JP2019165102A - Organic electroluminescent element and electronic apparatus - Google Patents

Abstract

An organic electroluminescent element that emits light with high efficiency and an electronic device equipped with the organic EL element are provided. An anode, a second organic layer, a first organic layer, and a cathode are provided in this order, the first organic layer includes a first compound and a second compound, and the second organic layer is a third organic layer. An organic EL device comprising a compound, wherein the first compound is a compound represented by a specific formula, the second compound is a compound having delayed fluorescence, and the third compound is a carbazole derivative having a specific structure. [Selection diagram] None

Description

  The present invention relates to an organic electroluminescence element and an electronic device.

When a voltage is applied to an organic electroluminescence element (hereinafter sometimes referred to as “organic EL element”), holes from the anode and electrons from the cathode are injected into the light emitting layer. Then, in the light emitting layer, the injected holes and electrons are recombined to form excitons. At this time, singlet excitons and triplet excitons are generated at a ratio of 25%: 75% according to the statistical rule of electron spin.
Fluorescent organic EL devices that use light emitted from singlet excitons are being applied to full-color displays such as mobile phones and televisions, but the internal quantum efficiency of 25% is said to be the limit. Therefore, studies for improving the performance of the organic EL element are being conducted.

In addition to singlet excitons, it is expected that organic EL elements emit light more efficiently by using triplet excitons. Against this background, highly efficient fluorescent organic EL devices using thermally activated delayed fluorescence (hereinafter sometimes simply referred to as “delayed fluorescence”) have been proposed and studied.
For example, a TADF (Thermally Activated Delayed Fluorescence, heat activated delayed fluorescence) mechanism has been studied. In this TADF mechanism, when a material having a small energy difference (ΔST) between a singlet level and a triplet level is used, a reverse intersystem crossing from a triplet exciton to a singlet exciton is thermally generated. It is a mechanism that utilizes the phenomenon. The thermally activated delayed fluorescence is described in, for example, “Adachi Chiba, edited by“ Physical Properties of Organic Semiconductor Devices ”, Kodansha, published on April 1, 2012, pages 261-268”. An organic EL element using this TADF mechanism is disclosed in Patent Document 2, for example. Patent Document 1 describes a compound similar in structure to the compound disclosed in Patent Document 2.

JP 2006-6033 A International Publication No. 2016/056559

However, in the field of organic EL elements, it is required to further improve the element performance.
The objective of this invention is providing the organic electroluminescent element which light-emits with high efficiency, and providing an electronic device provided with the said organic electroluminescent element.

According to one aspect of the invention,
The anode,
A cathode,
A first organic layer included between the anode and the cathode;
A second organic layer included between the anode and the first organic layer,
The first organic layer includes a first compound and a second compound,
The second organic layer comprises a third compound;
The first compound is a compound represented by the following general formula (1),
The second compound is a delayed fluorescent compound,
The third compound is a compound represented by the following general formula (3).
An organic electroluminescent device is provided.

In the general formula (1),
X is a nitrogen atom or a carbon atom bonded to Y;
Y is a hydrogen atom or a substituent,
R _{21 to} R ₂₆ are each independently a hydrogen atom or a substituent, or a group of R ₂₁ and R _22, a group of R ₂₂ and R _23, a group of R ₂₄ and R ₂₅ , and R ₂₅ and R Any one or more of the ₂₆ groups are joined together to form a ring;
Y as a substituent and R _{21 to} R ₂₆ are each independently
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted C1-C30 halogenated alkoxy group,
A substituted or unsubstituted alkylthio group having 6 to 30 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,
A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,
A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,
Halogen atoms,
A carboxy group,
A substituted or unsubstituted ester group,
A substituted or unsubstituted carbamoyl group,
A substituted or unsubstituted amino group,
Nitro group,
A cyano group,
Selected from the group consisting of a substituted or unsubstituted silyl group, and a substituted or unsubstituted siloxanyl group,
Z ₂₁ and Z ₂₂ are each independently a substituent, or Z ₂₁ and Z ₂₂ are bonded to each other to form a ring,
Z ₂₁ and Z ₂₂ as substituents are each independently
Halogen atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
It is selected from the group consisting of a substituted or unsubstituted halogenated alkoxy group having 1 to 30 carbon atoms and a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.

In the general formula (3),
n is 1, 2, 3, or 4;
when n is 2, 3, or 4, the plurality of Cz are the same or different from each other;
X _B is a group represented by the following general formula (3A),
Cz is a group represented by the following general formula (3B-1) or (3B-2).

In the general formula (3A),
Ar ₁ is
Monovalent or polyvalent residues derived from substituted or unsubstituted dibenzofurans,
Monovalent or polyvalent residues derived from substituted or unsubstituted azadibenzofuran,
A monovalent or polyvalent residue derived from substituted or unsubstituted dibenzothiophene, or a monovalent or polyvalent residue derived from substituted or unsubstituted azadibenzothiophene,
Ar ₂ is independently
A monovalent or polyvalent residue derived from a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms,
Monovalent or polyvalent residues derived from substituted or unsubstituted dibenzofurans,
Monovalent or polyvalent residues derived from substituted or unsubstituted azadibenzofuran,
A monovalent or polyvalent residue derived from substituted or unsubstituted dibenzothiophene, or a monovalent or polyvalent residue derived from substituted or unsubstituted azadibenzothiophene,
k is 0, 1, 2, 3, or 4;
when k is 2, 3, or 4, the plurality of Ar ₂ are the same or different from each other;
In the case where Ar ₁ has a substituent, the substituent D 1 is independently
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,
A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted C1-C30 halogenated alkoxy group,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted silyl group,
Halogen atoms,
Selected from the group consisting of a cyano group and a nitro group,
The substituent D2 in the case where Ar ₂ has a substituent has the same meaning as the substituent D1,
When n is 1, Cz binds to Ar ₁
When n is 2, 3, or 4, a plurality of Cz are each independently bonded to Ar ₁ or bonded to Ar ₂ . However, at least one Cz is bonded to Ar ₁ .

In the general formula (3B-1),
X _{1 to} X ₈ are each independently a nitrogen atom or CR _A ,
R _A is a hydrogen atom or a substituent, or any one or more of the groups of adjacent R _A are bonded to each other to form a ring,
R _A as a substituent is each independently
A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted silyl group,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted C1-C30 halogenated alkoxy group,
A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,
Halogen atoms,
A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,
A cyano group,
A hydroxy group,
Selected from the group consisting of a nitro group and a carboxy group;
The plurality of R _A are the same or different from each other,
However, the nitrogen atom in the general formula (3B-1) is bonded to either Ar ₁ or Ar _{2 in} the general formula (3A).

In the general formula (3B-2),
Or X ₁ to X ₄ are the general formula (3A) in the carbon atom bonded to the one of Ar ₁ and Ar _2, a nitrogen atom or a CR _{C, R C} is a hydrogen atom or a substituent, or bonded to any one or more sets of pairs of _{R C} adjacent to each other to form a ring, provided _that one of X 1 to X ₄ are in the general formula (3A), Ar ₁ and Ar ₂ is a carbon atom bonded to any one of
X ₅ to X ₈ is a nitrogen atom or a CR _D, R _D is a hydrogen atom or a substituent, or adjacent R _D any one or more sets of pairs of mutually bonded each other to form a ring Form the
R _B , R _C and R _D are each independently synonymous with R _A in the general formula (3B-1), and the plurality of R _C are the same as or different from each other, and the plurality of R _D are The same or different,
In the third compound, the substituent E in the case of “substituted or unsubstituted” is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted C1-C30 halogenated alkoxy group,
A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,
A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,
Halogen atoms,
A carboxy group,
A substituted or unsubstituted amino group,
Nitro group,
A cyano group,
A substituted or unsubstituted silyl group,
A substituent selected from the group consisting of a substituted phosphoryl group and a hydroxy group;
When the substituent E further has a substituent F, the substituent F is
An unsubstituted aryl group having 6 to 30 ring carbon atoms,
An unsubstituted heteroaryl group having 5 to 30 ring atoms;
An unsubstituted alkyl group having 1 to 30 carbon atoms,
An unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
An unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
Unsubstituted silyl group,
An unsubstituted alkoxy group having 1 to 30 carbon atoms,
An unsubstituted halogenated alkoxy group having 1 to 30 carbon atoms,
An unsubstituted aryloxy group having 6 to 30 carbon atoms,
An unsubstituted alkylthio group having 1 to 30 carbon atoms,
An unsubstituted arylthio group having 6 to 30 ring carbon atoms,
An unsubstituted aralkyl group having 7 to 30 carbon atoms,
An unsubstituted alkenyl group having 2 to 30 carbon atoms,
Halogen atoms,
An unsubstituted alkynyl group having 2 to 30 carbon atoms,
A cyano group,
A hydroxy group,
Selected from the group consisting of a nitro group and a carboxy group, provided that substituent F has no further substituents.

  According to one embodiment of the present invention, there is provided an electronic device on which the organic electroluminescence element according to one embodiment of the present invention described above is mounted.

  According to one embodiment of the present invention, an organic electroluminescence element that emits light with high efficiency and an electronic device including the organic electroluminescence element can be provided.

It is a figure which shows schematic structure of an example of the organic electroluminescent element which concerns on one Embodiment. It is the schematic of the apparatus which measures transient PL. It is a figure which shows an example of the attenuation curve of transient PL. It is a figure which shows the relationship of the energy level and energy transfer of the 1st compound in a 1st organic layer (light emitting layer), and a 2nd compound. It is a figure which shows the relationship of the energy level and energy transfer of the 1st compound in a 1st organic layer (light emitting layer), a 2nd compound, and a 4th compound.

[First embodiment]
The configuration of the organic EL element according to the first embodiment of the present invention will be described.
The organic EL element includes an organic layer between both an anode and a cathode. This organic layer is formed by laminating a plurality of layers composed of organic compounds. The organic layer may further contain an inorganic compound. The organic EL element of this embodiment has a first organic layer included between the anode and the cathode, and a second organic layer included between the anode and the first organic layer.
The first organic layer is preferably a light emitting layer. The second organic layer is not particularly limited as long as it is a layer that can be included between the anode and the first organic layer. For example, any one of a hole injection layer, a hole transport layer, and an electron barrier layer is used. A layer is preferred.
In the organic EL device of the present embodiment, the first organic layer is a light emitting layer, and the second organic layer is an electron barrier layer.
The second organic layer is preferably disposed in contact with the first organic layer. That is, the electron barrier layer is preferably disposed in contact with the light emitting layer on the anode side of the light emitting layer.
The organic layer may be composed of only the first organic layer and the second organic layer, for example. Further, the organic layer is at least any selected from the group consisting of layers employed in organic EL elements, for example, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, a hole barrier layer, and the like. It may further have such a layer.

In FIG. 1, schematic structure of an example of the organic EL element in this embodiment is shown.
The organic EL element 1 includes a translucent 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 includes, in order from the anode 3 side, a hole injection layer 6, a hole transport layer 7, an electron barrier layer 11 as a second organic layer, a light emitting layer 5 as a first organic layer, and an electron transport layer 8. , And the electron injection layer 9 are laminated in this order.

In the organic EL element 1 of the present embodiment, the light emitting layer 5 includes a first compound and a second compound.
The first compound is a compound represented by the general formula (1), and the second compound is a delayed fluorescent compound.
The light emitting layer 5 may contain a metal complex.
It is preferable that the light emitting layer 5 does not contain a phosphorescent metal complex. Moreover, it is preferable that the light emitting layer 5 does not contain a metal complex.
The first compound is preferably a dopant material (sometimes referred to as guest material, emitter, or luminescent material), and the second compound is a host material (sometimes referred to as matrix material). It is preferable.
In the present embodiment, the electron barrier layer 11 contains the compound represented by the general formula (3).

The inventors include a first compound (a compound represented by the general formula (1)) and a second compound having delayed fluorescence in the first organic layer, and further includes a second organic layer. It has been found that when a third compound (compound represented by the general formula (3)) is included in the layer, light is emitted with high efficiency.
The present inventors, as the third compound, have a specific skeleton (hereinafter referred to as a carbazolyl group) and a condensed heteroaryl group (preferably a tricyclic condensed heteroaryl group) in which the hetero atom is an oxygen atom or a sulfur atom. , Which may be referred to as “specific Cz-dibenzo skeleton”). In this embodiment, the compound having this specific Cz-dibenzo skeleton is a second organic layer (an electron barrier layer in this embodiment) between the anode and the first organic layer (a light emitting layer in this embodiment). It is presumed that the amount of holes supplied to the first organic layer is suppressed, the carrier balance factor in the first organic layer is improved, and as a result, the device is easily made highly efficient.
In particular, since a compound having a specific Cz-dibenzo skeleton (third compound) tends to have a large ionization potential (Ip), the third compound having such characteristics is used as the second organic layer. It is considered that the effect of suppressing the amount of hole supply to the first organic layer is remarkably exhibited.
Therefore, according to the present embodiment, an organic EL element that emits light with high efficiency is realized.

  Hereinafter, the configuration of the organic EL element of the present embodiment will be described in detail. Hereinafter, description of a code | symbol is abbreviate | omitted.

<First organic layer>
The first organic layer (in the present embodiment, the light emitting layer) includes a first compound and a second compound.

(First compound)
The first compound is a compound represented by the following general formula (1).
The first compound is preferably a compound having fluorescence.

In the general formula (1),
X is a nitrogen atom or a carbon atom bonded to Y;
Y is a hydrogen atom or a substituent,
R _{21 to} R ₂₆ are each independently a hydrogen atom or a substituent, or a group of R ₂₁ and R _22, a group of R ₂₂ and R _23, a group of R ₂₄ and R ₂₅ , and R ₂₅ and R Any one or more of the ₂₆ groups are joined together to form a ring;
Y as a substituent and R _{21 to} R ₂₆ are each independently
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted C1-C30 halogenated alkoxy group,
A substituted or unsubstituted alkylthio group having 6 to 30 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,
A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,
A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,
Halogen atoms,
A carboxy group,
A substituted or unsubstituted ester group,
A substituted or unsubstituted carbamoyl group,
A substituted or unsubstituted amino group,
Nitro group,
A cyano group,
Selected from the group consisting of a substituted or unsubstituted silyl group, and a substituted or unsubstituted siloxanyl group,
Z ₂₁ and Z ₂₂ are each independently a substituent, or Z ₂₁ and Z ₂₂ are bonded to each other to form a ring,
Z ₂₁ and Z ₂₂ as substituents are each independently
Halogen atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted C1-C30 halogenated alkoxy group,
And a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms.

In the general formula (1), for example, when the group of R ₂₅ and R ₂₆ is bonded to each other to form a ring, the first compound is represented by the following general formula (11).

In the general formula (11), X, Y, R _{21 to} R ₂₄ , Z ₂₁ , and Z ₂₂ are X, Y, R _{21 to} R ₂₄ , Z ₂₁ , and Z in the general formula (1), respectively. ₂₂ , R _{27 to} R ₃₀ are each independently a hydrogen atom or a substituent, and R _{21 to} R ₃₀ are listed as R _{21 to} R ₂₄ as substituents when R _{27 to} R ₃₀ are substituents. It is synonymous with a substituent.

In the general formula (1), when Z ₂₁ and Z ₂₂ are bonded to each other to form a ring, the first compound is represented by, for example, the following general formula (1A) or the following general formula (1B). Is done. However, the first compound is not limited to the following structure.

In the general formula (1A), X, Y, and R _{21 to} R ₂₆ are respectively synonymous with X, Y, and R _{21 to} R ₂₆ in the general formula (1), and R _1A is independently selected. In addition, the substituent when R _1A is a substituent is the same as the substituents listed for R _{21 to} R ₂₆ , and n3 is 2.
In the general formula (1B), X, Y, and R _{21 to} R ₂₆ are respectively synonymous with X, Y, and R _{21 to} R ₂₆ in the general formula (1), and R _1B is independently selected. In addition, the substituent when R _1B is a substituent is the same as the substituents listed for R _{21 to} R ₂₆ , and n4 is 4.

At least one of Z ₂₁ and _{Z 22} (preferably _{Z 21} and _{Z 22)} is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms Substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted halogenated alkoxy group having 1 to 30 carbon atoms, and substituted or It is preferably a group selected from the group consisting of unsubstituted aryloxy groups having 6 to 30 ring carbon atoms.
At least one of Z ₂₁ and Z ₂₂ is an alkoxy group having 1 to 30 carbon atoms substituted with a fluorine atom, an aryloxy group having 6 to 30 ring carbon atoms substituted with a fluorine atom, and 1 to 1 carbon atoms. It is more preferably a group selected from the group consisting of aryloxy groups having 6 to 30 ring carbon atoms substituted with 30 fluoroalkyl groups.
At least one of Z ₂₁ and Z ₂₂ is more preferably a C 1-30 alkoxy group substituted with a fluorine atom, and Z ₂₁ and Z ₂₂ are substituted with a fluorine atom. More preferably, it is an alkoxy group.

It is also preferred that Z ₂₁ and Z ₂₂ are the same.

On the other hand, it is also preferably at least one is a fluorine atom in the Z ₂₁ and the Z _22, it is also more preferable that the Z ₂₁ and the Z ₂₂ is a fluorine atom.

It is also preferable that at least one of Z ₂₁ and Z ₂₂ is a group represented by the following general formula (1a).

In the general formula (1a), A represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted halogenated alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming carbon. An aryl group having 6 to 12 carbon atoms, L ₂ is a substituted or unsubstituted alkylene group having 1 to 6 carbon atoms, or a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms, m is When 0, 1, 2, 3, 4, 5, 6, or 7 and m is 2, 3, 4, 5, 6, or 7, the plurality of L ₂ are the same or different from each other. m is preferably 0, 1, or 2. When m is 0, A is directly bonded to O (oxygen atom).

In the general formula (1), when Z ₂₁ and Z ₂₂ are groups represented by the general formula (1a), the first compound is a compound represented by the following general formula (10).
The first compound is also preferably a compound represented by the following general formula (10).

In the general formula (10), Y and R _{21 to} R ₂₆ when X and X are carbon atoms bonded to Y are respectively X, Y and R _{21 to} R ₂₆ in the general formula (1). It is synonymous. A ₂₁ and A ₂₂ are synonymous with A in the general formula (1a), and may be the same as or different from each other. L ₂₁ and L ₂₂ have the same meaning as L ₂ in the general formula (1a), and may be the same as or different from each other. m1 and m2 are each independently 0, 1, 2, 3, 4, 5, 6, or 7, and preferably 0, 1, or 2. When m1 is 2, 3, 4, 5, 6, or 7, the plurality of L ₂₁ are the same or different from each other, and when m2 is 2, 3, 4, 5, 6, or 7, the plurality of L _{21 22} are the same as or different from each other. When m1 is 0, A ₂₁ is directly bonded to O (oxygen atom), and when m2 is 0, A ₂₂ is directly bonded to O (oxygen atom).

At least one of A and L ₂ in the general formula (1a) is preferably substituted with a halogen atom, and more preferably substituted with a fluorine atom.

  A in the general formula (1a) is more preferably a perfluoroalkyl group having 1 to 6 carbon atoms or a perfluoroaryl group having 6 to 12 ring carbon atoms, and a perfluoroalkyl group having 1 to 6 carbon atoms. More preferably, it is a group.

