JP2022030205A - Organic electroluminescent element and electronic apparatus - Google Patents

Abstract

To provide an organic electroluminescent element which has a long service life.SOLUTION: An organic electroluminescent element comprises: an anode 3; a cathode 4; a light emitting layer 5. The light emitting layer 5 comprises: a first compound; a second compound; and a third compound having the delayed fluorescence property. The first compound, the second compound and the third compound have mutually-different structures. A singlet energy S1(M1) of the first compound and a singlet energy S1(M3) of the third compound satisfy a relation of a formula (formula 1). A singlet energy S1(M2) of the second compound and the singlet energy S1(M3) of the third compound satisfy a relation of a formula (formula 2). S1(M1)>S1(M3) (formula 1). S1(M2)>S1(M3) (formula 2).SELECTED DRAWING: Figure 1

Description

The present invention relates to organic electroluminescence devices and electronic devices.

When a voltage is applied to an organic electroluminescence device (hereinafter, may be referred to as “organic EL device”), holes are injected into the light emitting layer from the anode and electrons are injected into the light emitting layer from the cathode. Then, in the light emitting layer, the injected holes and electrons are recombined to form excitons. At this time, according to the statistical law of electron spin, singlet excitons are generated at a rate of 25%, and triplet excitons are generated at a rate of 75%.
Fluorescent organic EL elements 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 are being made to improve the performance of the organic EL element.

For example, it is expected that an organic EL device will emit light more efficiently by using triplet excitons in addition to singlet excitons. Against this background, high-efficiency fluorescent organic EL devices using thermally activated delayed fluorescence (hereinafter, may be simply referred to as “delayed fluorescence”) have been proposed and studied.
The TADF (Thermally Activated Fluorescence, Thermally Activated Delayed Fluorescence) mechanism (mechanism) is from a triplet excitator to a singlet when a material with a small energy difference (ΔST) between the singlet level and the triplet level is used. It is a mechanism that utilizes the phenomenon that inverse intersystem crossing to term excitors occurs thermally. Thermally activated delayed fluorescence is described in, for example, "Chihaya Adachi," Device Properties of Organic Semiconductors, "Kodansha, April 1, 2012, pp. 261-268".
As a compound exhibiting thermally activated delayed fluorescence (hereinafter, also referred to as a TADF compound), for example, a compound in which a donor site and an acceptor site are bonded in a molecule is known.

Examples of documents relating to organic EL devices include Patent Document 1 and Patent Document 2.
Patent Document 1 discloses that a "first host material" and a "second host material" are used in a light emitting layer using a TADF-like compound. Patent Document 1 describes, in examples, as two "host materials", 3,3'-di (9H-carbazole-9-yl) -1,1-biphenyl (mCBP) and azines such as compound T2T. It is disclosed to use a compound having a ring.
Patent Document 2 discloses an organic EL device having a light emitting layer containing two types of host materials and a delayed fluorescent substance in a part of Examples. Of the two types of host materials contained in the organic EL device of the example of Patent Document 2, one is a compound having a triphenylene and a carbonyl group.

International Publication No. 2017/115833 International Publication No. 2016/035803

In order to improve the performance of electronic devices such as displays, there is a demand for further improvement in the performance of organic EL elements. Examples of the performance of the organic EL element include life, brightness, emission wavelength, chromaticity, luminous efficiency, and drive voltage.

An object of the present invention is to provide a long-life organic electroluminescence device, and to provide an electronic device equipped with the organic electroluminescence device.

According to one aspect of the present invention, the light emitting layer has an anode, a cathode, and a light emitting layer contained between the anode and the cathode, and the light emitting layer is represented by the following general formula (1). The first compound, the second compound and the third compound are different in structure from each other, and include one compound, a second compound, and a delayed fluorescent third compound, and the single term energy of the first compound. S ₁ (M1) and the single-term energy S ₁ (M3) of the third compound satisfy the relationship of the following formula (Equation 1), and the single-term energy S ₁ (M2) of the second compound and the above-mentioned Provided is an organic electroluminescence device in which the single term energy S ₁ (M3) of the third compound satisfies the relationship of the following mathematical formula (Equation 2).
S ₁ (M1)> S ₁ (M3) ... (Equation 1)
S ₁ (M2)> S ₁ (M3) ... (number 2)

(In the general formula (1),
R ₁₀₀ to R ₁₀₈ are independently hydrogen atoms, substituents, or pairs of R _100s , pairs of R ₁₀₀ and R ₁₀₁ , pairs of R ₁₀₁ and R ₁₀₂ , R ₁₀₂ and A set of R ₁₀₃ , a set of R ₁₀₃ and R ₁₀₄ , a set of R ₁₀₄ and R ₁₀₅ , a set of R ₁₀₅ and R ₁₀₆ , a set of R ₁₀₆ and R ₁₀₇ , a set of R ₁₀₇ and R ₁₀₈ , and a set of R ₁₀₈ and R. Any one or more pairs of ₁₀₀ pairs combine with each other to form a ring.
L ₁ is a single bond or linking group
L ₁ as a linking group is
A substituted or unsubstituted ring-forming arylene group having 6 to 25 carbon atoms,
A divalent heterocyclic group having 5 to 22 substituted or unsubstituted ring-forming atoms,
Two groups selected from the group consisting of an arylene group having 6 to 25 substituted or unsubstituted ring-forming carbon atoms and a divalent heterocyclic group having 5 to 22 substituted or unsubstituted ring-forming atoms are bonded to each other. Select from the group consisting of a divalent group to be formed, an arylene group having 6 to 25 substituted or unsubstituted ring-forming carbon atoms, and a divalent heterocyclic group having 5 to 22 substituted or unsubstituted ring-forming atoms. It is a divalent group formed by combining the three groups to be formed, and B ₁ is a hydrogen atom or a substituent.
R ₁₀₀ to R ₁₀₈ and B ₁ as substituents are independent of each other.
Halogen atom,
Cyano group,
Substituentally substituted or unsubstituted aryl groups having 6 to 50 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 50 atom-forming atoms,
Substituentally substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 30 carbon atoms,
Substituentally or unsubstituted alkynyl groups having 2 to 30 carbon atoms,
Substituentally substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
Substituentally substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms,
Substituentally substituted or unsubstituted arylphosphoryl groups having 6 to 60 carbon atoms,
Hydroxy group,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms,
-A group represented by N (R ₉₁₁ ) (R ₉₁₂ ),
Thiol group,
Substituentally substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted ring-forming aralkyl groups having 7 to 30 carbon atoms,
Substitute germanium group,
Substituted phosphine oxide group,
Nitro group,
A substituted boryl group or a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms.
p is 3, and the three _R100s are the same as or different from each other.
R ₉₁₁ and R ₉₁₂ are independent of each other.
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms.
However, the first compound represented by the general formula (1) does not have a carbonyl group in the molecule. )

According to one aspect of the present invention, there is provided an electronic device equipped with the organic electroluminescence device according to the above-mentioned aspect of the present invention.

According to one aspect of the present invention, it is possible to provide an organic electroluminescence device having excellent performance, particularly long life. According to one aspect of the present invention, it is possible to provide an electronic device equipped with the organic electroluminescence element.

It is a figure which shows the schematic structure of an example of the organic electroluminescence element which concerns on 1st Embodiment of this invention. It is a schematic diagram of the apparatus which measures a 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 of the 1st compound, the 2nd compound and the 3rd compound in the light emitting layer of an example of the organic electroluminescence element which concerns on 1st Embodiment of this invention. It is a figure which shows the relationship between the energy level of the 1st compound, the 2nd compound, the 3rd compound and the 4th compound, and the energy transfer in the light emitting layer of an example of the organic electroluminescence element which concerns on the 2nd Embodiment of this invention.

[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 electrodes of the anode and the cathode. This organic layer contains at least one layer composed of an organic compound. Alternatively, this organic layer is formed by laminating a plurality of layers composed of organic compounds. The organic layer may further contain an inorganic compound. In the organic EL device of the present embodiment, at least one of the organic layers is a light emitting layer. Therefore, the organic layer may be composed of, for example, one light emitting layer, or may include a layer that can be adopted in the organic EL element. The layer that can be adopted for the organic EL device is not particularly limited, but is selected from the group consisting of, for example, a hole injection layer, a hole transport layer, an electron barrier layer, an electron injection layer, an electron transport layer, and a hole barrier layer. At least one layer can be mentioned.
The organic EL element of the present embodiment has a light emitting layer included between the anode and the cathode.

The organic layer of the organic EL element of the present embodiment preferably has, for example, any of the following layer configurations.
・ Electron barrier layer / light emitting layer / hole barrier layer ・ hole injection layer / electron barrier layer / light emitting layer / hole barrier layer ・ hole transport layer / electron barrier layer / light emitting layer / hole barrier layer ・ hole injection Layer / hole transport layer / electron barrier layer / light emitting layer / hole barrier layer / electron barrier layer / light emitting layer / hole barrier layer / electron injection layer / electron barrier layer / light emitting layer / hole barrier layer / electron transport layer・ Electron barrier layer / light emitting layer / hole barrier layer / electron transport layer / electron injection layer ・ hole injection layer / electron barrier layer / light emitting layer / hole barrier layer / electron injection layer ・ hole injection layer / electron barrier layer / Light emitting layer / hole barrier layer / electron transport layer / hole injection layer / electron barrier layer / light emitting layer / hole barrier layer / electron transport layer / electron injection layer / hole transport layer / electron barrier layer / light emitting layer / Hole barrier layer / electron injection layer / hole transport layer / electron barrier layer / light emitting layer / hole barrier layer / electron transport layer / hole transport layer / electron barrier layer / light emitting layer / hole barrier layer / electron transport layer / Electron injection layer / hole injection layer / hole transport layer / electron barrier layer / light emitting layer / hole barrier layer / electron injection layer / hole injection layer / hole transport layer / electron barrier layer / light emitting layer / hole Barrier layer / electron transport layer / hole injection layer / hole transport layer / electron barrier layer / light emitting layer / hole barrier layer / electron transport layer / electron injection layer

The light emitting layer preferably does not contain a phosphorescent metal complex.
Further, the light emitting layer preferably does not contain a heavy metal complex. Examples of the heavy metal complex include an iridium complex, an osmium complex, a platinum complex and the like.
Further, it is preferable that the light emitting layer does not contain a phosphorescent rare earth metal complex.
Further, the light emitting layer may contain a metal complex, but preferably does not contain it.

FIG. 1 shows a schematic configuration of an example of an organic EL device in this embodiment.
The organic EL element 1 includes a translucent substrate 2, an anode 3, a cathode 4, and an organic layer 10 arranged between the anode 3 and the cathode 4. The organic layer 10 is configured by laminating the hole injection layer 6, the hole transport layer 7, the light emitting layer 5, the electron transport layer 8, and the electron injection layer 9 in this order from the anode 3 side.

The organic EL element of the present embodiment has an anode, a cathode, and a light emitting layer included between the anode and the cathode. The light emitting layer contains a first compound represented by the following general formula (1), a second compound, and a delayed fluorescent third compound. The first compound, the second compound and the third compound have different structures from each other. The single-term energy S ₁ (M1) of the first compound and the single-term energy S ₁ (M3) of the third compound satisfy the relationship of the following formula (Equation 1), and the single-term energy S ₁ of the second compound (M1). M2) and the ternary energy S ₁ (M3) of the third compound satisfy the relationship of the following formula (Equation 2).
S ₁ (M1)> S ₁ (M3) ... (Equation 1)
S ₁ (M2)> S ₁ (M3) ... (number 2)

The magnitude relationship between the singlet energy S ₁ (M1) of the first compound and the singlet energy S ₁ (M2) of the second compound does not matter.
In one embodiment, the singlet energy S ₁ (M1) of the first compound is greater than the singlet energy S ₁ (M2) of the second compound.
In one embodiment, the singlet energy S ₁ (M1) of the first compound is smaller than the singlet energy S ₁ (M2) of the second compound.
In one embodiment, the singlet energy S ₁ (M1) of the first compound and the singlet energy S ₁ (M2) of the second compound are equal.

When the organic EL element of the present embodiment is made to emit light, it is preferable that the first compound and the second compound do not mainly emit light in the light emitting layer. When the organic EL element of the present embodiment is made to emit light, it is preferable that the third compound mainly emits light in the light emitting layer.

The first compound and the second compound are preferably host materials.
In the present specification, in order to distinguish the first compound and the second compound from the third compound, for convenience, the first compound and the second compound when they are host materials are referred to as "matrix", respectively. Sometimes referred to.
The case where the first compound and the second compound are mixed may be referred to as "co-matrix".
A host material having a hole injecting property may be referred to as a “p host”, and a host material having an electron injecting property may be referred to as an “n host”.
Further, in the following description, when the first compound and the second compound when they are host materials are not particularly distinguished, they are collectively referred to as "host material".

In the present embodiment, one of the first compound and the second compound is a matrix having a relatively high hole injectability (that is, a p-host), and the other of the first compound and the second compound has a relative electron injectability. It is preferable to have a relatively high matrix (that is, n hosts).

The present inventors have organically contained the first compound represented by the general formula (1) and the second compound as a "co-matrix" in the light emitting layer together with the delayed fluorescent tertiary compound. It has been found that the life of the EL element can be improved.
Patent Document 1 describes delayed fluorescence of a hole-injecting carbazole compound (mCBP: p-host) and an electron-injecting triazine compound (compound T2T: n-host) as a "co-matrix" in the light emitting layer. It has been shown that when included together with a sex compound, the life of the organic EL element is improved as compared with the case where the light emitting layer contains only one kind of carbazole compound (mCBP) as a host material.
As a result of diligent studies, the present inventors have found that the use of the triphenylene compound as a "co-matrix" further improves the life.
Delayed fluorescent compounds utilize the inverted intersystem crossing from triplet excitons to singlet excitons, so they exist as unstable excitons for a long time and are thought to accelerate the deterioration of surrounding material molecules. .. Triphenylene does not have a fragile carbon-heteroatom bond and has a rigid structure with a condensed ring structure, so it does not easily deteriorate. When a triphenylene compound is used as a "co-matrix", the life of the device is extended. Conceivable. For example, triphenylene functions as a hole injection site, and the device life is improved by replacing carbazole, which is a hole injection site having a fragile carbon-nitrogen atom bond, with triphenylene. Further, the device life was also improved by substituting triphenylene for a structure composed of a combination of monocyclic aryl groups such as biphenyl.
The compound having both a triphenylene and a carbonyl group described in Patent Document 2 had a short life. It is presumed that this is because the n-orbital electron pair of the carbonyl group causes the compound having both triphenylene and the carbonyl group to form an aggregate that easily deteriorates with other materials.

Therefore, the organic EL element of the present embodiment has a longer element life than the conventional organic EL element. Further, according to the present embodiment, it is expected that the performance of the organic EL element will be improved. High performance means, for example, improvement in at least one of element life, luminous efficiency, drive voltage, and brightness. According to this embodiment, it is expected that at least one of luminous efficiency, drive voltage, and brightness is improved in addition to the device life.

Hereinafter, an embodiment in which the light emitting layer contains the first compound, the second compound, and the third compound in the first embodiment will be described.

(First compound)
The first compound is represented by the following general formula (1).

(In the general formula (1),
R ₁₀₀ to R ₁₀₈ are independently hydrogen atoms, substituents, or pairs of R _100s , pairs of R ₁₀₀ and R ₁₀₁ , pairs of R ₁₀₁ and R ₁₀₂ , R ₁₀₂ and A set of R ₁₀₃ , a set of R ₁₀₃ and R ₁₀₄ , a set of R ₁₀₄ and R ₁₀₅ , a set of R ₁₀₅ and R ₁₀₆ , a set of R ₁₀₆ and R ₁₀₇ , a set of R ₁₀₇ and R ₁₀₈ , and a set of R ₁₀₈ and R. Any one or more pairs of ₁₀₀ pairs combine with each other to form a ring.
L ₁ is a single bond or linking group
L ₁ as a linking group is
A substituted or unsubstituted ring-forming arylene group having 6 to 25 carbon atoms,
A divalent heterocyclic group having 5 to 22 substituted or unsubstituted ring-forming atoms,
Two groups selected from the group consisting of an arylene group having 6 to 25 substituted or unsubstituted ring-forming carbon atoms and a divalent heterocyclic group having 5 to 22 substituted or unsubstituted ring-forming atoms are bonded to each other. Select from the group consisting of a divalent group to be formed, an arylene group having 6 to 25 substituted or unsubstituted ring-forming carbon atoms, and a divalent heterocyclic group having 5 to 22 substituted or unsubstituted ring-forming atoms. It is a divalent group formed by combining the three groups to be formed, and B ₁ is a hydrogen atom or a substituent.
R ₁₀₀ to R ₁₀₈ and B ₁ as substituents are independent of each other.
Halogen atom,
Cyano group,
Substituentally substituted or unsubstituted aryl groups having 6 to 50 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 50 atom-forming atoms,
Substituentally substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 30 carbon atoms,
Substituentally or unsubstituted alkynyl groups having 2 to 30 carbon atoms,
Substituentally substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
Substituentally substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms,
Substituentally substituted or unsubstituted arylphosphoryl groups having 6 to 60 carbon atoms,
Hydroxy group,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms,
-A group represented by N (R ₉₁₁ ) (R ₉₁₂ ),
Thiol group,
Substituentally substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted ring-forming aralkyl groups having 7 to 30 carbon atoms,
Substitute germanium group,
Substituted phosphine oxide group,
Nitro group,
A substituted boryl group or a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms.
p is 3, and the three _R100s are the same as or different from each other.
R ₉₁₁ and R ₉₁₂ are independent of each other.
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms.
However, the first compound represented by the general formula (1) does not have a carbonyl group in the molecule. )

When L ₁ of the first compound is a single bond, B ₁ is directly attached to the triphenylene ring shown in the general formula.

In the organic EL element according to the present embodiment, a set consisting of R _100s , a set of R ₁₀₀ and R ₁₀₁ , a set of R ₁₀₁ and R ₁₀₂ , a set of R ₁₀₂ and R ₁₀₃ , a set of R ₁₀₃ and R ₁₀₄ , and R. It is preferred that none of the ₁₀₄ and R ₁₀₅ pairs, the R ₁₀₅ and R ₁₀₆ pairs, the R ₁₀₆ and R ₁₀₇ pairs, the R ₁₀₇ and R ₁₀₈ pairs, and the R ₁₀₈ and R ₁₀₀ pairs bind to each other.

In the organic EL device according to the present embodiment, the first compound is preferably represented by the following general formula (10).

(In the general formula (10),
R ₁₀₁ to R ₁₀₈ are independently synonymous with R ₁₀₁ to R ₁₀₈ in the general formula (1).
R ₁₀₉ to R ₁₁₁ are independently synonymous with R ₁₀₀ in the general formula (1).
L ₁ has the same meaning as L ₁ in the general formula (1).
B ₁ is synonymous with B ₁ in the general formula (1). )

In the organic EL device according to the present embodiment, the first compound preferably contains at least one structure represented by the following general formula (11) in the molecule.

(In the general formula (11),
Z ₁₁ to Z ₁₅ are carbon atoms that independently bond with a nitrogen atom or another atom in the molecule of the first compound. )

In the organic EL device according to the present embodiment, it is preferable that one or two of Z ₁₁ to Z ₁₅ are nitrogen atoms.

In the organic EL device according to the present embodiment, the structure represented by the general formula (11) is preferably the structure represented by the following general formula (12).

(In the general formula (12),
Z ₁₁ , Z ₁₃ and Z ₁₅ are carbon atoms that independently bond with other atoms in the molecule of the first compound. )

In the organic EL element according to the present embodiment, R ₁₀₀ to R ₁₀₈ are independently set.
Hydrogen atom,
Cyano group,
Substituentally substituted or unsubstituted aryl groups having 6 to 50 carbon atoms,
A substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms is preferable.

In the organic EL element according to the present embodiment, it is preferable that R ₁₀₀ to R ₁₀₈ are independently hydrogen atoms or substituted or unsubstituted aryl groups having 6 to 50 ring-forming carbon atoms.

In the organic EL device according to the present embodiment, R ₁₀₀ to R ₁₀₈ are preferably hydrogen atoms.

In the organic EL device according to the present embodiment, it is also preferable that R ₁₀₀ to R ₁₀₈ as substituents are independently selected from the group consisting of the following substituent group A.

When R ₁₀₀ to R ₁₀₈ as a substituent further have a substituent R _EX1 , the substituent R _EX1 (substituent in the case of "substituent or unsubstituted" in R ₁₀₀ to R ₁₀₈ as a substituent) is It is preferable that each group is independently selected from the group consisting of the following substituent group A, and more preferably a group selected from the group consisting of the following substituent group B. When the first compound has a plurality of substituents R _EX1 , the plurality of substituents R _EX1 are the same as or different from each other.

When R ₁₀₀ to R ₁₀₈ as a substituent further have a substituent R _EX1 and the substituent R _EX1 further has a substituent R _EX2 , the substituent R _EX2 (substituent or unsubstituted) in the substituent R _EX1 It is preferable that the substituents) are independently selected from the group consisting of the following substituent group B. When the first compound has a plurality of substituents R _EX2 , the plurality of substituents R _EX2 are the same as or different from each other.

(Substituent group A)
-Aryl group having 6 to 30 substituted or unsubstituted ring-forming carbon atoms-Of the substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms, one or more of the carbons of the benzene ring were replaced with nitrogen. A heterocyclic group that does not contain a partial structure, an substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted ring-forming group having 3 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms Alkyl halide group, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, substituted. Alternatively, an unsubstituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms, a substituted or unsubstituted arylphosphoryl group having 6 to 60 carbon atoms, a hydroxy group, or an substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms. Substitutable or unsubstituted ring formation A group represented by aryloxy-N (R _Z1 ) (R _Z2 ) having 6 to 30 carbon atoms (R _Z1 and R _Z2 are independently substituted or unsubstituted ring formation, respectively). Aryl groups with 6 to 30 carbon atoms, substituted or unsubstituted ring-forming atomic groups with 5 to 30 atoms, substituted or unsubstituted alkyl groups with 1 to 30 carbon atoms or substituted or unsubstituted ring-forming carbon atoms 3 ~ 30 cycloalkyl groups.)
・ Thiol group ・ Alkylthio group with 1 to 30 substituted or unsubstituted carbon number ・ Aralkyl group with 7 to 30 substituted or unsubstituted ring-forming carbon number ・ Substituted germanium group ・ Substituted or unsubstituted ring-forming carbon number 6 to 30 Arylthio group

(Substituent group B)
-Unsubstituted ring-forming aryl group having 6 to 30 carbon atoms-Contains a partial structure in which one or more carbons of the benzene ring are replaced with nitrogen among the unsubstituted ring-forming atomic number 5 to 30 heterocyclic groups. No heterocyclic group-unsubstituted alkyl group with 1 to 30 carbon atoms-unsubstituted cycloalkyl group with 3 to 30 carbon atoms-unsubstituted alkyl halide group with 1 to 30 carbon atoms-unsubstituted carbon An alkenyl group having a number of 2 to 30, an unsubstituted alkynyl group having 2 to 30 carbon atoms, an unsubstituted alkylsilyl group having 3 to 30 carbon atoms, an unsubstituted ring-forming group having 6 to 60 carbon atoms, and an unsubstituted group. An arylphosphoryl group having 6 to 60 carbon atoms, a hydroxy group, an alkoxy group having 1 to 30 unsubstituted carbon atoms, and an aryloxy-N ( _RZ3 ) (R) having 6 to 30 unsubstituted ring forming carbon atoms. The groups represented by ( _Z4 ) (R _Z3 and R _Z4 ) are independently an aryl group having an unsubstituted ring-forming carbon number of 6 to 30, a heterocyclic group having an unsubstituted ring-forming atom number of 5 to 30, and an unsubstituted group. An alkyl group having 1 to 30 carbon atoms or an unsubstituted cycloalkyl group having 3 to 30 carbon atoms.)
-Tiol group-Unsubstituted alkylthio group with 1 to 30 carbon atoms-Unsubstituted aralkyl group with 7 to 30 carbon atoms-Substituted germanium group-Unsubstituted arylthio group with 6 to 30 carbon atoms

In the organic EL element according to the present embodiment, L ₁ is a single-bonded, substituted or unsubstituted arylene group having 6 to 25 carbon atoms, or a divalent group having 5 to 22 substituted or unsubstituted ring-forming atoms. It is preferably a heterocyclic group.

In the organic EL element according to the present embodiment, L ₁ is preferably a single-bonded, substituted or unsubstituted ring-forming arylene group having 6 to 25 carbon atoms.

In the organic EL device according to the present embodiment, L ₁ is preferably a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group.

In the organic EL element according to the present embodiment, when L ₁ as a linking group further has a substituent R _LX1 , the substituent R _LX1 (substituent in the case of "substituent or unsubstituted" in L ₁ ) is It is preferably a group selected from the group consisting of the substituent group A, and more preferably a group selected from the group consisting of the substituent group B. When the first compound has a plurality of substituents R _LX1 , the plurality of substituents R _LX1 are the same as or different from each other.

