode, and an organic layer contained between the cathode and the anode, at least 1 layer of the organic layer containing the compound according to the aspect of the present invention as described above as a first compound.

According to an aspect of the present invention, there is provided an electronic device in which the organic electroluminescent element according to the aspect of the present invention described above is mounted.

According to an aspect of the present invention, a compound that improves element efficiency in the case of being used as a blue light-emitting material among light-emitting materials for an organic EL element can be provided. The present invention can also provide a material for an organic electroluminescent element, and an electronic device equipped with the organic electroluminescent element, each of which contains a compound that improves element efficiency when used as a blue light-emitting material among light-emitting materials for an organic EL element.

Drawings

Fig. 1 is a schematic view showing an example of an organic electroluminescent device according to a third embodiment of the present invention.

Fig. 2 is a schematic diagram showing an example of an organic electroluminescent device according to a fourth embodiment of the present invention.

Fig. 3 is a schematic view showing another example of the organic electroluminescent device according to the fourth embodiment of the present invention.

Detailed Description

[ Definition ]

In the present specification, the hydrogen atom means to contain isotopes having different neutron numbers, namely protium (protium), deuterium (deuterium) and tritium (tritium).

In the present specification, in the chemical structural formula, the symbol such as "R" and the bondable position of "D" indicating deuterium atom are not explicitly shown, and are set to be bonded with hydrogen atom, i.e., protium atom, deuterium atom or tritium atom.

In the present specification, the number of ring-forming carbon refers to the number of carbon atoms among atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a ring (for example, a monocyclic compound, a condensed cyclic compound, a bridged cyclic compound, a carbocyclic compound, and a heterocyclic compound). When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of ring-forming carbons. The "number of ring-forming carbons" described below is set similarly unless otherwise indicated. For example, the number of ring-forming carbons of the benzene ring is 6, the number of ring-forming carbons of the naphthalene ring is 10, the number of ring-forming carbons of the pyridine ring is 5, and the number of ring-forming carbons of the furan ring is 4. In addition, for example, the ring-forming carbon number of 9, 9-diphenylfluorenyl is 13,9,9' -spirobifluorenyl and the ring-forming carbon number is 25.

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

In the present specification, the number of ring-forming atoms refers to the number of atoms constituting the ring itself of a compound (for example, a monocyclic compound, a condensed compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) having a structure in which atoms are bonded in a ring (for example, a single ring, a condensed ring, and a bridged ring). Atoms that do not constitute a ring (e.g., hydrogen atoms that terminate bonds to atoms that constitute a ring), and atoms that are contained in a substituent when the ring is substituted with a substituent are not included in the number of ring-forming atoms. The "number of ring-forming atoms" described below is set similarly unless otherwise indicated. For example, the number of ring-forming atoms of the pyridine ring is 6, the number of ring-forming atoms of the quinazoline ring is 10, and the number of ring-forming atoms of the furan ring is 5. For example, the number of hydrogen atoms bonded to the pyridine ring or atoms constituting the substituent is not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms of the pyridine ring to which the hydrogen atom or the substituent is bonded is 6. In addition, for example, a hydrogen atom bonded to a carbon atom of a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms of the quinazoline ring. Accordingly, the number of ring-forming atoms of the quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

In the present specification, "carbon number XX to YY" in the expression of "a substituted or unsubstituted ZZ group having carbon number XX to YY" means the carbon number when the ZZ group is unsubstituted, and the carbon number of the substituent when the substituent is substituted is not included. Here, "YY" is larger than "XX", where "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

In the present specification, "atomic numbers XX to YY" in the expression of "a ZZ group of atomic numbers XX to YY that are substituted or unsubstituted" means the number of atoms when the ZZ group is unsubstituted, and the number of atoms of substituents when substitution occurs is not included. Here, "YY" is larger than "XX", where "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

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

In the present specification, "unsubstituted" when expressed as "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group is not substituted with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, deuterium atom or tritium atom.

In the present specification, "substitution" when referring to "substituted or unsubstituted ZZ group" means that 1 or more hydrogen atoms in the ZZ group are replaced with substituents. The term "substitution" when referring to "BB group substituted with AA group" means that 1 or more hydrogen atoms in BB group are replaced with AA group.

"Substituent described in the specification"

Substituents described in the present specification are described below.

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

The number of ring-forming atoms of the "unsubstituted heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, 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, 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, more preferably 2 to 6, unless otherwise described in the present specification.

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

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

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

The number of ring-forming atoms of the "unsubstituted divalent heterocyclic group" described in the present specification is 5 to 50, preferably 5 to 30, 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, more preferably 1 to 6, unless otherwise described in the present specification.

"Substituted or unsubstituted aryl"

Specific examples of the "substituted or unsubstituted aryl group" described in the present specification (specific example group G1) include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B). (herein, unsubstituted aryl means that "substituted or unsubstituted aryl" is "unsubstituted aryl", and substituted aryl means that "substituted or unsubstituted aryl" is "substituted aryl"), and in this specification, only "aryl" is referred to, both "unsubstituted aryl" and "substituted aryl" are included.

"Substituted aryl" refers to a group in which 1 or more hydrogen atoms of an "unsubstituted aryl" are replaced with a substituent. Examples of the "substituted aryl" include a group obtained by replacing 1 or more hydrogen atoms of the "unsubstituted aryl" of the following specific example group G1A with substituents, and a substituted aryl of the following specific example group G1B. The examples of "unsubstituted aryl" and "substituted aryl" listed herein are only examples, and the "substituted aryl" described in the present specification also includes a group in which a hydrogen atom bonded to a carbon atom of an aryl group itself in the "substituted aryl" of the following specific example group G1B is further substituted with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted aryl" of the following specific example group G1B is further substituted with a substituent.

Unsubstituted aryl (specific example group G1A):

Phenyl group,

P-biphenyl group,

M-biphenyl group,

O-biphenyl group,

P-terphenyl-4-yl,

Para-terphenyl-3-yl,

Para-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 group,

2-Naphthyl group,

Anthracenyl group,

Benzoanthryl radical,

Phenanthryl group,

Benzophenanthryl radical,

Phenalkenyl group,

Pyrenyl group,

A base group,

Benzo (E) benzo (EA base group,

Triphenylene group,

Benzotriphenylene radical,

And tetraphenyl group,

Pentacenyl,

Fluorenyl group,

9,9' -Spirobifluorenyl,

Benzofluorenyl group,

Dibenzofluorenyl group,

Fluorescent anthracyl group,

Benzofluoranthenyl group,

Perylene groups

Monovalent aromatic groups derived by removing 1 hydrogen atom from a ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).

[ Chemical formula 3]

[ Chemical formula 4]

Substituted aryl (specific example group G1B):

O-tolyl group,

M-tolyl group,

P-tolyl group,

P-xylyl radical,

M-xylyl radical,

O-xylyl radical,

P-isopropylphenyl group,

M-isopropylphenyl group,

O-isopropylphenyl group,

P-tert-butylphenyl group,

M-tert-butylphenyl group,

O-tert-butylphenyl group,

3,4, 5-Trimethylphenyl group,

9, 9-Dimethylfluorenyl group,

9, 9-Diphenylfluorenyl,

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

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

9, 9-Bis (4-t-butylphenyl) fluorenyl,

Cyanophenyl group,

Triphenylsilylphenyl radical,

Trimethylsilylphenyl group,

Phenyl naphthyl group,

Naphthyl phenyl

A monovalent group derived from a ring structure represented by the general formulae (TEMP-1) to (TEMP-15) wherein 1 or more hydrogen atoms and substituents are substituted.

"Substituted or unsubstituted heterocyclyl"

The "heterocyclic group" described in the present specification is a cyclic group containing at least 1 hetero atom in the ring-forming atom. Specific examples of the hetero atom 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 this 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.

Specific examples of the "substituted or unsubstituted heterocyclic group" described in the present specification (specific example group G2) include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). (herein, the unsubstituted heterocyclic group means a case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the substituted heterocyclic group means a case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group"). In this specification, only the "heterocyclic group" is expressed to include both the "unsubstituted heterocyclic group" and the "substituted heterocyclic group".

"Substituted heterocyclic group" means a group in which 1 or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with a substituent. Specific examples of the "substituted heterocyclic group" include a group in which a hydrogen atom of the "unsubstituted heterocyclic group" of the following specific example group G2A is substituted, and examples of the substituted heterocyclic group of the following specific example group G2B. Examples of the "unsubstituted heterocyclic group" and examples of the "substituted heterocyclic group" mentioned herein are only examples, and the "substituted heterocyclic group" described in the present specification includes a group in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic group" of the specific example group G2B is further substituted with a substituent, and a group in which a hydrogen atom of the substituent in the "substituted heterocyclic group" of the specific example group G2B is further substituted with a substituent.

Specific examples of the group G2A include, for example, the following unsubstituted heterocyclic group containing a nitrogen atom (example group G2A 1), an unsubstituted heterocyclic group containing an oxygen atom (example group G2A 2), an unsubstituted heterocyclic group containing a sulfur atom (example group G2A 3), and a monovalent heterocyclic group derived by removing 1 hydrogen atom from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) (example group G2A 4).

Specific examples of the group G2B include, for example, the following substituted heterocyclic group containing a nitrogen atom (specific example group G2B 1), substituted heterocyclic group containing an oxygen atom (specific example group G2B 2), substituted heterocyclic group containing a sulfur atom (specific example group G2B 3), and a monovalent heterocyclic group derived from a ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) in which 1 or more hydrogen atoms and substituents have been replaced (specific example group G2B 4).

Unsubstituted heterocyclyl containing a nitrogen atom (specific example group G2 A1):

Pyrrole group,

Imidazolyl group,

Pyrazolyl radical,

Triazolyl radical,

Tetrazolyl group,

Oxazolyl group,

Isoxazolyl radical,

Oxadiazolyl group,

Thiazolyl group,

Isothiazolyl group,

Thiadiazolyl group,

A pyridyl group,

Pyridazinyl group,

Pyrimidinyl group,

Pyrazinyl group,

Triazinyl group,

Indolyl group,

Isoindolyl group,

An indolizinyl group,

Quinolizinyl group,

Quinolinyl radical,

Isoquinolinyl radical,

Cinnolinyl radical,

Phthalazinyl radical,

Quinazolinyl group,

Quinoxalinyl group,

Benzimidazolyl group,

Indazolyl group,

Phenanthroline group,

Phenanthridinyl group,

Acridinyl group,

Phenazinyl group,

Carbazolyl group,

Benzocarbazolyl group,

Morpholinyl group,

Phenoxazinyl group,

Phenothiazinyl group,

Azacarbazolyl groups

Diazacarbazolyl.

Unsubstituted heterocyclyl containing an oxygen atom (specific example group G2 A2):

furyl group,

Oxazolyl group,

Isoxazolyl radical,

Oxadiazolyl group,

Xanthyl group,

Benzofuranyl group,

Isobenzofuranyl group,

Dibenzofuranyl group,

Naphthobenzofuranyl group,

Benzoxazolyl group,

Benzisoxazolyl group,

Phenoxazinyl group,

Morpholinyl group,

Dinaphthofuranyl group,

Azadibenzofuranyl radical,

Diazadibenzofuranyl radical,

Azanaphthobenzofuranyl groups

Naphthyridobenzofuranyl.

Unsubstituted heterocyclyl containing a sulfur atom (specific example group G2 A3):

Thienyl group,

Thiazolyl group,

Isothiazolyl group,

Thiadiazolyl group,

Benzothienyl (benzothienyl),

Isobenzothiophene a base (isobenzothienyl),

Dibenzothiophenes a base (dibenzothienyl),

Naphthacene thienyl (naphthobenzothienyl),

Benzothiazolyl group,

Benzisothiazolyl group,

Phenothiazinyl group,

Dinaphthiophene radical (dinaphthothienyl),

Azadibenzo-p thienyl (azadibenzothienyl),

Diazadibenzo-based compounds thienyl (diazadibenzothienyl),

Azanaphthobenzo thienyl (azanaphthobenzothienyl)

Naphthyridine benzofurans and thienyl (diazanaphthobenzothienyl).

Monovalent heterocyclic groups derived by removing 1 hydrogen atom from the ring structure represented by the following general formulae (TEMP-16) to (TEMP-33) (concrete example group G2A 4):

[ chemical formula 5]

[ Chemical formula 6 ]

In the above general formulae (TEMP-16) to (TEMP-33), X _A and Y _A are each independently an oxygen atom, a sulfur atom, NH or CH ₂. Wherein at least 1 of X _A and Y _A is an oxygen atom, a sulfur atom or NH.

In the general formulae (TEMP-16) to (TEMP-33), when at least one of X _A and Y _A is NH or CH ₂, the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing 1 hydrogen atom from the NH or CH ₂.

Substituted heterocyclyl containing a nitrogen atom (specific example group G2B 1):

(9-phenyl) carbazolyl group,

(9-Biphenylyl) carbazolyl group,

(9-Phenyl) phenylcarbazolyl group,

(9-Naphthyl) carbazolyl group,

Diphenylcarbazol-9-yl,

Phenylcarbazol-9-yl,

Methyl benzimidazolyl group,

Ethylbenzimidazolyl group,

Phenyl triazinyl radical,

Biphenyl triazinyl radical,

Diphenyl triazinyl radical,

Phenyl quinazolinyl

Biphenylquinazolinyl.

Substituted heterocyclyl containing an oxygen atom (specific example group G2B 2):

phenyl dibenzofuranyl group,

Methyl dibenzofuranyl group,

Tert-butyldibenzofuranyl group

Monovalent residues of spiro [ 9H-xanthene-9, 9' - [9H ] fluorene ].

Substituted heterocyclyl containing a sulfur atom (specific example group G2B 3):

Phenyl dibenzothienyl,

Methyl dibenzothienyl,

Tert-butyldibenzothienyl

Monovalent residues of spiro [ 9H-thioxanthene-9, 9' - [9H ] fluorene ].

A monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) wherein 1 or more hydrogen atoms and substituents are substituted (concrete example group G2B 4):

The "1 or more hydrogen atoms of a monovalent heterocyclic group" means 1 or more hydrogen atoms selected from the group consisting of hydrogen atoms bonded to ring-forming carbon atoms of the monovalent heterocyclic group, hydrogen atoms bonded to nitrogen atoms when at least one of X _A and Y _A is NH, and hydrogen atoms of a methylene group when one of X _A and Y _A is CH ₂.

"Substituted or unsubstituted alkyl"

Specific examples of the "substituted or unsubstituted alkyl group" described in the present specification (specific example group G3) include the following unsubstituted alkyl group (specific example group G3A) and substituted alkyl group (specific example group G3B). (herein, unsubstituted alkyl means that "substituted or unsubstituted alkyl" is "unsubstituted alkyl", and substituted alkyl means that "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 1 or more hydrogen atoms in the "unsubstituted alkyl" are replaced with a substituent. Specific examples of the "substituted alkyl" include the following "unsubstituted alkyl" (specific example group G3A), a group in which 1 or more hydrogen atoms and substituents have been replaced, and a substituted alkyl (specific example group G3B). In the present specification, an alkyl group in "unsubstituted alkyl group" means a chain-like alkyl group. Thus, "unsubstituted alkyl" includes "unsubstituted alkyl" as a straight chain and "unsubstituted alkyl" as a branched chain. The examples of "unsubstituted alkyl" and "substituted alkyl" mentioned herein are only examples, and the "substituted alkyl" described in the present specification includes a group in which a hydrogen atom of an alkyl group itself in the "substituted alkyl" of the specific example group G3B is further substituted with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkyl" of the specific example group G3B is further substituted with a substituent.

Unsubstituted alkyl (specific example group G3A):

Methyl group,

Ethyl group,

N-propyl group,

Isopropyl group,

N-butyl group,

Isobutyl group,

Sec-butyl

And (3) tert-butyl.

Substituted alkyl (specific example group G3B):

heptafluoropropyl (including isomers),

Pentafluoroethyl group,

2, 2-Trifluoroethyl group and

Trifluoromethyl.

"Substituted or unsubstituted alkenyl"

Specific examples of the "substituted or unsubstituted alkenyl group" described in the present specification (specific example group G4) include the following unsubstituted alkenyl group (specific example group G4A) and substituted alkenyl group (specific example group G4B). (herein, unsubstituted alkenyl means that "substituted or unsubstituted alkenyl" is "unsubstituted alkenyl", and "substituted alkenyl" means that "substituted or unsubstituted alkenyl" is "substituted alkenyl"), and in this specification, only expression of "alkenyl" includes both "unsubstituted alkenyl" and "substituted alkenyl".

"Substituted alkenyl" refers to a group in which 1 or more hydrogen atoms in the "unsubstituted alkenyl" are replaced with a substituent. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl group" (specific example group G4A) having a substituent, and examples of the substituted alkenyl group (specific example group G4B). The examples of "unsubstituted alkenyl" and "substituted alkenyl" listed herein are only examples, and the "substituted alkenyl" described in this specification includes a group in which a hydrogen atom of an alkenyl group itself in the "substituted alkenyl" of the specific example group G4B is further substituted with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkenyl" of the specific example group G4B is further substituted with a substituent.

Unsubstituted alkenyl (specific example group G4A):

Vinyl group,

Allyl group,

1-Butenyl,

2-Butenyl

3-Butenyl.

Substituted alkenyl (specific example group G4B):

1, 3-butadienyl,

1-Methyl vinyl group,

1-Methylallyl,

1, 1-Dimethylallyl group,

2-Methylallyl

1, 2-Dimethylallyl.

"Substituted or unsubstituted alkynyl"

Specific examples of the "substituted or unsubstituted alkynyl group" described in the present specification (specific example group G5) include the following unsubstituted alkynyl group (specific example group G5A) and the like. (herein, unsubstituted alkynyl refers to the case where "substituted or unsubstituted alkynyl" is "unsubstituted alkynyl"), and when only "alkynyl" is described below, both "unsubstituted alkynyl" and "substituted alkynyl" are included.

"Substituted alkynyl" refers to a group in which 1 or more hydrogen atoms in "unsubstituted alkynyl" are replaced with substituents. Specific examples of the "substituted alkynyl" include an "unsubstituted alkynyl" described below (specific examples group G5A) in which 1 or more hydrogen atoms and substituents are replaced.

Unsubstituted alkynyl (concrete example group G5A):

Ethynyl.

"Substituted or unsubstituted cycloalkyl"

Specific examples of the "substituted or unsubstituted cycloalkyl group" described in the present specification (specific example group G6) include an unsubstituted cycloalkyl group (specific example group G6A) and a substituted cycloalkyl group (specific example group G6B) described below. (herein, unsubstituted cycloalkyl means that "substituted or unsubstituted cycloalkyl" is "unsubstituted cycloalkyl", and substituted cycloalkyl means that "substituted or unsubstituted cycloalkyl" is "substituted cycloalkyl"). In this specification, only "cycloalkyl" is expressed, and both "unsubstituted cycloalkyl" and "substituted cycloalkyl" are included.

"Substituted cycloalkyl" refers to a group in which 1 or more hydrogen atoms in the "unsubstituted cycloalkyl" have been replaced with a substituent. Specific examples of the "substituted cycloalkyl group" include an "unsubstituted cycloalkyl group" (specific example group G6A) in which 1 or more hydrogen atoms and substituents are replaced, and a substituted cycloalkyl group (specific example group G6B) described below. The examples of "unsubstituted cycloalkyl" and "substituted cycloalkyl" mentioned herein are only examples, and the term "substituted cycloalkyl" as used herein includes a group in which 1 or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl" of the specific example group G6B are replaced with a substituent, and a group in which the hydrogen atom of the substituent in the "substituted cycloalkyl" of the specific example group G6B is further replaced with a substituent.

Unsubstituted cycloalkyl (specific example group G6A):

Cyclopropyl group,

Cyclobutyl group,

Cyclopentyl group,

Cyclohexyl group,

1-Adamantyl group,

2-Adamantyl group,

1-Norbornyl group

2-Norbornyl.

Substituted cycloalkyl (specific example group G6B):

4-methylcyclohexyl.

Radicals "shown in" -Si (R ₉₀₁)(R₉₀₂)(R₉₀₃) "

Specific examples of the group represented by-Si (R ₉₀₁)(R₉₀₂)(R₉₀₃) described in the present specification (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 the number of the elements to be processed is,

G1 is "substituted or unsubstituted aryl" as described in the concrete example group G1.

G2 is a "substituted or unsubstituted heterocyclic group" as described in the concrete example group G2.

G3 is "substituted or unsubstituted alkyl group" described in the concrete example group G3.

G6 is "substituted or unsubstituted cycloalkyl" as described in the concrete example group G6.

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

-A plurality of G2 of Si (G1) (G2) being the same or different from each other.

-A plurality of G1 s of Si (G1) (G2) being the same or different from each other.

-A plurality of G2 in Si (G2) being the same or different from each other.

-A plurality of G3 in Si (G3) being the same or different from each other.

-A plurality of G6 of Si (G6) being the same or different from each other.

Radical "-O- (R ₉₀₄)" as indicated "

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

-O(G1)、

-O(G2)、

-O (G3) and

-O(G6)。

Here the number of the elements to be processed is,

"Group represented by S- (R ₉₀₅)":

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

-S(G1)、

-S(G2)、

-S (G3) and

-S(G6)。

Here the number of the elements to be processed is,

"Group represented by N (R ₉₀₆)(R₉₀₇)":

Specific examples of the group represented by-N (R ₉₀₆)(R₉₀₇) described in the present specification (group G10) include

-N(G1)(G1)、

-N(G2)(G2)、

-N(G1)(G2)、

-N (G3) (G3) and

-N(G6)(G6)。

Here the number of the elements to be processed is,

-A plurality of G1 in N (G1) being the same or different from each other.

-A plurality of G2 in N (G2) being the same or different from each other.

-A plurality of G3 in N (G3) being the same or different from each other.

-A plurality of G6 in N (G6) being the same or different from each other.

"Halogen atom"

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, an iodine atom, and the like.

"Substituted or unsubstituted fluoroalkyl"

The term "substituted or unsubstituted fluoroalkyl" as used herein refers to a group in which at least 1 hydrogen atom bonded to a carbon atom constituting an alkyl group in the term "substituted or unsubstituted alkyl group" is replaced with a fluorine atom, and includes a group (perfluoro group) in which all hydrogen atoms bonded to a carbon atom constituting an alkyl group in the term "substituted or unsubstituted alkyl group" are replaced with a fluorine atom. The carbon number of the "unsubstituted fluoroalkyl" is 1 to 50, preferably 1 to 30, more preferably 1 to 18, unless otherwise stated in the specification. "substituted fluoroalkyl" refers to a radical obtained by replacing 1 or more hydrogen atoms of "fluoroalkyl" with substituents. The term "substituted fluoroalkyl" as used herein includes a group in which 1 or more hydrogen atoms bonded to a carbon atom of an alkyl chain in the term "substituted fluoroalkyl" are further substituted with a substituent, and a group in which 1 or more hydrogen atoms of a substituent in the term "substituted fluoroalkyl" are further substituted with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include those obtained by replacing 1 or more hydrogen atoms and fluorine atoms in the "alkyl group" (specific example group G3).

"Substituted or unsubstituted haloalkyl"

The term "substituted or unsubstituted haloalkyl" as used herein refers to a group in which at least 1 hydrogen atom bonded to a carbon atom constituting an alkyl group in the term "substituted or unsubstituted alkyl" is replaced with a halogen atom, and includes a group in which all hydrogen atoms bonded to a carbon atom constituting an alkyl group in the term "substituted or unsubstituted alkyl" are replaced with a halogen atom. The carbon number of the "unsubstituted haloalkyl" is 1 to 50, preferably 1 to 30, more preferably 1 to 18, unless otherwise stated in the specification. "substituted haloalkyl" refers to a radical obtained by substituting 1 or more hydrogen atoms of "haloalkyl" with substituents. The term "substituted haloalkyl" as used herein also includes a group in which 1 or more hydrogen atoms bonded to a carbon atom of an alkyl chain in the term "substituted haloalkyl" are further substituted with a substituent, and a group in which 1 or more hydrogen atoms of a substituent in the term "substituted haloalkyl" are further substituted with a substituent. Specific examples of the "unsubstituted haloalkyl group" include those wherein 1 or more hydrogen atoms and halogen atoms in the above-mentioned "alkyl group" (specific example group G3) have been replaced. Haloalkyl is sometimes referred to as haloalkyl.

"Substituted or unsubstituted alkoxy"

Specific examples of the "substituted or unsubstituted alkoxy group" described in the present specification are groups represented by-O (G3), and G3 is a "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, more preferably 1 to 18, unless otherwise stated in the present specification.

"Substituted or unsubstituted alkylthio"

Specific examples of the "substituted or unsubstituted alkylthio group" described in the present specification are groups represented by-S (G3), and G3 is a "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, more preferably 1 to 18, unless otherwise stated in the specification.

"Substituted or unsubstituted aryloxy"

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

"Substituted or unsubstituted arylthio"

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

"Substituted or unsubstituted trialkylsilyl"

Specific examples of the "trialkylsilyl group" described in the present specification are groups 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 in Si (G3) being the same or different from each other. The carbon number of each alkyl group of the "trialkylsilyl" is 1 to 50, preferably 1 to 20, more preferably 1 to 6, unless otherwise stated in the specification.

"Substituted or unsubstituted aralkyl"

Specific examples of the "substituted or unsubstituted aralkyl group" described in the present specification are groups represented by- (G3) to (G1), where G3 is a "substituted or unsubstituted alkyl group" described in the specific example group G3, and G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. Accordingly, the "aralkyl" is a group obtained by replacing a hydrogen atom of the "alkyl" with the "aryl" as a substituent, and is one embodiment of the "substituted alkyl". 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, phenyltert-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, phenanthryl, pyrenyl,Phenyl, triphenylenyl, fluorenyl, 9' -spirobifluorenyl, 9-dimethylfluorenyl, 9-diphenylfluorenyl, and the like.

The substituted or unsubstituted heterocyclic group described in the present specification is preferably pyridyl, pyrimidinyl, triazinyl, quinolinyl, isoquinolinyl, quinazolinyl, benzimidazolyl, phenanthrolinyl, carbazolyl (1-carbazolyl, 2-carbazolyl, 3-carbazolyl, 4-carbazolyl or 9-carbazolyl), benzocarbazolyl, azacarbazolyl, diazacarbazolyl, dibenzofuranyl, naphthobenzofuranyl, azadibenzofuranyl, diazadibenzofuranyl, dibenzothienyl, naphthobenzothienyl, azadibenzothienyl, (9-phenyl) carbazolyl ((9-phenyl) carbazol-1-yl, (9-phenyl) carbazol-2-yl, (9-phenyl) carbazol-3-yl or (9-phenyl) carbazol-4-yl), (9-phenyl) phenylcarbazolyl, diphenylcarbazolyl, phenylcarbazolyl, phenyltriazinyl, dibenzotriazinyl, dibenzofuranyl, etc., unless otherwise specified.

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

[ Chemical formula 7 ]

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

[ Chemical formula 8]

In the general formulas (TEMP-Cz 1) - (TEMP-Cz 9), the bonding position is represented by x.

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

[ Chemical formula 9 ]

In the general formulae (TEMP-34) - (TEMP-41), the bonding position is represented.

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

"Substituted or unsubstituted arylene"

The "substituted or unsubstituted arylene group" described in the present specification is a divalent group derived by removing 1 hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" unless otherwise specified. Specific examples of the "substituted or unsubstituted arylene group" (concrete example group G12) include a divalent group derived by removing 1 hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in concrete example group G1.

"Substituted or unsubstituted divalent heterocyclic radical"

The "substituted or unsubstituted divalent heterocyclic group" described in the present specification is a divalent group derived by removing 1 hydrogen atom on a heterocycle from the "substituted or unsubstituted heterocyclic group" unless otherwise described. Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (concrete example group G13) include a divalent group derived by removing 1 hydrogen atom on a heterocycle from the "substituted or unsubstituted heterocyclic group" described in concrete example group G2.

"Substituted or unsubstituted alkylene"

The "substituted or unsubstituted alkylene group" described in the present specification is a divalent group derived by removing 1 hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" unless otherwise specified. Specific examples of the "substituted or unsubstituted alkylene group" (concrete example group G14) include a divalent group derived by removing 1 hydrogen atom from the alkyl chain from the "substituted or unsubstituted alkyl group" described in concrete example group G3.

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 10 ]

[ Chemical formula 11 ]

In the general formulae (TEMP-42) to (TEMP-52), Q ₁～Q₁₀ is independently a hydrogen atom or a substituent.

In the general formulae (TEMP-42) - (TEMP-52), the bonding position is represented.

[ Chemical formula 12 ]

In the general formulae (TEMP-53) to (TEMP-62), Q ₁～Q₁₀ is independently a hydrogen atom or a substituent.

Formulas Q ₉ and Q ₁₀ may be bonded to each other via a single bond to form a ring.

In the general formulae (TEMP-53) - (TEMP-62), the bonding position is represented.

[ Chemical formula 13 ]

In the general formulae (TEMP-63) to (TEMP-68), Q ₁～Q₈ is independently a hydrogen atom or a substituent.

In the general formulae (TEMP-63) - (TEMP-68), the bonding position is represented.

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 14 ]

[ Chemical formula 15 ]

[ Chemical formula 16 ]

In the general formulae (TEMP-69) to (TEMP-82), Q ₁～Q₉ is independently a hydrogen atom or a substituent.

[ Chemical formula 17 ]

[ Chemical formula 18 ]

[ Chemical formula 19 ]

[ Chemical formula 20 ]

In the general formulae (TEMP-83) to (TEMP-102), Q ₁～Q₈ is independently a hydrogen atom or a substituent.

The above is a description of "substituents described in the present specification".

"Case of bonding to form a Ring"

In this specification, the expression "a case where 1 or more groups of 2 or more adjacent groups are bonded to each other to form a substituted or unsubstituted single ring, or are bonded to each other to form a substituted or unsubstituted condensed ring, or are not bonded to each other" refers to a case where 1 or more groups of 2 or more adjacent groups are bonded to each other to form a substituted or unsubstituted single ring, "a case where 1 or more groups of 2 or more adjacent groups are bonded to each other to form a substituted or unsubstituted condensed ring," and a case where 1 or more groups of 2 or more adjacent groups are not bonded to each other.

Hereinafter, a description will be given of a case where 1 or more groups of 2 or more adjacent groups are bonded to each other to form a substituted or unsubstituted single ring and a case where 1 or more groups of 2 or more adjacent groups are bonded to each other to form a substituted or unsubstituted condensed ring (hereinafter, these cases are sometimes referred to as "a case where bonding forms a ring"). The case of an anthracene compound represented by the following general formula (TEMP-103) having a parent skeleton as an anthracene ring will be described as an example.

[ Chemical formula 21 ]

For example, in the case where 1 or more groups of "adjacent 2 or more groups among R ₉₂₁～R₉₃₀ are bonded to each other to form a ring", the group of 2 adjacent groups as 1 group means a group of R ₉₂₁ and R ₉₂₂, a group of R ₉₂₂ and R ₉₂₃, a group of, A group of R ₉₂₃ and R ₉₂₄, a group of R ₉₂₄ and R ₉₃₀, a group of R ₉₃₀ and R ₉₂₅, a group of R ₉₂₅ and R ₉₂₆, a group of R ₉₂₆ and R ₉₂₇, a group of R ₉₂₇ and R ₉₂₈, A group of R ₉₂₈ and R ₉₂₉, and a group of R ₉₂₉ and R ₉₂₁.

The "1 or more groups" means that 2 or more groups of the adjacent 2 or more groups can form a ring at the same time. For example, when R ₉₂₁ and R ₉₂₂ are bonded to each other to form a ring Q _A and simultaneously R ₉₂₅ and R ₉₂₆ are bonded to each other to form a ring Q _B, the anthracene compound represented by the above general formula (TEMP-103) is represented by the following general formula (TEMP-104).

[ Chemical formula 22 ]

The case where "a group of 2 or more adjacent" forms a ring includes not only the case where a group of 2 or more adjacent "as in the foregoing example is bonded but also the case where a group of 3 or more adjacent" 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 3 groups (R ₉₂₁、R₉₂₂ and R ₉₂₃) adjacent to each other are bonded to each other to form a ring and condensed on an anthracene skeleton, and in this case, an anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), R ₉₂₂ is shared by the ring Q _A and the ring Q _C.