L ₂ in the general formula (1a) is more preferably a perfluoroalkylene group having 1 to 6 carbon atoms or a perfluoroarylene group having 6 to 12 ring carbon atoms, and perfluoro having 1 to 6 carbon atoms. More preferably, it is an alkylene group.

  That is, the first compound is also preferably a compound represented by the following general formula (10a).

In the general formula (10a),
X is synonymous with X in the general formula (1), and Y when X is a carbon atom bonded to Y is synonymous with Y in the general formula (1);
R _{21 to} R ₂₆ are each independently synonymous with R _{21 to} R ₂₆ in the general formula (1),
m3 is 0 or more and 4 or less,
m4 is 0 or more and 4 or less,
m3 and m4 are the same as or different from each other.

In the general formulas (1), (11), (10), and (10a),
X is a carbon atom bonded to Y;
Y is a hydrogen atom or a substituent,
Y as a substituent is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl halide group having 1 to 30 carbon atoms, and a substituted or unsubstituted ring structure carbon number having 6 to 30 carbon atoms. A substituent selected from the group consisting of aryl groups is preferable, and a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms is more preferable.

In the general formulas (1), (11), (10), and (10a),
As a more preferred embodiment,
X is a carbon atom bonded to Y;
Y is a hydrogen atom or a substituent,
Y as a substituent is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
When Y as a substituent is an aryl group having 6 to 30 ring carbon atoms having a substituent, the substituent is
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
Examples include a substituted or unsubstituted halogenated alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 ring carbon atoms substituted with an alkyl group having 1 to 30 carbon atoms.

In the first compound, Z ₂₁ and Z ₂₂ may be bonded to each other to form a ring, but it is preferable that Z ₂₁ and Z ₂₂ are not bonded to each other to form a ring.

In the general formulas (1), (10), and (10a), at least one of R ₂₁ , R ₂₃ , R ₂₄ , and R ₂₆ is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or It is preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
In the general formulas (1), (10), and (10a), R ₂₁ , R ₂₃ , R ₂₄ , and R ₂₆ are substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, or substituted or unsubstituted A halogenated alkyl group having 1 to 30 carbon atoms is more preferable. In this case, R ₂₂ and R ₂₅ are preferably hydrogen atoms.

In the general formulas (1), (10), and (10a), at least one of R ₂₁ , R ₂₃ , R ₂₄ , and R ₂₆ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. It is preferable that
In the general formulas (1), (10), and (10a), R ₂₁ , R ₂₃ , R ₂₄ , and R ₂₆ may be substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms. preferable. In this case, R ₂₂ and R ₂₅ are preferably hydrogen atoms.

In the general formulas (1), (10), and (10a),
As a more preferred embodiment,
R ₂₁ , R ₂₃ , R ₂₄ , and R ₂₆ are each independently
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms),
6 to 30 ring carbon atoms (preferably ring formation) substituted with a substituted or unsubstituted alkyl halide group having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms) or an alkyl group having 1 to 30 carbon atoms An aryl group having 6 to 12 carbon atoms,
An embodiment in which R ₂₂ and R ₂₅ are hydrogen atoms is exemplified.

In the general formula (11), at least one of R ₂₁ , R ₂₃ , and R ₂₄ is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted halogen having 1 to 30 carbon atoms. An alkyl group is preferable.

In the general formula (11), R ₂₁ , R ₂₃ , and R ₂₄ are substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, or substituted or unsubstituted halogenated alkyl groups having 1 to 30 carbon atoms. It is more preferable. In this case, R ₂₂ is preferably a hydrogen atom.

In the general formula (11), it is preferable that at least one of R ₂₁ , R ₂₃ , and R ₂₄ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

In the general formula (11), R ₂₁ , R ₂₃ , and R ₂₄ are more preferably substituted or unsubstituted aryl groups having 6 to 30 ring carbon atoms. In this case, R ₂₂ is preferably a hydrogen atom.

In the general formula (11),
As a more preferred embodiment,
R ₂₁ , R ₂₃ , and R ₂₄ are each independently
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms),
6 to 30 ring carbon atoms (preferably ring formation) substituted with a substituted or unsubstituted alkyl halide group having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms) or an alkyl group having 1 to 30 carbon atoms An aryl group having 6 to 12 carbon atoms,
An embodiment in which R ₂₂ is a hydrogen atom is exemplified.

  In the first compound, examples of the alkoxy group substituted with a fluorine atom include 2,2,2-trifluoroethoxy group, 2,2-difluoroethoxy group, 2,2,3,3,3. -Pentafluoro-1-propoxy group, 2,2,3,3-tetrafluoro-1-propoxy group, 1,1,1,3,3,3-hexafluoro-2-propoxy group, 2,2,3 , 3,4,4,4-heptafluoro-1-butyloxy group, 2,2,3,3,4,4-hexafluoro-1-butyloxy group, nonafluorotertiary butyloxy group, 2,2,3 , 3,4,4,5,5,5-nonafluoropentanoxy group, 2,2,3,3,4,4,5,5,6,6,6-undecafluorohexanoxy group, 2,3-bis (trifluoromethyl) -2,3-butanedioxy group, , 1,2,2-tetra (trifluoromethyl) ethyleneglycoxy group, 4,4,5,5,6,6,6-heptafluorohexane-1,2-dioxy group, and 4,4,5, 5,6,6,7,7,8,8,9,9,9-tridecafluorononane-1,2-dioxy group and the like.

  In the first compound, the aryloxy group substituted with a fluorine atom or the aryloxy group substituted with a fluoroalkyl group includes, for example, a pentafluorophenoxy group, a 3,4,5-trifluorophenoxy group, 4- Trifluoromethylphenoxy group, 3,5-bistrifluoromethylphenoxy group, 3-fluoro-4-trifluoromethylphenoxy group, 2,3,5,6-tetrafluoro-4-trifluoromethylphenoxy group, 4-fluoro A catecholate group, a 4-trifluoromethyl catecholate group, a 3,5-bistrifluoromethyl catecholate group, etc. are mentioned.

The first compound is preferably a fluorescent compound.
In this case, the first compound preferably emits light having a main peak wavelength of 400 nm to 700 nm.
By using such a fluorescent first compound in the light emitting layer together with the second compound (delayed fluorescent compound), it becomes easy to emit light with high efficiency.
In this specification, the main peak wavelength means that the emission intensity in the measured fluorescence spectrum is maximum for a toluene solution in which the measurement target compound is dissolved at a concentration of 10 ⁻⁶ mol / liter to 10 ⁻⁵ mol / liter. The peak wavelength of the fluorescence spectrum. As a measuring device, a spectrofluorometer (manufactured by Hitachi High-Tech Science Co., Ltd., F-7000) is used.
The first compound preferably exhibits red light emission or green light emission.

In this specification, red light emission refers to light emission having a main peak wavelength of a fluorescence spectrum in the range of 600 nm to 660 nm.
When the first compound is a red fluorescent compound, the main peak wavelength of the first compound is preferably 600 nm to 660 nm, more preferably 600 nm to 640 nm, and still more preferably 610 nm to 630 nm. .

In this specification, green light emission refers to light emission having a main peak wavelength of a fluorescence spectrum in the range of 500 nm to 560 nm.
When the first compound is a green fluorescent compound, the main peak wavelength of the first compound is preferably 500 nm or more and 560 nm or less, more preferably 500 nm or more and 540 nm or less, and further preferably 510 nm or more and 530 nm or less. .

  For example, as one aspect of the organic EL device according to the present embodiment, an anode, a cathode, a first organic layer included between the anode and the cathode, and the anode and the first organic layer A second organic layer included in between, wherein the first organic layer includes a first compound and a second compound, and the second organic layer includes a third compound, The first compound is a compound represented by the general formula (1), and the first compound is a compound having a main peak wavelength in a range of 600 nm to 660 nm, and the second compound Is a delayed fluorescent compound, and the third compound includes an organic EL device which is a compound represented by the general formula (3).

  Further, for example, as another aspect of the organic EL element according to the present embodiment, an anode, a cathode, a first organic layer included between the anode and the cathode, the anode, and the first A second organic layer included between the first organic layer and the second organic layer, the second organic layer including a first compound and a second compound. The first compound is a compound represented by the general formula (1), the first compound is a compound having a main peak wavelength in a range of 500 nm to 560 nm, The second compound is a delayed fluorescent compound, and the third compound includes an organic EL device that is a compound represented by the general formula (3).

  In addition, this invention is not limited to the organic EL element of the aspect quoted here.

-Manufacturing method of a 1st compound A 1st compound can be manufactured by a well-known method.

  Specific examples of the first compound according to this embodiment are shown below. The first compound in the present invention is not limited to these specific examples. Note that in this specification, there are various notation methods for the coordination bond between a boron atom and a nitrogen atom in a pyromethene skeleton, such as a broken line, an arrow, or an omission. In this specification, it represents with a broken line or abbreviate | omits description.

(Second compound)
The second compound is a delayed fluorescent compound.
The second compound according to this embodiment is not a phosphorescent metal complex. Moreover, it is preferable that the 2nd compound which concerns on this embodiment is not a metal complex.

  In the present embodiment, examples of the second compound include compounds represented by the following general formula (2).

In the general formula (2),
A is an acceptor (electron-accepting) site, and is a group having a partial structure selected from the following general formulas (a-1) to (a-7). When a plurality of A are present, the plurality of A may be the same or different from each other, and A may be bonded to each other to form a saturated or unsaturated ring;
B is a donor (electron-donating) moiety and has a partial structure selected from the following general formulas (b-1) to (b-6). When a plurality of B are present, the plurality of B may be the same or different from each other, and B may be bonded to each other to form a saturated or unsaturated ring;
a, b, and d are each independently 1, 2, 3, 4, or 5;
c is 0, 1, 2, 3, 4, or 5;
When c is 0, A and B are bonded by a single bond or a spiro bond,
When c is 1, 2, 3, 4 or 5, L is
A linking group selected from the group consisting of a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms and a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms, wherein L is When there are a plurality of L, the plurality of L may be the same or different from each other, and L may be bonded to each other to form a saturated or unsaturated ring.

In the general formulas (b-1) to (b-6),
R is each independently a hydrogen atom or a substituent, and when R is a substituent, the substituent is
A substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms,
When selected from the group consisting of a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms and a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and a plurality of R are present, the plurality of R are mutually It may be the same or different, and R may be bonded to each other to form a saturated or unsaturated ring.

  Examples of the binding mode of the compound represented by the general formula (2) include the binding modes shown in Table 1 below.

  In the present embodiment, the second compound preferably has a partial structure represented by the following general formula (200) and a partial structure represented by the following general formula (2Y) in one molecule.

In the general formula (200), CN is a cyano group.
n is an integer of 1 or more. n is preferably an integer of 1 or more and 5 or less, and more preferably an integer of 2 or more and 4 or less.
Z _{1 to} Z ₆ are each independently a nitrogen atom, a carbon atom bonded to CN, or a carbon atom bonded to another atom in the molecule of the second compound. For example, when Z ₁ is a carbon atom bonded to CN, at least one of the remaining five (Z _{2 to} Z ₆ ) is a carbon atom bonded to another atom in the molecule of the second compound; Become. The other atom may be an atom constituting a partial structure represented by the following general formula (2Y), or may be an atom constituting a linking group or a substituent intervening with the partial structure.
The second compound according to this embodiment may have a 6-membered ring composed of Z _{1 to} Z ₆ as a partial structure, or a condensation composed of a ring condensed to the 6-membered ring. You may have a ring as a partial structure.

(In the general formula (2Y), F and G each independently represent a ring structure.
m is 0 or 1.
When m is 1, Y ₂₀ represents a single bond, an oxygen atom, a sulfur atom, a selenium atom, a carbon atom, a silicon atom, or a germanium atom. )

  When m is 0 in the general formula (2Y), the general formula (2Y) is represented by the following general formula (20Y).

  The ring structure F and the ring structure G in the general formula (20Y) have the same meaning as the ring structure F and the ring structure G in the general formula (2Y).

  In the general formula (2Y), when m is 1, the general formula (2Y) is represented by any one of the following general formulas (22) to (28).

  The ring structure F and the ring structure G in the general formulas (22) to (28) have the same meaning as the ring structure F and the ring structure G in the general formula (2Y).

  In the present embodiment, the ring structure F and the ring structure G are preferably a 5-membered ring or a 6-membered ring, and the 5-membered ring or 6-membered ring is preferably an unsaturated ring, More preferably, it is a member ring.

  The second compound according to this embodiment is preferably a compound represented by the following general formula (20).

In the general formula (20),
A is represented by the general formula (200). However, in the general formula (200), CN is a cyano group, n is an integer of 1 or more, and Z _{1 to} Z ₆ are independent of each other. Are a carbon atom bonded to CN, a carbon atom bonded to CN, a carbon atom bonded to R, a carbon atom bonded to L, or a carbon atom bonded to D, and a carbon atom bonded to CN among Z _{1 to} Z ₆ And at least one carbon atom bonded to L or D,
Each R is independently a hydrogen atom or a substituent. The substituent in R is a halogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted ring formation. Aromatic heterocyclic group having 5 to 30 atoms, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, substituted or unsubstituted ring forming carbon number 6-60 arylsilyl groups, substituted or unsubstituted alkoxy groups having 1 to 30 carbon atoms, substituted or unsubstituted aryloxy groups having 6 to 30 ring carbon atoms, substituted or unsubstituted 2 to 30 carbon atoms Alkylamino group, substituted or unsubstituted arylamino group having 6 to 60 ring carbon atoms, substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, and substituted or unsubstituted It is a substituent selected from the group consisting of ring-forming arylthio group having 6 to 30 carbon atoms.

In the general formula (20), D is represented by the general formula (2Y), provided that the ring structure F and the ring structure G in the general formula (2Y) may be unsubstituted or have a substituent. Well, m is 0 or 1, and when m is 1, Y ₂₀ is a single bond, oxygen atom, sulfur atom, selenium atom, carbonyl group, CR ₂₁ R ₂₂ , SiR ₂₃ R ₂₄ or GeR _25. represents _{R 26,} R 21 ~R ₂₆ is synonymous with the groups mentioned in the R. In the general formula (2Y), when m is 1, the general formula (2Y) is represented by any one of the general formulas (22) to (25) and the following general formulas (21Y) to (24Y). Is done.

In the general formula (20),
(I) When L is interposed between A and D,
L is a single bond, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 14 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 14 ring atoms, CR ₈₁ R ₈₂ , NR _{83, O, S, SiR 84} R 85, CR 86 R 87 -CR 88 R 89, CR 90 = CR 91, a substituted or unsubstituted aliphatic hydrocarbon ring group or a substituted or unsubstituted aliphatic heterocyclic group, And
R _{81 to} R ₉₁ each independently have the same meaning as R.
In the general formula (20),
(Ii) when L is located at the end in the molecule of the second compound;
L is synonymous with R.

In the general formula (20),
f is an integer of 1 or more,
e and g are each independently an integer of 0 or more.
Several A may mutually be same or different.
Several D may mutually be same or different.
Several L may mutually be same or different.

  The general formula (20) is represented by the following general formulas (201) to (220), for example.

  In the general formula (20), in the repeating unit enclosed in parentheses having the repeating number f, D may be bonded to A via L, or via L to D. A may be bonded. For example, you may branch like the following general formula (221)-(228).

The second compound according to this embodiment is not limited to the compounds represented by the general formulas (201) to (228). When L is omitted in the general formulas (201) to (228), L is a single bond interposed between A and D, or L is in the molecule of the second compound. Indicates a hydrogen atom located at the end.
For the purpose of keeping ΔST of one molecule small, it is preferable that L is not a condensed aromatic ring in terms of molecular design, but a condensed aromatic ring is also employed as long as thermally active delayed fluorescence can be obtained. Can do. Moreover, since the molecular design which arrange | positions A and D correctly in 1 molecule is needed, it is preferable that the 2nd compound which concerns on this embodiment is a low molecular material. Therefore, the second compound according to this embodiment preferably has a molecular weight of 5000 or less, and more preferably a molecular weight of 3000 or less. It is preferable that the 2nd compound which concerns on this embodiment contains the partial structure of the said General formula (200) and the said General formula (2Y).
The organic EL element containing the second compound emits light using a thermally activated delayed fluorescence mechanism.

  In the present embodiment, the general formula (2Y) is preferably represented by at least one of the following general formula (2a) and the following general formula (2x).

  In the general formula (2x), A and B each independently represent a ring structure represented by the following general formula (2c) or a ring structure represented by the following general formula (2d), The ring structure B is condensed with an adjacent ring structure at an arbitrary position. px and py are each independently an integer of 0 or more and 4 or less, and represent the numbers of the ring structure A and the ring structure B, respectively. When px is an integer of 2 or more and 4 or less, the plurality of ring structures A may be the same as or different from each other. When py is an integer of 2 or more and 4 or less, the plurality of ring structures B may be the same as or different from each other. Therefore, for example, when px is 2, the ring structure A may have two ring structures represented by the following general formula (2c) or two ring structures represented by the following general formula (2d). Alternatively, a combination of one ring structure represented by the following general formula (2c) and one ring structure represented by the following general formula (2d) may be used.

In the general formula (2d), Z ₇ represents a carbon atom, a nitrogen atom, a sulfur atom, or an oxygen atom.

  In the general formula (2x), when px is 0 and c is py, it is represented by the following general formula (2b).

  In the general formula (2b), c is an integer of 1 or more and 4 or less. When c is an integer of 2 or more and 4 or less, the plurality of ring structures E may be the same as or different from each other. In the general formula (2b), E represents a ring structure represented by the general formula (2c) or a ring structure represented by the general formula (2d), and the ring structure E represents an adjacent ring structure and Condensation at any position. Therefore, for example, when c is 2, the two ring structures E may have two ring structures represented by the general formula (2c) or two ring structures represented by the general formula (2d). One ring structure represented by the general formula (2c) may be combined with one ring structure represented by the general formula (2d).

  By simultaneously holding the partial structures of the general formula (200) and the general formula (2Y) in one molecule, ΔST can be designed to be effectively small.

  The second compound according to this embodiment preferably has a structure represented by the following general formula (2e) in the molecule.

In the general formula (2e), R _{1 to} R ₉ are each independently a hydrogen atom, a substituent, or a single bond that binds to another atom in the molecule of the second compound;
The substituent in R _{1 to} R ₉ is a halogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 30 ring atoms, substituted Or an unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, a substituted or unsubstituted arylsilyl group having 6 to 60 ring carbon atoms, a substituted or unsubstituted group. An alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms, a substituted or unsubstituted alkylamino group having 2 to 30 carbon atoms, a substituted or unsubstituted ring carbon number A 6 to 60 arylamino group, a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, and a substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms. It is a substituent selected from the group. However, at least one of R _{1 to} R ₉ is a single bond that binds to another atom in the molecule of the second compound.
In the general formula (2e), at least one of the combinations of substituents selected from R _{1 to} R ₉ may be bonded to each other to form a ring structure. In the case of forming this ring structure, that is, in the general formula (2e), among the 6-membered ring carbon atoms or 5-membered ring nitrogen atoms to which R _{1 to} R ₉ are respectively bonded, Substituents selected from R _{1 to} R ₈ bonded to each other and R ₉ bonded to a nitrogen atom of a 5-membered ring can form a ring structure. Specifically, in the general formula (2e), R ₁ and R ₂ , R ₂ and R ₃ , R ₃ and R ₄ , R ₄ and R ₅ , R ₅ and R ₆ , R ₆ and R ₇ , R Among the combinations of substituents consisting of ₇ and R ₈ , R ₈ and R ₉ , R ₁ and R ₉ , at least one set may be bonded to each other to form a ring structure.
In the present embodiment, the ring structure formed by combining substituents with each other is preferably a condensed ring. For example, as a case where the ring structure is formed in the general formula (2e), a case where a condensed 6-membered ring structure is formed can be considered.