When L1 as _a linking group further has a substituent R _LX1 and the substituent R _LX1 further has a substituent R _LX2 , the case of the substituent R _LX2 (referred to as "substituent or unsubstituted" in the substituent R _LX1 ). The substituent) is preferably a group selected from the group consisting of the substituent group B. When the first compound has a plurality of substituents R _LX2 , the plurality of substituents R _LX2 are the same as or different from each other.

In the organic EL device according to the present embodiment, L ₁ is any divalent group selected from the group consisting of divalent groups represented by the following general formulas (L111) to (L121). It is also preferable.

(In the general formula (L111) to the general formula (L121), R ₁₃₁ to R ₁₄₀ are independently synonymous with R ₁₀₀ in the general formula (1), and * indicates a bonding position.)

When L ₁ is a divalent group represented by the general formula (L112), the compound represented by the general formula (10) is represented by the following general formula (112).

(In the general formula (112),
R ₁₀₁ to R ₁₀₈ are independently synonymous with R ₁₀₁ to R ₁₀₈ in the general formula (1).
R ₁₀₉ to R ₁₁₁ , R ₁₃₁ to R ₁₃₃ , and R ₁₃₅ are independently synonymous with R ₁₀₀ in the general formula (1).
B ₁ is synonymous with B ₁ in the general formula (1). )

When L ₁ is a divalent group represented by the general formula (L119), the compound represented by the general formula (10) is represented by the following general formula (119).

(In the general formula (119),
R ₁₀₁ to R ₁₀₈ are independently synonymous with R ₁₀₁ to R ₁₀₈ in the general formula (1).
R ₁₀₉ to R ₁₁₁ , R ₁₃₂ to R ₁₃₅ , and R ₁₃₇ to R ₁₄₀ are independently synonymous with R ₁₀₀ in the general formula (1).
B ₁ is synonymous with B ₁ in the general formula (1). )

In the organic EL device according to the present embodiment, B ₁ is preferably a substituent.

In the organic EL device according to the present embodiment, it is preferable that B ₁ is a substituent and L ₁ is a linking group.

In the organic EL element according to the present embodiment, when B ₁ as a substituent further has a substituent R _{BX 1} , the substituent R _{BX 1} (substituent in the case of "substituent or unsubstituted" in B ₁ ) is used. It is preferably a group selected from the group consisting of the substituent group A, and more preferably a group selected from the group consisting of the substituent group B. When the first compound has a plurality of substituents _RBX1 , the plurality of substituents _RBX1 are the same as or different from each other.

When B ₁ as a substituent further has a substituent R _{BX 1} and the substituent R _BX 1 further has a substituent R _BX 2, the said substituent R _{BX 2} (in the case of "substituent or unsubstituted" in the substituent R _{BX 1} ). The substituent) is preferably a group selected from the group consisting of the substituent group B. When the first compound has a plurality of substituents _RBX2 , the plurality of substituents _RBX2 are the same as or different from each other.

In the organic EL element according to the present embodiment, B ₁ is independently a cyano group, an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, and 5 to 50 substituted or unsubstituted ring-forming atoms. It is also preferable that it is a heterocyclic group or an substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In the organic EL device according to the present embodiment, B ₁ is preferably any group selected from the group consisting of a cyano group or a group represented by the following general formulas (b1) to (b17).

(In the general formulas (b1) to (b17),
Ra is a hydrogen atom, a substituent, or one or more pairs of a plurality of adjacent Ra pairs in each general formula are bonded to each other to form a ring.
Multiple Ras are the same as or different from each other,
Rb ₁ is a hydrogen atom or a substituent and is
Rb ₂ and Rb ₃ are independently hydrogen atoms, substituents, or pairs of Rb ₂ and Rb ₃ bonded to each other to form a ring.
Rb ₄ is a hydrogen atom or a substituent and is
Ra, Rb ₁ , Rb ₂ , Rb ₃ and Rb ₄ as substituents are independently, respectively.
Halogen atom,
Cyano group,
Substituentally substituted or unsubstituted aryl groups having 6 to 50 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 50 atom-forming atoms,
Substituentally substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 30 carbon atoms,
Substituentally or unsubstituted alkynyl groups having 2 to 30 carbon atoms,
Substituentally substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
Substituentally substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms,
Substituentally substituted or unsubstituted arylphosphoryl groups having 6 to 60 carbon atoms,
Hydroxy group,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms,
-A group represented by N (R ₉₁₃ ) (R ₉₁₄ ),
Thiol group,
Substituentally substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted ring-forming aralkyl groups having 7 to 30 carbon atoms,
Substitute germanium group,
Substituted phosphine oxide group,
Nitro group,
A substituted boryl group or a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms.
R ₉₁₃ and R ₉₁₄ are independent of each other.
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms.
* Indicates the bonding position with _L1 . )

In the organic EL element according to the present embodiment, Rb ₁ , Rb ₂ , Rb ₃ and Rb ₄ are independently, respectively.
Hydrogen atom,
Substituentally substituted or unsubstituted aryl groups having 6 to 50 carbon atoms,
A substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms is preferable.

In the organic EL device according to the present embodiment, B ₁ is selected from a group consisting of a cyano group or a group represented by the following general formulas (b1) to (b11) and (b31) to (b36). It is also preferable that it is the basis of.

(In the general formulas (b1) to (b11),
Ra and Rb ₁ are independently hydrogen atoms or subgroups, respectively.
Multiple Ras are the same as or different from each other,
* Indicates the bonding position with _L1 . )

(In the above general formula (b31), one of Y ₁₁ to Y ₂₀ is a carbon atom bonded to L ₁ .
In the general formula (b32), one of Y ₂₁ to Y ₃₀ is a carbon atom bonded to L ₁ .
In the general formula (b33), one of Y ₃₁ to Y ₄₀ is a carbon atom bonded to L ₁ .
In the general formula (b34), one of Y ₄₁ to Y ₅₀ is a carbon atom bonded to L ₁ .
In the general formula (b35), one of Y ₅₁ to Y ₆₀ is a carbon atom bonded to L ₁ .
In the general formula (b36), one of Y ₆₁ to Y ₇₀ is a carbon atom bonded to L ₁ .
In the general formula (b31), the general formula (b32), the general formula (b33), the general formula (b34), the general formula (b35) and the general formula (b36), Y ₁₁ to which is not _a carbon atom bonded to L1. Y ₂₀ , Y ₂₁ to Y ₃₀ , Y ₃₁ to Y ₄₀ , Y ₄₁ to Y ₅₀ , Y ₅₁ to Y ₆₀ , and Y ₆₁ to Y ₇₀ are carbon atoms that independently bond with a nitrogen atom or Ra, respectively. Ra is independently a hydrogen atom or a substituent. )

(In the above (b1) to (b11) and (b31) to (b36), Ra and Rb1 as substituents are independently, _respectively .
Halogen atom,
Cyano group,
Substituentally substituted or unsubstituted aryl groups having 6 to 50 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 50 atom-forming atoms,
Substituentally substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 30 carbon atoms,
Substituentally or unsubstituted alkynyl groups having 2 to 30 carbon atoms,
Substituentally substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
Substituentally substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms,
Substituentally substituted or unsubstituted arylphosphoryl groups having 6 to 60 carbon atoms,
Hydroxy group,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms,
-A group represented by N (R ₉₁₃ ) (R ₉₁₄ ),
Thiol group,
Substituentally substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted ring-forming aralkyl groups having 7 to 30 carbon atoms,
Substitute germanium group,
Substituted phosphine oxide group,
Nitro group,
A substituted boryl group or a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms.
R ₉₁₃ and R ₉₁₄ are independent of each other.
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
It is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms. )

In the organic EL device according to the present embodiment, B ₁ is selected from the group consisting of a cyano group or a group represented by the general formulas (b1), (b2) and (b31) to (b36). It is also preferable that it is the basis of.

In the organic EL device according to the present embodiment, it is also preferable that B ₁ is any group selected from the group consisting of the groups represented by the general formulas (b31) to (b36).

In the organic EL element according to this embodiment, Ra is
Hydrogen atom,
Cyano group,
Substituentally substituted or unsubstituted aryl groups having 6 to 50 carbon atoms,
A substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms is preferable.

In the organic EL element according to the present embodiment, Ra is preferably a hydrogen atom or an substituted or unsubstituted aryl group having 6 to 50 carbon atoms.

In the organic EL device according to the present embodiment, Ra is preferably a hydrogen atom.

In the organic EL device according to the present embodiment, when the first compound has two or more triphenylene rings, it is preferable that the triphenylene rings are not linked by an arylene group.

In the organic EL device according to the present embodiment, it is preferable that the first compound has only one triphenylene ring in the molecule.

The first compound of the present embodiment may be a thermally activated delayed fluorescent compound or a compound that does not exhibit thermal activated delayed fluorescence. The first compound of the present embodiment is preferably a compound that does not exhibit thermally activated delayed fluorescence.

-Method for producing the first compound The first compound of the present embodiment can be produced, for example, by a known method. In addition, the first compound of the present embodiment can be produced by following a known method and using a known alternative reaction or raw material suitable for the desired product.

-Specific Examples of the First Compound Examples of specific examples of the first compound of the present embodiment include the following compounds. However, the present invention is not limited to specific examples of these compounds.

(Second compound)
The second compound is not particularly limited as long as it is a compound satisfying the relationship of the above formula (Equation 2).

-Compound represented by the general formula (2) In the organic EL device according to the present embodiment, the second compound is preferably a compound represented by the following general formula (2).

(In the general formula (2),
X ₂₁ to X ₂₆ are independently nitrogen atoms or CR ₂₀ , but at least one of X ₂₁ to X ₂₆ is a nitrogen atom.
R ₂₀ is a hydrogen atom, a substituent, a group represented by the general formula (2A), or one or more pairs of a plurality of adjacent R _20s are one or more pairs of each other. Combine to form a ring,
R ₂₁ is a substituent and
When a plurality of R _21s are present, the plurality of R _21s are the same as or different from each other.
* Is the bond position of the 6-membered ring with the carbon atom in the general formula (2).
L ₂₁ is
Single bond,
Substituentally substituted or unsubstituted ring-forming arylene group having 6 to 22 carbon atoms, a trivalent group derived from the arylene group, a tetravalent group, a pentavalent group or a hexavalent group,
Substituentally substituted or unsubstituted ring-forming divalent heterocyclic group having 5 to 22 atoms, trivalent group, tetravalent group, pentavalent group or hexavalent group derived from the heterocyclic group, or Two groups selected from the group consisting of an arylene group having 6 to 22 substituted or unsubstituted ring-forming carbon atoms and a divalent heterocyclic group having 5 to 22 substituted or unsubstituted ring-forming atoms are bonded to each other. A divalent group formed, a trivalent group derived from the divalent group, a tetravalent group, a pentavalent group or a hexavalent group.
L ₂₂ is
Single bond,
A substituted or unsubstituted ring-forming arylene group having 6 to 22 carbon atoms,
A substituted or unsubstituted ring-forming divalent heterocyclic group having 5 to 22 atoms.
n2 is 1, 2, 3, 4 or 5
When L ₂₁ is a single bond, n2 is 1, and L ₂₂ is bonded to the carbon atom of the 6-membered ring in the general formula (2).
When there are a plurality of L _22s , the plurality of L _22s are the same or different from each other.
R ₂₀ and R ₂₁ as substituents are independent of each other.
Halogen atom,
Cyano group,
Substituentally substituted or unsubstituted aryl groups having 6 to 50 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 50 atom-forming atoms,
Substituentally substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 30 carbon atoms,
Substituentally or unsubstituted alkynyl groups having 2 to 30 carbon atoms,
Substituentally substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
Substituentally substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms,
Substituentally substituted or unsubstituted arylphosphoryl groups having 6 to 60 carbon atoms,
Hydroxy group,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms,
-A group represented by N (R ₉₂₁ ) (R ₉₂₂ ),
Thiol group,
Substituentally substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted ring-forming aralkyl groups having 7 to 30 carbon atoms,
Substitute germanium group,
Substituted phosphine oxide group,
Nitro group,
A substituted boryl group or a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms.
R ₉₂₁ and R ₉₂₂ are independent of each other.
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
It is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms. )

(In the general formula (2) and the general formula (2A), the substituents in the case of "substituted or not substituted" in L ₂₁ , L ₂₂ , R ₂₀ and R ₂₁ are independent of each other.
Halogen atom,
Cyano group,
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
Substituentally substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 30 carbon atoms,
Substituentally or unsubstituted alkynyl groups having 2 to 30 carbon atoms,
Substituentally substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
Substituentally substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms,
Substituentally substituted or unsubstituted arylphosphoryl groups having 6 to 60 carbon atoms,
Hydroxy group,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms,
-A group represented by N (R ₈₂₁ ) (R ₈₂₂ ),
Thiol group,
Substituentally substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted ring-forming aralkyl groups having 7 to 30 carbon atoms,
Substitute germanium group,
Substituted phosphine oxide group,
Nitro group,
A substituted boryl group or a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms.
R ₈₂₁ and R ₈₂₂ are independent of each other.
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
It is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms. )

The "trivalent group derived from an arylene group" is a group obtained by removing one hydrogen atom from the arylene group.
The "tetravalent group derived from the arylene group" is a group obtained by removing two hydrogen atoms from the arylene group.
The "pentovalent group derived from the arylene group" is a group obtained by removing three hydrogen atoms from the arylene group.
The "hexavalent group derived from an arylene group" is a group obtained by removing four hydrogen atoms from the arylene group.

The "trivalent group derived from a divalent heterocyclic group" is a group obtained by removing one hydrogen atom from a divalent heterocyclic group.
The "tetravalent group derived from a divalent heterocyclic group" is a group obtained by removing one hydrogen atom from a trivalent heterocyclic group.
The "pentovalent group derived from a divalent heterocyclic group" is a group obtained by removing one hydrogen atom from a tetravalent heterocyclic group.
The "hexavalent group derived from a divalent heterocyclic group" is a group obtained by removing one hydrogen atom from a pentavalent heterocyclic group.

The mode of binding of the group represented by the general formula (2A) is determined according to the value of n2.
When n2 is 1, the general formula (2A) is represented by the following general formula (2A-1). When n2 is 1, L ₂₁ is, for example, an "allylen group".
When n2 is 2, the general formula (2A) is represented by the following general formula (2A-2). When n2 is 2, L ₂₁ is, for example, a "trivalent group derived from an arylene group".
When n2 is 3, the general formula (2A) is represented by the following general formula (2A-3). When n2 is 3, L ₂₁ is, for example, a "tetravalent group derived from an arylene group".
When n2 is 4, the general formula (2A) is represented by the following general formula (2A-4). When n2 is 4, L ₂₁ is, for example, "a pentavalent group derived from an arylene group".
When n2 is 5, the general formula (2A) is represented by the following general formula (2A-5). When n2 is 5, L ₂₁ is, for example, a "hexavalent group derived from an arylene group".
In the following general formulas (2A-1) to (2A-5), * is a binding site of the six-membered ring with the carbon atom in the general formula (2).

In the general formula (2A), when n2 is 1 and L ₂₁ is "a divalent group formed by combining two groups L ₂₁₁ and L ₂₁₂ ", the general formula (2A) is expressed. For example, it is represented by the following general formula (2A-6).

In the general formula (2A), when n2 is 2 and L ₂₁ is a trivalent group derived from "a divalent group formed by combining two groups of L ₂₁₁ and L ₂₁₂ ". , The general formula (2A) is represented by, for example, the following general formula (2A-7).

In the general formula (2A), when n2 is 3 and L ₂₁ is a tetravalent group derived from "a divalent group formed by combining two groups of L ₂₁₁ and L ₂₁₂ ". , The general formula (2A) is represented by, for example, the following general formula (2A-8).

In the general formula (2A), when n2 is 4 and L ₂₁ is a pentavalent group derived from "a divalent group formed by combining two groups of L ₂₁₁ and L ₂₁₂ ". , The general formula (2A) is represented by, for example, the following general formula (2A-9).

In the general formula (2A), when n2 is 5, and L ₂₁ is a hexavalent group derived from "a divalent group formed by combining two groups of L ₂₁₁ and L ₂₁₂ ". , The general formula (2A) is represented by, for example, the following general formula (2A-10).

(In the general formulas (2A-6) to (2A-10),
L ₂₁₁ is
It is an arylene group having 6 to 22 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 22 substituted or unsubstituted ring-forming atoms.
L ₂₁₂ is
A substituted or unsubstituted ring-forming arylene group having 6 to 22 carbon atoms,
Substituted or unsubstituted ring-forming trivalent group derived from an arylene group having 6 to 22 carbon atoms, a tetravalent group, a pentavalent group or a hexavalent group,
A divalent heterocyclic group having 5 to 22 substituted or unsubstituted ring-forming atoms, or a trivalent group derived from a divalent heterocyclic group having 5 to 22 substituted or unsubstituted ring-forming atoms. It is a 4-valent group, a 5-valent group, or a 6-valent group.
* Is the binding site of the six-membered ring with the carbon atom in the general formula (2). )

In the organic EL device according to the present embodiment, the second compound is preferably a compound represented by the following general formula (21) or general formula (22).

(In the general formula (21) and the general formula (22), R ₂₀₁ to R ₂₀₇ are independently synonymous with R ₂₀ in the general formula (2).)

In the second compound, it is preferable that the pair consisting of a plurality of adjacent _R20s does not bind to each other (does not form a ring).
It is preferable that the pair consisting of two or more adjacent R ₂₀₅ to R ₂₀₇ does not bond to each other (does not form a ring).

In the organic EL device according to the present embodiment, the second compound is preferably the compound represented by the general formula (21).

In the organic EL element according to the present embodiment, R20 is a hydrogen atom, a cyano group, an aryl group having 6 to ₅₀ substituted or unsubstituted ring-forming carbon atoms, and a complex having 5 to 50 substituted or unsubstituted ring-forming atoms. It is preferably a ring group or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In the organic EL element according to the present embodiment, R20 is preferably a hydrogen atom or an substituted or unsubstituted aryl group having ₆ to 50 carbon atoms.

_{In the organic EL device according to the present embodiment, R20} is preferably a hydrogen atom.

In the second compound of the present embodiment, it is also preferable that at least one _R20 is a group represented by the general formula (2A).
In the second compound of the present embodiment, it is also preferable that at least one of R ₂₀₁ to R ₂₀₃ is a group represented by the general formula (2A).
In the second compound of the present embodiment, it is also preferable that at least one of R ₂₀₄ to R ₂₀₇ is a group represented by the general formula (2A).

In the second compound of the present embodiment, at least one R ₂₀ is a group represented by the general formula (2A), and in the general formula (2A), R ₂₁ is a substituted or unsubstituted ring-forming carbon number. It is preferably a condensed aryl group of 10 to 50, or a substituted or unsubstituted condensed heterocyclic group having 9 to 50 ring-forming atoms.
In the second compound of the present embodiment, in the general formula (2A), R ₂₁ is a substituted or unsubstituted ring-forming aryl group having 10 to 50 carbon atoms, or a substituted or unsubstituted ring-forming atom number 13. More preferably, it is a condensed heterocyclic group of about 50.
The “condensed aryl group having 10 to 50 ring-forming carbon atoms” is a group having a partial structure in which two rings share one side among the aryl groups having 10 to 50 ring-forming carbon atoms. The fused aryl group may have a plurality of partial structures in which two rings share one side.
The “condensed heterocyclic group having 9 to 50 ring-forming atoms” is a group having a partial structure in which two rings share one side among the heterocyclic groups having 9 to 50 ring-forming atoms. The condensed heterocyclic group may have a plurality of partial structures in which two rings share one side.

In the second compound of the present embodiment, R ₂₁ is preferably any of the groups represented by the following general formulas (c1) to (c9).

(In the above general formulas (c1) to (c9), Rc is a hydrogen atom, a substituent, or one or more pairs of adjacent Rc pairs are bonded to each other to form a ring. However, a plurality of Rc are the same as or different from each other, and Rc ₁ and Rc ₂ are independently hydrogen atoms or substituents, or a pair consisting of Rc ₁ and Rc ₂ is bonded to each other. Rc ₃ is a hydrogen atom or a substituent, and Rc, Rc ₁ , Rc ₂ and Rc ₃ as substituents are independently in R ₂₁ in the above general formula (2A). It is synonymous with a substituent in the case of "substituent or non-substituent".)

In the general formulas (c1) to (c9), Rc is a hydrogen atom, a substituted or unsubstituted ring-forming aryl group having 6 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. It is preferable, and it is more preferable that it is a hydrogen atom.
In the general formulas (c3) to (c4), Rc ₁ and Rc ₂ are independently substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, or substituted or unsubstituted aryl groups having 1 to 30 carbon atoms, respectively. It is preferable that the alkyl group of the above or a pair consisting of Rc ₁ and Rc ₂ is bonded to each other to form a ring.
In the general formula (c5), Rc ₃ is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted ring formation. It is preferably a heterocyclic group having 5 to 30 atoms.

In the second compound of the present embodiment, R ₂₁ is preferably any of the groups represented by the general formulas (c1) to (c6).

_In the second compound of this embodiment, L21 is a single-bonded or substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl. From the group consisting of a group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, and a substituted or unsubstituted carbazolyl group. It is preferably a divalent, trivalent, tetravalent, pentavalent or hexavalent group derived from any of the selected groups.

In the second compound of the present embodiment, L ₂₁ is a single bond or an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, and an unsubstituted terphenyl group. , Bivalent, trivalent, 4 It is more preferably a valence, pentavalent or hexavalent group.

In the second compound of the present embodiment, L ₂₂ is a single bond or a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted phenanthryl. From the group consisting of a group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothienyl group, and a substituted or unsubstituted carbazolyl group. It is preferably a divalent group derived from any of the selected groups.

In the second compound of the present embodiment, L ₂₂ is a single bond or an unsubstituted phenyl group, an unsubstituted biphenyl group, an unsubstituted naphthyl group, an unsubstituted phenanthryl group, an unsubstituted terphenyl group. , A divalent group derived from any group selected from the group consisting of an unsubstituted fluorenyl group, an unsubstituted dibenzofuranyl group, an unsubstituted dibenzothienyl group, and an unsubstituted carbazolyl group. Is more preferable.

-Compound represented by the general formula (20) In the organic EL device according to the present embodiment, the second compound is preferably a compound represented by the following general formula (20).

