JP2020158436A - Compounds, organic electroluminescent element material, organic electroluminescent element, and electronic apparatus - Google Patents

Abstract

To provide compounds having excellent capabilities for use in an organic EL element.SOLUTION: The invention provides compounds represented by any of the formulas (1) to (3). In the formulas (1) to (3), R1 and R2 are each a nitrogen-containing fused heterocyclic compound or a carbazole-based compound, where R1 and R2 are different from each other.SELECTED DRAWING: None

Description

The present invention relates to compounds, materials for organic electroluminescent devices, organic electroluminescent devices, and electronic devices.

When a voltage is applied to an organic electroluminescence device (hereinafter, may be referred to as an “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 devices that use light emitted from singlet excitons are being applied to full-color displays such as mobile phones and televisions, but are said to have an internal quantum efficiency of 25% as a limit. Therefore, studies are being conducted to improve the performance of the organic EL element.

Further, it is expected that an organic EL element can 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.
For example, TADF (Thermally Activated Fluorescence) mechanism (mechanism) has been studied. In this TADF mechanism, when a material having a small energy difference (ΔST) between the singlet level and the triplet level is used, the reverse intersystem crossing from the triplet exciter to the singlet exciter occurs thermally. It is a mechanism that utilizes the phenomenon. Thermal activation delayed fluorescence is described, for example, in "Chihaya Adachi," Device Properties of Organic Semiconductors, "Kodansha, published on April 1, 2012, pp. 261-268".
As a compound exhibiting TADF property, for example, a compound in which a donor site and an acceptor site are bound in an molecule is known.
For example, Patent Documents 1, 2, 4 and 5 disclose compounds in which a carbazole group is bonded to dicyanobenzene.
Further, Patent Document 3 and Non-Patent Document 1 disclose a compound in which a condensed carbazole group is bonded to dicyanobenzene.

Korean Publication No. 2017-0035376 Gazette Korean Publication No. 2017-0037135 International Publication No. 2014/208698 International Publication No. 2016/056559 International Publication No. 2014/146752

Chemical Communications (Cambridge, United Kingdom) (2015), 51 (38), 8105-8107

In recent years, as a compound that can be used in an organic EL device, a compound having more excellent performance has been required.

An object of the present invention is a compound having excellent performance for use in an organic EL element, a material for an organic EL element containing the compound, an organic EL element using the compound, and an electronic device equipped with the organic EL element. Is to provide.

According to one aspect of the present invention, a compound represented by any of the following general formulas (1) to (3) is provided.

In the general formulas (1) to (3),
R ₁ is a group represented by any of the following general formulas (101) to (115) and (201) to (204).
R ₂ is a group represented by any of the following general formulas (101) to (115), (201) to (204) and the following general formula (X).
However, R ₁ and R ₂ are different from each other.

In the general formulas (101) to (115), R _{11 to} R ₂₀ are independent hydrogen atoms or substituents, and R ₃₁ and R ₃₂ are independent substituents.
R _{11 to} R ₂₀ as substituents are independent of each other.
Substituted or unsubstituted ring-forming aryl groups having 6 to 14 carbon atoms,
Substituted or unsubstituted heterocyclic groups having 5 to 14 ring-forming atoms,
Substituent or unsubstituted alkyl groups with 1 to 6 carbon atoms,
Substituent or unsubstituted alkoxy groups having 1 to 6 carbon atoms,
Substituent or unsubstituted alkylthio groups having 1 to 6 carbon atoms,
Substituent or unsubstituted ring-forming aryloxy groups having 6 to 14 carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming arylamino group having 6 to 14 carbon atoms.
R ₃₁ and R ₃₂ as substituents are independent of each other.
Substituted or unsubstituted ring-forming aryl groups having 6 to 14 carbon atoms,
Substituted or unsubstituted heterocyclic groups having 5 to 14 ring-forming atoms,
Substituent or unsubstituted alkyl groups with 1 to 6 carbon atoms,
It is a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming aryloxy group having 6 to 14 carbon atoms. * Independently represent the binding site of the benzene ring with the carbon atom in the general formulas (1) to (3).

In the general formulas (201) to (204), R _{21 to} R ₃₀ are independently hydrogen atoms or substituents, and R ₃₃ is a substituent.
R _{21 to} R ₃₀ as substituents are independent of each other.
Substituted or unsubstituted ring-forming aryl groups having 6 to 14 carbon atoms,
Substituted or unsubstituted heterocyclic groups having 5 to 14 ring-forming atoms,
Substituent or unsubstituted alkyl groups with 1 to 6 carbon atoms,
Substituent or unsubstituted alkoxy groups having 1 to 6 carbon atoms,
Substituent or unsubstituted alkylthio groups having 1 to 6 carbon atoms,
Substituent or unsubstituted ring-forming aryloxy groups having 6 to 14 carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming arylamino group having 6 to 14 carbon atoms.
R ₃₃ as a substituent is
Substituted or unsubstituted ring-forming aryl groups having 6 to 14 carbon atoms,
Substituted or unsubstituted heterocyclic groups having 5 to 14 ring-forming atoms,
Substituent or unsubstituted alkyl groups with 1 to 6 carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming aryloxy group having 6 to 14 carbon atoms.
However, when R ₃₃ is a substituted aryl group having 6 to 14 carbon atoms, the substituent is not a cyano group. * Independently represent the binding site of the benzene ring with the carbon atom in the general formulas (1) to (3).

In the general formula _{(X), R} 161 _{~R 168} each independently represent a hydrogen atom or a substituent, _R 161 _{to R 168} as a substituent, each independently,
Halogen atom,
Substituted or unsubstituted ring-forming aryl groups having 6 to 14 carbon atoms,
Substituted or unsubstituted heterocyclic groups having 5 to 14 ring-forming atoms,
Substituent or unsubstituted alkyl groups with 1 to 6 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkylsilyl group having 3 to 6 carbon atoms,
Substituent or unsubstituted alkoxy groups having 1 to 6 carbon atoms,
Substituent or unsubstituted ring-forming aryloxy groups having 6 to 14 carbon atoms,
Substituent or unsubstituted alkylamino groups having 2 to 12 carbon atoms,
It is 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. * Independently represent the binding site of the benzene ring with the carbon atom in the general formulas (1) to (3).

According to one aspect of the present invention, there is provided a material for an organic electroluminescence device containing the compound according to the above-mentioned aspect of the present invention.

According to one aspect of the present invention, it has an anode, a cathode, and a first organic layer contained between the anode and the cathode, and the first organic layer contains the first compound. The first compound includes, and an organic electroluminescence element which is a compound according to one aspect of the present invention described above is provided.

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

According to one aspect of the present invention, a compound having excellent performance for use in an organic EL device, a material for an organic EL device containing the compound, an organic EL device using the compound, and the organic EL device are mounted. Electronic devices can be provided.

It is a figure which shows the schematic structure of an example of the organic electroluminescence device which concerns on 3rd Embodiment of this invention. It is the schematic 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 between the energy level of the 1st compound and the 2nd compound in the light emitting layer of an example of the organic electroluminescence device which concerns on 3rd Embodiment of this invention, and the energy transfer. It is a figure which shows the relationship between the energy level of the 1st compound, the 2nd compound, and the 3rd compound, and the energy transfer in the light emitting layer of an example of the organic electroluminescence element which concerns on 4th Embodiment of this invention. It is a figure which shows the relationship between the energy level of the 1st compound and the 4th compound in the light emitting layer of an example of the organic electroluminescence device which concerns on 5th Embodiment of this invention, and the energy transfer.

[First Embodiment]
〔Compound〕
The compound according to this embodiment is a compound represented by any of the following general formulas (1) to (3).

In the general formulas (1) to (3),
R ₁ is a group represented by any of the following general formulas (101) to (115) and (201) to (204).
R ₂ is a group represented by any of the following general formulas (101) to (115), (201) to (204) and the following general formula (X).
However, R ₁ and R ₂ are different from each other.

In the general formulas (101) to (115), R _{11 to} R ₂₀ are independent hydrogen atoms or substituents, and R ₃₁ and R ₃₂ are independent substituents.
R _{11 to} R ₂₀ as substituents are independent of each other.
Substituted or unsubstituted ring-forming aryl groups having 6 to 14 carbon atoms,
Substituted or unsubstituted heterocyclic groups having 5 to 14 ring-forming atoms,
Substituent or unsubstituted alkyl groups with 1 to 6 carbon atoms,
Substituent or unsubstituted alkoxy groups having 1 to 6 carbon atoms,
Substituent or unsubstituted alkylthio groups having 1 to 6 carbon atoms,
Substituent or unsubstituted ring-forming aryloxy groups having 6 to 14 carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming arylamino group having 6 to 14 carbon atoms.
R ₃₁ and R ₃₂ as substituents are independent of each other.
Substituted or unsubstituted ring-forming aryl groups having 6 to 14 carbon atoms,
Substituted or unsubstituted heterocyclic groups having 5 to 14 ring-forming atoms,
Substituent or unsubstituted alkyl groups with 1 to 6 carbon atoms,
It is a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming aryloxy group having 6 to 14 carbon atoms.
A plurality of R _11s are the same or different from each other, a plurality of R _12s are the same or different from each other, a plurality of R _13s are the same or different from each other, a plurality of R _14s are the same or different from each other, and a plurality of R _15s are the same or different from each other. Same or different from each other, multiple R _16s are the same or different from each other, multiple R _17s are the same or different from each other, multiple R _18s are the same or different from each other, and multiple R _19s are the same or different from each other. 's _{R 20,} equal to or different from each other, a plurality of _{R 31,} equal to or different from each other, a plurality of _{R 32} are the same or different from each other. * Independently represent the binding site of the benzene ring with the carbon atom in the general formulas (1) to (3).

In the general formulas (201) to (204), R _{21 to} R ₃₀ are independently hydrogen atoms or substituents, and R33 is a substituent.
R _{21 to} R ₃₀ as substituents are independent of each other.
Substituted or unsubstituted ring-forming aryl groups having 6 to 14 carbon atoms,
Substituted or unsubstituted heterocyclic groups having 5 to 14 ring-forming atoms,
Substituent or unsubstituted alkyl groups with 1 to 6 carbon atoms,
Substituent or unsubstituted alkoxy groups having 1 to 6 carbon atoms,
Substituent or unsubstituted alkylthio groups having 1 to 6 carbon atoms,
Substituent or unsubstituted ring-forming aryloxy groups having 6 to 14 carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming arylamino group having 6 to 14 carbon atoms.
R ₃₃ as a substituent is
Substituted or unsubstituted ring-forming aryl groups having 6 to 14 carbon atoms,
Substituted or unsubstituted heterocyclic groups having 5 to 14 ring-forming atoms,
Substituent or unsubstituted alkyl groups with 1 to 6 carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming aryloxy group having 6 to 14 carbon atoms.
However, when R ₃₃ is a substituted aryl group having 6 to 14 carbon atoms, the substituent is not a cyano group.
A plurality of R _21s are the same or different from each other, a plurality of R _22s are the same or different from each other, a plurality of R _23s are the same or different from each other, a plurality of R _24s are the same or different from each other, and a plurality of R _25s are the same or different from each other. Same or different from each other, multiple R _26s are the same or different from each other, multiple R _27s are the same or different from each other, multiple R _28s are the same or different from each other, and multiple R _29s are the same or different from each other. R ₃₃ are the same or different from each other. * Independently represent the binding site of the benzene ring with the carbon atom in the general formulas (1) to (3).