  Moreover, it is preferable that the 2nd compound which concerns on this embodiment has the structure represented by the following general formula (2y) in the molecule | numerator.

R _{11 to} R ₁₉ in the general formula (2y) are independently the same as R _{1 to} R ₉ in the general formula (2e). However, at least one of R _{11 to} R ₁₉ is a single bond that binds to another atom in the molecule of the second compound. In the general formula (2y), at least one of the combinations of substituents selected from R _{11 to} R ₁₉ may be bonded to each other to form a ring structure. In the general formula (2y), A and B each independently represent a ring structure represented by the following general formula (2g) or a ring structure represented by the following general formula (2h), The ring structure B is condensed with an adjacent ring structure at an arbitrary position. px is the number of the ring structure A, and is an integer of 0 or more and 4 or less. When px is an integer of 2 or more and 4 or less, the plurality of ring structures A may be the same as or different from each other. When py is an integer of 2 or more and 4 or less, the plurality of ring structures B may be the same or different from each other. py is the number of ring structures B and is an integer of 0 or more and 4 or less. Therefore, for example, when px is 2, the two ring structures A may have two ring structures represented by the following general formula (2g), or two ring structures represented by the following general formula (2h). Or a combination of one ring structure represented by the following general formula (2g) and one ring structure represented by the following general formula (2h).

In the general formula (2g), R ₂₀₁ and R ₂₀₂ are each independently synonymous with R _{1 to} R ₉ , and R ₂₀₁ and R ₂₀₂ may be bonded to each other to form a ring structure. . R ₂₀₁ and R ₂₀₂ are each bonded to a carbon atom forming the 6-membered ring of the general formula (2g).
In the general formula (2h), Z ₈ represents CR ₂₀₃ R ₂₀₄ , NR ₂₀₅ , a sulfur atom, or an oxygen atom, and R _{202 to} R ₂₀₅ are each independently a substituent in R _{1 to} R ₉ . It is synonymous.
In the general formula (2y), at least one of the combinations of substituents selected from R _{11 to} R ₁₉ and R _{201 to} R ₂₀₅ may be bonded to each other to form a ring structure.

  In the general formula (2y), when px is 0 and py is c, it is represented by the following general formula (2f).

R _{11 to} R ₁₉ in the general formula (2f) are independently the same as R _{1 to} R ₉ in the general formula (2e). However, at least one of R _{11 to} R ₁₉ is a single bond that binds to another atom in the molecule of the second compound. In the general formula (2f), at least one of the combinations of substituents selected from R _{11 to} R ₁₉ may be bonded to each other to form a ring structure. In the general formula (2f), E represents a ring structure represented by the general formula (2g) or a ring structure represented by the general formula (2h), and the ring structure E represents an adjacent ring structure. And condensed at any position. c is the number of the ring structure E, and is an integer of 1 or more and 4 or less. When c is an integer of 2 or more and 4 or less, the plurality of ring structures E may be the same as or different from each other. Therefore, for example, when c is 2, the two ring structures E may have two ring structures represented by the general formula (2g) or two ring structures represented by the general formula (2h). Or a combination of one ring structure represented by the following general formula (2g) and one ring structure represented by the general formula (2h).

  The second compound according to this embodiment is preferably represented by the following general formula (2A).

In the general formula (2A), n is an integer of 1 or more, t is an integer of 1 or more, and u is an integer of 0 or more. L _A is a substituted or unsubstituted ring formed C6-30 aromatic hydrocarbon ring or aromatic heterocyclic ring atoms 6 to 30. CN is a cyano group. D ₁ and D ₂ are each independently represented by the general formula (2Y), provided that the ring structure F and the ring structure G in the general formula (2Y) may be unsubstituted or have a substituent. Well, m is 0 or 1, and when m is 1, Y ₂₀ is a single bond, oxygen atom, sulfur atom, selenium atom, carbonyl group, CR ₂₁ R ₂₂ , SiR ₂₃ R ₂₄ or GeR _25. R ₂₆ represents R ₂₆ , and R _{21 to} R ₂₆ have the same meaning as R. When m is 1, the general formula (2Y) is represented by any one of the general formulas (22) to (25) and the general formulas (21Y) to (24Y). D ₁ and D ₂ may be the same or different. When t is 2 or more, the plurality of D ₁ may be the same as or different from each other. When u is 2 or more, the plurality of D ₂ may be the same as or different from each other.

In this embodiment, L _A is preferably a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 14 ring carbon atoms. Examples of the aromatic hydrocarbon ring having 6 to 14 ring carbon atoms include benzene, naphthalene, fluorene, and phenanthrene. Wherein L _A is more preferably an aromatic hydrocarbon ring ring carbon atoms 6-10.
The aromatic heterocyclic ring atoms 6 to 30 in the L _A, for example, pyridine, pyrimidine, pyrazine, quinoline, quinazoline, phenanthroline, benzofuran, and dibenzofuran, and the like.

In the present embodiment, in the general formula (2A), the first of the D ₁ or the D ₂ is bonded to the carbon atoms forming the aromatic hydrocarbon ring represented by L _A, the first The CN may be bonded to the second carbon atom adjacent to the carbon atom. For example, in the second compound according to the present embodiment, as the partial structure represented by the following general formula (2B), wherein D is attached to the first carbon atom C _1, the first carbon atom C _A cyano group may be bonded to the second carbon atom C ₂ adjacent to ₁ . D in the following general formula (2B) has the same meaning as D ₁ or D ₂ . In the following general formula (2B), a wavy line portion represents a bonding position with another structure or atom.

And D ₁ or D ₂ having the structure as shown in formula (2a) or Formula (2b), bonded to the aromatic hydrocarbon ring is a cyano group represented by adjacent said L _A As a result, the value of ΔST of the compound can be reduced.

In the present embodiment, the t is preferably an integer of 2 or more. If the said D ₁ of the 2 or more aromatic hydrocarbon ring represented by L _A is attached, a plurality of D ₁ may be a different structure may be the same structure.

  The second compound according to this embodiment is preferably represented by the following general formula (21).

In the general formula (21), A ₂₁ and B ₂₁ are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring forming atom number of 5 to 5. 30 aromatic heterocyclic groups are represented.
X _{21 to} X ₂₈ and Y _{21 to} Y ₂₈ each independently represent a nitrogen atom, a carbon atom bonded to ^RD , or a carbon atom bonded to L ₂₃ . However, at least one of X _{25 to} X ₂₈ is a carbon atom bonded to L _23, and at least one of Y _{21 to} Y ₂₄ is a carbon atom bonded to L ₂₃ .
^RD each independently represents a hydrogen atom or a substituent, and the substituent in ^RD is a halogen atom, a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted or unsubstituted group. It is a substituent selected from the group consisting of a substituted aromatic heterocyclic group having 5 to 30 atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted silyl group.
L ₂₁ and L ₂₂ are each independently a single bond or a linking group. Examples of the linking group in L ₂₁ and L ₂₂ include a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, a substituted group Or an unsubstituted heterocyclic group having 5 to 30 ring atoms, a multiple linking group formed by bonding 2 to 4 groups selected from the aromatic hydrocarbon groups, and two selected from the heterocyclic groups Or a multi-linking group formed by bonding two to four groups selected from the aromatic hydrocarbon group and the heterocyclic group.
L ₂₃ represents a substituted or unsubstituted monocyclic hydrocarbon group having 6 or less ring-forming carbon atoms, or a substituted or unsubstituted monocyclic heterocyclic group having 6 or less ring-forming atoms.
w represents an integer of 0 to 3. When w is 0, at least one of X _{25 to} X ₂₈ and at least one of Y _{21 to} Y ₂₄ are directly bonded.
A monocyclic hydrocarbon group is not a condensed ring but a group derived from a single hydrocarbon ring (aliphatic cyclic hydrocarbon or aromatic hydrocarbon), and a monocyclic heterocyclic group is a single ring A group derived from a heterocyclic ring.

Further, in the general formula (21), at least one of the following conditions (i) and (ii) is satisfied.
(I) At least one of A ₂₁ and B ₂₁ is an aromatic hydrocarbon group having 6 to 30 ring carbon atoms substituted with a cyano group, or an aromatic having 6 to 30 ring atoms substituted with a cyano group Group heterocyclic group.
_(Ii) at least one of X 21 _{to X 24} and _Y 25 _{to Y 28} is a carbon atom bonded with ^{R D,} the ^R at least one of ^D is, ring carbon 6 is substituted with a cyano group Or an aromatic heterocyclic group having 6 to 30 ring atoms substituted with an aromatic hydrocarbon group having ˜30 or a cyano group.
However, if R ^D there are a plurality, or different in each of the plurality of R ^D identical.

In the general formula (21), the aromatic hydrocarbon group having 6 to 30 ring carbon atoms or the aromatic heterocyclic group having 6 to 30 ring atoms represented by A ₂₁ and B ₂₁ has a substituent. In the case, the substituent is a cyano group, a halogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, a haloalkyl group having 1 to 20 carbon atoms, Haloalkoxy group having 1 to 20 carbon atoms, alkylsilyl group having 1 to 10 carbon atoms, aryl group having 6 to 30 ring carbon atoms, aryloxy group having 6 to 30 ring carbon atoms, and aralkyl having 6 to 30 carbon atoms It is preferably one or more groups selected from the group consisting of a group and a heterocyclic group having 5 to 30 ring atoms. When A ₂₁ and B ₂₁ have a plurality of substituents, the substituents may be the same or different.

In the general formula (21), it is preferable that the condition (i) is satisfied and the condition (ii) is not satisfied.
Alternatively, in the general formula (21), it is preferable that the condition (ii) is satisfied and the condition (i) is not satisfied.
Alternatively, it is also preferable to satisfy the condition (i) and the condition (ii).

In the general formula (21), at least one of A ₂₁ and B ₂₁ is
A phenyl group substituted with a cyano group,
A naphthyl group substituted with a cyano group,
A phenanthryl group substituted with a cyano group,
A dibenzofuranyl group substituted with a cyano group,
A dibenzothiophenyl group substituted with a cyano group,
A biphenyl group substituted with a cyano group,
A terphenyl group substituted with a cyano group,
A 9,9-diphenylfluorenyl group substituted with a cyano group,
A 9,9′-spirobi [9H-fluoren] -2-yl group substituted with a cyano group,
A 9,9-dimethylfluorenyl group substituted with a cyano group or a triphenylenyl group substituted with a cyano group is preferred.

In the general formula _(21), at least one of X 21 _{to X 24} and _Y 25 _{to Y 28} are CR _^D, at least one of ^{R D} in X 21 _{to X 24} and _Y 25 _{to Y 28} are,
A phenyl group substituted with a cyano group,
A naphthyl group substituted with a cyano group,
A phenanthryl group substituted with a cyano group,
A dibenzofuranyl group substituted with a cyano group,
A dibenzothiophenyl group substituted with a cyano group,
A biphenyl group substituted with a cyano group,
A terphenyl group substituted with a cyano group,
A 9,9-diphenylfluorenyl group substituted with a cyano group,
A 9,9′-spirobi [9H-fluoren] -2-yl group substituted with a cyano group,
A 9,9-dimethylfluorenyl group substituted with a cyano group or a triphenylenyl group substituted with a cyano group is preferred.

In the general formula (21), X ₂₆ and Y ₂₃ are preferably bonded via L ₂₃ or directly bonded.
Further, in the general formula _(21), and _{X 26} and _{Y 22} is _either attached via a _{L 23,} or is preferably bonded directly.
Further, in the general formula _(21), and _{X 27} and _{Y 23} is _either attached via a _{L 23,} or is preferably bonded directly.

In the general formula (21), w is preferably 0.
Alternatively, in the general formula (21), w is preferably 1.

In the general formula (21), L ₂₁ and L ₂₂ are preferably a single bond or a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.

  Specific examples of the second compound are shown below. In addition, the 2nd compound in this invention is not limited to these examples.

-Manufacturing method of 2nd compound A 2nd compound is manufactured according to the method described in international publication 2013/180241, international publication 2014/092083, international publication 2014/104346, etc., for example. be able to.

Delayed fluorescence Delayed fluorescence (thermally activated delayed fluorescence) is described on pages 261 to 268 of “Device properties of organic semiconductors” (edited by Chiba Adachi, published by Kodansha). In that document, if the energy difference ΔE ₁₃ between the excited singlet state and the excited triplet state of the fluorescent material can be reduced, the reverse energy from the excited triplet state to the excited singlet state, which usually has a low transition probability. It is described that migration occurs with high efficiency, and thermally activated delayed fluorescence (TADF) is expressed. In addition, FIG. 10.38 in this document explains the mechanism of delayed fluorescence generation. The second compound in the present embodiment is a compound that exhibits thermally activated delayed fluorescence generated by such a mechanism.

  The delayed fluorescence emission can be confirmed by transient PL (Photo Luminescence) measurement.

The behavior of delayed fluorescence can also be analyzed based on the decay curve obtained from the transient PL measurement. Transient PL measurement is a method of measuring the decay behavior (transient characteristics) of PL emission after irradiating a sample with a pulse laser and exciting it and stopping the irradiation. PL emission in the TADF material is classified into a light emission component from a singlet exciton generated by the first PL excitation and a light emission component from a singlet exciton generated via a triplet exciton. The lifetime of singlet excitons generated by the first PL excitation is on the order of nanoseconds and is very short. Therefore, light emitted from the singlet excitons is rapidly attenuated after irradiation with the pulse laser.
On the other hand, delayed fluorescence is gradually attenuated due to light emission from singlet excitons generated via a long-lived triplet exciton. Thus, there is a large time difference between the light emission from the singlet exciton generated by the first PL excitation and the light emission from the singlet exciton generated via the triplet exciton. Therefore, the emission intensity derived from delayed fluorescence can be obtained.

FIG. 2 shows a schematic diagram of an exemplary apparatus for measuring transient PL.
The transient PL measurement apparatus 100 of the present embodiment includes a pulse laser unit 101 that can irradiate light of a predetermined wavelength, a sample chamber 102 that houses a measurement sample, a spectrometer 103 that separates light emitted from the measurement sample, A streak camera 104 for forming a two-dimensional image and a personal computer 105 for capturing and analyzing the two-dimensional image are provided. Note that the measurement of the transient PL is not limited to the apparatus described in this embodiment.
The sample accommodated in the sample chamber 102 is obtained by forming a thin film in which a doping material is doped at a concentration of 12 mass% with respect to a matrix material on a quartz substrate.
The thin film sample accommodated in the sample chamber 102 is irradiated with a pulse laser from the pulse laser unit 101 to excite the doping material. The emitted light is extracted in a direction of 90 degrees with respect to the irradiation direction of the excitation light, the extracted light is dispersed by the spectroscope 103, and a two-dimensional image is formed in the streak camera 104. As a result, a two-dimensional image can be obtained in which the vertical axis corresponds to time, the horizontal axis corresponds to wavelength, and the bright spot corresponds to emission intensity. When this two-dimensional image is cut out along a predetermined time axis, an emission spectrum in which the vertical axis represents the emission intensity and the horizontal axis represents the wavelength can be obtained. Further, when the two-dimensional image is cut out along the wavelength axis, an attenuation curve (transient PL) in which the vertical axis represents the logarithm of the emission intensity and the horizontal axis represents time can be obtained.

  For example, the thin film sample A was prepared as described above using the following reference compound H1 as a matrix material and the following reference compound D1 as a doping material, and transient PL measurement was performed.

Here, the attenuation curve was analyzed using the thin film sample A and the thin film sample B described above. Thin film sample B was prepared as described above using reference compound H2 as a matrix material and reference compound D1 as a doping material.
FIG. 3 shows attenuation curves obtained from the transient PL measured for the thin film sample A and the thin film sample B.

As described above, by the transient PL measurement, it is possible to obtain a light emission decay curve with the vertical axis representing the emission intensity and the horizontal axis representing the time. Based on this emission decay curve, the fluorescence intensity of fluorescence emitted from the singlet excited state generated by photoexcitation and delayed fluorescence emitted from the singlet excited state generated by reverse energy transfer via the triplet excited state The ratio can be estimated. In the delayed fluorescent material, the ratio of the delayed fluorescence intensity that gradually attenuates to the fluorescence intensity that decays quickly is somewhat large.
The amount of delayed fluorescence emitted in this embodiment can be determined using the apparatus shown in FIG. The first compound is excited with pulsed light having a wavelength that is absorbed by the second compound (light emitted from a pulsed laser) and then promptly observed from the excited state (prompt light emission). After the excitation, there is delay light emission (delayed light emission) that is not observed immediately but is observed thereafter. In the present embodiment, the amount of delay light emission (delayed light emission) is preferably 5% or more with respect to the amount of Promp light emission (immediate light emission).
The amounts of Prompt light emission and Delay light emission can be obtained by the same method as described in “Nature 492, 234-238, 2012”. In addition, the apparatus used for calculation of the amount of Promp light emission and Delay light emission is not limited to the apparatus described in the said literature.
In addition, the sample used for the measurement of delayed fluorescence is, for example, co-evaporated the second compound and the following compound TH-2 on a quartz substrate so that the ratio of the second compound is 12% by mass, A sample in which a thin film having a thickness of 100 nm is formed can be used.

-TADF mechanism In the organic EL device of the present embodiment, it is preferable to use a compound having a small ΔST (Mat1) as the second compound, and the second compound from the triplet level of the second compound by the externally applied thermal energy. The reverse intersystem crossing to the singlet level easily occurs. An energy state conversion mechanism in which the excited triplet state of the electrically excited exciton inside the organic EL element is spin-exchanged to the excited singlet state by crossing between inverse terms is called a TADF mechanism.
FIG. 4 is a diagram illustrating an example of the relationship between the energy levels of the first compound and the second compound in the light emitting layer. In FIG. 4, S0 represents the ground state, S1 (Mat1) represents the lowest excited singlet state of the first compound, T1 (Mat1) represents the lowest excited triplet state of the first compound, S1 (Mat2) represents the lowest excited singlet state of the second compound, and T1 (Mat2) represents the lowest excited triplet state of the second compound. The dashed arrow from S1 (Mat2) to S1 (Mat1) in FIG. 4 represents the Forster energy transfer from the lowest excited singlet state of the second compound to the lowest excited singlet state of the first compound. . In the present embodiment, the difference between the lowest excited singlet state S1 and the lowest excited triplet state T1 is defined as ΔST.
As shown in FIG. 4, when a compound having a small ΔST (Mat2) is used as the second compound, the lowest excited triplet state T1 (Mat2) is reversed to the lowest excited singlet state S1 (Mat2) by thermal energy. Intersection is possible. Then, a Forster energy transfer occurs from the lowest excited singlet state S1 (Mat2) of the second compound to the lowest excited singlet state S1 (Mat1) of the first compound. As a result, fluorescence emission from the lowest excited singlet state S1 (Mat1) of the first compound can be observed. It is believed that the internal efficiency can theoretically be increased to 100% also by utilizing delayed fluorescence due to this TADF mechanism.