[ Chemical formula 23 ]

In the "single ring" or "condensed ring" formed, the structure of only the formed ring may be a saturated ring or an unsaturated ring. Even in the case where 1 group of "2 adjacent groups" forms a "single ring" or "condensed ring", the "single ring" or "condensed ring" may form a saturated ring or an unsaturated ring. For example, the ring Q _A and the ring Q _B formed in the above general formula (TEMP-104) are each a "single ring" or a "condensed ring". In addition, the ring Q _A and the ring Q _c formed in the above general formula (TEMP-105) are "condensed rings". The rings Q _A and Q _C of the general formula (TEMP-105) are fused to form a fused ring by the ring Q _A and the ring Q _C. If ring Q _A of the above general formula (TMEP-104) is a benzene ring, ring Q _A is a single ring. If the ring Q _A of the above general formula (TMEP-104) is a naphthalene ring, the ring Q _A is a condensed ring.

"Unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocycle. "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.

Specific examples of the aromatic hydrocarbon ring include a structure in which a group specifically exemplified as group G1 is blocked with a hydrogen atom.

Specific examples of the aromatic heterocyclic ring include a structure in which an aromatic heterocyclic group specifically exemplified as group G2 is blocked with a hydrogen atom.

Specific examples of the aliphatic hydrocarbon ring include structures in which a group specifically exemplified as group G6 is blocked with a hydrogen atom.

"Forming a ring" means forming a ring from only multiple atoms of the parent skeleton or from multiple atoms of the parent skeleton with 1 or more additional optional elements. For example, the ring Q _A formed by bonding R ₉₂₁ and R ₉₂₂ shown by the general formula (TEMP-104) refers to a ring formed by the carbon atom of the anthracene skeleton bonded by R ₉₂₁ and the carbon atom of the anthracene skeleton bonded by R ₉₂₂ and 1 or more optional elements. Specifically, in the case where R ₉₂₁ and R ₉₂₂ form a ring Q _A, when a monocyclic unsaturated ring is formed by a carbon atom of an anthracene skeleton to which R ₉₂₁ is bonded, a carbon atom of an anthracene skeleton to which R ₉₂₂ is bonded, and 4 carbon atoms, the ring formed by R ₉₂₁ and R ₉₂₂ is a benzene ring.

Here, the "optional element" is preferably at least 1 element selected from the group consisting of a carbon element, a nitrogen element, an oxygen element, and a sulfur element unless otherwise described in the present specification. In the optional element (for example, in the case of a carbon element or a nitrogen element), the bond which does not form a ring may be blocked by a hydrogen atom or the like, or may be substituted by an "optional substituent" described later. When an optional element other than carbon is included, the ring formed is a heterocyclic ring.

If not otherwise described in the present specification, "1 or more optional elements" constituting a single ring or a condensed ring are preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and still more preferably 3 or more and 5 or less.

In the present specification, unless otherwise stated, the term "monocyclic ring" and the term "condensed ring" are preferably "monocyclic ring".

In the present specification, unless otherwise stated, the "saturated ring" and the "unsaturated ring" are preferably "unsaturated ring".

In the present specification, unless otherwise stated, the "monocyclic ring" is preferably a benzene ring.

In the present specification, unless otherwise stated, the "unsaturated ring" is preferably a benzene ring.

In the case where "1 or more groups of 2 or more adjacent groups" are bonded to each other to form a substituted or unsubstituted single ring "or" are bonded to each other to form a substituted or unsubstituted condensed ring "unless otherwise stated in the present specification, it is preferable that 1 or more groups of 2 or more adjacent groups are bonded to each other to form a substituted or unsubstituted" unsaturated ring "formed of a plurality of atoms of a parent skeleton and 1 or more and 15 or less elements selected from at least one element of the group consisting of carbon element, nitrogen element, oxygen element and sulfur element.

The substituent when the "single ring" or "condensed ring" has a substituent is, for example, an "optional substituent" described later. Specific examples of the substituent when the "single ring" or "condensed ring" has a substituent are the substituents described in the above item of "substituent described in the present specification".

The substituent when the "saturated ring" or "unsaturated ring" has a substituent is, for example, an "optional substituent" described later. Specific examples of the substituent when the "single ring" or "condensed ring" has a substituent are the substituents described in the above item of "substituent described in the present specification".

The above is a description of the case where 1 or more groups of 2 or more adjacent groups are bonded to each other to form a substituted or unsubstituted single ring and the case where 1 or more groups of 2 or more adjacent groups are bonded to each other to form a substituted or unsubstituted condensed ring ("case where bonding is performed to form a ring").

Substituents when expressed as "substituted or unsubstituted

In one embodiment of the present specification, the substituent when expressed as "substituted or unsubstituted" (in the present specification, sometimes referred to as "optional substituent") is, for example, a substituent selected from the group consisting of

Unsubstituted alkyl group having 1 to 50 carbon atoms,

Unsubstituted alkenyl group having 2 to 50 carbon atoms,

Unsubstituted alkynyl with 2-50 carbon atoms,

Unsubstituted cycloalkyl having 3 to 50 ring-forming carbon atoms,

-Si(R₉₀₁)(R₉₀₂)(R₉₀₃)、

-O-(R₉₀₄)、

-S-(R₉₀₅)、

-N(R₉₀₆)(R₉₀₇)、

Halogen atom, cyano group, nitro group,

Unsubstituted aryl groups having 6 to 50 ring carbon atoms and

Unsubstituted heterocyclic group having 5 to 50 ring members

A group in the group consisting of, and the like,

Wherein R ₉₀₁～R₉₀₇ is each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

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

When more than 2R ₉₀₁ exist, more than 2R ₉₀₁ are the same or different from each other,

When more than 2R ₉₀₂ exist, more than 2R ₉₀₂ are the same or different from each other,

When more than 2R ₉₀₃ exist, more than 2R ₉₀₃ are the same or different from each other,

When more than 2R ₉₀₄ exist, more than 2R ₉₀₄ are the same or different from each other,

When more than 2R ₉₀₅ exist, more than 2R ₉₀₅ are the same or different from each other,

When more than 2R ₉₀₆ exist, more than 2R ₉₀₆ are the same or different from each other,

When there are 2 or more R ₉₀₇, 2 or more R ₉₀₇ are the same or different from each other.

In one embodiment, the substituents described above as "substituted or unsubstituted" are selected from the group consisting of

An alkyl group having 1 to 50 carbon atoms,

Aryl with ring-forming carbon number of 6-50

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

An alkyl group having 1 to 18 carbon atoms,

Aryl with ring-forming carbon number of 6-18

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

Specific examples of each of the above-mentioned optional substituents are specific examples of the substituents described in the item of "substituent described in the present specification" above.

Unless otherwise indicated herein, adjacent optional substituents may form a "saturated ring" or an "unsaturated ring", and preferably form 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, and more preferably form a benzene ring.

The optional substituent may further have a substituent unless otherwise stated in the specification. The substituent further included as an optional substituent is the same as the above optional substituent.

In the present specification, the numerical range indicated by "AA to BB" means a range including the numerical value AA described in front of "AA to BB" as a lower limit value and the numerical value BB described in rear of "AA to BB" as an upper limit value.

First embodiment

(Compound)

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

[ Chemical formula 24 ]

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

Ring A1, ring B1 and ring C1 are each independently

Is not bonded with each other and is not bonded with each other,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by-N (R ₁₃₁)(R₁₃₂),

A group represented by Si (R ₁₃₃)(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C (=O) R ₁₃₈ a group,

A group represented by COOR ₁₃₉,

Halogen atom,

Cyano group,

Nitro group,

-A group represented by P (=O) (R ₁₄₀)(R₁₄₁),

A group represented by Ge (R ₁₄₂)(R₁₄₃)(R1₄₄),

A group represented by (R ₁₄₅)(R₁₄₆),

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

X is

An oxygen atom,

A sulfur atom,

N(R₁₀₁)、

Si (R ₁₀₂)(R₁₀₃), or

C(R₁₀₄)(R₁₀₅),

R ₁₀₁ is

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by Si (R ₁₃₃)(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C (=O) R ₁₃₈ a group,

A group represented by COOR ₁₃₉,

Halogen atom,

Cyano group,

Nitro group,

-A group represented by P (=O) (R ₁₄₀₎(R₁₄₁),

A group represented by Ge (R ₁₄₂₎(R₁₄₃)(R₁₄₄),

A group represented by (R ₁₄₅)(R₁₄₆),

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

A group represented by the following general formula (3),

Dashed line of U1

Is bonded to ring B1 to form a substituted or unsubstituted monocyclic ring,

Is bonded to the ring B1 to form a substituted or unsubstituted condensed ring,

Is bonded to the ring C1 to form a substituted or unsubstituted condensed ring,

U1 is

An oxygen atom,

A sulfur atom,

N (R ₁₁₁), or

B(R₁₁₂),

V1 is

N(R₁₁₃)、

B (R ₁₁₄), or

C(=O),

U1 and V1 are different from each other,

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

[ Chemical formula 25 ]

(In the above-mentioned general formula (3),

Dashed line of U2

Is bonded to ring A1 to form a substituted or unsubstituted monocyclic ring,

Is bonded to the ring A1 to form a substituted or unsubstituted condensed ring,

Is bonded to the ring B1 to form a substituted or unsubstituted condensed ring,

U2 is

An oxygen atom,

A sulfur atom,

N (R ₁₂₁), or

B(R₁₂₂),

V2 is

N(R₁₂₃)、

B (R ₁₂₄), or

C(=O),

U2 and V2 are different from each other,

R ₁₂₁～R₁₂₄ are each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

* V represents a bonding position to X in the above general formula (1). )

According to the present embodiment, a compound that improves element efficiency in the case of being used as a blue light-emitting material among light-emitting materials for an organic EL element can be provided.

According to the compound according to one embodiment, a compound having a luminescence peak wavelength in a desired wavelength band in a fluorescence spectrum waveform can be provided. According to the compound according to one embodiment, light having a narrow half-width of a fluorescence emission spectrum is emitted. According to one embodiment related compounds, PLQY exhibits high values.

By using the compound according to one embodiment as a material of an organic EL element, light having a small half-width of a fluorescence emission spectrum can be emitted from the element. As a result, the light emission efficiency of the organic EL element can be improved.

In the present specification, the maximum peak wavelength of fluorescence emission may be referred to as a fluorescence emission maximum peak wavelength or a maximum peak wavelength.

The maximum peak wavelength of fluorescence emission of the compound according to the present embodiment is preferably 445nm or more. The maximum peak wavelength of fluorescence emission of the compound according to the present embodiment is preferably 480nm or less, more preferably 465nm or less. If the maximum peak wavelength of fluorescence emission of the compound of the present embodiment is 445nm or more, appropriate blue emission as a target can be easily obtained in an electronic device such as a display in which the organic EL element containing the compound of the present embodiment is mounted. If the maximum peak wavelength of fluorescence emission of the compound of the present embodiment is 480nm or less, appropriate blue emission as a target can be easily obtained in an electronic device such as a display in which the organic EL element containing the compound of the present embodiment is mounted.

In the present specification, the maximum peak wavelength of fluorescence emission means the maximum peak wavelength of fluorescence spectrum at which the emission intensity of the measured fluorescence spectrum is the maximum, in a toluene solution in which a compound to be measured is dissolved at a concentration of 10 ^-6 mol/liter or more and 10 ^-5 mol/liter or less. As the measurement device, a fluorescence spectrum measurement device (device name: FP-8300, manufactured by Japanese spectroscopy Co., ltd.) was used. The fluorescence spectrum measuring apparatus is not limited to the apparatus illustrated here.

The compound according to the present embodiment preferably has a lower minimum excited singlet energy level (hereinafter, sometimes referred to as S1 level) which is estimated. For example, the S1 level of the compound according to the present embodiment is preferably in the range of 2.6eV to 3.1eV, more preferably in the range of 2.6eV to 3.0 eV. Therefore, according to one embodiment, it is considered that an electronic device such as a display device mounted with an organic EL element containing the compound according to the present embodiment can easily obtain a desired emission of blue light.

The S1 level can be calculated by TD-DFT using B3LYP as the hybridization density functional, 6-31g as the basis function, and Gaussian 16 software program available from Gaussian inc.

The compound according to this embodiment preferably has a high photoluminescence quantum yield (PLQY: photoluminescence quantum yield).

The compound according to the present embodiment preferably has PLQY of 80% or more, and more preferably 85% or more.

The PLQY measurement method includes the following methods.

A compound to be measured was dissolved in toluene to prepare a 5.0X10 ^-6 mol/L solution, and the solution was subjected to freeze-degassing to prepare an argon-saturated solution. The obtained solution was transferred to a quartz cuvette (optical path length 1.0 cm), and a photoluminescence quantum yield (PLQY) was measured using an absolute PL quantum yield measuring device "Hamamatsu Quantaurus-QY C11347" (manufactured by kayaku photonics corporation).

In the compound represented by the above general formula (1), when R ₁₀₁ is a group represented by the above general formula (3), U1 in the above general formula (1) and U2 in the above general formula (3) are preferably the same as each other.

In the compound represented by the above general formula (1), when R ₁₀₁ is a group represented by the above general formula (3), V1 in the above general formula (1) and V2 in the above general formula (3) are preferably the same as each other.

In the compound according to the present embodiment, the compound represented by the above general formula (1) may contain at least one ring structure selected from the ring structures represented by the following general formula (10), the following general formula (20) and the following general formula (30) in a molecule.

Among the compounds according to the present embodiment, the compound represented by the above general formula (1) may be, for example, a compound having a ring structure represented by the following general formula (10), a compound having a ring structure represented by the following general formula (20), or a compound having a ring structure represented by the following general formulae (10) and (30).

[ Chemical formula 26 ]

(In the above-mentioned general formula (10),

V1 has the same meaning as V1 in the above general formula (1),

U1 has the same meaning as U1 in the above general formula (1),

U1 and V1 are different from each other,

More than 1 group of groups consisting of 2 adjacent more than 2 of R ₁、R₂ and R ₃

Is not bonded with each other and is not bonded with each other,

R ₁～R₃ which does not form the above-mentioned substituted or unsubstituted monocyclic ring and which does not form the above-mentioned substituted or unsubstituted condensed ring is each independently

Hydrogen atom

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

A group represented by-N (R ₁₃₁₎(R₁₃₂),

A group represented by Si (R ₁₃₃)(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Halogen atom,

Cyano group,

A group represented by (R ₁₄₅)(R₁₄₆),

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

*11 Represents a bonding position to the ring B1 in the above general formula (1),

*12 Represents a bonding position of B (boron atom) bonded to the ring A1, the ring B1 and the ring C1 in the above general formula (1),

In the above-mentioned general formula (20),

V1 has the same meaning as V1 in the above general formula (1),

U1 has the same meaning as U1 in the above general formula (1),

U1 and V1 are different from each other,

Group consisting of R ₄ and R ₅

Is not bonded with each other and is not bonded with each other,

R4 and R ₅ which do not form the above-mentioned substituted or unsubstituted monocyclic ring and which do not form the above-mentioned substituted or unsubstituted condensed ring are each independently

Hydrogen atom

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

A group represented by-N (R ₁₃₁)(R₁₃₂),

A group represented by Si (R ₁₃₃)(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Halogen atom,

Cyano group,

A group represented by (R ₁₄₅)(R₁₄₆),

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

*21 Represents a bonding position of X bonded to the ring A1 and the ring B1 in the above general formula (1),

*22 Represents a bonding position of B (boron atom) bonded to the ring A1, the ring B1 and the ring C1 in the above general formula (1),

*23 Represents a bonding position to the ring C1 in the above general formula (1),

In the above-mentioned general formula (30),

V2 has the same meaning as V2 when R ₁₀₁ in the above general formula (1) is a group represented by the above general formula (3),

U2 has the same meaning as U2 when R ₁₀₁ in the above general formula (1) is a group represented by the above general formula (3),

U2 and V2 are different from each other,

More than 1 group of groups consisting of 2 adjacent more than 2 of R ₆、R₇ and R ₈

Is not bonded with each other and is not bonded with each other,

R ₆、R₇ and R ₈ which do not form the above-mentioned substituted or unsubstituted monocyclic ring and which do not form the above-mentioned substituted or unsubstituted condensed ring are

Hydrogen atom

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

A group represented by-N (R ₁₃₁₎(R₁₃₂),

A group represented by Si (R ₁₃₃)(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Halogen atom,

Cyano group,

A group represented by (R ₁₄₅₎(R₁₄₆),

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

*31 Represents a bonding position of B (boron atom) bonded to the ring A1, the ring B1 and the ring C1 in the above general formula (1),

*32 Represents a bonding position to the ring B1 in the above general formula (1). )

The ring structure represented by the above general formula (10) is preferably a ring structure represented by the following general formula (11), (12), (13), (14) or (15). The ring structure represented by the above general formula (10) is more preferably a ring structure represented by the following general formula (11) or (12).

The ring structure represented by the above general formula (20) is preferably a ring structure represented by the following general formula (21), (22), (23), (24) or (25).

The ring structure represented by the above general formula (30) is preferably a ring structure represented by the following general formula (31), (32), (33), (34) or (35).

[ Chemical formula 27 ]

[ Chemical formula 28 ]

[ Chemical formula 29 ]

(In the above general formulae (11), (12), (13), (14), (15), (21), (22), (23), (24), (25), (31), (32), (33), (34) and (35),

R ₁₁₁、R₁₁₃、R₁₂₁ and R ₁₂₃ are each independently of the other

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms, or

Fluoroalkyl having 1 to 50 carbon atoms,

R ₁₁₂、R₁₁₄、R₁₂₂ and R ₁₂₄ are each independently of the other

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

R ₁、R₂ and R ₃ each independently have the same meaning as R ₁～R₃ in the above general formula (10),

R ₄ and R ₅ are each independently the same as those of R ₄ and R ₅ in the above general formula (20),

R ₆、R₇ and R ₈ each independently have the same meaning as R ₆～R₈ in the above general formula (30),

*11 And 12 have the same meaning as 11 and 12 in formula (10) above,

*21 To 23 have the same meaning as 21 to 23 in the general formula (20),

*31 And 32 have the same meaning as 31 and 32 in formula (30) above. )

In this embodiment, the compound represented by the above general formula (1) is preferably a compound represented by the following general formula (110), the following general formula (120), or the following general formula (130).

[ Chemical formula 30 ]

(In the above-mentioned general formula (110),

The ring A1 and the ring B1 are each independently the same as the ring A1 and the ring B1 in the above general formula (1),

X has the same meaning as X in the above general formula (1),

V1 has the same meaning as V1 in the above general formula (1),

U1 has the same meaning as U1 in the above general formula (1),

U1 and V1 are different from each other,

Is not bonded with each other and is not bonded with each other,

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

A group represented by-N (R ₁₃₁₎(R₁₃₂),

A group represented by Si (R ₁₃₃)(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Halogen atom,

Cyano group,

A group represented by (R ₁₄₅)(R₁₄₆),

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

In the above-mentioned general formula (120),

The ring A1 and the ring C1 are each independently the same as the ring A1 and the ring C1 in the above general formula (1),

X has the same meaning as X in the above general formula (1),

V1 has the same meaning as V1 in the above general formula (1),

U1 has the same meaning as U1 in the above general formula (1),

U1 and V1 are different from each other,

Group consisting of R ₄ and R ₅

Is not bonded with each other and is not bonded with each other,

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

A group represented by-N (R ₁₃₁)(R₁₃₂),

A group represented by Si (R ₁₃₃)(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Halogen atom,

Cyano group,

A group represented by (R ₁₄₅)(R₁₄₆),

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

In the above-mentioned general formula (130),

The ring B1 has the same meaning as the ring B1 in the above-mentioned general formula (1),

V1 has the same meaning as V1 in the above general formula (1),

U1 has the same meaning as U1 in the above general formula (1),

V2 has the same meaning as V2 in the above general formula (3),

U2 has the same meaning as U2 in the above general formula (3),

More than 1 group of groups consisting of adjacent more than 2 of R ₁, R2, and R ₃

Is not bonded with each other and is not bonded with each other,

R ₁～R₃ which does not form the above-mentioned substituted or unsubstituted monocyclic ring and which does not form the above-mentioned substituted or unsubstituted condensed ring each independently has the same meaning as R ₁～R₃ in the above-mentioned general formula (110),

Is not bonded with each other and is not bonded with each other,

R ₆～R₈ which does not form the above-mentioned substituted or unsubstituted monocyclic ring and which does not form the above-mentioned substituted or unsubstituted condensed ring is each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

A group represented by-N (R ₁₃₁)(R₁₃₂),

A group represented by Si (R ₁₃₃)(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Halogen atom,

Cyano group,

A group represented by (R ₁₄₅)(R₁₄₆),

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

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

In this embodiment, it is preferable that R1 in the compound represented by the general formula (110) is not bonded to the ring A1.

In this embodiment, R4 in the compound represented by the general formula (120) is preferably a hydrogen atom.

In this embodiment, R ₁ in the compound represented by the general formula (130) is preferably not bonded to R ₈.

In the present embodiment, the compound represented by the general formula (110) is preferably a compound represented by the following general formula (110A),

The compound represented by the above general formula (130) is preferably a compound represented by the following general formula (130A).

[ Chemical formula 31 ]

(In the above-mentioned general formula (110A),

Ring A1 has the same meaning as ring A1 in the above-mentioned general formula (110),

X has the same meaning as X in the above general formula (110),

V1 has the same meaning as V1 in the above general formula (110),

U1 has the same meaning as U1 in the above general formula (110),

U1 and V1 are different from each other,

R ₁、R₂ and R ₃ are each independently the same as those of R ₁、R₂ and R ₃ in the above general formula (110),

R ₁ is not bonded to the ring A1,

In the above-mentioned general formula (130A),

V1 and U1 have the same meaning as V1 and U1 in the above general formula (130),

V2 and U2 have the same meaning as V2 and U2 in the above general formula (130),

U1 and V1 are different from each other,

U2 and V2 are different from each other,

R ₁、R₂、R₃、R₆、R₇ and R ₈ are each independently the same as those of R ₁、R₂、R₃、R₆、R₇ and R ₈ in the above general formula (130),

R ₁ and R ₈ are not bonded to each other,

In the above general formula (110A) and the above general formula (130A),

More than 1 group of groups consisting of 2 adjacent more than 2 of R ₉、R₁₀ and R ₁₁

Is not bonded with each other and is not bonded with each other,

R ₉、R₁₀ and R ₁₁ which do not form the above-mentioned substituted or unsubstituted monocyclic ring and which do not form the above-mentioned substituted or unsubstituted condensed ring are each independently

Hydrogen atom

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

A group represented by-N (R ₁₃₁)(R₁₃₂),

A group represented by Si (R ₁₃₃)(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Halogen atom,

Cyano group,

A group represented by (R ₁₄₅)(R₁₄₆),

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

In this embodiment, the compound represented by the general formula (110A) is preferably a compound represented by the following general formula (111A).

[ Chemical formula 32 ]

(In the above-mentioned general formula (111A),

Ring A1 has the same meaning as ring A1 in the above-mentioned general formula (110A),

X has the same meaning as X in the above general formula (110A),

R ₁、R₂、R₃、R₉、R₁₀ and R ₁₁ are each independently the same as those of R ₁、R₂、R₃、R₉、R₁₀ and R ₁₁ in the above general formula (110A),

Group consisting of R ₁₂ and R ₁₃

Is not bonded with each other and is not bonded with each other,

R ₁₂ which does not form the above-mentioned substituted or unsubstituted monocyclic ring and which does not form the above-mentioned substituted or unsubstituted condensed ring is

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

More than 1 group of groups consisting of 2 adjacent more than 2 of R ₁₃、R₁₄、R₁₅、R₁₆ and R ₁₇

Is not bonded with each other and is not bonded with each other,

R ₁₃ or R ₁₇ is bonded to R ₉ by a single bond or is not bonded to R ₉,

R ₁₃、R₁₄、R₁₅、R₁₆ and R ₁₇ which do not form the above-mentioned substituted or unsubstituted monocyclic ring and which do not form the above-mentioned substituted or unsubstituted condensed ring are each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

A group represented by-N (R ₁₃₁₎(R₁₃₂),

A group represented by Si (R ₁₃₃₎(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Halogen atom,

Cyano group,

A group represented by (R ₁₄₅₎(R₁₄₆),

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

Wherein at least any one of R ₁₃ and R ₁₇ which do not form a ring is a group other than a hydrogen atom and a halogen atom. )

In the compound represented by the above general formula (111A), it is preferable that neither R ₁₃ nor R ₁₇ is bonded to R ₉.

In the compound represented by the above general formula (111A), it is preferable that R ₁₃ and R ₁₇ which do not form a ring are each a group other than a hydrogen atom and a halogen atom.

In this embodiment, the compound represented by the general formula (110A) is preferably a compound represented by the following general formula (111B).

[ Chemical formula 33 ]

(In the above-mentioned general formula (111B),

X has the same meaning as X in the above general formula (110A),

Is not bonded with each other and is not bonded with each other,

More than 1 group of groups consisting of 2 adjacent more than 2 of R ₂₄、R₂₅、R₂₆、R₂₇ and R ₂₈

Is not bonded with each other and is not bonded with each other,

R ₁₃ is bonded to R ₂₈ by a single bond or is not bonded to R ₂₈,

R ₁₃、R₁₄、R₁₅、R₁₆、R₁₇、R₂₄、R₂₅、R₂₆、R₂₇ and R ₂₈ which do not form the above-mentioned substituted or unsubstituted monocyclic ring and which do not form the above-mentioned substituted or unsubstituted condensed ring are each independently

Hydrogen atom

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

A group represented by-N (R ₁₃₁)(R₁₃₂),

A group represented by Si (R ₁₃₃)(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Halogen atom,

Cyano group,

A group represented by (R ₁₄₅₎(R₁₄₆),

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

In the compound represented by the above general formula (111B), R ₁₃ is preferably not bonded to R ₂₈.

In this embodiment, in the above general formula (111B), R ₁ and R ₃ which do not form a ring are preferably hydrogen atoms.

In the present embodiment, the compound represented by the general formula (130A) is preferably a compound represented by the following general formula (131A).

[ Chemical formula 34 ]

(In the above-mentioned general formula (131A),

R ₁、R₂、R₃、R₆、R₇、R₈、R₉、R₁₀ and R ₁₁ are each independently the same as those of R ₁、R₂、R₃、R₆、R₇、R₈、R₉、R₁₀ and R ₁₁ in the above general formula (130A),

Group consisting of R ₁₂ and R ₁₃

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

Is not bonded with each other and is not bonded with each other,

Group consisting of R ₂₃ and R ₂₂

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

Is not bonded with each other and is not bonded with each other,

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

Is not bonded with each other and is not bonded with each other,

More than 1 group of groups consisting of 2 adjacent more than 2 of R ₁₈、R₁₉、R₂₀、R₂₁ and R ₂₂

Is not bonded with each other and is not bonded with each other,

R ₁₈ or R2 ₂ is bound to R ₁₁ by a single bond or is not bound to R ₁₁,

R ₁₂ and R ₂₃ which do not form the above-mentioned substituted or unsubstituted monocyclic ring and which do not form the above-mentioned substituted or unsubstituted condensed ring are each independently

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

R ₁₃、R₁₄、R₁₅、R₁₆ and R ₁₇ which do not form the above-mentioned substituted or unsubstituted monocyclic ring and do not form the above-mentioned substituted or unsubstituted condensed ring, and R ₁₈、R₁₉、R₂₀、R₂₁ and R ₂₂ 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

Hydrogen atom

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

A group represented by-N (R ₁₃₁)(R₁₃₂),

A group represented by Si (R ₁₃₃)(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Halogen atom,

Cyano group,

A group represented by (R ₁₄₅)(R₁₄₆),

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

Wherein at least any one of R ₁₃ and R ₁₇ which do not form a ring is a group other than a hydrogen atom and a halogen atom, and at least any one of R ₁₈ and R ₂₂ is a group other than a hydrogen atom and a halogen atom. )

In the compound represented by the above general formula (131A), it is preferable that neither R ₁₃ nor R ₁₇ is bonded to R ₉.

In the compound represented by the above general formula (131A), it is preferable that neither R ₁₈ nor R ₂₂ is bonded to R ₁₁.

In this embodiment, the compound represented by the above general formula (111B) is preferably a compound represented by the following general formula (111C), (111D), (111E), (111F), (111G), (111H), (111J) or (111K).

[ Chemical formula 35 ]

[ Chemical formula 36 ]

[ Chemical formula 37 ]

(Of the above general formula (111C), general formula (111D), general formula (111E), general formula (111F), general formula (111G), general formula (111H), general formula (111J) and general formula (111K),

X is

An oxygen atom,

A sulfur atom,

N(R₁₀₁)、

Si (R ₁₀₂)(R₁₀₃), or

C(R₁₀₄)(R₁₀₅),

Y is

An oxygen atom,

A sulfur atom,

N(R₁₀₆)、

Si (R ₁₀₇)(R₁₀₈), or

C(R₁₀₉)(R₁₁₀),

R ₁₀₂～R₁₀₅ in X and R ₁₀₇～R₁₁₀ in Y are each independently the same as R ₁₀₂～R₁₀₅ in the above general formula (1),

R ₁₀₆ are each independently

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

R ₁～R₃ and R ₉～R₁₁ are each independently the same as those of R ₁～R₃ and R ₉～R₁₁ in the above general formula (111B),

R ₁₃、R₁₄、R₁₅、R₁₆ and R ₁₇ are each independently the same as those of R ₁₃、R₁₄、R₁₅、R₁₆ and R ₁₇ in the above general formula (111B),

R ₁₃ is not bonded to R ₂₈,

R ₂₄、R₂₅、R₂₆、R₂₇ and R ₂₈ are each independently the same as those of R ₂₄、R₂₅、R₂₆、R₂₇ and R ₂₈ in the above general formula (111B),

More than 1 group of groups consisting of 2 adjacent more than 2 of R ₂₉、R₃₀、R₃₁ and R ₃₂

Is not bonded with each other and is not bonded with each other,

R ₂₉、R₃₀、R₃₁ and R ₃₂ 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 identical to the meanings of R ₁、R₂ and R ₃ in the above-mentioned general formula (111B),

More than 1 group of groups consisting of 2 adjacent more than 2 of R ₃₃、R₃₄、R₃₅ and R ₃₆

Is not bonded with each other and is not bonded with each other,

R ₃₃、R₃₄、R₃₅ and R ₃₆ 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 ₁, R2 and R ₃ which do not form the above-mentioned substituted or unsubstituted monocyclic ring and do not form the above-mentioned substituted or unsubstituted condensed ring in the above-mentioned general formula (111B),

R ₃₇ and R ₃₈ are each independently the same as R ₁, R2 and R ₃ in the above general formula (111B) which do not form the above substituted or unsubstituted monocyclic ring and do not form the above substituted or unsubstituted condensed ring,

Group consisting of R ₅₀ and R ₅₁

Is not bonded with each other and is not bonded with each other,

R ₅₀ and R ₅₁ which do not form the above-mentioned substituted or unsubstituted monocyclic ring and which do not form the above-mentioned substituted or unsubstituted condensed ring are each independently

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

Group consisting of R ₆₀ and R ₆₁

Is not bonded with each other and is not bonded with each other,

R ₆₀ and R ₆₁ which do not form the above-mentioned substituted or unsubstituted monocyclic ring and which do not form the above-mentioned substituted or unsubstituted condensed ring are each independently

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

R ₁₀₁ is represented by the following general formula (1116). )

[ Chemical formula 38 ]

(In the above-mentioned general formula (1116),

R ₃₉、R₄₀、R₄₁、R₄₂ and R ₄₃ are each independently the same as those of R ₁、R₂ and R ₃ in the above general formula (111B),

*61 Represents a bonding position to a nitrogen atom of N (R ₁₀₁) in the above general formula (111C) or general formula (111D). )

In the compounds represented by the general formulae (111C) and (111D), X is preferably an oxygen atom, N (R ₁₀₁) or C (R ₁₀₄)(R₁₀₅), more preferably an oxygen atom or N (R ₁₀₁), and still more preferably N (R ₁₀₁).