In the general formula _{(X), R} 161 _{~R 168} each independently represent a hydrogen atom or a substituent, _R 161 _{to R 168} as a substituent, each independently,
Halogen atom,
Substituted or unsubstituted ring-forming aryl groups having 6 to 14 carbon atoms,
Substituted or unsubstituted heterocyclic groups having 5 to 14 ring-forming atoms,
Substituent or unsubstituted alkyl groups with 1 to 6 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkylsilyl group having 3 to 6 carbon atoms,
Substituent or unsubstituted alkoxy groups having 1 to 6 carbon atoms,
Substituent or unsubstituted ring-forming aryloxy groups having 6 to 14 carbon atoms,
Substituent or unsubstituted alkylamino groups having 2 to 12 carbon atoms,
It is 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. * Independently represent the binding site of the benzene ring with the carbon atom in the general formulas (1) to (3).

The present inventors have excellent performance for using a compound represented by any of the general formulas (1) to (3) (hereinafter, also referred to as "compound of the present embodiment") for an organic EL device. I found that.
Having excellent performance for use in an organic EL element means that, for example, at least one of the following (1) to (3) is realized.
(1) When the compound of the present embodiment is used for an organic EL element, at least one of the luminous efficiency, element life, drive voltage, and brightness of the organic EL element is improved.
(2) Excellent TADF properties.
(3) Excellent heat resistance.

And is excellent in TADF properties, for example, refers to "the value of the _X D / _{X P"} measured by the measuring method described below is 0.05 or more. Note that the value of _{X P} is the amount of Prompt luminescence (immediate light emission), the value of _{X D} is the amount of Delay emission (delayed luminescence).
The excellent heat resistance means that the decomposition temperature of the compound of the present embodiment is high or the sublimation temperature is low. For example, when an organic EL device is manufactured using a compound having excellent heat resistance, a relatively high temperature can be applied to the compound, so that the compound can be vapor-deposited more quickly for the purpose. An organic layer (for example, a light emitting layer, a hole transport layer, an electron transport layer, etc.) can be obtained. As a result, the manufacturing time of the organic EL element can be shortened. This reduction in manufacturing time also leads to a reduction in manufacturing time of, for example, an electronic device (for example, a display device such as an organic EL panel) equipped with an organic EL element. Therefore, by using a compound having excellent heat resistance, it is possible to reduce the cost of the organic EL element and the electronic device equipped with the organic EL element.
As an index representing the heat resistance (sublimation temperature) of the compound of the present embodiment, for example, a 1% weight loss temperature and a 5% weight loss temperature measured by thermogravimetric differential thermal measurement (TG-DTA) can be used. The 1% weight loss temperature and the 5% weight loss temperature can be measured under the following conditions using a differential thermogravimetric simultaneous measuring device.
Thermogravimetric differential thermal measurement (TG-DTA) is a method of continuously measuring the mass change of a sample when the sample is heated, and is used for detecting a physical change accompanied by a mass change such as sublimation and evaporation.

-Measurement conditions-
-Device: Differential thermal weight simultaneous measurement device (STA7200RV, manufactured by Hitachi High-Technologies Corporation)
・ Container: Aluminum bread ・ Sample mass: 3.0 mg
・ Measurement atmosphere: Nitrogen gas atmosphere ・ Temperature rise rate: 10 ℃ / min ・ Measurement range: 35 ℃ or more and 600 ℃ or less

In the compound of the present embodiment, R ₂ is preferably a group represented by any of the general formulas (101) to (115) and (201) to (204).

In the compound of the present embodiment, R ₁ is a group represented by any of the general formulas (101) to (110) and (201) to (204), and R ₂ is the general formula (101). It is also preferable that the group is represented by any of (110), (201) to (204) and the general formula (X).

In the compound of the present embodiment, R ₁ is a group represented by any of the general formulas (101) to (105), (107), (109) to (115) and (201) to (204). Yes, R ₂ is represented by any of the general formulas (101) to (105), (107), (109) to (115), (201) to (204), and the general formula (X). It is also preferable that it is a group.

In the compound of the present embodiment, R ₁ is a group represented by any of the general formulas (101) to (105), and R ₂ is a group represented by any of the general formulas (101) to (105). It is also preferable that it is a represented group.

In the compound of the present embodiment, R ₁ is a group represented by any of the general formulas (106) to (110), and R ₂ is a group represented by any of the general formulas (106) to (110). It is also preferable that it is a represented group.

In the compound of the present embodiment, R ₁ is a group represented by any of the general formulas (111) to (115), and R ₂ is a group represented by any of the general formulas (111) to (115). It is also preferable that it is a represented group.

In the compound of the present embodiment, R ₁ is a group represented by any of the general formulas (101) to (105), and R ₂ is a group represented by any of the general formulas (106) to (110). It is also preferable that it is a represented group.

In the compound of the present embodiment, R ₁ is a group represented by any of the general formulas (101) to (105), and R ₂ is a group represented by any of the general formulas (111) to (115). It is also preferable that it is a represented group.

In the compound of the present embodiment, R ₁ is a group represented by any of the general formulas (101) to (105), and R ₂ is a group represented by any of the general formulas (201) to (204). It is also preferable that it is a represented group.

In the compound of the present embodiment, R ₁ is a group represented by any of the general formulas (106) to (110), and R ₂ is a group represented by any of the general formulas (111) to (115). It is also preferable that it is a represented group.

In the compound of the present embodiment, R ₁ is a group represented by any of the general formulas (106) to (110), and R ₂ is a group represented by any of the general formulas (201) to (204). It is also preferable that it is a represented group.

In the compound of the present embodiment, R ₁ is a group represented by any of the general formulas (111) to (115) and (201) to (204), and R ₂ is the general formula (X). It is also preferable that the group is represented by.

The compound of the present embodiment is preferably a compound represented by the general formula (1).

The compound of the present embodiment is also preferably a compound represented by the general formula (2).

The compound of the present embodiment is also preferably a compound represented by the general formula (3).

In the general formulas (101) to (115), (201) to (204) and the general formula (X), R _{11 to} R ₂₀ , R _{21 to} R ₃₀ , R _{31 to} R ₃₃ and R _{161 to} R _168. Are independently hydrogen atoms or substituents, and R _{11 to} R ₂₀ , R _{21 to} R ₃₀ , R _{31 to} R _33, and R _{161 to} R ₁₆₈ as substituents are independently substituted or absent, respectively. A substituted aryl group having 6 to 14 carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 14 ring-forming atoms, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms is preferable.
R _{11 to} R ₂₀ , R _{21 to} R ₃₀ , R _{31 to} R ₃₃ and R _{161 to} R _{168 as} substituents are independently unsubstituted, ring-forming aryl groups having 6 to 14 carbon atoms and unsubstituted. More preferably, it is a heterocyclic group having 5 to 14 ring-forming atoms or an unsubstituted alkyl group having 1 to 6 carbon atoms.

In the general formulas (101) to (115) and (201) to (204), R ₁₃ and R ₂₃ are independent substituents, and R ₁₃ and R ₂₃ as substituents are independent, respectively. , A substituted or unsubstituted ring-forming aryl group having 6 to 14 carbon atoms, a substituted or unsubstituted ring-forming atomic number of 5 to 14 heterocyclic groups, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms. It is also preferable.

In the general formulas (101) to (115), (201) to (204) and the general formula (X), R _{11 to} R ₂₀ , R _{21 to} R ₃₀ and R _{161 to} R ₁₆₈ are hydrogen atoms. It is also preferable that R _{31 to} R ₃₃ are independently substituted or unsubstituted ring-forming aryl groups having 6 to 14 carbon atoms, or substituted or unsubstituted alkyl groups having 1 to 6 carbon atoms.
R _{11 to} R ₂₀ , R _{21 to} R _30, and R _{161 to} R ₁₆₈ are hydrogen atoms, and R _{31 to} R ₃₃ are independently unsubstituted aryl groups having 6 to 14 carbon atoms. Alternatively, it is more preferably an unsubstituted alkyl group having 1 to 6 carbon atoms.

In the general formulas (101) to (115), (201) to (204) and the general formula (X), the substituent in the case of "substituted or unsubstituted" has 1 to 1 substituted or unsubstituted carbon atoms. 30 alkyl groups, substituted or unsubstituted alkyl halide groups having 1 to 30 carbon atoms, substituted or unsubstituted ring-forming cycloalkyl groups having 3 to 30 carbon atoms, substituted or unsubstituted ring-forming alkyl groups having 6 to 30 carbon atoms. Aryl group, substituted or unsubstituted ring-forming heteroaryl group having 5 to 30 atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms. , Substituent or unsubstituted alkylthio group having 1 to 30 carbon atoms, substituted or unsubstituted ring-forming carbon number 6 to 30 aryloxy group, substituted or unsubstituted ring-forming carbon number 6 to 30 arylthio group, substituted or unsubstituted. Unsubstituted alkenyl group with 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group with 2 to 30 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 30 carbon atoms, substituted or unsubstituted carbon number 1 to 30 Alkylsulfonyl group, substituted or unsubstituted ring-forming arylcarbonyl group having 6 to 30 carbon atoms, substituted or unsubstituted acyl group having 1 to 30 carbon atoms, halogen atom, carboxy group, substituted or unsubstituted amino group, It is preferably a nitro group, a cyano group, a substituted or unsubstituted silyl group, a substituted phosphoryl group, a hydroxy group, a substituted phosphino group, an ester group, a siloxanyl group, or a carbamoyl group.
Substituents in the case of "substituted or unsubstituted" are substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, substituted or unsubstituted alkyl halide groups having 1 to 30 carbon atoms, substituted or unsubstituted rings. Cycloalkyl group with 3 to 30 carbon atoms, substituted or unsubstituted ring-forming aryl group with 6 to 30 carbon atoms, substituted or unsubstituted heteroaryl group with 5 to 30 ring-forming atoms, substituted or unsubstituted carbon An alkoxy group having a number of 1 to 30, a halogenated alkoxy group having a substituted or unsubstituted carbon number of 1 to 30, an alkylthio group having a substituted or unsubstituted carbon number of 1 to 30, and a substituted or unsubstituted ring-forming carbon number of 6 to 30. Aryloxy group, substituted or unsubstituted ring-forming arylthio group having 6 to 30 carbon atoms, substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, substituted. Alternatively, it is an unsubstituted aralkyl group having 7 to 30 carbon atoms, a halogen atom, a carboxy group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted silyl group, a substituted phosphoryl group, or a hydroxy group. Is more preferable.