(In the general formula (20), Cz is a group represented by the following general formula (201).
M ₂₀ is
Single bond,
A substituted or unsubstituted ring-forming arylene group having 6 to 25 carbon atoms,
A divalent heterocyclic group having 5 to 22 substituted or unsubstituted ring-forming atoms,
Two groups selected from the group consisting of an arylene group having 6 to 25 substituted or unsubstituted ring-forming carbon atoms and a divalent heterocyclic group having 5 to 22 substituted or unsubstituted ring-forming atoms are bonded to each other. Select from the group consisting of a divalent group to be formed, an arylene group having 6 to 25 substituted or unsubstituted ring-forming carbon atoms, and a divalent heterocyclic group having 5 to 22 substituted or unsubstituted ring-forming atoms. It is a divalent group formed by combining the three groups to be formed.
D ₂₀ is the substituent E1 and
Substituent E1 is unsubstituted or has one or more substituents E2.
Substituent E2 is unsubstituted or has one or more substituents E3.
Substituent E3 is unsubstituted or has one or more substituents E4.
Substituents E1, substituents E2, and substituents E3 are independent of each other.
Halogen atom,
Cyano group,
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
Substituentally substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 30 carbon atoms,
Substituentally or unsubstituted alkynyl groups having 2 to 30 carbon atoms,
Substituentally substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
Substituentally substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms,
Substituentally substituted or unsubstituted arylphosphoryl groups having 6 to 60 carbon atoms,
Hydroxy group,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms,
-A group represented by N (R ₉₂₃ ) (R ₉₂₄ ),
Thiol group,
Substituentally substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted ring-forming aralkyl groups having 7 to 30 carbon atoms,
Substitute germanium group,
Substituted phosphine oxide group,
Nitro group,
A substituted boryl group or a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms.
Substituents E4 are independent of each other.
Halogen atom,
Cyano group,
An unsubstituted aryl group having 6 to 30 carbon atoms,
Heterocyclic group with 5 to 30 atoms forming an unsubstituted ring,
An unsubstituted alkyl group having 1 to 30 carbon atoms,
An unsubstituted cycloalkyl group having 3 to 30 carbon atoms,
An unsubstituted alkyl halide group having 1 to 30 carbon atoms,
An unsubstituted alkenyl group having 2 to 30 carbon atoms,
An unsubstituted alkynyl group having 2 to 30 carbon atoms,
An unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
An unsubstituted arylsilyl group having 6 to 60 carbon atoms,
An unsubstituted arylphosphoryl group having 6 to 60 carbon atoms,
Hydroxy group,
An unsubstituted alkoxy group having 1 to 30 carbon atoms,
An unsubstituted, ring-forming aryloxy group having 6 to 30 carbon atoms,
-A group represented by N (R ₉₂₅ ) (R ₉₂₆ ),
Thiol group,
An unsubstituted alkylthio group having 1 to 30 carbon atoms,
An unsubstituted ring-forming aralkyl group having 7 to 30 carbon atoms,
Substitute germanium group,
Substituted phosphine oxide group,
Nitro group,
A substituted boryl group or an unsubstituted arylthio group having 6 to 30 carbon atoms.
R ₉₂₃ and R ₉₂₄ are independent of each other.
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms.
R ₉₂₅ and R ₉₂₆ are independent of each other.
An unsubstituted aryl group having 6 to 30 carbon atoms,
Heterocyclic group with 5 to 30 atoms forming an unsubstituted ring,
An unsubstituted alkyl group having 1 to 30 carbon atoms or an unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms.
When a plurality of substituents E1 are present, the plurality of substituents E1 are the same as or different from each other.
When a plurality of substituents E2 are present, the plurality of substituents E2 are the same as or different from each other.
When a plurality of substituents E3 are present, the plurality of substituents E3 are the same as or different from each other.
When a plurality of substituents E4 are present, the plurality of substituents E4 are the same as or different from each other. )

(In the general formula (201),
Each of R _1C to R _9C is independently a hydrogen atom, a substituent, or a single bond bonded to M, or a set of R _1C and R _2C , a set of R _2C and R _3C . , R _3C and R _4C pairs, R _5C and R _6C pairs, R _6C and R _7C pairs, and one or more pairs of R _7C and R _8C combined with each other to form a ring Cx. death,
However, one of R _1C to R _9C is a single bond bonded to M ₂₀ , or any one of the carbon atoms constituting the ring Cx is bonded to M ₂₀ .
R _1C to R _9C as substituents are independent of each other.
Halogen atom,
Cyano group,
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
Substituentally substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 30 carbon atoms,
Substituentally or unsubstituted alkynyl groups having 2 to 30 carbon atoms,
Substituentally substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
Substituentally substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms,
Substituentally substituted or unsubstituted arylphosphoryl groups having 6 to 60 carbon atoms,
Hydroxy group,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms,
-A group represented by N (R ₉₂₇ ) (R ₉₂₈ ),
Thiol group,
Substituentally substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted ring-forming aralkyl groups having 7 to 30 carbon atoms,
Substitute germanium group,
Substituted phosphine oxide group,
Nitro group,
A substituted boryl group or a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms.
R ₉₂₇ and R ₉₂₈ are independent of each other.
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
It is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms. )

In the general formula (20), when M ₂₀ is a single bond, Cz and D ₂₀ are directly bonded. Specifically, when M ₂₀ is a single bond, D ₂₀ is directly bonded to one of the carbon atoms constituting R _1C to R _9C and ring Cx in the general formula (201).

It is preferable that R _1C to R _9C as the substituents are groups independently selected from the substituent group A, respectively.
When R _1C to R _9C as a substituent further have a substituent, the substituent (substituent in the case of "substituent or unsubstituted" in R _1C to R _9C ) is selected from the substituent group A. The group is preferably a group, and more preferably a group selected from the substituent group B.

The ring Cx is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 30 carbon atoms, or a carbon of the benzene ring among the substituted or unsubstituted heterocyclic rings having 5 to 30 ring-forming atoms. It is preferable that one or more of the above is a heterocycle containing no partial structure replaced with nitrogen.
It is particularly preferable that the ring Cx is a heterocyclic ring having a substituted or unsubstituted ring-forming atom number of 5 to 30 and which does not contain a partial structure in which one or more carbons of the benzene ring are replaced with nitrogen.
When the ring Cx further has a substituent, the substituent (the substituent in the case of "substituent or unsubstituted" in the ring Cx) is preferably a group selected from the substituent group A, and the substitution thereof. It is more preferable that the group is selected from the group B.

-"D ₂₀ " in the general formula (20)
The substituent E1 is preferably a group independently selected from the substituent group A, and more preferably a group selected from the substituent group B.
Further, the substituent E1 is preferably a group independently selected from the following substituent group C, and more preferably a group selected from the following substituent group D.
The substituent (substituent (substituent E2) in the case of "substituent or unsubstituted" in the substituent E1) when the substituent E1 further has a substituent is independently selected from the substituent group A. It is preferably a group to be used, and more preferably a group selected from the substituent group B.
The substituent (substituent (substituent E3) in the case of "substituent or unsubstituted" in the substituent E2) when the substituent E2 further has a substituent is independently selected from the substituent group A. It is preferably a group to be used, and more preferably a group selected from the substituent group B.
The substituent (substituent (substituent E4) in the case of "substituent or unsubstituted" in the substituent E3) when the substituent E3 further has a substituent is independently selected from the substituent group B. It is preferable that it is a group to be used.
The substituents of the substituent group C and the substituent group D are groups having a relatively strong electron donating property.

(Substituent group C)
-Aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms-Of the substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, one or more carbons of the benzene ring were replaced with nitrogen. Heterocyclic group containing no partial structure

(Substituent group D)
-Unsubstituted ring-forming aryl group having 6 to 50 carbon atoms-Contains a partial structure in which one or more carbons of the benzene ring are replaced with nitrogen among the unsubstituted ring-forming atomic number 5 to 50 heterocyclic groups. No heterocyclic group

-"M ₂₀ " in the general formula (20)
When M ₂₀ is a linking group, it is also preferable that _{M 20} is a group independently selected from the following substituent group EM.
When M ₂₀ further has a substituent, the substituent (substituent in the case of "substituent or unsubstituted" in M ₂₀ ) may be a group independently selected from the substituent group A. It is more preferable that the group is selected from the substituent group B.
The substituent of the substituent group _EM is a group having a relatively strong electron donating property.

(Substituent group _EM )
Substituent _EM1 : Substituent or unsubstituted ring-forming arylene group having 6 to 22 carbon atoms ・ Substituent _EM2 : Substituent or unsubstituted ring-forming divalent heterocyclic group having 5 to 22 atomic atoms, benzene Divalent heterocyclic group / substituent _EM3 containing no partial structure in which one or more of the carbons of the ring are replaced with nitrogen: Two selected from the group consisting of the substituent _EM1 and the substituent _EM2 . Divalent group / substituent _EM4 formed by bonding groups: A divalent group formed by bonding three groups selected from the group consisting of the substituent _EM1 and the substituent _EM2 .

The second compound of the present embodiment is preferably a compound represented by the following general formula (202).

(In the general formula (202), M ₂₀ and D ₂₀ are synonymous with M ₂₀ and D ₂₀ in the general formula (20), and R _1C to R _8C are independently described in the general formula (20). It is synonymous with R _1C to R _8C in 201).)

In the second compound of the present embodiment, M ₂₀ is a single-bonded, substituted or unsubstituted arylene group having 6 to 25 ring-forming carbon atoms, or a substituted or unsubstituted ring-forming atomic number of 5 to 22 divalent heterocyclic compounds. It is also preferable that it is a ring group.
In the second compound of the present embodiment, M ₂₀ is preferably a single-bonded or substituted or unsubstituted ring-forming arylene group having 6 to 25 carbon atoms.
In the second compound of the present embodiment, M ₂₀ is a single bond, an unsubstituted ring-forming carbon number 6 to 25 arylene group, or an unsubstituted ring-forming atom number 5 to 22 divalent heterocyclic group. It is also preferable.

In the second compound of the present embodiment, M ₂₀ is preferably a substituted or unsubstituted paraphenylene group, a substituted or unsubstituted parabiphenylene group, or a substituted or unsubstituted paraterphenylene group.
In the second compound of the present embodiment, M ₂₀ is preferably an unsubstituted paraphenylene group, an unsubstituted parabiphenylene group, or an unsubstituted paraterphenylene group.

In the second compound of the present embodiment, D ₂₀ is preferably any of the groups represented by the following general formulas (d1) to (d17).

(In the above general formulas (d1) to (d17), Ra is a hydrogen atom, a substituent, or one or more pairs of adjacent Ra pairs are bonded to each other to form a ring. However, multiple Ras are the same as or different from each other,
Rb ₁ and Rb ₂ are independently hydrogen atoms, substituents, or pairs of Rb ₁ and Rb ₂ bonded to each other to form a ring.
Rb ₃ is a hydrogen atom or a substituent and is
Ra, Rb ₁ , Rb ₂ and Rb ₃ as substituents are independently synonymous with substituent E1 as D ₂₀ in the general formula (20). )

In the second compound of the present embodiment, when D ₂₀ is a group represented by any of the above general formulas (d1) to (d17), Ra is a hydrogen atom, substituted or unsubstituted ring-forming carbon number. It is preferably an aryl group of 6 to 30, or an substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and more preferably a hydrogen atom.
In the second compound of the present embodiment, when D ₂₀ is a group represented by the general formula (d3) or (d4), Rb ₁ and Rb ₂ independently form a substituted or unsubstituted ring, respectively. It is preferable that the aryl group has 6 to 30 carbon atoms, or the substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or the pair consisting of Rb ₁ and Rb ₂ is bonded to each other to form a ring.
In the second compound of the present embodiment, when D ₂₀ is a group represented by the general formula (d5), Rb ₃ is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, substituted or substituted. It is preferably an unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring-forming atoms.

In the second compound of the present embodiment, when D ₂₀ is a group represented by any of the above general formulas (d1) to (d17), one or more sets of adjacent Ra sets are added to each other. It is preferable not to bind.
In the second compound of the present embodiment, when D ₂₀ is a group represented by any of the above general formulas (d1) to (d17), one or more sets of adjacent Ra sets are added to each other. It is also preferable to bind.

In the second compound of the present embodiment, Cz is preferably a group represented by any of the following general formulas (C-1) to (C-6).

(In the general formulas (C-1) to (C-6),
R ₂₀₀₁ to R ₂₀₀₆ are single bonds that are independent substituents or bind to M ₂₀ .
Z ₂₁ to Z ₂₆ are independently oxygen atoms, sulfur atoms, CR _20C R _21C or NR _22C , R _22C is a substituent, and R _20C and R _21C are independent hydrogen atoms. Whether it is a substituent _, a single bond that binds to M ₂₀ , or R _20C and R _21C bond to each other to form a ring.
Each of R ₂₁₀ to R ₂₁₉ is independently a hydrogen atom, a substituent or a single bond bonded to M ₂₀ , or a set of R ₂₁₀ and R ₂₁₁ , a set of R ₂₁₁ and R ₂₁₂ , and R ₂₁₂ . And R ₂₁₃ pairs, R ₂₁₄ and R ₂₁₅ pairs, R ₂₁₆ and R ₂₁₇ pairs, R ₂₁₇ and R ₂₁₈ pairs, and any one or more pairs of R ₂₁₈ and R ₂₁₉ coupled to each other. Form a ring,
However, one of R ₂₁₀ to R ₂₁₉ , R ₂₀₀₁ , R _20C , R _21C and R _22C is a single bond that binds to M ₂₀ .
Each of R ₂₂₀ to R ₂₂₉ is independently a hydrogen atom, a substituent or a single bond bonded to M ₂₀ , or a set of R ₂₂₀ and R ₂₂₁ , a set of R ₂₂₁ and R ₂₂₂ , and R ₂₂₂ . And R ₂₂₃ pairs, R ₂₂₄ and R ₂₂₅ pairs, R ₂₂₆ and R ₂₂₇ pairs, R ₂₂₇ and R ₂₂₈ pairs, and any one or more pairs of R ₂₂₈ and R ₂₂₉ coupled to each other. Form a ring,
However, one of R ₂₂₀ to R ₂₂₉ , R ₂₀₀₂ , R _20C , R _21C and R _22C is a single bond that binds to M ₂₀ .
Each of R ₂₃₀ to R ₂₃₉ is independently a hydrogen atom, a substituent or a single bond bonded to M ₂₀ , or a set of R ₂₃₀ and R ₂₃₁ and a set of R ₂₃₁ and R ₂₃₂ , R ₂₃₂ . And one or more of the _R233 pairs, the _R235 and _R236 pairs, the _R236 and _R237 pairs, and the _R237 and _R238 pairs join together to form a ring.
However, one of R ₂₃₀ to R ₂₃₉ , R ₂₀₀₃ , R _20C , R _21C and R _22C is a single bond that binds to M ₂₀ .
Each of R ₂₄₀ to R ₂₄₉ is independently a hydrogen atom, a substituent or a single bond bonded to M ₂₀ , or a set of R ₂₄₀ and R ₂₄₁ and a set of R ₂₄₁ and R ₂₄₂ , R ₂₄₂ . And R ₂₄₃ pairs, R ₂₄₅ and R ₂₄₆ pairs, R ₂₄₆ and R ₂₄₇ pairs, and any one or more pairs of R ₂₄₇ and R ₂₄₈ combined with each other to form a ring.
However, one of R ₂₄₀ to R ₂₄₉ , R ₂₀₀₄ , R _20C , R _21C and R _22C is a single bond that binds to M ₂₀ .
Each of R ₂₅₀ to R ₂₅₉ is independently a hydrogen atom, a substituent or a single bond bonded to M ₂₀ , or a set of R ₂₅₀ and R ₂₅₁ and a set of R ₂₅₁ and R ₂₅₂ , R ₂₅₂ . And R ₂₅₃ pairs, R ₂₅₄ and R ₂₅₅ pairs, R ₂₅₅ and R ₂₅₆ pairs, R ₂₅₆ and R ₂₅₇ pairs, and any one or more pairs of R ₂₅₈ and R ₂₅₉ combined with each other. Form a ring,
However, one of R ₂₅₀ to R ₂₅₉ , R ₂₀₀₅ , R _20C , R _21C and R _22C is a single bond that binds to M ₂₀ .
Each of _R260 to _R269 is independently a hydrogen atom, a substituent or a single bond bonded to _M20 , or a set of _R260 and _R261 , a set of _R261 and _R262 , and _R262 . And R ₂₆₃ pairs, R ₂₆₄ and R ₂₆₅ pairs, R ₂₆₅ and R ₂₆₆ pairs, R ₂₆₆ and R ₂₆₇ pairs, and any one or more pairs of R ₂₆₈ and R ₂₆₉ combined with each other. Form a ring,
However, one of R ₂₆₀ to R ₂₆₉ , R ₂₀₀₆ , R _20C , R _21C and R _22C is a single bond that binds to M ₂₀ .
R ₂₁₀ to R ₂₆₉ , R ₂₀₀₁ to R ₂₀₀₆ , R _20C , R _21C and R _22C as substituents are independently synonymous with R _1C to R _9C as substituents in the general formula (201). .. )

In the second compound of the present embodiment, R ₂₁₀ to R ₂₆₉ , R _20C and R _21C are independently hydrogen atoms, substituted or unsubstituted aryl groups having 6 to 30 ring-forming carbon atoms, substituted or unsubstituted, respectively. A heterocyclic group having 5 to 30 ring-forming atoms, or an substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
R ₂₀₀₁ to R ₂₀₀₆ and R _22C are independently substituted or unsubstituted aryl groups having 6 to 30 carbon atoms, substituted or unsubstituted heterocyclic groups having 5 to 30 ring-forming atoms, or substituted or substituted. It is preferably an unsubstituted alkyl group having 1 to 30 carbon atoms.
In the second compound of the present embodiment, R ₂₁₀ to R ₂₆₉ , R _20C and R _21C are independently hydrogen atoms, substituted or unsubstituted aryl groups having 6 to 30 ring-forming carbon atoms, substituted or unsubstituted, respectively. Of the heterocyclic groups having 5 to 30 ring-forming atoms, a heterocyclic group containing no partial structure in which one or more carbons of the benzene ring are replaced with nitrogen, or an substituted or unsubstituted alkyl having 1 to 30 carbon atoms. Is the basis and
R ₂₀₀₁ to R ₂₀₀₆ and R _22C are independently substituted or unsubstituted aryl groups having 6 to 30 carbon atoms and substituted or unsubstituted heterocyclic groups having 5 to 30 ring forming atoms, and benzene. It is preferable that one or more of the carbons of the ring are a heterocyclic group containing no partial structure in which the carbon is replaced with nitrogen, or an substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.

In the second compound of the present embodiment, in the general formulas (C- ₁ ) to ₍ C-6), Z21, _Z22 , _Z23 , Z24, _Z25 and _Z26 are independently oxygen atoms. Alternatively, it is preferably a sulfur atom.
In the second compound of the present embodiment, in the general formulas (C-1) to (C-6), Z ₂₁ , Z ₂₂ , Z ₂₃ , Z ₂₄ , Z ₂₅ and Z ₂₆ may be oxygen atoms. preferable.

The second compound of the present embodiment may be a thermally activated delayed fluorescent compound or a compound that does not exhibit thermal activated delayed fluorescence. The second compound of the present embodiment is preferably a compound that does not exhibit thermally activated delayed fluorescence.

In the organic EL element according to the present embodiment, when the first compound is a compound whose molecule does not contain the structure represented by the general formula (11), the second compound is represented by the general formula (2). It is preferable that it is a compound to be used.

In the organic EL element according to the present embodiment, when the first compound is a compound having a structure represented by the general formula (11) in the molecule, the second compound is represented by the general formula (20). It is preferably a compound.

In the organic EL device according to the present embodiment, it is preferable that either the first compound or the second compound contains an azine ring.

In the organic EL element according to the present embodiment, when the first compound does not contain an azine ring in the molecule, it is preferable that the second compound contains an azine ring in the molecule.

In the organic EL element according to the present embodiment, when the first compound contains an azine ring in the molecule, it is preferable that the second compound does not contain the azine ring in the molecule.

-Method for producing the second compound The second compound of the present embodiment can be produced, for example, by a known method. In addition, the second compound of the present embodiment can be produced by following a known method and using a known alternative reaction or raw material suitable for the desired product.

-Specific Examples of the Second Compound Examples of specific examples of the second compound of the present embodiment include the following compounds. However, the present invention is not limited to specific examples of these compounds.

(Third compound)
The third compound is a delayed fluorescent compound, and is not particularly limited as long as it is a compound satisfying the relationship between the mathematical formula (Equation 1) and the mathematical formula (Equation 2).

-Delayed fluorescence Delayed fluorescence is explained on pages 261-268 of "Device Properties of Organic Semiconductors" (edited by Chihaya 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 light-emitting material can be reduced, the reverse energy from the excited triplet state, which usually has a low transition probability, to the excited singlet state. Transfer occurs with high efficiency and Thermally Activated Delayed Fluore
It is explained that sense, TADF) is expressed. Further, FIG. 10.38 in the document describes the mechanism of delayed fluorescence generation. The third compound in the present embodiment is preferably a compound exhibiting thermally activated delayed fluorescence generated by such a mechanism.

Generally, the emission of delayed fluorescence can be confirmed by transient PL (Photoluminescence) measurement.

It is also possible to analyze the behavior of delayed fluorescence based on the decay curve obtained from the transient PL measurement. Transient PL measurement is a method of irradiating a sample with a pulse laser to excite it and measuring the attenuation behavior (transient characteristics) of PL light emission after the irradiation is stopped. PL emission in TADF materials is classified into emission components from singlet excitons generated by the first PL excitation and emission components from singlet excitons generated via triplet excitons. The lifetime of singlet excitons generated by the first PL excitation is on the order of nanoseconds and is very short. Therefore, the light emitted from the singlet exciton is rapidly attenuated after irradiation with the pulse laser.
Delayed fluorescence, on the other hand, is slowly attenuated due to light emission from singlet excitons generated via long-lived triplet excitons. As described above, there is a large time difference between the emission from the singlet excitons generated by the first PL excitation and the emission from the singlet excitons generated via the triplet excitons. Therefore, the emission intensity derived from delayed fluorescence can be obtained.

FIG. 2 shows a schematic diagram of an exemplary device for measuring transient PL.
An example of a transient PL measurement method using FIG. 2 and a behavior analysis of delayed fluorescence will be described.

The transient PL measuring device 100 of FIG. 2 includes a pulse laser unit 101 capable of irradiating light of a predetermined wavelength, a sample chamber 102 accommodating a measurement sample, a spectroscope 103 that disperses light emitted from the measurement sample, and 2 A streak camera 104 for forming a dimensional image and a personal computer 105 for capturing and analyzing a two-dimensional image are provided. The measurement of transient PL is not limited to the device shown in FIG.

The sample accommodated in the sample chamber 102 is obtained by forming a thin film on a quartz substrate in which a doping material is doped at a concentration of 12% by mass with respect to the host material.

The thin film sample housed in the sample chamber 102 is irradiated with a pulse laser from the pulse laser unit 101 to excite the doping material. Emissions are taken out in a direction of 90 degrees with respect to the irradiation direction of the excitation light, the taken out light is separated by a spectroscope 103, and a two-dimensional image is formed in the streak camera 104. As a result, it is possible to obtain a two-dimensional image 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 on a predetermined time axis, it is possible to obtain an emission spectrum in which the vertical axis is the emission intensity and the horizontal axis is the wavelength. Further, when the two-dimensional image is cut out on the wavelength axis, an attenuation curve (transient PL) in which the vertical axis is the logarithm of the emission intensity and the horizontal axis is the time can be obtained.

For example, the following reference compound H1 was used as the host material, and the following reference compound D1 was used as the doping material to prepare a thin film sample A as described above, and transient PL measurement was performed.

Here, the attenuation curves were analyzed using the above-mentioned thin film sample A and thin film sample B. As the thin film sample B, the following reference compound H2 was used as a host material, and the reference compound D1 was used as a doping material to prepare a thin film sample as described above.

FIG. 3 shows the attenuation curves obtained from the transient PL measured for the thin film sample A and the thin film sample B.

As described above, by transient PL measurement, it is possible to obtain a emission attenuation curve with the vertical axis as the emission intensity and the horizontal axis as the time. Based on this emission attenuation 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 delayed fluorescent materials, the ratio of the intensity of slowly decaying delayed fluorescence to the intensity of rapidly decaying fluorescence is somewhat large.

Specifically, as the light emission from the delayed fluorescent material, there are Prompt light emission (immediate light emission) and Delay light emission (delayed light emission). Prompt emission (immediate emission) is emission that is immediately observed from the excited state after being excited by pulsed light (light emitted from a pulse laser) having a wavelength absorbed by the delayed fluorescent material. Delay emission (delayed emission) is emission that is not immediately observed after being excited by the pulsed light, but is observed thereafter.

The amount of Prompt emission and Delay emission and their ratio can be determined by the same method as described in "Nature 492, 234-238, 2012" (Reference 1). The apparatus used for calculating the amount of Prompt emission and Delay emission is not limited to the apparatus described in Reference 1 or the apparatus shown in FIG.

Further, in the present specification, a sample prepared by the following method is used for measuring the delayed fluorescence of the third compound. For example, the tertiary compound is dissolved in toluene to prepare a dilute solution having an absorbance of 0.05 or less at the excitation wavelength in order to remove the contribution of self-absorption. Further, in order to prevent quenching by oxygen, the sample solution is frozen and degassed and then sealed in a cell with a lid under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon.
The fluorescence spectrum of the sample solution is measured with a spectrofluorometer FP-8600 (manufactured by Nippon Spectroscopy Co., Ltd.), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene is measured under the same conditions. Using the fluorescence area intensities of both spectra, Morris et al. J. Phys. Chem. The total fluorescence quantum yield is calculated by the equation (1) in 80 (1976) 969.

The amount of Prompt emission and Delay emission and their ratio can be determined by the same method as described in "Nature 492, 234-238, 2012" (Reference 1). The apparatus used for calculating the amount of Prompt emission and Delay emission is not limited to the apparatus described in Reference 1 or the apparatus shown in FIG.
In the present embodiment, when the amount of Prompt emission (immediate emission) of the compound to be measured (third compound) is XP and the amount of _Delay emission (delayed emission) is _XD , _XD / _XP The value is preferably 0.05 or more.
The measurement of the amount and ratio of Prompt emission and Delay emission of a compound other than the third compound in the present specification is the same as the measurement of the amount and ratio of Prompt emission and Delay emission of the third compound.

In the organic EL device according to the present embodiment, the third compound is preferably a compound represented by the following general formula (31) or the following general formula (32).