In the compounds represented by the general formulae (111D), (111G) and (111K), Y is preferably an oxygen atom, a sulfur atom or N (R ₁₀₆).

In the compound represented by the general formula (111E), R ₅₀ and R ₅₁ which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently preferably a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

In the compounds represented by the general formulae (111F) and (111G), R ₆₀ and R ₆₁ which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently preferably a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

In the present embodiment, among the compounds represented by the general formula (111E), the general formula (111F) and the general formula (111G), the compound represented by the general formula (111E) is preferable.

In the present embodiment, among the compounds represented by the general formula (111H), the general formula (111J) and the general formula (111K), the compound represented by the general formula (111H) is preferable.

Among the compounds according to this embodiment, it is preferable that,

In the above general formula (111C), R ₁、R₃、R₉、R₁₁ and R ₃₂ which do not form the above substituted or unsubstituted monocyclic ring and do not form the above substituted or unsubstituted condensed ring are a hydrogen atom,

In the above general formula (111D), R ₁、R₃、R₉ and R ₁₁ which do not form the above substituted or unsubstituted monocyclic ring and do not form the above substituted or unsubstituted condensed ring are hydrogen atoms,

In the above general formula (111E), R ₁、R₃、R₉、R₁₁ and R ₃₂ which do not form the above substituted or unsubstituted monocyclic ring and do not form the above substituted or unsubstituted condensed ring are a hydrogen atom,

In the above general formula (111F), R ₁、R₃、R₉ and R ₃₂ which do not form the above substituted or unsubstituted monocyclic ring and do not form the above substituted or unsubstituted condensed ring are hydrogen atoms,

In the above general formula (111G), R ₁、R₃ and R ₉ which do not form the above substituted or unsubstituted monocyclic ring and do not form the above substituted or unsubstituted condensed ring are a hydrogen atom,

In the above general formula (111H), R ₁、R₃、R₉、R₁₁ and R ₃₂ which do not form the above substituted or unsubstituted monocyclic ring and do not form the above substituted or unsubstituted condensed ring are hydrogen atoms,

In the above general formula (111J), R ₁、R₃、R₉ and R ₃₂ which do not form the above substituted or unsubstituted monocyclic ring and do not form the above substituted or unsubstituted condensed ring are a hydrogen atom,

In the above general formula (111K), R ₁、R₃ and R ₉ which do not form the above substituted or unsubstituted monocyclic ring and do not form the above substituted or unsubstituted condensed ring are hydrogen atoms.

Among the compounds according to the present embodiment, the compound represented by the general formula (111C) is preferably represented by the following general formula (111C-1), and the compound represented by the general formula (111D) is preferably represented by the following general formula (111D-1).

[ Chemical formula 39 ]

(In the above general formula (111C-1),

X is

Oxygen atom, or

N(R₁₀₁),

R ₁、R₃、R₉、R₁₁ and R ₃₂ are hydrogen atoms,

R ₂、R₁₀、R₁₃～R₁₇、R₂₄～R₂₈、R₂₉～R₃₁ is each independently the same as R ₂、R₁₀、R₁₃～R₁₇、R₂₄～R₂₈、R₂₉～R₃₁ in the above general formula (111C),

In the above general formula (111D-1),

X is

Oxygen atom, or

N(R₁₀₁),

Y is

Oxygen atom, or

A sulfur atom is used as a source of oxygen,

R ₉ and R ₁₁ are hydrogen atoms,

R ₁～R₃、R₁₀、R₁₃～R₁₇、R₂₄～R₂₈、R₃₃～R₃₆ is each independently the same as R ₁～R₃、R₁₀、R₁₃～R₁₇、R₂₄～R₂₈、R₃₃～R₃₆ in the above general formula (111D),

R ₁₀₁ is represented by the following general formula (1116). )

[ Chemical formula 40 ]

(In the above-mentioned general formula (1116),

R ₃₉～R₄₃ is each independently the same as R ₁、R₂ and R ₃ in the above general formula (111B),

*61 Represents a bonding position to a nitrogen atom of N (R ₁₀₁) in the above general formula (111C-1) or general formula (111D-1). )

In the compounds represented by the above general formula (111C-1) and the above general formula (111D-1), X is preferably N (R ₁₀₁).

In the compounds according to the present embodiment, the substituent expressed as "substituted or unsubstituted" is preferably

Halogen atom,

Unsubstituted alkyl group having 1 to 25 carbon atoms,

Unsubstituted aryl group having 6 to 25 ring carbon atoms, or

Unsubstituted heterocyclic groups having 5 to 25 ring-forming atoms.

Unsubstituted alkyl group having 1 to 10 carbon atoms,

Unsubstituted aryl group having 6 to 12 ring carbon atoms, or

Unsubstituted heterocyclic groups having 5 to 12 ring-forming atoms.

In the compounds according to this embodiment, it is described that the "substituted or unsubstituted" group is preferably an "unsubstituted" group.

(Method for producing Compound according to the embodiment)

The compound according to the present embodiment can be produced by a synthetic method described in examples described below, or by using a known substitution reaction and starting materials corresponding to the target substance in a manner similar to the synthetic method.

(Specific examples of the compounds according to the present embodiment)

Specific examples of the compounds according to the present embodiment include the following compounds. However, the present invention is not limited to these specific examples. In the present specification, deuterium atoms are denoted by D, protium atoms are denoted by H, or description thereof is omitted.

[ Chemical formula 41 ]

[ Chemical formula 42 ]

[ Chemical formula 43 ]

[ Chemical formula 44 ]

[ Chemical formula 45 ] and [ 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 ]

[ Chemical formula 65 ]

[ Chemical formula 66 ]

[ Chemical formula 67 ]

[ Chemical formula 68 ]

[ Chemical formula 69 ]

[ Chemical formula 70 ]

[ Chemical formula 71 ]

[ Chemical formula 72 ]

[ Chemical formula 73 ]

[ Chemical formula 74 ]

[ Chemical formula 75 ]

[ Chemical formula 76 ]

[ Chemical formula 77 ]

[ Chemical formula 78 ]

[ Chemical formula 79 ]

[ Chemical formula 80 ]

[ Chemical formula 81 ]

[ Chemical formula 82 ]

[ Chemical formula 83 ]

[ Chemical formula 84 ]

[ Chemical formula 85 ]

[ Chemical formula 86 ]

[ Chemical formula 87 ]

[ Chemical formula 88 ]

[ Chemical formula 89 ]

[ Chemical formula 90 ]

[ Chemical formula 91 ]

[ Chemical formula 92 ]

[ Chemical formula 93 ]

[ Chemical formula 94 ]

[ Chemical formula 95 ]

[ Chemical formula 96 ]

[ Chemical formula 97 ]

[ Chemical formula 98 ]

[ Chemical formula 99 ]

[ Chemical formula 100 ]

[ Chemical formula 101 ]

[ Chemical formula 102 ]

[ 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 ]

[ Chemical formula 113 ]

[ Chemical formula 114 ]

[ Chemical formula 115 ]

[ 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 ]

[ Formula 128 ]

[ Chemical formula 129 ]

[ Chemical formula 130 ]

[ Chemical formula 131 ]

[ Chemical formula 132 ]

[ Chemical formula 133 ]

[ Chemical formula 134 ]

[ Chemical formula 135 ]

[ Chemical formula 136 ]

[ Chemical formula 137 ]

[ Chemical formula 138 ]

[ Chemical formula 139 ]

[ Chemical formula 140 ]

[ 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 ]

Second embodiment

(Material for organic electroluminescent element)

The material for an organic electroluminescent element according to the present embodiment contains the compound according to the first embodiment. As one embodiment, there is a material for an organic electroluminescent element containing only the compound according to the first embodiment, and as another embodiment, there is a material for an organic electroluminescent element containing the compound according to the first embodiment and another compound different from the compound according to the first embodiment.

In the material for an organic electroluminescent element according to the present embodiment, the compound according to the first embodiment is preferably a dopant material. In this case, the material for an organic electroluminescent element may contain the compound according to the first embodiment as a dopant material and other compounds such as a host material.

The compound according to the first embodiment is useful as a material for an organic EL element, a material for a light-emitting layer of the organic EL element, and particularly a blue light-emitting material for a light-emitting layer.

Third embodiment

[ Organic electroluminescent element ]

The organic EL element according to the present embodiment will be described.

The organic EL element according to the present embodiment includes an organic layer between both electrodes of an anode and a cathode. The organic layer comprises at least one layer formed of an organic compound. Or the organic layer is formed by laminating a plurality of layers formed of an organic compound. The organic layer may further comprise an inorganic compound.

In the organic EL element according to the present embodiment, the organic layer contains the compound according to the first embodiment. That is, the organic EL element according to the present embodiment includes a cathode, an anode, and an organic layer interposed between the cathode and the anode, and the organic layer contains the compound according to the first embodiment as a first compound.

In the organic EL element of the present embodiment, it is preferable that the organic layer includes a light-emitting layer, and the light-emitting layer contains the compound according to the first embodiment as the first compound.

The organic EL element according to the present embodiment includes a cathode, an anode, and 1 or more organic layers disposed between the cathode and the anode, and at least 1 layer among the 1 or more organic layers contains the compound according to the first embodiment as a first compound.

The organic EL element according to the present embodiment includes a cathode, an anode, and 1 or more light-emitting layers disposed between the cathode and the anode, and at least 1 layer among the 1 or more light-emitting layers contains the compound according to one embodiment of the present invention as a first compound.

As the third embodiment, the organic EL element according to the present embodiment may be an organic EL element having a single light-emitting layer.

The general structure of an organic EL element according to an embodiment of the present invention will be described with reference to fig. 1. Fig. 1 shows a general structure of an example of an organic EL element according to a third embodiment.

An organic EL element 1 according to an embodiment of the present invention includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10 disposed between the anode 3 and the cathode 4. The organic layer 10 is formed by stacking the 1 st organic layer 67, the light-emitting layer 5, and the 2 nd organic layer 89 in this order from the anode 3 side. Each of the 1 st organic layer 67 and the 2 nd organic layer 89 may be a single layer or may be formed of a plurality of layers.

In addition, the 1 st organic layer 67 may include a hole transport region. The hole transport region may include at least any one layer selected from a hole injection layer, a hole transport layer, an electron blocking layer, and the like. The 2 nd organic layer 89 may contain an electron transport region. The electron transport region may include at least any one layer selected from an electron injection layer, an electron transport layer, a hole blocking layer, and the like. For example, the 1 st organic layer 67 may be formed by stacking a hole injection layer and a hole transport layer in this order from the anode 3 side. The 2 nd organic layer 89 may be formed by stacking an electron transport layer and an electron injection layer in this order from the anode 3 side. The organic EL element 1 may be configured by stacking a hole injection layer, a hole transport layer, a light emitting layer 5, an electron transport layer, and an electron injection layer in this order from the anode 3 side. The present invention is not limited to the organic EL element having the structure shown in fig. 1.

The compound according to the first embodiment is contained in the 1 st organic layer 67, the light-emitting layer 5, or the 2 nd organic layer 89. In one embodiment, the compound according to the first embodiment is contained in the light-emitting layer 5. The compound according to the first embodiment can function as a dopant material in the light-emitting layer 5.

In the organic EL element according to the present embodiment, the light-emitting layer preferably does not contain a metal complex. In the organic EL element according to the present embodiment, the light-emitting layer preferably does not contain a boron-containing complex.

In the organic EL element according to the present embodiment, the light-emitting layer preferably does not contain a phosphorescent material (dopant material). In addition, the light-emitting layer also preferably does not contain a heavy metal complex or a phosphorescent rare earth metal complex.

In the organic EL element according to the third embodiment, a compound according to an embodiment of the present invention as a first compound and a compound represented by general formula (H10) described below as a second compound may be used in combination in a light-emitting layer of the organic EL element.

The following is a description of the compound represented by the general formula (H10).

(Compound represented by the general formula (H10))

The compound represented by the general formula (H10) is described.

[ Chemical formula 154 ]

[ In the above-mentioned general formula (H10),

More than 1 group of groups consisting of adjacent more than 2 of R ₁₀₁～R₁₁₀

Is not bonded with each other and is not bonded with each other,

R ₁₀₁～R₁₁₀ which does not form the above-mentioned substituted or unsubstituted monocyclic ring and which does not form the above-mentioned substituted or unsubstituted condensed ring is each independently

A hydrogen atom,

Substituent R, or

A group represented by the following general formula (H11),

Wherein at least 1 of R ₁₀₁～R₁₁₀ which does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring is a group represented by the following general formula (H11),

When there are 2 or more groups represented by the following general formula (H11), 2 or more groups represented by the following general formula (H11) are the same or different from each other.

-L₁₀₁-Ar₁₀₁(H11)

(In the above-mentioned general formula (H11),

L ₁₀₁ is

A single bond,

Substituted or unsubstituted arylene group having 6 to 50 ring members, or

A substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring members,

Ar ₁₀₁ is

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

The substituent R is

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by Si (R ₉₀₁)(R₉₀₂)(R₉₀₃),

A group represented by-O- (R ₉₀₄),

A group represented by S- (R ₉₀₅),

A group represented by-N (R ₉₀₆₎(R₉₀₇),

Halogen atom, cyano group, nitro group,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

When there are 2 or more substituents R, 2 or more substituents R are the same or different from each other,

R ₉₀₁～R₉₀₇ are each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

Where there are plural R ₉₀₁, plural R ₉₀₁ are the same or different from each other,

Where there are plural R ₉₀₂, plural R ₉₀₂ are the same or different from each other,

Where there are plural R ₉₀₃, plural R ₉₀₃ are the same or different from each other,

Where there are plural R ₉₀₄, plural R ₉₀₄ are the same or different from each other,

Where there are plural R ₉₀₅, plural R ₉₀₅ are the same or different from each other,

Where there are plural R ₉₀₆, plural R ₉₀₆ are the same or different from each other,

In the case where there are plural R ₉₀₇, plural R ₉₀₇ are the same or different from each other. ) ]

The compound represented by the above general formula (H10) may have a deuterium atom as a hydrogen atom.

In one embodiment, at least 1 of Ar ₁₀₁ in the above general formula (H10) is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

In one embodiment, at least 1 of Ar ₁₀₁ in the above general formula (H10) is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.

In one embodiment, all Ar ₁₀₁ in the above general formula (H10) is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms. The Ar ₁₀₁ may be the same as or different from each other.

In one embodiment, 1 of Ar ₁₀₁ in the above general formula (H10) is a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, and the rest of Ar ₁₀₁ is a substituted or unsubstituted aryl group having 6 to 50 ring-forming atoms. The Ar ₁₀₁ may be the same as or different from each other.

In one embodiment, at least 1 of L ₁₀₁ in the above formula (H10) is a single bond.

In one embodiment, L ₁₀₁ in the above formula (H10) is a single bond.

In one embodiment, at least 1 of L ₁₀₁ in the above general formula (H10) is a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms.

In one embodiment, at least 1 of L ₁₀₁ in the above formula (H10) is a substituted or unsubstituted phenylene group, or a substituted or unsubstituted naphthylene group.

In one embodiment, the group represented by-L ₁₀₁-Ar₁₀₁ in the above formula (H10) is selected from

Substituted or unsubstituted phenyl,

Substituted or unsubstituted naphthyl,

Substituted or unsubstituted biphenyl,

Substituted or unsubstituted phenanthryl,

Substituted or unsubstituted is a benzophenanthryl group,

Substituted or unsubstituted fluorenyl,

Substituted or unsubstituted benzofluorenyl group,

Substituted or unsubstituted dibenzofuranyl group,

Substituted or unsubstituted naphthalene benzofuranyl group,

Substituted or unsubstituted dibenzothienyl, and

A substituted or unsubstituted carbazolyl group.

In one embodiment, the substituents R in the above formula (H10) are each independently

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

A group represented by Si (R ₉₀₁)(R₉₀₂)(R₉₀₃),

A group represented by-O- (R ₉₀₄),

A group represented by S- (R ₉₀₅),

A group represented by-N (R ₉₀₆)(R₉₀₇),

Halogen atoms, cyano groups, nitro groups, or

Substituted or unsubstituted aryl groups having 6 to 50 ring-forming carbon atoms,

R ₉₀₁～R₉₀₇ is as defined above for formula (H10).

In one embodiment, the "substituted or unsubstituted" substituents in the above formula (H10) are each independently

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by Si (R ₉₀₁)(R₉₀₂)(R₉₀₃),

A group represented by-O- (R ₉₀₄),

A group represented by S- (R ₉₀₅),

A group represented by-N (R ₉₀₆)(R₉₀₇),

Halogen atom, cyano group, nitro group,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

R ₉₀₁～R₉₀₇ is as defined above for formula (H10).

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

A group represented by Si (R ₉₀₁)(R₉₀₂)(R₉₀₃),

A group represented by-O- (R ₉₀₄),

A group represented by S- (R ₉₀₅),

A group represented by-N (R ₉₀₆)(R₉₀₇),

Halogen atoms, cyano groups, nitro groups, or

R ₉₀₁～R₉₀₇ is as defined above for formula (H10).

In one embodiment, the substituents expressed as "substituted or unsubstituted" in the above formula (H10) are selected from

An alkyl group having 1 to 18 carbon atoms,

Aryl groups having 6 to 18 ring-forming carbon atoms, and

A heterocyclic group having 5 to 18 ring atoms.

In one embodiment, the substituent in the expression "substituted or unsubstituted" in the above general formula (H10) is an alkyl group having 1 to 5 carbon atoms.

In one embodiment, the compound represented by the general formula (H10) is a compound represented by the following general formula (H20).

[ Chemical formula 155 ]

(In the general formula (H20), R ₁₀₁～R₁₀₈、L₁₀₁ and Ar ₁₀₁ are the same as defined in the above general formula (H10))

The compound represented by the above general formula (H20) may have a deuterium atom as a hydrogen atom.

That is, in one embodiment, the compound represented by the above general formula (H10) or the general formula (H20) has at least 2 groups represented by the above general formula (H11).

In one embodiment, the compound of the above formula (H10) or formula (H20) has 2 or 3 groups of the above formula (H11).

In one embodiment, none of the group consisting of 2 or more adjacent ones of R ₁₀₁～R₁₁₀ in the above general formula (H10) and general formula (H20) is bonded to each other.

In one embodiment, R ₁₀₁～R₁₁₀ in the above general formula (H10) and general formula (H20) is a hydrogen atom.

In one embodiment, the compound represented by the general formula (H20) is a compound represented by the following general formula (H30).

[ Chemical formula 156 ]

(In the above general formula (H30), L ₁₀₁ and Ar ₁₀₁ are the same as defined in the above general formula (H10),

None of the groups consisting of 2 or more adjacent ones of R _101A～R_108A are bonded to each other,

R _101A～R_108A are each independently

A hydrogen atom, or a substituent R,

The substituent R is as defined in the above formula (H10). )

That is, the compound represented by the above general formula (H30) is a compound having 2 groups represented by the above general formula (H11).

The compound represented by the above general formula (H30) has substantially only protium atoms as hydrogen atoms.

The term "having substantially only protium atoms" means that the ratio of protium is 90 mol% or more, 95 mol% or more, or 99 mol% or more based on the total of the compound having only protium atoms as hydrogen atoms of the same structure (protium) and the compound having deuterium atoms of the same structure (deuterium).

In one embodiment, the compound represented by the general formula (H30) is a compound represented by the following general formula (H31).

[ Chemical formula 157 ]

(In the above general formula (H31), L ₁₀₁ and Ar ₁₀₁ are the same as defined in the above general formula (H10),

R _101A～R_108A is as defined above for the general formula (H30),

X _b is an oxygen atom, a sulfur atom, N (R ₃₃₁), or C (R ₃₃₂)(R₃₃₃),

1 Of R ₁₂₁～R₁₂₈ and R ₃₃₁～R₃₃₃ is a single bond to L ₁₀₁,

More than 1 group of the group consisting of 2 or more adjacent ones of R ₁₂₁～R₁₂₈ other than a single bond bonded to L ₁₀₁

Is not bonded with each other and is not bonded with each other,

R ₁₂₁～R₁₂₈ which is not a single bond to L ₁₀₁ and does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring is each independently

Hydrogen atom, or

The substituent R is a substituent R,

The substituents R are as defined in the general formula (H10),

R ₃₃₁～R₃₃₃ which is not a single bond to L ₁₀₁ is each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

Where there are plural R ₃₃₁, plural R ₃₃₁ are the same or different from each other,

Where there are plural R ₃₃₂, plural R ₃₃₂ are the same or different from each other,

In the case where there are plural R ₃₃₃, plural R ₃₃₃ are the same or different from each other. )

In one embodiment, the compound represented by the general formula (H31) is a compound represented by the following general formula (H32).

[ Chemical formula 158 ]

(In the above general formula (H32), R _101A～R_108A、L₁₀₁、Ar₁₀₁、R₁₂₁～R₁₂₈、R₃₃₂ and R ₃₃₃ are the same as defined in the above general formula (H31))

In one embodiment, the compound represented by the general formula (H31) is a compound represented by the following general formula (H33).

[ Chemical formula 159 ]

(In the above general formula (H33), R _101A～R_108A、L₁₀₁、Ar₁₀₁ and R ₁₂₁～R₁₂₈ are the same as defined in the above general formula (H31),

Xc is an oxygen atom, a sulfur atom, or NR ₃₃₁,

R ₃₃₁ is as defined above for formula (H31). )

In one embodiment, the compound represented by the general formula (H31) is a compound represented by the following general formula (H34).

[ Chemical formula 160 ]

(In the above general formula (H34), R _101A～R_108A、L₁₀₁ and Ar ₁₀₁ are the same as defined in the above general formula (H31),

X _c is an oxygen atom, a sulfur atom or NR ₃₃₁,

R ₃₃₁ is as defined above for the general formula (H31),

1 Of R _121A～R_128A is a single bond to L ₁₀₁,

None of the groups consisting of 2 or more adjacent ones of R _121A～R_128A other than the single bond to L ₁₀₁ are bonded to each other,

R _121A～R_128A which is not a single bond to L ₁₀₁ is each independently

Hydrogen atom, or

The substituent R is a substituent R,

The substituent R is as defined in the above formula (H10). )

In one embodiment, the compound represented by the general formula (H31) is a compound represented by the following general formula (H35).

[ Chemical formula 161 ]

[ In the above general formula (H35), R _101A～R_108A、L₁₀₁、Ar₁₀₁ and X _b are as defined in the above general formula (H31).

None of the groups consisting of 2 or more adjacent ones of R _121A～R_124A are bonded to each other,

Any one of R _125A and R _126A、R_126A and R _127A, and R _127A and R _128A is bonded to each other to form a ring represented by the following general formula (H35 a) or general formula (H35 b).

[ Chemical formula 162 ]

(In the above general formulae (H35 a) and (H35 b),

2 Are bonded to any one of R _125A and R _126A、R_126A and R _127A, respectively, and R _127A and R _128A,

R ₃₄₁～R₃₄₄ are each independently

Hydrogen atom, or

The substituent R is a substituent R,

The substituents R are as defined in the general formula (H10),

X _d is an oxygen atom or a sulfur atom. )

R _121A～R_124A, 1 of R _125A～R_128A and R ₃₄₁～R₃₄₄ which do not form a ring represented by the above general formula (H35 a) or the general formula (H35 b) is a single bond bonded to L ₁₀₁,

R _121A～R_124A which is not a single bond to L ₁₀₁, and R _125A～R_128A which is not a single bond to L ₁₀₁ and does not form a ring represented by the above general formula (H35 a) or general formula (H35 b) are each independently

Hydrogen atom, or

The substituent R is a substituent R,

The substituent R is as defined in the above formula (H10). ]

In one embodiment, the compound represented by the general formula (H35) is a compound represented by the following general formula (H36).

[ Chemical formula 163 ]

(In the above general formula (H36), R _101A～R_108A、L₁₀₁ and Ar ₁₀₁ are the same as defined in the above general formula (H35), and R _125B～R_128B each independently has the same meaning as R _125A～R_128A in the above general formula (H35))

In one embodiment, the compound represented by the general formula (H34) is a compound represented by the following general formula (H37).

[ Chemical formula 164 ]

(In the above general formula (H37), R _101A～R_108A、R_125A～R_128A、L₁₀₁ and Ar ₁₀₁ are the same as defined in the above general formula (H34))

In one embodiment, R _101A～R_108A in the above general formulae (H30) to (H37) is a hydrogen atom.

In one embodiment, the compound represented by the general formula (H10) is a compound represented by the following general formula (H40).

[ Chemical formula 165 ]

(In the above general formula (H40), L ₁₀₁ and Ar ₁₀₁ are the same as those in the above general formula (H10), and 1 or more groups of 2 or more adjacent groups among R _101A and R _103A～R_108A

Is not bonded with each other and is not bonded with each other,

R _101A and R _103A～R_108A which do not form the above-mentioned substituted or unsubstituted monocyclic ring and which do not form the above-mentioned substituted or unsubstituted condensed ring are each independently

A hydrogen atom, or a substituent R,

The substituent R is as defined in the above formula (H10). )

That is, the compound represented by the above general formula (H40) is a compound having 3 groups represented by the above general formula (H11). The compound represented by the general formula (H40) has substantially only protium atoms as hydrogen atoms.

In one embodiment, the compound represented by the above general formula (H40) is represented by the following general formula (H41).

[ Chemical formula 166 ]

(In the above general formula (H41), L ₁₀₁ and Ar ₁₀₁ are the same as those in the above general formula (H40))

In one embodiment, the compound represented by the general formula (H40) is a compound represented by any one of the following general formulae (H42-1) to (H42-3).

[ Chemical formula 167 ]

(In the above general formula (H42-1) to general formula (H42-3), R _101A、R_103A～R_108A、L₁₀₁ and Ar ₁₀₁ are the same as those in the above general formula (H40))

In one embodiment, the compounds represented by the general formulae (H42-1) to (H42-3) are compounds represented by any one of the following general formulae (H43-1) to (H43-3).

[ Chemical formula 168 ]

(In the above general formula (H43-1) to general formula (H43-3), L ₁₀₁ and Ar ₁₀₁ are the same as those in the above general formula (H40))

In one embodiment, the groups represented by-L ₁₀₁-Ar₁₀₁ in the above general formula (H40), general formula (H41), general formula (H42-1) to general formula (H42-3) and general formula (H43-1) to general formula (H43-3) are selected from

Substituted or unsubstituted phenyl,

Substituted or unsubstituted naphthyl,

Substituted or unsubstituted biphenyl,

Substituted or unsubstituted phenanthryl,

Substituted or unsubstituted is a benzophenanthryl group,

Substituted or unsubstituted fluorenyl,

Substituted or unsubstituted benzofluorenyl group,

Substituted or unsubstituted dibenzofuranyl group,

Substituted or unsubstituted naphthalene benzofuranyl group,

Substituted or unsubstituted dibenzothienyl, and

A substituted or unsubstituted carbazolyl group.

In one embodiment, the compound represented by the above general formula (H10) or the general formula (H20) contains a compound in which at least 1 of hydrogen atoms contained in these compounds is deuterium atoms.

In one embodiment, the compound of formula (H20) above

R ₁₀₁～R₁₀₈ as a hydrogen atom,

A hydrogen atom of R ₁₀₁～R₁₀₈ as the substituent R,

L ₁₀₁ has a hydrogen atom,

A hydrogen atom of a substituent of L ₁₀₁,

Ar ₁₀₁ has a hydrogen atom and

The substituents of Ar10 ₁ having hydrogen atoms

At least 1 of them is a deuterium atom.

The compounds represented by the general formulae (H30) to (H37) include compounds having deuterium atoms as at least 1 of hydrogen atoms included in these compounds.

In one embodiment, at least 1 of the hydrogen atoms bonded to the carbon atoms constituting the anthracene skeleton in the compounds represented by the general formulae (H30) to (H37) is a deuterium atom.

In one embodiment, the compound represented by the general formula (H30) is a compound represented by the following general formula (H30D).

[ Chemical formula 169 ]

(In the above general formula (H30D), R _101A～R_108A、L₁₀₁ and Ar ₁₀₁ are as defined in the above general formula (H30).

Wherein,

R _101A～R_108A as a hydrogen atom,

A hydrogen atom of R _101A～R_108A as the substituent R,

L ₁₀₁ has a hydrogen atom,

A hydrogen atom of a substituent of L ₁₀₁,

Ar ₁₀₁ has a hydrogen atom, and

The substituents of Ar ₁₀₁ having hydrogen atoms

At least 1 of them is a deuterium atom. )

That is, the compound represented by the general formula (H30D) is a compound in which at least 1 of hydrogen atoms included in the compound represented by the general formula (H30) is deuterium atoms.

In one embodiment, at least 1 of R _101A～R_108A as a hydrogen atom in the above general formula (H30D) is a deuterium atom.

In one embodiment, the compound represented by the general formula (H30D) is a compound represented by the following general formula (H31D).

[ Chemical formula 170 ]

(In the above general formula (H31D), R _101A～R_108A、L₁₀₁ and Ar ₁₀₁ are the same as defined in the above general formula (H30D),

X _d is an oxygen atom or a sulfur atom,

1 Of R ₁₂₁～R₁₂₈ is a single bond to L ₁₀₁,

Is not bonded with each other and is not bonded with each other,

Hydrogen atom, or

The substituent R is a substituent R,

The substituent R is as defined in the above formula (H10).

Wherein,

R _101A～R_108A as a hydrogen atom,

A hydrogen atom of R _101A～R_108A as the substituent R,

L ₁₀₁ has a hydrogen atom,

A hydrogen atom of a substituent of L ₁₀₁,

Ar ₁₀₁ has a hydrogen atom,

The substituents of Ar ₁₀₁ having hydrogen atoms

R ₁₂₁～R₁₂₈ as a hydrogen atom, and

R ₁₂₁～R₁₂₈ as the substituent R has a hydrogen atom

At least 1 of them is a deuterium atom. )

In one embodiment, the compound represented by the general formula (H31D) is a compound represented by the following general formula (H32D).

[ Chemical formula 171 ]

(In the above general formula (H32D), R _101A～R_108A、L₁₀₁ and Ar ₁₀₁ are the same as defined in the above general formula (H31D), and R _125A～R_128A each independently has the same meaning as R ₁₂₅～R₁₂₈ in the above general formula (H31D).

Wherein,

R _101A～R_108A as a hydrogen atom,

A hydrogen atom of R _101A～R_108A as the substituent R,

R _125A～R_128A as a hydrogen atom,

A hydrogen atom of R _125A～R_128A as the substituent R,

A hydrogen atom bonded to a carbon atom of the dibenzofuran skeleton in the general formula (H32D),

L ₁₀₁ has a hydrogen atom,

A hydrogen atom of a substituent of L ₁₀₁,

Ar ₁₀₁ has a hydrogen atom, and

The substituents of Ar ₁₀₁ having hydrogen atoms

At least 1 of them is a deuterium atom. )

In one embodiment, the compound represented by the above general formula (H32D) is a compound represented by the following general formula (H32D-1) or general formula (H32D-2).

[ Chemical formula 172 ]

(In the above general formula (H32D-1) and general formula (H32D-2), R _101A～R_108A、R_125A～R_128A、L₁₀₁ and Ar ₁₀₁ are as defined in the above general formula (H32D).

Wherein,

R _101A～R_108A as a hydrogen atom,

A hydrogen atom of R _101A～R_108A as the substituent R,

R _125A～R_128A as a hydrogen atom,

A hydrogen atom of R _125A～R_128A as the substituent R,

A hydrogen atom bonded to a carbon atom of a dibenzofuran skeleton in the general formulae (H32D-1) and (H32D-2),

L ₁₀₁ has a hydrogen atom,

A hydrogen atom of a substituent of L ₁₀₁,

Ar ₁₀₁ has a hydrogen atom, and

The substituents of Ar ₁₀₁ having hydrogen atoms

At least 1 of them is a deuterium atom. )

In one embodiment, at least 1 of the hydrogen atoms of the compounds represented by the general formula (H40), the general formula (H41), the general formula (H42-1) to the general formula (H42-3) or the general formula (H43-1) to the general formula (H43-3) is a deuterium atom.