<Relationship between first compound and second compound in light emitting layer>
In the organic EL device of the present embodiment, the singlet energy S _{1 (Mat1)} of the first compound, singlet energy S _{1 (Mat2)} The second compound, satisfies the following equation (Equation 1) It is preferable.
S ₁ (Mat 2)> S ₁ (Mat 1) (Equation 1)

The energy gap T _77K (Mat2) at 77 [K] of the second compound is preferably larger than the energy gap T _77K (Mat1) at 77 [K] of the first compound.

-Relationship between triplet energy and energy gap at 77 [K] Here, the relationship between triplet energy and energy gap at 77 [K] will be described. In the present embodiment, the energy gap at 77 [K] is different from the normally defined triplet energy.
The triplet energy is measured as follows. First, a sample in which a solution in which a compound to be measured is dissolved in an appropriate solvent is enclosed in a quartz glass tube is prepared. With respect to this sample, a phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) is measured at a low temperature (77 [K]), and a tangent line is drawn with respect to the rising edge on the short wavelength side of the phosphorescence spectrum, Based on the wavelength value at the intersection of the tangent and the horizontal axis, triplet energy is calculated from a predetermined conversion formula.
Here, among the compounds according to the present embodiment, the thermally activated delayed fluorescent compound is preferably a compound having a small ΔST. When ΔST is small, intersystem crossing and reverse intersystem crossing easily occur even in a low temperature (77 [K]) state, and an excited singlet state and an excited triplet state are mixed. As a result, the spectrum measured in the same manner as described above includes emission from both the excited singlet state and the excited triplet state, and it is difficult to distinguish from which state the light is emitted. Basically, the triplet energy value is considered dominant.
Therefore, in the present embodiment, the normal triplet energy T and the measurement method are the same, but in order to distinguish the difference in the strict meaning, the value measured as follows is referred to as an energy gap T _77K. . A compound to be measured is dissolved in EPA (diethyl ether: isopentane: ethanol = 5: 5: 2 (volume ratio)) so as to have a concentration of 10 μmol / L, and this solution is placed in a quartz cell and measured. A sample is used. With respect to this measurement sample, a phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) is measured at a low temperature (77 [K]), and a tangent line is drawn with respect to the rising edge of the phosphorescence spectrum on the short wavelength side. Based on the wavelength value λ _edge [nm] at the intersection of the tangent and the horizontal axis, the energy amount calculated from the following conversion formula (F1) is defined as an energy gap T _77K at 77 [K].
Conversion formula (F1): T _77K [eV] = 1239.85 / λ _edge

The tangent to the rising edge on 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, tangents at each point on the curve are considered toward the long wavelength side. The slope of this tangent line increases as the curve rises (that is, as the vertical axis increases). A tangent drawn at a point where the value of the slope takes a maximum value (that is, a tangent at the inflection point) is a tangent to the rising edge of the phosphorescence spectrum on the short wavelength side.
Note that the maximum point having a peak intensity of 15% or less of the maximum peak intensity of the spectrum is not included in the above-mentioned maximum value on the shortest wavelength side, and has the maximum slope value closest to the maximum value on the shortest wavelength side. The tangent drawn at the point where the value is taken is taken as the tangent to the rising edge of the phosphorescence spectrum on the short wavelength side.
For measurement of phosphorescence, an F-4500 spectrofluorometer main body manufactured by Hitachi High-Technology Co., Ltd. can be used. Note that the measurement device is not limited to this, and the measurement may be performed by combining a cooling device, a low-temperature container, an excitation light source, and a light receiving device.

・ Singlet energy S ₁
Examples of a method for measuring singlet energy S ₁ using a solution (sometimes referred to as a solution method) include the following methods.
A 10 μmol / L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the absorption spectrum (vertical axis: absorption intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300 K). A tangent line is drawn with respect to the fall of the absorption spectrum on the long wavelength side, and the singlet energy is calculated by substituting the wavelength value λedge [nm] at the intersection of the tangent line and the horizontal axis into the following conversion formula (F2). To do.
Conversion formula (F2): S ₁ [eV] = 1239.85 / λedge
Examples of the absorption spectrum measuring device include a spectrophotometer (device name: U3310) manufactured by Hitachi, but are not limited thereto.

The tangent to the falling edge on the long wavelength side of the absorption spectrum is drawn as follows. When moving on the spectrum curve in the long wavelength direction from the maximum value on the longest wavelength side among the maximum values of the absorption spectrum, the tangent at each point on the curve is considered. This tangent repeats as the curve falls (ie, as the value on the vertical axis decreases), the slope decreases and then increases. The tangent drawn at the point where the slope value takes the minimum value on the long wavelength side (except when the absorbance is 0.1 or less) is taken as the tangent to the fall on the long wavelength side of the absorption spectrum.
In addition, the maximum point whose absorbance value is 0.2 or less is not included in the maximum value on the longest wavelength side.

In the present embodiment, the difference (S ₁ −T _77K ) between the singlet energy S ₁ and the energy gap T _{77K at} 77 [K] is defined as ΔST.

In this embodiment, the difference ΔST (Mat2) between the singlet energy S ₁ (Mat2) of the second compound and the energy gap T _77K (Mat2) at 77 [K] of the second compound is preferably Less than 0.3 eV, more preferably less than 0.2 eV, still more preferably less than 0.1 eV. That is, ΔST (Mat2) preferably satisfies any one of the following mathematical formulas (Equation 10) to (Equation 12).
ΔST (Mat2) = S ₁ (Mat2) −T _77K (Mat2) <0.3 eV (Equation 10)
ΔST (Mat2) = S ₁ (Mat2) −T _77K (Mat2) <0.2 eV (Equation 11)
ΔST (Mat2) = S ₁ (Mat2) −T _77K (Mat2) <0.1 eV (Equation 12)

-Film thickness of light emitting layer The film thickness of the light emitting layer in the organic EL device of the present embodiment is preferably 5 nm to 50 nm, more preferably 7 nm to 50 nm, and most preferably 10 nm to 50 nm. When the thickness is 5 nm or more, formation of the light emitting layer and adjustment of chromaticity are easy to be performed, and when the thickness is 50 nm or less, an increase in driving voltage is easily suppressed.

-Content rate of the compound in a light emitting layer In the organic EL element of this embodiment, it is preferable that the content rate of a 1st compound is 0.01 mass% or more and 10 mass% or less in a light emitting layer, and it is a 2nd compound. The content of is preferably 80% by mass or more and 99.99% by mass or less. The upper limit of the total content of the first compound and the second compound in the light emitting layer is 100% by mass. Note that this embodiment does not exclude that the light emitting layer contains a material other than the first compound and the second compound. The light emitting layer may contain only one kind of the first compound. Two or more kinds may be included. The light emitting layer may contain only 1 type of 2nd compounds, and may contain 2 or more types.

<Second organic layer>
The second organic layer (in this embodiment, the electron barrier layer) contains a third compound.

(Third compound)
The third compound is a compound represented by the following general formula (3).

In the general formula (3),
n is 1, 2, 3, or 4;
when n is 2, 3, or 4, the plurality of Cz are the same or different from each other;
X _B is a group represented by the following general formula (3A),
Cz is a group represented by the following general formula (3B-1) or (3B-2).

In the general formula (3A),
Ar ₁ is
Monovalent or polyvalent residues derived from substituted or unsubstituted dibenzofurans,
Monovalent or polyvalent residues derived from substituted or unsubstituted azadibenzofuran,
A monovalent or polyvalent residue derived from substituted or unsubstituted dibenzothiophene, or a monovalent or polyvalent residue derived from substituted or unsubstituted azadibenzothiophene,
Ar ₂ is independently
A monovalent or polyvalent residue derived from a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms,
Monovalent or polyvalent residues derived from substituted or unsubstituted dibenzofurans,
Monovalent or polyvalent residues derived from substituted or unsubstituted azadibenzofuran,
A monovalent or polyvalent residue derived from substituted or unsubstituted dibenzothiophene, or a monovalent or polyvalent residue derived from substituted or unsubstituted azadibenzothiophene,
k is 0, 1, 2, 3, or 4;
when k is 2, 3, or 4, the plurality of Ar ₂ are the same or different from each other;
In the case where Ar ₁ has a substituent, the substituent D 1 is independently
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,
A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted C1-C30 halogenated alkoxy group,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted silyl group,
Halogen atoms,
Selected from the group consisting of a cyano group and a nitro group,
The substituent D2 in the case where Ar ₂ has a substituent has the same meaning as the substituent D1,
When n is 1, Cz binds to Ar ₁
When n is 2, 3, or 4, a plurality of Cz are each independently bonded to Ar ₁ or bonded to Ar ₂ . However, at least one Cz is bonded to Ar ₁ .

In the general formula (3B-1),
X _{1 to} X ₈ are each independently a nitrogen atom or CR _A ,
R _A is a hydrogen atom or a substituent, or any one or more of the groups of adjacent R _A are bonded to each other to form a ring,
R _A as a substituent is each independently
A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted silyl group,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted C1-C30 halogenated alkoxy group,
A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,
Halogen atoms,
A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,
A cyano group,
A hydroxy group,
Selected from the group consisting of a nitro group and a carboxy group;
The plurality of R _A are the same or different from each other,
However, the nitrogen atom in the general formula (3B-1) is bonded to either Ar ₁ or Ar _{2 in} the general formula (3A).

In the general formula (3B-2),
Or X ₁ to X ₄ are the general formula (3A) in the carbon atom bonded to the one of Ar ₁ and Ar _2, a nitrogen atom or a CR _{C, R C} is a hydrogen atom or a substituent, or bonded to any one or more sets of pairs of _{R C} adjacent to each other to form a ring, provided _that one of X 1 to X ₄ are in the general formula (3A), Ar ₁ and Ar ₂ is a carbon atom bonded to any one of
X ₅ to X ₈ is a nitrogen atom or a CR _D, R _D is a hydrogen atom or a substituent, or adjacent R _D any one or more sets of pairs of mutually bonded each other to form a ring Form the
R _B , R _C and R _D are each independently synonymous with R _A in the general formula (3B-1), and the plurality of R _C are the same as or different from each other, and the plurality of R _D are The same or different,
In the third compound, the substituent E in the case of “substituted or unsubstituted” is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted C1-C30 halogenated alkoxy group,
A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,
A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,
Halogen atoms,
A carboxy group,
A substituted or unsubstituted amino group,
Nitro group,
A cyano group,
A substituted or unsubstituted silyl group,
It is a substituent selected from the group consisting of a substituted phosphoryl group and a hydroxy group.
When the substituent E further has a substituent F, the substituent F is
An unsubstituted aryl group having 6 to 30 ring carbon atoms,
An unsubstituted heteroaryl group having 5 to 30 ring atoms;
An unsubstituted alkyl group having 1 to 30 carbon atoms,
An unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
An unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
Unsubstituted silyl group,
An unsubstituted alkoxy group having 1 to 30 carbon atoms,
An unsubstituted halogenated alkoxy group having 1 to 30 carbon atoms,
An unsubstituted aryloxy group having 6 to 30 carbon atoms,
An unsubstituted alkylthio group having 1 to 30 carbon atoms,
An unsubstituted arylthio group having 6 to 30 ring carbon atoms,
An unsubstituted aralkyl group having 7 to 30 carbon atoms,
An unsubstituted alkenyl group having 2 to 30 carbon atoms,
Halogen atoms,
An unsubstituted alkynyl group having 2 to 30 carbon atoms,
A cyano group,
A hydroxy group,
Selected from the group consisting of a nitro group and a carboxy group, provided that substituent F has no further substituents.
The substituent E is preferably not a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms and a substituted or unsubstituted amino group.
The substituent F is preferably not an unsubstituted heteroaryl group having 5 to 30 ring atoms.

At least one Cz in the general formula (3) is bonded to Ar ₁ in the general formula (3A). When there are a plurality of Cz, at least one Cz in the general formula (3) is bonded to Ar ₁ in the general formula (3A), and the other Cz is independently Ar ₁ in the general formula (3A). Or it binds to Ar ₂ .

The binding mode of the compounds represented by the general formulas (3) and (3A) is determined according to the values of n and k. For example, when n is 1, 2, 3, or 4 each independently, and k is each independently 0, 1, or 2, examples of the binding modes include the following.
For the binding mode when n is independently 1, 2, 3, or 4 and k is independently 3 or 4, when n is 1 and k is 3, Only the binding mode is illustrated, and description of other binding modes is omitted. However, the bonding mode of the compounds represented by the general formulas (3) and (3A) is not limited to the following.

-Bonding mode when n is 1 in general formula (3) and k is 0 in general formula (3A)

-Bonding mode when n is 1 in general formula (3) and k is 1 in general formula (3A)

-Bonding mode when n is 1 in general formula (3) and k is 2 in general formula (3A)

-Bonding mode when n is 2 in general formula (3) and k is 0 in general formula (3A)

-Bonding mode when n is 2 in general formula (3) and k is 1 in general formula (3A)

-Bonding mode when n is 2 in general formula (3) and k is 2 in general formula (3A)

-Bonding mode when n is 3 in general formula (3) and k is 0 in general formula (3A)

-Bonding mode when n is 3 in general formula (3) and k is 1 in general formula (3A)

-Bonding mode when n is 3 in general formula (3) and k is 2 in general formula (3A)

-Bonding mode when n is 4 in general formula (3) and k is 0 in general formula (3A)

-Bonding mode when n is 4 in general formula (3) and k is 1 in general formula (3A)

-Bonding mode when n is 4 in general formula (3) and k is 2 in general formula (3A)

-Bonding mode when n is 1 in general formula (3) and k is 3 in general formula (3A)

Bonding pattern, if the in formula (3-1) to (3-45), a plurality of Cz are the same or different from each other, if Ar ₂ there are a plurality, a plurality of Ar ₂ may be the same or different from each other.

When the bonding mode is the general formulas (3-1) to (3-45), examples of Cz in the general formulas (3-1) to (3-44) include the following Tables 6 to 13: The group shown in these is mentioned. * Represents a bonding point.
The groups shown in Tables 2 to 9 below are examples of groups corresponding to _RA in the general formula (3B-1). The group corresponding to R _A shown below may have the substituents listed for the substituent of R _A. Each of the substituents of _RA may be independently further substituted with the substituent E, and the substituent E may be further substituted with the substituent F.

In the general formula (3B-1), X _{1 to} X ₈ are preferably each independently CR _A.

One of the _X 1 to X ₄ in the general formula (3B-2), each independently, a carbon atom bonded with any of Ar ₁ and Ar _2, or a CR _{C, however,} X 1 to X ₄ is in the general formula (3A), a carbon atom bonded with any of Ar ₁ and Ar _2, X 5 ~X ₈ each independently is preferably a CR _D.

In the general formula (3B-1), it is preferable that the groups of adjacent R _A are not bonded to each other.

In the general formula (3B-2), a set of R _C between adjacent are both not bind to each other, a set of R _D between adjacent are both preferably do not bind to each other.

R _A in the general formula (3B-1) and R _B , R _C and R _D in the general formula (3B-2) are each independently a hydrogen atom, a substituted or unsubstituted ring-forming carbon number of 6 to 30 An aryl group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a carbazolyl group, a substituted carbazolyl group, a halogen atom, or a cyano group. Is preferred.

R _A in the general formula (3B-1) and R _B , R _C, and R _D in the general formula (3B-2) are each independently a hydrogen atom, a substituted or unsubstituted ring-forming carbon number of 6 to 6 It is more preferably a 30 aryl group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms.

R _A in the general formula (3B-1) and R _C and R _D in the general formula (3B-2) are more preferably a hydrogen atom.

Cz in the general formula (3) is preferably a group represented by the general formula (3B-1).
In the general formulas (3-1) to (3-37), it is preferable that at least one Cz is a group represented by the general formula (3B-1), and all Cz are the general formula ( The group represented by 3B-1) is more preferable.

  N in the general formula (3) is preferably 2.

  In general formula (3A), k is preferably 1.

  In the general formula (3), n is 2, and k is preferably 1. That is, the third compound is preferably a compound represented by the general formula (3-6) or (3-7), and is a compound represented by the general formula (3-6). preferable.

Ar ₁ in the general formula (3A) is a monovalent or polyvalent residue derived from a substituted or unsubstituted dibenzofuran, or a monovalent or polyvalent residue derived from a substituted or unsubstituted dibenzothiophene. It is preferable that
Ar ₁ in the general formula (3A) is more preferably a monovalent or polyvalent residue derived from substituted or unsubstituted dibenzofuran.

Ar ₂ in the general formula (3A) is independently a substituted or unsubstituted monovalent or polyvalent residue derived from a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms, substituted or unsubstituted. A monovalent or polyvalent residue derived from a dibenzofuran having 6 to 18 ring carbon atoms, or a monovalent or polyvalent residue derived from a substituted or unsubstituted dibenzothiophene having 6 to 18 ring carbon atoms. It is preferably a group.
Ar ₂ in the general formula (3A) is independently a monovalent or polyvalent residue derived from a substituted or unsubstituted aromatic hydrocarbon group having 6 to 12 ring carbon atoms. preferable.

N in the general formula (3) is 2, k in the general formula (3A) is 1, and Ar ₁ is a monovalent or polyvalent residue derived from a substituted or unsubstituted dibenzofuran. Ar ₂ is preferably a monovalent or polyvalent residue derived from a substituted or unsubstituted aromatic hydrocarbon group having 6 to 12 ring carbon atoms.

It is preferable that at least one of the plurality of Cz in the general formula (3) is bonded to Ar ₂ . That is, the third compound preferably has a skeleton in which at least one of the plurality of Cz is bonded to Ar ₁ and at least one is bonded to Ar ₂ .

Among the plurality of Cz in the general formula (3), at least one Cz is a carbon atom at the 2-position or 8-position of the dibenzofuran skeleton in Ar ₁ as a monovalent or polyvalent residue, or 2 of the azadibenzofuran skeleton. It is preferably bonded to the carbon atom at the 8th or 8th position, the carbon atom at the 2nd or 8th position of the dibenzothiophene skeleton, or the carbon atom at the 2nd or 8th position of the azadibenzothiophene skeleton.

Of the plurality of Cz in the general formula (3), at least one Cz is a group represented by the general formula (3B-1), and a bond of the group represented by the general formula (3B-1) Position * is the 2- or 8-position carbon atom of the dibenzofuran skeleton in Ar ₁ as a monovalent or polyvalent residue, the 2- or 8-position carbon atom of the azadibenzofuran skeleton, the 2-position of the dibenzothiophene skeleton, or It is preferably bonded to the carbon atom at the 8-position or the carbon atom at the 2- or 8-position of the azadibenzothiophene skeleton.

Among the plurality of Cz in the general formula (3), at least one Cz is a group represented by the general formula (3B-2), and X of the group represented by the general formula (3B-2) ₃ or X ₆ is preferably bonded to Ar ₁ as a monovalent or polyvalent residue.

Among the plurality of Cz in the general formula (3), at least one Cz is a group represented by the general formula (3B-2), and X of the group represented by the general formula (3B-2) ₃ or X ₆ is a carbon atom at the 2nd or 8th position of the dibenzofuran skeleton in Ar ₁ as a monovalent or polyvalent residue, a carbon atom at the 2nd or 8th position of the azadibenzofuran skeleton, 2 of the dibenzothiophene skeleton It is preferably bonded to the carbon atom at the 8th or 8th position, or the carbon atom at the 2nd or 8th position of the azadibenzothiophene skeleton.