-Compound represented by the general formula (31)

(In the general formula (31),
n is 1, 2, 3 or 4
m is 1, 2, 3 or 4
q is 0, 1, 2, 3 or 4 and
m + n + q = 6 and
CN is a cyano group and
D ₁ is a group represented by the following general formula (3a), the following general formula (3b), or the following general formula (3c), and when there are a plurality of D ₁ , the plurality of D _1s are the same or the same. Different,
Rx is a hydrogen atom, a substituent, or adjacent pairs of Rx are bonded to each other to form a ring, and when there are a plurality of Rx, the plurality of Rx are the same or different from each other. ,
Rx as a substituent is independent of each other.
Halogen atom,
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
Substituted or unsubstituted amino groups,
Substituted or unsubstituted carbonyl group,
Substituentally substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms,
A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted ring-forming arylsilyl group having 6 to 60 carbon atoms.
CN, D ₁ and Rx are each bonded to a carbon atom of a 6-membered ring. )

(In the above general formula (3a), R ₁ to R ₈ are independently hydrogen atoms or substituents, or a set of R ₁ and R ₂ , a set of R ₂ and R ₃ , R. One or more pairs of ₃ and R ₄ , pairs R ₅ and R ₆ , pairs R ₆ and R ₇ , and pairs R ₇ and R ₈ combine with each other to form a ring.
R ₁ to R ₈ as substituents are independent of each other.
Halogen atom,
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
Substituentally substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms,
Substituentally substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
Substituentally substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms,
Hydroxy group,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
Substituent or unsubstituted alkoxy halide groups having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms,
Substituentally substituted or unsubstituted alkylamino groups having 2 to 30 carbon atoms,
Substituentally substituted or unsubstituted arylamino groups having 6 to 60 carbon atoms,
Thiol group,
A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or a substituted or unsubstituted ring-forming alkylthio group having 6 to 30 carbon atoms.
* Represents the bond position of the benzene ring with the carbon atom in the general formula (31). )

(In the general formula (3b),
Each of R ₃₁ to R ₃₈ is independently a hydrogen atom or a substituent, or a set of R ₃₁ and R ₃₂ , a set of R ₃₂ and R ₃₃ , a set of R ₃₃ and R ₃₄ , and R ₃₅ . And one or more of the R ₃₆ pairs, the R ₃₆ and R ₃₇ pairs, and the R ₃₇ and R ₃₈ pairs join together to form a ring.
R ₃₁ to R ₃₈ as substituents are independently synonymous with R ₁ to R ₈ in the general formula (3a).
A represents a ring structure represented by the following general formula (311) or the following general formula (312), and this ring structure A is condensed with an adjacent ring structure at an arbitrary position.
p is 1, 2, 3 or 4
When p is 2, 3 or 4, the plurality of ring structures A are the same as or different from each other.
* Represents the bond position of the benzene ring with the carbon atom in the general formula (31). )

(In the general formula (3c),
R ₃₀₀₁ to R ₃₀₀₈ are independently hydrogen atoms or substituents, or a set of R ₃₀₀₁ and R ₃₀₀₂ , a set of R ₃₀₀₂ and R ₃₀₀₃ , a set of R ₃₀₀₃ and R ₃₀₀₄ , and R ₃₀₀₅ . And one or more of the R ₃₀₀₆ pairs, the R ₃₀₀₆ and R ₃₀₀₇ pairs, and the R ₃₀₀₇ and R ₃₀₀₈ pairs join together to form a ring.
R ₃₀₀₁ to R ₃₀₀₈ as substituents are independently synonymous with R ₁ to R ₈ as substituents in the general formula (3a).
B represents a ring structure represented by the following general formula (311) or the following general formula (312), and this ring structure B is condensed with an adjacent ring structure at an arbitrary position.
px is 1, 2, 3 or 4
When px is 2, 3 or 4, the plurality of ring structures B are the same as or different from each other.
C represents a ring structure represented by the following general formula (311) or the following general formula (312), and this ring structure C is condensed with an adjacent ring structure at an arbitrary position.
py is 1, 2, 3 or 4
When py is 2, 3 or 4, the plurality of ring structures C are the same as or different from each other.
* Represents the bond position of the benzene ring with the carbon atom in the general formula (31). )

(In the above general formula (311), whether R ₃₀₀₉ and R ₃₀₁₀ are independently hydrogen atoms, substituents, or bonded to each other with a part of an adjacent ring structure to form a ring. Alternatively, pairs of R ₃₀₀₉ and R ₃₀₁₀ combine with each other to form a ring.
In the general formula (312), X ₃₀₁ is CR ₃₀₁₁ R ₃₀₁₂ , NR ₃₀₁₃ , a sulfur atom or an oxygen atom, and R ₃₀₁₁ , R ₃₀₁₂ and R ₃₀₁₃ are independently hydrogen atoms or substitutions. It is a group _, or R ₃₀₁₁ and R ₃₀₁₂ combine with each other to form a ring.
R ₃₀₀₉ , R ₃₀₁₀ , R ₃₀₁₁ , R ₃₀₁₂ and R ₃₀₁₃ as substituents are independently synonymous with R ₁ to R ₈ as substituents in the general formula (3a). )

In the general formula (311), R ₃₀₀₉ and R ₃₀₁₀ independently combine with a part of adjacent ring structures to form a ring, specifically, the following (I) to (IV). It means one of.
Further, in the general formula (311), the fact that the pair of R ₃₀₀₉ and R ₃₀₁₀ are combined with each other to form a ring specifically means the following (V).

(I) When the ring structures represented by the general formula (311) are adjacent to each other, a set of R ₃₀₀₉ of one ring and R ₃₀₀₉ of the other ring of the two adjacent rings, R of one ring One or more pairs of R ₃₀₁₀ of ₃₀₀₉ and the other ring, and R ₃₀₁₀ of one ring and R ₃₀₁₀ of the other ring are coupled to each other to form a ring.

(II) When the ring structure represented by the general formula (311) and the benzene ring having _R35 to _R38 in the general formula (3b) are adjacent to each other, one of the two adjacent rings A set of R ₃₀₀₉ and R ₃₅ of the other ring, a set of R ₃₀₀₉ of one ring and a set of R ₃₈ of the other ring, a set of R ₃₀₁₀ of one ring and a set of R ₃₅ of the other ring, and a set of R of one ring. Any one or more pairs of R ₃₈ pairs of ₃₀₁₀ and the other ring combine with each other to form a ring.

(III) When the ring structure represented by the general formula (311) and the benzene ring having R ₃₀₀₁ to R ₃₀₀₄ in the general formula (3c) are adjacent to each other, one of the two adjacent rings The set of R ₃₀₀₉ and R ₃₀₀₁ of the other ring, the set of R ₃₀₀₉ of one ring and the set of R ₃₀₀₄ of the other ring, the set of R ₃₀₁₀ of one ring and the set of R ₃₀₀₁ of the other ring, and the R of one ring. Any one or more pairs of R ₃₀₀₄ pairs of ₃₀₁₀ and the other ring combine with each other to form a ring.

(IV) When the ring structure represented by the general formula (311) and the benzene ring having _R3005 to _R3008 in the general formula (3c) are adjacent to each other, one of the two adjacent rings The set of R ₃₀₀₉ and R ₃₀₀₅ of the other ring, the set of R ₃₀₀₉ of one ring and the set of R ₃₀₀₈ of the other ring, the set of R ₃₀₁₀ of one ring and the set of R ₃₀₀₅ of the other ring, and the R of one ring. The combination of any one or more of the _R3008 pairs of ₃₀₁₀ and the other ring with each other to form a ring.

(V) A pair of R ₃₀₀₉ and R ₃₀₁₀ having a ring structure represented by the general formula (311) is bonded to each other to form a ring. That is, (V) means that a pair of R ₃₀₀₉ and R ₃₀₁₀ bonded to the same ring are bonded to each other to form a ring.

In the third compound of the present embodiment, Rx is independently a hydrogen atom, an aryl group having an unsubstituted ring-forming carbon number of 6 to 30, an unsubstituted heterocyclic group having 5 to 30 ring-forming atoms, and an unsubstituted ring. In the case of an alkyl group having 1 to 30 carbon atoms or an unsubstituted cycloalkyl group having 3 to 30 carbon atoms and Rx being an unsubstituted heterocyclic group having 5 to 30 atom forming atoms, there is no substitution. Rx as a heterocyclic group having 5 to 30 ring-forming atoms is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a dibenzofuranyl group, or a dibenzothienyl group.

As used herein, the triazineyl group refers to a group obtained by removing one hydrogen atom from 1,3,5-triazine, 1,2,4-triazine, or 1,2,3-triazine.
The triazineyl group is preferably a group obtained by removing one hydrogen atom from 1,3,5-triazine.

In the third compound of the present embodiment, Rx is independently a hydrogen atom, an unsubstituted aryl group having 6 to 30 carbon atoms, an unsubstituted dibenzofuranyl group, or an unsubstituted dibenzothienyl group, respectively. Is more preferable.
In the third compound of the present embodiment, Rx is more preferably a hydrogen atom.

In the third compound of the present embodiment, R ₁ to R ₈ , R ₃₁ to R ₃₈ , R ₃₀₀₁ to R ₃₀₀₈ , R ₃₀₀₉ , R ₃₀₁₀ , and R ₃₀₁₁ to R ₃₀₁₃ as substituents are independently absent. Substituent ring-forming aryl groups with 6 to 30 carbon atoms, unsubstituted ring-forming atomic groups with 5 to 30 heterocyclic groups, unsubstituted alkyl groups with 1 to 30 carbon atoms, or unsubstituted ring-forming carbon atoms with 3 to 30 carbon atoms. It is preferably 30 cycloalkyl groups.

In the third compound of the present embodiment, the D ₁ is preferably any of the groups represented by the following general formulas (D-21) to (D-27).

(In the above general formula (D-21), R ₈₃ to R ₉₀ are independently hydrogen atoms or substituents, respectively.
In the general formulas (D-22) to (D-27), X ₃₁ to X ₃₆ are independently oxygen atoms, sulfur atoms, or CR ₃₆₁ R ₃₆₂ , respectively.
R ₃₆₁ and R ₃₆₂ are independently hydrogen atoms or substituents, or R ₃₆₁ and R ₃₆₂ are bonded to each other to form a ring.
Each of R ₃₀₁ to R ₃₆₀ is independently a hydrogen atom or a substituent, or a set of R ₃₀₁ and R ₃₀₂ , a set of R ₃₀₂ and R ₃₀₃ , a set of R ₃₀₃ and R ₃₀₄ , and R _305. And R ₃₀₆ pairs, R ₃₀₇ and R ₃₀₈ pairs, R ₃₀₈ and R ₃₀₉ pairs, R ₃₀₉ and R ₃₁₀ pairs, R ₃₁₁ and R ₃₁₂ pairs, R ₃₁₂ and R ₃₁₃ pairs, R ₃₁₃ and R. A set of ₃₁₄ , a set of R ₃₁₆ and R ₃₁₇ , a set of R ₃₁₇ and R ₃₁₈ , a set of R ₃₁₈ and R ₃₁₉ , a set of R ₃₂₁ and R ₃₂₂ , a set of R ₃₂₂ and R ₃₂₃ , a set of R ₃₂₃ and R ₃₂₄ . Pairs, R ₃₂₆ and R ₃₂₇ pairs, R ₃₂₇ and R ₃₂₈ pairs, R ₃₂₈ and R ₃₂₉ pairs, R ₃₃₁ and R ₃₃₂ pairs, R ₃₃₂ and R ₃₃₃ pairs, R ₃₃₃ and R ₃₃₄ pairs, R ₃₃₅ and R ₃₃₆ pairs, R ₃₃₆ and R ₃₃₇ pairs, R ₃₃₇ and R ₃₃₈ pairs, R ₃₃₉ and R ₃₄₀ pairs, R ₃₄₁ and R ₃₄₂ pairs, R ₃₄₂ and R ₃₄₃ pairs, R ₃₄₃ pairs. And R ₃₄₄ pairs, R ₃₄₅ and R ₃₄₆ pairs, R ₃₄₆ and R ₃₄₇ pairs, R ₃₄₇ and R ₃₄₈ pairs, R ₃₄₉ and R ₃₅₀ pairs, R ₃₅₁ and R ₃₅₂ pairs, R ₃₅₂ and R. One or more of the ₃₅₃ pairs, the R ₃₅₃ and R ₃₅₄ pairs, the R ₃₅₅ and R ₃₅₆ pairs, the R ₃₅₇ and R ₃₅₈ pairs, the R ₃₅₈ and R ₃₅₉ pairs, and the R ₃₅₉ and R ₃₆₀ pairs. Pairs combine with each other to form a ring,
R ₈₃ to R ₉₀ , R ₃₀₁ to R ₃₆₀ , R ₃₆₁ and R ₃₆₂ as substituents are independent of each other.
Halogen atom,
Substituentally substituted or unsubstituted aryl groups having 6 to 14 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 14 atom-forming atoms,
Substituentally substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 6 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 8 carbon atoms,
Substituentally substituted or unsubstituted alkylsilyl group having 3 to 6 carbon atoms,
Hydroxy group,
Substituent or unsubstituted alkoxy group having 1 to 6 carbon atoms,
Substituent or unsubstituted alkoxy group having 1 to 6 carbon atoms,
Substituentally substituted or unsubstituted aryloxy groups having 6 to 14 carbon atoms,
Substituentally substituted or unsubstituted arylamino groups having 6 to 28 carbon atoms,
Substituentally substituted or unsubstituted alkylamino groups having 2 to 12 carbon atoms,
Thiol group,
A substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming alkylthio group having 6 to 14 carbon atoms.
* Represents the binding site of the benzene ring with the carbon atom in the general formula (31). )

In the third compound of the present embodiment, it is more preferable that D ₁ is a group represented by the general formula (D-21), (D-23), or (D-24).
In the third compound of the present embodiment, it is further preferable that D ₁ is a group represented by the general formula (D-21) or (D-23).

In the third compound of the present embodiment, R ₈₃ to R ₉₀ , R ₃₀₁ to R ₃₆₀ , R ₃₆₁ and R ₃₆₂ are independently hydrogen atoms, unsubstituted aryl groups having 6 to 14 ring-forming carbon atoms, and none. Substituted ring-forming A heterocyclic group having 5 to 14 atoms or an unsubstituted alkyl group having 1 to 6 carbon atoms is preferable.

In the third compound of the present embodiment, R ₈₃ to R ₉₀ and R ₃₀₁ to R ₃₆₀ are preferably hydrogen atoms.
In the third compound of the present embodiment, R ₃₆₁ and R ₃₆₂ are independently an aryl group having an unsubstituted ring-forming carbon number of 6 to 14, a heterocyclic group having an unsubstituted ring-forming atom number of 5 to 14, respectively. It is preferably an unsubstituted alkyl group having 1 to 6 carbon atoms.

-Compound represented by the general formula (32)

(In the above general formula (32), Ar ₁ is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms, substituted or unsubstituted. Alkyl group with 1 to 30 carbon atoms, substituted or unsubstituted fluoroalkyl group with 1 to 30 carbon atoms, substituted or unsubstituted ring-forming cycloalkyl group with 3 to 30 carbon atoms, substituted or unsubstituted carbon number 7 Any group selected from the group consisting of ~ 30 aralkyl groups, substituted phosphoryl groups, substituted silyl groups, cyano groups, nitro groups, carboxy groups, and groups represented by the following general formulas (1a) to (1j). And
Ar _EWG has a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms containing one or more nitrogen atoms in the ring, or a ring-forming carbon number of 6 to 30 substituted with one or more cyano groups. Aryl group of
Ar _X is independently a hydrogen atom or a substituent, and Ar _X as a substituent is an aryl group having 6 to 30 substituted or unsubstituted ring-forming carbon atoms and a substituted or unsubstituted ring-forming atom number. 5 to 30 heteroaryl groups, substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted fluoroalkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted ring-forming carbon groups having 3 to 30 carbon atoms. It is represented by a cycloalkyl group, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted phosphoryl group, a substituted silyl group, a cyano group, a nitro group, a carboxy group, and the following general formulas (1a) to (1j). Any group selected from the group consisting of groups,
When n is 0, 1, 2, 3, 4 or 5, and n is 2, 3, 4 or 5, the plurality of Ar _Xs are the same as or different from each other.
The ring (F) is a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocycle, and the ring (F) is a 5-membered ring, a 6-membered ring, or a 7-membered ring, Ar. _EWG , Ar ₁ and Ar _X are each bound to the elements constituting the ring (F) and are bonded to each other.
At least one of Ar ₁ and Ar _X is any group selected from the group consisting of the groups represented by the following general formulas (1a) to (1j). )

(In the general formulas (1a) to (1j), X1 to _X20 are independently carbon atoms ( _CRA1 ) to which _a nitrogen atom (N) or _RA1 is bonded.
_In the general formula (1b), any of _X5 to X8 is a carbon atom bonded to any of _X9 to _X12 , and any of _X9 to _X12 is any of _X5 to _X8 . It is a carbon atom that bonds to the heel.
_In the general formula (1c), any one of _X5 to X8 is a carbon atom bonded to a nitrogen atom in a ring containing A ₂ .
_In the general formula (1e), any of _X5 to _X8 and X18 is a carbon atom bonded to any of _X9 to _X12 , and any of _X9 to _X12 is _X5 to X. A carbon atom that bonds to any of ₈ and _X18 .
_In the general formula (1f), any of _X5 to _X8 and X18 is a carbon atom bonded to any of _X9 to _X12 and _X19 , and any of _X9 to _X12 and _X19 . Is a carbon atom bonded to any of _X5 to _X8 and _X18 .
In the general formula (1 g), any of _X5 to _X8 is a carbon atom bonded to any of _X9 to _X12 and _X19 , and any of _X9 to _X12 and _X19 is X. It is a carbon atom bonded to any of ₅ to _X8 , and is a carbon atom.
_In the general formula (1h), any one of _X5 to _X8 and X18 is a carbon atom bonded to a nitrogen atom in a ring containing A ₂ .
_In the general formula (1i), any one of _X5 to _X8 and _X18 is a nitrogen atom connecting a ring containing _X9 to _X12 and _X19 and a ring containing _X13 to _X16 and X20. Is a carbon atom that binds to
_In the general formula (1j), any one of _X5 to X8 is bonded to a nitrogen atom connecting a ring containing _X9 to _X12 and _X19 and a ring containing _X13 to _X16 and _X20 . It is a carbon atom
Each _RA1 is independently a hydrogen atom, a substituent, or one or more pairs of a plurality of _RA1s directly bonded to each other to form a ring. Forming a ring through heteroatoms,
_RA1 as a substituent is an aryl group having 6 to 30 substituted or unsubstituted ring-forming carbon atoms, a heteroaryl group having 5 to 30 substituted or unsubstituted ring-forming atoms, and 1 to 1 substituted or unsubstituted ring-forming atom. 30 alkyl groups, substituted or unsubstituted fluoroalkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms. , A substituted phosphoryl group, a substituted silyl group, a cyano group, a nitro group, and any group selected from the group consisting of a carboxy group.
Multiple _RA1s as substituents are the same as or different from each other.
In the general formulas (1a) to (1j), * represents a bonding position with the ring (F).
In the general formulas (1a) to (1j), A ₁ and A ₂ are independently single-bonded, oxygen atom (O), sulfur atom (S), C (R ₃₀₂₁ ) (R ₃₀₂₂ ), Si ( R ₃₀₂₃ ) (R ₃₀₂₄ ), C (= O), S (= O), SO ₂ or N (R ₃₀₂₅ ). R ₃₀₂₁ to R ₃₀₂₅ are independently hydrogen atoms or substituents, and R ₃₀₂₁ to R ₃₀₂₅ as substituents are independently substituents or unsubstituted aryls having 6 to 30 ring-forming carbon atoms. Group, substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted. From the group consisting of an unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted phosphoryl group, a substituted silyl group, a cyano group, a nitro group, and a carboxy group. Is one of the groups selected and
In the general formulas (1a) to (1j), Ara is an aryl group having 6 to 30 substituted or unsubstituted ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms, substituted or substituted. Unsubstituted alkyl groups with 1 to 30 carbon atoms, substituted or unsubstituted fluoroalkyl groups with 1 to 30 carbon atoms, substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 30 carbon atoms, substituted or unsubstituted carbons. It is any group selected from the group consisting of an aralkyl group having a number of 7 to 30, a substituted phosphoryl group, and a substituted silyl group. )

In the general formula (1a), when X ₁ to X ₈ are carbon atoms (C- _RA1 ) to which _{RA1 is bonded, it is preferable that the plurality of RA1s do} not form a ring.
In the general formulas (1a) to (1j), an aryl group having a substituted or unsubstituted ring-forming carbon number of 6 to 30 or a heteroaryl group having a substituted or unsubstituted ring-forming atom number of 5 to 30 is preferable as Ara. Is.

The general formula (1a) is represented by the following general formula (1aa) when A ₁ is a single bond, the following general formula (1ab) when A ₁ is O, and A ₁ is S. In some cases, it is represented by the following general formula (1ac), when A ₁ is C (R ₃₀₂₁ ) (R ₃₀₂₂ ), it is represented by the following general formula (1ad), and A ₁ is Si (R ₃₀₂₃ ) (R ₃₀₂₄ ). ), It is represented by the following general formula (1ae), when A ₁ is C (= O), it is represented by the following general formula (1af), and when A ₁ is S (= O), it is represented by the following. It is represented by the general formula (1ag), when A ₁ is SO ₂ , it is represented by the following general formula (1 ah), and when A ₁ is N (R ₃₀₂₅ ), it is represented by the following general formula (1 ai). In these general formulas (1aa) to (1ai) below, X ₁ to X ₈ and R ₃₀₂₁ to R ₃₀₂₅ have the same meanings as described above. Regarding the general formulas ( _1b ), (1c), (1e), (1g) to (1j), the mode of connecting the rings by A1 and _A2 is the same as the following general formulas (1aa) to (1ai). Is. In the following general formula (1aa), when X ₁ to X ₈ are carbon atoms (C- _RA1 ) to which _{RA1 is bonded, it is preferable that a plurality of RA1s as} substituents do not form a ring.

The third compound is preferably represented by the following general formula (321).

The Ar ₁ , Ar _EWG , Ar _x , n and the ring (F) in the general formula (321) are the Ar ₁ , Ar _EWG , Ar _x , n and the ring (F) in the general formula (32), respectively. It is synonymous with F).

The third compound is also preferably represented by the following general formula (322).

In the general formula (322), Y ₁ to Y ₅ are independently represented by a nitrogen atom (N), a carbon atom to which a cyano group is bonded (C—CN), or a carbon atom to which RA 2 is bonded ( _{CR A2 )} . ), And at _{least one} of Y1 to Y5 is N or C-CN. Multiple _RA2s are the same as or different from each other. _RA2 is a hydrogen atom or a substituent independently of each other, and _RA2 as a substituent is an aryl group having 6 to 30 substituted or unsubstituted ring-forming carbon atoms and 5 substituted or unsubstituted ring-forming atoms. ~ 30 heteroaryl groups, substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted fluoroalkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted ring-forming cyclos having 3 to 30 carbon atoms. A group selected from the group consisting of an alkyl group, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted phosphoryl group, a substituted silyl group, a cyano group, a nitro group, and a carboxy group.
Multiple _RA2s are the same as or different from each other.

In the general formula (322), Ar ₁ is synonymous with Ar ₁ in the general formula (32).

In the general formula (322), Ar ₂ to Ar ₅ are independently hydrogen atoms or substituents, and Ar ₂ to Ar ₅ as a substituent are independently substituted or unsubstituted ring-forming carbons. An aryl group having 6 to 30, a substituted or unsubstituted heteroaryl group having 5 to 30 atoms, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms. Fluoroalkyl group, substituted or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms, substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, substituted phosphoryl group, substituted silyl group, cyano group, nitro group, carboxy It is any group selected from the group consisting of a group and a group represented by the general formulas (1a) to (1c).

In the general formula (322), at least one of Ar ₁ to Ar ₅ is any group selected from the group consisting of the groups represented by the general formulas (1a) to (1c).

The third compound is also preferably a compound represented by the following general formula (11aa), the following general formula (11bb), or the following general formula (11cc).

In the general formulas ( _11aa ), (11bb) and ( _11cc ), Y1 to Y5, _RA2 , Ar2 to _Ar5 , _X1 to _X16 , _RA1 and Ara are the above _- mentioned Y1 to Ara, _respectively . It has the same meaning as Y ₅ , _{RA 2} , Ar ₂ to Ar ₅ , X ₁ to X ₁₆ , RA ₁ , and Ara.

In the organic EL device according to the present embodiment, the third compound is preferably the compound represented by the general formula (31).

-Method for producing the third compound The third compound of the present embodiment can be produced, for example, by a known method. In addition, the third compound of the present embodiment can be produced by following a known method and using a known alternative reaction or raw material suitable for the desired product.

-Specific Examples of the Third Compound Examples of specific examples of the third compound of the present embodiment include the following compounds. However, the present invention is not limited to specific examples of these compounds.