In one embodiment, at least 1 of the hydrogen atoms bonded to the carbon atoms constituting the anthracene skeleton in the compound represented by the general formula (H41) is a deuterium atom.

In one embodiment, the compound represented by the general formula (H40) is a compound represented by the following general formula (H40D).

[ Chemical formula 173 ]

(In the above general formula (H40D), L ₁₀₁ and Ar ₁₀₁ are the same as defined in the above general formula (H10),

None of the groups consisting of adjacent 2 or more of R _101A and R _103A～R_108A are bonded to each other,

R _101A and R _103A～R_108A are each independently of the other

Hydrogen atom, or

The substituent R is a substituent R,

The substituent R is as defined in the above formula (H10).

Wherein,

R _101A and R _103A～R_108A as hydrogen atoms,

R _101A and R _103A～R_108A as the substituent R have a hydrogen atom,

L ₁₀₁ has a hydrogen atom,

A hydrogen atom of a substituent of L ₁₀₁,

Ar ₁₀₁ has a hydrogen atom, and

The substituents of Ar ₁₀₁ having hydrogen atoms

At least 1 of them is a deuterium atom. )

In one embodiment, at least 1 of R _101A and R _103A～R_108A in the above formula (H40D) is a deuterium atom.

In one embodiment, the compound represented by the general formula (H40D) is a compound represented by the following general formula (H41D).

[ Chemical formula 174 ]

(In the above general formula (H41D), L ₁₀₁ and Ar ₁₀₁ are as defined in the above general formula (H40D).

Wherein in the formula (H41D)

Hydrogen atoms bonded to carbon atoms constituting the anthracene skeleton,

L ₁₀₁ has a hydrogen atom,

A hydrogen atom of a substituent of L ₁₀₁,

Ar ₁₀₁ has a hydrogen atom, and

The substituents of Ar ₁₀₁ having hydrogen atoms

At least 1 of them is a deuterium atom. )

In one embodiment, the compound represented by the general formula (H40D) is a compound represented by any one of the following general formulae (H42D-1) to (H42D-3).

[ Chemical formula 175 ]

(In the above general formula (H42D-1) to general formula (H42D-3), R _101A、R_103A～R_108A、L₁₀₁ and Ar ₁₀₁ are the same as those in the above general formula (H40D).

Wherein the above formula (H42D-1)

R _101A and R _103A～R_108A as hydrogen atoms,

R _101A and R _103A～R_108A as the substituent R have a hydrogen atom,

L ₁₀₁ has a hydrogen atom,

A hydrogen atom of a substituent of L ₁₀₁,

Ar ₁₀₁ has a hydrogen atom,

A hydrogen atom of Ar ₁₀₁ and

The hydrogen atom bonded to the carbon atom constituting the phenyl group in the above general formula (H42D-1)

At least 1 of them is a deuterium atom,

Of the above formula (H42D-2)

R _101A and R _103A～R_108A as hydrogen atoms,

R _101A and R _103A～R_108A as the substituent R have a hydrogen atom,

L ₁₀₁ has a hydrogen atom,

A hydrogen atom of a substituent of L ₁₀₁,

Ar ₁₀₁ has a hydrogen atom,

A hydrogen atom of Ar ₁₀₁ and

A hydrogen atom bonded to a carbon atom constituting a naphthyl group in the above general formula (H42D-2)

At least 1 of them is a deuterium atom,

Of the above formula (H42D-3)

R _101A and R _103A～R_108A as hydrogen atoms,

R _101A and R _103A～R_108A as the substituent R have a hydrogen atom,

L ₁₀₁ has a hydrogen atom,

A hydrogen atom of a substituent of L ₁₀₁,

Ar ₁₀₁ has a hydrogen atom,

A hydrogen atom of Ar ₁₀₁ and

A hydrogen atom bonded to a carbon atom constituting a naphthyl group in the above general formula (H42D-3)

At least 1 of them is a deuterium atom. )

In one embodiment, the compounds represented by the general formulae (H42D-1) to (H42D-3) are compounds represented by any one of the following general formulae (H43D-1) to (H43D-3).

[ Chemical formula 176 ]

(In the above general formula (H43D-1) to general formula (H43D-3), L ₁₀₁ and Ar ₁₀₁ are the same as those in the above general formula (H40D).

Wherein,

A hydrogen atom bonded to a carbon atom constituting an anthracene skeleton in the above general formula (H43D-1),

L ₁₀₁ has a hydrogen atom,

A hydrogen atom of a substituent of L ₁₀₁,

Ar ₁₀₁ has a hydrogen atom,

A hydrogen atom of Ar ₁₀₁ and

The hydrogen atom bonded to the carbon atom constituting the phenyl group in the above formula (H43D-1)

At least 1 of them is a deuterium atom,

A hydrogen atom bonded to a carbon atom constituting an anthracene skeleton in the above general formula (H43D-2),

L ₁₀₁ has a hydrogen atom,

A hydrogen atom of a substituent of L ₁₀₁,

Ar10 ₁ has a hydrogen atom,

A hydrogen atom of Ar ₁₀₁ and

A hydrogen atom bonded to a carbon atom constituting a naphthyl group in the above general formula (H43D-2)

At least 1 of them is a deuterium atom,

A hydrogen atom bonded to a carbon atom constituting an anthracene skeleton in the above general formula (H43D-3),

L ₁₀₁ has a hydrogen atom,

A hydrogen atom of a substituent of L ₁₀₁,

Ar ₁₀₁ has a hydrogen atom,

A hydrogen atom of Ar ₁₀₁ and

A hydrogen atom bonded to a carbon atom constituting a naphthyl group in the above formula (H43D-3)

At least 1 of them is a deuterium atom. )

In one embodiment, at least 1 of Ar ₁₀₁ in the compound represented by the above general formula (H20) is a monovalent group having a structure represented by the following general formula (H50).

[ Chemical formula 177 ]

(In the above general formula (H50),

X ₁₅₁ is an oxygen atom, a sulfur atom, or C (R ₁₆₁)(R₁₆₂),

1 Of R ₁₅₁～R₁₆₀ is a single bond to L ₁₀₁,

More than 1 group of the group consisting of 2 or more adjacent groups among R ₁₅₁～R₁₅₄ other than the single bond bonded to L ₁₀₁ and the group consisting of 2 or more adjacent groups among R ₁₅₅～R₁₆₀

Is not bonded with each other and is not bonded with each other,

Group consisting of R ₁₆₁ and R ₁₆₂

Is not bonded with each other and is not bonded with each other,

R ₁₆₁ and R ₁₆₂ which do not form the above-mentioned substituted or unsubstituted monocyclic ring and do not form the above-mentioned substituted or unsubstituted condensed ring, and R ₁₅₁～R₁₆₀ which do not form the above-mentioned substituted or unsubstituted monocyclic ring and do not form the above-mentioned substituted or unsubstituted condensed ring, which are not a single bond to L ₁₀₁, are each independently

A hydrogen atom or a substituent R,

The substituents R are as defined in the general formula (H10),

Ar ₁₀₁ which is not a monovalent group having a structure represented by the above general formula (H50) is

A substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming carbon atoms. )

The position of the single bond with L ₁₀₁ in the above general formula (H50) is not particularly limited.

In one embodiment, 1 of R1 ₅₁～R₁₅₄ or 1 of R ₁₅₅～R₁₆₀ in the general formula (H50) above is a single bond to L ₁₀₁.

In one embodiment Ar ₁₀₁ is a monovalent group of the general formula (H50-R ₁₅₂), general formula (H50-R ₁₅₃), general formula (H50-R ₁₅₄), general formula (H50-R ₁₅₇), or general formula (H50-R ₁₅₈).

[ Chemical formula 178 ]

(In the above general formula (H50-R ₁₅₂), general formula (H50-R ₁₅₃), general formula (H50-R ₁₅₄), general formula (H50-R ₁₅₇) and general formula (H50-R ₁₅₈), X ₁₅₁、R₁₅₁～R₁₆₀ is the same as defined in the above general formula (H50),

* Bonded to L ₁₀₁. )

(Specific examples of the compounds represented by the general formula (H10))

The compound represented by the general formula (H10) may be exemplified by the following compounds. The compound represented by the general formula (H10) is not limited to these specific examples. In the following specific examples, D represents a deuterium atom.

[ Chemical formula 179 ]

[ Chemical formula 180 ]

[ Chemical formula 181 ]

[ Chemical formula 182 ]

[ Formula 183 ]

[ Chemical formula 184 ]

[ Chemical formula 185 ]

[ Chemical formula 186 ]

[ Chemical formula 187 ]

[ Chemical formula 188 ]

[ Chemical formula 189 ]

[ Chemical formula 190 ]

[ Chemical formula 191 ]

[ Chemical formula 192 ]

Specific examples of the above-mentioned groups are shown in the column [ definition ] of the present specification.

The organic EL element according to one embodiment of the present invention may be formed of a conventionally known material or element, as long as the effect of the present invention is not impaired, in addition to the above-described organic EL element having a cathode, an anode, and a light-emitting layer between the cathode and the anode, and the light-emitting layer contains the compound according to the first embodiment.

The organic EL element of the present embodiment preferably emits light having a maximum peak wavelength of 445nm to 460nm at the time of element driving.

The measurement of the maximum peak wavelength of light emitted from the organic EL element at the time of element driving was performed as follows. The organic EL element was applied with a voltage so that the current density was 10mA/cm ², and the spectral emission luminance spectrum at this time was measured by a spectral emission luminance meter CS-2000 (manufactured by Konica Minolta Co., ltd.). In the obtained spectrum of the spectral emission luminance, the peak wavelength of the emission spectrum having the largest emission intensity was measured and used as the maximum peak wavelength (unit: nm).

The content of the compound according to the first embodiment in the light-emitting layer is preferably 1% by mass or more and 20% by mass or less with respect to the entire light-emitting layer. The compound according to the first embodiment is preferably a dopant material.

In the organic EL element according to the present embodiment, when the light-emitting layer includes the compound represented by the general formula (H10) described above, the content of the compound represented by the general formula (H10) described above in the light-emitting layer is preferably 60 mass% or more with respect to the entire light-emitting layer, more preferably 70 mass% or more of the total mass of the light-emitting layer, and still more preferably 80 mass% or more of the total mass of the light-emitting layer. The compound represented by the above general formula (H10) is preferably a host material.

In the case where the light-emitting layer contains the compound represented by the general formula (H10) described above as the host material and the compound according to the first embodiment as the dopant material, the upper limit of the total content of the host material and the dopant material is 100 mass%.

Fourth embodiment

As the fourth embodiment, the organic EL element according to the present embodiment may be an organic EL element having 2 or more light-emitting layers.

The organic EL element of the fourth embodiment is different from the organic EL element of the third embodiment in that it has at least 2 or more light-emitting layers. Other points are the same as in the third embodiment.

In the description of the fourth embodiment, the same components as those of the third embodiment are denoted by the same reference numerals, names, and the like, and the description thereof is omitted or simplified. In the fourth embodiment, materials and compounds similar to those described in the first and third embodiments can be used as materials and compounds not mentioned specifically.

The structure of the organic EL element according to the present embodiment will be described.

The light-emitting layer of the organic EL element according to the present embodiment includes a first light-emitting layer and a second light-emitting layer. The first light emitting layer includes a first host material and a first dopant material. The second light emitting layer includes a second host material and a second dopant material. The first host material and the second host material are different from each other. The first dopant material and the second dopant material may be the same or different from each other.

The organic EL element according to the present embodiment includes at least 2 light-emitting layers (a first light-emitting layer and a second light-emitting layer). The first light-emitting layer according to the present embodiment has the same structure as the light-emitting layer of the organic EL element according to the third embodiment. Hereinafter, the differences from the first embodiment will be mainly described, and the repeated description will be omitted or simplified.

The organic EL element according to the present embodiment can have a long lifetime and can improve light emission efficiency by using a Triplet-Annihilation (sometimes referred to as tta).

TTA is a mechanism (mechanism) in which triplet excitons collide with triplet excitons to generate singlet excitons. As described in international publication No. 2010/134350, the TTA mechanism is sometimes referred to as a TTF mechanism.

The TTF phenomenon will be described. Holes injected from the anode and electrons injected from the cathode recombine within the light emitting layer to generate excitons. The spin state is a ratio of 25% for singlet excitons and 75% for triplet excitons, as conventionally known. In the previously known fluorescent element, 25% of the singlet excitons emit light when they relax to the ground state, and the remaining 75% of the triplet excitons do not emit light and return to the ground state through a heat deactivation process. Therefore, the theoretical limit of the internal quantum efficiency of the conventional fluorescent element is said to be 25%.

On the other hand, the behavior of triplet excitons generated inside an organic substance has been studied theoretically. According to s.m. bachlo et al (j.Phys.chem.a, 104,7711 (2000)), if it is assumed that higher excitons such as the penta state immediately return to the triplet state, when the density of the triplet excitons (hereinafter referred to as ³A^*) gradually increases, the triplet excitons collide with each other to cause a reaction shown in the following formula. Here, ¹ a represents a ground state, and ¹A^* represents a lowest excited singlet exciton.

³A^*+³A^*→(4/9)¹A+(1/9)¹A^*+(13/9)³A^*

That is, it is predicted that 1/5, that is, 20% of the triplet excitons, which are initially generated, are changed to singlet excitons, which are 5 ³A^*→4¹A+1A^*. Therefore, the singlet excitons contributing in the form of light are 40% obtained by adding 75% × (1/5) =15% to the 25% portion generated initially. At this time, the TTF-derived emission ratio (TTF ratio) of the total emission intensity was 15/40, that is, 37.5%. Further, when 75% of the triplet excitons generated at first collide with each other to generate singlet excitons (1 singlet exciton is generated from 2 triplet excitons), a very high internal quantum efficiency of 62.5% obtained by adding 75% × (1/2) =37.5% to 25% of the initially generated singlet excitons can be obtained. At this time, the TTF ratio was 37.5/62.5=60%.

In the organic EL element according to the present embodiment, from the viewpoint of exhibiting a TTF mechanism, the triplet energy T ₁ (H1) of the first host material and the triplet energy T ₁ (H2) of the second host material preferably satisfy the relationship of the following expression (expression 1), and more preferably satisfy the relationship of the following expression (expression 2).

T ₁(H2)>T₁ (H1.) (mathematical formula 1)

T ₁(H2)-T₁ (H1) >0.03eV. (formula 2)

In the organic EL element according to the present embodiment, it is considered that, by satisfying the relationship of the above expression (expression 1), triplet excitons generated by recombination of holes and electrons in the second light-emitting layer are not easily quenched even if excessive carriers exist at the interface between the second light-emitting layer and the organic layer directly contacting the second light-emitting layer. For example, in the case where the recombination region is locally present at the interface between the second light-emitting layer and the hole transport layer or the electron blocking layer, quenching by excessive electrons can be considered. On the other hand, if the recombination region is locally present at the interface between the second light-emitting layer and the electron transport layer or the hole blocking layer, quenching due to excessive holes can be considered.

The organic EL element according to the present embodiment includes the first light-emitting layer and the second light-emitting layer so as to satisfy the relationship of the above expression (expression 1), and thus, triplet excitons generated in the second light-emitting layer are not quenched by excessive carriers and move to the first light-emitting layer, and further, the reverse movement from the first light-emitting layer to the second light-emitting layer can be suppressed. As a result, the TTF mechanism is exhibited in the first light-emitting layer, and singlet excitons are efficiently generated, thereby improving the light-emitting efficiency.

In this way, the organic EL element includes the second light-emitting layer that mainly generates triplet excitons and the first light-emitting layer that mainly uses triplet excitons that have moved from the second light-emitting layer and that mainly exhibits a TTF mechanism as different regions, and the light-emitting efficiency is improved by providing a difference in triplet energy using a compound having triplet energy smaller than that of the second host material in the second light-emitting layer as the first host material in the first light-emitting layer.

The organic EL element according to the present embodiment can have a longer lifetime and can have an improved light-emitting efficiency by selecting a combination of host materials satisfying the relationship of the above expression (expression 1) and the first light-emitting layer containing the compound according to the first embodiment.

(Triplet energy T ₁)

The method for measuring the triplet energy T ₁ includes the following methods.

The compound to be measured was dissolved in EPA (diethyl ether: isopentane: ethanol=5:5:2 (volume ratio)) so that the concentration was 10 ^-5 mol/L or more and 10 ^-4 mol/L or less, and the solution was added to a quartz cuvette as a measurement sample. In this measurement sample, a phosphorescence spectrum (the vertical axis is the phosphorescence emission intensity, the horizontal axis is the wavelength) is measured at a low temperature (77 [ k ]), and the rising tangent line on the short wavelength side of the phosphorescence spectrum has a wavelength value λ _edge [ nm ] based on the intersection point of the tangent line and the horizontal axis, and the energy calculated according to the following equation (F1) is used as triplet energy T ₁.

Conversion formula (F1) T ₁[eV]＝1239.85/λ_edge

The rising tangent to 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 tangent line increases in slope as the curve rises (i.e., increases with the longitudinal axis). The tangent line drawn at the point where the value of the slope takes the maximum value (i.e., the tangent line at the inflection point) serves as the rising tangent line for the short wavelength side of the phosphorescence spectrum.

The maximum point of the peak intensity having 15% or less of the maximum peak intensity of the spectrum is not included in the maximum value on the shortest wavelength side, and the tangent line drawn at the point where the slope value closest to the maximum value on the shortest wavelength side takes the maximum value is taken as the rising tangent line on the short wavelength side of the phosphorescence spectrum.

As a method for measuring phosphorescence, a type F-4500 spectrophotometer manufactured by Hitachi, inc. may be used. The measuring apparatus is not limited to this, and the measuring apparatus may be configured to perform the measurement by combining the cooling apparatus with the low-temperature container, the excitation light source, and the light receiving apparatus.

(Emission wavelength of organic EL element)

The organic EL element according to the present embodiment preferably emits light having a maximum peak wavelength of 500nm or less, more preferably emits light having a wavelength of 445nm or more and 480nm or less, and still more preferably emits light having a wavelength of 445nm or more and 465nm or less when the element is driven. The measurement of the maximum peak wavelength of light emitted from the organic EL element at the time of element driving is as described above.

The measurement of the maximum peak wavelength of light emitted from the organic EL element at the time of element driving is performed as follows. The organic EL element was applied with a voltage so that the current density was 10mA/cm ², and the spectral emission luminance spectrum at this time was measured by a spectral emission luminance meter CS-2000 (manufactured by Konica Minolta Co., ltd.). In the obtained spectrum of the spectral emission luminance, the peak wavelength of the emission spectrum having the largest emission intensity was measured and used as the maximum peak wavelength (unit: nm).

(First light-emitting layer)

The first light emitting layer includes a first host material and a first dopant material. The first host material is a different compound from the second host material contained in the second light-emitting layer.

The first light-emitting layer according to the present embodiment has the same structure as the light-emitting layer according to the third embodiment. The first dopant material is preferably a compound according to the first embodiment (a compound represented by the above general formula (1)). The first host material is preferably a compound represented by the above general formula (H10).

In the organic EL element according to the fourth embodiment, the compound according to the first embodiment and the compound represented by the general formula (H10) can be used in combination in the first light-emitting layer of the organic EL element.

In the organic EL element according to the present embodiment, it is preferable that the first light-emitting layer emits light having a maximum peak wavelength of 500nm or less when the element is driven.

The maximum peak wavelength of light emitted from the light-emitting layer during element driving can be measured by the method described below.

Maximum peak wavelength λp of light emitted by the light-emitting layer at element driving

The maximum peak wavelength λp ₁ of light emitted from the first light-emitting layer at the time of element driving was calculated by manufacturing an organic EL element using the same material as the first light-emitting layer for the second light-emitting layer, and measuring the spectral emission luminance spectrum when a voltage was applied to the element so that the current density of the organic EL element became 10mA/cm ² by using a spectral emission luminance meter CS-2000 (manufactured by Konica Minolta corporation). From the obtained spectrum of the spectral emission luminance, the maximum peak wavelength λp ₁ (unit: nm) was calculated.

The maximum peak wavelength λp ₂ of light emitted from the second light-emitting layer at the time of element driving was calculated by manufacturing an organic EL element using the same material as that of the second light-emitting layer for the first light-emitting layer, and measuring the spectral emission luminance spectrum when a voltage was applied to the element so that the current density of the organic EL element became 10mA/cm ² by using a spectral emission luminance meter CS-2000 (manufactured by Konica Minolta corporation). From the obtained spectrum of the spectral emission luminance, the maximum peak wavelength λp ₂ (unit: nm) was calculated.

In the organic EL element according to the present embodiment, the triplet energy T ₁ (D1) of the first dopant material and the triplet energy T ₁ (H1) of the first host material preferably satisfy the relationship of the following expression (expression 4A).

T ₁(D1)>T₁ (H1.) (mathematical formula 4A)

In the organic EL element according to the present embodiment, the relationship between the first dopant material and the first host material satisfies the above expression (expression 4A), and thus triplet excitons generated in the second light-emitting layer are not transferred to the first dopant material having higher triplet energy but are transferred to molecules of the first host material when they move to the first light-emitting layer. In addition, triplet excitons generated by recombination of holes and electrons on the first host material do not move to the first dopant material having higher triplet energy. Triplet excitons generated by recombination on molecules of the first dopant material rapidly undergo energy transfer to molecules of the first host material.

The triplet excitons of the first host material do not move toward the first dopant material but efficiently collide with each other on the first host material through the TTF phenomenon, thereby generating singlet excitons.

In the organic EL element according to the present embodiment, the relationship between the singlet energy S ₁ (H1) of the first host material and the singlet energy S ₁ (D1) of the first dopant material preferably satisfies the following expression (expression 4).

S ₁(H1)>S₁ (D1), (mathematical formula 4)

In the organic EL element according to the present embodiment, the relationship of the first dopant material and the first host material satisfies the above equation (equation 4), and the singlet energy of the first dopant material is smaller than that of the first host material, so that the singlet excitons generated by the TTF phenomenon transfer energy from the first host material to the first dopant material, contributing to light emission (preferably fluorescence light emission) of the first dopant material.

(Singlet energy S ₁)

The method for measuring the singlet energy S ₁ using the solution (sometimes referred to as a solution method) includes the following method.

A toluene solution of 10 ^-5 mol/L or more and 10 ^-4 mol/L or less of a compound to be measured was prepared and put into a quartz cuvette, and the absorption spectrum (absorption intensity on the vertical axis and wavelength on the horizontal axis) of the sample was measured at room temperature (300K). For a falling tangent line on the long wavelength side of the absorption spectrum, the wavelength value λ _edge [ nm ] of the intersection of the tangent line and the horizontal axis is substituted into a conversion formula (F2) shown later to calculate the singlet energy.

Conversion formula (F2) S ₁ [ eV ] -1239.85/lambda edge

Examples of the absorption spectrum measuring apparatus include, but are not limited to, a spectrophotometer (apparatus name: U3310) manufactured by Hitachi Corp.

The tangent to the fall on the long wavelength side of the absorption spectrum is drawn as follows. The tangent at each point on the spectrum curve is considered when moving in the long wavelength direction on the spectrum curve from the maximum on the longest wavelength side among the maxima of the absorption spectrum. The slope of the tangent line repeatedly decreases and then increases as the curve falls (i.e., as the value of the vertical axis decreases). The tangent line drawn at the point where the value of the slope takes the minimum value on the longest wavelength side (excluding the case where the absorbance is 0.1 or less) is taken as the tangent line for the fall on the long wavelength side of the absorption spectrum.

The maximum point at which the absorbance value is 0.2 or less is not included in the maximum value on the longest wavelength side.

In the organic EL element according to the present embodiment, when the order of lamination 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, the electron mobility μe (H2) of the second host material and the electron mobility μe (H1) of the first host material preferably satisfy the relationship of the following expression (expression 3). The first host material and the second host material satisfy the following expression (expression 3), whereby the recombination capability of holes and electrons in the second light-emitting layer is improved.

Μe (H1) > μe (H2) (formula 3)

In the organic EL element according to the present embodiment, when the order of lamination 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, the relationship between the hole mobility μh (H2) of the second host material and the hole mobility μh (H1) of the first host material preferably satisfies the following equation (equation 31).

Μh (H2) > μh (H1) (formula 31)

In the organic EL element according to the present embodiment, when the order of lamination 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, the relation of the following expression (expression 32) is preferably satisfied also in the case where the hole mobility μh (H2) of the second host material, the electron mobility μe (H2) of the second host material, the hole mobility μh (H1) of the first host material, and the electron mobility μe (H1) of the first host material.

(Μe (H1)/μh (H1)) > (μe (H2)/μh (H2)). (equation 32)

The electron mobility can be measured by impedance measurement using a mobility evaluation element manufactured in accordance with the following procedure. The mobility evaluation element is manufactured, for example, in the following steps.

A compound Target, which is a measurement Target of electron mobility, is deposited on a glass substrate with an aluminum electrode (anode) so as to cover the aluminum electrode, thereby forming a measurement Target layer. The electron transport layer was formed by vapor deposition of the following compound ET-A on the layer to be measured. An electron injection layer is formed by vapor deposition of LiF on the film of the electron transport layer. Metal aluminum (A1) is deposited on the film of the electron injection layer to form a metal cathode.

The above-described element configuration for mobility evaluation is shown in the abbreviation below.

glass/Al(50)/Target(200)/ET-A(10)/LiF(1)/Al(50)

The numbers in brackets indicate film thickness (nm).

[ Chemical formula 193 ]

An element for evaluating the mobility of electron mobility is provided in an impedance measuring device, and impedance measurement is performed. Impedance measurement was performed by scanning the measurement frequency from 1Hz to 1 MHz. At this time, the element was applied with a dc voltage V at an ac amplitude of 0.1V. The modulus M is calculated from the measured impedance Z using the relationship of the following calculation formula (C1).

Calculation formula (C1) m=jωz

In the above calculation formula (C1), j is an imaginary unit whose square is-1, and ω is an angular frequency [ rad/s ].

In the bode plot having the imaginary part of the modulus M on the vertical axis and the frequency [ Hz ] on the horizontal axis, the electric time constant τ of the mobility evaluation element was obtained from the frequency fmax representing the peak by the following equation (C2).

Calculation formula (C2): τ=1/(2pi fmax)

Pi of the above calculation formula (C2) is a symbol indicating a circumference ratio.

The electron mobility μe is calculated from the relationship of the following expression (C3-1) using τ.

Calculation formula (C3-1): μe=d ²/(V tau)

D in the above formula (C3-1) is the total film thickness of the organic thin film constituting the element, and in the case of the element for evaluating the mobility of electron mobility, d=210 [ nm ].

The hole mobility can be measured by impedance measurement using a mobility evaluation element manufactured by the following procedure. The mobility evaluation element is manufactured, for example, in the following steps.

A hole injection layer was formed by vapor deposition of the following compound HA-2 on a glass substrate with an ITO transparent electrode (anode) so as to cover the transparent electrode. The following compound HT-A was vapor deposited on the film of the hole injection layer to form a hole transport layer. Then, a compound Target to be measured for hole mobility is vapor deposited to form a layer to be measured. Metal aluminum (Al) is deposited on the layer to be measured to form a metal cathode.

ITO(130)/HA-2(5)/HT-A(10)/Target(200)/Al(80)

The numbers in brackets indicate film thickness (nm).

[ Chemical formula 194 ]

The hole mobility evaluation element was set in an impedance measuring apparatus to measure impedance. Impedance measurement is performed in a scanning manner from 1Hz to 1 MHz. At this time, the element was applied with a dc voltage V at an ac amplitude of 0.1V. From the measured impedance Z, the modulus M is calculated using the relationship of the above-described calculation formula (C1).

In the bode plot having the imaginary part of the modulus M on the vertical axis and the frequency [ Hz ] on the horizontal axis, the electric time constant τ of the mobility evaluation element was obtained from the above-described calculation formula (C2) based on the frequency fmax representing the peak.

Using τ obtained by the above-described expression (C2), the hole mobility μh is calculated from the relationship of the following expression (C3-2).

Calculation formula (C3-2): μh=d ²/(V tau)

D in the above formula (C3-2) is the total film thickness of the organic thin film constituting the element, and in the case of the element for evaluating the hole mobility, d=215 [ nm ].

The electron mobility and the hole mobility in this specification are values at the square root E ^1/2＝500[V^1/2/cm¹ ^/2 of the electric field strength. The square root E ¹/² of the electric field strength can be calculated from the relationship of the following expression (C4).

Calculation formula (C4) E ^1/2＝V^1/2/d^1/2

For the impedance measurement, type 1260 of Solartron corporation was used as an impedance measuring device, and for the purpose of improving the accuracy, type 1296 dielectric constant measuring interface of Solartron corporation was used together.

In the organic EL element according to the present embodiment, the content of the first dopant material in the first light-emitting layer is preferably 0.5 mass% or more, more preferably more than 1.1 mass% of the total mass of the first light-emitting layer, still more preferably 1.2 mass% or more, and still more preferably 1.5 mass% or more of the total mass of the first light-emitting layer.

In the first light-emitting layer, the content of the first dopant material is preferably 10 mass% or less of the total mass of the first light-emitting layer, more preferably 7 mass% or less of the total mass of the first light-emitting layer, and still more preferably 5 mass% or less of the total mass of the first light-emitting layer.

In the organic EL element according to the present embodiment, the content of the first host material in the first light-emitting layer is preferably 60 mass% or more, more preferably 70 mass% or more, still more preferably 80 mass% or more, still more preferably 90 mass% or more, and still more preferably 95 mass% or more, of the total mass of the first light-emitting layer.

In the first light-emitting layer, the content of the first host material is preferably 99 mass% or less of the total mass of the first light-emitting layer.

When the first light-emitting layer contains the first host material and the first dopant material, the upper limit of the total content of the first host material and the first dopant material is 100 mass%.

The present embodiment does not exclude materials other than the first host material and the first dopant material from being included in the first light-emitting layer.

The first light-emitting layer may contain only 1 kind of the first host material, or may contain 2 or more kinds. The first light emitting layer may contain only 1 kind of the first dopant material, or may contain 2 or more kinds.

In the organic EL element according to the present embodiment, the film thickness of the first light-emitting layer is preferably 5nm or more, more preferably 15nm or more. If the film thickness of the first light-emitting layer is 5nm or more, triplet excitons moving from the second light-emitting layer to the first light-emitting layer are liable to be suppressed from returning to the second light-emitting layer again. In addition, if the film thickness of the first light-emitting layer is 5nm or more, triplet excitons can be sufficiently separated from the recombination portion in the second light-emitting layer.

In the organic EL element according to the present embodiment, the film thickness of the first light-emitting layer is preferably 20nm or less. If the film thickness of the first light-emitting layer is 20nm or less, the triplet exciton density in the first light-emitting layer can be increased, and the TTF phenomenon can be further easily caused.

In the organic EL element according to the present embodiment, the film thickness of the first light-emitting layer is preferably 5nm to 20 nm.

(Second light-emitting layer)

The second light emitting layer includes a second host material and a second dopant material. The second host material is a different compound from the first host material contained in the first light-emitting layer.

The second dopant material is preferably a compound that exhibits luminescence with a maximum peak wavelength of 500nm or less. The second dopant material is more preferably a compound that emits fluorescence having a maximum peak wavelength of 500nm or less.

The method for determining the maximum peak wavelength of the compound is as described above.

In the organic EL element according to the present embodiment, the second dopant material and the first dopant material are the same or different compounds.

In the organic EL element according to the present embodiment, the second light-emitting layer preferably does not contain a metal complex. In the organic EL element according to the present embodiment, the second light-emitting layer preferably does not contain a boron-containing complex.

In the organic EL element according to the present embodiment, the second light-emitting layer preferably does not contain a phosphorescent material (dopant material).

In addition, the second light-emitting layer preferably does not contain a heavy metal complex and a phosphorescent rare earth metal complex.

In the light emission spectrum of the second dopant material, when a peak at which the light emission intensity reaches the maximum is set as a maximum peak and the height of the maximum peak is set to 1, the height of the other peaks appearing in the light emission spectrum is preferably less than 0.6. The peak in the emission spectrum was set to the maximum value.

In addition, in the light emission spectrum of the second luminescent compound, the number of peaks is preferably less than 3.

In the organic EL element according to the present embodiment, it is preferable that the second light-emitting layer emits light having a maximum peak wavelength of 500nm or less when the element is driven.