In the general formulas (101) to (115), (201) to (204) and the general formula (X), the substituent in the case of "substituted or unsubstituted" has an unsubstituted carbon number of 1 to 30. Alkyl group, unsubstituted alkyl halide group having 1 to 30 carbon atoms, unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms, unsubstituted ring-forming alkyl group having 6 to 30 carbon atoms, unsubstituted ring Heteroaryl groups with 5 to 30 atoms, unsubstituted alkoxy groups with 1 to 30 carbon atoms, unsubstituted alkoxy groups with 1 to 30 carbon atoms, unsubstituted alkylthio groups with 1 to 30 carbon atoms, none. Substitutable ring-forming carbon number 6 to 30 aryloxy group, unsubstituted ring-forming carbon number 6 to 30 arylthio group, unsubstituted 2 to 30 carbon number alkenyl group, unsubstituted ring-forming carbon number 2 to 30 alkynyl Group, unsubstituted aralkyl group having 7 to 30 carbon atoms, unsubstituted alkylsulfonyl group having 1 to 30 carbon atoms, unsubstituted ring-forming ring forming arylcarbonyl group having 6 to 30 carbon atoms, and unsubstituted 1 to 30 carbon atoms. It is preferably an acyl group, a halogen atom, a carboxy group, an amino group, a nitro group, a cyano group, a silyl group, a hydroxy group, an ester group, a siloxanyl group, or a carbamoyl group.
The substituent in the case of "substituted or unsubstituted" is the case of "substituted or unsubstituted" in the general formulas (101) to (115), (201) to (204) and the general formula (X). Substituents are an unsubstituted alkyl group having 1 to 30 carbon atoms, an unsubstituted alkyl halide group having 1 to 30 carbon atoms, an unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms, and an unsubstituted ring. An aryl group having 6 to 30 carbon atoms, a heteroaryl group having an unsubstituted ring-forming atom number of 5 to 30, an alkoxy group having an unsubstituted carbon number of 1 to 30, and a halogenated alkoxy group having an unsubstituted carbon number of 1 to 30 , An unsubstituted alkylthio group having 1 to 30 carbon atoms, an unsubstituted ring-forming carbon number 6 to 30 aryloxy group, an unsubstituted ring-forming carbon number 6 to 30 arylthio group, and an unsubstituted ring-forming carbon number 2 to 30 More preferably, it is an alkenyl group, an unsubstituted alkynyl group having 2 to 30 carbon atoms, a halogen atom, a carboxy group, an amino group, a nitro group, a cyano group, a silyl group, or a hydroxy group.

In the compound of the present embodiment, as R ₁ , for example, the following groups NO-1 to NO-20, groups NS-1 to NS-20, groups NC-1 to NC-20 and groups NN-1 to NN- 16 is mentioned.
In the compound of the present embodiment, as R ₂ , for example, the following groups NO-1 to NO-20, groups NS-1 to NS-20, groups NC-1 to NC-20, and groups NN-1 to NN-16 And group 1'.
* Independently represent the binding site of the benzene ring with the carbon atom in the general formulas (1) to (3).

-Method for producing a compound according to this embodiment The compound according to this embodiment can be produced, for example, by the method described in Examples described later. The compound according to this embodiment can be produced by following the reaction described in Examples described later and using a known alternative reaction or raw material suitable for the target product.

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

[Second Embodiment]
[Material for organic EL elements]
The material for an organic EL device according to the second embodiment includes the compound of the first embodiment (at least one of the compounds represented by any of the general formulas (1) to (3)).
According to the second embodiment, a material for an organic EL device having excellent performance for use in an organic EL device can be obtained.
The material for the organic EL device according to the second embodiment may further contain other compounds. When the material for an organic EL device according to the second embodiment further contains other compounds, the other compounds may be solid or liquid.

[Third Embodiment]
[Organic EL element]
Hereinafter, the configuration of the organic EL element according to the third embodiment will be described.

The organic EL element includes an organic layer between both electrodes of the anode and the cathode. This organic layer is usually formed by laminating a plurality of layers composed of organic compounds. The organic layer may further contain an inorganic compound. The organic EL device of the present embodiment has a first organic layer contained between the anode and the cathode. The first organic layer contains at least one of the compounds represented by any of the general formulas (1) to (3).
The first organic layer is at least one selected from the group consisting of, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron injection layer, an electron transport layer, a hole barrier layer, an electron barrier layer, and the like. That layer can be mentioned.

The first organic layer is preferably a light emitting layer.
In the organic EL device of the present embodiment, the first organic layer is a light emitting layer.
In the present embodiment, the organic layer may be composed of only a light emitting layer as the first organic layer, and for example, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a hole. It may further have at least one layer selected from the group consisting of a barrier layer, an electron barrier layer and the like.

FIG. 1 shows a schematic configuration of an example of an organic EL device according to the present 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. In the organic layer 10, the hole injection layer 6, the hole transport layer 7, the light emitting layer 5 as the first organic layer, the electron transport layer 8, and the electron injection layer 9 are laminated in this order from the anode 3 side. Is composed of.

In the organic EL element 1 of the present embodiment, the light emitting layer 5 contains the first compound.
The first compound is a compound according to the first embodiment (at least one of the compounds represented by any of the general formulas (1) to (3)).
The light emitting layer 5 preferably does not contain a phosphorescent material (dopant material).
The light emitting layer 5 preferably does not contain a heavy metal complex and a phosphorescent rare earth metal complex. Here, examples of the heavy metal complex include an iridium complex, an osmium complex, a platinum complex, and the like.
It is also preferable that the light emitting layer 5 does not contain a metal complex.

In the organic EL element 1 of the present embodiment, the light emitting layer 5 includes a first compound and a second compound.
In this embodiment, the first compound is preferably a host material (sometimes referred to as a matrix material) and the second compound is sometimes referred to as a dopant material (guest material, emitter, luminescent material). .) Is preferable.

<First compound>
The first compound is the compound according to the first embodiment.
The first compound is preferably a delayed fluorescent compound.

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

In general, 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 attenuation 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 light emission in TADF materials is classified into a light emitting component from a singlet exciton generated by the first PL excitation and a light emitting component from a singlet exciton generated via a triplet exciton. The lifetime of singlet excitons generated by the first PL excitation is on the nanosecond order and is very short. Therefore, the light emission from the singlet exciton is rapidly attenuated after irradiation with the pulse laser.
On the other hand, delayed fluorescence is slowly attenuated due to light emission from singlet excitons generated via triplet excitons having a long lifetime. As described above, there is a large time difference between the light emission from the singlet exciton generated by the first PL excitation and the light emission from the singlet exciton generated via the triplet exciton. Therefore, the emission intensity derived from delayed fluorescence can be obtained.

FIG. 2 shows a schematic diagram of an exemplary device for measuring transient PL. A method of measuring transient PL using FIG. 2 and an example of 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 having 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 apparatus 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 matrix 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. Light is emitted in a direction of 90 degrees with respect to the irradiation direction of the excitation light, the extracted light is separated by the 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 matrix 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. For the thin film sample B, the following reference compound H2 was used as the matrix material, and the reference compound D1 was used as the doping material to prepare a thin film sample as described above.

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

By transient PL measurement as described above, it is possible to obtain an emission attenuation curve in which the vertical axis is the emission intensity and the horizontal axis is 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 the delayed fluorescence material, the ratio of the intensity of the slowly decaying fluorescence to the intensity of the rapidly decaying fluorescence is large to some extent.

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 light emission (delayed light emission) is light emission that is not immediately observed after being excited by the pulsed light but is observed thereafter.

The amounts of Prompt emission and Delay emission and their ratios can be determined by the same method as described in "Nature 492, 234-238, 2012" (Reference 1). The device used to calculate the amounts 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 embodiment, a sample prepared by the following method is used for measuring the delayed fluorescence of the first compound. For example, the first compound is dissolved in toluene to prepare a dilute solution with 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 Kogaku 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 amounts of Prompt emission and Delay emission and their ratios can be determined by the same method as described in "Nature 492, 234-238, 2012" (Reference 1). The device used to calculate the amounts of Prompt emission and Delay emission is not limited to the apparatus described in Reference 1 or the apparatus shown in FIG.
When in the present embodiment, the amount of Prompt luminescence measurement target compound (first compound) (Immediate emission) and _{X P,} the amount of Delay emission (delayed luminescence) was _{X D, X D} / _{X P} The value of is preferably 0.05 or more.
The measurement of the amount and the ratio of the Prompt emission and the Delay emission of the compound other than the first compound in the present specification is the same as the measurement of the amount and the ratio of the Prompt emission and the Delay emission of the first compound.

<Second compound>
The second compound is preferably a fluorescent compound. The second compound may be a delayed fluorescence compound or a compound that does not exhibit delayed fluorescence.

As the second compound according to the present embodiment, a fluorescent material can be used. Specific examples of the fluorescent material include bisarylaminonaphthalene derivatives, aryl-substituted naphthalene derivatives, bisarylaminoanthracene derivatives, aryl-substituted anthracene derivatives, bisarylaminopyrene derivatives, aryl-substituted pyrene derivatives, and bisarylamino. Chrycene derivatives, aryl-substituted chrysene derivatives, bisarylaminofluorantene derivatives, aryl-substituted fluoranthene derivatives, indenoperylene derivatives, acenaftfluoranthen derivatives, pyrometheneboron complex compounds, compounds having a pyromethene skeleton, compounds having a pyromethene skeleton Examples thereof include metal complexes, diketopyrrolopyrrole derivatives, perylene derivatives, and naphthacene derivatives.

In the present embodiment, the second compound is preferably a compound represented by the following general formula (20).
The second compound is a compound represented by the following general formula (20).
The second compound is preferably a compound having fluorescence luminescence.

In the general formula (20),
In the general formula (20),
X is a nitrogen atom or a carbon atom bonded to Y,
Y is a hydrogen atom or a substituent,
R _{21 to} R ₂₆ are independently hydrogen atoms or substituents, or R ₂₁ and R ₂₂ pairs, R ₂₂ and R ₂₃ pairs, R ₂₄ and R ₂₅ pairs, and R ₂₅ and R. Any one or more of the ₂₆ pairs combine with each other to form a ring.
Y and R _{21 to} R ₂₆ as substituents are independent of each other.
Substituent 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,
Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,
Substituent or unsubstituted alkoxy groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
Substituent or unsubstituted alkylthio groups having 1 to 30 carbon atoms,
Substituent or unsubstituted ring-forming aryloxy groups having 6 to 30 carbon atoms,
Substituted or unsubstituted ring-forming arylthio groups having 6 to 30 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 30 carbon atoms,
Substituent or unsubstituted aralkyl groups having 7 to 30 carbon atoms,
A heteroaryl group having 5 to 30 substituted or unsubstituted ring-forming atoms,
Halogen atom,
Carboxy group,
Substituted or unsubstituted ester groups,
Substituted or unsubstituted carbamoyl groups,
Substituted or unsubstituted amino groups,
Nitro group,
Cyano group,
Selected from the group consisting of substituted or unsubstituted silyl groups and substituted or unsubstituted siloxanyl groups.
Z ₂₁ and Z ₂₂ are independent substituents, or Z ₂₁ and Z ₂₂ are bonded to each other to form a ring.
Z ₂₁ and Z ₂₂ as substituents are independent of each other.
Halogen atom,
Substituent or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
It is selected from the group consisting of substituted or unsubstituted alkoxy halide groups having 1 to 30 carbon atoms and substituted or unsubstituted ring-forming aryloxy groups having 6 to 30 carbon atoms.

In the general formula (20), for example, when the pair of R ₂₅ and R ₂₆ are bonded to each other to form a ring, the second compound is represented by the following general formula (21).