  Cz in the general formula (3) is preferably any group selected from the group consisting of groups represented by the following formulas (3B11) to (3B22).

(In the groups represented by the formulas (3B11) to (3B22), the carbon atom that may have a substituent has the substituent X having the same meaning as R _A as the substituent, or has no substituent. In the case of having a plurality of substituents X, the plurality of substituents X are the same or different from each other, and * in the formulas (3B11) to (3B22) represents a bonding position.

  Cz in the general formula (3) is preferably any group selected from the group consisting of groups represented by the formulas (3B11) to (3B17).

-Manufacturing method of a 3rd compound A 3rd compound can be manufactured by a well-known method.

  Specific examples of the third compound according to this embodiment are shown below. The third compound in the present invention is not limited to these specific examples.

(anode)
For the anode formed on the substrate, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a high work function (specifically, 4.0 eV or more). Specifically, for example, indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, and indium oxide containing zinc oxide. And graphene. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium ( Pd), titanium (Ti), or a metal material nitride (for example, titanium nitride).

  These materials are usually formed by sputtering. For example, indium oxide-zinc oxide can be formed by a sputtering method by using a target in which 1% by mass to 10% by mass of zinc oxide is added to indium oxide. For example, indium oxide containing tungsten oxide and zinc oxide contains 0.5% by mass to 5% by mass of tungsten oxide and 0.1% by mass to 1% by mass of zinc oxide with respect to indium oxide. By using a target, it can be formed by a sputtering method. In addition, you may produce by the vacuum evaporation method, the apply | coating method, the inkjet method, a spin coat method, etc.

  Of the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed using a composite material that facilitates hole injection regardless of the work function of the anode. Any material that can be used as an electrode material (for example, a metal, an alloy, an electrically conductive compound, and a mixture thereof, and other elements belonging to Group 1 or Group 2 of the periodic table) can be used.

  An element belonging to Group 1 or Group 2 of the periodic table, which is a material having a low work function, that is, an alkali metal such as lithium (Li) or cesium (Cs), and magnesium (Mg), calcium (Ca), or strontium Alkaline earth metals such as (Sr), and alloys containing these (eg, MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these can also be used. Note that when an anode is formed using an alkali metal, an alkaline earth metal, and an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Furthermore, when using a silver paste etc., the apply | coating method, the inkjet method, etc. can be used.

(cathode)
It is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a low work function (specifically, 3.8 eV or less) for the cathode. Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg) and calcium (Ca ), Alkaline earth metals such as strontium (Sr), and alloys containing these (for example, rare earth metals such as MgAg, AlLi), europium (Eu), ytterbium (Yb), and alloys containing these.

  Note that in the case where the cathode is formed using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Moreover, when using a silver paste etc., the apply | coating method, the inkjet method, etc. can be used.

  By providing an electron injection layer, a cathode is formed using various conductive materials such as indium oxide-tin oxide containing Al, Ag, ITO, graphene, silicon, or silicon oxide regardless of the work function. can do. These conductive materials can be formed by a sputtering method, an inkjet method, a spin coating method, or the like.

(Hole injection layer)
The hole injection layer is a layer containing a substance having a high hole injection property. Substances with high hole injection properties include 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.

  As a substance having a high hole injection property, 4,4 ′, 4 ″ -tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4,4 ′, which is a low molecular organic compound, is used. , 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA), 4,4′-bis [N- (4-diphenylaminophenyl) -N-phenyl Amino] biphenyl (abbreviation: DPAB), 4,4′-bis (N- {4- [N ′-(3-methylphenyl) -N′-phenylamino] phenyl} -N-phenylamino) biphenyl (abbreviation: DNTPD), 1,3,5-tris [N- (4-diphenylaminophenyl) -N-phenylamino] benzene (abbreviation: DPA3B), 3- [N- (9-phenylcarbazole-3- ) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis [N- (9-phenylcarbazol-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation) : PCzPCA2), aromatic amine compounds such as 3- [N- (1-naphthyl) -N- (9-phenylcarbazol-3-yl) amino] -9-phenylcarbazole (abbreviation: PCzPCN1), and dipyrazino [2 , 3-f: 20,30-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN).

  As the substance having a high hole injecting property, a high molecular compound (an oligomer, a dendrimer, a polymer, or the like) can also be used. For example, poly (N-vinylcarbazole) (abbreviation: PVK), poly (4-vinyltriphenylamine) (abbreviation: PVTPA), poly [N- (4- {N ′-[4- (4-diphenylamino)] Phenyl] phenyl-N′-phenylamino} phenyl) methacrylamide] (abbreviation: PTPDMA), poly [N, N′-bis (4-butylphenyl) -N, N′-bis (phenyl) benzidine] (abbreviation: Polymer compounds such as Poly-TPD). In addition, a polymer compound to which an acid such as poly (3,4-ethylenedioxythiophene) / poly (styrenesulfonic acid) (PEDOT / PSS), polyaniline / poly (styrenesulfonic acid) (PAni / PSS) is added is used. You can also

(Hole transport layer)
The hole transport layer is a layer containing a substance having a high hole transport property. An aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used for the hole transport layer. Specifically, 4,4′-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) or N, 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 , 4′-bis [N- (9,9-dimethylfluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: DFLDPBi), 4,4 ′, 4 ″ -tris (N, N-diphenylamino) ) Triphenylamine (abbreviation: TDATA), 4,4 ′, 4 ″ -tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA), 4,4′-bis [N- (Spiro-9,9'-Biff Oren-2-yl) -N- phenylamino] biphenyl (abbreviation: BSPB) can be used aromatic amine compounds such as. The substances described here are mainly substances having a hole mobility of 10 ⁻⁶ cm ² / (V · s) or more.

  For the hole transport layer, CBP, 9- [4- (N-carbazolyl)] phenyl-10-phenylanthracene (CzPA), 9-phenyl-3- [4- (10-phenyl-9-anthryl) phenyl] A carbazole derivative such as -9H-carbazole (PCzPA) or an anthracene derivative such as t-BuDNA, DNA, or DPAnth may be used. A high molecular compound such as poly (N-vinylcarbazole) (abbreviation: PVK) or poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.

  Note that other than these substances, any substance that has a property of transporting more holes than electrons may be used. Note that the layer containing a substance having a high hole-transport property is not limited to a single layer, and two or more layers containing the above substances may be stacked.

  When two or more hole transport layers are arranged, it is preferable to arrange a material having a larger energy gap on the side closer to the light emitting layer. An example of such a material is HT-2 used in Examples described later.

(Electron transport layer)
The electron transport layer is a layer containing a substance having a high electron transport property. For the electron transport layer, 1) metal complexes such as aluminum complexes, beryllium complexes and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives and phenanthroline derivatives, and 3) polymer compounds Can be used. Specifically, as a low-molecular organic compound, Alq, tris (4-methyl-8-quinolinolato) aluminum (abbreviation: Almq ₃ ), bis (10-hydroxybenzo [h] quinolinato) beryllium (abbreviation: BeBq ₂ ), A metal complex such as BAlq, Znq, ZnPBO, ZnBTZ, or the like can be used. In addition to metal complexes, 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis [5- (Pert-butylphenyl) -1,3,4-oxadiazol-2-yl] benzene (abbreviation: OXD-7), 3- (4-tert-butylphenyl) -4-phenyl-5- (4- Biphenylyl) -1,2,4-triazole (abbreviation: TAZ), 3- (4-tert-butylphenyl) -4- (4-ethylphenyl) -5- (4-biphenylyl) -1,2,4- Triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproin (abbreviation: BCP), 4,4′-bis (5-methylbenzoxazol-2-yl) stilbene (abbreviation: B) Heteroaromatic compounds such as zOs) can also be used. In this embodiment, a benzimidazole compound can be suitably used. The substances described here are mainly substances having an electron mobility of 10 ⁻⁶ cm ² / (V · s) or more. Note that any substance other than the above substances may be used for the electron-transport layer as long as it has a higher electron-transport property than the hole-transport property. In addition, the electron transport layer may be composed of a single layer, or may be composed of two or more layers made of the above substances.

  Moreover, a high molecular compound can also be used for an electron carrying layer. For example, poly [(9,9-dihexylfluorene-2,7-diyl) -co- (pyridine-3,5-diyl)] (abbreviation: PF-Py), poly [(9,9-dioctylfluorene-2) , 7-diyl) -co- (2,2′-bipyridine-6,6′-diyl)] (abbreviation: PF-BPy) and the like can be used.

(Electron injection layer)
The electron injection layer is a layer containing a substance having a high electron injection property. For the electron injection layer, lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), lithium oxide (LiOx), etc. An alkali metal, an alkaline earth metal, or a compound thereof can be used. In addition, a substance in which an alkali metal, an alkaline earth metal, or a compound thereof is contained in a substance having an electron transporting property, specifically, a substance in which magnesium (Mg) is contained in Alq may be used. In this case, electron injection from the cathode can be performed more efficiently.

Alternatively, a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer. Such a composite material is excellent in electron injecting property and electron transporting property because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material excellent in transporting the generated electrons. Specifically, for example, a substance (metal complex, heteroaromatic compound, or the like) constituting the electron transport layer described above is used. be able to. The electron donor may be any substance that exhibits an electron donating property to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferable, and lithium, cesium, magnesium, calcium, erbium, ytterbium, and the like can be given. Alkali metal oxides and alkaline earth metal oxides are preferable, and lithium oxide, calcium oxide, barium oxide, and the like can be given. A Lewis base such as magnesium oxide can also be used. Alternatively, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can be used.
(Layer formation method)
The method for forming each layer of the organic EL element of the present embodiment is not limited except as specifically mentioned above, but a dry film forming method such as a vacuum evaporation method, a sputtering method, a plasma method, an ion plating method, a spin method, A known method such as a coating method, a dipping method, a flow coating method, or a wet film forming method such as an ink jet method can be adopted.

(Film thickness)
The film thickness of each organic layer of the organic EL element of the present embodiment is not limited except as specifically mentioned above. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur, and conversely, if it is too thick, it is high. Since an applied voltage is required and the efficiency is deteriorated, the range of several nm to 1 μm is usually preferable.

[Electronics]
The electronic device of this embodiment is equipped with the organic EL element of this embodiment. Examples of the electronic device include a display device and a light emitting device. Examples of the display device include display components (for example, an organic EL panel module), a television, a mobile phone, a tablet, and a personal computer. Examples of the light emitting device include lighting and vehicle lamps.

  In the present specification, a numerical range expressed using “to” means a range including a numerical value described before “to” as a lower limit value and a numerical value described after “to” as an upper limit value. To do.

In this specification, Rx and Ry are bonded to each other to form a ring. For example, Rx and Ry include a carbon atom, a nitrogen atom, an oxygen atom, a sulfur atom, or a silicon atom, and an atom (carbon atom) contained in Rx. , A nitrogen atom, an oxygen atom, a sulfur atom or a silicon atom) and an atom (carbon atom, nitrogen atom, oxygen atom, sulfur atom or silicon atom) contained in Ry is a single bond, a double bond, a triple bond, or It means that they are bonded via a divalent linking group to form a ring having 5 or more ring carbon atoms (specifically, a heterocyclic ring or an aromatic hydrocarbon ring). x is a number, a letter, or a combination of a number and a letter. y is a number, a letter, or a combination of a number and a letter.
There is no particular restriction on the divalent linking group, _{e.g., -O -, - CO -,} - CO 2 -, - S -, - SO -, - SO 2 -, - NH -, - NRa-, and their And a combination of two or more linking groups.
Specific examples of the heterocyclic ring include a ring structure (heterocycle) in which a bond is removed from the “heteroaryl group having 5 to 30 ring atoms” exemplified in “Description of each substituent in the general formula” described later. Is mentioned. These heterocycles may have a substituent.
Specific examples of the aromatic hydrocarbon ring include a ring structure in which a bond is removed from the “aryl group having 6 to 30 ring carbon atoms” exemplified in “Description of each substituent in the general formula” described later. Group hydrocarbon ring). These aromatic hydrocarbon rings may have a substituent.
Examples of Ra include a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted hetero ring having 5 to 30 ring atoms. An aryl group etc. are mentioned.
For example, Rx and Ry are bonded to each other to form a ring. In the molecular structure represented by the following general formula (E1), an atom contained in Rx ₁ and an atom contained in Ry ₁ are represented by the general formula ( Forming a ring (ring structure) E represented by E2); in the molecular structure represented by the general formula (F1), an atom contained in Rx ₁ and an atom contained in Ry ₁ are represented by the general formula ( to form a ring F represented by F2); in the molecular structure represented by the general formula (G1), and atoms contained in Rx _1, and the atoms contained in Ry _1, Table general formula (G2) Forming a ring G; in the molecular structure represented by the general formula (H1), an atom contained in Rx ₁ and an atom contained in Ry ₁ are represented by the ring H represented by the general formula (H2) In the molecular structure represented by the general formula (I1), included in Rx ₁ And the atom contained in Ry ₁ form a ring I represented by the general formula (I2).
In the general formulas (E1) to (I1), * each independently represents a bonding position with another atom in one molecule. Two * in general formula (E1) correspond to two * in general formula (E2), respectively, and two * in general formula (F1) respectively correspond to two * in general formula (F2) And two * in the general formula (G1) correspond to two * in the general formula (G2), respectively, and two * in the general formula (H1) correspond to two * in the general formula (H2). The two * s in the general formula (I1) correspond to the two * s in the general formula (I2), respectively.

  In the molecular structures represented by the general formulas (E2) to (I2), E to I each represent a ring structure (the ring having 5 or more ring-forming atoms). In the general formulas (E2) to (I2), * each independently represents a bonding position with another atom in one molecule. Two * in the general formula (E2) correspond to two * in the general formula (E1), respectively. Similarly, the two * 's in the general formulas (F2) to (I2) correspond to the two *' s in the general formulas (F1) to (I1), respectively.

For example, in general formula (E1), when Rx ₁ and Ry ₁ are bonded to each other to form ring E in general formula (E2), and ring E is an unsubstituted benzene ring, in general formula (E1) The molecular structure represented is the molecular structure represented by the following general formula (E3). Here, two * in the general formula (E3) each independently correspond to two * in the general formula (E2) and the general formula (E1).
For example, in general formula (E1), when Rx ₁ and Ry ₁ are bonded to each other to form ring E in general formula (E2), and ring E is an unsubstituted pyrrole ring, in general formula (E1) The molecular structure represented is the molecular structure represented by the following general formula (E4). Here, two * in the general formula (E4) independently correspond to two * in the general formula (E2) and the general formula (E1). In the general formulas (E3) and (E4), * each independently represents a bonding position with another atom in one molecule.

  In this specification, the number of ring-forming carbon atoms constitutes the ring itself of a compound having a structure in which atoms are bonded cyclically (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, or a heterocyclic compound). Represents the number of carbon atoms in the atom. 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 “ring-forming carbon number” described below is the same unless otherwise specified. For example, the benzene ring has 6 ring carbon atoms, the naphthalene ring has 10 ring carbon atoms, the pyridinyl group has 5 ring carbon atoms, and the furanyl group has 4 ring carbon atoms. Further, when an alkyl group is substituted as a substituent on the benzene ring or naphthalene ring, the carbon number of the alkyl group is not included in the number of ring-forming carbons. In addition, for example, when a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring), the carbon number of the fluorene ring as a substituent is not included in the number of ring-forming carbons.

  In the present specification, the number of ring-forming atoms means a compound (for example, a monocyclic compound, a condensed ring compound, a bridging compound, a carbocyclic compound, a heterocycle) having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic ring, a condensed ring, or a ring assembly). Of the ring compound) represents the number of atoms constituting the ring itself. Atoms that do not constitute a ring or atoms included in a substituent when the ring is substituted by a substituent are not included in the number of ring-forming atoms. The “number of ring-forming atoms” described below is the same unless otherwise specified. For example, the pyridine ring has 6 ring atoms, the quinazoline ring has 10 ring atoms, and the furan ring has 5 ring atoms. A hydrogen atom bonded to a carbon atom of a pyridine ring or a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms. Further, when, for example, a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring), the number of atoms of the fluorene ring as a substituent is not included in the number of ring-forming atoms.

・ Description of each substituent in the general formula in this specification (Description of each substituent)
Examples of the aryl group having 6 to 30 ring carbon atoms in this specification (sometimes referred to as an aromatic hydrocarbon group) include a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, and a phenanthryl group. , Fluorenyl group, pyrenyl group, chrysenyl group, fluoranthenyl group, benzo [a] anthryl group, benzo [c] phenanthryl group, triphenylenyl group, benzo [k] fluoranthenyl group, benzo [g] chrysenyl group, benzo [g b] A triphenylenyl group, a picenyl group, a perylenyl group, and the like.

  As an aryl group in this specification, it is preferable that ring forming carbon number is 6-20, It is more preferable that it is 6-14, It is further more preferable that it is 6-12. Among the aryl groups, a phenyl group, a biphenyl group, a naphthyl group, a phenanthryl group, a terphenyl group, and a fluorenyl group are even more preferable. For the 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group and 4-fluorenyl group, a 9-position carbon atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms in the present specification described later, It is preferable that the substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms is substituted.

  In the present specification, a heteroaryl group having 5 to 30 ring atoms (sometimes referred to as a heterocyclic group, a heteroaromatic ring group, or an aromatic heterocyclic group) has nitrogen, sulfur, oxygen as a heteroatom. Preferably, it contains at least any atom selected from the group consisting of silicon, selenium atoms, and germanium atoms, and more preferably contains at least any atom selected from the group consisting of nitrogen, sulfur, and oxygen. preferable.

  Examples of the heterocyclic group having 5 to 30 ring atoms in the present specification include, for example, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridazinyl group, triazinyl group, quinolyl group, isoquinolinyl group, naphthyridinyl group, phthalazinyl group, quinoxalinyl group, Quinazolinyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, indolyl group, benzimidazolyl group, indazolyl group, imidazolpyridinyl group, benz Triazolyl group, carbazolyl group, furyl group, thienyl group, oxazolyl group, thiazolyl group, isoxazolyl group, isothiazolyl group, oxadiazolyl group, thiadiazolyl group, benzofuranyl group, benzothienyl group, benzooxazolyl group, Nzothiazolyl group, benzoisoxazolyl group, benzisothiazolyl group, benzoxiadiazolyl group, benzothiadiazolyl group, dibenzofuranyl group, dibenzothienyl group, piperidinyl group, pyrrolidinyl group, piperazinyl group, morpholyl group, phenazinyl Group, phenothiazinyl group, phenoxazinyl group and the like.

  In the present specification, the number of ring-forming atoms of the heterocyclic group is preferably 5 to 20, and more preferably 5 to 14. Among the above heterocyclic groups, 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothienyl group, 2-dibenzothienyl group, 3-dibenzothienyl group Even more preferred are the group, 4-dibenzothienyl group, 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, and 9-carbazolyl group. For the 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group and 4-carbazolyl group, the 9-position nitrogen atom has a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms in the present specification, It is preferable that a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms is substituted.

  In the present specification, the heterocyclic group may be, for example, a group derived from a partial structure represented by the following general formulas (XY-1) to (XY-18).

In the general formulas (XY-1) to (XY-18), X _A and Y _A are each independently a hetero atom, and are an oxygen atom, a sulfur atom, a selenium atom, a silicon atom, or a germanium atom. Is preferred. The partial structures represented by the general formulas (XY-1) to (XY-18) have a bond at an arbitrary position to be a heterocyclic group, and this heterocyclic group has a substituent. Also good.