(Second host material)

Examples of the second host material include:

1) Anthracene derivative, phenanthrene derivative, pyrene derivative, benzanthracene derivative, fluorene derivative, fluoranthene derivative or Condensed aromatic compounds such as derivatives,

2) Heterocyclic compounds such as carbazole derivatives, dibenzofuran derivatives, dibenzothiophene derivatives, and benzoxanthene derivatives.

The second host material is preferably a fused aromatic compound,

More preferably a pyrene derivative (a compound represented by the general formula (H100) described below).

In addition, the second host material is also preferably

A benzanthracene derivative (a compound represented by the general formula (H1X) described below) or a benzanthrene derivative (a compound represented by the general formula (H14X) described below).

In the case where the second host material is a pyrene derivative, the second host material is preferably a compound represented by the following general formula (H100).

(Compound of the general formula (H100))

[ Chemical formula 195 ]

(In the above-mentioned general formula (H100),

R ₁₀₁～R₁₁₀ are each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by Si (R ₉₀₁)(R₉₀₂)(R₉₀₃),

A group represented by-O- (R ₉₀₄),

A group represented by S- (R ₉₀₅),

Substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C (=O) R ₈₀₁ a group,

A group represented by COOR ₈₀₂,

Halogen atom,

Cyano group,

Nitro group,

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

A group represented by the above general formula (H110),

Wherein at least 1 of R ₁₀₁～R₁₁₀ is a group represented by the above general formula (H110),

When there are a plurality of groups represented by the above general formula (H110), the plurality of groups represented by the above general formula (H110) are the same or different from each other,

L ₁₀₁ is

A single bond,

Substituted or unsubstituted arylene group having 6 to 50 ring members, or

Ar ₁₀₁ is

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

Mx is 0,1, 2, 3, 4 or 5,

In the case where there are 2 or more L ₁₀₁, 2 or more L ₁₀₁ are the same or different from each other,

In the case where Ar ₁₀₁ is present in an amount of 2 or more, ar ₁₀₁ of 2 or more are the same or different from each other,

The bonding position to the pyrene ring in the general formula (H100) is represented by the following formula (H110). )

(In the second host material, R ₉₀₁、R₉₀₂、R₉₀₃、R₉₀₄、R₉₀₅、R₉₀₆、R₉₀₇、R₈₀₁ and R ₈₀₂ are each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

Where there are plural R ₉₀₇, plural R ₉₀₇ are the same or different from each other,

Where there are plural R ₈₀₁, plural R ₈₀₁ are the same or different from each other,

In the case where there are plural R ₈₀₂, plural R ₈₀₂ are the same or different from each other. )

In the organic EL element according to the present embodiment, the group represented by the above general formula (H110) is preferably a group represented by the following general formula (H111).

[ Chemical formula 196 ]

(In the above general formula (H111),

X ₁₀ is C (R ₁₂₃)(R₁₂₄), an oxygen atom, a sulfur atom, or NR ₁₂₅,

L ₁₁₁ and L ₁₁₂ are each independently

A single bond,

Substituted or unsubstituted arylene group having 6 to 50 ring members, or

Ma is 0, 1,2,3 or 4,

Mb is 0, 1,2,3 or 4,

Ma+mb is 0, 1, 2,3 or 4,

Ar ₁₀₁ has the same meaning as Ar ₁₀₁ in the above general formula (H110),

R ₁₂₁、R₁₂₂、R₁₂₃、R₁₂₄ and R ₁₂₅ are each independently of the other

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by Si (R ₉₀₁)(R₉₀₂)(R₉₀₃),

A group represented by-O- (R ₉₀₄),

A group represented by S- (R ₉₀₅),

Substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C (=O) R ₈₀₁ a group,

A group represented by COOR ₈₀₂,

Halogen atom,

Cyano group,

Nitro group,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

The number of the mc is 3 and the number of the m,

3R ₁₂₁ are identical or different from each other,

The md is set to be 3 and the number of the components is set to be 3,

3R ₁₂₂ are identical or different from each other. )

Of the positions of carbon atoms 1 to 8 in the ring structure of the following general formula (H111 a) in the group of the general formula (H111), L ₁₁₁ is bonded to any one position of 1 to 4, R ₁₂₁ is bonded to the remaining 3 positions of 1 to 4, L ₁₁₂ is bonded to any one position of 5 to 8, and R ₁₂₂ is bonded to the remaining 3 positions of 5 to 8.

[ Chemical formula 197 ]

For example, in the group represented by the above general formula (H111), when L ₁₁₁ is bonded to the position of the carbon atom of x2 in the ring structure represented by the above general formula (H111 a) and L ₁₁₂ is bonded to the position of the carbon atom of x 7 in the ring structure represented by the above general formula (H111 a), the group represented by the above general formula (H111) is represented by the following general formula (H111 b).

[ Chemical formula 198 ]

(In the above general formula (H111 b),

X ₁₀、L₁₁₁、L₁₁₂、ma、mb、Ar₁₀₁、R₁₂₁、R₁₂₂、R₁₂₃、R₁₂₄ and R ₁₂₅ are each independently the same as X ₁₀、L₁₁₁、L₁₁₂、ma、mb、Ar₁₀₁、R₁₂₁、R₁₂₂、R₁₂₃、R₁₂₄ and R ₁₂₅ in the above general formula (H111),

A plurality of R ₁₂₁ are the same or different from each other,

The plurality of R ₁₂₂ are the same or different from each other. )

In the organic EL element according to the present embodiment, the group represented by the general formula (H111) is preferably a group represented by the general formula (H111 b).

In the organic EL element according to the present embodiment, preferably,

Ma is 0, 1 or 2,

Mb is 0, 1 or 2.

In the organic EL element according to the present embodiment, preferably,

The ma is either 0 or 1,

Mb is 0 or 1.

In the organic EL element according to the present embodiment, ar ₁₀₁ is preferably a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

In the organic EL element according to the present embodiment,

Ar ₁₀₁ is preferably

Substituted or unsubstituted phenyl,

Substituted or unsubstituted naphthyl,

Substituted or unsubstituted biphenyl,

Substituted or unsubstituted terphenyl,

Substituted or unsubstituted pyrenyl,

Substituted or unsubstituted phenanthryl, or

Substituted or unsubstituted fluorenyl.

In the organic EL element according to the present embodiment,

Ar101 is also preferably a group represented by the following general formula (H120), general formula (H130) or general formula (H140).

[ Chemical formula 199 ]

(In the above general formula (H120), general formula (H130) and general formula (H140),

R ₁₁₁～R₁₂₀ are each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by Si (R ₉₀₁)(R₉₀₂)(R₉₀₃),

A group represented by-O- (R ₉₀₄),

A group represented by S- (R ₉₀₅),

A group represented by-N (R ₉₀₆₎(R₉₀₇),

Substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C (=O) R ₈₀₁ a group,

A group represented by COOR ₈₀₂,

Halogen atom,

Cyano group,

Nitro group,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

The bonding position to L ₁₀₁ in the general formula (H110) or to L ₁₁₂ in the general formula (H111) or (H111 b) is represented by the general formula (H120), the general formula (H130) and the general formula (H140). )

In the organic EL element according to the present embodiment,

The second host material is preferably represented by the following general formula (H101).

[ Chemical formula 200 ]

(In the above-mentioned general formula (H101),

R ₁₀₁～R₁₂₀ are each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by Si (R ₉₀₁)(R₉₀₂)(R₉₀₃),

A group represented by-O- (R ₉₀₄),

A group represented by S- (R ₉₀₅),

Substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C (=O) R ₈₀₁ a group,

A group represented by COOR ₈₀₂,

Halogen atom,

Cyano group,

Nitro group,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

Wherein 1 of R ₁₀₁～R₁₁₀ represents a bonding position with L ₁₀₁, 1 of R ₁₁₁～R₁₂₀ represents a bonding position with L ₁₀₁,

L ₁₀₁ is

A single bond,

Substituted or unsubstituted arylene group having 6 to 50 ring members, or

Mx is 0,1, 2, 3, 4 or 5,

In the case where there are 2 or more L ₁₀₁, 2 or more L ₁₀₁ are the same or different from each other. )

In the organic EL element according to the present embodiment,

L ₁₀₁ is preferably

Single bond, or

Substituted or unsubstituted arylene groups having 6 to 50 ring members.

In the organic EL element according to the present embodiment,

The second host material is preferably represented by the following general formula (H102).

[ Chemical formula 201 ]

(In the above-mentioned general formula (H102),

R ₁₀₁～R₁₂₀ is each independently the same as R ₁₀₁～R₁₂₀ in the above general formula (H101),

Wherein 1 of R ₁₀₁～R₁₁₀ represents a bonding position with L ₁₁₁, 1 of R ₁₁₁～R₁₂₀ represents a bonding position with L ₁₁₂,

L ₁₁₁ and L ₁₁₂ are each independently

A single bond,

Substituted or unsubstituted arylene group having 6 to 50 ring members, or

Ma is 0, 1,2,3 or 4,

Mb is 0, 1,2,3 or 4,

Ma+mb is 0, 1, 2,3 or 4,

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by Si (R ₉₀₁)(R₉₀₂)(R₉₀₃),

A group represented by-O- (R ₉₀₄),

A group represented by S- (R ₉₀₅),

Substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C (=O) R ₈₀₁ a group,

A group represented by COOR ₈₀₂,

Halogen atom,

Cyano group,

Nitro group,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

The number of the mc is 3 and the number of the m,

3R ₁₂₁ are identical or different from each other,

The md is set to be 3 and the number of the components is set to be 3,

3R ₁₂₂ are identical or different from each other. )

Among the compounds represented by the above general formula (H102), it is preferable that,

Ma is 0, 1 or 2,

Mb is 0, 1 or 2.

The ma is either 0 or 1,

Mb is 0 or 1.

In the organic EL element according to the present embodiment, preferably,

More than 2 of R ₁₀₁～R₁₁₀ are groups represented by the above general formula (H110).

In the organic EL element according to the present embodiment, preferably,

More than 2 of R ₁₀₁～R₁₁₀ are groups represented by the general formula (H110) and Ar ₁₀₁ is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

In the organic EL element according to the present embodiment, preferably,

Ar ₁₀₁ is not substituted or unsubstituted pyrenyl,

L ₁₀₁ is not a substituted or unsubstituted pyrenylene group,

R ₁₀₁～R₁₁₀ which is a group other than the group represented by the general formula (H110) is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and is not a substituted or unsubstituted pyrenyl group.

In the organic EL element according to the present embodiment, preferably,

R ₁₀₁～R₁₁₀ other than the group represented by the above general formula (H110) is each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

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

In the organic EL element according to the present embodiment, preferably,

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

Substituted or unsubstituted cycloalkyl having 3 to 50 ring-forming carbon atoms.

In the organic EL element according to the present embodiment, R ₁₀₁～R₁₁₀ which is not a group represented by the above general formula (H110) is preferably a hydrogen atom.

In the compounds represented by the above general formula (H100), the groups described as "substituted or unsubstituted" are preferably "unsubstituted" groups.

The compound represented by the general formula (H100) can be produced by a known method.

(Specific examples of the compounds represented by the general formula (H100))

Specific examples of the compound represented by the general formula (H100) include the following compounds. The compound represented by the general formula (H100) is not limited to the following specific examples.

[ Chemical formula 202 ]

[ Chemical formula 203 ]

[ Chemical formula 204 ]

[ Chemical formula 205 ]

[ Chemical formula 206 ]

[ Chemical formula 207 ]

[ Chemical formula 208 ]

[ Chemical formula 209 ]

[ Chemical formula 210 ]

[ Chemical formula 211 ]

[ Chemical formula 212 ]

[ Chemical formula 213 ]

[ Chemical formula 214 ]

[ Chemical formula 215 ]

[ Chemical formula 216 ]

[ Chemical formula 217 ]

[ Formula 218 ]

[ Chemical formula 219 ]

[ Chemical formula 220 ]

[ Chemical formula 221 ]

[ Chemical formula 222 ]

[ Chemical formula 223 ]

In the case where the second host material is a benzanthracene derivative, the second host material is preferably a compound represented by the following general formula (H1X).

(Compound represented by the general formula (H1X))

[ Chemical formula 224 ]

(In the above general formula (H1X),

R ₁₀₁～R₁₁₂ are each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by Si (R ₉₀₁)(R₉₀₂)(R₉₀₃),

A group represented by-O- (R ₉₀₄),

A group represented by S- (R ₉₀₅),

Substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C (=O) R ₈₀₁ a group,

A group represented by COOR ₈₀₂,

Halogen atom,

Cyano group,

Nitro group,

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

A group represented by the above general formula (H11X),

Wherein at least 1 of R ₁₀₁～R₁₁₂ is a group represented by the above general formula (H11X),

When there are a plurality of groups represented by the above general formula (H11X), the plurality of groups represented by the above general formula (H11X) are the same or different from each other,

L ₁₀₁ is

A single bond,

Substituted or unsubstituted arylene group having 6 to 50 ring members, or

Ar ₁₀₁ is

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

Mx is 1,2, 3, 4 or 5,

The expression "X" in the above general formula (H11X) represents a bonding position to the benzo [ a ] anthracycline in the above general formula (H1X). )

In the organic EL element according to the present embodiment, the group represented by the above general formula (H11X) is preferably a group represented by the following general formula (H111X).

[ Chemical formula 225 ]

(In the above general formula (H111X),

X ₁₀ is C (R ₃₄₃)(R₃₄₄), an oxygen atom, a sulfur atom, or NR ₃₄₅,

L ₁₁₁ and L ₁₁₂ are each independently

A single bond,

Substituted or unsubstituted arylene group having 6 to 50 ring members, or

Ma is 1, 2, 3 or 4,

Mb is 1, 2, 3 or 4,

Ma+mb is 2, 3 or 4,

Ar ₁₀₁ has the same meaning as Ar ₁₀₁ in the above general formula (H11X),

R ₃₄₁、R₃₄₂、R₃₄₃、R₃₄₄ and R ₃₄₅ are each independently of the other

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by Si (R ₉₀₁)(R₉₀₂)(R₉₀₃),

A group represented by-O- (R ₉₀₄),

A group represented by S- (R ₉₀₅),

Substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C (=O) R ₈₀₁ a group,

A group represented by COOR ₈₀₂,

Halogen atom,

Cyano group,

Nitro group,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

The number of the mc is 3 and the number of the m,

3R ₃₄₁ are identical or different from each other,

The md is set to be 3 and the number of the components is set to be 3,

3R ₃₄₂ are identical or different from each other. )

Of the positions of carbon atoms 1 to 8 in the ring structure of the following general formula (H111 aX) in the group of the general formula (H111X), L ₁₁₁ is bonded to any one of positions 1 to 4, R ₃₄₁ is bonded to the remaining 3 positions 1 to 4, L ₁₁₂ is bonded to any one of positions 5 to 8, and R ₃₄₂ is bonded to the remaining 3 positions 5 to 8.

[ Formula 226 ]

For example, in the group represented by the above general formula (H111X), in the case where L ₁₁₁ is bonded to the position of the carbon atom of X2 in the ring structure represented by the above general formula (H111 aX) and L ₁₁₂ is bonded to the position of the carbon atom of X7 in the ring structure represented by the above general formula (H111 aX), the group represented by the above general formula (H111X) is represented by the following general formula (H111 bX).

[ Chemical formula 227 ]

(In the above general formula (H111 bX),

X ₁₀、L₁₁₁、L₁₁₂、ma、mb、Ar₁₀₁、R₃₄₁、R₃₄₂、R₃₄₃、R₃₄₄ and R ₃₄₅ are each independently the same as X ₁₀、L₁₁₁、L₁₁₂、ma、mb、Ar₁₀₁、R₃₄₁、R₃₄₂、R₃₄₃、R₃₄₄ and R ₃₄₅ in the above general formula (H111X),

A plurality of R ₃₄₁ are the same or different from each other,

The plurality of R ₃₄₂ are the same or different from each other. )

In the organic EL element according to the present embodiment, the group represented by the general formula (H111X) is preferably a group represented by the general formula (H111 bX).

In the compounds of the above formula (H1X), preferably, ma is 1 or 2 and mb is 1 or 2.

Among the compounds represented by the above general formula (H1X), preferably, ma is 1 and mb is 1.

In the compound represented by the general formula (H1X), ar ₁₀₁ is preferably a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

Among the compounds represented by the above general formula (H1X), ar ₁₀₁ is preferably

Substituted or unsubstituted phenyl,

Substituted or unsubstituted naphthyl,

Substituted or unsubstituted biphenyl,

Substituted or unsubstituted terphenyl,

Substituted or unsubstituted benzo [ a ] anthracenyl,

Substituted or unsubstituted pyrenyl,

Substituted or unsubstituted phenanthryl, or

Substituted or unsubstituted fluorenyl.

The compound represented by the above general formula (H1X) is also preferably represented by the following general formula (H101X).

[ Chemical formula 228 ]

(In the above general formula (H101X),

1 Of R ₁₁₁ and R ₁₁₂ represents a bonding position with L ₁₀₁, 1 of R ₃₃₃ and R ₃₃₄ represents a bonding position with L ₁₀₁,

R ₁₀₁～R₁₁₀、R₃₂₁～R₃₃₀, R ₁₁₁ or R ₁₁₂ which are not in bonding position with L ₁₀₁, and R ₃₃₃ or R ₃₃₄ which are not in bonding position with L ₁₀₁ are each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by Si (R ₉₀₁)(R₉₀₂)(R₉₀₃),

A group represented by-O- (R ₉₀₄),

A group represented by S- (R ₉₀₅),

Substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C (=O) R ₈₀₁ a group,

A group represented by COOR ₈₀₂,

Halogen atom,

Cyano group,

Nitro group,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

L ₁₀₁ is

A single bond,

Substituted or unsubstituted arylene group having 6 to 50 ring members, or

Mx is 1,2, 3, 4 or 5,

In the compound represented by the general formula (H1X), L ₁₀₁ is preferably a single bond or a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms.

The compound represented by the above general formula (H1X) is also preferably represented by the following general formula (H102X).

[ Chemical formula 229 ]

(In the above general formula (H102X),

1 Of R ₁₁₁ and R ₁₁₂ represents a bonding position with L ₁₁₁, 1 of R ₃₃₃ and R ₃₃₄ represents a bonding position with L ₁₁₂,

R ₁₀₁～R₁₁₀、R₃₂₁～R₃₃₀, R ₁₁₁ or R ₁₁₂ which are not in bonding position with L ₁₁₁, and R ₃₃₃ or R ₃₃₄ which are not in bonding position with L ₁₁₂ are each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by Si (R ₉₀₁)(R₉₀₂)(R₉₀₃),

A group represented by-O- (R ₉₀₄),

A group represented by S- (R ₉₀₅),

Substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C (=O) R ₈₀₁ a group,

A group represented by COOR ₈₀₂,

Halogen atom,

Cyano group,

Nitro group,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

L ₁₁₁ and L ₁₁₂ are each independently

A single bond,

Substituted or unsubstituted arylene group having 6 to 50 ring members, or

Ma is 1, 2, 3 or 4,

Mb is 1, 2, 3 or 4,

Ma+mb is 2, 3, 4 or 5,

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by Si (R ₉₀₁)(R₉₀₂)(R₉₀₃),

A group represented by-O- (R ₉₀₄),

A group represented by S- (R ₉₀₅),

Substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C (=O) R ₈₀₁ a group,

A group represented by COOR ₈₀₂,

Halogen atom,

Cyano group,

Nitro group,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

The number of the mc is 3 and the number of the m,

3R ₃₄₁ are identical or different from each other,

The md is set to be 3 and the number of the components is set to be 3,

3R ₃₄₂ are identical or different from each other. )

In the compound represented by the above general formula (H1X), preferably, ma in the above general formula (H102X) is 1 or 2, and mb is 1 or 2.

In the compound represented by the above general formula (H1X), preferably, ma in the above general formula (H102X) is 1 and mb is 1.

Among the compounds represented by the above general formula (H1X), the group represented by the above general formula (H11X) is also preferably a group represented by the following general formula (H11 AX) or a group represented by the following general formula (H11 BX).

[ Formula 230 ]

(In the above general formula (H11 AX) and the above general formula (H11 BX),

R ₁₂₁～R₁₂₉、R₃₃₀ and R ₃₃₁ are each independently of the other

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by Si (R ₉₀₁)(R₉₀₂)(R₉₀₃),

A group represented by-O- (R ₉₀₄),

A group represented by S- (R ₉₀₅),

Substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C (=O) R ₈₀₁ a group,

A group represented by COOR ₈₀₂,

Halogen atom,

Cyano group,

Nitro group,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

When there are a plurality of groups represented by the above general formula (H11 AX), the plurality of groups represented by the above general formula (H11 AX) are the same or different from each other,

When there are a plurality of groups represented by the above general formula (H11 BX), the plurality of groups represented by the above general formula (H11 BX) are the same or different from each other,

L ₁₃₁ and L ₁₃₂ are each independently

A single bond,

Substituted or unsubstituted arylene group having 6 to 50 ring members, or

Each of the above general formula (H11 AX) and the above general formula (H11 BX) represents a bonding position to the benzo [ a ] anthracycline of the above general formula (H1X). )

The compound represented by the above general formula (H1X) is also preferably represented by the following general formula (H103X).

[ Chemical formula 231 ]

(In the above general formula (H103X),

R ₁₀₁～R₁₁₀ and R ₁₁₂ are each as defined for R ₁₀₁～R₁₁₀ and R ₁₁₂ in the above general formula (H1X),

R ₁₂₁～R₁₂₉、R₃₃₀ and R ₃₃₁, and L ₁₃₁ and L ₁₃₂ are each as defined for R ₁₂₁～R₁₂₉、R₃₃₀ and R ₃₃₁, and L ₁₃₁ and L ₁₃₂ in the above general formula (H11 BX). )

In the compound represented by the general formula (H1X), L ₁₃₁ is also preferably a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms.

In the compound represented by the general formula (H1X), L ₁₃₂ is also preferably a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms.

Among the compounds represented by the above general formula (H1X), it is also preferable that 2 or more of R ₁₀₁～R₁₁₂ are groups represented by the above general formula (H11X).

In the compound represented by the general formula (H1X), preferably, 2 or more of R ₁₀₁～R₁₁₂ are groups represented by the general formula (H11X), and Ar ₁₀₁ in the general formula (H11X) is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

Among the compounds represented by the above general formula (H1X), it is also preferable,

Ar ₁₀₁ is not substituted or unsubstituted benzo [ a ] anthracenyl,

L ₁₀₁ is not substituted or unsubstituted benzo [ a ] anthracenyl,

R ₁₀₁～R₁₁₀ which is a group other than the group represented by the general formula (H11X) is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and is not a substituted or unsubstituted benzo [ a ] anthracenyl group.

In the compound represented by the general formula (H1X), R ₁₀₁～R₁₁₂ which is not a group represented by the general formula (H11X) is each independently preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming carbon atoms.

In the compound represented by the general formula (H1X), R ₁₀₁～R₁₁₂ which is not a group represented by the general formula (H11X) is preferably a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms.

In the compound represented by the general formula (H1X), R ₁₀₁～R₁₁₂ which is not a group represented by the general formula (H11X) is preferably a hydrogen atom.

The compound represented by the general formula (H1X) can be produced by a known method.

(Specific examples of the compounds represented by the general formula (H1X))

Specific examples of the compound represented by the general formula (H1X) include the following compounds. The compound represented by the general formula (H1X) is not limited to the following specific examples.

[ Chemical formula 232 ]

[ Chemical formula 233 ]

[ Chemical formula 234 ]

[ Chemical formula 235 ]

In the case where the second host material is a benzoxanthene derivative, the second host material is preferably a compound represented by the following general formula (H14X).

(Compound of the general formula (H14X))

[ Chemical formula 236 ]

(In the above general formula (H14X),

R ₁₄₀₁～R₁₄₁₀ are each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by Si (R ₉₀₁)(R₉₀₂)(R₉₀₃),

A group represented by-O- (R ₉₀₄),

A group represented by S- (R ₉₀₅),

Substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C (=O) R ₈₀₁ a group,

A group represented by COOR ₈₀₂,

Halogen atom,

Cyano group,

Nitro group,

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

A group represented by the above general formula (H141),

Wherein at least 1 of R ₁₄₀₁～R₁₄₁₀ is a group represented by the above general formula (H141),

When there are a plurality of groups represented by the above general formula (H141), the plurality of groups represented by the above general formula (H141) may be the same or different from each other,

L ₁₄₀₁ is

A single bond,

Substituted or unsubstituted arylene group having 6 to 50 ring members, or

Ar ₁₄₀₁ is

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

Mx4 is 0, 1, 2,3, 4 or 5,

In the case where there are 2 or more L ₁₄₀₁, 2 or more L ₁₄₀₁ are the same or different from each other,

When there are 2 or more Ar ₁₄₀₁, 2 or more Ar ₁₄₀₁ are the same or different from each other, and the bond position to the ring represented by the general formula (H14X) is represented by the general formula (H141). )

The compound represented by the general formula (H14X) can be produced by a known method.

(Specific examples of the compounds represented by the general formula (H14X))

Specific examples of the compound represented by the general formula (H14X) include the following compounds. The compound represented by the general formula (H14X) is not limited to the following specific examples.

[ Formula 237 ]

[ Chemical formula 238 ]

(Second dopant material)

Examples of the second dopant material include

A compound according to the first embodiment, a pyrene derivative, a styrylamine derivative,Derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, aromatic amine derivatives, and naphthacene derivatives, etc.

The second dopant material is preferably

A compound according to the first embodiment,

A compound represented by the following general formula (5) or

A compound represented by the following general formula (6).

(Compound represented by the general formula (5))

[ Formula 239 ]

(In the above-mentioned general formula (5),

More than 1 group of groups consisting of 2 adjacent more than 2 of R ₅₀₁～-R₅₀₇ and R ₅₁₁～R₅₁₇

Is not bonded with each other and is not bonded with each other,

R ₅₀₁～R₅₀₇ and R ₅₁₁～R₅₁₇ which do not form the above-mentioned substituted or unsubstituted monocyclic ring and which do not form the above-mentioned substituted or unsubstituted condensed ring are each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by Si (R ₉₀₁)(R₉₀₂)(R₉₀₃),

A group represented by-O- (R ₉₀₄),

A group represented by S- (R ₉₀₅),

A group represented by-N (R ₉₀₆)(R₉₀₇),

Halogen atom,

Cyano group,

Nitro group,

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

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

R ₅₂₁ and R ₅₂₂ are each independently of the other

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by Si (R ₉₀₁)(R₉₀₂)(R₉₀₃),

A group represented by-O- (R ₉₀₄),

A group represented by S- (R ₉₀₅),

A group represented by-N (R ₉₀₆}(R₉₀₇),

Halogen atom,

Cyano group,

Nitro group,

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

In the second dopant material, R ₉₀₁、R₉₀₂、R₉₀₃、R₉₀₄、R₉₀₅、R₉₀₆ and R ₉₀₇ are each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

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

In the case where there are plural R ₉₀₇, plural R ₉₀₇ are the same or different from each other.

"1 Group among the adjacent 2 or more groups among R ₅₀₁～R₅₀₇ and R ₅₁₁～R₅₁₇" is, for example, a group of R ₅₀₁ and R ₅₀₂, a group of R ₅₀₂ and R ₅₀₃, a group of R ₅₀₃ and R ₅₀₄, a group of R ₅₀₅ and R ₅₀₆, a group of R ₅₀₆ and R ₅₀₇, a group of R ₅₀₁ and R ₅₀₂ and R ₅₀₃, or the like.

In one embodiment, at least 1, preferably 2 of R ₅₀₁～R₅₀₇ and R ₅₁₁～R₅₁₇ are groups represented by-N (R ₉₀₆)(R₉₀₇).

In one embodiment, each of R ₅₀₁～R₅₀₇ and R ₅₁₁～R₅₁₇ is independently

A hydrogen atom,

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

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

In one embodiment, the compound represented by the above general formula (5) is a compound represented by the following general formula (52).

[ Chemical formula 240 ]

(In the above-mentioned general formula (52),

More than 1 group of groups consisting of 2 adjacent more than 2 of R ₅₃₁～R₅₃₄ and R ₅₄₁～R₅₄₄

Is not bonded with each other and is not bonded with each other,

R ₅₃₁～R₅₃₄、R₅₄₁～R₅₄₄, which does not form the above-mentioned substituted or unsubstituted monocyclic ring and does not form the above-mentioned substituted or unsubstituted condensed ring, and R ₅₅₁ and R ₅₅₂ are each independently

A hydrogen atom,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

R ₅₆₁～R₅₆₄ are each independently

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

In one embodiment, the compound represented by the above general formula (5) is a compound represented by the following general formula (53).

[ Chemical formula 241 ]

(In the above general formula (53), R ₅₅₁、R₅₅₂ and R ₅₆₁～R₅₆₄ each independently have the same meaning as R ₅₅₁、R₅₅₂ and R ₅₆₁～R₅₆₄ in the above general formula (52))

In one embodiment, R ₅₆₁～R₅₆₄ in the general formula (52) and the general formula (53) is independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms (preferably a phenyl group).

In one embodiment, R ₅₂₁ and R ₅₂₂ in the above formula (5), and R ₅₅₁ and R ₅₅₂ in the above formula (52) and formula (53) are hydrogen atoms.

In one embodiment, the substituents expressed as "substituted or unsubstituted" in the above general formula (5), general formula (52) and general formula (53) are

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

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

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

The compound represented by the above general formula (5) can be produced by a known method.

(Specific example of the compound represented by the general formula (5))

Specific examples of the compound represented by the above general formula (5) include the following compounds. The compound represented by the general formula (5) is not limited to the following specific examples.

[ Chemical formula 242 ]

[ Chemical formula 243 ]

[ 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 ]

[ Chemical formula 253 ]

[ Chemical formula 254 ]

[ Chemical formula 255 ]

[ Chemical formula 256 ]

(Compound represented by the general formula (6))

[ Chemical formula 257 ]

(In the above-mentioned general formula (6),

The a, b and c rings are each independently

A substituted or unsubstituted heterocyclic ring having 5 to 50 ring members,

R ₆₀₁ and R ₆₀₂ each independently form a substituted or unsubstituted heterocycle, or are bonded to the above-mentioned a ring, b ring or c ring to form a substituted or unsubstituted heterocycle,

R ₆₀₁ and R ₆₀₂ which do not form the above-mentioned substituted or unsubstituted heterocycle are each independently

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

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

The a ring, the b ring and the c ring are rings condensed with a condensed 2-ring structure in the center of the above general formula (6) composed of a boron atom and 2 nitrogen atoms (a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming carbon atoms).

The "aromatic hydrocarbon ring" of the a ring, the b ring and the c 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 a-ring contains 3 carbon atoms on the condensed 2-ring structure in the center of the above general formula (6) as ring-forming atoms.

The "aromatic hydrocarbon ring" of the b ring and the c ring contains 2 carbon atoms on the condensed 2-ring structure in the center of the above general formula (6) as ring-forming atoms.

Specific examples of the "substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms" include compounds obtained by introducing a hydrogen atom into the "aryl group" described in the specific example group G1.

The "heterocycle" of the a ring, the b ring and the c ring has the same structure as the compound obtained by introducing a hydrogen atom into the above-mentioned "heterocyclic group".

The "heterocycle" of the a ring contains 3 carbon atoms on the condensed 2-ring structure in the center of the above general formula (6) as ring-forming atoms. The "heterocycle" of the b ring and the c ring contains 2 carbon atoms on the condensed 2-ring structure in the center of the above general formula (6) as ring-forming atoms. Specific examples of the "substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms" include compounds obtained by introducing a hydrogen atom into the "heterocyclic group" described in the specific example group G2.