In the general formula _{(21), X, Y,} R 21 ~R 24, Z 21, and _{Z 22} are each, _X in the general formula _{(20), Y, R 21} ~R 24, Z 21, and Z Synonymous with ₂₂ , R _{27 to} R ₃₀ are independent hydrogen atoms or substituents, and R _{21 to} R ₂₄ are listed as substituents when R _{27 to} R ₃₀ are substituents. Synonymous with substituent.

In the general formula (20), when Z ₂₁ and Z ₂₂ are bonded to each other to form a ring, the second compound is represented by, for example, the following general formula (20A) or the following general formula (20B). Will be done. However, the second compound is not limited to the following structure.

In the general formula (20A), X, Y, and R _{21 to} R ₂₆ are synonymous with X, Y, and R _{21 to} R ₂₆ in the general formula (20), respectively, and R _1A is independent of each other. In addition, when it is a hydrogen atom or a substituent and R _1A is a substituent, the substituent is synonymous with the substituents listed for R _{21 to} R ₂₆ , and n3 is 4.
In the general formula (20B), X, Y, and R _{21 to} R ₂₆ are synonymous with X, Y, and R _{21 to} R ₂₆ in the general formula (20), respectively, and R _1B are independent of each other. In addition, when it is a hydrogen atom or a substituent and R _1B is a substituent, the substituent is synonymous with the substituents listed for R _{21 to} R ₂₆ , and n4 is 4.

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

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

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

It is also preferable that at least one of the Z ₂₁ and the Z ₂₂ is a group represented by the following general formula (20a).

In the general formula (20a), A is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted alkyl halide group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming carbon. It is an aryl group of number 6 to 12, L ₂ is a substituted or unsubstituted alkylene group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming aryl group having 6 to 12 carbon atoms, and m is a substituted or unsubstituted arylene group. 0,1,2,3,4,5,6, or 7, when m is 3, 4, 5, 6, or 7, a plurality of _{L 2} may be the same or different from each other. m is preferably 0, 1, or 2. When m is 0, A directly bonds to O (oxygen atom).

In the general formula (20), when Z ₂₁ and Z ₂₂ are groups represented by the general formula (20a), the second compound is a compound represented by the following general formula (22).
The second compound is also preferably a compound represented by the following general formula (22).

In the general formula (22), Y, R _{21 to} R ₂₆ when X and X are carbon atoms bonded to Y are X, Y, R _{21 to} R ₂₆ in the general formula (20), respectively. It is synonymous. A ₂₁ and A ₂₂ have the same meaning as A in the general formula (20a), and may be the same as or different from each other. L ₂₁ and L ₂₂ have the same meaning as L ₂ in the general formula (20a), and may be the same as or different from each other. m1 and m2 are 0, 1, 2, 3, 4, 5, 6 or 7, respectively, and preferably 0, 1, or 2. If m1 is 2, 3, 4, 5, 6, or 7, then the plurality of L _21s are the same or different from each other, and if m2 is 2, 3, 4, 5, 6, or 7, then the plurality of L _{21s. 22} are the same or different from each other. When m1 is 0, A ₂₁ is directly bonded to O (oxygen atom), and when m2 is 0, A ₂₂ is directly bonded to O (oxygen atom).

At least one of A and L ₂ in the general formula (20a) is preferably substituted with a halogen atom, and more preferably substituted with a fluorine atom.

A in the general formula (20a) is more preferably a perfluoroalkyl group having 1 to 6 carbon atoms or a perfluoroaryl group having 6 to 12 carbon atoms forming a ring, and a perfluoroalkyl group having 1 to 6 carbon atoms. It is more preferably a group.

L ₂ in the general formula (20a) is more preferably a perfluoroalkylene group having 1 to 6 carbon atoms or a perfluoroarylene group having 6 to 12 carbon atoms forming a ring, and perfluoro having 1 to 6 carbon atoms. It is more preferably an alkylene group.

That is, it is also preferable that the second compound is a compound represented by the following general formula (22a).

In the general formula (22a),
X is synonymous with X in the general formula (20), and Y when X is a carbon atom bonded to Y is synonymous with Y in the general formula (20).
R _{21 to} R ₂₆ are independently synonymous with R _{21 to} R ₂₆ in the general formula (20).
m3 is 0 or more and 4 or less,
m4 is 0 or more and 4 or less,
m3 and m4 are the same as or different from each other.

In the general formulas (20), (21), (22), and (22a),
X is a carbon atom that bonds with Y,
Y is a hydrogen atom or a substituent,
Y as a substituent is an alkyl group having 1 to 30 carbon atoms substituted or unsubstituted, an alkyl halide group having 1 to 30 carbon atoms substituted or unsubstituted, and a ring-forming alkyl group having 6 to 30 substituted or unsubstituted carbon atoms. It is preferably a substituent selected from the group consisting of aryl groups, and more preferably a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms.

In the general formulas (20), (21), (22), and (22a),
In a more preferred embodiment
X is a carbon atom that bonds with Y,
Y is a hydrogen atom or a substituent,
Y as a substituent is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
When Y as a substituent is an aryl group having a ring-forming carbon number of 6 to 30 having a substituent, the substituent is
Substituent or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkoxy groups having 1 to 30 carbon atoms,
Examples thereof include a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms or an aryl group having 6 to 30 carbon atoms substituted with an alkyl group having 1 to 30 carbon atoms.

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

In the general formulas (20), (22), and (22a), at least one of R ₂₁ , R ₂₃ , R ₂₄ , and R ₂₆ is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or It is preferably a substituted or unsubstituted alkyl halide group having 1 to 30 carbon atoms.
In the general formulas (20), (22), and (22a), R ₂₁ , R ₂₃ , R ₂₄ , and R ₂₆ are substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms, or substituted or unsubstituted. It is more preferably an alkyl halide group having 1 to 30 carbon atoms. In this case, it is preferable that R ₂₂ and R ₂₅ are hydrogen atoms.

In the general formulas (20), (22), and (22a), at least one of R ₂₁ , R ₂₃ , R ₂₄ , and R ₂₆ is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. Is preferable.
In the general formulas (20), (22), and (22a), R ₂₁ , R ₂₃ , R ₂₄ , and R ₂₆ are substituted or unsubstituted aryl groups having 6 to 30 carbon atoms. preferable. In this case, it is preferable that R ₂₂ and R ₂₅ are hydrogen atoms.

In the general formulas (20), (22), and (22a),
In a more preferred embodiment
R ₂₁ , R ₂₃ , R ₂₄ , and R ₂₆ are independent of each other.
Substituentally substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms),
A ring-forming alkyl group having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms) substituted or unsubstituted, or a ring-forming alkyl group having 1 to 30 carbon atoms substituted with 6 to 30 carbon atoms (preferably ring forming). It is an aryl group having 6 to 12 carbon atoms).
An embodiment in which R ₂₂ and R ₂₅ are hydrogen atoms can be mentioned.

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

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

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

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

In the general formula (21),
In a more preferred embodiment
R ₂₁ , R ₂₃ , and R ₂₄ are independent of each other.
Substituentally substituted or unsubstituted alkyl groups having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms),
A ring-forming alkyl group having 1 to 30 carbon atoms (preferably 1 to 6 carbon atoms) substituted or unsubstituted, or a ring-forming alkyl group having 1 to 30 carbon atoms substituted with 6 to 30 carbon atoms (preferably ring forming). It is an aryl group having 6 to 12 carbon atoms).
An embodiment in which R ₂₂ is a hydrogen atom can be mentioned.

In the second compound, examples of the alkoxy group substituted with the fluorine atom include 2,2,2-trifluorooloethoxy group, 2,2-difluorooloethoxy group, 2,2,3,3,3. -Pentafluoro-1-propoxy group, 2,2,3,3-tetrafluoro-1-propoxy group, 1,1,1,3,3,3-hexafluoro-2-propoxy group, 2,2,3 , 3,4,4,4-heptafluoro-1-butyloxy group, 2,2,3,3,4,4-hexafluoro-1-butyloxy group, nonafluorotertiary butyloxy group, 2,2,3 , 3,4,4,5,5,5-nonafluoropentanoxy group, 2,2,3,3,4,5,5,6,6,6-undecafluorohexanoxy group, 2,3-bis (trifluoromethyl) -2,3-butandioxy group, 1,1,2,2-tetra (trifluoromethyl) ethyleneglycoxy group, 4,4,5,5,6,6,6 -Heptafluorohexane-1,2-dioxy group, and 4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluorononane-1,2-dioxy group And so on.

In the second compound, the aryloxy group substituted with a fluorine atom or the aryloxy group substituted with a fluoroalkyl group includes, for example, a pentafluorophenoxy group, a 3,4,5-trifluorophenoxy group, 4-. Trifluoromethylphenoxy group, 3,5-bistrifluoromethylphenoxy group, 3-fluoro-4-trifluoromethylphenoxy group, 2,3,5,6-tetrafluoro-4-trifluoromethylphenoxy group, 4-fluoro Examples thereof include a catecholate group, a 4-trifluoromethyl catecholate group, and a 3,5-bistrifluoromethyl catecholate group.

When the second compound is a fluorescent compound, it is preferable that the second 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 spectral fluorometer (F-7000 manufactured by Hitachi High-Tech Science Corporation) is used as the measuring device.

The second compound preferably exhibits red 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 second compound is a red fluorescent compound, the main peak wavelength of the second 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. ..
In the present specification, the green emission means the 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 second compound is a green fluorescent compound, the main peak wavelength of the second compound is preferably 500 nm or more and 560 nm or less, more preferably 500 nm or more and 540 nm or less, and further preferably 510 nm or more and 530 nm or less. ..
In the present specification, the blue emission means the 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 second compound is a blue fluorescent compound, the main peak wavelength of the second compound is preferably 430 nm or more and 480 nm or less, and more preferably 445 nm or more and 480 nm or less.

-Method for producing the second compound The second compound can be produced by a known method.

Specific examples of the second compound according to this embodiment are shown below. The second compound in the present invention is not limited to these specific examples.
There are various notation methods for the coordination bond between the boron atom and the nitrogen atom in the pyrromethene skeleton, such as a solid line, a broken line, an arrow, or omission. In the present specification, it is represented by a solid line, a broken line, or the description thereof is omitted.

<Relationship between the first compound and the second compound in the light emitting layer>
In the organic EL device 1 of the present embodiment, the singlet energy _S 1 (Mat1) of the first compound, a singlet energy _S 1 of the second compound (Mat2), but the relationship of the following equation (Equation 3) It is preferable to satisfy.
_{S 1 (Mat1)> S 1} (Mat2) ... ( number 3)

The energy gap T _77K (Mat1) at 77 [K] of the first compound is preferably larger than the energy gap T _77K (Mat2) at 77 [K] of the second compound. That is, it is preferable to satisfy the relationship of the following mathematical formula (Equation 5).
T _77K (Mat1)> T _77K (Mat2) ... (Equation 5)

When the organic EL element 1 of the present embodiment is made to emit light, it is preferable that the second compound mainly emits light in the light emitting layer 5.