  Further, in this specification, as the substituted or unsubstituted carbazolyl group, for example, a ring is further condensed to a carbazole ring as represented by the following general formulas (XY-19) to (XY-22). Groups can also be included. Such a group may also have a substituent. Also, the position of the joint can be changed as appropriate.

  In the present specification, the alkyl group having 1 to 30 carbon atoms may be linear, branched or cyclic. Further, it may be a halogenated alkyl group.

  Examples of the linear or branched alkyl group include a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, amyl group, isoamyl group, 1-methylpentyl group, 2-methylpentyl group, 1-pentylhexyl group, 1-butylpentyl group, 1- A heptyloctyl group, a 3-methylpentyl group, etc. are mentioned.

  In the present specification, the linear or branched alkyl group preferably has 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms. Among the linear or branched alkyl groups, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group, n-pentyl group, n-hexyl group Even more preferred are amyl groups, isoamyl groups, and neopentyl groups.

  Examples of the cyclic alkyl group in the present specification include a cycloalkyl group having 3 to 30 ring carbon atoms.

  Examples of the cycloalkyl group having 3 to 30 ring carbon atoms in the present specification include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, an adamantyl group, and a norbornyl group. The ring-forming carbon number of the cycloalkyl group is preferably 3 to 10, and more preferably 5 to 8. Among the cycloalkyl groups, a cyclopentyl group and a cyclohexyl group are even more preferable.

  Examples of the halogenated alkyl group in which the alkyl group in the present specification is substituted with a halogen atom include a group in which the alkyl group having 1 to 30 carbon atoms is substituted with one or more halogen atoms, preferably a fluorine atom. .

  Examples of the halogenated alkyl group having 1 to 30 carbon atoms in the present specification include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a trifluoromethylmethyl group, a trifluoroethyl group, and a pentafluoroethyl group. Is mentioned.

  Examples of the substituted silyl group in the present specification include an alkylsilyl group having 3 to 30 carbon atoms and an arylsilyl group having 6 to 30 ring carbon atoms.

  Examples of the alkylsilyl group having 3 to 30 carbon atoms in the present specification include a trialkylsilyl group having an alkyl group exemplified as the alkyl group having 1 to 30 carbon atoms, specifically, a trimethylsilyl group and a triethylsilyl group. , Tri-n-butylsilyl group, tri-n-octylsilyl group, triisobutylsilyl group, dimethylethylsilyl group, dimethylisopropylsilyl group, dimethyl-n-propylsilyl group, dimethyl-n-butylsilyl group, dimethyl-t- Examples thereof include a butylsilyl group, a diethylisopropylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, and a triisopropylsilyl group. The three alkyl groups in the trialkylsilyl group may be the same as or different from each other.

  Examples of the arylsilyl group having 6 to 30 ring carbon atoms in the present specification include a dialkylarylsilyl group, an alkyldiarylsilyl group, and a triarylsilyl group.

  The dialkylarylsilyl group includes, for example, a dialkylarylsilyl group having two alkyl groups exemplified for the alkyl group having 1 to 30 carbon atoms and one aryl group having 6 to 30 ring carbon atoms. . The carbon number of the dialkylarylsilyl group is preferably 8-30.

  Examples of the alkyldiarylsilyl group include an alkyldiarylsilyl group having one alkyl group exemplified for the alkyl group having 1 to 30 carbon atoms and two aryl groups having 6 to 30 ring carbon atoms. . The alkyldiarylsilyl group preferably has 13 to 30 carbon atoms.

  Examples of the triarylsilyl group include a triarylsilyl group having three aryl groups having 6 to 30 ring carbon atoms. The carbon number of the triarylsilyl group is preferably 18-30.

In the present specification, an alkyl sulfonyl group _is represented by _-SO 2 _{R w. R w} in -SO ₂ R _w represents a substituted or unsubstituted alkyl group.

The substituted or unsubstituted alkylsulfonyl group having 1 to 30 carbon atoms in the present specification, R _w in the -SO ₂ R _w is a group which is substituted or unsubstituted alkyl groups of 1 to 30 carbon atoms Can be mentioned.

  In this specification, the aryl group in the aralkyl group (sometimes referred to as an arylalkyl group) is an aromatic hydrocarbon group or a heterocyclic group.

The aralkyl group having from 7 to 30 carbon atoms herein, is preferably a group having an aryl group of ring formation having 6 to 30 carbon atoms, it denoted _-Z 3 -Z _4. Examples of this Z ₃ include an alkylene group corresponding to the alkyl group having 1 to 30 carbon atoms. Examples of Z ₄ include, for example, examples of the aryl group having 6 to 30 ring carbon atoms. In the aralkyl group, the aryl moiety has 6 to 30 carbon atoms (preferably 6 to 20, more preferably 6 to 12), and the alkyl moiety has 1 to 30 carbon atoms (preferably 1 to 20, more preferably 1 to 10, More preferably, it is 1-6). Examples of the aralkyl group include benzyl group, 2-phenylpropan-2-yl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, and phenyl-t-butyl. Group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β- Examples include naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.

Alkoxy group having 1 to 30 carbon atoms herein, denoted -OZ _1. Examples of _{Z 1,} include alkyl groups of 1 to 30 carbon atoms. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and a hexyloxy group. The alkoxy group preferably has 1 to 20 carbon atoms.

  As a halogenated alkoxy group by which the alkoxy group was substituted by the halogen atom, the group by which the said C1-C30 alkoxy group was substituted by the 1 or more fluorine atom is mentioned, for example.

  In the present specification, the aryl group in the aryloxy group (sometimes referred to as an arylalkoxy group) includes a heteroaryl group.

Arylalkoxy groups forming the ring having 6 to 30 carbon atoms herein is expressed as -OZ _2. Examples of Z _2, for example, an aryl group of the ring-forming having 6 to 30 carbon atoms can be mentioned. The ring-forming carbon number of the arylalkoxy group is preferably 6-20. Examples of the arylalkoxy group include a phenoxy group.

Substituted amino groups herein are represented as -NHR _V or -N _{(R V) 2,.} The examples of R _V, for example, alkyl groups of 1 to 30 carbon atoms, and an aryl group of the ring-forming having 6 to 30 carbon atoms can be mentioned.

  In the present specification, the alkenyl group having 2 to 30 carbon atoms is either a straight chain or a branched chain, for example, vinyl group, propenyl group, butenyl group, oleyl group, eicosapentaenyl group, docosahexaenyl group. , A styryl group, a 2,2-diphenylvinyl group, a 1,2,2-triphenylvinyl group, a 2-phenyl-2-propenyl group, and the like.

  In the present specification, the alkynyl group having 2 to 30 carbon atoms may be linear or branched, and examples thereof include ethynyl, propynyl, and 2-phenylethynyl.

Arylthio group in an alkylthio group or ring form C6-30 C1-30 herein is expressed as -SR _V. The examples of R _V, include alkyl groups and aryl groups of the ring-forming C6-30 the C1-30. The alkylthio group preferably has 1 to 20 carbon atoms. The ring-forming carbon number of the arylthio group is preferably 6-20.

  As a halogen atom in this specification, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. are mentioned, A fluorine atom is preferable.

  Examples of the substituted phosphino group in the present specification include a phenylphosphanyl group.

  In the present specification, an arylcarbonyl group having 6 to 30 ring carbon atoms is represented by -COY '. Examples of Y ′ include the above-mentioned “aryl group having 6 to 30 ring carbon atoms”. Examples of the arylcarbonyl group having 6 to 30 ring carbon atoms in the present specification include a phenylcarbonyl group, a diphenylcarbonyl group, a naphthylcarbonyl group, and a triphenylcarbonyl group.

  In the present specification, an acyl group having 2 to 31 carbon atoms is represented as -COR '. Examples of R ′ include the above-described alkyl group having 1 to 30 carbon atoms. Examples of the acyl group having 2 to 31 carbon atoms in the present specification include an acetyl group and a propionyl group.

  The substituted phosphoryl group in this specification is represented by the following general formula (P).

As an ester group in this specification, group represented by -C (= O) OR ^E is mentioned, for example. Examples of R ^E is a substituted or unsubstituted ring forming aryl group having 6 to 18 carbon atoms (preferably having 6 to 10 ring carbon) and the.

  The siloxanyl group in the present specification is a silicon compound group via an ether bond, and examples thereof include a trimethylsiloxanyl group.

In the general formula (P), as Ar _P1 and Ar _P2 , an alkyl group having 1 to 30 carbon atoms (preferably 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms), and 6 to 6 carbon atoms forming a ring Any substituent selected from the group consisting of 30 (preferably 6-20, more preferably 6-14, ring carbon atoms) aryl groups, and the like can be mentioned. As an example of a C1-C30 alkyl group, the above-mentioned C1-C30 alkyl group is mentioned. Examples of the aryl group having 6 to 30 ring carbon atoms include the above-described aryl groups having 6 to 30 ring carbon atoms.

  In the present specification, “ring-forming carbon” means a carbon atom constituting a saturated ring, an unsaturated ring, or an aromatic ring. “Ring-forming atom” means a carbon atom and a hetero atom constituting a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring).

  In the present specification, the hydrogen atom includes isotopes having different neutron numbers, that is, light hydrogen (Protium), deuterium (Deuterium), and tritium (Tritium).

In this specification, the substituent in the case of “substituted or unsubstituted” includes an aryl group having 6 to 30 ring carbon atoms, a heteroaryl group having 5 to 30 ring atoms, and a straight chain having 1 to 30 carbon atoms. Chain alkyl group, branched alkyl group having 3 to 30 carbon atoms, cycloalkyl group having 3 to 30 ring carbon atoms, halogenated alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted silyl group (for example, carbon An alkylsilyl group having 3 to 30 carbon atoms, an arylsilyl group having 6 to 30 ring carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, and a substituted or unsubstituted amino group. , An alkylthio group having 1 to 30 carbon atoms, an arylthio group having 6 to 30 ring carbon atoms, an aralkyl group having 7 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a halogen atom, and 2 to 3 carbon atoms Alkynyl group, a cyano group, a hydroxy group, a nitro group, and at least one group selected from the group consisting of a carboxy group and a substituted phosphoryl group,.
However, the substituent E in the case of “substituted or unsubstituted” in the third compound is preferably not the heteroaryl group having 5 to 30 ring atoms and a substituted or unsubstituted amino group.
In the present specification, examples of the substituent in the case of “substituted or unsubstituted” include a diarylboron group (Ar _B1 Ar _B2 B—). Examples of Ar _B1 and Ar _B2 include the above-mentioned “aryl group having 6 to 30 ring carbon atoms”.
Specific examples and preferred groups of the substituent in the case of “substituted or unsubstituted” include the same groups as the specific examples and preferred groups of the substituent in “Description of each substituent”.

  The substituent E in the case of “substituted or unsubstituted” in the third compound is an aryl group having 6 to 30 ring carbon atoms (preferably 6 to 12 ring carbon atoms), 1 to 30 carbon atoms (preferably Is a linear alkyl group having 1 to 6 carbon atoms, a branched alkyl group having 3 to 30 carbon atoms (preferably 3 to 6 carbon atoms), and a halogen having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms). And at least one group selected from the group consisting of a cycloalkyl group having 3 to 30 ring carbon atoms (preferably 3 to 12 ring carbon atoms) is preferred. Specific substituents that are preferred are preferred.

  The substituent E may further have a substituent F. As the substituent F, an aryl group having 6 to 30 ring carbon atoms, an alkyl group having 1 to 30 carbon atoms, a halogenated alkyl group having 1 to 30 carbon atoms, a cycloalkyl group having 3 to 30 ring carbon atoms, silyl Group, an alkoxy group having 1 to 30 carbon atoms, a halogenated alkoxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, an alkylthio group having 1 to 30 carbon atoms, an arylthio having 6 to 30 ring carbon atoms A group consisting of a group, an aralkyl group having 7 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, a halogen atom, an alkynyl group having 2 to 30 carbon atoms, a cyano group, a hydroxy group, a nitro group, and a carboxy group. At least one group selected is preferred. However, the substituent F has no further substituents. The substituent F is preferably at least one group selected from the specific substituents preferred in the description of each substituent.

  As the substituent in the case of “substituted or unsubstituted” in the first compound, the second compound, and the fourth compound, the substituent has 6 to 30 ring carbon atoms (preferably 6 to 12 ring carbon atoms). An aryl group, a heteroaryl group having 5 to 30 ring atoms (preferably 5 to 12 ring atoms), a linear alkyl group having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms), and 3 to 3 carbon atoms A branched alkyl group having 30 (preferably 3 to 6 carbon atoms), a halogenated alkyl group having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms), and a ring forming carbon number of 3 to 30 (preferably ring forming) At least one group selected from the group consisting of cycloalkyl groups having 3 to 12 carbon atoms is preferable, and specific substituents that are preferable in the description of each substituent are preferable.

  In the first compound, the second compound, and the fourth compound, the substituent in the case of “substituted or unsubstituted” is an aryl group having 6 to 30 ring carbon atoms or a hetero ring having 5 to 30 ring atoms. Aryl group, linear alkyl group having 1 to 30 carbon atoms, branched alkyl group having 3 to 30 carbon atoms, cycloalkyl group having 3 to 30 ring carbon atoms, halogenated alkyl group having 1 to 30 carbon atoms, carbon An alkylsilyl group having 3 to 30 carbon atoms, an arylsilyl group having 6 to 30 ring carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 ring carbon atoms, a substituted amino group, and 1 to carbon atoms 30 alkylthio groups, arylthio groups having 6 to 30 ring carbon atoms, aralkyl groups having 7 to 30 carbon atoms, alkenyl groups having 2 to 30 carbon atoms, alkynyl groups having 2 to 30 carbon atoms, halogen atoms, cyano groups, Dorokishi group may be further substituted by at least one group selected from the group consisting of nitro groups and carboxy groups. A plurality of these substituents may be bonded to each other to form a ring.

The substituent in the case of “substituted or unsubstituted” in the first compound, the second compound, and the fourth compound may be further substituted with an aryl group having 6 to 30 ring carbon atoms, a ring At least one selected from the group consisting of a heteroaryl group having 5 to 30 atoms, a linear alkyl group having 1 to 30 carbon atoms, a branched alkyl group having 3 to 30 carbon atoms, a halogen atom, and a cyano group It is preferably a group, and more preferably at least one group selected from the specific substituents preferred in the description of each substituent.
Examples of the substituent further substituted with the substituent in the case of “substituted or unsubstituted” in the first compound, the second compound, and the fourth compound include an acyl group having 2 to 31 carbon atoms.

  The term “unsubstituted” in the case of “substituted or unsubstituted” means that a hydrogen atom is bonded without being substituted with the substituent.

  In this specification, “carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having XX to YY” represents the number of carbon atoms in the case where the ZZ group is unsubstituted and substituted. In this case, the number of carbon atoms in the substituent is not included.

  In this specification, “atom number XX to YY” in the expression “a ZZ group having a substituted or unsubstituted atom number XX to YY” represents the number of atoms when the ZZ group is unsubstituted and substituted. The number of atoms of the substituent in the case is not included.

  In the compound described in this specification or a partial structure thereof, the case of “substituted or unsubstituted” is the same as described above.

  In this specification, when substituents are bonded to each other to form a ring, the structure of the ring is a saturated ring, an unsaturated ring, an aromatic hydrocarbon ring, or a heterocyclic ring.

  In the present specification, examples of the aromatic hydrocarbon group and the heterocyclic group in the linking group include divalent or higher groups obtained by removing one or more atoms from the above-described monovalent group.

[Second Embodiment]
The configuration of the organic EL element according to the second embodiment will be described. In the description of the second embodiment, the same components as those in the first embodiment are denoted by the same reference numerals and names, and the description thereof is omitted or simplified. In the second embodiment, materials and compounds not particularly mentioned can be the same materials and compounds as those described in the first embodiment.

The organic EL device according to the second embodiment is different from the organic EL device according to the first embodiment in that the light emitting layer further includes a fourth compound. Other points are the same as in the first embodiment.
That is, in the second embodiment, the light emitting layer as the first organic layer includes the first compound, the second compound, and the fourth compound. The electron barrier layer as the second organic layer contains a third compound.
In this embodiment, the first compound is preferably a dopant material, the second compound is preferably a host material, and the fourth compound is preferably a host material. One of the second compound and the fourth compound may be referred to as a first host material, and the other may be referred to as a second host material.
It is also preferable that the fourth compound is a material in which a dopant material is dispersed in the light emitting layer as a third component.
The electron barrier layer is preferably disposed in contact with the light emitting layer.

(Fourth compound)
The fourth compound may be a thermally activated delayed fluorescent compound or a compound that does not exhibit thermally activated delayed fluorescence.
The singlet energy of the fourth compound is preferably larger than the singlet energy of the second compound.

  Although it does not specifically limit as a 4th compound, It is preferable that they are compounds other than an amine compound. For example, as the fourth compound, a derivative selected from the group consisting of a carbazole derivative, a dibenzofuran derivative, and a dibenzothiophene derivative can be used, but it is not limited to these derivatives.

  The fourth compound has, in one molecule, a partial structure represented by the following general formula (31), a partial structure represented by the following general formula (32), a partial structure represented by the following general formula (33), And a compound containing at least one of the partial structures represented by the following general formula (34).

In the general formula (31),
Y _{31 to} Y ₃₆ are each independently a nitrogen atom or a carbon atom bonded to another atom in the molecule of the fourth compound;
However, at least any one of Y _{31 to} Y ₃₆ is a carbon atom bonded to another atom in the molecule of the fourth compound,
In the general formula (32),
Y _{41 to} Y ₄₈ are each independently a nitrogen atom or a carbon atom bonded to another atom in the molecule of the fourth compound;
However, at least one of Y _{41 to} Y ₄₈ is a carbon atom bonded to another atom in the molecule of the fourth compound,
X ₃₀ is a nitrogen atom, an oxygen atom, or a sulfur atom that is bonded to another atom in the molecule of the fourth compound.
In the general formulas (33) to (34), * each independently represents a bonding point with another atom or another structure in the molecule of the fourth compound.

In the general formula (32), at least two of Y _{41 to} Y ₄₈ are carbon atoms bonded to other atoms in the molecule of the fourth compound, and a ring structure including the carbon atoms is constructed. Is also preferable.
For example, the partial structure represented by the general formula (32) includes the following general formula (321), general formula (322), general formula (323), general formula (324), general formula (325), and general formula. It is preferably any partial structure selected from the group consisting of the partial structures represented by (326).

In the general formulas (321) to (326),
X ₃₀ is each independently a nitrogen atom bonded to another atom in the molecule of the fourth compound, an oxygen atom, or a sulfur atom;
Y _{41 to} Y ₄₈ are each independently a nitrogen atom or a carbon atom bonded to another atom in the molecule of the fourth compound;
X ₃₁ is each independently a nitrogen atom, an oxygen atom, a sulfur atom, or a carbon atom bonded to another atom in the molecule of the fourth compound, which is bonded to another atom in the molecule of the fourth compound. ,
Y _{61 to} Y ₆₄ each independently represent a nitrogen atom or a carbon atom bonded to another atom in the molecule of the fourth compound.
In the present embodiment, the fourth compound preferably has a partial structure represented by the general formula (323) among the general formulas (321) to (326).