R ₆₀₁ and R ₆₀₂ each independently can be bonded to the a-, b-or c-ring to form a substituted or unsubstituted heterocycle. The heterocycle in this case contains a nitrogen atom on the condensed 2-ring structure in the center of the above general formula (6). The heterocyclic ring in this case may contain a heteroatom other than a nitrogen atom. R ₆₀₁ and R ₆₀₂ are bonded to the a-, b-or c-ring, specifically, the atom constituting the a-, b-or c-ring is bonded to the atom constituting R ₆₀₁ and R ₆₀₂. For example, R ₆₀₁ may be bonded to the a ring to form a nitrogen-containing heterocyclic ring in which a ring including R ₆₀₁ is fused to the 2 ring of the a ring (or 3 rings or more are fused). Specific examples of the nitrogen-containing heterocycle include compounds corresponding to a heterocyclic group condensed at least 2 rings containing nitrogen in the specific example group G2.

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 also the same as above.

In one embodiment, the a ring, the b ring and the c ring in the general formula (6) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms.

In one embodiment, the a, b and c rings in the above general formula (6) are each independently a substituted or unsubstituted benzene or naphthalene ring.

In one embodiment, R ₆₀₁ and R ₆₀₂ in formula (6) above are each independently

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

Preferably a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms.

In one embodiment, the compound represented by the above general formula (6) is a compound represented by the following general formula (62).

[ Chemical formula 258 ]

(In the above-mentioned general formula (62),

R _601A is bonded to 1 or more selected from R ₆₁₁ and R ₆₂₁ to form a substituted or unsubstituted heterocycle, or is not bonded to a substituted or unsubstituted heterocycle,

R _602A is bonded to 1 or more selected from R ₆₁₃ and R ₆₁₄ to form a substituted or unsubstituted heterocycle, or is not bonded to a substituted or unsubstituted heterocycle,

R _601A and R _602A which do not form the above-mentioned substituted or unsubstituted heterocycle are each independently

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

More than 1 group of groups consisting of adjacent more than 2 of R ₆₁₁～R₆₂₁

Is not bonded with each other and is not bonded with each other,

R ₆₁₁～R₆₂₁ which does not form the above-mentioned substituted or unsubstituted heterocycle and which does not form the above-mentioned substituted or unsubstituted monocyclic ring and which does not form the above-mentioned substituted or unsubstituted condensed ring is each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by Si (R ₉₀₁)(R₉₀₂)(R₉₀₃),

A group represented by-O- (R ₉₀₄),

A group represented by S- (R ₉₀₅),

A group represented by-N (R ₉₀₆)(R₉₀₇),

Halogen atom,

Cyano group,

Nitro group,

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

R _601A and R _602A in the general formula (62) are groups corresponding to R ₆₀₁ and R ₆₀₂ in the general formula (6), respectively.

For example, R _601A and R ₆₁₁ may be bonded to each other to form a nitrogen-containing heterocyclic ring in which 2 rings (or 3 or more rings) including a ring and a benzene ring corresponding to the a ring are condensed. Specific examples of the nitrogen-containing heterocycle include compounds corresponding to a heterocyclic group condensed at least 2 rings containing nitrogen 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 also the same as above.

More than 1 group of the groups consisting of adjacent more than 2 of R ₆₁₁～R₆₂₁ can

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.

For example, R ₆₁₁ and R ₆₁₂ may be bonded to each other to form a structure in which a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, or the like is condensed with respect to the six-membered ring to which they are bonded, and the condensed ring thus formed may be a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring, or a dibenzothiophene ring.

In one embodiment, R ₆₁₁～R₆₂₁ not involved in the formation of the ring are each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

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

A hydrogen atom,

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

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

Hydrogen atom, or

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

Hydrogen atom, or

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

At least 1 of R ₆₁₁～R₆₂₁ 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 259 ]

(In the above-mentioned general formula (63),

R ₆₃₁ is bonded to R ₆₄₆ to form a substituted or unsubstituted heterocycle, or to form no substituted or unsubstituted heterocycle,

R ₆₃₃ is bonded to R ₆₄₇ to form a substituted or unsubstituted heterocycle, or to form no substituted or unsubstituted heterocycle,

R ₆₃₄ is bonded to R ₆₅₁ to form a substituted or unsubstituted heterocycle, or to form no substituted or unsubstituted heterocycle,

R ₆₄₁ is bonded to R ₆₄₂ to form a substituted or unsubstituted heterocycle, or to form no substituted or unsubstituted heterocycle,

More than 1 group of groups consisting of adjacent more than 2 of R ₆₃₁～R₆₅₁

Is not bonded with each other and is not bonded with each other,

R ₆₃₁～R₆₅₁ which does not form the above-mentioned substituted or unsubstituted heterocycle and which does not form the above-mentioned substituted or unsubstituted monocyclic ring and which does not form the above-mentioned substituted or unsubstituted condensed ring is each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by Si (R ₉₀₁)(R₉₀₂)(R₉₀₃),

A group represented by-O- (R ₉₀₄),

A group represented by S- (R ₉₀₅),

A group represented by-N (R ₉₀₆)(R₉₀₇),

Halogen atom,

Cyano group,

Nitro group,

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

R ₆₃₁ may be bonded to R ₆₄₆ to form a substituted or unsubstituted heterocycle. For example, R ₆₃₁ and R ₆₄₆ may be bonded to each other to form a nitrogen-containing heterocyclic ring in which a benzene ring to which R ₆₄₆ is bonded, a ring containing N, and 3 or more rings of the benzene ring corresponding to the a ring are condensed. Specific examples of the nitrogen-containing heterocycle include compounds corresponding to a 3-ring or more condensed heterocyclic group containing nitrogen in the specific example group G2. The case where R ₆₃₃ is bonded to R ₆₄₇, the case where R ₆₃₄ is bonded to R ₆₅₁, and the case where R ₆₄₁ is bonded to R ₆₄₂ are also the same as above.

In one embodiment, R ₆₃₁～R₆₅₁ not involved in the formation of the ring are each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

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

A hydrogen atom,

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

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

Hydrogen atom, or

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

Hydrogen atom, or

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

At least 1 of R ₆₃₁～R₆₅₁ 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 260 ]

(In the above-mentioned general formula (63A),

R ₆₆₁ is

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

Substituted or unsubstituted cycloalkyl having 3 to 50 ring members, or

R ₆₆₂～R₆₆₅ are each independently

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

Substituted or unsubstituted cycloalkyl having 3 to 50 ring members, or

Substituted or unsubstituted aryl groups having 6 to 50 ring-forming carbon atoms. )

In one embodiment, each R ₆₆₁～R₆₆₅ is independently

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

Substituted or unsubstituted aryl groups having 6 to 50 ring-forming carbon atoms.

In one embodiment, R ₆₆₁～R₆₆₅ is 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 261 ]

(In the above-mentioned general formula (63B),

R ₆₇₁ and R ₆₇₂ are each independently of the other

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

-A group represented by N (R ₉₀₆)(R₉₀₇), or

R ₆₇₃～R₆₇₅ are each independently

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

-A group represented by N (R ₉₀₆)(R₉₀₇), or

In one embodiment, the compound represented by the above general formula (63) is a compound represented by the following general formula (63B').

[ Chemical formula 262 ]

(In the above general formula (63B'), R ₆₇₂～R₆₇₅ each independently has the same meaning as R ₆₇₂～R₆₇₅ in the above general formula (63B))

In one embodiment, at least 1 of R ₆₇₁～R₆₇₅ is

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

-A group represented by N (R ₉₀₆)(R₉₀₇), or

In one embodiment of the present invention, in one embodiment,

R ₆₇₂ is

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

-A group represented by N (R ₉₀₆₎(R₉₀₇), or

R ₆₇₁ and R ₆₇₃～R₆₇₅ are each independently of the other

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

-A group represented by N (R ₉₀₆₎(R₉₀₇), or

In one embodiment, the compound represented by the above general formula (63) is a compound represented by the following general formula (63C).

[ Chemical formula 263 ]

(In the above-mentioned general formula (63C),

R ₆₈₁ and R ₆₈₂ are each independently of the other

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

Substituted or unsubstituted cycloalkyl having 3 to 50 ring members, or

R ₆₈₃～R₆₈₆ are each independently

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

Substituted or unsubstituted cycloalkyl having 3 to 50 ring members, or

In one embodiment, the compound represented by the above general formula (63) is a compound represented by the following general formula (63C').

[ Chemical formula 264 ]

(In the above general formula (63C'), R ₆₈₃～R₆₈₆ each independently has the same meaning as R ₆₈₃～R₆₈₆ in the above general formula (63C))

In one embodiment, each R ₆₈₁～R₆₈₆ is independently

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or

In one embodiment, R ₆₈₁～R₆₈₆ is each independently a substituted or unsubstituted aryl group of 6 to 50 ring carbons.

For the compound represented by the above general formula (6), the a ring, the b ring and the c ring may be first bonded with a linking group (a group containing N-R ₆₀₁ and a group containing N-R ₆₀₂) to produce an intermediate (reaction 1), and then bonded with a linking group (a group containing a boron atom) to produce a final product (reaction 2). In reaction 1, an amination reaction such as Buchwald-Hartwig reaction can be used. In Reaction 2, a tandem hetero-Friedel-Crafts Reaction (Tandem Hetero Friedel-Crafts Reaction) or the like may be used.

The compound represented by the general formula (6) can be produced by a known method.

(Specific example of the compound represented by the general formula (6))

Specific examples of the compound represented by the general formula (6) include the following compounds. The compound represented by the general formula (6) is not limited to the following specific examples.

[ 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 ]

In the organic EL element according to the present embodiment, the relationship between the singlet energy S ₁ (H2) of the second host material and the singlet energy S ₁ (D2) of the second dopant material preferably satisfies the following expression (expression 20).

S ₁(H2)>S₁ (D2), (mathematical formula 20)

By satisfying the relationship of the formula (formula 20) between the second host material and the second dopant material, singlet excitons generated in the second host material can easily transfer energy from the second host material to the second dopant material, and thus contribute to light emission (preferably fluorescence light emission) of the second dopant material.

In the organic EL element according to the present embodiment, the triplet energy T ₁ (H2) of the second host material and the triplet energy T ₁ (D2) of the second dopant material preferably satisfy the relationship of the following expression (expression 20A).

T ₁(D2)>T₁ (H2.) (mathematical formula 20A)

By the relationship of the second host material and the second dopant material satisfying the mathematical formula (mathematical formula 20A), triplet excitons generated in the second light emitting layer tend to move toward the first light emitting layer because they do not move on the second dopant material having higher triplet energy but move on the second host material.

In the organic EL element according to the present embodiment, the content of the second dopant material in the second light-emitting layer is preferably 0.5 mass% or more, more preferably more than 1.1 mass% and further preferably 1.2 mass% or more, and further preferably 1.5 mass% or more, of the total mass of the second light-emitting layer.

In the second light-emitting layer, the content of the second dopant material is preferably 10 mass% or less of the total mass of the second light-emitting layer, more preferably 7 mass% or less of the total mass of the second light-emitting layer, and still more preferably 5 mass% or less of the total mass of the second light-emitting layer.

In the organic EL element according to the present embodiment, the content of the second host material in the second light-emitting layer is preferably 60 mass% or more, more preferably 70 mass% or more, still more preferably 80 mass% or more, still more preferably 90 mass% or more, and still more preferably 95 mass% or more, of the total mass of the second light-emitting layer.

In the second light-emitting layer, the content of the second host material is preferably 99 mass% or less of the total mass of the second light-emitting layer.

Wherein, when the second light-emitting layer contains the second host material and the second dopant material, the upper limit of the total content of the second host material and the second dopant material is 100 mass%.

The present embodiment does not exclude materials other than the second host material and the second dopant material from being included in the second light-emitting layer.

The second light-emitting layer may contain only 1 kind of the second host material, or may contain 2 or more kinds. The second light emitting layer may contain only 1 kind of the second dopant material, or may contain 2 or more kinds.

In the organic EL element according to the present embodiment, the film thickness of the second light-emitting layer is preferably 3nm or more, more preferably 5nm or more. If the film thickness of the second light-emitting layer is 3nm or more, the film thickness is sufficient to induce recombination of holes and electrons in the second light-emitting layer.

In the organic EL element according to the present embodiment, the film thickness of the second light-emitting layer is preferably 15nm or less, more preferably 10nm or less. If the film thickness of the second light-emitting layer is 15nm or less, it is sufficiently thin so that triplet excitons move to the film thickness of the first light-emitting layer.

In the organic EL element according to the present embodiment, the film thickness of the second light-emitting layer is more preferably 3nm to 15 nm.

(Other layers of organic EL element)

The organic EL element according to the present embodiment may have 1 or more organic layers in addition to the first light-emitting layer and the second light-emitting layer. Examples of the organic layer include at least one layer selected from a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, an electron transport layer, a hole blocking layer, and an electron blocking layer.

The organic EL element according to the present embodiment may include, for example, an anode, a second light-emitting layer, a first light-emitting layer, and a cathode in this order, or may include an anode, a first light-emitting layer, a second light-emitting layer, and a cathode in this order by reversing the order of the second light-emitting layer and the first light-emitting layer. The effect of the above-described light-emitting layer being formed in a laminated structure can be expected by selecting a combination of host materials satisfying the relationship of the above-described expression (expression 1) regardless of the order of the first light-emitting layer and the second light-emitting layer.

In the organic EL element according to the present embodiment, the organic layer may be composed of only the first light-emitting layer and the second light-emitting layer, or may further include at least one layer selected from, for example, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole blocking layer, an electron blocking layer, and the like.

Preferably, the organic EL element according to the present embodiment includes the first light-emitting layer between the anode and the cathode, and the second light-emitting layer between the first light-emitting layer and the anode.

It is also preferable that the organic EL element according to the present embodiment includes the first light-emitting layer between the anode and the cathode, and the second light-emitting layer between the first light-emitting layer and the cathode.

The organic EL element according to the present embodiment preferably includes a hole transport layer between the light-emitting layer and the anode.

The organic EL element according to the present embodiment preferably includes an electron transport layer between the light-emitting layer and the cathode.

Fig. 2 shows a general structure of another example of the organic EL element according to the fourth embodiment.

The organic EL element 1A 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 is formed by stacking, in this order, a hole injection layer 6, a hole transport layer 7, a second light-emitting layer 52, a first light-emitting layer 51, an electron transport layer 8, and an electron injection layer 9 from the anode 3 side.

Fig. 3 shows a general structure of another example of the organic EL element according to the fourth embodiment.

The organic EL element 1B includes a substrate 2, an anode 3, a cathode 4, and an organic layer 10B disposed between the anode 3 and the cathode 4. The organic layer 10B is formed by stacking, in this order, the hole injection layer 6, the hole transport layer 7, the first light emitting layer 51, the second light emitting layer 52, the electron transport layer 8, and the electron injection layer 9 from the anode 3 side.

The present invention is not limited to the structure of the organic EL element shown in fig. 2 and 3.

(Third light-emitting layer)

The organic EL element according to the present embodiment may further include a third light-emitting layer.

Preferably, the third light emitting layer includes a third host material, the first host material, the second host material, and the third host material are different from each other, and the third light emitting layer includes at least a third dopant material, the first dopant material, the second dopant material, and the third dopant material are the same or different from each other, and a triplet energy T ₁ (H2) of the second host material and a triplet energy T ₁ (H3) of the third host material satisfy a relationship of the following mathematical formula (mathematical formula 5).

T ₁(H2)>T₁ (H3.) (mathematical formula 5)

The third dopant material is preferably a compound that emits light having a maximum peak wavelength of 500nm or less, and more preferably a compound that emits fluorescence having a maximum peak wavelength of 500nm or less.

When the organic EL element according to the present embodiment includes the third light-emitting layer, the triplet energy T ₁ (H1) of the first host material and the triplet energy T ₁ (H3) of the third host material preferably satisfy the relationship of the following expression (expression 6).

T ₁(H1)>T₁ (H3.) (mathematical formula 6)

The third host material is not particularly limited, and for example, in the present embodiment, a host material exemplified as the first host material and the second host material can be used.

The third dopant material is not particularly limited, and for example, the dopant materials exemplified as the first dopant material and the second dopant material in the above embodiment can be used.

In the organic EL element according to the present embodiment, the first light-emitting layer and the second light-emitting layer are preferably in direct contact.

In this specification, the layer structure of "the first light-emitting layer is directly connected to the second light-emitting layer" may include any one of the following schemes (LS 1), (LS 2), and (LS 3), for example.

(LS 1) generating a region where both the first host material and the second host material are mixed in the process of passing through the vapor deposition step of the compound related to the first light-emitting layer and the vapor deposition step of the compound related to the second light-emitting layer, the region being present at the interface between the first light-emitting layer and the second light-emitting layer.

(LS 2) when the first light-emitting layer and the second light-emitting layer contain a light-emitting compound, a region in which the first host material, the second host material, and the light-emitting compound are mixed is formed during the vapor deposition process of the compound of the first light-emitting layer and the vapor deposition process of the compound of the second light-emitting layer, and the region is present at the interface between the first light-emitting layer and the second light-emitting layer.

(LS 3) when the first light-emitting layer and the second light-emitting layer contain a light-emitting compound, a region formed of the first host material, or a region formed of the second host material is generated during the vapor deposition process of the compound of the first light-emitting layer and the vapor deposition process of the compound of the second light-emitting layer, and the region exists at the interface between the first light-emitting layer and the second light-emitting layer.

In the case where the organic EL element according to the present embodiment includes the third light-emitting layer, the first light-emitting layer is preferably directly connected to the second light-emitting layer, and the first light-emitting layer is preferably directly connected to the third light-emitting layer.

In this specification, the layer structure in which the "first light-emitting layer and the third light-emitting layer are directly connected" may include any one of the following schemes (LS 4), (LS 5), and (LS 6), for example.

(LS 4) generating a region where both the first host material and the third host material are mixed in the process of passing through the vapor deposition step of the compound related to the first light-emitting layer and the vapor deposition step of the compound related to the third light-emitting layer, the region being present at the interface between the first light-emitting layer and the third light-emitting layer.

(LS 5) in the case where the first light-emitting layer and the third light-emitting layer contain a light-emitting compound (dopant material), a region in which the first host material, the third host material, and the light-emitting compound are mixed is formed in the process of the vapor deposition process of the compound related to the first light-emitting layer and the vapor deposition process of the compound related to the third light-emitting layer, and the region is present at the interface between the first light-emitting layer and the third light-emitting layer.

(LS 6) when the first light-emitting layer and the third light-emitting layer contain a light-emitting compound, a region formed of the first host material, or a region formed of the third host material is generated during the vapor deposition process of the compound of the first light-emitting layer and the vapor deposition process of the compound of the third light-emitting layer, and the region exists at the interface between the first light-emitting layer and the third light-emitting layer.

In the case where the organic EL element according to the present embodiment has a interlayer, the interlayer is preferably disposed between the first light-emitting layer and the second light-emitting layer.

The interlayer is preferably an undoped layer. The interlayer is preferably a layer containing no luminescent compound (dopant material). The interlayer preferably does not contain metal atoms.

The interlayer comprises an interlayer material. The interlayer material is preferably not a luminescent compound.

The interlayer material is not particularly limited, and materials other than luminescent compounds are preferable.

Examples of the interlayer material include 1) heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, and phenanthroline derivatives, 2) carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, and phenanthroline derivativesCondensed aromatic compounds such as derivatives, 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 host material contained in the first light-emitting layer and the second host material contained in the second light-emitting layer.

When the interlayer contains a plurality of interlayer materials, the content of each interlayer material is preferably 10 mass% or more of the total mass of the interlayer.

In the interlayer, the content of the interlayer material is preferably 60 mass% or more of the total mass of the interlayer, more preferably 70 mass% or more of the total mass of the interlayer, still more preferably 80 mass% or more of the total mass of the interlayer, still more preferably 90 mass% or more of the total mass of the interlayer, and particularly preferably 95 mass% or more of the total mass of the interlayer.

The interlayer may contain only 1 interlayer material, or may contain 2 or more interlayer materials.

When the interlayer contains 2 or more interlayer materials, the upper limit of the total content of the 2 or more interlayer materials is 100 mass%.

The organic EL element according to the fourth embodiment does not exclude the inclusion of a material other than the interlayer material in the interlayer.

The interlayer may be formed of a single layer or may be formed by stacking two or more layers.

The thickness of the interlayer is not particularly limited, but is preferably 3nm to 15nm, more preferably 5nm to 10nm, per 1 layer.

The structure of the organic EL element will be further described. This configuration is common to the organic EL elements of the third and fourth embodiments. Hereinafter, the description of the symbols may be omitted.

(Substrate)

The substrate is used as a support for the organic EL element. As the substrate, for example, glass, quartz, plastic, or the like can be used. In addition, a flexible substrate may be used. A flexible substrate refers to a bendable (flexible) substrate. For example, a plastic substrate and the like can be cited. Examples of the material for forming the plastic substrate include polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, and polyethylene naphthalate. In addition, an inorganic vapor deposition film may be used.

(Anode)

The anode formed on the substrate is preferably formed of a metal, an alloy, a conductive compound, or a mixture thereof having a large work function (specifically, 4.0eV or more). Specifically, examples thereof include Indium Tin Oxide (ITO), indium Tin Oxide containing silicon or silicon Oxide, indium zinc Oxide, indium Oxide containing tungsten Oxide and zinc Oxide, and graphene. Examples of the metal material include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), and nitrides of metal materials (for example, titanium nitride).

These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by a sputtering method using a target in which zinc oxide is added in an amount of 1 mass% or more and 10 mass% or less to indium oxide. 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 tungsten oxide and 0.1 mass% or more and 1 mass% or less zinc oxide relative to indium oxide. The composition may be produced by vacuum vapor deposition, coating, ink jet, spin coating, or the like.

Among the EL layers formed on the anode, a hole injection layer formed in contact with the anode is formed using a composite material in which hole (hole) injection is easily performed regardless of the work function of the anode, and thus, a material (for example, a metal, an alloy, a conductive compound, or a mixture thereof) that can be used as an electrode material may be used, and further, an element belonging to the first group or the second group of the periodic table may be included.

An alkali metal such as lithium (Li) and cesium (Cs), an alkaline earth metal such as magnesium (Mg), calcium (Ca) and strontium (Sr), an alloy containing the same (for example, mgAg, alLi), a rare earth metal such as europium (Eu) and ytterbium (Yb), an alloy containing the same, and the like can be used as the material having a small work function. When the anode is formed using an alkali metal, an alkaline earth metal, or an alloy containing these metals, a vacuum vapor deposition method or a sputtering method can be used. In addition, when silver paste or the like is used, a coating method, an inkjet method, or the like may be used.

(Cathode)

The cathode preferably uses a metal, an alloy, a conductive compound, or a mixture thereof having a small work function (specifically, 3.8eV or less). Specific examples of such cathode materials include alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca) and strontium (Sr), and alloys containing the same (for example, mgAg, alLi), rare earth metals such as europium (Eu) and ytterbium (Yb), and alloys containing the same.

In the case where the cathode is formed using an alkali metal, an alkaline earth metal, or an alloy containing these metals, a vacuum vapor deposition method or a sputtering method can be used. In addition, in the case of using silver paste or the like, a coating method, an inkjet method, or the like may be used.

By providing the electron injection layer, the cathode can be formed using Al, ag, ITO, graphene, or various conductive materials such as indium oxide-tin oxide containing silicon or silicon oxide, regardless of the magnitude of the work function. These conductive materials may be formed into films by sputtering, inkjet, spin coating, or the like.

(Hole injection layer)

The hole injection layer is a layer containing a substance having high hole injection property. As the substance having high hole injection property, molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, or the like can be used.

Further, as a substance having high hole injection property, 4',4″ -tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4' -tris [ N- (3-methylphenyl) -N-phenylamino ] triphenylamine (abbreviated as MTDATA), 4 '-bis [ N- (4-diphenylaminophenyl) -N-phenylamino ] biphenyl (abbreviated as DPAB), 4' -bis (N- {4- [ N '- (3-methylphenyl) -N' -phenylamino ] phenyl } -N-phenylamino) biphenyl (abbreviated as DNTPD), 1,3, 5-tris [ N- (4-diphenylaminophenyl) -N-phenylamino ] benzene (abbreviated as DPA 3B), 3- [ N- (9-phenylcarbazol-3-yl) -N-phenylamino ] -9-phenylcarbazole (abbreviated as PCzPCA 1), 3, 6-bis [ N- (9-phenylcarbazol-3-yl) -N-phenylamino ] -9-phenylcarbazole (abbreviated as PCzPCA 2), 3- [ N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) amino ] -9-phenylcarbazole (abbreviated as PCzPCN 1) and the like, dipyrazino [2,3-f:20,30-h ] quinoxaline-2, 3,6,7,10, 11-hexacarbonitrile (HAT-CN).

As the substance having high hole injection property, a polymer compound (oligomer, dendrimer, polymer, or the like) may be used. Examples thereof include polymer compounds such as Poly (N-vinylcarbazole) (abbreviated as PVK), poly (4-vinyltriphenylamine) (abbreviated as PVTPA), poly [ N- (4- (N '- [4- (4-diphenylamino) phenyl ] phenyl-N' -phenylamino } phenyl) methacrylamide ] (abbreviated as PTPDMA), and Poly [ N, N '-bis (4-butylphenyl) -N, N' -bis (phenyl) benzidine ] (abbreviated as Poly-TPD). In addition, acid-added polymer compounds such as Poly (3, 4-ethylenedioxythiophene)/Poly (styrenesulfonic acid) (PEDOT/PSS) and polyaniline/Poly (styrenesulfonic acid) (PAni/PSS) can be used.

(Hole transporting layer)

The hole-transporting layer is a layer containing a substance having high hole-transporting property. As the hole transporting layer, an aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used. Specifically, 4' -bis [ N- (1-naphthyl) -N-phenylamino ] biphenyl (abbreviation: NPB), N ' -bis (3-methylphenyl) -N, N ' -diphenyl- [1,1' -biphenyl ] -4,4' -diamine (abbreviation: TPD), 4-phenyl-4 ' - (9-phenylfluoren-9-yl) triphenylamine (abbreviation: BAFLP), 4' -bis [ N- (9, 9-dimethylfluoren-2-yl) -N-phenylamino ] biphenyl (abbreviated as DFLDPBi), 4' -tris (N, N-diphenylamino) triphenylamine (abbreviated as TDATA), 4' -tris [ N- (3-methylphenyl) -N-phenylamino ] triphenylamine (abbreviated as MTDATA), 4' -bis [ N- (spiro-9, 9' -bifluorene-2-yl) -N-phenylamino ] biphenyl (abbreviated as BSPB), and the like. The substance described herein is mainly a substance having a hole mobility of 10 ^-6cm²/(v·s) or more.

The hole transport layer may be formed using a carbazole derivative such as CBP, 9- [4- (N-carbazolyl) ] phenyl-10-phenylanthracene (CzPA), 9-phenyl-3- [4- (10-phenyl-9-anthracenyl) phenyl ] -9H-carbazole (PCzPA), or an anthracene derivative such as t-BuDNA, DNA, DPAnth. Polymer compounds such as poly (N-vinylcarbazole) (PVK) and poly (4-vinyltriphenylamine) (PVTPA) may be used.

Any substance other than those having higher hole transport property than electrons may be used. The layer containing the substance having high hole-transporting property may be a single layer or a laminate of two or more layers of the substance.

(Electron transport layer)

The organic EL element according to the above embodiment preferably includes an electron transport layer between the light-emitting layer and the cathode.

The electron-transporting layer is a layer containing a substance having high electron-transporting property. Examples of the electron transport layer include 1) metal complexes such as aluminum complex, beryllium complex and zinc complex, 2) heteroaromatic compounds such as imidazole derivative, benzimidazole derivative, azine derivative, carbazole derivative and phenanthroline derivative, and 3) polymer compounds. Specifically, as the low-molecular organic compound, metal complexes such as Alq, tris (4-methyl-8-hydroxyquinoline) aluminum (abbreviated as Almq ₃), bis (10-hydroxybenzo [ h ] quinoline) beryllium (abbreviated as BeBq ₂), and BAlq, znq, znPBO, znBTZ can be used. In addition to the metal complex, a heteroaromatic compound such as 2- (4-biphenyl) -5- (4-tert-butylphenyl) -1,3, 4-oxadiazole (abbreviated as PBD), 1, 3-bis [5- (p-tert-butylphenyl) -1,3, 4-oxadiazol-2-yl ] benzene (abbreviated as OXD-7), 3- (4-tert-butylphenyl) -4-phenyl-5- (4-biphenyl) -1,2, 4-triazole (abbreviated as TAZ), 3- (4-tert-butylphenyl) -4- (4-ethylphenyl) -5- (4-biphenyl) -1,2, 4-triazole (abbreviated as p-ETAZ), bathophenanthroline (abbreviated as BPhen), bathocuproine (abbreviated as BCP), and 4,4' -bis (5-methylbenzoxazol-2-yl) stilbene (abbreviated as BzOs) may be used. In the above embodiment, benzimidazole compounds may be suitably used. The substance described herein is mainly a substance having an electron mobility of 10 ^-6cm²/(v·s) or more. It should be noted that any material other than the above may be used as the electron transport layer as long as it has higher electron transport property than hole transport property. The electron transport layer may be formed of a single layer or two or more layers of the above-mentioned materials.

In addition, a polymer compound may be used for the electron transport layer. 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), and the like can be used.

(Electron injection layer)

The electron injection layer is a layer containing a substance having high electron injection property. As the electron injection layer, alkali metals, alkaline earth metals, or a compound thereof, such as lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂), lithium oxide (LiOx), or the like, can be used. In addition, a material in which an alkali metal, an alkaline earth metal, or a compound thereof is contained in a substance having electron-transporting property, specifically, a material in which magnesium (Mg) is contained in Alq, or the like may be used. In this case, electron injection from the cathode can be performed more efficiently.

Alternatively, a composite material in which an organic compound and an electron donor (donor) are mixed may be used for the electron injection layer. Such a composite material generates electrons in an organic compound by an electron donor, and therefore is excellent in electron injection property and electron transport property. In this case, the organic compound is preferably a material excellent in transport of generated electrons, and specifically, for example, the above-mentioned materials (metal complex, heteroaromatic compound, and the like) constituting the electron transport layer can be used. The electron donor may be any material that exhibits electron donating properties to an organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferable, and examples thereof include lithium, cesium, magnesium, calcium, erbium, and ytterbium. The alkali metal oxide and alkaline earth metal oxide are preferable, and examples thereof include lithium oxide, calcium oxide, and barium oxide. In addition, a Lewis base such as magnesium oxide may be used. In addition, an organic compound such as tetrathiafulvalene (abbreviated as TTF) may be used.

(Layer Forming method)

The method for forming each layer of the organic EL element according to the above embodiment is not limited to the above, and known methods such as a dry film forming method including a vacuum deposition method, a sputtering method, a plasma method, and an ion plating method, a wet film forming method including a spin coating method, a dipping method, a flow coating method, and an ink jet method can be used.

(Film thickness)

The film thickness of each organic layer of the organic EL element of the above embodiment is not limited except for the cases specifically mentioned above. In general, if the film thickness is too small, defects such as pinholes tend to occur, and if the film thickness is too large, a high applied voltage is required, and the efficiency is deteriorated, so that it is generally preferable that the film thickness of each organic layer of the organic EL element is in the range of several nm to 1 μm.

Fifth embodiment

[ Electronic device ]

The electronic device according to the present embodiment includes any one of the organic EL elements of the above embodiments. Examples of the electronic device include a display device and a light emitting device. Examples of the display device include a display unit (for example, an organic EL panel module), a television, a mobile phone, a tablet pc, and a personal computer. Examples of the light emitting device include lighting and a vehicle lamp.

[ Modification of embodiment ]

The present invention is not limited to the above-described embodiments, and modifications, improvements, and the like within a range 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 layer, and a plurality of light-emitting layers may be stacked. In the case where the organic EL element has a plurality of light-emitting layers, it is preferable that at least 1 organic layer satisfies the conditions described in the above embodiment, and at least 1 light-emitting layer contains the compound of the first embodiment. In the case where 1 light-emitting layer among the plurality of light-emitting layers contains the compound of the first embodiment, for example, the other light-emitting layer may be a fluorescent light-emitting type light-emitting layer or a phosphorescent light-emitting type light-emitting layer using light emission by electron transition from a triplet excited state directly to a ground state.

In the case where the organic EL element has a plurality of light-emitting layers, the light-emitting layers may be provided adjacent to each other, or a so-called tandem-type organic EL element in which a plurality of light-emitting units are stacked with an intermediate layer interposed therebetween may be used.