-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] differs from the normally defined triplet energy.
The triplet energy measurement is performed as follows. First, a sample in which a solution in which a compound to be measured is dissolved in an appropriate solvent is sealed in a quartz glass tube is prepared. 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 at the intersection of the tangent line and the horizontal axis.
Here, among the compounds according to the present embodiment, the thermally active delayed fluorescence 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 triplet energy value 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 the energy gap T _77K. .. The compound to be measured is dissolved in EPA (diethyl ether: isopentane: ethanol = 5: 5: 2 (volume ratio)) so as to have a concentration of 10 μmol / L, and this solution is placed in a quartz cell 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] of 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 at 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 phosphorescent 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 the tangent line 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 maximum value on the shortest wavelength side described above, and the slope value 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.
An F-4500 type spectrofluorometer main body manufactured by Hitachi High-Technology Co., Ltd. can be used for the measurement of phosphorescence. 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
The method of measuring the solution using a singlet energy S ₁ (hereinafter sometimes referred to as solution method.), A method described below.
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 of the absorption spectrum on the long wavelength side, 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 singlet energy. To 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 (device name: U3310) manufactured by Hitachi, Ltd.

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

In this embodiment, defines a singlet energy _{S 1,} the difference between the energy gap _{T 77K} at 77 [K] and _{(S 1 -T 77K)} as .DELTA.St.

In this embodiment, the singlet energy _S 1 (Mat1) of the first compound, the difference between the energy gap _T 77K (Mat1) in 77 [K] of the first compound .DELTA.St (Mat1) is preferably It is less than 0.3 eV, more preferably less than 0.2 eV, still more preferably less than 0.1 eV. That is, it is preferable that ΔST (Mat1) satisfies the relationship of the following mathematical formulas (Equation 1A) to (Equation 1C).
ΔST (Mat1) = S ₁ (Mat1) -T _77K (Mat1) <0.3eV (Equation 1A)
ΔST (Mat1) = S ₁ (Mat1) -T _77K (Mat1) <0.2 eV (Equation 1B)
ΔST (Mat1) = S ₁ (Mat1) -T _77K (Mat1) <0.1 eV (Equation 1C)

The organic EL element 1 of the present embodiment preferably emits red light or green light.
When the organic EL element 1 of the present embodiment emits green light, the main peak wavelength of the light emitted from the organic EL element 1 is preferably 500 nm or more and 560 nm or less.
When the organic EL element 1 of the present embodiment emits red light, the main peak wavelength of the light emitted from the organic EL element 1 is preferably 600 nm or more and 660 nm or less.
When the organic EL element 1 of the present embodiment emits blue light, the main peak wavelength of the light emitted from the organic EL element 1 is preferably 430 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).

-Film thickness of light emitting layer The film thickness of the light emitting layer 5 in the organic EL element 1 of 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 most preferably 10 nm or more and 50 nm or less. When it is 5 nm or more, it is easy to form a light emitting layer and adjust the chromaticity, and when it is 50 nm or less, an increase in the driving voltage is likely to be suppressed.

-Compound content in the light emitting layer The content of the first compound and the second compound contained in the light emitting layer 5 is preferably in the following range, for example.
The content of the first 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 preferably 20% by mass or more and 60% by mass or less. More preferred.
The content of the second 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. It is more preferably% or less.
The present embodiment does not exclude that the light emitting layer 5 contains materials other than the first compound and the second compound.
The light emitting layer 5 may contain only one type of the first compound, or may contain two or more types. The light emitting layer 5 may contain only one type of the second compound, or may contain two or more types.

・ TADF mechanism (mechanism)
FIG. 4 is a diagram showing an example of the relationship between the energy levels of the first compound and the second compound in the light emitting layer. In FIG. 4, S0 represents the ground state. S1 (Mat1) represents the lowest excited singlet state of the first compound. T1 (Mat1) represents the lowest excited triplet state of the first compound. S1 (Mat2) represents the lowest excited singlet state of the second compound. T1 (Mat2) represents the lowest excited triplet state of the second compound.
The dashed arrow from S1 (Mat1) to S1 (Mat2) in FIG. 4 represents the Felster-type energy transfer from the lowest excited singlet state of the first compound to the second compound.
As shown in FIG. 4, when a compound having a small ΔST (Mat1) is used as the first compound, the lowest excited triplet state T1 (Mat1) is inverted to the lowest excited singlet state S1 (Mat1) by thermal energy. Intersystem crossing is possible. Then, Felster-type energy transfer from the lowest excited singlet state S1 (Mat1) of the first compound to the second compound occurs, and the lowest excited singlet state S1 (Mat2) is generated. As a result, fluorescence emission from the lowest excited singlet state S1 (Mat2) of the second compound can be observed. It is believed that the internal efficiency can theoretically be increased to 100% by utilizing the delayed fluorescence by this TADF mechanism.

The organic EL element 1 according to the third embodiment has the compound of the first embodiment as the first compound (at least one of the compounds represented by any of the general formulas (1) to (3)) on the light emitting layer 5. ) And a second compound that has a smaller singlet energy than the first compound.
The organic EL element 1 according to the third embodiment can be used for electronic devices such as a display device and a light emitting device.

The configuration of the organic EL element 1 will be further described. Hereinafter, the description of the reference numeral may be omitted.

(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. Moreover, you may use a flexible substrate. The flexible substrate is a foldable (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 1% by mass or more and 10% by mass or less of zinc oxide is added 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 electrode. , Possible electrode materials (eg, 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), magnesium (Mg), calcium (Ca) and strontium ( Alkaline earth metals such as Sr), rare earth metals such as alloys containing them (for example, MgAg, AlLi), europium (Eu) and ytterbium (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 cathode materials 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 cesium (Cs), magnesium (Mg), and calcium (Ca). And alkaline earth metals such as strontium (Sr), and alloys containing them (eg, MgAg, AlLi), rare earth metals such as europium (Eu) and itterbium (Yb), and alloys containing them.

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 using various conductive materials such as indium tin oxide containing Al, Ag, ITO, graphene, silicon or silicon oxide, regardless of the size of the work function. 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, silver oxide, etc. Tungsten oxide, manganese oxide and the like can be used.

Further, as a substance having high hole injection property, a low molecular weight organic compound 4,4', 4''-tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4,4' , 4''-Tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA), 4,4'-bis [N- (4-diphenylaminophenyl) -N-phenyl Amino] biphenyl (abbreviation: DPAB), 4,4'-bis (N- {4- [N'-(3-methylphenyl) -N'-phenylamino] phenyl} -N-phenylamino) biphenyl (abbreviation: 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 a 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) methacrylamide] (abbreviation: PTPDMA), poly [N, N'-bis (4-butylphenyl) -N, N'-bis (phenyl) benzidine] (abbreviation: Polymer compounds such as Poly-TPD) can be mentioned. Further, a polymer compound to which an acid such as poly (3,4-ethylenedioxythiophene) / poly (styrene sulfonic acid) (PEDOT / PSS) or 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 [N- (Spiro-9,9'-bifluoren-2-yl) -N-phenylamino] Aromatic amine compounds such as 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 HT-2 used in the examples described later.

(Electronic transport layer)
The electron transport layer is a layer containing a substance having a high electron transport property. The electron transport layer includes 1) metal complexes such as aluminum complexes, beryllium complexes and zinc complexes, 2) complex aromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives and phenanthroline derivatives, and 3) polymer compounds. Can be used. Specifically, as low-molecular-weight organic compounds, Alq, tris (4-methyl-8-quinolinolato) 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- (Phenyl-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), vasofenantrolin (abbreviation: BPhen), vasocuproin (abbreviation: BCP), 4,4'-bis (5-methylbenzoxadiazole-2-yl) stillben (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 higher electron transport property than hole transport property. Further, the electron transport layer may be composed of a single layer, or may be composed of two or more layers made of the above substances laminated.

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.

(Electronic 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. Alkaline metals such as, alkaline earth metals, or compounds thereof can be used. In addition, a substance having electron transportability containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a substance containing magnesium (Mg) in Alq or the like may be used. In this case, electron injection from the cathode can be performed more efficiently.

Alternatively, a composite material 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 injection property and electron transport property because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material excellent in transporting generated electrons, and specifically, for example, a substance (metal complex, complex aromatic compound, etc.) constituting the above-mentioned electron transport layer is used. be able to. The electron donor may be any substance that exhibits electron donor 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. A Lewis base such as magnesium oxide can also be used. 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 deposition method, sputtering method, plasma method, ion plating method, and spin coating. 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.

(Film thickness)
The film thickness of each organic layer of the organic EL device 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 it 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.

[Fourth Embodiment]
The configuration of the organic EL element according to the fourth embodiment will be described. In the description of the fourth embodiment, the same components as those of the third embodiment are given the same reference numerals and names, and the description is omitted or simplified. Further, in the fourth embodiment, the same materials and compounds as those described in the third embodiment can be used for the materials and compounds not particularly mentioned.

The organic EL device according to the fourth embodiment is different from the organic EL device according to the third embodiment in that the light emitting layer further contains the third compound. Other points are the same as those in the third embodiment.
That is, in the fourth embodiment, the light emitting layer as the first organic layer contains the first compound, the second compound, and the third compound.
In this embodiment, the first compound is preferably a host material, the second compound is preferably a dopant material, and the third compound is a dispersant with a dopant material in the light emitting layer. It is preferably a material to be dispersed.

<Third compound>
The third compound may be a delayed fluorescence compound or a compound that does not exhibit delayed fluorescence.

The third compound is not particularly limited, but is preferably a compound other than the amine compound. Further, for example, as the third compound, a carbazole derivative, a dibenzofuran derivative, and a dibenzothiophene derivative can be used, but the third compound is not limited to these derivatives.

The third compound has a partial structure represented by the following general formula (31), a partial structure represented by the following general formula (32), and a partial structure represented by the following general formula (33) in one molecule. It is also preferable that the compound contains at least one of the partial structures represented by the following general formula (34).

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

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

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

The partial structure represented by the general formula (31) is at least one group selected from the group consisting of the group represented by the following general formula (33) and the group represented by the following general formula (34). It is preferable that it is contained in the third compound.
It is also preferable that the third compound has at least one of the partial structures represented by the following general formula (33) and the following general formula (34). Since the bonding sites are located at the meta positions of each other as in the partial structures represented by the following general formula (33) and the following general formula (34), the energy gap T _77K (Mat3) in 77 [K] of the third compound. ) Can be kept high.

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

In the general formula (33), Y ₃₁ , Y ₃₂ , Y ₃₄ , and Y ₃₆ are preferably CR ₃₁ independently, and a plurality of R ₃₁ are the same as or different from each other.
Further, in the general formula (34), it is preferable that Y ₃₂ , Y ₃₄ , and Y ₃₆ are independently CR ₃₁ , and a plurality of R _31s are the same as or different from each other.

The substituted germanium group is preferably represented by −Ge (R ₃₀₁ ) ₃ . R ₃₀₁ is a substituent independently of each other. The substituent R ₃₀₁ is preferably a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms. A plurality of R _301s are the same as or different from each other.