FIG. 4 is a diagram for explaining the principle of light emission according to the embodiment of the present invention.
In FIG. 4, S0 represents the ground state. S1 (M1) represents the lowest excited singlet state of the first compound, and T1 (M1) represents the lowest excited triplet state of the first compound. S1 (M2) represents the lowest excited singlet state of the second compound, and T1 (M2) represents the lowest excited triplet state of the second compound. S1 (M3) represents the lowest excited singlet state of the third compound, and T1 (M3) represents the lowest excited triplet state of the third compound.
As shown in FIG. 4, when a compound having a small ΔST (M3) is used as the third compound, the lowest excited triplet state T1 (M3) of the third compound is the lowest excited singlet state S1 (M3) due to thermal energy. Intersystem crossing is possible.
By utilizing the inverse intersystem crossing generated by this third compound, for example, luminescence as shown in the following (i) or the following (ii) can be observed.
(I) When the light emitting layer does not contain the fluorescence dopant of the lowest excited singlet state S1 smaller than the lowest excited singlet state S1 (M3) of the third compound, the lowest excited singlet state S1 (M3) of the third compound. ) Can be observed.
(Ii) When the light emitting layer contains a fluorescent dopant (fluorescent fourth compound in the second embodiment) of the lowest excited singlet state S1 smaller than the lowest excited singlet state S1 (M3) of the third compound. , The emission from the fluorescent dopant can be observed.
In the organic EL device of the first embodiment, the light emission shown in (i) above can be observed. In the organic EL device of the second embodiment described later, the light emission shown in (ii) can be observed.

-Relationship between triplet energy and energy gap at 77 [K] Here, the relationship between triplet energy and the energy gap at 77 [K] will be described. In this embodiment, the energy gap at 77 [K] is different from the normally defined triplet energy.
The triplet energy measurement is performed as follows. First, a sample is prepared by enclosing a solution in which a compound to be measured is dissolved in an appropriate solvent in a quartz glass tube. For this sample, the phosphorescence spectrum (vertical axis: phosphorescence emission intensity, horizontal axis: wavelength) was measured at a low temperature (77 [K]), and a tangent line was drawn with respect to the rising edge of the phosphorescence spectrum on the short wavelength side. The triple term energy is calculated from a predetermined conversion formula based on the wavelength value of the intersection of the tangent line and the horizontal axis.
Here, among the compounds according to the present embodiment, the thermally active delayed fluorescent compound is preferably a compound having a small ΔST. When ΔST is small, intersystem crossing and inverse intersystem crossing are likely to occur even in a low temperature (77 [K]) state, and an excited singlet state and an excited triplet state coexist. As a result, the spectrum measured in the same manner as described above contains light 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 value of triplet energy is considered to be dominant.
Therefore, in the present embodiment, the measurement method is the same as that of the normal triplet energy T, but in order to distinguish the difference in the strict sense, the value measured as follows is referred to as an energy gap T _77K . .. The compound to be measured is dissolved in EPA (diethyl ether: isopentan: 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 for measurement. Use as a sample. For this measurement sample, the 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 line and the horizontal axis, the amount of energy calculated from the following conversion formula (F1) is defined as the energy gap T _77K in 77 [K].
Conversion formula (F1): T _77K [eV] = 1239.85 / λ _edge

The tangent to the rising edge of the phosphorescence spectrum on the short wavelength side 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 of the maximum values of the spectrum, consider the tangents at each point on the curve toward the long wavelength side. This tangent increases in slope as the curve rises (ie, as the vertical axis increases). The tangent line drawn at the point where the value of the slope reaches the maximum value (that is, the tangent line at the inflection point) is regarded as the tangent line with respect to the rising edge of the phosphorescence spectrum on the short wavelength side.
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 the value of the gradient closest to the maximum value on the shortest wavelength side is the maximum. The tangent line drawn at the point where the value is taken is taken as the tangent line to the rising edge of the phosphorescent spectrum on the short wavelength side.
For the measurement of phosphorescence, an F-4500 type spectrofluorometer main body manufactured by Hitachi High-Technology Co., Ltd. can be used. The measuring device is not limited to this, and may be measured by combining a cooling device, a low temperature container, an excitation light source, and a light receiving device.

・ Singlet energy S ₁
Examples of the method for measuring the singlet energy S1 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, 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 for the fall on the long wavelength side of this absorption spectrum, and the wavelength value λedge [nm] at the intersection of the tangent line and the horizontal axis is substituted into the conversion formula (F2) shown below to calculate the single term energy. do.
Conversion formula (F2): S ₁ [eV] = 1239.85 / λedge
Examples of the absorption spectrum measuring device include, but are not limited to, a spectrophotometer manufactured by Hitachi, Ltd. (device name: U3310).

The tangent to the fall 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, consider the tangents at each point on the curve. This tangent repeats as the curve descends (ie, as the value on the vertical axis decreases), the slope decreases, and then increases. The tangent line drawn at the point where the slope value is the longest wavelength side (except when the absorbance is 0.1 or less) takes the minimum value is defined as the tangent line to the fall of the absorption spectrum on the long wavelength side.
The maximum point having an absorbance value of 0.2 or less is not included in the maximum value on the longest wavelength side.

・ ΔST
In the present embodiment, the difference (S1 _- T _77K ) between the singlet energy S ₁ and the energy gap T _77K at 77 [K] is defined as ΔST.

In the present embodiment, the difference ΔST (M3) between the single term energy S ₁ (M3) of the third compound and the energy gap T _77K (M3) in 77 [K] of the third compound is preferably less than 0.3 eV. , More preferably less than 0.2 eV, still more preferably less than 0.1 eV, still more preferably less than 0.01 eV. It is preferable that ΔST (M3) satisfies any of the following mathematical expressions (Equation 1A) to (Equation 1D).
ΔST (M3) = S ₁ (M3) -T _77K (M3) <0.3eV ... (Equation 1A)
ΔST (M3) = S ₁ (M3) -T _77K (M3) <0.2eV ... (Equation 1B)
ΔST (M3) = S ₁ (M3) -T _77K (M3) <0.1eV ... (Equation 1C)
ΔST (M3) = S ₁ (M3) -T _77K (M3) <0.01eV ... (Equation 1D)

-Compound content in the light emitting layer The content of the first compound, the second compound, and the third compound contained in the light emitting layer is preferably in the following range, for example.
The total content of the first compound and the second compound in the light emitting layer is preferably 10% by mass or more and 90% by mass or less.
The ratio of the content of the first compound to the content of the second compound in the light emitting layer is preferably 1: 9 to 9: 1, more preferably 3: 7 to 7: 3. It is more preferably 4: 6 to 6: 4.
The content of the third compound is preferably 10% by mass or more and 90% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and 20% by mass or more and 60% by mass. Is more preferable.
The upper limit of the total content of the first compound, the second compound, and the third compound in the light emitting layer is 100% by mass. In addition, this embodiment does not exclude that the light emitting layer contains a material other than the first compound, the second compound, and the third compound.
The light emitting layer may contain only one kind of the first compound, or may contain two or more kinds. The light emitting layer may contain only one kind of the second compound, or may contain two or more kinds. The light emitting layer may contain only one kind of the tertiary compound, or may contain two or more kinds.

The film thickness of the light emitting layer The film thickness of the light emitting layer in the organic EL device according to the present embodiment is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and further preferably 10 nm or more and 50 nm or less. .. When the film thickness of the light emitting layer is 5 nm or more, it is easy to form the light emitting layer and it is easy to adjust the chromaticity. When the film thickness of the light emitting layer is 50 nm or less, an increase in the drive voltage is likely to be suppressed.

The configuration of the organic EL element will be further described.

(substrate)
The substrate is used as a support for an organic EL element. As the substrate, for example, glass, quartz, plastic, or the like can be used. Further, a flexible substrate may be used. The flexible substrate is a bendable (flexible) substrate, and examples thereof include a plastic substrate. Examples of the material for forming the plastic substrate include polycarbonate, polyarylate, polyether sulfone, polypropylene, polyester, polyvinyl fluoride, polyvinyl chloride, polyimide, polyethylene naphthalate and the like. Inorganic vapor deposition film can also be used.

(anode)
For the anode formed on the substrate, it is preferable to use a metal having a large work function (specifically, 4.0 eV or more), an alloy, an electrically conductive compound, a mixture thereof, or the like. Specifically, for example, indium tin oxide (ITO: Indium Tin Oxide), indium tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, and indium oxide containing zinc oxide. , Graphene and the like. 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 nitride of a metallic material (for example, titanium nitride) and the like can be mentioned.

These materials are usually formed by a sputtering method. For example, indium oxide-zinc oxide can be formed by a sputtering method by using a target in which zinc oxide is added in an amount of 1% by mass or more and 10% by mass or less with respect to indium oxide. Further, for example, indium oxide containing tungsten oxide and zinc oxide contained 0.5% by mass or more and 5% by mass or less of tungsten oxide and 0.1% by mass or more and 1% by mass or less of zinc oxide with respect to indium oxide. By using a target, it can be formed by a sputtering method. In addition, it may be produced by a vacuum vapor deposition method, a coating method, an inkjet method, a spin coating method, or the like.

Of the EL layers formed on the anode, the hole injection layer formed in contact with the anode is formed by using a composite material that facilitates hole injection regardless of the work function of the anode. , Materials that can be used as electrode materials (for example, metals, alloys, electrically conductive compounds, and mixtures thereof, and other elements belonging to Group 1 or Group 2 of the Periodic Table of the Elements) can be used.

Elements belonging to Group 1 or Group 2 of the Periodic Table of the Elements, which are materials with a small work function, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg), calcium (Ca), and strontium. Alkali earth metals such as (Sr), rare earth metals such as alloys containing these (for example, MgAg, AlLi), europium (Eu), and itterbium (Yb), and alloys containing these can also be used. When forming an anode using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum vapor deposition method or a sputtering method can be used. Further, when a silver paste or the like is used, a coating method, an inkjet method, or the like can be used.

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

When forming a cathode using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum vapor deposition method or a sputtering method can be used. When a silver paste or the like is used, a coating method, an inkjet method, or the like can be used.

By providing the electron injection layer, a cathode is formed by using various conductive materials such as indium oxide containing silicon or silicon oxide, regardless of the size of the work function, such as Al, Ag, ITO, graphene, silicon or silicon oxide. can do. These conductive materials can be formed into a film by using 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, renium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, and silver oxide. Tungsten oxide, manganese oxide and the like can be used.

Further, as a substance having high hole injectability, 4,4', 4''-tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4,4', which is a low molecular weight 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-yl) -N -Phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis [N- (9-phenylcarbazole-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA2), Aromatic amine compounds such as 3- [N- (1-naphthyl) -N- (9-phenylcarbazole-3-yl) amino] -9-phenylcarbazole (abbreviation: PCzPCN1) and dipyrazino [2,3-f : 20,30-h] Kinoxalin-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) can also be mentioned.

Further, as the substance having high hole injection property, a polymer compound (oligomer, dendrimer, polymer, etc.) 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) methacrylicamide] (abbreviation: PTPDMA), poly [N, N'-bis (4-butylphenyl) -N, N'-bis (phenyl) benzidine] (abbreviation: Poly-TPD) and other high molecular weight compounds can be mentioned. Further, a polymer compound to which an acid such as poly (3,4-ethylenedioxythiophene) / poly (styrene sulfonic acid) (PEDOT / PSS) and polyaniline / poly (styrene sulfonic acid) (Pani / PSS) is added is used. You can also do it.

(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) and 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 An aromatic amine compound such as [N- (spiro-9,9'-bifluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: BSBP) can be used. The substances described here are mainly substances having a hole mobility of ^10-6 cm ² / (V · s) or more.

The hole transport layer includes CBP, 9- [4- (N-carbazolyl)] phenyl-10-phenylanthracene (CzPA), 9-phenyl-3- [4- (10-phenyl-9-anthril) phenyl]. Carbazole derivatives such as -9H-carbazole (PCzPA) and anthracene derivatives such as t-BuDNA, DNA and DPAnth may be used. Polymer compounds such as poly (N-vinylcarbazole) (abbreviation: PVK) and poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.

However, any substance other than these may be used as long as it is a substance having a higher hole transport property than electrons. The layer containing a substance having a high hole transport property is not limited to a single layer, but may be a layer in which two or more layers made of the above substances are laminated.

When two or more hole transport layers are arranged, it is preferable to arrange a material having a larger energy gap closer to the light emitting layer. Examples of such a material include compound EBL and compound EBL-2 used in the examples described later.

(Electron transport layer)
The electron transport layer is a layer containing a substance having a high electron transport property. The electron transport layer includes 1) a metal complex such as an aluminum complex, a berylium complex, and a zinc complex, 2) a complex aromatic compound such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative, and a phenanthroline derivative, and 3) a polymer compound. Can be used. Specifically, as small molecule organic compounds, Alq, tris (4-methyl-8-quinolinolat) aluminum (abbreviation: Almq ₃ ), bis (10-hydroxybenzo [h] quinolinato) beryllium (abbreviation: BeBq ₂ ), Metal complexes such as BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition to the metal complex, 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis [5- (Ptert-butylphenyl) -1,3,4-oxadiazole-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- Complexes such as triazole (abbreviation: p-EtTAZ), vasofenantroline (abbreviation: BPhen), vasocuproin (abbreviation: BCP), 4,4'-bis (5-methylbenzoxazole-2-yl) stilben (abbreviation: BzOs) Aromatic compounds can also be used. In this embodiment, a benzimidazole compound can be preferably used. The substances described here are mainly substances having electron mobility of ^10-6 cm ² / (V · s) or more. A substance other than the above may be used as the electron transport layer as long as it is a substance having a higher electron transport property than the hole transport property. Further, the electron transport layer may be composed of a single layer, or may be configured by laminating two or more layers made of the above substances.

Further, a polymer compound can also be used for the electron transport 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. The electron injection layer includes lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), lithium oxide (LiOx), etc. Alkali metals such as, alkaline earth metals, or compounds thereof can be used. In addition, a substance having an electron transport property containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a substance containing magnesium (Mg) 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 an organic compound by an electron donor. In this case, the organic compound is preferably a material excellent in transporting generated electrons, and specifically, for example, a substance (metal complex, heteroaromatic compound, etc.) constituting the above-mentioned electron transport layer is used. be able to. The electron donor may be any substance that exhibits 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 mentioned. Further, alkali metal oxides and alkaline earth metal oxides are preferable, and lithium oxides, calcium oxides, barium oxides and the like can be mentioned. It is also possible to use a Lewis base such as magnesium oxide. Further, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can also 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 is limited to dry film deposition methods such as vacuum vapor deposition method, sputtering method, plasma method, ion plating method, and spin. Known methods such as a coating method, a dipping method, a flow coating method, and a wet film forming method such as an inkjet method can be adopted.
In the present embodiment, it is also preferable that the light emitting layer is formed by using a composition containing the first compound and the second compound as a vapor deposition source. By using the composition, the number of vapor deposition sources can be reduced when forming the light emitting layer.

(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, but in general, if the film thickness is too thin, defects such as pinholes are likely to occur, and conversely, if the film thickness is too thick, it is high. Since an applied voltage is required and efficiency is deteriorated, a range of several nm to 1 μm is usually preferable.

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

The organic EL element of the second embodiment is in that the light emitting layer contains a fluorescent fourth compound of the lowest excited singlet state S1 smaller than the lowest excited singlet state S1 (M3) of the third compound. , Different from the organic EL element of the first embodiment. Other points are the same as those in the first embodiment.

In the organic EL element according to the present embodiment, the light emitting layer further contains a fluorescent fourth compound, and has a singlet energy S ₁ (M3) of the third compound and a singlet energy S ₁ (M4) of the fourth compound. ) Satisfies the relationship of the following formula (Equation 3).
S ₁ (M3)> S ₁ (M4) ... (Equation 3)

In the present embodiment, the light emitting layer includes the first compound represented by the general formula (1) and the second compound as a co-matrix together with the delayed fluorescent third compound and the fluorescent emission fourth compound. including.
In this embodiment, the delayed fluorescent tertiary compound is also preferably a host material. The third compound when it is a host material may be simply referred to as a "host material".
In the present embodiment, the fluorescent fourth compound is preferably a dopant material (sometimes referred to as a guest material, an emitter, or a light emitting material).

(Fourth compound)
The light emitting layer of this embodiment contains a fluorescent fourth compound.
The fourth compound of this embodiment is not a phosphorescent metal complex. The fourth compound of the present embodiment is preferably not a heavy metal complex. Moreover, it is preferable that the fourth compound of this embodiment is not a metal complex.
Further, the fourth compound of the present embodiment is preferably a compound that does not exhibit thermally activated delayed fluorescence.

As the fourth compound of the present embodiment, a fluorescent light-emitting material can be used. Specific examples of the fluorescent light-emitting material include, for example, a bisarylaminonaphthalene derivative, an aryl-substituted naphthalene derivative, a bisarylaminoanthracene derivative, an aryl-substituted anthracene derivative, a bisarylaminopyrene derivative, an aryl-substituted pyrene derivative, and a bisarylamino. Chrysen derivative, aryl substituted chrysen derivative, bisarylaminofluoranthen derivative, aryl substituted fluorenten derivative, indenoperylene derivative, acenaftfluoranthen derivative, compound containing boron atom, pyrromethene boron complex compound, compound having pyrromethene skeleton, Examples thereof include a metal complex of a compound having a pyrromethene skeleton, a diketopyrrolopyrrole derivative, a perylene derivative, and a naphthacene derivative.

When the fourth compound is a fluorescently luminescent compound, it is preferable that the fourth compound exhibits light emission having a main peak wavelength of 400 nm or more and 700 nm or less.
In the present specification, the main peak wavelength means that the emission intensity in the measured fluorescence spectrum is the maximum for a toluene solution in which the compound to be measured is dissolved at a concentration of ^10-6 mol / liter or more and ^10-5 mol / liter or less. Refers to the peak wavelength of the fluorescence spectrum. A spectroscopic fluorometer (F-7000, manufactured by Hitachi High-Tech Science Corporation) is used as the measuring device.

The fourth compound preferably exhibits red luminescence or green luminescence.
In the present specification, the red emission means the emission in which the main peak wavelength of the fluorescence spectrum is in the range of 600 nm or more and 660 nm or less.
When the fourth compound is a red fluorescent light emitting compound, the main peak wavelength of the fourth compound is preferably 600 nm or more and 660 nm or less, more preferably 600 nm or more and 640 nm or less, and further preferably 610 nm or more and 630 nm or less.
As used herein, the term "green emission" refers to emission in which the main peak wavelength of the fluorescence spectrum is in the range of 500 nm or more and 560 nm or less.
When the fourth compound is a green fluorescent light emitting compound, the main peak wavelength of the fourth 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 540 nm or less.
As used herein, the term "blue emission" refers to emission in which the main peak wavelength of the fluorescence spectrum is in the range of 430 nm or more and 480 nm or less.
When the fourth compound is a blue fluorescent light-emitting compound, the main peak wavelength of the fourth compound is preferably 430 nm or more and 480 nm or less, and more preferably 440 nm or more and 480 nm or less.

The main peak wavelength of the light emitted from the organic EL element is measured as follows.
The spectral radiance spectrum when a voltage is applied to the organic EL element so that the current density is 10 mA / cm ² is measured with a spectral radiance meter CS-2000 (manufactured by Konica Minolta).
In the obtained spectral radiance spectrum, the peak wavelength of the emission spectrum having the maximum emission intensity is measured, and this is defined as the main peak wavelength (unit: nm).

-Method for producing the fourth compound The fourth compound of the present embodiment can be produced by, for example, a known method. In addition, the fourth compound of the present embodiment can be produced by following a known method and using a known alternative reaction or raw material suitable for the desired product.

<Relationship between the first compound, the second compound, the third compound and the fourth compound in the light emitting layer>
In the organic EL element of the present embodiment, the singlet energy S ₁ (M1) of the first compound and the singlet energy S ₁ (M3) of the third compound satisfy the relationship of the following mathematical formula (Equation 1).
Further, the singlet energy S ₁ (M2) of the second compound and the singlet energy S ₁ (M3) of the third compound satisfy the relationship of the following mathematical formula (Equation 2).
S ₁ (M1)> S ₁ (M3) ... (Equation 1)
S ₁ (M2)> S ₁ (M3) ... (number 2)

It is preferable that the singlet energy S ₁ (M1) of the first compound and the singlet energy S ₁ (M4) of the fourth compound satisfy the relationship of the following mathematical formula (Equation 4).
It is preferable that the singlet energy S ₁ (M2) of the second compound and the singlet energy S ₁ (M4) of the fourth compound satisfy the relationship of the following mathematical formula (Equation 5).
S ₁ (M1)> S ₁ (M4) ... (number 4)
S ₁ (M2)> S ₁ (M4) ... (Equation 5)

The single-term energy S ₁ (M1) of the first compound, the single-term energy S ₁ (M3) of the third compound, and the single-term energy S ₁ (M4) of the fourth compound are expressed in the following mathematical formula (Equation 6). It is preferable to satisfy the relationship.
S ₁ (M1)> S ₁ (M3)> S ₁ (M4) ... (Equation 6)
The single-term energy S ₁ (M2) of the second compound, the single-term energy S ₁ (M3) of the third compound, and the single-term energy S ₁ (M4) of the fourth compound are expressed in the following mathematical formula (Equation 7). It is preferable to satisfy the relationship.
S ₁ (M2)> S ₁ (M3)> S ₁ (M4) ... (Equation 7)

The magnitude relationship between the singlet energy S ₁ (M1) of the first compound and the singlet energy S ₁ (M2) of the second compound does not matter.
In one embodiment, the singlet energy S ₁ (M1) of the first compound is greater than the singlet energy S ₁ (M2) of the second compound.
In one embodiment, the singlet energy S ₁ (M1) of the first compound is smaller than the singlet energy S ₁ (M2) of the second compound.
In one embodiment, the singlet energy S ₁ (M1) of the first compound and the singlet energy S ₁ (M2) of the second compound are equal.

When the organic EL element of the present embodiment is made to emit light, it is preferable that the first compound and the second compound do not mainly emit light in the light emitting layer. Further, it is preferable that the third compound also mainly does not emit light.
When the organic EL element of the present embodiment is made to emit light, it is preferable that the fourth compound having fluorescence emission is mainly emitted in the light emitting layer.
The organic EL element of the present embodiment preferably emits red light or green light.

FIG. 5 is a diagram showing the relationship between the energy levels of the first compound, the second compound, the third compound and the fourth compound, and the energy transfer in the light emitting layer of the organic EL element according to the second embodiment. In the organic EL device of the second embodiment, the light emission shown in (ii) can be observed.
FIG. 5 further shows the lowest excited singlet state S1 (M4) and the lowest excited triplet state T1 (M4) of the fourth compound with respect to FIG.
The dashed arrow from S1 (M3) to S1 (M4) in FIG. 5 represents the Felster-type energy transfer from the lowest excited singlet state of the third compound to the lowest excited singlet state of the fourth compound.
As shown in FIG. 5, when a compound having a small ΔST (M3) is used as the third compound, the lowest excited triplet state T1 (M3) is converted to the lowest excited singlet state S1 (M3) by thermal energy. Crossing is possible. Then, Felster-type energy transfer from the lowest excited singlet state S1 (M3) of the third compound to the fourth compound occurs, and the lowest excited singlet state S1 (M4) is generated. As a result, the emission of the fourth compound from the lowest excited singlet state S1 (M4) 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.

The organic EL element of the second embodiment has a first compound having a singlet energy larger than that of the third compound as a co-matrix together with a delayed fluorescent third compound in a light emitting layer, and a third compound larger than the third compound. It contains a second compound having singlet energy, and further contains a fourth compound having fluorescence emission.
According to the second embodiment, a high-performance organic EL element is realized.

-Compound content in the light emitting layer The content of the first compound, the second compound, the third compound and the fourth compound contained in the light emitting layer is preferably in the following range, for example.
The total content of the first compound and the second compound in the light emitting layer is preferably 10% by mass or more and 80% by mass or less.
The ratio of the content of the first compound to the content of the second compound in the light emitting layer is preferably 1: 9 to 9: 1, more preferably 3: 7 to 7: 3. It is more preferably 4: 6 to 6: 4.
The content of the third compound is preferably 10% by mass or more and 80% by mass or less, more preferably 10% by mass or more and 60% by mass or less, and further preferably 20% by mass or more and 60% by mass or less. ..
The content of the fourth compound is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.01% by mass or more and 5% by mass or less, and 0.01% by mass or more and 1% by mass or less. The following is more preferable.
The upper limit of the total content of the first compound, the second compound, the third compound and the fourth compound in the light emitting layer is 100% by mass. In addition, this embodiment does not exclude that the light emitting layer contains a material other than the first compound, the second compound, the third compound and the fourth compound.
The light emitting layer may contain only one kind of the first compound, or may contain two or more kinds. The light emitting layer may contain only one kind of the second compound, or may contain two or more kinds. The light emitting layer may contain only one kind of the tertiary compound, or may contain two or more kinds. The light emitting layer may contain only one kind of the fourth compound, or may contain two or more kinds.

[Third Embodiment]
(Composition)
The composition according to one embodiment of the third embodiment includes the first compound and the second compound described in the first embodiment.