In addition, for example, a barrier 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, and prevents at least any one of holes, electrons, and excitons.

For example, in the case where a blocking layer is disposed so as to be 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) on the cathode side of the blocking layer. In the case of the organic EL element including an electron transport layer, the barrier layer is preferably included between the light-emitting layer and the electron transport layer.

In addition, in the case where 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 (for example, a hole transporting layer) on the anode side of the blocking layer. When the organic EL element includes a hole transport layer, the blocking layer is preferably included between the light-emitting layer and the hole transport layer.

In addition, the blocking layer may be provided adjacent to the light-emitting layer so that excitation energy does not leak from the light-emitting layer to the peripheral layer. Excitons generated in the light-emitting layer are prevented from moving to a layer (for example, an electron transport layer, a hole transport layer, or the like) on the electrode side of the blocking layer.

Preferably the light emitting layer is bonded to the barrier layer.

The specific structure, shape, etc. in the practice of the present invention may be other structures, etc. within a range that can achieve the object of the present invention.

Examples

The present invention will be described in further detail with reference to examples. The present invention is not limited to any of these examples.

< Compound >

The structures of the compounds used for the production of the organic EL elements according to examples 1 and 2 are shown below. The compound BD-1 and the compound BD-4 correspond to the compounds represented by the general formula (1).

[ Chemical formula 277 ]

[ Formula 278 ]

The structures of comparative compounds used for the production of the organic EL elements according to comparative examples 1 and 2 are shown below.

[ Chemical formula 279 ]

The structures of other compounds used for the production of the organic EL devices according to examples 1 to 2 and comparative examples 1 to 2 are shown below.

[ Chemical formula 280 ]

[ Chemical formula 281 ]

[ Chemical formula 282 ]

[ Chemical formula 283 ]

< Production of organic EL element >

The organic EL element was fabricated and evaluated as follows.

Example 1

A glass substrate (size: 25 mm. Times.25 mm. Times.0.7 mm, manufactured by Geomatec Co., ltd.) having a transparent electrode of Indium Tin Oxide (ITO) of 130nm thickness was prepared as an anode. The glass substrate provided with the ITO transparent electrode was cleaned with nitrogen plasma for 100 seconds. By this cleaning treatment, the hole injection property of ITO is also improved.

The cleaned glass substrate is mounted on a substrate frame and is conveyed into a vacuum evaporation device.

Then, the surface of the ITO transparent electrode is coated with the ITO transparent electrode at a pressure of 10 ^-8 mbar to 10 ^-6 mbarAbove andThe following conditions co-vapor-deposited compound HT-1 and compound HA to form a hole injection layer (HI) having a film thickness of 10 nm. The proportion of the compound HT-1 in the hole injection layer was 97% by mass, and the proportion of the compound HA was 3% by mass.

Next, the compound HT-1 was vapor deposited after the formation of the hole injection layer, thereby forming a first hole transport layer (HT) having a film thickness of 80 nm.

The compound HT-2 was vapor deposited after the film formation of the first hole transport layer, and a second hole transport layer (also referred to as an Electron Blocking Layer) (EBL) having a film thickness of 10nm was formed.

A compound BH-1 (first host material (BH)) and a compound BD-1 (first dopant material (BD)) were co-evaporated on the second hole transport layer so that the ratio of the compound BH-1 was 98 mass% and the ratio of the compound BD-1 was 2 mass%, thereby forming a light-emitting layer having a film thickness of 25 nm.

The compound ET-1 was vapor deposited on the light-emitting layer to form a1 st electron transport layer (also referred to as a Hole Blocking Layer) (HBL) having a film thickness of 10 nm.

A2 nd electron transport layer (ET) having a film thickness of 15nm was formed by vapor deposition of a compound ET-2 on the 1 st electron transport layer (HBL).

Lithium fluoride (LiF) was deposited on the 2 nd electron transport layer to form an electron injection layer having a film thickness of 1 nm.

Metal A1 was deposited on the electron injection layer to form a cathode having a film thickness of 50 nm.

The fabricated element was sealed using a glass cover and a moisture absorbent in an inert nitrogen atmosphere containing less than 1ppm of water and oxygen.

The element configuration of example 1 is shown in a abbreviated form as follows.

ITO(130)/HT-1:HA(10,97%:3%)/HT-1(80)/HT-2(10)/BH-1:BD-1(25,98%:2%)/ET-1(10)/ET-2(15)/LiF(1)/Al(50)

The numbers in brackets indicate film thickness (units: nm). The number shown in percent (97%: 3%) represents the ratio (mass%) of compound HT-1 and compound HA in the hole injection layer, and the number shown in percent (98%: 2%) represents the ratio (mass%) of host material (compound BH-1) and dopant material (compound BD-1) in the light emitting layer.

An organic EL device according to example 2 was produced in the same manner as in example 1, except that the compound BD-1 of example 1 was replaced with the compound shown in table 1.

Comparative examples 1 to 2

Organic EL devices according to comparative examples 1 to 2 were produced in the same manner as in example 1, except that the compound BD-1 of example 1 was replaced with the compound shown in table 1.

< Evaluation of organic EL element >

The organic EL element thus produced was evaluated as follows. The evaluation results are shown in Table 1.

(Drive Voltage)

The current was supplied between the anode and the cathode so that the current density was 10mA/cm ², and the voltage (unit: V) at this time was measured.

(Maximum peak wavelength λp and emission spectrum half width FWHM)

The element was applied with a voltage so that the current density was 10mA/cm ², and the spectral emission luminance spectrum at this time was measured by a spectral emission luminance meter CS-2000 (manufactured by Konica Minolta Co., ltd.). From the obtained spectral emission luminance spectrum, the maximum peak wavelength λp (unit: nm) and the emission spectrum full width at half maximum FWHM (unit: nm) were obtained. FWHM is short for Full WIDTH AT HALF Maximum (Full width at half Maximum).

(External Quantum efficiency EQE)

The element was applied with a voltage so that the current density was 10mA/cm ², and the spectral emission luminance spectrum at this time was measured by a spectral emission luminance meter CS-2000 (manufactured by Konica Minolta Co., ltd.). Based on the obtained spectral emission luminance spectrum, external quantum efficiency EQE (unit:%) was calculated assuming lambertian radiation.

[ Table 1]

The organic EL element according to example 1 using the compound BD-1 and the organic EL element according to example 2 using the compound BD-4 have higher external quantum efficiency EQE than the organic EL element according to comparative example 1 using the comparative compound Ref-1 and the organic EL element according to comparative example 2 using the comparative compound Ref-2.

This shows that excellent external quantum efficiency EQE can be obtained by using the compound BD-1 and the compound BD-4 as fluorescent light emitting materials of the organic EL element.

Synthesis example

(Synthesis of Compound BD-1)

The method for synthesizing the compound BD-1 is described below.

[ Chemical formula 284 ]

[ Production of intermediate 1-1 ]

2, 6-Tetramethylpiperidine (42.0 mL (249.0 mmol)) was dissolved in 250mL of THF (tetrahydrofuran), and after cooling the solution to-78 ℃, a 2.5M hexane solution (100 mL (250 mmol)) of n-butyllithium was added dropwise thereto over 30 minutes using a cannula (Japanese text: lidi). The solution was stirred at-78 ℃ for 30 minutes. Triisopropyl borate (67.0 mL (290.5 mmol)) was slowly added over 30 minutes, and after stirring the mixture at-78℃for 1 hour, a solution of 1, 2-dibromo-4- (tert-butyl) benzene (24.24 g (83.0 mmol)) dissolved in 50mL of THF was added dropwise over 45 minutes at-78 ℃. The mixture was then warmed to room temperature over an overnight period.

The reaction mixture was poured into 300mL of ice-cold 1N-HCl and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtered, and concentrated. The crude product was used for the next reaction without purification.

The result of analysis of ¹ H-NMR spectrum of intermediate (1-1) is shown below.

¹H NMR(300MHz,DMSO-d₆)δ8.44(s,2H),7.62(d,1H),7.27(d,1H),1.25(s,9H).

[ Chemical formula 285 ]

[ Production of intermediate 1-2 ]

Intermediate 1-1 (27.86 g (82.96 mmol)) and potassium acetate (1.63 g (16.59 mmol)) were suspended in 332mL of acetonitrile.

Next, N-iodosuccinimide (22.4 g (99.55 mmol)) was added to the suspension at room temperature, and the mixture was stirred overnight.

After 300mL of 10% sodium sulfite was added to the reaction mixture, the aqueous layer was extracted with toluene, the organic layer was washed with saturated brine, dried over magnesium sulfate, filtered, and concentrated.

Purification of the crude product by silica gel column chromatography using heptane as eluent gave 22.1g (61% yield) of intermediate 1-2 as a white solid.

The result of analysis of ¹ H-NMR spectrum of intermediate (1-2) is shown below.

¹H NMR(300MHz,CD₂Cl₂)δ7.87(d,1H),7.67(d,1H),1.31(s,9H).

[ Formula 286 ]

[ Production of intermediates 1 to 3 ]

Intermediate 1-2 (12.41 g (29.70 mmol)), bis (4-t-butyl) phenylamine (7.96 g (28.28 mmol)) and sodium t-butoxide (3.81 g (39.60 mmol)) were added to 190mL of toluene.

The suspension was degassed 3 times and refilled with argon, and tris (dibenzylideneacetone) dipalladium (0) (777 mg (0.85 mmol)) and 982mg (1.70 mmol) of Xantphos were added to the reaction mixture. The suspension was degassed 2 times, refilled with argon and heated at 90 ℃ for 19 hours. The reaction was cooled to room temperature and diluted with toluene. The organic extract was washed with water, dried over magnesium sulfate, filtered, and the solution was concentrated. The residue was purified by silica gel column chromatography using cyclohexane as an eluent to give 8.62g (53% yield) of intermediate 1-3 as a white solid.

The results of the positive ion electrospray-ionization mass spectrometry (ESI-MS) analysis of the intermediates (1-3) are shown below.

ESI-MS(positive,m/z)：exact mass of C₃₀H₃₇Br₂N＝569.13;found570.2[M+1]⁺.

[ Chemical formula 287 ]

[ Production of intermediates 1 to 4 ]

2-Bromo-4-t-butylaniline (1.60 g (7.00 mmol)) was dissolved in 65mL of methylene chloride, and to this solution was added m-chloroperoxybenzoic acid (4.83 g (7.00 mmol)). The mixture was stirred at room temperature for 16 hours. The mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the organic layer was washed with 1N sodium isohexane to obtain 1.13g (62% yield) of the intermediate 1-4 as a yellow oil.

The result of analysis of ¹ H-NMR spectrum of intermediate (1-4) is shown below.

¹H NMR(600MHz,CDCl₃)δ7.83(d,J＝9.0Hz,1H),7.72(d,J＝1.8Hz,1H),7.49(dd,J＝1.8,9.0Hz,1H),1.35(s,9H).

[ Chemical formula 288 ]

[ Production of intermediates 1 to 5 ]

Intermediate 1-4 (25.2 g (97.6 mmol)) and 4- (tert-butyl) aniline (23.0 g (154 mmol)) were dissolved in 250ml toluene. Cesium carbonate (48.0 g (147 mmol)) and water 25ml were added. The orange reaction mixture was degassed 3 times and refilled with argon. 2,2 '-bis (diphenylphosphino) -1,1' -Binaphthyl (BINAP) (640 mg (1.03 mmol)) and palladium (II) acetate (110 mg (0.49 mmol)) were added, the suspension was degassed 3 times, refilled with argon and heated at 86℃for 22 hours. The dark reaction mixture was cooled to room temperature, initially washed with water (2X 150 ml), followed by 12% aqueous hydrochloric acid (2X 150m 1) and water (2X 100 ml). The organic layer was dried over sodium sulfate and filtered through a 12cm layer of silica gel. The silica gel layer was washed with toluene and the collected eluate was dried under vacuum to give 32.6g of intermediate 1-5 as orange oil. The product was used in the next step without further purification.

The result of analysis of ¹ H-NMR spectrum of intermediate (1-5) is shown below.

¹H NMR(300MHz,DMSO-d₆)δ9.42(s,1H),8.06(d,1H),7.50-7.39(m,2H),7.32-7.23(m,2H),7.22(d,1H),6.94(dd,1H),1.31(s,9H),1.19(s,9H).

[ Chemical formula 289 ]

[ Production of intermediates 1 to 6 ]

Intermediate 1-5 (28.0 g (85.8 mmol)) was dissolved in 80ml of tetrahydrofuran and 300ml of methanol. Ammonium chloride (148 g) and zinc (27.0 g (0.41 mol)) were added, followed by 1.5ml of concentrated hydrochloric acid solution. The temperature was raised to 50 ℃ maximum and the resulting orange reaction mixture was stirred for 15 minutes until the temperature was reduced to 40 ℃. Zinc (29.0 g (0.44 mol)) was added and the reaction mixture stirred for 1 hour. The grey suspension was filtered and the residual solid was washed with tetrahydrofuran. The collected eluate was concentrated under vacuum. The product was further purified by MPLC (medium pressure liquid chromatography ) using CombiFlash (registered trademark) company (silica gel, 0-4% gradient of heptane/ethyl acetate) to obtain the product as a yellow resin. The resin was dissolved in a mixture of heptane and dichloromethane, and the dichloromethane was removed under vacuum. The solution was left at room temperature until a solid formed. The solid was filtered off and washed with a small amount of heptane to give 10.2g of intermediate 1-6 as a white solid. The filtrate was concentrated under vacuum to 1:3 of volume and maintained at room temperature until a solid formed. The solid was filtered off and washed with a small amount of heptane, thus obtaining 4.5g of intermediate 1-6 as a white solid.

The results of the positive ion electrospray-ionization mass spectrometry (ESI-MS) analysis of intermediates (1-6) are shown below.

ESI-MS(positive,m/z):exact mass of C₂₀H₂₈N₂＝296.23;found 297.4[M+1]⁺.

[ Chemical formula 290 ]

[ Production of intermediates 1 to 7 ]

Intermediate 1-3 (16.1 g (28.2 mmol)), intermediate 1-6 (9.20 g (31.0 mmol)) and sodium t-butoxide (5.40 g (56.2 mmol)) were suspended in 100mL of toluene.

The red suspension was degassed 3 times, refilled with argon and heated to 60 ℃. Tris (dibenzylideneacetone) dipalladium (0) (740 mg (0.81 mmol)) and 2,2 '-bis (diphenylphosphino) -1,1' -Binaphthyl (BINAP) (1.04 g (1.67 mmol)) were dissolved in 20mL of toluene to prepare a catalyst solution, which was heated under reflux for 5 minutes. A fraction of 1 of the catalyst solution was added to the red suspension. The dark reaction mixture was heated at 74 ℃ for 4 hours. The reaction mixture was cooled to room temperature and filtered through a layer of 3cm Hyflo (registered trademark) filter aid. The organic layer was washed with water (2X 100 ml) and 100ml of saturated aqueous sodium chloride solution, followed by drying over sodium sulfate. The product was further purified by MPLC using CombiFlash Companion (silica gel, heptane of ethyl acetate/gradient 0-3%) to give 16.8g (75% yield) of intermediate 1-7 as red resin.

The results of the positive ion electrospray-ionization mass spectrometry (ESI-MS) analysis of intermediates (1-7) are shown below.

ESI-MS(positive,m/z)：exact mass of C₅₀H₆₄BrN₃＝785.43;found786.6[M+1]⁺.

[ Chemical formula 291 ]

[ Production of intermediates 1 to 8]

1- (Tert-butyl) -3, 5-dimethylbenzene (100 g (0.62 mol)) was dissolved in 700ml of acetic acid. Bromine (89.0 g (0.56 mol)) in 300ml of acetic acid was slowly added at a maximum temperature of 10 ℃ and stirring was continued for 3 hours up to a temperature of 17 ℃. Stirring was continued for 17 hours at room temperature. 300ml of a 3% aqueous solution of sodium thiosulfate was added dropwise, and the resulting reaction mixture was stirred for 30 minutes, followed by stirring at 5 ℃. The reaction mixture was filtered and the solid was dissolved in 400ml of dichloromethane. The solution was treated with 200ml of water and 200ml of saturated aqueous sodium bicarbonate solution, and then stirred for 5 minutes. The organic layer was washed with 300ml of water and 200ml of saturated aqueous sodium chloride solution. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The product was heated in 500ml of methanol until a clear solution formed. The solution was cooled to room temperature and stirred until a suspension formed. The suspension was filtered to give 67.0g of a white solid. By repeating the same crystallization step, an additional amount of solid was separated from the filtrate, thereby obtaining 101g (75% yield) of the intermediate 1-8 as a white solid in total.

The result of analysis of ¹ H-NMR spectrum of intermediate (1-8) is shown below.

¹H NMR(300MHz,CD₂Cl₂)δ7.15(s,2H),2.44(s,6H),1.33(s,9H).

[ Chemical formula 292 ]

[ Production of intermediates 1 to 9 ]

Intermediate 1-8 (7.0 g (29.0 mmol)) in 70ml of t-butylbenzene was cooled to-10 ℃. 30.6ml of a 1.9M solution of t-butyllithium in pentane was slowly added, the temperature was raised to room temperature, followed by stirring at room temperature for 15 minutes. The yellow suspension was cooled to-32 ℃, 20.3ml of 1.0M solution of tribromoborane in heptane was added dropwise, followed by stirring at room temperature for 15 minutes. The resulting suspension of intermediates 1-9 was used directly in the next step.

[ Chemical formula 293 ]

[ Production of intermediates 1 to 10 ]

70Ml of tert-butylbenzene containing intermediates 1-7 (7.10 g (9.02 mmol)) and N, N-diisopropylethylamine (6.3 ml (36 mmol)) were slowly treated at-54℃with half of the product suspension of intermediates 1-9. The green suspension was stirred until room temperature was reached. The remaining half of the product suspension of intermediates 1-9 was added at-52 ℃. The white suspension was stirred until room temperature was reached. 6.5ml of N, N-diisopropylethylamine was added thereto, and stirring was continued at room temperature for 22 hours. The white suspension was treated with 200ml of 10% aqueous sodium carbonate solution. The organic layer was washed with water (2X 100 ml) and 100ml of saturated aqueous sodium chloride solution, then dried over sodium sulfate and concentrated under vacuum. The product was further purified by MPLC using CombiFlash Companion (silica gel, heptane/toluene). The resulting resin was heated under reflux in methanol until a suspension formed. The suspension was cooled to room temperature and stirred for 1 hour. The suspension was filtered and the solid was washed with a small amount of methanol to give 3.1g (36% yield) of intermediate 1-10 as a white solid.

The results of the positive ion electrospray-ionization mass spectrometry (ESI-MS) analysis of intermediates (1-10) are shown below.

ESI-MS(positive,m/z)：exact mass of C₆₂H₇₉BBrN₃＝955.56;found956.8[M+1]⁺

[ Formula 294 ]

[ Production of Compound BD-1 ]

Intermediate 1-10 (2.58 g (2.70 mmol)) was dissolved in 50ml of anhydrous tert-butylbenzene. 2.9ml of a 1.6M solution of tert-butyllithium in pentane was slowly added at-40℃and the solution was then stirred for 1 hour to room temperature. Stirring was continued for 20 minutes at room temperature. The solution was cooled to-70 ℃ and 5.4ml of a 1.0M solution of tribromoborane in heptane was slowly added. The temperature of the reaction mixture was slowly raised to 31 ℃ over 30 minutes. N, N-diisopropylethylamine (1.9 ml (10.8 mmol)) was added slowly and the reaction mixture was heated at 136℃for 2 hours. The reaction mixture was cooled to room temperature and then poured into 25ml of 2-propanol. 25mol of water are added and the solution is stirred until a suspension is formed. The suspension was filtered and the solid was washed with ethanol. The product was further purified by MPLC using CombiFlash Companion (silica gel, heptane/10% dichloromethane) and the resulting solid was dissolved in DCM (dichloromethane) with 50ml of 2-propanol and 100ml of ethanol. The solution was concentrated under vacuum until a suspension formed. The suspension was cooled to room temperature and filtered to give 0.57g (24% yield) of compound BD-1 as a yellow solid.

The results of the positive ion electrospray-ionization mass spectrometry (ESI-MS) of the compound (BD-1) are shown below.

ESI-MS(positive,m/z)：exact mass of C₆₂H₇₇B₂N₃＝885.63;found886.8[M+1]⁺.

(Synthesis of Compound BD-2)

The method for synthesizing compound BD-2 is described below.

[ Chemical formula 295 ]

[ Production of intermediate 2-1 ]

2-Bromo-5- (tert-butyl) aniline (50.0 g (0.22 mol)) was suspended in 350ml of water and 90ml of 37% aqueous hydrochloric acid, and the suspension was cooled to 6 ℃. 59.1ml of 4M aqueous sodium nitrite were added dropwise over 15 minutes at a maximum temperature of 6 ℃. A solution of potassium iodide (53.5 g (0.32 mol)) in 120ml of water was added dropwise over 35 minutes at a maximum temperature of 4 ℃. The emulsion was stirred for 90 minutes to room temperature. 5% aqueous sodium sulfite solution (100 ml) and heptane (200 ml) were added. The organic layer was washed with water (3X 100 ml) and dried over sodium sulfate. The product was further purified by MPLC using CombiFlash Companion (silica gel, heptane) to give 52.4g of intermediate 2-1.

The result of analysis of ¹ H-NMR spectrum of intermediate (2-1) is shown below.

¹H NMR(300MHz,CD₂Cl₂)δ7.91(d,1H),7.57(d,1H),7.29(dd,1H),1.33(s,9H).

[ Chemical formula 296 ]

[ Production of intermediate 2-2 ]

Intermediate 2-1 (16.5 g (48.7 mmol)), phenylboronic acid (5.96 g (49.9 mmol)), tetrakis (triphenylphosphine) palladium (0) (1.13 g (0.98 mmol)) and sodium carbonate (15.5 g (146 mmol)) were suspended in 200ml of toluene and 60ml of water. The suspension was degassed 3 times, refilled with argon and heated at 66 ℃ for 6 hours. The reaction mixture was cooled to room temperature and diluted with 50ml of toluene. The organic layer was washed with water (3X 100 ml) and dried over sodium sulfate. The resulting oil was dissolved in 60ml of heptane and stirred for 30 minutes until a suspension was formed. The suspension was filtered and the filtrate was concentrated in vacuo to give a brown oil. The product was further refined by MPLC using CombiFlash Companion (silica gel, heptane) to give 7.68g (54% yield) of intermediate 2-2 as a slightly orange oil.

The result of analysis of ¹ H-NMR spectrum of intermediate (2-2) is shown below.

¹H NMR(300MHz,CD₂Cl₂)δ7.62(d,1H),7.53-7.41(d.1H),7.30(dd,1H),1.37(s.9H).

[ Chemical formula 297 ]

[ Production of intermediate 2-3 ]

1, 2-Dibromo-3-iodo-5-methylbenzene (40.2 g (106 mmol)) (prepared by the same method as intermediate 1-2, 3, 4-dibromotoluene was used as a starting material), bis (4- (tert-butyl) phenyl) amine (28.6 g (101 mmol)) and sodium tert-butoxide (26.0 g (0.27 mol)) were suspended in 400ml of toluene. The yellow suspension was degassed 3 times and refilled with argon. After the temperature was raised to 91 ℃,4, 5-bis (diphenylphosphino (phosphino)) -9, 9-dimethylxanthenes (Xantphos) (3.20 g (5.53 mmol)) and tris (dibenzylideneacetone) dipalladium (2.50 g (2.73 mmol)) were added. The dark reaction mixture was degassed 3 times and, after refilling with argon, heated at 87 ℃ for 32 hours. The reaction mixture was cooled to room temperature and filtered, and the filtrate was concentrated in vacuo. The dark brown powder was further refined by MPLC using CombiFlash Companion (silica gel, heptane/toluene 0-100% gradient). The product was dissolved in 400ml of dichloromethane and 300ml of methanol. The solution was concentrated under vacuum until a suspension formed. The suspension was diluted with 100ml of ethanol and stirred at room temperature for 30 minutes. The suspension was filtered and the solid was washed with ethanol to give 39.2g (69% yield) of intermediate 2-3 as a white solid.

The results of the positive ion electrospray-ionization mass spectrometry (ESI-MS) of intermediate (2-3) are shown below.

ESI-MS(positive,m/z)：exact mass of C₂₇H₃₁Br₂N＝527.08;found 528.2[M+1]⁺

[ Chemical formula 298 ]

[ Production of intermediate 2-4 ]

Intermediate 2-3 (20.2 g (38.2 mmol)), intermediate 1-6 (12.5 g (42.2 mmol)) and sodium tert-butoxide (6.70 g (69.7 mmol)) were suspended in 200ml toluene. The red suspension was degassed 3 times, refilled with argon and heated to 85 ℃. A catalyst solution was prepared by dissolving tris (dibenzylideneacetone) dipalladium (0) (1.04 g (1.14 mmol)) and 1.46g of 2,2 '-bis (diphenyl-phosphino (phosphino)) -1,1' -Binaphthyl (BINAP) in 40ml of toluene and heating under reflux for 5 minutes. The catalyst solution was added to the reaction mixture and heating was continued for 4 hours at 81 ℃. The dark reaction mixture was cooled to room temperature, diluted with dichloromethane and washed with water and saturated aqueous sodium chloride. The organic layer was dried over sodium sulfate and the product was further purified by MPLC using CombiFlash Companion (silica gel, heptane/toluene/ethyl acetate). The isolated product was dissolved in hot heptane and concentrated until a suspension was formed. The suspension was stirred at room temperature for 1 hour, followed by filtration and the solid was washed with heptane. The heptane precipitation step was repeated 1 time, yielding 19.8g (70% yield) of intermediate 2-4 as a yellow solid.

The results of the positive ion electrospray-ionization mass spectrometry (ESI-MS) analysis of intermediate (2-4) are shown below.

ESI-MS(positive,m/z)：exact mass of C₄₇H₅₈BrN₃＝743.38;found 744.5[M+1]⁺.

[ Chemical formula 299 ]

[ Production of intermediate 2-5 ]

Intermediate 2-2 (6.60 g (22.8 mmol)) in 60ml of t-butylbenzene was cooled to-10 ℃. 24.2ml of a 1.9M solution of tert-butyllithium in pentane was slowly added, the temperature was raised to room temperature, followed by stirring at room temperature for 45 minutes. The orange suspension was cooled to-78 ℃, 17.3ml of 1.0M solution of tribromoborane in heptane was added dropwise, followed by stirring at room temperature for 15 minutes. The yellow suspension of intermediate 2-5 obtained was used directly in the next step.

[ Chemical formula 300 ]

[ Production of intermediate 2-6 ]

Intermediate 2-4 (6.00 g (15.8 mmol)) was heated in 60ml of t-butylbenzene until a solution was formed. N, N-diisopropylethylamine (5.6 ml (32.2 mmol)) was added and the mixture was cooled to-78 ℃. The crude product suspension of intermediate 2-5 was slowly added and the resulting reaction suspension was warmed to room temperature over 90 minutes. Stirring was continued for 15 minutes at room temperature. The reaction mixture was treated with 300ml of water and the separated organic layer was washed with water (2X 100 ml) and dried over sodium sulfate. The product was further purified by MPLC using CombiFlash Companion (silica gel, 0-20% gradient of heptane/dichloromethane). The isolated product was heated in methanol until a suspension formed. The suspension was cooled to room temperature and filtered. The solid was washed with methanol and dissolved in a minimum of dichloromethane and 40ml of 2-propanol. The solution was concentrated under vacuum until a suspension formed. The suspension was filtered and the solid was washed with 2-propanol to give 5.92g (76% yield) of intermediate 2-6 as a white solid.

The results of the positive ion electrospray-ionization mass spectrometry (ESI-MS) analysis of the intermediates (2-6) are shown below.

ESI-MS(positive,m/z)：exact mass of C₆₃H₇₃BBrN₃＝961.51;found 962.6[M+1]⁺

[ Chemical formula 301 ]

[ Production of Compound BD-2 ]

Intermediate 2-6 (3.40 g (3.53 mmol)) was dissolved in 60ml of anhydrous tert-butylbenzene. 3.8ml of a 1.9M solution of t-butyllithium in pentane was slowly added at-28℃and stirring continued for 10 minutes to room temperature followed by 30 minutes at 35 ℃. The solution was cooled to-20 ℃ and 7.1ml of a 1.0M solution of tribromoborane in heptane was slowly added to raise the temperature to 41 ℃. N, N-diisopropylethylamine (2.5 ml (14 mmol)) was added slowly and the reaction mixture was heated at 168℃for 18 hours. The yellow suspension was cooled to room temperature and extracted with 10% aqueous sodium acetate (2X 30 ml). The organic layer was separated, dried over sodium sulfate and filtered through a 3cm layer of silica gel. The silica gel layer was washed with heptane and toluene. The combined eluates were concentrated in vacuo. The yellow oil was stirred in 30ml of acetone until a suspension formed. The suspension was filtered and the solid was further purified by MPLC using CombiFlash Companion (silica gel, heptane/0-100% dichloromethane gradient). The product was suspended 2 times in 15ml of acetone, and the suspension was filtered to obtain 0.65g (20% yield) of compound BD-2 as a yellow solid.

The results of the positive ion electrospray-ionization mass spectrometry (ESI-MS) of the compound (BD-2) are shown below.

ESI-MS(positive,m/z)：exact mass of C₆₃H₇₁B₂N₃＝891.58;found 892.7[M+1]⁺.

(Synthesis of Compound BD-3)

The following describes a method for synthesizing compound BD-3.

[ Chemical formula 302 ]

[ Production of intermediate 3-1 ]

4- (Tert-butyl) -2-chloroaniline (50.0 g (0.27 mol)) was dissolved in 400ml of tetrahydrofuran. The solution was cooled and N-bromosuccinimide (50.9 g (0.29 mol)) was added in several portions at a maximum temperature of 4 ℃. The reaction mixture was stirred at 4 ℃ for 25 minutes, followed by the addition of water (100 mL), sodium bisulphite (3 g) and heptane (300 mL). The mixture was stirred for 15 minutes. The organic layer was separated and washed with 100ml of 10% aqueous sodium bicarbonate and water (3X 100 ml). The organic layer was separated, dried over sodium sulfate and concentrated under vacuum to give 58.3g (81% yield) of intermediate 3-1.

The result of analysis of ¹ H-NMR spectrum of intermediate (3-1) is shown below.

¹H NMR(300MHz,CD₂Cl₂)δ7.40(d,1H),7.29(d,1H),4.38(br.s,2H),1.30(s,9H).

[ Chemical formula 303 ]

[ Production of intermediate 3-2 ]

Intermediate 3-1 (58.0 g (0.22 mol)) was suspended in 230ml of 37% aqueous hydrochloric acid and cooled to-2 ℃. 66.3ml of 4M aqueous sodium nitrite solution were added dropwise at a maximum temperature of 3 ℃. 160ml of a solution of 32.8g (0.33 mol) of copper (I) chloride in 37% aqueous hydrochloric acid was added dropwise over 40 minutes at a maximum temperature of 8 ℃. Stirring was continued for 45 minutes at 3 ℃. The brown suspension was slowly treated with 600ml of water, followed by filtration and the solid was washed with 500ml of water. The solid was suspended in 150ml of 10% ammonia water, the suspension was stirred for 10 minutes, followed by 200ml of heptane. The organic layer was washed with water (2X 200 ml), dried over sodium sulfate, and filtered. The resulting red solution was further filtered through a 4cm silica gel layer, which was subsequently washed with 50ml of heptane. The collected eluate was concentrated under vacuum to give 52.3g (84%) of intermediate 3-2 as a pink solid.

The result of analysis of ¹ H-NMR spectrum of intermediate (3-2) is shown below.

¹H NMR(300MHz,CD₂Cl₂)δ7.62(d,1H),7.50(d,1H),1.33(s,9H).