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

In the general formula (35), Y _{41 to} Y ₄₈ are independently nitrogen atoms or CR ₃₂ , respectively.
In the general formulas (36) and (37), Y _{41 to} Y ₄₅ , Y ₄₇ , and Y ₄₈ are independently nitrogen atoms or CR ₃₂ , respectively.
In the general formula (38), Y ₄₁ , Y ₄₂ , Y ₄₄ , Y ₄₅ , Y ₄₇ , and Y ₄₈ are independently nitrogen atoms or CR ₃₂ , respectively.
In the general formula (39), Y _{42 to} Y ₄₈ are independently nitrogen atoms or CR ₃₂ , respectively.
In the general formula (30a), Y _{42 to} Y ₄₇ are independently nitrogen atoms or CR ₃₂ , respectively.
In the general formulas (35) to (39) and (30a),
R ₃₂ is an independent hydrogen atom or substituent, respectively.
R ₃₂ as a substituent is
Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,
A heteroaryl group having 5 to 30 substituted or unsubstituted ring-forming atoms,
Substituent or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substituted or unsubstituted fluoroalkyl groups having 1 to 30 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl groups having 3 to 30 carbon atoms,
Substituent or unsubstituted aralkyl groups having 7 to 30 carbon atoms,
Substituted or unsubstituted silyl group,
Substitute germanium group,
Substituted phosphine oxide group,
Halogen atom,
Cyano group,
Selected from the group consisting of nitro groups and substituted or unsubstituted carboxy groups,
A plurality of R _32s are the same as or different from each other.
In the general formulas (37) to (39) and (30a),
X ₃₀ is an NR ₃₃ , an oxygen atom, or a sulfur atom,
R ₃₃ is
Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,
A heteroaryl group having 5 to 30 substituted or unsubstituted ring-forming atoms,
Substituent or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substituted or unsubstituted fluoroalkyl groups having 1 to 30 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl groups having 3 to 30 carbon atoms,
Substituent or unsubstituted aralkyl groups having 7 to 30 carbon atoms,
Substituted or unsubstituted silyl group,
Substitute germanium group,
Substituted phosphine oxide group,
Fluorine atom,
Cyano group,
Selected from the group consisting of nitro groups and substituted or unsubstituted carboxy groups,
The plurality of R _33s are the same as or different from each other.
However, the substituted or unsubstituted aryl group having 6 to 30 carbon atoms in R ₃₃ is preferably a non-condensed ring.
In the general formulas (35) to (39) and (30a), * independently represents a bond with another atom or other structure in the molecule of the third compound.

In the general formula (35), Y _{41 to} Y ₄₈ are preferably CR ₃₂ independently of each other, and in the general formula (36) and the general formula (37), Y _{41 to} Y ₄₅ , Y. It is preferable that ₄₇ and Y ₄₈ are independently CR ₃₂ , and in the general formula (38), Y ₄₁ , Y ₄₂ , Y ₄₄ , Y ₄₅ , Y ₄₇ , and Y ₄₈ are independent of each other. , CR ₃₂ , and in the general formula (39), Y _{42 to} Y ₄₈ are each independently, preferably CR ₃₂ , and in the general formula (30a), Y _{42 to} Y ₄₇ are , Each independently, preferably CR ₃₂ , and the plurality of R _32s are the same as or different from each other.

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

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

The third compound is also preferably an aromatic hydrocarbon compound or an aromatic heterocyclic compound.

-Method for producing the third compound The third compound can be produced, for example, by the methods described in International Publication No. 2012/153780, International Publication No. 2013/038650, and the like. Further, for example, a third compound can be produced by using a known alternative reaction according to the target substance and a raw material.

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

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

Specific examples of the heteroaryl group (sometimes referred to as a heterocyclic group, a heteroaromatic ring group, or an aromatic heterocyclic group) include a pyrrolyl group, a pyrazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridadinyl group, and a pyridyl group. , Triazinyl group, indolyl group, isoindrill group, imidazolyl group, benzimidazolyl group, indazolyl group, imidazole [1,2-a] pyridinyl group, furyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, azadibenzo Furanyl group, thiophenyl group, benzothienyl group, dibenzothienyl group, azadibenzothienyl group, quinolyl group, isoquinolyl group, quinoxalinyl group, quinazolinyl group, naphthyldinyl group, carbazolyl group, azacarbazolyl group, phenanthridinyl group, acridinyl group, Phenanthrolinyl group, phenazinyl group, phenothiazinyl group, phenoxadinyl group, oxazolyl group, oxadiazolyl group, frazayl group, benzoxazolyl group, thienyl group, thiazolyl group, thiadiazolyl group, benzthiazolyl group, triazolyl group, tetrazolyl group, etc. Examples thereof include a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, an azadibenzofuranyl group, and an azadibenzothienyl group.
As the heteroaryl group, a dibenzofuranyl group, a dibenzothienyl group, a carbazolyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, an azadibenzofuranyl group, or an azadibenzothienyl group is preferable, and a dibenzofranyl group, a dibenzothienyl group, Azadibenzofuranyl groups or azadibenzothienyl groups are more preferred.

In the third compound, the substituted silyl group may also be selected from the group consisting of substituted or unsubstituted trialkylsilyl groups, substituted or unsubstituted arylalkylsilyl groups, and substituted or unsubstituted triarylsilyl groups. preferable.
Specific examples of the substituted or unsubstituted trialkylsilyl group include a trimethylsilyl group and a triethylsilyl group.
Specific examples of the substituted or unsubstituted arylalkylsilyl group include a diphenylmethylsilyl group, a ditrilmethylsilyl group, a phenyldimethylsilyl group and the like.
Specific examples of the substituted or unsubstituted triarylsilyl group include a triphenylsilyl group and a tritrylsilyl group.

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

In the third compound, examples of the substituted carboxy group include a benzoyloxy group and the like.

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

<Relationship between the first compound, the second compound, and the third compound in the light emitting layer>
In the organic EL device of the present embodiment, the singlet energy S _{1 (Mat1)} of the first compound, the singlet energy S ₁ of the third compound _(MAT3), satisfies the following equation (Equation 2) Is preferable.
_{S 1 (Mat3)> S 1} (Mat1) ( number 2)

The energy gap T _77K (Mat3) at 77 [K] of the third compound is preferably larger than the energy gap T _77K (Mat1) at 77 [K] of the first compound.
The energy gap T _77K (Mat3) at 77 [K] of the third compound is preferably larger than the energy gap T _77K (Mat2) at 77 [K] of the second compound.

The singlet energy _S 1 (Mat1) of the first compound, a singlet energy _S 1 (Mat2) of the second compound, a singlet energy _S 1 of the third compound (MAT3), the following equation (Equation It is preferable to satisfy the relationship of 2A).
S ₁ (Mat 3)> S ₁ (Mat ₁ )> S ₁ (Mat 2) ... (Equation 2A)

An energy gap _T 77K (Mat1) in 77 [K] of the first compound, an energy gap _T 77K (Mat2) in 77 [K] of the second compound, the energy gap in the 77 [K] of the third compound It is preferable that the relationship with T _77K (Mat3) is satisfied by the following mathematical formula (Equation 2B).
T _77K (Mat3)> T _77K (Mat1)> T _77K (Mat2) ... (Equation 2B)

When the organic EL element of the present embodiment is made to emit light, it is preferable that a fluorescent compound mainly emits light in the light emitting layer.
The organic EL element of the present embodiment preferably emits red light or green light, like the organic EL element of the third embodiment.
The main peak wavelength of the light emitted from the organic EL element can be measured by the same method as that of the organic EL element of the third embodiment.

-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 content of the first 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. preferable.
The content of the second 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. It is more preferably% or less.
The content of the third compound is preferably 10% by mass or more and 80% by mass or less.
The upper limit of the total content of the first compound, the second compound, and the 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 type of the first compound, or may contain two or more types. The light emitting layer may contain only one type of the second compound, or may contain two or more types. The light emitting layer may contain only one type of the third compound, or may contain two or more types.

FIG. 5 is a diagram showing an example of the relationship between the energy levels of the first compound, the second compound, and the third compound in the light emitting layer. In FIG. 5, S0 represents the ground state. S1 (Mat1) represents the lowest excited singlet state of the first compound, and T1 (Mat1) represents the lowest excited triplet state of the first compound. S1 (Mat2) represents the lowest excited singlet state of the second compound, and T1 (Mat2) represents the lowest excited triplet state of the second compound. S1 (Mat3) represents the lowest excited singlet state of the third compound, and T1 (Mat3) represents the lowest excited triplet state of the third compound. The dashed arrow from S1 (Mat1) to S1 (Mat2) in FIG. 5 represents the Felster-type energy transfer from the lowest excited singlet state of the first compound to the lowest excited singlet state of the second compound. ..
As shown in FIG. 5, when a compound having a small ΔST (Mat1) is used as the first compound, the lowest excited triplet state T1 (Mat1) is inverted to the lowest excited singlet state S1 (Mat1) by thermal energy. Intersystem crossing is possible. Then, Felster-type energy transfer from the lowest excited singlet state S1 (Mat1) of the first compound to the second compound occurs, and the lowest excited singlet state S1 (Mat2) is generated. As a result, fluorescence emission from the lowest excited singlet state S1 (Mat2) of the second compound can be observed. It is believed that the internal quantum efficiency can theoretically be increased to 100% by utilizing the delayed fluorescence by this TADF mechanism.

The organic EL element according to the fourth embodiment has a compound of the first embodiment as the first compound (at least one of the compounds represented by any of the general formulas (1) to (3)) in the light emitting layer. And a second compound having a lower singlet energy than the first compound, and a third compound having a higher singlet energy than the first compound.
According to the fourth embodiment, an organic EL element having excellent performance can be realized.
The organic EL element according to the fourth embodiment can be used for electronic devices such as display devices and light emitting devices.

[Fifth Embodiment]
The configuration of the organic EL element according to the fifth embodiment will be described. In the description of the fifth embodiment, the same components as those of the third embodiment and the fourth embodiment are given the same reference numerals and names, and the description thereof will be omitted or simplified. Further, in the fifth embodiment, with respect to the materials and compounds not particularly mentioned, the same materials and compounds as those described in the third embodiment and the fourth embodiment can be used.

The organic EL device according to the fifth embodiment is different from the organic EL device according to the third embodiment in that the light emitting layer contains the fourth compound instead of the second compound. Other points are the same as those in the third embodiment.
In a fifth embodiment, the light emitting layer comprises a first compound and a fourth compound.
In this embodiment, the first compound is preferably a dopant material (sometimes referred to as a guest material, emitter, luminescent material) and the fourth compound is sometimes referred to as a host material (sometimes referred to as a matrix material). .) Is preferable.
The fourth compound may be a delayed fluorescence compound or a compound that does not exhibit delayed fluorescence.
The fourth compound is not particularly limited, but for example, the third compound described in the section of the fourth embodiment can be used.

<Relationship between the first compound and the fourth compound in the light emitting layer>
In the organic EL device 1 of the present embodiment, the singlet energy _S 1 (Mat1) of the first compound, a singlet energy _S 1 of the fourth compound (MAT4), but the relationship of the following equation (Equation 4) It is preferable to satisfy.
_{S 1 (Mat4)> S 1} (Mat1) ( number 4)

The energy gap T _77K (Mat4) at 77 [K] of the fourth compound is preferably larger than the energy gap T _77K (Mat1) at 77 [K] of the first compound. That is, it is preferable to satisfy the relationship of the following mathematical formula (Equation 4A).
T _77K (Mat4)> T _77K (Mat1) ... (Equation 4A)

When the organic EL device of the present embodiment is made to emit light, it is preferable that the first compound mainly emits light in the light emitting layer.