Preferred examples and specific examples of the first compound and the second compound contained in the composition of the present embodiment are the same as those of the first embodiment.

The ratio of the content (% by mass) of the first compound contained in the composition of the present embodiment to the content (% by mass) of the second compound is preferably 1: 9 to 9: 1. : 7 to 7: 3 is more preferable, and 4: 6 to 6: 4 is even more preferable.
The upper limit of the total value of the content of the first compound and the content of the second compound contained in the composition of the present embodiment is 100% by mass.
The composition of the present embodiment comprises, for example, only the first compound and the second compound.
The composition of the present embodiment contains, for example, materials other than the first compound and the second compound. When the composition of the present embodiment further contains other compounds, the other compounds may be solid or liquid.

The composition of the present embodiment may contain only one kind of the first compound, or may contain two or more kinds.
The composition of the present embodiment may contain only one kind of the second compound, or may contain two or more kinds.

The composition of the present embodiment is preferably used for forming an organic layer of an organic EL device, and more preferably used for forming a light emitting layer.

The organic layer (preferably a light emitting layer) of the organic EL device according to the embodiment is preferably a layer formed by using a composition containing the first compound and the second compound as a vapor deposition source.
For example, in the light emitting layer of the organic EL element according to the first embodiment, the composition of the present embodiment (composition containing the first compound and the second compound) is used as the first vapor deposition source, and the third compound is used as the first vapor deposition source. It is preferable that the layer is formed by using it as a second vapor deposition source different from the one vapor deposition source.
For example, in the light emitting layer of the organic EL element according to the second embodiment, the composition of the present embodiment (composition containing the first compound and the second compound) is used as the first vapor deposition source, and the third compound is used as the first vapor deposition source. It is preferable that the layer is used as a second vapor deposition source different from the first vapor deposition source and is formed by using the fourth compound as the third vapor deposition source.

By using the composition of the present embodiment, the number of vapor deposition sources can be reduced when forming an organic layer (for example, a light emitting layer) to be formed.

[Fourth Embodiment]
(Material for organic EL elements)
The material for an organic EL element of this embodiment is the first compound (compound represented by the general formula (1)), the second compound, and the delayed fluorescent tertiary compound in the first embodiment or the second embodiment. At least include.
Further, the material for an organic EL device of the present embodiment may further contain a fourth compound having fluorescence emission in the second embodiment.
According to the material for an organic EL element of the present embodiment, the performance of the organic EL element can be improved (particularly, the life of the organic EL element can be extended).
The material for the organic EL device of this embodiment may further contain other compounds. When the material for an organic EL device of this embodiment further contains other compounds, the other compounds may be solid or liquid.

[Fifth Embodiment]
(Electronics)
The electronic device according to this embodiment is equipped with an organic EL element according to any one of the above-described embodiments. Examples of electronic devices include display devices and light emitting devices. Examples of the display device include display parts (for example, an organic EL panel module, etc.), a television, a mobile phone, a tablet, a personal computer, and the like. Examples of the light emitting device include lighting and vehicle lighting equipment.

[Other explanations]

In the present specification, the numerical range represented by using "-" means a range including a numerical value before "-" as a lower limit value and a numerical value after "-" as an upper limit value. do.

In the present specification, when 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 contained in Rx (carbon atom). , Nitrogen atom, oxygen atom, sulfur atom or silicon atom) and the atom contained in Ry (carbon atom, nitrogen atom, oxygen atom, sulfur atom or silicon atom) are single-bonded, double-bonded, triple-bonded, or It means that they are bonded via a divalent linking group to form a ring having 5 or more ring-forming atoms (specifically, a heterocycle 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.
The divalent linking group is not particularly limited, but for example, -O-, -CO-, -CO _2- , -S-, -SO-, -SO _2- , -NH-, -NRa-, and these. Examples thereof include a group in which two or more linking groups of the above are combined.
Specific examples of the heterocycle include a ring structure (heterocycle) obtained by removing the bond from the "heteroaryl group Sub ₂ " exemplified in "Explanation of each substituent in the general formula" described later. These heterocycles may have substituents.
As a specific example of the aromatic hydrocarbon ring, a ring structure (aromatic hydrocarbon ring) obtained by removing the bond from the "aryl group Sub ₁ " exemplified in "Explanation of each substituent in the general formula" described later is used. Can be mentioned. These aromatic hydrocarbon rings may have a substituent.
Examples of Ra include the substituted or unsubstituted alkyl group Sub ₃ having 1 to 30 carbon atoms exemplified in "Explanation of each substituent in the general formula" described later, and the substituted or unsubstituted ring-forming carbon number 6 to 3. Examples thereof include an aryl group Sub ₁ of 30 and a heteroaryl group Sub ₂ having 5 to 30 substituted or unsubstituted ring-forming atoms.
For example, when Rx and Ry are bonded to each other to form a ring, in the molecular structure represented by the following general formula (E1), the atom contained in Rx ₁ and the atom contained in Ry ₁ are represented by the general formula (E1). Forming the ring (ring structure) E represented by E2); In the molecular structure represented by the general formula (F1), the atom contained in Rx ₁ and the atom contained in Ry ₁ are represented by the general formula (F1). Forming the ring F represented by F2); In the molecular structure represented by the general formula (G1), the atom contained in Rx ₁ and the atom contained in Ry ₁ are represented by the general formula (G2). To form the ring G to be formed; in the molecular structure represented by the general formula (H1), the atom contained in Rx ₁ and the atom contained in Ry ₁ are represented by the general formula (H2). In the molecular structure represented by the general formula (I1), the atom contained in Rx ₁ and the atom contained in Ry ₁ form a ring I represented by the general formula (I2). Means;
In the general formulas (E1) to (I1), * independently represents a bond position with another atom in one molecule. The two * in the general formula (E1) correspond to the two * in the general formula (E2), respectively, and the two * in the general formula (F1) correspond to the two * in the general formula (F2), respectively. Then, the two * in the general formula (G1) correspond to the two * in the general formula (G2), respectively, and the two * in the general formula (H1) correspond to the two * in the general formula (H2). Corresponding to each, the two * in the general formula (I1) correspond to the two * in the general formula (I2), respectively.

In the molecular structure 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), * independently represents a bond position with another atom in one molecule. The two * in the general formula (E2) correspond to the two * in the general formula (E1), respectively. Similarly, the two * in the general formulas (F2) to (I2) correspond to the two * in the general formulas (F1) to (I1), respectively.

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

As used herein, the number of ring-forming carbon atoms constitutes the ring itself of a compound having a structure in which atoms are cyclically bonded (for example, a monocyclic compound, a fused ring compound, a crosslinked compound, a carbocyclic compound, or a heterocyclic compound). Represents the number of carbon atoms in an atom. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of carbons forming the ring. The "ring-forming carbon number" described below shall be the same unless otherwise specified. For example, the benzene ring has 6 ring-forming carbon atoms, the naphthalene ring has 10 ring-forming carbon atoms, the pyridinyl group has 5 ring-forming carbon atoms, and the furanyl group has 4 ring-forming carbon atoms. When, for example, an alkyl group is substituted as a substituent on the benzene ring or naphthalene ring, the number of carbon atoms of the alkyl group is not included in the number of ring-forming carbon atoms. When, for example, a fluorene ring is bonded to the fluorene ring as a substituent (including a spirofluorene ring), the number of carbon atoms of the fluorene ring as a substituent is not included in the number of ring-forming carbon atoms.

In the present specification, the number of ring-forming atoms is a compound having a structure in which atoms are cyclically bonded (for example, a monocycle, a fused ring, or a ring assembly) (for example, a monocyclic compound, a fused ring compound, a crosslinked compound, a carbocyclic compound, or a complex). It represents the number of atoms constituting the ring itself of the ring compound). Atoms that do not form a ring and atoms contained in the 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 shall be the same unless otherwise specified. For example, the pyridine ring has 6 ring-forming atoms, the quinazoline ring has 10 ring-forming atoms, and the furan ring has 5 ring-forming atoms. Hydrogen atoms bonded to carbon atoms of the pyridine ring and the quinazoline ring and atoms constituting the substituent are not included in the number of ring-forming atoms. 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.

-Explanation of each substituent in the general formula in the present specification (description of each substituent).
The aryl group (sometimes referred to as an aromatic hydrocarbon group) in the present specification is, for example, the aryl group Sub ₁ . The aryl group Sub ₁ preferably has a ring-forming carbon number of 6 to 30, more preferably 6 to 20, further preferably 6 to 14, and more preferably 6 to 12. More preferred.
The aryl group Sub ₁ in the present specification is, for example, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a fluorenyl group, a pyrenyl group, a chrysenyl group, a fluoranthenyl group, a benzo [a] anthryl. At least one selected from the group consisting of a group, a benzo [c] phenanthryl group, a triphenylenyl group, a benzo [k] fluoranthenyl group, a benzo [g] chrysenyl group, a benzo [b] triphenylenyl group, a pisenyl group, and a perylenyl group. It is the basis of that.

Among the aryl groups Sub ₁ , phenyl group, biphenyl group, naphthyl group, phenanthryl group, terphenyl group and fluorenyl group are preferable. For the 1-fluorenyl group, 2-fluorenyl group, 3-fluorenyl group and 4-fluorenyl group, the carbon atom at the 9-position is substituted or unsubstituted alkyl group Sub ₃ described later in the present specification, or substituted or unsubstituted. It is preferable that the aryl group Sub ₁ of the above is substituted.

The heteroaryl group (sometimes referred to as a heterocyclic group, a heteroaromatic ring group, or an aromatic heterocyclic group) in the present specification is, for example, the heterocyclic group Sub ₂ . The heterocyclic group Sub ₂ is a group containing at least one atom selected from the group consisting of nitrogen, sulfur, oxygen, silicon, selenium atom, and germanium atom as a heteroatom. The heterocyclic group Sub ₂ is preferably a group containing at least one atom selected from the group consisting of nitrogen, sulfur, and oxygen as a heteroatom. As the heterocyclic group Sub ₂ , the number of ring-forming atoms is preferably 5 to 30, more preferably 5 to 20, and even more preferably 5 to 14.

The heterocyclic group Sub ₂ in the present specification is, for example, a pyridyl group, a pyrimidinyl group, a pyrazinyl group, a pyridadinyl group, a triazinyl group, a quinolyl group, an isoquinolinyl group, a naphthyldinyl group, a phthalazinyl group, a quinoxalinyl group, a quinazolinyl group and a phenanthridinyl. Group, acridinyl group, phenanthrolinyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, indrill group, benzimidazolyl group, indazolyl group, imidazolypyridinyl group, benztriazolyl group, carbazolyl group. , Frill group, thienyl group, oxazolyl group, thiazolyl group, isoxazolyl group, isothiazolyl group, oxadiazolyl group, thiadiazolyl group, benzofuranyl group, benzothienyl group, benzoxazolyl group, benzothiazolyl group, benzoisoxazolyl group, benzoisoti A group consisting of an azolyl group, a benzoxaziazolyl group, a benzothiadiazolyl group, a dibenzofuranyl group, a dibenzothienyl group, a piperidinyl group, a pyrrolidinyl group, a piperazinyl group, a morphoryl group, a phenazinyl group, a phenothiazinyl group, and a phenoxadinyl group. At least one of the groups selected from.

Among the above heterocyclic groups Sub ₂ , 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofranyl group, 1-dibenzothienyl group, 2-dibenzothienyl group, 3- Even more preferred are a dibenzothienyl group, a 4-dibenzothienyl group, a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, and a 9-carbazolyl group. For the 1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group and 4-carbazolyl group, the nitrogen atom at the 9-position is substituted or unsubstituted aryl group Sub ₁ in the present specification, or a substituted or unsubstituted complex. It is preferable that the ring group Sub ₂ is substituted.

Further, in the present specification, the heterocyclic group Sub ₂ 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), XX and YA are independently heteroatoms, and are oxygen atoms, sulfur atoms, selenium atoms, silicon atoms, or germanium atoms. Is preferable. The partial structures represented by the general formulas (XY-1) to (XY-18) have a bond at an arbitrary position to form a heterocyclic group, and this heterocyclic group has a substituent. May be good.

Further, in the present specification, the heterocyclic group Sub ₂ may be, for example, a group represented by the following general formulas (XY-19) to (XY-22). In addition, the position of the bond can be changed as appropriate.

The alkyl group in the present specification may be either a linear alkyl group, a branched chain alkyl group or a cyclic alkyl group.
The alkyl group herein is, for example, the alkyl group Sub ₃ .
The linear alkyl group herein is, for example, the linear alkyl group Sub ₃₁ .
The alkyl group of the branched chain in the present specification is, for example, the alkyl group Sub ₃₂ of the branched chain.
The cyclic alkyl group in the present specification is, for example, a cyclic alkyl group Sub ₃₃ (also referred to as a cycloalkyl group Sub ₃₃ ).
The alkyl group Sub ₃ is, for example, at least one group selected from the group consisting of a linear alkyl group Sub ₃₁ , a branched chain alkyl group Sub ₃₂ , and a cyclic alkyl group Sub ₃₃ .
The linear alkyl group Sub ₃₁ or the branched chain alkyl group Sub ₃₂ in the present specification preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and more preferably 1 to 10 carbon atoms. More preferably, it is even more preferably 1 to 6.
The ring-forming carbon number of the cycloalkyl group Sub ₃₃ in the present specification is preferably 3 to 30, more preferably 3 to 20, further preferably 3 to 10, and 5 to 8. Is even more preferable.

The linear alkyl group Sub ₃₁ or the branched alkyl group Sub ₃₂ in the present specification is, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, and the like. 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 It is at least one group selected from the group consisting of a group, a 1-butylpentyl group, a 1-heptyloctyl group, and a 3-methylpentyl group.

The linear alkyl group Sub ₃₁ or the branched alkyl group Sub ₃₂ includes a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, and n. -Pentyl groups, n-hexyl groups, amyl groups, isoamyl groups, and neopentyl groups are even more preferred.

As used herein, the cycloalkyl group Sub ₃₃ is, for example, at least one group selected from the group consisting of a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 4-methylcyclohexyl group, an adamantyl group, and a norbornyl group. Is. Among the cycloalkyl groups Sub ₃₃ , cyclopentyl groups and cyclohexyl groups are even more preferable.

The alkyl halide group in the present specification is, for example, the alkyl halide group Sub ₄ , and the alkyl halide group Sub ₄ is, for example, the alkyl group Sub ₃ substituted with one or more halogen atoms, preferably a fluorine atom. It is an alkyl group.

The alkyl halide group Sub ₄ in the present specification is, for example, a group consisting of a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a fluoroethyl group, a trifluoromethylmethyl group, a trifluoroethyl group, and a pentafluoroethyl group. At least one of the groups selected from.

The substituted silyl group in the present specification is, for example, the substituted silyl group Sub ₅ , and the substituted silyl group Sub ₅ is at least one selected from the group consisting of, for example, an alkylsilyl group Sub ₅₁ and an arylsilyl group Sub ₅₂ . It is the basis.

The alkylsilyl group Sub ₅₁ in the present specification is, for example, the trialkylsilyl group Sub ₅₁₁ having the above-mentioned alkyl group Sub ₃ .
The trialkylsilyl group Sub ₅₁₁ is, for example, a trimethylsilyl group, a triethylsilyl group, a tri-n-butylsilyl group, a tri-n-octylsilyl group, a triisobutylsilyl group, a dimethylethylsilyl group, a dimethylisopropylsilyl group, a dimethyl-n. -At least one selected from the group consisting of a propylsilyl group, a dimethyl-n-butylsilyl group, a dimethyl-t-butylsilyl group, a diethylisopropylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, and a triisopropylsilyl group. It is the basis. The three alkyl groups Sub ₃ in the trialkylsilyl group Sub ₅₁₁ may be the same or different from each other.

The arylsilyl group Sub ₅₂ in the present specification is, for example, at least one group selected from the group consisting of the dialkylarylsilyl group Sub ₅₂₁ , the alkyldiarylsilyl group Sub ₅₂₂ , and the triarylsilyl group Sub ₅₂₃ .

The dialkylarylsilyl group Sub ₅₂₁ is, for example, a dialkylarylsilyl group having two alkyl groups Sub ₃ and one aryl group Sub ₁ . The number of carbon atoms of the dialkylarylsilyl group Sub ₅₂₁ is preferably 8 to 30.

The alkyldiarylsilyl group Sub ₅₂₂ is, for example, an alkyldiarylsilyl group having one alkyl group Sub ₃ and two aryl diaryl silyl groups Sub ₁ . The alkyldiarylsilyl group Sub ₅₂₂ preferably has 13 to 30 carbon atoms.

The triarylsilyl group Sub ₅₂₃ is, for example, a triarylsilyl group having three of the above aryl groups Sub ₁ . The triarylsilyl group Sub ₅₂₃ preferably has 18 to 30 carbon atoms.

The substituted or unsubstituted alkylsulfonyl group in the present specification is, for example, the alkylsulfonyl group Sub ₆ , and the alkylsulfonyl group Sub ₆ is represented by —SO ₂ R _w . -R _w in SO ₂ R _w represents the above-mentioned alkyl group Sub ₃ substituted or unsubstituted.

The aralkyl group (sometimes referred to as an arylalkyl group) in the present specification is, for example, the aralkyl group Sub ₇ . The aryl group in the aralkyl group Sub ₇ includes, for example, at least one of the above aryl group Sub ₁ and the above heteroaryl group Sub ₂ .

The aralkyl group Sub ₇ in the present specification is preferably a group having an aryl group Sub ₁ , and is represented as _{−Z3 -} Z4. The Z ₃ is, for example, an alkylene group corresponding to the above-mentioned alkyl group Sub ₃ . The Z ₄ is, for example, the aryl group Sub ₁ . In this aralkyl group Sub ₇ , 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 1 to 1). 10, more preferably 1 to 6). The aralkyl group Sub ₇ is, for example, a benzyl group, a 2-phenylpropane-2-yl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a 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 -At least one group selected from the group consisting of a naphthylethyl group, a 2-β-naphthylethyl group, a 1-β-naphthylisopropyl group, and a 2-β-naphthylisopropyl group.

The alkoxy group in the present specification is, for example, the alkoxy group Sub ₈ , and the alkoxy group Sub ₈ is represented as −OZ ₁ . This Z ₁ is, for example, the above-mentioned alkyl group Sub ₃ . The alkoxy group Sub ₈ preferably has 1 to 30 carbon atoms, and more preferably 1 to 20 carbon atoms. The alkoxy group Sub ₈ is, for example, at least one group selected from the group consisting of a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, and a hexyloxy group.

The halogenated alkoxy group in the present specification is, for example, a halogenated alkoxy group Sub ₉ , and in the halogenated alkoxy group Sub ₉ , for example, the alkoxy group Sub ₈ is substituted with one or more halogen atoms, preferably a fluorine atom. It is an alkoxy group.

The aryloxy group (sometimes referred to as an arylalkoxy group) in the present specification is, for example, the arylalkoxy group Sub ₁₀ . The aryl group in the arylalkoxy group Sub ₁₀ contains at least one of the aryl group Sub ₁ and the heteroaryl group Sub ₂ .

The arylalkoxy group Sub ₁₀ in the present specification is represented as —OZ ₂ . The Z ₂ is, for example, an aryl group Sub ₁ or a heteroaryl group Sub ₂ . The ring-forming carbon number of the arylalkoxy group Sub ₁₀ is preferably 6 to 30, and more preferably 6 to 20. Examples of the arylalkoxy group Sub ₁₀ include a phenoxy group.

The substituted amino group in the present specification is, for example, the substituted amino group Sub ₁₁ , and the substituted amino group Sub ₁₁ is at least one selected from the group consisting of, for example, the arylamino group Sub ₁₁₁ and the alkylamino group Sub ₁₁₂ . It is a group.
The arylamino group Sub ₁₁₁ is represented as -NHR _V1 or -N (R _V1 ) ₂ . This _RV1 is, for example, _an aryl group Sub1. -The two R _V1s in N (R _V1 ) ₂ are the same or different.
The alkylamino group Sub ₁₁₂ is represented as -NHR _V2 , or -N (R _V2 ) ₂ . This R _V2 is, for example, an alkyl group Sub ₃ . -The two R _V2s in N (R _V2 ) ₂ are the same or different.

The alkenyl group herein is, for example, the alkenyl group Sub ₁₂ , and the alkenyl group Sub ₁₂ is either linear or branched, eg, vinyl group, propenyl group, butenyl group, oleyl group, eikosa. At least one selected from the group consisting of a pentaenyl group, a docosahexaenyl group, a styryl group, a 2,2-diphenylvinyl group, a 1,2,2-triphenylvinyl group, and a 2-phenyl-2-propenyl. It is a group.

The alkynyl group in the present specification is, for example, the alkynyl group Sub ₁₃ , and the alkynyl group Sub ₁₃ may be either a straight chain or a branched chain, for example, a group consisting of ethynyl, propynyl, and 2-phenylethynyl. At least one of the groups selected from.

The alkylthio group in the present specification is, for example, the alkylthio group Sub ₁₄ .
The alkylthio group Sub ₁₄ is represented as -SR _V3 . This _RV3 is, for example, an alkyl group Sub ₃ . The number of carbon atoms of the alkylthio group Sub ₁₄ is preferably 1 to 30, and more preferably 1 to 20.
The arylthio group in the present specification is, for example, the arylthio group Sub ₁₅ .
The arylthio group Sub ₁₅ is represented as -SR _V4 . This _RV4 is, for example, the aryl group Sub ₁ . The ring-forming carbon number of the arylthio group Sub ₁₅ is preferably 6 to 30, and more preferably 6 to 20.

Examples of the halogen atom in the present specification include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like, and a fluorine atom is preferable.

The substituted phosphino group in the present specification is, for example, the substituted phosphino group Sub ₁₆ , and the substituted phosphino group Sub ₁₆ is, for example, a phenylphosphanyl group.

The arylcarbonyl group in the present specification is, for example, the arylcarbonyl group Sub ₁₇ , and the arylcarbonyl group Sub ₁₇ is represented as -COY'. This Y'is, for example, the aryl group Sub ₁ . The arylcarbonyl group Sub ₁₇ herein is, for example, at least one group selected from the group consisting of a phenylcarbonyl group, a diphenylcarbonyl group, a naphthylcarbonyl group, and a triphenylcarbonyl group.

The acyl group herein is, for example, the acyl group Sub ₁₈ and the acyl group Sub ₁₈ is represented as −COR'. This R'is, for example, the alkyl group Sub ₃ . As used herein, the acyl group Sub ₁₈ is, for example, at least one group selected from the group consisting of an acetyl group and a propionyl group.

The substituted phosphoryl group in the present specification is, for example, the substituted phosphoryl group Sub ₁₉ , and the substituted phosphoryl group Sub ₁₉ is represented by the following general formula (P).

In the general formula (P), Ar _P1 and Ar _P2 are any of the substituents selected from the group consisting of the alkyl group Sub ₃ and the aryl group Sub ₁ .

The ester group in the present specification is, for example, the ester group Sub ₂₀ , and the ester group Sub ₂₀ is, for example, at least one group selected from the group consisting of an alkyl ester group and an aryl ester group.
The alkyl ester group in the present specification is, for example, the alkyl ester group Sub ₂₀₁ , and the alkyl ester group Sub ₂₀₁ is represented by −C (= O) ^ORE . ^RE is, for example, the above-mentioned alkyl group Sub ₃ substituted or unsubstituted.
The aryl ester group in the present specification is, for example, the aryl ester group Sub ₂₀₂ , and the aryl ester group Sub ₂₀₂ is represented by −C (= O) OR ^Ar . R ^Ar is, for example, the above-mentioned aryl group Sub ₁ substituted or unsubstituted.

The siroxanyl group in the present specification is, for example, the siroxanyl group Sub ₂₁ and the siroxanyl group Sub ₂₁ is a silicon compound group via an ether bond. The siroxanyl group Sub ₂₁ is, for example, a trimethylsiloxanil group.

The carbamoyl group herein is represented by -CONH ₂ .
The substituted carbamoyl group herein is, for example, the carbamoyl group Sub ₂₂ and the carbamoyl group Sub ₂₂ is represented by -CONH-Ar ^C or -CONH- ^RC . Ar ^C is selected from the group consisting of, for example, the substituted or unsubstituted aryl group Sub ₁ (preferably having 6 to 10 ring-forming carbon atoms) and the heteroaryl group Sub ₂ (preferably having 5 to 14 ring-forming atoms). Is at least one of the groups to be. Ar ^C may be a group in which an aryl group Sub ₁ and a heteroaryl group Sub ₂ are bonded.
The ^RC is, for example, the substituted or unsubstituted alkyl group Sub ₃ (preferably 1 to 6 carbon atoms).

As used herein, the term "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 heteroatom constituting a heterocycle (including a saturated ring, an unsaturated ring, and an aromatic ring).