The partial structure represented by the general formula (31) is at least one group selected from the group consisting of a group represented by the following general formula (33) and a group represented by the following general formula (34). As a fourth compound.
The fourth compound preferably has at least one partial structure of the partial structures represented by the following general formula (33) and the following general formula (34). Since the bonding sites are located at the meta positions as in the partial structure represented by the following general formula (33) and the following general formula (34), the energy gap T _77K (Mat2) at 77 [K] of the fourth compound ) Can be kept high.

In the general formula (33), Y ₃₁ , Y ₃₂ , Y ₃₄ , and Y ₃₆ are each independently a nitrogen atom or CR ₃₁ .
In the general formula (34), Y ₃₂ , Y ₃₄ , and Y ₃₆ are each independently a nitrogen atom or CR ₃₁ .
In the general formulas (33) and (34),
Each of R ₃₁ is independently a hydrogen atom or a substituent;
R ₃₁ as a substituent is each independently
A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,
A substituted or unsubstituted silyl group,
Substituted germanium groups,
Substituted phosphine oxide groups,
Halogen atoms,
A cyano group,
It is selected from the group consisting of a nitro group and a substituted or unsubstituted carboxy group.
However, the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms in R ₃₁ is preferably a non-condensed ring.
In the general formula (33) and the general formula (34), * each independently represents a bonding point with another atom or another structure in the molecule of the fourth compound.

In the general formula (33), Y ₃₁ , Y ₃₂ , Y ₃₄ , and Y ₃₆ are preferably each independently CR ₃₁ , and the plurality of R ₃₁ are the same as or different from each other.
In the general formula (34), Y ₃₂ , Y ₃₄ , and Y ₃₆ are preferably each independently CR ₃₁ , and the plurality of R ₃₁ are the same as or different from each other.

The substituted germanium group is preferably represented by -Ge (R ₃₀₁ ) ₃ . R ₃₀₁ is each independently a substituent. The substituent R ₃₀₁ is preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms. The plurality of R ₃₀₁ are the same as or different from each other.

  The partial structure represented by the general formula (32) is at least one group selected from the group consisting of the following general formulas (35) to (39) and a group represented by the following general formula (30a). It is preferably contained in the fourth compound.

In the general formula (35), Y _{41 to} Y ₄₈ are each independently a nitrogen atom or CR ₃₂ .
In the general formulas (36) and (37), Y _{41 to} Y ₄₅ , Y ₄₇ , and Y ₄₈ are each independently a nitrogen atom or CR ₃₂ .
In the general formula (38), Y ₄₁ , Y ₄₂ , Y ₄₄ , Y ₄₅ , Y ₄₇ , and Y ₄₈ are each independently a nitrogen atom or CR ₃₂ .
In the general formula (39), Y _{42 to} Y ₄₈ are each independently a nitrogen atom or CR ₃₂ .
In the general formula (30a), Y _{42 to} Y ₄₇ are each independently a nitrogen atom or CR ₃₂ .
In the general formulas (35) to (39) and (30a),
Each R ₃₂ is independently a hydrogen atom or a substituent;
R ₃₂ as a substituent is
A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,
A substituted or unsubstituted silyl group,
Substituted germanium groups,
Substituted phosphine oxide groups,
Halogen atoms,
A cyano group,
Selected from the group consisting of a nitro group, and a substituted or unsubstituted carboxy group,
The plurality of R ₃₂ are the same as or different from each other.
In the general formulas (37) to (39) and (30a),
X ₃₀ is NR ₃₃ , an oxygen atom, or a sulfur atom,
R ₃₃ is
A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,
A substituted or unsubstituted silyl group,
Substituted germanium groups,
Substituted phosphine oxide groups,
Fluorine atom,
A cyano group,
Selected from the group consisting of a nitro group, and a substituted or unsubstituted carboxy group,
The plurality of R ₃₃ are the same as or different from each other.
However, the substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms in R ₃₃ is preferably a non-condensed ring.
In the general formulas (35) to (39) and (30a), * independently represents a bonding site with another atom or another structure in the molecule of the fourth compound.

In the general formula (35), Y _{41 to} Y ₄₈ are preferably each independently CR _{32. In the} general formula (36) and the general formula (37), Y _{41 to} Y ₄₅ , Y ₄₇ and Y ₄₈ are preferably each independently CR _{32. In the} general formula (38), Y ₄₁ , Y ₄₂ , Y ₄₄ , Y ₄₅ , Y ₄₇ , and Y ₄₈ are each independently , CR ₃₂ , and in the general formula (39), Y _{42 to} Y ₄₈ are preferably each independently CR ₃₂ , and in the general formula (30a), Y _{42 to} Y ₄₇ are Each independently is preferably CR ₃₂ , and the plurality of R ₃₂ may be the same as or different from each other.

In the fourth compound, X ₃₀ is preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.

In the fourth compound, R ₃₁ and R ₃₂ are each independently a hydrogen atom or a substituent, and R ₃₁ as a substituent and R ₃₂ as a substituent are each independently a fluorine atom, A cyano group, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms; It is preferably any group selected from the group consisting of R ₃₁ and R ₃₂ are a hydrogen atom, a cyano group, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms. Is more preferable. However, when R ₃₁ as a substituent and R ₃₂ as a substituent are a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, the aryl group is preferably a non-condensed ring.

  The fourth compound is preferably an aromatic hydrocarbon compound or an aromatic heterocyclic compound. Moreover, it is preferable that a 4th compound does not have a condensed aromatic hydrocarbon ring in a molecule | numerator.

-The manufacturing method of a 4th compound A 4th compound can be manufactured by the method as described in international publication 2012/153780, international publication 2013/038650, etc., for example. Further, for example, the second compound can be produced by using a known alternative reaction and a raw material according to the object.

  Examples of substituents in the fourth compound are as follows, for example, but the present invention is not limited to these examples.

Specific examples of aryl groups (sometimes referred to as aromatic hydrocarbon groups) include phenyl groups, tolyl groups, xylyl groups, naphthyl groups, phenanthryl groups, pyrenyl groups, chrysenyl groups, benzo [c] phenanthryl groups. , Benzo [g] chrysenyl group, benzoanthryl group, triphenylenyl group, fluorenyl group, 9,9-dimethylfluorenyl group, benzofluorenyl group, dibenzofluorenyl group, biphenyl group, terphenyl group, quarterphenyl Group, fluoranthenyl group and the like, preferably phenyl group, biphenyl group, terphenyl group, quarterphenyl group, naphthyl group, triphenylenyl group, fluorenyl group and the like.
Examples of the aryl group having a substituent include a tolyl group, a xylyl group, and a 9,9-dimethylfluorenyl group.
As specific examples indicate, aryl groups include both fused and non-fused aryl groups.
As the aryl group, a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, a naphthyl group, a triphenylenyl group, or a fluorenyl group is preferable.

Specific examples of the heteroaryl group (sometimes referred to as a heterocyclic group, a heteroaromatic ring group, or an aromatic heterocyclic group) include a pyrrolyl group, a pyrazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a pyridyl group. , Triazinyl group, indolyl group, isoindolyl group, imidazolyl group, benzimidazolyl group, indazolyl group, imidazol [1,2-a] pyridinyl group, furyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, azadibenzo Furanyl group, thiophenyl group, benzothienyl group, dibenzothienyl group, azadibenzothienyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, quinazolinyl group, naphthyridinyl group, carbazolyl group, azacarbazolyl group, phenanthridinyl group, acridinyl group, Phenantro Nyl group, phenazinyl group, phenothiazinyl group, phenoxazinyl group, oxazolyl group, oxadiazolyl group, furazanyl group, benzoxazolyl group, thienyl group, thiazolyl group, thiadiazolyl group, benzthiazolyl group, triazolyl group, tetrazolyl group, etc. Preferred examples include a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, an azadibenzofuranyl group, and an azadibenzothienyl group.
The heteroaryl group is preferably a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, an azadibenzofuranyl group, or an azadibenzothienyl group, and a dibenzofuranyl group, a dibenzothienyl group, An azadibenzofuranyl group or an azadibenzothienyl group is more preferable.

In the fourth compound, the substituted silyl group may be selected from the group consisting of a substituted or unsubstituted trialkylsilyl group, a substituted or unsubstituted arylalkylsilyl group, and a substituted or unsubstituted triarylsilyl group. preferable.
Specific examples of the substituted or unsubstituted trialkylsilyl group include a trimethylsilyl group and a triethylsilyl group.
Specific examples of the substituted or unsubstituted arylalkylsilyl group include a diphenylmethylsilyl group, a ditolylmethylsilyl group, and a phenyldimethylsilyl group.
Specific examples of the substituted or unsubstituted triarylsilyl group include a triphenylsilyl group and a tolylsilyl group.

In the fourth compound, the substituted phosphine oxide group is preferably a substituted or unsubstituted diarylphosphine oxide group.
Specific examples of the substituted or unsubstituted diarylphosphine oxide group include a diphenylphosphine oxide group and a ditolylphosphine oxide group.

  In the fourth compound, examples of the substituted carboxy group include a benzoyloxy group.

<Relationship between first compound, second compound, and fourth compound in light-emitting layer>
In the organic EL device of the present embodiment, the singlet energy S _{1 (Mat2)} of the second compound, a singlet energy S ₁ of the fourth compound _(MAT4), satisfies the following equation (Equation 2) It is preferable.
S ₁ (Mat 4)> S ₁ (Mat 2) (Equation 2)

The singlet energy S ₁ (Mat4) of the fourth compound is preferably larger than the singlet energy S ₁ (Mat1) of the first compound.

The energy gap T _77K (Mat 4) at 77 [K] of the fourth compound is preferably larger than the energy gap T _77K (Mat 1) at 77 [K] of the first compound.
The energy gap T _77K (Mat 4) at 77 [K] of the fourth compound is preferably larger than the energy gap T _77K (Mat 2) at 77 [K] of the second compound.

The singlet energy _S 1 of the first compound in the light-emitting layer (Mat1), a singlet energy _S 1 of the second compound (Mat2), a singlet energy _S 1 (Mat4) of the fourth compound, is It is preferable to satisfy the relationship of the following mathematical formula (Formula 3).
S ₁ (Mat 4)> S ₁ (Mat 2)> S ₁ (Mat ₁ ) (Equation 3)

It is preferable that the first compound, the second compound, and the fourth compound in the light emitting layer satisfy the relationship of the following mathematical formula (Formula 4).
T _77K (Mat 4)> T _77K (Mat 2)> T _77K (Mat 1) (Equation 4)

  When the organic EL device of the present embodiment emits light, it is preferable that mainly a fluorescent compound emits light in the light emitting layer.

-Content rate of the compound in a light emitting layer In the organic EL element of this embodiment, it is preferable that the content rate of a 1st compound is 0.01 mass% or more and 10 mass% or less in a light emitting layer, 0.01 mass % To 5% by mass, more preferably 0.01% to 1% by mass.
The content ratio of the second compound is preferably 10% by mass to 80% by mass, more preferably 10% by mass to 60% by mass, and further preferably 20% by mass to 60% by mass. preferable.
The content of the fourth compound is preferably 10% by mass or more and 80% by mass or less.
The upper limit of the total content of the first compound, the second compound, and the fourth compound in the light emitting layer is 100% by mass. In addition, this embodiment does not exclude that materials other than a 1st compound, a 2nd compound, and a 4th compound are contained in a light emitting layer.
The light emitting layer may contain only 1 type of 1st compounds, and may contain 2 or more types. The light emitting layer may contain only 1 type of 2nd compounds, and may contain 2 or more types. The light emitting layer may contain only 1 type of 4th compounds, and may contain 2 or more types.

FIG. 5 is a diagram illustrating an example of the relationship between the energy levels of the first compound, the second compound, and the fourth compound in the light emitting layer. In FIG. 5, S0 represents a ground state. S1 (Mat1) represents the lowest excited singlet state of the first compound, and T1 (Mat1) represents the lowest excited triplet state of the first compound. S1 (Mat2) represents the lowest excited singlet state of the second compound, and T1 (Mat2) represents the lowest excited triplet state of the second compound. S1 (Mat4) represents the lowest excited singlet state of the fourth compound, and T1 (Mat4) represents the lowest excited triplet state of the fourth compound. The broken-line arrow from S2 (Mat2) to S1 (Mat1) in FIG. 5 represents the Forster energy transfer from the lowest excited singlet state of the second compound to the lowest excited singlet state of the first compound. .
As shown in FIG. 5, when a compound having a small ΔST (Mat2) is used as the second compound, the lowest excited triplet state T1 (Mat2) is reversed to the lowest excited singlet state S1 (Mat2) by thermal energy. Intersection is possible. Then, the Forster energy transfer from the lowest excited singlet state S1 (Mat2) of the second compound to the first compound occurs, and the lowest excited singlet state S1 (Mat1) is generated. As a result, fluorescence emission from the lowest excited singlet state S1 (Mat1) of the first compound can be observed. It is believed that the internal quantum efficiency can theoretically be increased to 100% by utilizing delayed fluorescence due to this TADF mechanism.

According to the second embodiment, an organic EL element that emits light with high efficiency is realized.
The organic EL element which concerns on 2nd embodiment can be used for electronic devices, such as a display apparatus and a light-emitting device, similarly to the organic EL element which concerns on 1st embodiment.

[Modification of Embodiment]
In addition, this invention is not limited to the above-mentioned embodiment, The change in the range which can achieve the objective of this invention, improvement, etc. are contained in this invention.

For example, the light emitting layer is not limited to one layer, and a plurality of light emitting layers may be stacked. When the organic EL element has a plurality of light emitting layers, it is sufficient that at least one light emitting layer contains the first compound and the second compound. For example, the other light-emitting layer may be a fluorescent light-emitting layer or a phosphorescent light-emitting layer that utilizes light emission by electron transition from a triplet excited state to a direct ground state.
In addition, when the organic EL element has a plurality of light emitting layers, these light emitting layers may be provided adjacent to each other, or a so-called tandem organic material in which a plurality of light emitting units are stacked via an intermediate layer. It may be an EL element.

Moreover, the organic EL element of the said embodiment has an electron barrier layer (an example of a 2nd organic layer) between an anode and a light emitting layer.
By arranging the electron barrier layer in contact with the light emitting layer on the anode side of the light emitting layer, the electron barrier layer transports holes, and the electrons are on the anode side of the electron barrier layer (for example, holes) To reach the transport layer).
In the organic EL element of the present embodiment, for example, a hole barrier layer may be provided adjacent to the cathode side of the light emitting layer. The hole blocking layer is preferably disposed in contact with the light emitting layer and blocks at least one of holes and excitons.
For example, when a hole barrier layer is disposed in contact with the cathode side of the light emitting layer, the hole barrier layer transports electrons, and the holes are on the cathode side of the hole barrier layer (for example, electrons To reach the transport layer). When the organic EL element includes an electron transport layer, it is preferable to include the hole barrier layer between the light emitting layer and the electron transport layer.
In addition, barrier layers (a hole barrier layer and an electron barrier 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. By providing the barrier layer adjacent to the light emitting layer, excitons generated in the light emitting layer are prevented from moving to a layer (for example, an electron transport layer or a hole transport layer) closer to the electrode than the barrier layer. .
The light emitting layer and the barrier layer are preferably joined.

  In addition, the specific structure and shape in the implementation of the present invention may be other structures as long as the object of the present invention can be achieved.

  Examples according to the present invention will be described below. The present invention is not limited by these examples.

<Compound>
The compound used for manufacture of an organic EL element is shown below.

-Delayed fluorescence (delayed fluorescence of compound TADF1)
The delayed fluorescence was confirmed by measuring transient PL using the apparatus shown in FIG. The compound TADF1 and the compound TH-2 were co-evaporated on a quartz substrate so that the ratio of the compound TADF1 was 12% by mass, and a thin film having a thickness of 100 nm was formed to prepare a sample. Prompt light emission (immediate light emission) immediately observed from the excited state after excitation with pulsed light (light emitted from a pulse laser) absorbed by the compound TADF1, and observation immediately after the excitation There is a delay light emission (delayed light emission) that is not observed. The delayed fluorescence emission in this example means that the amount of delay emission (delayed emission) is 5% or more with respect to the amount of Promp emission (immediate emission). Specifically, the amount of Prompt luminescence (immediate emission) and _{X P,} the amount of Delay emission (delayed luminescence) is taken as _{X D,} that the value of X D / _{X P} is 0.05 or more means.
For compound TADF1, it was confirmed that the amount of delay luminescence (delayed luminescence) was 5% or more with respect to the amount of Promp luminescence (immediate luminescence). Specifically, it was confirmed that the value of X _D / X _P was 0.05 or more for the compound TADF1.
The amounts of Prompt light emission and Delay light emission can be obtained by the same method as described in “Nature 492, 234-238, 2012”. In addition, the apparatus used for calculation of the amount of Promp light emission and Delay light emission is not limited to the apparatus of FIG. 2, or the apparatus described in literature.

・ Singlet energy S ₁
Compound TADF1, singlet energy _{S 1} of compounds D1, and M1 were measured by the above-mentioned solution method.
The singlet energy S ₁ of the compound TADF1 was 2.37 eV.
Singlet energy _{S 1} of the compound D1 was 2.02 eV.
The singlet energy S ₁ of the compound M1 was 3.63 eV.

Main peak wavelength of compound A 5 μmol / L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the fluorescence spectrum of this sample at normal temperature (300 K) (vertical axis: fluorescence emission intensity, horizontal axis: wavelength) ) Was measured. In this example, the fluorescence spectrum was measured with a spectrophotometer manufactured by Hitachi (device name: F-7000). Note that the fluorescence spectrum measuring apparatus is not limited to the apparatus used here. In the fluorescence spectrum, the peak wavelength of the fluorescence spectrum that maximizes the emission intensity was taken as the main peak wavelength.
The main peak wavelength of the compound D1 was 609 nm.

<Production of red light emitting organic EL element>
A red light emitting organic EL element (hereinafter also referred to as a red light emitting element) was fabricated and evaluated as follows.

(Example 1)
A 25 mm × 75 mm × 1.1 mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatek Co., Ltd.) was subjected to ultrasonic cleaning for 5 minutes in isopropyl alcohol and then UV ozone cleaning for 1 minute. The film thickness of ITO was 130 nm.
The glass substrate with the transparent electrode line after the cleaning is mounted on a substrate holder of a vacuum deposition apparatus, and first, the compound HI1 is deposited so as to cover the transparent electrode on the surface on which the transparent electrode line is formed. A 5 nm hole injection layer was formed.
Next, the compound HT1 was vapor-deposited on the hole injection layer, and a hole transport layer having a thickness of 55 nm was formed on the HI1 film.
Next, a compound M22 as a third compound was vapor-deposited on the hole transport layer to form an electron barrier layer as a second organic layer having a thickness of 10 nm.
Next, a compound D1 as the first compound, a compound TADF1 as the second compound, and a compound M1 as the fourth compound are co-evaporated on the electron barrier layer, and a first film having a thickness of 25 nm is formed. A light emitting layer was formed as an organic layer. The concentration of the compound TADF1 in the light emitting layer was 10% by mass, the concentration of the compound D1 was 0.5% by mass, and the concentration of the compound M1 was 89.5% by mass.
Next, the compound M5 was vapor-deposited on this light emitting layer, and the 10-nm-thick 1st electron carrying layer was formed.
Next, the compound ET1 was vapor-deposited on the first electron transport layer to form a second electron transport layer having a thickness of 30 nm.
Next, lithium fluoride (LiF) was vapor-deposited on the second electron transporting layer to form an electron injecting electrode (cathode) having a thickness of 1 nm.
And metal aluminum (Al) was vapor-deposited on this electron injecting electrode, and the metal Al cathode with a film thickness of 80 nm was formed.
A device arrangement of the red light emitting device of Example 1 is schematically shown as follows.
ITO (130) / HI1 (5) / HT1 (55) / M22 (10) / M1: TADF1: D1 (25,89.5%: 10%: 0.5%) / M5 (10) / ET1 (30) / LiF ( 1) / Al (80)
The numbers in parentheses indicate the film thickness (unit: nm). Also, in the parentheses, the number expressed as a percentage indicates the ratio (mass%) of the fourth compound, the second compound, and the first compound in the light emitting layer. Hereinafter, the same notation is used.