-Compound content in the light emitting layer The content of the first compound and the fourth compound contained in the light emitting layer is preferably in the following range, for example.
The content of the first 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 preferably 20% by mass or more and 60% by mass or less. More preferred.
The content of the fourth compound is preferably 20% by mass or more and 90% by mass or less, more preferably 40% by mass or more and 90% by mass or less, and preferably 40% by mass or more and 80% by mass or less. More preferred.
The present embodiment does not exclude that the light emitting layer contains materials other than the first compound and the fourth compound.
The light emitting layer may contain only one type of the first compound, or may contain two or more types. The light emitting layer may contain only one kind of the fourth compound, or may contain two or more kinds.

FIG. 6 is a diagram showing an example of the relationship between the energy levels of the first compound and the fourth compound in the light emitting layer. In FIG. 6, S0 represents the ground state. S1 (Mat1) represents the lowest excited singlet state of the first compound, and T1 (Mat1) represents the lowest excited triplet state of the first compound. S1 (Mat4) represents the lowest excited singlet state of the fourth compound, and T1 (Mat4) represents the lowest excited triplet state of the fourth compound. The dashed arrow in FIG. 6 represents the energy transfer between each excited state. Felster transfer from the lowest excited singlet state S1 of the fourth compound, or Dexter transfer from the lowest excited triplet state T1, brings the first compound into the lowest excited singlet state S1 or the lowest excited triplet state T1. Each energy moves. Furthermore, when a small material with ΔST (Mat1) is used as the first compound, the lowest excited triplet state T1 of the first compound can be intersystem crossed with the lowest excited singlet state S1 by thermal energy. .. As a result, fluorescence emission from the lowest excited singlet state S1 of the first compound can be observed. It is believed that the internal efficiency can theoretically be increased to 100% by utilizing the delayed fluorescence by this TADF mechanism.

The organic EL element according to the fifth embodiment has a compound of the first embodiment as the first compound (at least one of the compounds represented by any of the general formulas (1) to (3)) in the light emitting layer. And a fourth compound, which has a higher singlet energy than the first compound.
According to the fifth embodiment, an organic EL device having excellent performance can be realized.
The organic EL element according to the fifth embodiment can be used for electronic devices such as display devices and light emitting devices.

[Sixth 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 the electronic device include a display device and a light emitting device. Examples of the display device include display components (for example, organic EL panel modules, etc.), televisions, mobile phones, tablets, personal computers, and the like. Examples of the light emitting device include lighting and vehicle lighting equipment.

[Modification of Embodiment]
The present invention is not limited to the above-described embodiment, and changes, improvements, etc. within the range in which 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 fluorescence light emitting layer or a phosphorescent light emitting layer utilizing light emission by electronic transition from a triplet excited state to a 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 located in contact with the light emitting layer to block at least one of holes, electrons, and excitons.
For example, when a barrier layer is arranged in contact with the cathode side of the light emitting layer, the barrier layer transports electrons and holes reach a layer on the cathode side of the barrier layer (for example, an electron transport layer). Stop doing. When the organic EL element includes an electron transporting layer, it is preferable to include the barrier layer between the light emitting layer and the electron transporting 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.

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. To 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.
There is no particular restriction on the divalent linking group, _{e.g., -O -, - CO -,} - CO 2 -, - S -, - SO -, - SO 2 -, - NH -, - NRa-, and their Examples thereof include a group in which two or more connecting 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 the "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). In the molecular structure represented by the general formula (H1), the atom contained in Rx ₁ and the atom contained in Ry ₁ form the ring H 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 structures represented by the general formulas (E2) to (I2), E to I each represent a ring structure (the ring having 5 or more ring-forming atoms). In the general formulas (E2) to (I2), * 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) correspond independently to the two * in the general formula (E2) and the general formula (E1), 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 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.

In the present specification, the ring-forming carbon number 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 ring-forming carbon number. The "ring-forming carbon number" described below shall be the same unless otherwise specified. For example, a benzene ring has 6 ring-forming carbon atoms, a naphthalene ring has 10 ring-forming carbon atoms, a pyridinyl group has 5 ring-forming carbon atoms, and a flanyl 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 refers to 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 included 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 quinazoline ring and atoms constituting substituents 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 (Explanation of each substituent)
The aryl group (sometimes referred to as an aromatic hydrocarbon group) in the present specification is, for example, an aryl group Sub ₁ , and the aryl group Sub ₁ is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, or anthryl. Group, phenanthryl group, fluorenyl group, pyrenyl group, chrysenyl group, fluoranthenyl group, benzo [a] anthryl group, benzo [c] phenanthryl group, triphenylenyl group, benzo [k] fluoranthenyl group, benzo [g] chrysenyl It is at least one group selected from the group consisting of a group, a benzo [b] triphenylenyl group, a pisenyl group, and a perylenyl group.

As the aryl group Sub ₁ in the present specification, the number of ring-forming carbon atoms is preferably 6 to 30, more preferably 6 to 20, further preferably 6 to 14, and 6 to 12. It is even more preferable to have. 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 with the substituted or unsubstituted alkyl group Sub ₃ described later, 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.

The heterocyclic group Sub ₂ in the present specification is, for example, pyridyl group, pyrimidinyl group, pyrazinyl group, pyridadinyl group, triazinyl group, quinolyl group, isoquinolinyl group, naphthyldinyl group, phthalazinyl group, quinoxalinyl group, quinazolinyl group, phenanthridinyl. Group, acridinyl group, phenanthrolinyl group, pyrrolyl group, imidazolyl group, pyrazolyl group, triazolyl group, tetrazolyl group, indrill group, benzimidazolyl group, indazolyl group, imidazolylinyl 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 A group consisting of an azolyl group, a benzoxaziazolyl group, a benzothiasiazolyl group, a dibenzofuranyl group, a dibenzothienyl group, a piperidinyl group, a pyrrolidinyl group, a piperazinyl group, a morpholic group, a phenazinyl group, a phenothiazinyl group, and a phenoxadinyl group. At least one of the groups selected from.

As the heterocyclic group Sub ₂ in the present specification, the number of ring-forming atoms is preferably 5 to 30, more preferably 5 to 20, and even more preferably 5 to 14. Among the above heterocyclic groups Sub ₂ , 1-dibenzofuranyl group, 2-dibenzofuranyl group, 3-dibenzofuranyl group, 4-dibenzofuranyl group, 1-dibenzothienyl group, 2-dibenzothienyl group, 3- Even more preferred are dibenzothienyl groups, 4-dibenzothienyl groups, 1-carbazolyl groups, 2-carbazolyl groups, 3-carbazolyl groups, 4-carbazolyl groups, and 9-carbazolyl groups. 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 heterocycle. 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 Formula (XY-1) ~ (XY -18), it is _{X A} and _{Y A,} independently, a heteroatom, an oxygen atom, a sulfur atom, a selenium atom, silicon atom or germanium atom, 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 joint can be changed as appropriate.

The alkyl group in the present specification may be either a straight chain alkyl group, a branched chain alkyl group or a cyclic alkyl group.
The alkyl group in the present specification is, for example, the alkyl group Sub ₃ .
The linear alkyl group in the present specification 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, the cyclic alkyl 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 alkyl group Sub ₃₂ 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, a t-butyl group. , N-Pentyl group, n-Hexyl group, n-Heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group , N-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, amyl group, isoamyl group, 1-methylpentyl group, 2-methylpentyl group, 1-pentylhexyl group, 1- At least one group selected from the group consisting of a butylpentyl group, a 1-heptyloctyl group, and a 3-methylpentyl group.

The linear alkyl group Sub ₃₁ or the branched alkyl group Sub _{32 in} the present specification preferably has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and preferably 1 to 10 carbon atoms. More preferably, it is even more preferably 1 to 6. The linear alkyl group Sub ₃₁ or the branched alkyl group Sub ₃₂ includes methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t-butyl group and n. -Pentyl groups, n-hexyl groups, amyl groups, isoamyl groups, and neopentyl groups are even more preferred.

The cyclic alkyl group Sub ₃₃ in the present specification is, for example, a cycloalkyl group Sub ₃₃₁ .

The cycloalkyl group Sub ₃₃₁ in the present specification 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. The ring-forming carbon number of the cycloalkyl group Sub ₃₃₁ is preferably 3 to 30, more preferably 3 to 20, further preferably 3 to 10, and even more preferably 5 to 8. preferable. Among the cycloalkyl groups Sub ₃₃₁ , 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, the alkylsilyl group Sub ₅₁ and the arylsilyl group Sub ₅₂ . It is a group.

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. 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 dialkylarylsilyl group Sub ₅₂₁ preferably has 8 to 30 carbon atoms.

The alkyldiarylsilyl group Sub ₅₂₂ is, for example, an alkyldiarylsilyl group having one alkyl group Sub ₃ and two aryl group 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 number of carbon atoms of the triarylsilyl group Sub ₅₂₃ is preferably 18 to 30.

A substituted or unsubstituted alkylsulfonyl groups herein, for example, an alkylsulfonyl group Sub _6, an alkylsulfonyl group Sub ₆ is represented by _-SO 2 _{R w. R w} in -SO ₂ R _w represents the 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 aryl group Sub ₁ and the 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 by −Z ₃ −Z ₄ . The Z ₃ is, for example, an alkylene group corresponding to the above 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). 10, more preferably 1 to 6). The aralkyl group Sub ₇ includes, for example, a benzyl group, a 2-phenylpropan-2-yl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, and 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 It is at least one group selected from the group consisting of a-naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 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 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 alkoxy group Sub ₈ preferably has 1 to 30 carbon atoms, and more preferably 1 to 20 carbon atoms.

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 above-mentioned alkoxy group Sub ₈ is replaced 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 includes 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 by −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 . Is the basis.
The arylamino group Sub ₁₁₁ is represented as -NHR _V1 or -N (R _V1 ) ₂ . This R _V1 is, for example, the aryl group Sub ₁ . -N _{(R V1)} 2 two _{R V1} in _2, 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 . -N _{(R V2)} of two of the _{2 R V2} 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 a linear or branched chain, eg, a vinyl group, a propenyl group, a butenyl group, an oleyl group, an eikosa. At least one selected from the group consisting of pentaenyl group, docosahexaenyl group, styryl group, 2,2-diphenylvinyl group, 1,2,2-triphenylvinyl group, and 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 R _V3 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 R _V4 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 in the present specification 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 in the present specification 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 . The acyl group Sub ₁₈ in the present specification 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 substituent 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.
Alkyl ester groups herein, for example, an alkyl ester group _{Sub 201,} an alkyl ester group _{Sub 201} is represented by -C (= O) OR ^{E. RE} is, for example, the above-mentioned aryl group Sub ₃ which is 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 trimethylsyloxanyl group.

The carbamoyl group in the present specification is represented by -CONH ₂ .
The substituted carbamoyl group in the present specification 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 above-mentioned alkyl group Sub ₃ (preferably having 1 to 6 carbon atoms) substituted or unsubstituted.

As used herein, the term "ring-forming carbon" means a carbon atom that constitutes a saturated ring, an unsaturated ring, or an aromatic ring. "Ring-forming atom" means a carbon atom and a hetero atom constituting a hetero ring (including a saturated ring, an unsaturated ring, and an aromatic ring).