[ Chemical formula 304 ]

[ Production of intermediate 3-3 ]

Intermediate 3-2 (7.39 g (26.2 mmol)), 4-tert-butylbenzene (4.19 g (27.5 mmol)) and sodium tert-butoxide (6.49 g (65.5 mmol)) were added to 250mL of xylene. The suspension was degassed using 3 freeze pump thaw cycles and tris (dibenzylideneacetone) dipalladium (0) (247 mg (0.26 mmol)) and BINAP (673 mg (1.05 mmol)) were added to the reaction mixture. Further, after 2 freeze-pump-thaw cycles, the reaction mixture was heated at 90 ℃ for 2.5 hours. The reaction was cooled to room temperature and diluted with toluene. The organic extract was washed with water and saturated brine, and then dried over magnesium sulfate. It was filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography using a mixed solvent of heptane and dichloromethane as an eluent, to obtain 7.73g (yield of 84%) of intermediate 3-3 as an orange oil.

The results of the positive ion electrospray-ionization mass spectrometry (ESI-MS) of intermediate (3-3) are shown below.

ESI-MS(positive,m/z):351[M+H].

[ Chemical formula 305 ]

[ Production of intermediate 3-4 ]

Intermediate 3-3 (7.72 g (22.03 mmol)), 3-bromobenzo [ b ] thiophene (5.38 g (24.23 mmol)) and sodium tert-butoxide 5.29g (55.1 mm0 l) were added to 220mL of toluene. The suspension was degassed using 3 freeze pump thaw cycles and tris (dibenzylideneacetone) dipalladium (0) (208 mg (0.22 mmol)) and tri-tert-butyl-squamous tetrafluoroborate (264 mg (0.88 mmol)) were added to the reaction mixture. Further, after 2 freeze-pump-thaw cycles, the reaction mixture was heated at 95 ℃ for 1.5 hours. After the reaction mixture was cooled to room temperature, tris (dibenzylideneacetone) dipalladium (0) (104 mmg (0.11 mm0 l)) and tri-tert-butylphosphonium tetrafluoroborate (132 mg (0.44 mmol)) were added to the reaction mixture. Further, after 2 freeze-pump-thaw cycles, the reaction mixture was heated at 85 ℃ for 1.5 hours. After the reaction was cooled to room temperature, water was added, and the aqueous layer was washed with ethyl acetate. The organic extract was washed with water and saturated brine, and dried over magnesium sulfate. It was filtered and the filtrate was concentrated. The residue was purified by silica gel column chromatography using a mixed solvent of heptane and dichloromethane as an eluent, to obtain 8.76g (82% yield) of intermediate 3-4 as a white solid.

The results of the positive ion electrospray-ionization mass spectrometry (ESI-MS) of intermediate (3-4) are shown below.

ESI-MS(positive,m/z):484[M+H].

[ Chemical formula 306 ]

[ Production of intermediate 3-5 ]

Intermediate 3-4 (8.53 g (17.68 mmol)), N-phenyl-1, 2-diamine (3.93 g (20.90 mmol)) and sodium t-butoxide (4.38 g (44.2 mmol)) were added to 200mL of xylene. The suspension was degassed using 3 freeze pump thaw cycles and tris (dibenzylideneacetone) dipalladium (0) (334 mg (0.35 mmol)) and tri-tert-butyl-squamous tetrafluoroborate (423 mg (1.41 mmol)) were added to the reaction mixture. Further, after 2 freeze-pump-thaw cycles, the reaction mixture was heated at 135 ℃ for 3.5 hours. After the reaction mixture was cooled to room temperature, water was added to the reaction mixture, and the aqueous layer was washed with ethyl acetate. The organic extract was washed with water and saturated brine, and then dried over magnesium sulfate. It was filtered and the filtrate was concentrated. The residue was purified by silica gel column chromatography using a mixed solvent of heptane and dichloromethane as an eluent, to obtain 9.53g (85% yield) of intermediate 3-5 as a pale red solid.

The results of the positive ion electrospray-ionization mass spectrometry (ESI-MS) of intermediate (3-5) are shown below.

ESI-MS(positive,m/z):631[M+H].

[ Chemical formula 307 ]

[ Production of intermediate 3-6 ]

Intermediate 3-5 (2.28 g (3.62 mmol)) and triethylamine (2.14 mL (15.34 mmol)) were added to 30mL of toluene and the solution was cooled to 0 ℃. A solution of intermediate 1-9 (2.64 g (3.98 mmol)) dissolved in 20mL of toluene was added dropwise to the solution at 0deg.C. After the reaction mixture was stirred at room temperature for 45 minutes, water was added, and the aqueous layer was washed with ethyl acetate. The organic extract was washed with water and saturated brine, and then dried over magnesium sulfate. It was filtered and the filtrate was concentrated. The residue was purified by silica gel column chromatography using a mixed solvent of heptane and dichloromethane as an eluent. The purified product was dissolved in methylene chloride, and after addition of heptane, methylene chloride was removed under reduced pressure until a solid was formed. The solid was filtered off by filtration, yielding 2.48g (33% yield) of intermediate 3-6 as a pale red solid.

The results of the positive ion electrospray-ionization mass spectrometry (ESI-MS) analysis of intermediate (3-6) are shown below.

ESI-MS(positive,m/z):801[M+H].

[ Chemical formula 308 ]

[ Production of Compound BD-3 ]

Intermediate 3-6 (2.48 g (3.10 mmol)) was added to 90mL of t-butylbenzene and the solution was bubbled with argon. 3.26mL of t-butyllithium (1.9M in pentane) was added dropwise to the 0℃solution, and the reaction mixture was stirred at 0℃for 1 hour. Then, the reaction mixture was warmed to room temperature and stirred for 7 hours. The reaction mixture was cooled to-30 ℃, boron tribromide (0.59 mL (6.20 mmol)) was added, and after the reaction mixture was warmed to room temperature and stirred for 1 hour. After the reaction mixture was warmed to 0 ℃, N-ethyl-N-isopropyl-propan-2-amine (2.71 mL (15.49 mmol)) was added. The mixture was then heated to 165 ℃ and stirred overnight. After the reaction, the mixture was cooled to room temperature, and 10% aqueous sodium acetate solution was added. The mixture was diluted with ethyl acetate, and the aqueous layer was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over magnesium sulfate. It was filtered and concentrated. The residue was purified by silica gel column chromatography using a mixed solvent of heptane and dichloromethane as an eluent, to obtain 0.47g (19% yield) of compound BD-3 as a yellow powder.

The results of the positive ion electrospray-ionization mass spectrometry (ESI-MS) of the compound (BD-3) are shown below.

ESI-MS(positive,m/z):775[M+H].

(Synthesis of Compound BD-4)

The following describes a method for synthesizing compound BD-4.

[ Chemical formula 309 ]

[ Production of intermediate 4-1 ]

3-Bromo-N, N-bis (4- (tert-butyl) phenyl) aniline (16.0 g (36.7 mmol)), 9-dimethyl-9H-fluoren-2-amine (8.61 g (40.3 mmol)) and sodium tert-butoxide (4.93 g (51.3 mmol)) were added to 183ml of toluene. The suspension was degassed using 3 freeze pump thaw cycles and tris (dibenzylideneacetone) dipalladium (0) (504 mg (0.55 mmol)) and BINAP (685 mg (1.10 mmol)) were added to the reaction mixture. Further, after 2 freeze-pump-thaw cycles, the reaction mixture was heated at 100 ℃ for 4 hours. The reaction was cooled to room temperature and diluted with toluene. The organic extract was washed with water and then dried over magnesium sulfate. It was filtered and the filtrate was concentrated. The residue was purified by silica gel column chromatography using a mixed solvent of heptane and dichloromethane as an eluent, to obtain 20.1g (94% yield) of intermediate 4-1 as a yellow foam.

The results of the positive ion electrospray-ionization mass spectrometry (ESI-MS) of intermediate (4-1) are shown below.

ESI-MS(positive,m/z):exact mass of C₄₁H₄₄N₂=564.35;found 565.6[M+H].

[ Chemical formula 310 ]

[ Production of intermediate 4-2 ]

Intermediate 4-1 (40.0 g (70.8 mmol)), intermediate 1-2 (44.4 g (106 mmol)) and sodium tert-butoxide (9.53 g (99.0 mmol)) were added to 708ml of toluene. The suspension was degassed using 3 freeze pump thaw cycles and tris (dibenzylideneacetone) dipalladium (0) (1.85 g (2.02 mmol)) and Xantphos (2.34 g (4.04 mmol)) were added to the reaction mixture. Further, after 2 freeze-pump-thaw cycles, the reaction mixture was heated at 95 ℃ for 46 hours. The reaction was cooled to room temperature, filtered through a pad of silica gel, washed with toluene, and the solution was concentrated. The crude product was purified by silica gel column chromatography using a mixed solvent of heptane and dichloromethane as an eluent, to obtain 42.2g (69% yield) of intermediate 4-2 as pale yellow foam.

The results of the positive ion electrospray-ionization mass spectrometry (ESI-MS) of intermediate (4-2) are shown below.

ESI-MS(positive,m/z)：exact mass of C₅₁H₅₄Br₂N₂＝852.27;found 855.5[M+H].

[ Chemical formula 311 ]

[ Production of intermediate 4-3 ]

Intermediate 4-2 (11.0 g (12.9 mmol)), intermediate 1-6 (4.20 g (14.2 mmol)) and potassium carbonate (2.50 g (18.0 mmol)) were suspended in 100ml of t-butanol. The suspension was heated at 30 ℃, 0.35G (0.65 mmol) of BrettPhos (=cas 1070663-78-3) and 0.57G (0.64 mmol) of BrettPhos-Pd-G1 (=cas 1148148-01-9) were added and the suspension was heated at 81 ℃ for 2 hours. The pale green suspension was cooled to room temperature and poured into water (800 m 1) and ethanol (100 ml). The suspension was stirred for 30 minutes and filtered. The solid was dissolved in dichloromethane, dried over magnesium sulfate and filtered through a 5cm layer of silica gel. The silica gel layer was washed with dichloromethane (200 ml). The collected eluate was diluted with ethanol (200 ml). The solution was collected under vacuum and the residual solid was stirred in ethanol (300 ml) under reflux and concentrated to a volume of 250 ml. The suspension was cooled to room temperature and filtered to give 11.0g (80% yield) of intermediate 4-3 as a pale green solid.

The results of the positive ion electrospray-ionization mass spectrometry (ESI-MS) of intermediate (4-3) are shown below.

ESI-MS(positive,m/z):exact mass of C₇₁H₈₁BrN₄=1068.56;found 1071.7[M+H].

[ Chemical formula 312 ]

[ Production of intermediates 1 to 9 ]

Intermediate 1-8 (1.94 g (8.0 mmol)) was dissolved in tert-butylbenzene (60 ml). 11.5ml of a 1.4M solution of sec-butyllithium in cyclohexane was slowly added thereto and stirred at room temperature for 3 hours. The slightly orange cloudy solution was treated with 1.0M solution of tribromoborane in heptane (3.3M 1) at-30℃and stirred for a further 1 hour at room temperature. Orange suspension of intermediates 1-9 was used directly in the next step.

[ Chemical formula 313 ]

[ Production of intermediate 4-4 ]

80Ml of intermediate 4-3 (8.OOg (7.47 mmol)) and triethylamine (4.2 ml (30 mmol)) in tert-butylbenzene were slowly treated with a product suspension of intermediate 1-9 at room temperature. The reaction mixture was stirred at room temperature for 18 hours. 50ml of saturated sodium bicarbonate solution was added and stirred for 10 minutes. The organic layer was separated, washed with 50ml of water, dried over sodium sulfate, and filtered. The solution was concentrated in vacuo and further purified by MPLC using CombiFlash Companion (silica gel, heptane/toluene) to give 3.01g (32% yield) of intermediate 4-4 as a white foam.

The results of the positive ion electrospray-ionization mass spectrometry (ESI-MS) of intermediate (4-4) are shown below.

ESI-MS(positive,m/z)：exact mass of C₈₃H₉₆BBrN₄＝1238.69;found 1241.6[M+1]⁺.

[ Chemical formula 314 ]

[ Production of Compound BD-4 ]

Intermediate 4-4 (1.90 g (1.53 mmol)) was dissolved in 50ml of anhydrous tert-butylbenzene. 1.6ml of a 1.9M solution of t-butyllithium in pentane was slowly added at room temperature and stirred for 2 hours. The pale orange suspension was slowly treated with trimethyl borate (0.5 ml (4.5 mmol)) and stirred at room temperature for 30 min. Boron tribromide (0.9 ml (9.5 mmol)) was added at-30 ℃. The dark orange suspension was initially stirred at room temperature for 2 hours, followed by stirring at 60 ℃ for 3 hours, after which it was stirred at 90 ℃ overnight. N, N-diisopropylethylamine (3.2 ml (18.4 mmol)) was added slowly and stirring continued for 5 minutes. The yellow suspension was treated with 5ml of water and diluted with ethanol while stirring until a suspension was formed. The suspension was stirred for 30 minutes, followed by filtration. The residual solid was stirred in 50ml of ethanol and subsequently filtered. Final stirring was performed in 50ml of ethanol and 50ml of pentane, yielding 1.1g (61% yield) of compound BD-4 as a yellow solid.

The results of the positive ion electrospray-ionization mass spectrometry (ESI-MS) of the compound (BD-4) are shown below.

ESI-MS(positive,m/z)：exact mass of C₈₃H₉₄B₂N₄＝1168.77;found 1169.9[M+1]⁺.

Symbol description

1,1A,1 b..an organic EL element, 2..a substrate, 3..an anode, 4..a cathode, 5..an emission layer, 6..a hole injection layer, 7..a hole transport layer, 8..an electron transport layer, 9..an electron injection layer, 10a,10 b..an organic layer, 51..a first emission layer, 52..a second emission layer, 67..1 st organic layer, 89..2 nd organic layer.

Claims

1. A compound represented by the following general formula (1),

In the general formula (1) described above,

Ring A1, ring B1 and ring C1 are each independently

Is not bonded with each other and is not bonded with each other,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by-N (R ₁₃₁)(R₁₃₂),

A group represented by Si (R ₁₃₃)(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C (=O) R ₁₃₈ a group,

A group represented by COOR ₁₃₉,

Halogen atom,

Cyano group,

Nitro group,

-A group represented by P (=O) (R ₁₄₀)(R₁₄₁),

A group represented by Ge (R ₁₄₂)(R₁₄₃)(R₁₄₄),

A group represented by (R ₁₄₅)(R₁₄₆),

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

X is

An oxygen atom,

A sulfur atom,

N(R₁₀₁)、

Si (R ₁₀₂)(R₁₀₃), or

C(R₁₀₄)(R₁₀₅),

R ₁₀₁ is

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by Si (R ₁₃₃)(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Substituted or unsubstituted aralkyl group having 7 to 50 carbon atoms,

-C (=O) R ₁₃₈ a group,

A group represented by COOR ₁₃₉,

Halogen atom,

Cyano group,

Nitro group,

-A group represented by P (=O) (R1 ₄₀)(R₁₄₁),

A group represented by Ge (R ₁₄₂)(R₁₄₃)(R₁₄₄),

A group represented by (R ₁₄₅)(R₁₄₆),

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

A group represented by the following general formula (3), a broken line of U1

Is bonded to ring B1 to form a substituted or unsubstituted monocyclic ring,

Is bonded to the ring B1 to form a substituted or unsubstituted condensed ring,

Is bonded to the ring C1 to form a substituted or unsubstituted condensed ring,

U1 is

An oxygen atom,

A sulfur atom,

N (R ₁₁₁), or

B(R₁₁₂),

V1 is N (R ₁₁₃),

B (R ₁₁₄), or

C(=O),

U1 and V1 are different from each other,

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

Where there are plural R ₁₄₆, plural R ₁₄₆ are the same or different from each other,

In the general formula (3) described above,

Dashed line of U2

Is bonded to ring A1 to form a substituted or unsubstituted monocyclic ring,

Is bonded to the ring A1 to form a substituted or unsubstituted condensed ring,

Is bonded to the ring B1 to form a substituted or unsubstituted condensed ring, U2 is an oxygen atom,

A sulfur atom,

N (R ₁₂₁), or

B(R₁₂₂),

V2 is N (R ₁₂₃),

B (R ₁₂₄), or

C(=O),

U2 and V2 are different from each other,

R ₁₂₁～R₁₂₄ are each independently a hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

U1 in the general formula (1) and U2 in the general formula (3) are the same or different from each other, V1 in the general formula (1) and V2 in the general formula (3) are the same or different from each other, and V represents a bonding position with X in the general formula (1).

2. The compound according to claim 1, wherein,

The compound represented by the general formula (1) is represented by the following general formula (110), the following general formula (120) or the following general formula (130),

In the general formula (110) described above,

The ring A1 and the ring B1 are each independently the same as the ring A1 and the ring B1 in the general formula (1),

X has the same meaning as X in the general formula (1),

V1 has the same meaning as V1 in the general formula (1),

U1 has the same meaning as U1 in the general formula (1),

U1 and V1 are different from each other,

Is not bonded with each other and is not bonded with each other,

R ₁～R₃ which does not form the substituted or unsubstituted monocyclic ring and which does not form the substituted or unsubstituted condensed ring are each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

A group represented by-N (R ₁₃₁₎(R₁₃₂),

A group represented by Si (R ₁₃₃)(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Halogen atom,

Cyano group,

A group represented by (R ₁₄₅)(R₁₄₆),

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

In the general formula (120) described above,

Ring A1 and ring C1 are each independently the same as the ring A1 and ring C1 in the general formula (1),

X has the same meaning as X in the general formula (1),

V1 has the same meaning as V1 in the general formula (1),

U1 has the same meaning as U1 in the general formula (1),

U1 and V1 are different from each other,

R4 and R ₅

Is not bonded with each other and is not bonded with each other,

R4 and R ₅ which do not form the substituted or unsubstituted monocyclic ring and which do not form the substituted or unsubstituted condensed ring are each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

A group represented by-N (R ₁₃₁₎(R₁₃₂),

A group represented by Si (R ₁₃₃)(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Halogen atom,

Cyano group,

A group represented by (R ₁₄₅)(R₁₄₆),

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

In the general formula (130) described above,

The ring B1 has the same meaning as the ring B1 in the general formula (1),

V1 has the same meaning as V1 in the general formula (1),

U1 has the same meaning as U1 in the general formula (1),

V2 has the same meaning as V2 in the general formula (3),

U2 has the same meaning as U2 in the general formula (3),

Is not bonded with each other and is not bonded with each other,

R ₁～R₃ which does not form the substituted or unsubstituted monocyclic ring and which does not form the substituted or unsubstituted condensed ring are each independently the same as R ₁～R₃ in the general formula (110),

Is not bonded with each other and is not bonded with each other,

R ₆～R₈ which does not form the substituted or unsubstituted monocyclic ring and which does not form the substituted or unsubstituted condensed ring are each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

A group represented by-N (R ₁₃₁)(R₁₃₂),

A group represented by Si (R ₁₃₃)(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Halogen atom,

Cyano group,

A group represented by (R ₁₄₅)(R₁₄₆),

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

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

3. The compound according to claim 2, wherein,

R ₁ in the compound represented by the general formula (110) is not bonded to the ring A1.

4. The compound according to claim 2, wherein,

R ₄ in the compound shown in the general formula (120) is a hydrogen atom.

5. The compound according to claim 2, wherein,

R ₁ in the compound represented by the general formula (130) is not bonded to R ₈.

6. The compound according to claim 2, wherein,

The compound represented by the general formula (110) is represented by the following general formula (110A),

The compound represented by the general formula (130) is represented by the following general formula (130A),

In the general formula (110A) described above,

Ring A1 has the same meaning as ring A1 in the general formula (110),

X has the same meaning as X in the general formula (110),

V1 has the same meaning as V1 in the general formula (110),

U1 has the same meaning as U1 in the general formula (110),

U1 and V1 are different from each other,

R ₁、R₂ and R ₃ are each independently of the other the same meaning as R ₁、R₂ and R ₃ in the general formula (110), R ₁ is not bonded to the ring A1,

In the general formula (130A) described above,

V1 and U1 have the same meaning as V1 and U1 in the general formula (130),

V2 and U2 have the same meaning as V2 and U2 in the general formula (130),

U1 and V1 are different from each other,

U2 and V2 are different from each other,

R ₁、R₂、R₃、R₆、R₇ and R ₈ are each independently identical to the meaning of R ₁、R₂、R₃、R₆、R₇ and R ₈ in the general formula (130),

R ₁ and R ₈ are not bonded to each other,

In the general formula (110A) and the general formula (130A),

Is not bonded with each other and is not bonded with each other,

R ₉、R₁₀ and R ₁₁ which do not form the substituted or unsubstituted monocyclic ring and which do not form the substituted or unsubstituted condensed ring are each independently

Hydrogen atom

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

A group represented by-N (R ₁₃₁)(R₁₃₂),

A group represented by Si (R ₁₃₃)(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Halogen atom,

Cyano group,

A group represented by (R ₁₄₅)(R₁₄₆),

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

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

7. The compound according to claim 6, wherein,

The compound represented by the general formula (110A) is represented by the following general formula (111A),

In the general formula (111A) described above,

Ring A1 has the same meaning as ring A1 in the general formula (110A),

X has the same meaning as X in the general formula (110A),

R ₁、R₂、R₃、R₉、R₁₀ and R ₁₁ each independently have the same meaning as R ₁、R₂、R₃、R₉、R₁₀ and R ₁₁ in the general formula (110A),

Group consisting of R ₁₂ and R ₁₃

Is not bonded with each other and is not bonded with each other,

R ₁₂ which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring is

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

Is not bonded with each other and is not bonded with each other,

R ₁₃、R₁₄、R₁₅、R₁₆ and R ₁₇ which do not form the substituted or unsubstituted monocyclic ring and which do not form the substituted or unsubstituted condensed ring are each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

A group represented by-N (R ₁₃₁)(R₁₃₂),

A group represented by Si (R ₁₃₃)(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Halogen atom,

Cyano group,

A group represented by (R ₁₄₅)(R₁₄₆),

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

Wherein at least any one of R ₁₃ and R ₁₇ which do not form a ring is a group other than a hydrogen atom and a halogen atom.

8. The compound according to claim 7, wherein,

The compound represented by the general formula (110A) is represented by the following general formula (111B),

In the general formula (111B) described above,

Ring A1 has the same meaning as ring A1 in the general formula (110A),

X has the same meaning as X in the general formula (110A),

Is not bonded with each other and is not bonded with each other,

R ₁₃ is bonded to R ₂₈ by a single bond or is not bonded to R ₂₈,

R ₁₃、R₁₄、R₁₅、R₁₆、R₁₇、R₂₄、R₂₅、R₂₆、R₂₇ and R ₂₈ which do not form the substituted or unsubstituted monocyclic ring and which do not form the substituted or unsubstituted condensed ring are each independently

Hydrogen atom

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

A group represented by-N (R ₁₃₁)(R₁₃₂),

A group represented by Si (R ₁₃₃)(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Halogen atom,

Cyano group,

A group represented by (R ₁₄₅)(R₁₄₆),

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

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

9. The compound according to claim 8, wherein,

In the general formula (111B), R ₁ and R ₃ which do not form a ring are hydrogen atoms.

10. The compound according to claim 6, wherein,

The compound represented by the general formula (130A) is represented by the following general formula (131A),

In the general formula (131A) described above,

R ₁、R₂、R₃、R₆、R₇、R₈、R₉、R₁₀ and R ₁₁ each independently have the same meaning as R ₁、R₂、R₃、R₆、R₇、R₈、R₉、R₁₀ and R ₁₁ in the general formula (130A),

Group consisting of R ₁₂ and R ₁₃

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

Is not bonded with each other and is not bonded with each other,

Group consisting of R ₂₃ and R ₂₂

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

Is not bonded with each other and is not bonded with each other,

R ₁₂ and R2 ₃ which do not form the substituted or unsubstituted monocyclic ring and which do not form the substituted or unsubstituted condensed ring are each independently

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

R ₁₃、R₁₄、R₁₅、R₁₆ and R ₁₇ which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring, and R ₁₈、R₁₉、R2₀、R2₁ and R2 ₂ which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are each independently

Hydrogen atom

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted haloalkyl having 1 to 50 carbon atoms,

A group represented by-N (R ₁₃₁)(R1₃₂),

A group represented by Si (R ₁₃₃)(R₁₃₄)(R₁₃₅),

A group represented by-O- (R ₁₃₆),

A group represented by S- (R ₁₃₇),

Halogen atom,

Cyano group,

A group represented by (R ₁₄₅)(R₁₄₆),

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

Wherein at least any one of R ₁₃ and R ₁₇ which do not form a ring is a group other than a hydrogen atom and a halogen atom, and at least any one of R ₁₈ and R2 ₂ is a group other than a hydrogen atom and a halogen atom.

11. The compound according to claim 8, wherein,

The compound represented by the general formula (111B) is represented by the following general formula (111C), general formula (111D), general formula (111E), general formula (111F), general formula (111G), general formula (111H), general formula (111J) or general formula (111K),

In the general formula (111C), the general formula (111D), the general formula (111E), the general formula (111F), the general formula (111G), the general formula (111H), the general formula (111J) and the general formula (111K),

X is

An oxygen atom,

A sulfur atom,

N(R₁₀₁)、

Si (R ₁₀₂)(R₁₀₃), or

C(R₁₀₄)(R₁₀₅),

Y is

An oxygen atom,

A sulfur atom,

N(R₁₀₆)、

Si (R ₁₀₇)(R₁₀₈), or

C(R₁₀₉)(R₁₁₀),

R ₁₀₂～R₁₀₅ in X and R ₁₀₇～R₁₁₀ in Y each independently have the same meaning as R ₁₀₂～R₁₀₅ in the general formula (1),

R ₁₀₆ are each independently

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

R ₁～R₃ and R ₉～R₁₁ each independently have the same meaning as R ₁～R₃ and R ₉～R₁₁ in the general formula (111B),

R ₁₃、R₁₄、R₁₅、R₁₆ and R ₁₇ each independently have the same meaning as R ₁₃、R₁₄、R₁₅、R₁₆ and R ₁₇ in the general formula (111B),

R ₁₃ is not bonded to R ₂₈,

R ₂₄、R₂₅、R₂₆、R₂₇ and R ₂₈ each independently have the same meaning as R ₂₄、R₂₅、R₂₆、R₂₇ and R ₂₈ in the general formula (111B),

Is not bonded with each other and is not bonded with each other,

R2 ₉、R₃₀、R₃₁ and R ₃₂ which 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 the meanings of R ₁, R2 and R ₃ in the general formula (111B),

Is not bonded with each other and is not bonded with each other,

R ₃₃、R₃₄、R₃₅ and R ₃₆ which 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 ₁, R2 and R ₃ which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring in the general formula (111B),

R ₃₇ and R ₃₈ are each independently the same as R ₁、R₂ and R ₃ in the general formula (111B) which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring,

Group consisting of R ₅₀ and R ₅₁

Is not bonded with each other and is not bonded with each other,

R ₅₀ and R ₅₁ which do not form the substituted or unsubstituted monocyclic ring and which do not form the substituted or unsubstituted condensed ring are each independently

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

Group consisting of R ₆₀ and R ₆₁

Is not bonded with each other and is not bonded with each other,

R ₆₀ and R ₆₁ which do not form the substituted or unsubstituted monocyclic ring and which do not form the substituted or unsubstituted condensed ring are each independently

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

R ₁₀₁ is represented by the following general formula (1116),

In the general formula (1116) described above,

R ₃₉、R₄₀、R₄₁、R₄₂ and R ₄₃ each independently have the same meaning as R ₁、R₂ and R ₃ in the general formula (111B),

*61 Represents a bonding position to a nitrogen atom of N (R ₁₀₁) in the general formula (111C) or the general formula (111D).

12. The compound according to claim 11, wherein,

In the general formula (111C), R ₁、R₃、R₉、R₁₁ and R ₃₂ which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are hydrogen atoms,

In the general formula (111D), R ₁、R₃、R₉ and R ₁₁ which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are hydrogen atoms,

In the general formula (111E), R ₁、R₃、R₉、R₁₁ and R ₃₂ which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are hydrogen atoms,

In the general formula (111F), R ₁、R₃、R₉ and R ₃₂ which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are hydrogen atoms,

In the general formula (111G), R ₁、R₃ and R ₉ which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are hydrogen atoms,

In the general formula (111H), R ₁、R₃、R₉、R₁₁ and R ₃₂ which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are hydrogen atoms,

In the general formula (111J), R ₁、R₃、R₉ and R ₃₂ which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are hydrogen atoms,

In the general formula (111K), R ₁、R₃ and R ₉ which do not form the substituted or unsubstituted monocyclic ring and do not form the substituted or unsubstituted condensed ring are hydrogen atoms.

13. The compound according to claim 11 or 12, wherein,

The compound represented by the general formula (111C) is represented by the following general formula (111C-1),

The compound represented by the general formula (111D) is represented by the following general formula (111D-1),

In the general formula (11C-1),

X is

Oxygen atom, or

N(R₁₀₁),

R ₁、R₃、R₉、R₁₁ and R ₃₂ are hydrogen atoms,

R ₂、R₁₀、R₁₃～R₁₇、R₂₄～R₂₈、R₂₉～R₃₁ each independently has the same meaning as R ₂、R₁₀、R₁₃～R₁₇、R₂₄～R₂₈、R₂₉～R₃₁ in the general formula (111C),

In the general formula (11 1D-1),

X is

Oxygen atom, or

N(R₁₀₁),

Y is

Oxygen atom, or

A sulfur atom is used as a source of oxygen,

R ₉ and R ₁₁ are hydrogen atoms,

R ₁～R₃、R₁₀、R₁₃～R₁₇、R₂₄～R₂₈、R₃₃～R₃₆ each independently has the same meaning as R ₁～R₃、R₁₀、R₁₃～R₁₇、R₂₄～R₂₈、R₃₃～R₃₆ in the general formula (111D),

R ₁₀₁ is represented by the following general formula (1116),

In the general formula (1116) described above,

R ₃₉～R₄₃ is each independently the same as R ₁、R₂ and R ₃ in the general formula (111B),

*61 Represents a bonding position to a nitrogen atom of N (R ₁₀₁) in the general formula (111C-1) or the general formula (111D-1).

14. A material for an organic electroluminescent element, comprising the compound according to any one of claims 1 to 13.

15. An organic electroluminescent element having a cathode, an anode, and an organic layer contained between the cathode and the anode,

At least 1 layer of the organic layer contains the compound according to any one of claims 1 to 13 as a first compound.

16. The organic electroluminescent element according to claim 15, wherein,

The organic layer comprises a light-emitting layer,

The light-emitting layer contains the first compound.

17. The organic electroluminescent element according to claim 16, wherein,

The light-emitting layer contains a second compound represented by the following general formula (H10),

In the general formula (H10) described above,

Is not bonded with each other and is not bonded with each other,

R ₁₀₁～R₁₁₀ which does not form the substituted or unsubstituted monocyclic ring and which does not form the substituted or unsubstituted condensed ring are each independently

A hydrogen atom,

Substituent R, or

A group represented by the following general formula (H1 1),

Wherein at least 1 of R ₁₀₁～R₁₁₀ which does not form the substituted or unsubstituted monocyclic ring and does not form the substituted or unsubstituted condensed ring is a group represented by the following general formula (H11),

When there are 2 or more groups of the following general formula (H11), 2 or more groups of the following general formula (H11) are the same or different from each other,

-L₁₀₁-Ar₁₀₁ (H11)

In the general formula (H1 1) described above,

L ₁₀₁ is

A single bond,

Substituted or unsubstituted arylene group having 6 to 50 ring members, or

Ar10 ₁ is

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

The substituent R is

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,

Substituted or unsubstituted alkynyl having 2 to 50 carbon atoms,

A group represented by Si (R ₉₀₁)(R₉₀₂)(R₉₀₃),

A group represented by-O- (R ₉₀₄),

A group represented by S- (R ₉₀₅),

A group represented by-N (R ₉₀₆)(R₉₀₇),

Halogen atom, cyano group, nitro group,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

In the case where there are 2 or more of the substituents R, 2 or more of the substituents R are the same or different from each other,

R ₉₀₁～R₉₀₇ are each independently

A hydrogen atom,

Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,

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

A substituted or unsubstituted heterocyclic group having 5 to 50 ring members,

18. An electronic device in which the organic electroluminescent element according to any one of claims 15 to 17 is mounted.