Further, in the present specification, the hydrogen atom includes isotopes having different numbers of neutrons, that is, light hydrogen (Protium), deuterium (Deuterium), and triple hydrogen (Tritium).
In the present specification, a hydrogen atom, that is, a light hydrogen atom, a heavy hydrogen atom, or a hydrogen atom is located at a bondable position in which a symbol such as "R" or "D" representing a deuterium atom is not specified in the chemical structural formula. It is assumed that the triple hydrogen atom is bonded.

Hereinafter, the alkyl group Sub ₃ is any one or more of the linear alkyl group Sub ₃₁ described in "Explanation of each substituent", the branched alkyl group Sub ₃₂ , and the cyclic alkyl group Sub ₃₃ . means.
Similarly, the substituted silyl group Sub ₅ means any one or more of the alkylsilyl group Sub ₅₁ and the arylsilyl group Sub ₅₂ .
Similarly, the substituted amino group Sub ₁₁ means any one or more of the arylamino group Sub ₁₁₁ and the alkylamino group Sub ₁₁₂ .

In the present specification, the substituent in the case of "substituted or unsubstituted" is, for example, the substituent _RF1 , and the substituent _RF1 is an aryl group Sub ₁ , a heteroaryl group Sub ₂ , an alkyl group Sub ₃ , and the like. Alkyl halide group Sub ₄ , substituted silyl group Sub ₅ , alkylsulfonyl group Sub ₆ , aralkyl group Sub ₇ , alkoxy group Sub ₈ , halogenated alkoxy group Sub ₉ , arylalkoxy group Sub ₁₀ , substituted amino group Sub ₁₁ , alkenyl group. Sub ₁₂ , alkynyl group Sub ₁₃ , alkylthio group Sub ₁₄ , arylthio group Sub ₁₅ , substituted phosphino group Sub ₁₆ , arylcarbonyl group Sub ₁₇ , acyl group Sub ₁₈ , substituted phosphoryl group Sub ₁₉ , ester group Sub ₂₀ , ester group Sub ₂₁ , Carbamoyl group Sub ₂₂ , an unsubstituted amino group, an unsubstituted silyl group, a halogen atom, a cyano group, a hydroxy group, a nitro group, and a carboxy group.

In the present specification, the substituent RF1 in the case of "substituted or unsubstituted" may be a _diarylboron group (Ar _B1 Ar _B2 B-). Examples of the Ar _B1 and Ar _B2 include the above-mentioned aryl group Sub ₁ . Ar _B1 and Ar _B2 in Ar _B1 Ar _B2 B- are the same or different.

Specific examples of the substituent _RF1 and preferable groups include substituents (for example, aryl group Sub ₁ , heteroaryl group Sub ₂ , alkyl group Sub ₃ , halogenated alkyl group Sub ₄ ) in “Explanation of each substituent”. Substituted silyl group Sub ₅ , alkylsulfonyl group Sub ₆ , aralkyl group Sub ₇ , alkoxy group Sub ₈ , halogenated alkoxy group Sub ₉ , arylalkoxy group Sub ₁₀ , substituted amino group Sub ₁₁ , alkenyl group Sub ₁₂ , alkynyl group Sub ₁₃ , Alkylthio group Sub ₁₄ , arylthio group Sub ₁₅ , substituted phosphino group Sub ₁₆ , arylcarbonyl group Sub ₁₇ , acyl group Sub ₁₈ , substituted phosphoryl group Sub ₁₉ , ester group Sub ₂₀ , and _siroxanyl group Sub ₂₁ ). Specific examples of the above and groups similar to the preferred groups are mentioned.

The substituent RF1 in the case of "substituted or _{unsubstituted} " is an aryl group Sub ₁ , a heteroaryl group Sub ₂ , an alkyl group Sub ₃ , a halide alkyl group Sub ₄ , a substituted silyl group Sub ₅ , an alkylsulfonyl group Sub ₆ , Aralkyl group Sub ₇ , alkoxy group Sub ₈ , halogenated alkoxy group Sub ₉ , arylalkoxy group Sub ₁₀ , substituted amino group Sub ₁₁ , alkenyl group Sub ₁₂ , alkynyl group Sub ₁₃ , alkylthio group Sub ₁₄ , arylthio group Sub ₁₅ , Substituent phosphino group Sub ₁₆ , arylcarbonyl group Sub ₁₇ , acyl group Sub ₁₈ , substituted phosphoryl group Sub ₁₉ , ester group Sub ₂₀ , siroxanyl group Sub ₂₁ , carbamoyl group Sub ₂₂ , unsubstituted amino group, unsubstituted silyl group, It may be further substituted with at least one group selected from the group consisting of a halogen atom, a cyano group, a hydroxy group, a nitro group, and a carboxy group (hereinafter, also referred to as a substituent _RF2 ). Further, a plurality of these substituents _RF2 may be bonded to each other to form a ring.

In the case of "substituted or unsubstituted", "unsubstituted" means that the substituent _RF1 is not substituted and a hydrogen atom is bonded.

In the present specification, the "carbon number XX to YY" in the expression "ZZ group of substituted or unsubstituted carbon number XX to YY" represents the carbon number when the ZZ group is unsubstituted and is substituted. If so, the carbon number of the substituent _RF1 is not included.

In the present specification, "the number of atoms XX to YY" in the expression "the ZZ group having the number of atoms XX to YY substituted or unsubstituted" represents the number of atoms when the ZZ group is unsubstituted and is substituted. The number of atoms of the substituent _RF1 in the case is not included.

The same applies to the case of "substitutable or unsubstituted" in the compound described in the present specification or its partial structure.

In the present specification, when substituents are bonded to each other to construct a ring, the structure of the ring is a saturated ring, an unsaturated ring, an aromatic hydrocarbon ring, or a heterocycle.

In the present specification, examples of the aromatic hydrocarbon group in the linking group include a divalent or higher valent group obtained by removing one or more atoms from the monovalent aryl group Sub ₁ described above.
In the present specification, examples of the heterocyclic group in the linking group include a divalent or higher valent group obtained by removing one or more atoms from the monovalent heteroaryl group Sub ₂ described above.

[Modification of the embodiment]
The present invention is not limited to the above-described embodiment, and changes, improvements, and the like to the extent that the object of the present invention can be achieved are included in the present invention.

For example, the light emitting layer is not limited to one layer, and a plurality of light emitting layers may be laminated. When the organic EL element has a plurality of light emitting layers, it is sufficient that at least one light emitting layer satisfies the conditions described in the above embodiment. For example, the other light emitting layer may be a fluorescent light emitting layer or a phosphorescent light emitting layer utilizing light emission by electron transition from the triplet excited state to the direct ground state.
Further, when the organic EL element has a plurality of light emitting layers, these light emitting layers may be provided adjacent to each other, or a so-called tandem type organic in which a plurality of light emitting units are laminated via an intermediate layer. It may be an EL element.

Further, for example, a barrier layer may be provided adjacent to at least one of the anode side and the cathode side of the light emitting layer. The barrier layer is preferably placed in contact with the light emitting layer to block at least one of holes, electrons, and excitons.
For example, when the barrier layer is arranged in contact with the cathode side of the light emitting layer, the barrier layer transports electrons and holes reach the layer on the cathode side of the barrier layer (for example, the electron transport layer). Stop doing. When the organic EL element includes an electron transport layer, it is preferable to include the barrier layer between the light emitting layer and the electron transport layer.
When the barrier layer is arranged in contact with the anode side of the light emitting layer, the barrier layer transports holes and electrons are transferred to the layer on the anode side of the barrier layer (for example, the hole transport layer). Prevent it from reaching. When the organic EL element includes a hole transport layer, it is preferable to include the barrier layer between the light emitting layer and the hole transport layer.
Further, a barrier layer may be provided adjacent to the light emitting layer so that the excitation energy does not leak from the light emitting layer to the peripheral layer thereof. It prevents excitons generated in the light emitting layer from moving to a layer on the electrode side of the barrier layer (for example, an electron transport layer and a hole transport layer).
It is preferable that the light emitting layer and the barrier layer are joined.

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

Hereinafter, examples according to the present invention will be described. The present invention is not limited to these examples.

<Compound>
The first compound represented by the general formula (1) used in the production of the organic EL device of Examples 1 to 7 is shown below.

The second compounds used in the production of the organic EL devices of Examples 1 to 7 are shown below.

The compounds corresponding to the first compound or the second compound used in the production of the organic EL devices of Comparative Examples 1 to 3 are shown below.

The structures of the other compounds used in the production of the organic EL devices of Examples 1 to 7 and Comparative Examples 1 to 3 are shown below.

<Manufacturing of organic EL element>
An organic EL device was prepared and evaluated as follows.

(Example 1)
A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) having a thickness of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 1 minute. The film thickness of ITO was 130 nm.
The glass substrate with the transparent electrode line after cleaning is mounted on the substrate holder of the vacuum vapor deposition apparatus, and first, the compound HT1 and the compound HA are coexisted so as to cover the transparent electrode on the surface on the side where the transparent electrode line is formed. The vapor deposition was performed to form a hole injection layer having a film thickness of 10 nm. The concentration of compound HT1 in the hole injection layer was 97% by mass, and the concentration of compound HA was 3% by mass.
Next, the compound HT1 was deposited on the hole injection layer to form a first hole transport layer having a film thickness of 110 nm.
Next, the compound HT2 was deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 5 nm.
Next, the compound p2 was deposited on the second hole transport layer to form an electron barrier layer having a film thickness of 5 nm.
Next, the compound tp1 as the first compound, the compound n1 as the second compound, and the compound TADF as the third compound are co-deposited on the electron barrier layer to form a light emitting layer having a film thickness of 25 nm. did. The concentration of compound tp1 in the light emitting layer was 25% by mass, the concentration of compound n1 was 25% by mass, and the concentration of compound TADF was 50% by mass.
Next, the compound HBL was deposited on the light emitting layer to form a hole barrier layer having a film thickness of 5 nm.
Next, the compound ET was deposited on the hole barrier layer to form an electron transport layer having a film thickness of 50 nm.
Next, lithium fluoride (LiF) was vapor-deposited on the electron transport layer to form an electron-injectable electrode (cathode) having a film thickness of 1 nm.
Then, metallic aluminum (Al) was deposited on the electron-injectable electrode to form a metallic Al cathode having a film thickness of 80 nm.
The element configuration of the organic EL element according to the first embodiment is schematically as follows.
ITO (130) / HT1: HA (10,97%: 3%) / HT1 (110) / HT2 (5) / p2 (5) / tp1: n1: TADF (25,25%: 25%: 50%) / HBL (5) / ET (50) / LiF (1) / Al (80)
The numbers in parentheses indicate the film thickness (unit: nm).
Also in parentheses, the percentage displayed number (97%: 3%) indicates the ratio (mass%) of compound HT1 and compound HA in the hole injection layer, and the percentage displayed number (25%: 25%:). 50%) indicates the ratio (% by mass) of the compound tp1, the compound n1 and the compound TADF in the light emitting layer. Hereinafter, the same notation will be used.

(Examples 2 to 7)
The organic EL devices from Example 2 to Example 7 were produced in the same manner as in Example 1 except that the light emitting layer in Example 1 was replaced with the light emitting layer shown in Table 1.

(Comparative Examples 1 to 3)
The organic EL devices from Comparative Example 1 to Comparative Example 3 were produced in the same manner as in Example 1 except that the light emitting layer in Example 1 was replaced with the light emitting layer shown in Table 1.

<Evaluation of organic EL element>
The organic EL devices produced in Examples 1 to 7 and Comparative Examples 1 to 3 were evaluated as follows. The results are shown in Table 1. The compounds p1 and Ref-p1 used in Comparative Examples 1 to 3 do not correspond to the general formula of the first compound, but are described in the same column as the first compound for convenience.

・ Main peak wavelength (λp)
The spectral radiance spectrum when a voltage was applied to the element so that the current density of the organic EL element was 10 mA / cm ² was measured with a spectral radiance meter CS-2000 (manufactured by Konica Minolta Co., Ltd.). From the obtained spectral radiance spectrum, the main peak wavelength λp (unit: nm) was determined.

・ Life LT95
A voltage was applied to the obtained organic EL element so that the current density was 50 mA / cm ² , and the time until the brightness became 95% with respect to the initial brightness (LT95 (unit: time)) was measured.
The "LT95 (relative value)" (unit:%) was calculated by the measured value of LT95 in each example and the following mathematical formula (Equation 1X).
LT95 (relative value) = (LT95 of each example / LT95 of Comparative Example 1) × 100 ... (Equation 1X)

The organic EL elements of Examples 1 to 7 had a longer life than the organic EL elements of Comparative Examples 1 to 3. For example, by comparing Comparative Example 1 with Examples 1, 2 and 7, it can be seen that the device life is improved by using the first compound (triphenylene compound) instead of the configuration of Patent Document 1. For example, by comparing Comparative Example 3 and Example 7, it can be seen that the device life is improved by using the first compound (triphenylene compound) having no carbonyl group instead of the configuration of Patent Document 2.

<Evaluation of compounds>
The physical characteristics of the compound were measured by the following method.

Thermally Activated Delayed Fluorescence (Delayed Fluorescence of Compound TADF)
Delayed fluorescence was confirmed by measuring transient PL using the apparatus shown in FIG. The compound TADF was dissolved in toluene to prepare a dilute solution having an absorbance of 0.05 or less at the excitation wavelength in order to remove the contribution of self-absorption. Further, in order to prevent quenching by oxygen, the sample solution was frozen and degassed and then sealed in a cell with a lid under an argon atmosphere to obtain an oxygen-free sample solution saturated with argon.
The fluorescence spectrum of the sample solution was measured with a spectrofluorometer FP-8600 (manufactured by Nippon Spectroscopy Co., Ltd.), and the fluorescence spectrum of an ethanol solution of 9,10-diphenylanthracene was measured under the same conditions. Using the fluorescence area intensities of both spectra, Morris et al. J. Phys. Chem. The total fluorescence quantum yield was calculated by the equation (1) in 80 (1976) 969.
Prompt emission (immediate emission) that is immediately observed from the excited state after being excited by pulsed light (light emitted from a pulse laser) of a wavelength absorbed by the compound TADF, and Prompt emission (immediate emission) that is immediately observed after the excitation. However, there is a Delay emission (delayed emission) that is observed thereafter. Delayed fluorescent emission in this embodiment means that the amount of Delay emission (delayed emission) is 5% or more with respect to the amount of Prompt emission (immediate emission). Specifically, when the amount of Prompt emission (immediate emission) is XP and the amount of _Delay emission (delayed emission) is _XD , the value of _XD / _XP is 0.05 or more. means.
The amount of Prompt emission and Delay emission and their ratio can be determined by the same method as described in "Nature 492, 234-238, 2012" (Reference 1). The apparatus used for calculating the amount of Prompt emission and Delay emission is not limited to the apparatus described in Reference 1 or the apparatus shown in FIG.
Regarding compound TADF, it was confirmed that the amount of Delay emission (delayed emission) was 5% or more with respect to the amount of Prompt emission (immediate emission).
Specifically, for compound _TADF , the value of _XD / XP was 0.05 or more.

・ Singlet energy S ₁
The singlet energy S1 of the compound was measured by the above _- mentioned solution method.

Energy gap T _77K at 77 [K]
The T _77K of the compound was measured by the method for measuring the energy gap T _77K described in the above-mentioned “Relationship between triplet energy and energy gap at 77 [K]”.

・ ΔST
_ΔST was calculated from the measurement result of the energy gap T _77K at 77 [K] and the measurement result of the singlet energy S1.
The ΔST of compound TADF was less than 0.01 eV.

1 ... organic EL element, 2 ... substrate, 3 ... anode, 4 ... cathode, 5 ... light emitting layer, 6 ... hole injection layer, 7 ... hole transport layer, 8 ... electron transport layer, 9 ... electron injection layer.

Claims (36)

With the anode
With the cathode
It has a light emitting layer contained between the anode and the cathode, and has.
The light emitting layer contains a first compound represented by the following general formula (1), a second compound, and a delayed fluorescent third compound.
The first compound, the second compound, and the third compound have different structures from each other.
The singlet energy S ₁ (M1) of the first compound and the singlet energy S ₁ (M3) of the third compound satisfy the relationship of the following mathematical formula (Equation 1).
The singlet energy S ₁ (M2) of the second compound and the singlet energy S ₁ (M3) of the third compound satisfy the relationship of the following mathematical formula (Equation 2).
Organic electroluminescence element.
S ₁ (M1)> S ₁ (M3) ... (Equation 1)
S ₁ (M2)> S ₁ (M3) ... (number 2)

(In the general formula (1),
R ₁₀₀ to R ₁₀₈ are independently hydrogen atoms, substituents, or pairs of R _100s , pairs of R ₁₀₀ and R ₁₀₁ , pairs of R ₁₀₁ and R ₁₀₂ , R ₁₀₂ and A set of R ₁₀₃ , a set of R ₁₀₃ and R ₁₀₄ , a set of R ₁₀₄ and R ₁₀₅ , a set of R ₁₀₅ and R ₁₀₆ , a set of R ₁₀₆ and R ₁₀₇ , a set of R ₁₀₇ and R ₁₀₈ , and a set of R ₁₀₈ and R. Any one or more pairs of ₁₀₀ pairs combine with each other to form a ring.
L ₁ is a single bond or linking group
L ₁ as a linking group is
A substituted or unsubstituted ring-forming arylene group having 6 to 25 carbon atoms,
A divalent heterocyclic group having 5 to 22 substituted or unsubstituted ring-forming atoms,
Two groups selected from the group consisting of an arylene group having 6 to 25 substituted or unsubstituted ring-forming carbon atoms and a divalent heterocyclic group having 5 to 22 substituted or unsubstituted ring-forming atoms are bonded to each other. Select from the group consisting of a divalent group to be formed, an arylene group having 6 to 25 substituted or unsubstituted ring-forming carbon atoms, and a divalent heterocyclic group having 5 to 22 substituted or unsubstituted ring-forming atoms. It is a divalent group formed by combining the three groups to be formed, and B ₁ is a hydrogen atom or a substituent.
R ₁₀₀ to R ₁₀₈ and B ₁ as substituents are independent of each other.
Halogen atom,
Cyano group,
Substituentally substituted or unsubstituted aryl groups having 6 to 50 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 50 atom-forming atoms,
Substituentally substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 30 carbon atoms,
Substituentally or unsubstituted alkynyl groups having 2 to 30 carbon atoms,
Substituentally substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
Substituentally substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms,
Substituentally substituted or unsubstituted arylphosphoryl groups having 6 to 60 carbon atoms,
Hydroxy group,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms,
-A group represented by N (R ₉₁₁ ) (R ₉₁₂ ),
Thiol group,
Substituentally substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted ring-forming aralkyl groups having 7 to 30 carbon atoms,
Substitute germanium group,
Substituted phosphine oxide group,
Nitro group,
A substituted boryl group or a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms.
p is 3, and the three _R100s are the same as or different from each other.
R ₉₁₁ and R ₉₁₂ are independent of each other.
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms.
However, the first compound represented by the general formula (1) does not have a carbonyl group in the molecule. ) In the organic electroluminescence device according to claim 1,
The light emitting layer further contains a fluorescent fourth compound.
The singlet energy S ₁ (M3) of the third compound and the singlet energy S ₁ (M4) of the fourth compound satisfy the relationship of the following mathematical formula (Equation 3).
Organic electroluminescence element.
S ₁ (M3)> S ₁ (M4) ... (Equation 3) In the organic electroluminescence device according to claim 1 or 2.
A set of R _100s , a set of R ₁₀₀ and R ₁₀₁ , a set of R ₁₀₁ and R ₁₀₂ , a set of R ₁₀₂ and R ₁₀₃ , a set of R ₁₀₃ and R ₁₀₄ , a set of R ₁₀₄ and R ₁₀₅ , R ₁₀₅ and The set of R ₁₀₆ , the set of R ₁₀₆ and R ₁₀₇ , the set of R ₁₀₇ and R ₁₀₈ , and the set of R ₁₀₈ and R ₁₀₀ do not bind to each other.
Organic electroluminescence element. The organic electroluminescence device according to any one of claims 1 to 3.
The first compound is represented by the following general formula (10).
Organic electroluminescence element.

(In the general formula (10),
R ₁₀₁ to R ₁₀₈ are independently synonymous with R ₁₀₁ to R ₁₀₈ in the general formula (1).
R ₁₀₉ to R ₁₁₁ are independently synonymous with R ₁₀₀ in the general formula (1).
L ₁ has the same meaning as L ₁ in the general formula (1).
B ₁ is synonymous with B ₁ in the general formula (1). ) The organic electroluminescence device according to any one of claims 1 to 3.
The first compound contains at least one structure represented by the following general formula (11) in the molecule.
Organic electroluminescence element.

(In the general formula (11),
Z ₁₁ to Z ₁₅ are carbon atoms that independently bond with a nitrogen atom or another atom in the molecule of the first compound. ) In the organic electroluminescence device according to claim 5.
The structure represented by the general formula (11) is a structure represented by the following general formula (12).
Organic electroluminescence element.

(In the general formula (12),
Z ₁₁ , Z ₁₃ and Z ₁₅ are carbon atoms that independently bond with other atoms in the molecule of the first compound. ) The organic electroluminescence device according to any one of claims 1 to 6.
R ₁₀₀ to R ₁₀₈ are independent of each other.
Hydrogen atom,
Cyano group,
Substituentally substituted or unsubstituted aryl groups having 6 to 50 carbon atoms,
A substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
Organic electroluminescence element. The organic electroluminescence device according to any one of claims 1 to 7.
Each of R ₁₀₀ to R ₁₀₈ is an organic electroluminescence element which is independently a hydrogen atom or an substituted or unsubstituted aryl group having 6 to 50 carbon atoms. The organic electroluminescence device according to any one of claims 1 to 8.
R ₁₀₀ to R ₁₀₈ are organic electroluminescence devices which are hydrogen atoms. The organic electroluminescence device according to any one of claims 1 to 9.
L ₁ is
Single bond,
An arylene group having 6 to 25 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 22 substituted or unsubstituted ring-forming atoms.
Organic electroluminescence element. The organic electroluminescence device according to any one of claims 1 to 10.
L ₁ is an organic electroluminescence element which is a single-bonded or substituted or unsubstituted ring-forming arylene group having 6 to 25 carbon atoms. The organic electroluminescence device according to any one of claims 1 to 11.
L ₁ is an organic electroluminescence element which is a substituted or unsubstituted phenylene group or a substituted or unsubstituted biphenylene group. The organic electroluminescence device according to any one of claims 1 to 12.
B ₁ is an organic electroluminescence device which is a substituent. The organic electroluminescence device according to any one of claims 1 to 12.
B ₁ is a substituent and L ₁ is a linking group, which is an organic electroluminescence device. The organic electroluminescence device according to any one of claims 1 to 14.
B ₁ is independent of each other
Cyano group,
Substituentally substituted or unsubstituted aryl groups having 6 to 50 carbon atoms,
A substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
Organic electroluminescence element. The organic electroluminescence device according to any one of claims 1 to 15.
B ₁ is
A cyano group or any group selected from the group consisting of the groups represented by the following general formulas (b1) to (b17).
Organic electroluminescence element.

(In the general formulas (b1) to (b17),
Ra is a hydrogen atom, a substituent, or one or more pairs of a plurality of adjacent Ra pairs in each general formula are bonded to each other to form a ring.
Multiple Ras are the same as or different from each other,
Rb ₁ is a hydrogen atom or a substituent and is
Rb ₂ and Rb ₃ are independently hydrogen atoms, substituents, or pairs of Rb ₂ and Rb ₃ bonded to each other to form a ring.
Rb ₄ is a hydrogen atom or a substituent and is
Ra, Rb ₁ , Rb ₂ , Rb ₃ and Rb ₄ as substituents are independently, respectively.
Halogen atom,
Cyano group,
Substituentally substituted or unsubstituted aryl groups having 6 to 50 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 50 atom-forming atoms,
Substituentally substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 30 carbon atoms,
Substituentally or unsubstituted alkynyl groups having 2 to 30 carbon atoms,
Substituentally substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
Substituentally substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms,
Substituentally substituted or unsubstituted arylphosphoryl groups having 6 to 60 carbon atoms,
Hydroxy group,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms,
-A group represented by N (R ₉₁₃ ) (R ₉₁₄ ),
Thiol group,
Substituentally substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted ring-forming aralkyl groups having 7 to 30 carbon atoms,
Substitute germanium group,
Substituted phosphine oxide group,
Nitro group,
A substituted boryl group or a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms.
R ₉₁₃ and R ₉₁₄ are independent of each other.
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms.
* Indicates the bonding position with _L1 . ) The organic electroluminescence device according to claim 16.
Rb ₁ , Rb ₂ , Rb ₃ and Rb ₄ are independent of each other.
Hydrogen atom,
Substituentally substituted or unsubstituted aryl groups having 6 to 50 carbon atoms,
A substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
Organic electroluminescence element. The organic electroluminescence device according to any one of claims 1 to 17.
B ₁ is
A cyano group or any group selected from the group consisting of the groups represented by the following general formulas (b1) to (b11) and (b31) to (b36).
Organic electroluminescence element.