(Comparative Example 1)
The red light emitting device of Comparative Example 1 was produced in the same manner as in Example 1 except that Compound M8 was used instead of Compound M22 in the electron barrier layer of Example 1.
The device configuration of the red light emitting device of Comparative Example 1 is schematically shown as follows.
ITO (130) / HI1 (5) / HT1 (55) / M8 (10) / M1: TADF1: D1 (25,89.5%: 10%: 0.5%) / M5 (10) / ET1 (30) / LiF ( 1) / Al (80)

(Comparative Example 2)
The red light emitting device of Comparative Example 2 was produced in the same manner as in Example 1 except that Compound M15 was used instead of Compound M22 in the electron barrier layer of Example 1.
The device configuration of the red light emitting device of the actual comparative example 2 is schematically shown as follows.
ITO (130) / HI1 (5) / HT1 (55) / M15 (10) / M1: TADF1: D1 (25,89.5%: 10%: 0.5%) / M5 (10) / ET1 (30) / LiF ( 1) / Al (80)

<Evaluation of red light emitting element>
The following evaluation was performed about the red light emitting element produced in Example 1 and Comparative Examples 1-2. The evaluation results are shown in Table 14. In Table 14, @ 0.1 indicates 0.1 mA / cm ² .

・ External quantum efficiency EQE
The spectral radiance spectrum when a voltage was applied to the device so that the current density was 0.1 mA / cm ² was measured with a spectral radiance meter CS-2000 (manufactured by Konica Minolta, Inc.).
The external quantum efficiency EQE (unit:%) was calculated from the obtained spectral radiance spectrum on the assumption that Lambtian radiation was performed.

-Values of chromaticity CIEx, CIEy, and main peak wavelength λ _p Spectral radiance spectrum when voltage is applied to the device so that the current density is 10 mA / cm ² is a spectral radiance meter CS-2000 (Konica Minolta Co., Ltd.) (Made by company). From the obtained spectral radiance spectrum, chromaticity CIEx, CIEy, and main peak wavelength λ _p (unit: nm) were calculated.

The first organic layer includes a first compound represented by the general formula (1) and a delayed fluorescent second compound, and the second organic layer is represented by the general formula (3). The red light-emitting device according to Example 1 containing the third compound showed higher external quantum efficiency than Comparative Examples 1 and 2 in which the second organic layer contained a compound not satisfying the general formula (3).
Therefore, according to the red light emitting device of the example, light was emitted with high efficiency.

  DESCRIPTION OF SYMBOLS 1 ... Organic EL element, 2 ... Board | substrate, 3 ... Anode, 4 ... Cathode, 5 ... Light emitting layer (an example of a 1st organic layer), 6 ... Hole injection layer, 7 ... Hole transport layer, 8 ... Electron transport Layer, 9 ... electron injection layer, 10 ... organic layer, 11 ... electron barrier layer (an example of a second organic layer).

Claims (29)

The anode,
A cathode,
A first organic layer included between the anode and the cathode;
A second organic layer included between the anode and the first organic layer,
The first organic layer includes a first compound and a second compound,
The second organic layer comprises a third compound;
The first compound is a compound represented by the following general formula (1),
The second compound is a delayed fluorescent compound,
The third compound is a compound represented by the following general formula (3).
Organic electroluminescence device.

(In the general formula (1),
X is a nitrogen atom or a carbon atom bonded to Y;
Y is a hydrogen atom or a substituent,
R _{21 to} R ₂₆ are each independently a hydrogen atom or a substituent, or a group of R ₂₁ and R _22, a group of R ₂₂ and R _23, a group of R ₂₄ and R ₂₅ , and R ₂₅ and R Any one or more of the ₂₆ groups are joined together to form a ring;
Y as a substituent and R _{21 to} R ₂₆ are each independently
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted C1-C30 halogenated alkoxy group,
A substituted or unsubstituted alkylthio group having 6 to 30 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,
A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,
A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,
Halogen atoms,
A carboxy group,
A substituted or unsubstituted ester group,
A substituted or unsubstituted carbamoyl group,
A substituted or unsubstituted amino group,
Nitro group,
A cyano group,
Selected from the group consisting of a substituted or unsubstituted silyl group, and a substituted or unsubstituted siloxanyl group,
Z ₂₁ and Z ₂₂ are each independently a substituent, or Z ₂₁ and Z ₂₂ are bonded to each other to form a ring,
Z ₂₁ and Z ₂₂ as substituents are each independently
Halogen atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
It is selected from the group consisting of a substituted or unsubstituted halogenated alkoxy group having 1 to 30 carbon atoms and a substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms. )

(In the general formula (3),
n is 1, 2, 3, or 4;
when n is 2, 3, or 4, the plurality of Cz are the same or different from each other;
X _B is a group represented by the following general formula (3A),
Cz is a group represented by the following general formula (3B-1) or (3B-2). )

(In the general formula (3A),
Ar ₁ is
Monovalent or polyvalent residues derived from substituted or unsubstituted dibenzofurans,
Monovalent or polyvalent residues derived from substituted or unsubstituted azadibenzofuran,
A monovalent or polyvalent residue derived from substituted or unsubstituted dibenzothiophene, or a monovalent or polyvalent residue derived from substituted or unsubstituted azadibenzothiophene,
Ar ₂ is independently
A monovalent or polyvalent residue derived from a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms,
Monovalent or polyvalent residues derived from substituted or unsubstituted dibenzofurans,
Monovalent or polyvalent residues derived from substituted or unsubstituted azadibenzofuran,
A monovalent or polyvalent residue derived from substituted or unsubstituted dibenzothiophene, or a monovalent or polyvalent residue derived from substituted or unsubstituted azadibenzothiophene,
k is 0, 1, 2, 3, or 4;
when k is 2, 3, or 4, the plurality of Ar ₂ are the same or different from each other;
In the case where Ar ₁ has a substituent, the substituent D 1 is independently
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,
A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted C1-C30 halogenated alkoxy group,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted silyl group,
Halogen atoms,
Selected from the group consisting of a cyano group and a nitro group,
The substituent D2 in the case where Ar ₂ has a substituent has the same meaning as the substituent D1,
When n is 1, Cz binds to Ar ₁
When n is 2, 3, or 4, a plurality of Cz are each independently bonded to Ar ₁ or bonded to Ar ₂ . However, at least one Cz is bonded to Ar ₁ . )

(In the general formula (3B-1),
X _{1 to} X ₈ are each independently a nitrogen atom or CR _A ,
R _A is a hydrogen atom or a substituent, or any one or more of the groups of adjacent R _A are bonded to each other to form a ring,
R _A as a substituent is each independently
A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted silyl group,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted C1-C30 halogenated alkoxy group,
A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,
Halogen atoms,
A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,
A cyano group,
A hydroxy group,
Selected from the group consisting of a nitro group and a carboxy group;
The plurality of R _A are the same or different from each other,
However, the nitrogen atom in the general formula (3B-1) is bonded to either Ar ₁ or Ar _{2 in} the general formula (3A). )

(In the general formula (3B-2),
Or X ₁ to X ₄ are the general formula (3A) in the carbon atom bonded to the one of Ar ₁ and Ar _2, a nitrogen atom or a CR _{C, R C} is a hydrogen atom or a substituent, or bonded to any one or more sets of pairs of _{R C} adjacent to each other to form a ring, provided _that one of X 1 to X ₄ are in the general formula (3A), Ar ₁ and Ar ₂ is a carbon atom bonded to any one of
X ₅ to X ₈ is a nitrogen atom or a CR _D, R _D is a hydrogen atom or a substituent, or adjacent R _D any one or more sets of pairs of mutually bonded each other to form a ring Form the
R _B , R _C and R _D are each independently synonymous with R _A in the general formula (3B-1), and the plurality of R _C are the same as or different from each other, and the plurality of R _D are The same or different,
In the third compound, the substituent E in the case of “substituted or unsubstituted” is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted C1-C30 halogenated alkoxy group,
A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,
A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,
Halogen atoms,
A carboxy group,
A substituted or unsubstituted amino group,
Nitro group,
A cyano group,
A substituted or unsubstituted silyl group,
A substituent selected from the group consisting of a substituted phosphoryl group and a hydroxy group;
When the substituent E further has a substituent F, the substituent F is
An unsubstituted aryl group having 6 to 30 ring carbon atoms,
An unsubstituted heteroaryl group having 5 to 30 ring atoms;
An unsubstituted alkyl group having 1 to 30 carbon atoms,
An unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
An unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
Unsubstituted silyl group,
An unsubstituted alkoxy group having 1 to 30 carbon atoms,
An unsubstituted halogenated alkoxy group having 1 to 30 carbon atoms,
An unsubstituted aryloxy group having 6 to 30 carbon atoms,
An unsubstituted alkylthio group having 1 to 30 carbon atoms,
An unsubstituted arylthio group having 6 to 30 ring carbon atoms,
An unsubstituted aralkyl group having 7 to 30 carbon atoms,
An unsubstituted alkenyl group having 2 to 30 carbon atoms,
Halogen atoms,
An unsubstituted alkynyl group having 2 to 30 carbon atoms,
A cyano group,
A hydroxy group,
Selected from the group consisting of a nitro group and a carboxy group, provided that substituent F has no further substituents. ) The organic electroluminescent device according to claim 1,
X _{1 to} X ₈ in the general formula (3B-1) are each independently CR _A ,
One of the _X 1 to X ₄ in the general formula (3B-2), each independently, a carbon atom bonded with any of Ar ₁ and Ar _2, or a CR _{C, however,} X 1 to X ₄ is in the general formula (3A), a carbon atom bonded with any of Ar ₁ and Ar _2, X 5 ~X ₈ are each independently CR _D,
Organic electroluminescence device. In the organic electroluminescent element according to claim 1 or 2,
In the general formula (3B-1), the groups of adjacent R _A are not bonded to each other,
In the general formula (3B-2), a set of R _C between adjacent are both not bind to each other, a set of R _D between adjacent are both not bond with each other,
Organic electroluminescence device. In the organic electroluminescent element according to any one of claims 1 to 3,
R _A in the general formula (3B-1) and R _B , R _C and R _D in the general formula (3B-2) are each independently
Hydrogen atom,
A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
A carbazolyl group,
A substituted carbazolyl group,
A halogen atom or a cyano group,
Organic electroluminescence device. In the organic electroluminescent element according to any one of claims 1 to 4,
R _A in the general formula (3B-1) and R _B , R _C and R _D in the general formula (3B-2) are each independently
A hydrogen atom, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
Organic electroluminescence device. In the organic electroluminescent element according to any one of claims 1 to 5,
R _A in the general formula (3B-1) and R _C and R _D in the general formula (3B-2) are hydrogen atoms.
Organic electroluminescence device. In the organic electroluminescent element according to any one of claims 1 to 6,
Cz in the general formula (3) is a group represented by the general formula (3B-1).
Organic electroluminescence device. In the organic electroluminescent element according to any one of claims 1 to 7,
N in the general formula (3) is 2.
Organic electroluminescence device. In the organic electroluminescent element according to any one of claims 1 to 8,
K in the general formula (3A) is 1.
Organic electroluminescence device. In the organic electroluminescent element according to any one of claims 1 to 9,
Ar ₁ in the general formula (3A) is a monovalent or polyvalent residue derived from a substituted or unsubstituted dibenzofuran, or a monovalent or polyvalent residue derived from a substituted or unsubstituted dibenzothiophene. And
Ar ₂ is independently a monovalent or polyvalent residue derived from a substituted or unsubstituted aromatic hydrocarbon group having 6 to 18 ring carbon atoms, a substituted or unsubstituted ring carbon number 6 to A monovalent or polyvalent residue derived from 18 dibenzofurans, or a monovalent or polyvalent residue derived from substituted or unsubstituted dibenzothiophene having 6 to 18 ring carbon atoms.
Organic electroluminescence device. In the organic electroluminescent element according to claim 10,
N in the general formula (3) is 2,
K in the general formula (3A) is 1, Ar ₁ is a monovalent or polyvalent residue derived from a substituted or unsubstituted dibenzofuran,
Ar ₂ is a monovalent or polyvalent residue derived from a substituted or unsubstituted aromatic hydrocarbon group having 6 to 12 ring carbon atoms.
Organic electroluminescence device. In the organic electroluminescent element according to any one of claims 1 to 11,
At least one of the plurality of Cz in the general formula (3) is bonded to Ar ₂ .
Organic electroluminescence device. In the organic electroluminescent element according to any one of claims 1 to 12,
Cz in the general formula (3) is any group selected from the group consisting of groups represented by the following formulas (3B11) to (3B22).
Organic electroluminescence device.


(In the groups represented by the formulas (3B11) to (3B22), the carbon atom that may have a substituent has the substituent X having the same meaning as R _A as the substituent, or has no substituent. In the case of having a plurality of substituents X, the plurality of substituents X are the same as or different from each other. The organic electroluminescence device according to claim 11,
Cz in the general formula (3) is any group selected from the group consisting of groups represented by the formulas (3B11) to (3B17).
Organic electroluminescence device. In the organic electroluminescent element according to any one of claims 1 to 14,
Z ₂₁ and Z ₂₂ are both fluorine atoms, or both are alkoxy groups having 1 to 30 carbon atoms substituted with fluorine atoms,
Organic electroluminescence device. In the organic electroluminescent element according to any one of claims 1 to 15,
Z ₂₁ and Z ₂₂ are both fluorine atoms.
Organic electroluminescence device. In the organic electroluminescent element according to any one of claims 1 to 14,
The first compound is a compound represented by the following general formula (10).
Organic electroluminescence device.

(In the general formula (10),
X is synonymous with X in the general formula (1), and Y when X is a carbon atom bonded to Y is synonymous with Y in the general formula (1);
R _{21 to} R ₂₆ are each independently synonymous with R _{21 to} R ₂₆ in the general formula (1),
L ₂₁ and L ₂₂ are each independently
A substituted or unsubstituted alkylene group having 1 to 6 carbon atoms, or a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms,
A ₂₁ and A ₂₂ are each independently
A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms,
A substituted or unsubstituted halogenated alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms,
m1 is an integer from 0 to 7, m2 is an integer from 0 to 7,
When m1 is an integer of 2 or more and 7 or less, the plurality of L ₂₁ are the same or different from each other. When m2 is an integer of 2 or more and 7 or less, the plurality of L ₂₂ are the same or different from each other, and m1 is 0. In this case, A ₂₁ is directly bonded to the oxygen atom, and when m2 is 0, A ₂₂ is directly bonded to the oxygen atom. ) The organic electroluminescence device according to claim 17,
The first compound is a compound represented by the following general formula (10a).
Organic electroluminescence device.

(In the general formula (10a),
X is synonymous with X in the general formula (1), and Y when X is a carbon atom bonded to Y is synonymous with Y in the general formula (1);
R _{21 to} R ₂₆ are each independently synonymous with R _{21 to} R ₂₆ in the general formula (1),
m3 is 0 or more and 4 or less,
m4 is 0 or more and 4 or less,
m3 and m4 are the same as or different from each other. ) In the organic electroluminescent element according to any one of claims 1 to 18,
X is a carbon atom bonded to Y;
Y is a hydrogen atom or a substituent,
Y as a substituent is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
When Y is an aryl group having 6 to 30 ring carbon atoms having a substituent, the substituent is
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted halogenated alkoxy group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 ring carbon atoms substituted with an alkyl group having 1 to 30 carbon atoms,
Organic electroluminescence device. In the organic electroluminescent element according to any one of claims 1 to 19,
R ₂₁ , R ₂₃ , R ₂₄ , and R ₂₆ are each independently
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or an aryl group having 6 to 30 ring carbon atoms substituted with an alkyl group having 1 to 30 carbon atoms;
R ₂₂ and R ₂₅ are hydrogen atoms,
Organic electroluminescence device. In the organic electroluminescent element according to any one of claims 1 to 20,
R ₂₁ , R ₂₃ , R ₂₄ , and R ₂₆ are each independently
A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms,
A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms substituted with an alkyl group having 1 to 6 carbon atoms;
R ₂₂ and R ₂₅ are hydrogen atoms,
Organic electroluminescence device. The organic electroluminescence device according to any one of claims 1 to 21,
The substituent in the case of "substituted or unsubstituted" in the first compound is
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted halogenated alkyl group having 1 to 30 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,
A substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms,
A substituted or unsubstituted C1-C30 halogenated alkoxy group,
A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms,
A substituted or unsubstituted aryloxy group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted arylthio group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms,
A substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms,
Halogen atoms,
A carboxy group,
A substituted or unsubstituted amino group,
Nitro group,
A cyano group,
A substituted or unsubstituted silyl group,
A substituted phosphoryl group and a substituent selected from the group consisting of a hydroxy group,
Organic electroluminescence device. In the organic electroluminescent element according to any one of claims 1 to 22,
The substituent in the case of "substituted or unsubstituted" in the first compound is
A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted heteroaryl group having 5 to 30 ring atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituent selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
Organic electroluminescence device. In the organic electroluminescent element according to any one of claims 1 to 23,
The substituent in the case of "substituted or unsubstituted" in the first compound is
A substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms,
A substituted or unsubstituted heteroaryl group having 5 to 12 ring atoms;
A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms,
A substituent selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms and a substituted or unsubstituted cycloalkyl group having 3 to 12 ring carbon atoms;
Organic electroluminescence device. In the organic electroluminescent element according to any one of claims 1 to 24,
The substituent E in the case of "substituted or unsubstituted" in the third compound is
A substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms,
A substituent selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms and a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms,
Organic electroluminescence device. In the organic electroluminescent element according to any one of claims 1 to 25,
The substituent E in the case of "substituted or unsubstituted" in the third compound is
A substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms,
A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms,
A substituent selected from the group consisting of a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms and a substituted or unsubstituted cycloalkyl group having 3 to 12 ring carbon atoms;
Organic electroluminescence device. In the organic electroluminescent element according to any one of claims 1 to 26,
The singlet energy _S 1 (Mat1) of said first compound, said second singlet energy _S 1 of the compound (Mat2), but satisfies the following equation (Equation 1),
Organic electroluminescence device.
S ₁ (Mat 2)> S ₁ (Mat 1) (Equation 1) In the organic electroluminescent element according to any one of claims 1 to 27,
The first organic layer further comprises a fourth compound;
The singlet energy _S 1 (Mat2) of said second compound, said fourth and singlet energy _S 1 of the compound (MAT4), but satisfies the following equation (Equation 2),
Organic electroluminescence device.
S ₁ (Mat 4)> S ₁ (Mat 2) (Equation 2)   An electronic device equipped with the organic electroluminescence element according to any one of claims 1 to 28.