(In the general formulas (b1) to (b11),
Ra and Rb ₁ are independently hydrogen atoms or substituents, respectively.
Multiple Ras are the same as or different from each other,
* Indicates the bonding position with _L1 . )

(In the above general formula (b31), one of Y ₁₁ to Y ₂₀ is a carbon atom bonded to L ₁ .
In the general formula (b32), one of Y ₂₁ to Y ₃₀ is a carbon atom bonded to L ₁ .
In the general formula (b33), one of Y ₃₁ to Y ₄₀ is a carbon atom bonded to L ₁ .
In the general formula (b34), one of Y ₄₁ to Y ₅₀ is a carbon atom bonded to L ₁ .
In the general formula (b35), one of Y ₅₁ to Y ₆₀ is a carbon atom bonded to L ₁ .
In the general formula (b36), one of Y ₆₁ to Y ₇₀ is a carbon atom bonded to L ₁ .
In the general formula (b31), the general formula (b32), the general formula (b33), the general formula (b34), the general formula (b35) and the general formula (b36), Y ₁₁ to which is not _a carbon atom bonded to L1. Y ₂₀ , Y ₂₁ to Y ₃₀ , Y ₃₁ to Y ₄₀ , Y ₄₁ to Y ₅₀ , Y ₅₁ to Y ₆₀ , and Y ₆₁ to Y ₇₀ are carbon atoms that independently bond with a nitrogen atom or Ra, respectively. Ra is independently a hydrogen atom or a substituent. )
(In the above (b1) to (b11) and (b31) to (b36), Ra and Rb1 as substituents are independently, _respectively .
Halogen atom,
Cyano group,
Substituentally substituted or unsubstituted aryl groups having 6 to 50 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 50 atom-forming atoms,
Substituentally substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 30 carbon atoms,
Substituentally or unsubstituted alkynyl groups having 2 to 30 carbon atoms,
Substituentally substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
Substituentally substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms,
Substituentally substituted or unsubstituted arylphosphoryl groups having 6 to 60 carbon atoms,
Hydroxy group,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms,
-A group represented by N (R ₉₁₃ ) (R ₉₁₄ ),
Thiol group,
Substituentally substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted ring-forming aralkyl groups having 7 to 30 carbon atoms,
Substitute germanium group,
Substituted phosphine oxide group,
Nitro group,
A substituted boryl group or a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms.
R ₉₁₃ and R ₉₁₄ are independent of each other.
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
It is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms. ) The organic electroluminescence device according to claim 18.
B ₁ is
A cyano group or any group selected from the group consisting of the groups represented by the general formulas (b1), (b2) and (b31) to (b36).
Organic electroluminescence element. In the organic electroluminescence device according to claim 18 or 19.
B ₁ is any group selected from the group consisting of the groups represented by the general formulas (b31) to (b36).
Organic electroluminescence element. The organic electroluminescence device according to any one of claims 16 to 20.
Ra is
Hydrogen atom,
Cyano group,
Substituentally substituted or unsubstituted aryl groups having 6 to 50 carbon atoms,
A substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
Organic electroluminescence element. The organic electroluminescence device according to any one of claims 16 to 21.
Ra is an organic electroluminescence element which is a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms. The organic electroluminescence device according to any one of claims 16 to 22.
Ra is an organic electroluminescence device that is a hydrogen atom. The organic electroluminescence device according to any one of claims 1 to 23.
When the first compound has two or more triphenylene rings, the triphenylene rings are not linked by an arylene group.
Organic electroluminescence element. The organic electroluminescence device according to any one of claims 1 to 24.
The first compound has only one triphenylene ring in the molecule.
Organic electroluminescence element. The organic electroluminescence device according to any one of claims 1 to 25.
The second compound is a compound represented by the following general formula (2).
Organic electroluminescence element.

(In the general formula (2),
X ₂₁ to X ₂₆ are independently nitrogen atoms or CR ₂₀ , but at least one of X ₂₁ to X ₂₆ is a nitrogen atom.
R ₂₀ is a hydrogen atom, a substituent, a group represented by the general formula (2A), or one or more pairs of a plurality of adjacent R _20s are one or more pairs of each other. Combine to form a ring,
R ₂₁ is a substituent and
When a plurality of R _21s are present, the plurality of R _21s are the same as or different from each other.
* Is the bond position of the 6-membered ring with the carbon atom in the general formula (2).
L ₂₁ is
Single bond,
Substituentally substituted or unsubstituted ring-forming arylene group having 6 to 22 carbon atoms, trivalent group derived from the arylene group, tetravalent group, pentavalent group or hexavalent group,
Substituentally substituted or unsubstituted ring-forming divalent heterocyclic group having 5 to 22 atoms, trivalent group, tetravalent group, pentavalent group or hexavalent group derived from the heterocyclic group, or Two groups selected from the group consisting of an arylene group having 6 to 22 substituted or unsubstituted ring-forming carbon atoms and a divalent heterocyclic group having 5 to 22 substituted or unsubstituted ring-forming atoms are bonded to each other. A divalent group formed, a trivalent group derived from the divalent group, a tetravalent group, a pentavalent group or a hexavalent group.
L ₂₂ is
Single bond,
A substituted or unsubstituted ring-forming arylene group having 6 to 22 carbon atoms,
A substituted or unsubstituted ring-forming divalent heterocyclic group having 5 to 22 atoms.
n2 is 1, 2, 3, 4 or 5
When L ₂₁ is a single bond, n2 is 1, and L ₂₂ is bonded to the carbon atom of the 6-membered ring in the general formula (2).
When there are a plurality of L _22s , the plurality of L _22s are the same or different from each other.
R ₂₀ and R ₂₁ as substituents are independent of each other.
Halogen atom,
Cyano group,
Substituentally substituted or unsubstituted aryl groups having 6 to 50 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 50 atom-forming atoms,
Substituentally substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 30 carbon atoms,
Substituentally or unsubstituted alkynyl groups having 2 to 30 carbon atoms,
Substituentally substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
Substituentally substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms,
Substituentally substituted or unsubstituted arylphosphoryl groups having 6 to 60 carbon atoms,
Hydroxy group,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms,
-A group represented by N (R ₉₂₁ ) (R ₉₂₂ ),
Thiol group,
Substituentally substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted ring-forming aralkyl groups having 7 to 30 carbon atoms,
Substitute germanium group,
Substituted phosphine oxide group,
Nitro group,
A substituted boryl group or a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms.
R ₉₂₁ and R ₉₂₂ are independent of each other.
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
It is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms. ) In the organic electroluminescence device according to claim 26,
The second compound is a compound represented by the following general formula (21) or general formula (22).
Organic electroluminescence element.

(In the general formula (21) and the general formula (22), R ₂₀₁ to R ₂₀₇ are independently synonymous with R ₂₀ in the general formula (2).) The organic electroluminescence device according to claim 27.
The second compound is an organic electroluminescence device which is a compound represented by the general formula (21). The organic electroluminescence device according to any one of claims 26 to 28.
_R20 is
Hydrogen atom,
Cyano group,
Substituentally substituted or unsubstituted aryl groups having 6 to 50 carbon atoms,
A substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms, or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
Organic electroluminescence element. The organic electroluminescence device according to any one of claims 26 to 29.
R ₂₀ is an organic electroluminescence element which is a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms. The organic electroluminescence device according to any one of claims 26 to 30.
R ₂₀ is an organic electroluminescence device which is a hydrogen atom. The organic electroluminescence device according to any one of claims 1 to 31.
The second compound is an organic electroluminescence device, which is a compound represented by the following general formula (20).

(In the general formula (20), Cz is a group represented by the following general formula (201).
M ₂₀ is
Single bond,
A substituted or unsubstituted ring-forming arylene group having 6 to 25 carbon atoms,
A divalent heterocyclic group having 5 to 22 substituted or unsubstituted ring-forming atoms,
Two groups selected from the group consisting of an arylene group having 6 to 25 substituted or unsubstituted ring-forming carbon atoms and a divalent heterocyclic group having 5 to 22 substituted or unsubstituted ring-forming atoms are bonded to each other. Select from the group consisting of a divalent group to be formed, an arylene group having 6 to 25 substituted or unsubstituted ring-forming carbon atoms, and a divalent heterocyclic group having 5 to 22 substituted or unsubstituted ring-forming atoms. It is a divalent group formed by combining the three groups to be formed.
D ₂₀ is the substituent E1 and
Substituent E1 is unsubstituted or has one or more substituents E2.
Substituent E2 is unsubstituted or has one or more substituents E3.
Substituent E3 is unsubstituted or has one or more substituents E4.
Substituents E1, substituents E2, and substituents E3 are independent of each other.
Halogen atom,
Cyano group,
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
Substituentally substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 30 carbon atoms,
Substituentally or unsubstituted alkynyl groups having 2 to 30 carbon atoms,
Substituentally substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
Substituentally substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms,
Substituentally substituted or unsubstituted arylphosphoryl groups having 6 to 60 carbon atoms,
Hydroxy group,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms,
-A group represented by N (R ₉₂₃ ) (R ₉₂₄ ),
Thiol group,
Substituentally substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted ring-forming aralkyl groups having 7 to 30 carbon atoms,
Substitute germanium group,
Substituted phosphine oxide group,
Nitro group,
A substituted boryl group or a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms.
Substituents E4 are independent of each other.
Halogen atom,
Cyano group,
An unsubstituted aryl group having 6 to 30 carbon atoms,
Heterocyclic group with 5 to 30 atoms forming an unsubstituted ring,
An unsubstituted alkyl group having 1 to 30 carbon atoms,
An unsubstituted cycloalkyl group having 3 to 30 carbon atoms,
An unsubstituted alkyl halide group having 1 to 30 carbon atoms,
An unsubstituted alkenyl group having 2 to 30 carbon atoms,
An unsubstituted alkynyl group having 2 to 30 carbon atoms,
An unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
An unsubstituted arylsilyl group having 6 to 60 carbon atoms,
An unsubstituted arylphosphoryl group having 6 to 60 carbon atoms,
Hydroxy group,
An unsubstituted alkoxy group having 1 to 30 carbon atoms,
An unsubstituted, ring-forming aryloxy group having 6 to 30 carbon atoms,
-A group represented by N (R ₉₂₅ ) (R ₉₂₆ ),
Thiol group,
An unsubstituted alkylthio group having 1 to 30 carbon atoms,
An unsubstituted ring-forming aralkyl group having 7 to 30 carbon atoms,
Substitute germanium group,
Substituted phosphine oxide group,
Nitro group,
A substituted boryl group or an unsubstituted arylthio group having 6 to 30 carbon atoms.
R ₉₂₃ and R ₉₂₄ are independent of each other.
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms.
R ₉₂₅ and R ₉₂₆ are independent of each other.
An unsubstituted aryl group having 6 to 30 carbon atoms,
Heterocyclic group with 5 to 30 atoms forming an unsubstituted ring,
An unsubstituted alkyl group having 1 to 30 carbon atoms or an unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms.
When a plurality of substituents E1 are present, the plurality of substituents E1 are the same as or different from each other.
When a plurality of substituents E2 are present, the plurality of substituents E2 are the same as or different from each other.
When a plurality of substituents E3 are present, the plurality of substituents E3 are the same as or different from each other.
When a plurality of substituents E4 are present, the plurality of substituents E4 are the same as or different from each other. )

(In the general formula (201),
Each of R _1C to R _9C is independently a hydrogen atom, a substituent, or a single bond bonded to M, or a set of R _1C and R _2C , a set of R _2C and R _3C . , R _3C and R _4C pairs, R _5C and R _6C pairs, R _6C and R _7C pairs, and one or more pairs of R _7C and R _8C combined with each other to form a ring Cx. death,
However, one of R _1C to R _9C is a single bond bonded to M ₂₀ , or any one of the carbon atoms constituting the ring Cx is bonded to M ₂₀ .
R _1C to R _9C as substituents are independent of each other.
Halogen atom,
Cyano group,
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
Substituentally substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 30 carbon atoms,
Substituentally or unsubstituted alkynyl groups having 2 to 30 carbon atoms,
Substituentally substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
Substituentally substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms,
Substituentally substituted or unsubstituted arylphosphoryl groups having 6 to 60 carbon atoms,
Hydroxy group,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms,
-A group represented by N (R ₉₂₇ ) (R ₉₂₈ ),
Thiol group,
Substituentally substituted or unsubstituted alkylthio groups having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted ring-forming aralkyl groups having 7 to 30 carbon atoms,
Substitute germanium group,
Substituted phosphine oxide group,
Nitro group,
A substituted boryl group or a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms.
R ₉₂₇ and R ₉₂₈ are independent of each other.
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
It is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms. ) The organic electroluminescence device according to any one of claims 1 to 32.
The third compound is an organic electroluminescence device which is a compound represented by the following general formula (31) or the following general formula (32).

(In the general formula (31),
n is 1, 2, 3 or 4
m is 1, 2, 3 or 4
q is 0, 1, 2, 3 or 4 and
m + n + q = 6 and
CN is a cyano group and
D ₁ is a group represented by the following general formula (3a), the following general formula (3b), or the following general formula (3c), and when there are a plurality of D ₁ , the plurality of D _1s are the same or the same. Different,
Rx is a hydrogen atom, a substituent, or adjacent pairs of Rx are bonded to each other to form a ring, and when there are a plurality of Rx, the plurality of Rx are the same or different from each other. ,
Rx as a substituent is independent of each other.
Halogen atom,
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
Substituted or unsubstituted amino groups,
Substituted or unsubstituted carbonyl group,
Substituentally substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms,
A substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms, or a substituted or unsubstituted ring-forming arylsilyl group having 6 to 60 carbon atoms.
CN, D ₁ and Rx are each bonded to a carbon atom of a 6-membered ring. )

(In the above general formula (3a), R ₁ to R ₈ are independently hydrogen atoms or substituents, or a set of R ₁ and R ₂ , a set of R ₂ and R ₃ , R. One or more pairs of ₃ and R ₄ , pairs R ₅ and R ₆ , pairs R ₆ and R ₇ , and pairs R ₇ and R ₈ combine with each other to form a ring.
R ₁ to R ₈ as substituents are independent of each other.
Halogen atom,
Substituentally substituted or unsubstituted aryl group having 6 to 30 carbon atoms,
Substituted or unsubstituted heterocyclic groups with 5 to 30 atom-forming atoms,
Substituentally substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms,
Substituentally substituted or unsubstituted alkylsilyl group having 3 to 30 carbon atoms,
Substituentally substituted or unsubstituted arylsilyl group having 6 to 60 carbon atoms,
Hydroxy group,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
Substituent or unsubstituted alkoxy halide groups having 1 to 30 carbon atoms,
Substituentally substituted or unsubstituted aryloxy groups having 6 to 30 carbon atoms,
Substituentally substituted or unsubstituted alkylamino groups having 2 to 30 carbon atoms,
Substituentally substituted or unsubstituted arylamino groups having 6 to 60 carbon atoms,
Thiol group,
A substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms, or a substituted or unsubstituted ring-forming alkylthio group having 6 to 30 carbon atoms.
* Represents the bond position of the benzene ring with the carbon atom in the general formula (31). )

(In the general formula (3b),
Each of R ₃₁ to R ₃₈ is independently a hydrogen atom or a substituent, or a set of R ₃₁ and R ₃₂ , a set of R ₃₂ and R ₃₃ , a set of R ₃₃ and R ₃₄ , and R ₃₅ . And one or more of the R ₃₆ pairs, the R ₃₆ and R ₃₇ pairs, and the R ₃₇ and R ₃₈ pairs join together to form a ring.
R ₃₁ to R ₃₈ as substituents are independently synonymous with R ₁ to R ₈ in the general formula (3a).
A represents a ring structure represented by the following general formula (311) or the following general formula (312), and this ring structure A is condensed with an adjacent ring structure at an arbitrary position.
p is 1, 2, 3 or 4
When p is 2, 3 or 4, the plurality of ring structures A are the same as or different from each other.
* Represents the bond position of the benzene ring with the carbon atom in the general formula (31). )

(In the general formula (3c),
R ₃₀₀₁ to R ₃₀₀₈ are independently hydrogen atoms or substituents, or a set of R ₃₀₀₁ and R ₃₀₀₂ , a set of R ₃₀₀₂ and R ₃₀₀₃ , a set of R ₃₀₀₃ and R ₃₀₀₄ , and R ₃₀₀₅ . And one or more of the R ₃₀₀₆ pairs, the R ₃₀₀₆ and R ₃₀₀₇ pairs, and the R ₃₀₀₇ and R ₃₀₀₈ pairs join together to form a ring.
R ₃₀₀₁ to R ₃₀₀₈ as substituents are independently synonymous with R ₁ to R ₈ as substituents in the general formula (3a).
B represents a ring structure represented by the following general formula (311) or the following general formula (312), and this ring structure B is condensed with an adjacent ring structure at an arbitrary position.
px is 1, 2, 3 or 4
When px is 2, 3 or 4, the plurality of ring structures B are the same as or different from each other.
C represents a ring structure represented by the following general formula (311) or the following general formula (312), and this ring structure C is condensed with an adjacent ring structure at an arbitrary position.
py is 1, 2, 3 or 4
When py is 2, 3 or 4, the plurality of ring structures C are the same as or different from each other.
* Represents the bond position of the benzene ring with the carbon atom in the general formula (31). )

(In the above general formula (311), whether R ₃₀₀₉ and R ₃₀₁₀ are independently hydrogen atoms, substituents, or bonded to each other with a part of an adjacent ring structure to form a ring. Alternatively, pairs of R ₃₀₀₉ and R ₃₀₁₀ combine with each other to form a ring.
In the general formula (312), X ₃₀₁ is CR ₃₀₁₁ R ₃₀₁₂ , NR ₃₀₁₃ , a sulfur atom or an oxygen atom, and R ₃₀₁₁ , R ₃₀₁₂ and R ₃₀₁₃ are independently hydrogen atoms or substitutions. It is a group _, or R ₃₀₁₁ and R ₃₀₁₂ combine with each other to form a ring.
R ₃₀₀₉ , R ₃₀₁₀ , R ₃₀₁₁ , R ₃₀₁₂ and R ₃₀₁₃ as substituents are independently synonymous with R ₁ to R ₈ as substituents in the general formula (3a). )

(In the above general formula (32), Ar ₁ is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms, substituted or unsubstituted. Alkyl group with 1 to 30 carbon atoms, substituted or unsubstituted fluoroalkyl group with 1 to 30 carbon atoms, substituted or unsubstituted ring-forming cycloalkyl group with 3 to 30 carbon atoms, substituted or unsubstituted carbon number 7 Any group selected from the group consisting of ~ 30 aralkyl groups, substituted phosphoryl groups, substituted silyl groups, cyano groups, nitro groups, carboxy groups, and groups represented by the following general formulas (1a) to (1j). And
Ar _EWG has a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms containing one or more nitrogen atoms in the ring, or a ring-forming carbon number of 6 to 30 substituted with one or more cyano groups. Aryl group of
Ar _X is independently a hydrogen atom or a substituent, and Ar _X as a substituent is an aryl group having 6 to 30 substituted or unsubstituted ring-forming carbon atoms and a substituted or unsubstituted ring-forming atom number. 5 to 30 heteroaryl groups, substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted fluoroalkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted ring-forming carbon groups having 3 to 30 carbon atoms. It is represented by a cycloalkyl group, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted phosphoryl group, a substituted silyl group, a cyano group, a nitro group, a carboxy group, and the following general formulas (1a) to (1j). Any group selected from the group consisting of groups,
When n is 0, 1, 2, 3, 4 or 5, and n is 2, 3, 4 or 5, the plurality of Ar _Xs are the same as or different from each other.
The ring (F) is a substituted or unsubstituted aromatic hydrocarbon ring or a substituted or unsubstituted heterocycle, and the ring (F) is a 5-membered ring, a 6-membered ring, or a 7-membered ring, Ar. _EWG , Ar ₁ and Ar _X are each bound to the elements constituting the ring (F) and are bonded to each other.
At least one of Ar ₁ and Ar _X is any group selected from the group consisting of the groups represented by the following general formulas (1a) to (1j). )

(In the general formulas (1a) to (1j), X1 to _X20 are independently carbon atoms ( _CRA1 ) to which _a nitrogen atom (N) or _RA1 is bonded.
_In the general formula (1b), any of _X5 to X8 is a carbon atom bonded to any of _X9 to _X12 , and any of _X9 to _X12 is any of _X5 to _X8 . It is a carbon atom that bonds to the heel.
_In the general formula (1c), any one of _X5 to X8 is a carbon atom bonded to a nitrogen atom in a ring containing A ₂ .
_In the general formula (1e), any of _X5 to _X8 and X18 is a carbon atom bonded to any of _X9 to _X12 , and any of _X9 to _X12 is _X5 to X. A carbon atom that bonds to any of ₈ and _X18 .
_In the general formula (1f), any of _X5 to _X8 and X18 is a carbon atom bonded to any of _X9 to _X12 and _X19 , and any of _X9 to _X12 and _X19 . Is a carbon atom bonded to any of _X5 to _X8 and _X18 .
In the general formula (1 g), any of _X5 to _X8 is a carbon atom bonded to any of _X9 to _X12 and _X19 , and any of _X9 to _X12 and _X19 is X. It is a carbon atom bonded to any of ₅ to _X8 , and is a carbon atom.
_In the general formula (1h), any one of _X5 to _X8 and X18 is a carbon atom bonded to a nitrogen atom in a ring containing A ₂ .
_In the general formula (1i), any one of _X5 to _X8 and _X18 is a nitrogen atom connecting a ring containing _X9 to _X12 and _X19 and a ring containing _X13 to _X16 and X20. Is a carbon atom that binds to
_In the general formula (1j), any one of _X5 to X8 is bonded to a nitrogen atom connecting a ring containing _X9 to _X12 and _X19 and a ring containing _X13 to _X16 and _X20 . It is a carbon atom
Each _RA1 is independently a hydrogen atom, a substituent, or one or more pairs of a plurality of _RA1s directly bonded to each other to form a ring. Forming a ring through heteroatoms,
_RA1 as a substituent is an aryl group having 6 to 30 substituted or unsubstituted ring-forming carbon atoms, a heteroaryl group having 5 to 30 substituted or unsubstituted ring-forming atoms, and 1 to 1 substituted or unsubstituted ring-forming atom. 30 alkyl groups, substituted or unsubstituted fluoroalkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted aralkyl groups having 7 to 30 carbon atoms. , A substituted phosphoryl group, a substituted silyl group, a cyano group, a nitro group, and any group selected from the group consisting of a carboxy group.
Multiple _RA1s as substituents are the same as or different from each other.
In the general formulas (1a) to (1j), * represents a bonding position with the ring (F).
In the general formulas (1a) to (1j), A ₁ and A ₂ are independently single-bonded, oxygen atom (O), sulfur atom (S), C (R ₃₀₂₁ ) (R ₃₀₂₂ ), Si ( R ₃₀₂₃ ) (R ₃₀₂₄ ), C (= O), S (= O), SO ₂ or N (R ₃₀₂₅ ). R ₃₀₂₁ to R ₃₀₂₅ are independently hydrogen atoms or substituents, and R ₃₀₂₁ to R ₃₀₂₅ as substituents are independently substituents or unsubstituted aryls having 6 to 30 ring-forming carbon atoms. Group, substituted or unsubstituted heteroaryl group having 5 to 30 carbon atoms, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted fluoroalkyl group having 1 to 30 carbon atoms, substituted or unsubstituted. From the group consisting of an unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted aralkyl group having 7 to 30 carbon atoms, a substituted phosphoryl group, a substituted silyl group, a cyano group, a nitro group, and a carboxy group. It is one of the groups selected and
In the general formulas (1a) to (1j), Ara is an aryl group having 6 to 30 substituted or unsubstituted ring-forming carbon atoms, a substituted or unsubstituted heteroaryl group having 5 to 30 ring-forming atoms, substituted or substituted. Unsubstituted alkyl groups with 1 to 30 carbon atoms, substituted or unsubstituted fluoroalkyl groups with 1 to 30 carbon atoms, substituted or unsubstituted ring-forming cycloalkyl groups with 3 to 30 carbon atoms, substituted or unsubstituted carbons. It is any group selected from the group consisting of an aralkyl group having a number of 7 to 30, a substituted phosphoryl group, and a substituted silyl group. ) In the organic electroluminescence device according to claim 33.
The third compound is an organic electroluminescence device, which is a compound represented by the general formula (31). The organic electroluminescence device according to any one of claims 1 to 34.
The light emitting layer is an organic electroluminescence element which is a layer formed by using the composition containing the first compound and the second compound as a vapor deposition source. An electronic device equipped with the organic electroluminescence device according to any one of claims 1 to 35.

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