Further, in the present specification, the hydrogen atom includes isotopes having different numbers of neutrons, that is, hydrogen (Protium), deuterium (Deuterium), and tritium (Tritium).

Hereinafter, the alkyl group Sub ₃ refers to any one or more of the linear alkyl group Sub ₃₁ , the branched chain alkyl group Sub ₃₂ , and the cyclic alkyl group Sub ₃₃ described in "Explanation of each substituent". means.
Similarly, the substituted silyl group Sub ₅ means any one or more groups 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 R _F1 , and the substituent R _F1 is an aryl group Sub ₁ , a heteroaryl group Sub ₂ , an alkyl group Sub ₃ , and the like. Alkyl halide 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, an alkynyl group _{Sub 13,} an alkylthio group _{Sub 14,} arylthio group _{Sub 15,} a substituted phosphino group _{Sub 16,} an arylcarbonyl group _{Sub 17,} acyl group _{Sub 18,} a substituted phosphoryl group _{Sub 19,} an ester group _{Sub 20,} siloxanyl 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 at least one group selected from the group consisting of a carboxy group.

In the present specification, substituents _{R F1} when the "substituted or unsubstituted" may be Jiariruhou containing group _{(Ar B1} Ar B2 B-). Examples of the Ar _B1 and Ar _B2 include the above-mentioned aryl group Sub ₁ . _{Ar B1} Ar _B2 B- Ar _B1 and _{Ar B2} in the same or different.

Specific examples and preferred groups of substituents _{R F1,} substituent in "Description of the substituent" (e.g., aryl group Sub _1, heteroaryl Sub _2, alkyl group Sub _3, a halogenated alkyl 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 , and siloxanyl group Sub ₂₁ and carbamoyl group Sub ₂₂ ). Specific examples of the above and groups similar to the preferred groups are mentioned.

Substituents R _F1 in the case of "substituted or unsubstituted" are aryl group Sub ₁ , heteroaryl group Sub ₂ , alkyl group Sub ₃ , halogenated alkyl 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 , siloxanyl group Sub ₂₁ , carbamoyl group Sub ₂₂ , unsubstituted amino group, unsubstituted silyl group, halogen atom, cyano group, hydroxy group, nitro group, and at least one group selected from the group consisting of carboxyl group (hereinafter, also referred to as substituent R _F2) may be further substituted by. Further, a plurality of these substituents _RF2 may be bonded to each other to form a ring.

Not substituted with the substituents R _F1 is a "unsubstituted" in the case of "substituted or unsubstituted" means that a hydrogen atom is bonded.

In the present specification, the "carbon number XX to YY" in the expression "ZZ group having substituted or unsubstituted carbon number XX to YY" represents the carbon number when the ZZ group is unsubstituted and is substituted. and carbon number of the substituent R _F1 where are is not included.

In the present specification, the "atomic number XX to YY" in the expression "ZZ group of atomic number XX to YY substituted or unsubstituted" represents the number of atoms when the ZZ group is unsubstituted and is substituted. atoms of the substituents R _F1 in this case is not included.

The same applies to the case of "substituted 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.

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

The compounds of Examples were prepared as follows.

[Example 1]
(1) Synthesis Example 1: Synthesis of compound 1 (1-1) Synthesis of intermediate A

In a nitrogen atmosphere, in a 500 mL three-necked flask, carbazole (5.0 g, 30 mmol), potassium carbonate (6.2 g, 45 mmol), 4-Bromo-2,6-difluorobenzonirile (6.5 g, 30 mmol) and N, N- 300 mL of dimethylformamide was added. After heating and stirring at 25 ° C. for 4 hours, the temperature was returned to room temperature (25 ° C.), 100 mL of water was added, and the precipitated solid was purified by silica gel column chromatography. 6.2 g of white solid was obtained. It was identified as Intermediate A by ASAP-MS (Atmosphere Pressure Solid Analysis Probe Mass Spectrometry) (yield 57%).

(1-2) Synthesis of intermediate B

Under a nitrogen atmosphere, in a 200 mL three-necked flask, 7H-Benzofluo [2,3-b] carbazole (1.1 g, 4.4 mmol), potassium carbonate (1.1 g, 8 mmol), intermediate A (1.5 g, 4 mmol). ) And 100 mL of N, N-dimethylformamide were added. After heating and stirring at 100 ° C. for 4 hours, the temperature was returned to room temperature (25 ° C.), 50 mL of water was added, and the precipitated solid was purified by silica gel column chromatography. 2.30 g of white solid was obtained. It was identified as Intermediate B by ASAP-MS (yield 95%).

(1-3) Synthesis of compound 1

Intermediate B (2.0 g, 3.3 mmol), zinc cyanide (2.3 g, 16 mmol), tetrakistriphenylphosphine palladium (0) (0.23 g, 0.20 mmol) in a 100 mL three-necked flask under a nitrogen atmosphere. ), And 30 mL of N-methyl-2-pyrrolidone were added. After heating and stirring at 130 ° C. for 4 hours, the temperature was returned to room temperature (25 ° C.), and aqueous ammonia (20 mL, 30% by mass) was added to the reaction solution. The precipitated solid was purified by silica gel column chromatography to obtain 1.4 g of a yellow solid. It was identified as Compound 1 by analysis of ASAP-MS (yield 80%).

[Example 2]
(2) Synthesis Example 2: Synthesis of compound 2 (2-1) Synthesis of intermediate C

4-Bromodibenzothiophene (26.0 g, 100 mmol), 2-chloro-4-methylaniline (17 g, 120 mmol), tris (dibenzylideneacetone) dipalladium (0) (Pd ₂ ) in a 1 L three-necked flask under a nitrogen atmosphere. dba ₃ ) (0.9 g, 1 mmol), tri-tert-butylphosphonium tetrafluoroborate (P (t-Bu) ₃ HBF ₄ ) (2.3 g, 8 mmol), sodium tert-butoxide (11.5 g, 120 mmol) ) And 350 mL of toluene were added, and the mixture was heated and stirred at 60 ° C. for 7 hours and then cooled to room temperature (25 ° C.). The reaction solution was purified by silica gel column chromatography to obtain 26 g of a white solid. It was identified as intermediate C by analysis of GC-MS (Gas Chromatograph Mass Spectrometer) (yield 80%).

(2-2) Synthesis of intermediate D

Intermediate C (26.0 g, 80 mmol), 1,3-bis (2,6-diisopropylphenyl) imidazolium chloride (IPrHCl) (1.4 g, 3.2 mmol), in a 1 L three-necked flask under a nitrogen atmosphere. Palladium (II) acetate (0.9 g, 1.6 mmol), potassium carbonate (22.0 g, 160 mmol), and 400 mL of N, N-dimethylacetamide (DMAc) were added, and the mixture was stirred at 130 ° C. for 7 hours and then at room temperature (25). ℃). The reaction solution was purified by silica gel column chromatography to obtain 21 g of a white solid. It was identified as Intermediate D by GC-MS analysis (yield 91%).

(2-3) Synthesis of intermediate E

Intermediate D (1.3 g, 4.4 mmol), potassium carbonate (1.1 g, 8 mmol), intermediate A (1.5 g, 4 mmol) and N, N-dimethylformamide in a 200 mL three-necked flask under a nitrogen atmosphere. Was added in 100 mL. After heating and stirring at 100 ° C. for 4 hours, the temperature was returned to room temperature (25 ° C.), 50 mL of water was added, and the precipitated solid was purified by silica gel column chromatography. 2.2 g of a yellow solid was obtained. It was identified as Intermediate E by ASAP-MS (yield 88%).

(2-4) Synthesis of compound 2

Intermediate E (2.0 g, 3.2 mmol), zinc cyanide (2.3 g, 16 mmol), tetrakistriphenylphosphine palladium (0) (0.23 g, 0.20 mmol) in a 100 mL three-necked flask under a nitrogen atmosphere. ), And 30 mL of N-methyl-2-pyrrolidone was added. After heating and stirring at 130 ° C. for 4 hours, the temperature was returned to room temperature (25 ° C.), and aqueous ammonia (20 mL, 30% by mass) was added to the reaction solution. The precipitated solid was purified by silica gel column chromatography to obtain 1.3 g of a yellow solid. It was identified as Compound 2 by analysis of ASAP-MS (yield 70%).

[Example 3]
(3) Synthesis Example 3: Synthesis of compound 3 (3-1) Synthesis of intermediate F

Under a nitrogen atmosphere, in a 200 mL three-necked flask, 7,7-Dimethyl-5,7-dihydroindeno [2,1-b] carbazole (1.2 g, 4.4 mmol), potassium carbonate (1.1 g, 8 mmol), intermediate Body A (1.5 g, 4 mmol) and 100 mL of N, N-dimethylformamide were added. After heating and stirring at 100 ° C. for 4 hours, the temperature was returned to room temperature (25 ° C.), 50 mL of water was added, and the precipitated solid was purified by silica gel column chromatography. 2.34 g of white solid was obtained. It was identified as Intermediate F by ASAP-MS (yield 93%).

(3-2) Synthesis of compound 3

Intermediate F (2.0 g, 3.2 mmol), zinc cyanide (2.3 g, 16 mmol), tetrakistriphenylphosphine palladium (0) (0.23 g, 0.20 mmol) in a 100 mL three-necked flask under a nitrogen atmosphere. ), And 30 mL of N-methyl-2-pyrrolidone were added. After heating and stirring at 130 ° C. for 4 hours, the temperature was returned to room temperature (25 ° C.), and aqueous ammonia (20 mL, 30% by mass) was added to the reaction solution. The precipitated solid was purified by silica gel column chromatography to obtain 1.5 g of a yellow solid. It was identified as compound 3 by analysis of ASAP-MS (yield 81%).

[Example 3]
(4) Synthesis Example 4: Synthesis of Compound 4 (4-1) Synthesis of Intermediate G

In a nitrogen atmosphere, in a 200 mL three-necked flask, 11,12-dihydro-11-phenylindro [2,3-a] carbazole (1.5 g, 4.4 mmol), potassium carbonate (1.1 g, 8 mmol), intermediate Body A (1.5 g, 4 mmol) and 100 mL of N, N-dimethylformamide were added. After heating and stirring at 100 ° C. for 4 hours, the temperature was returned to room temperature (25 ° C.), 50 mL of water was added, and the precipitated solid was purified by silica gel column chromatography. 2.1 g of yellow solid was obtained. It was identified as Intermediate G by ASAP-MS (yield 79%).

(4-2) Synthesis of compound 4

Intermediate G (2.0 g, 3.0 mmol), zinc cyanide (1.8 g, 15 mmol), tetrakistriphenylphosphine palladium (0) (0.23 g, 0.20 mmol) in a 100 mL three-necked flask under a nitrogen atmosphere. ), And 30 mL of N-methyl-2-pyrrolidone was added. After heating and stirring at 130 ° C. for 4 hours, the temperature was returned to room temperature (25 ° C.), and aqueous ammonia (20 mL, 30% by mass) was added to the reaction solution. The precipitated solid was purified by silica gel column chromatography to obtain 1.7 g of a yellow solid. It was identified as compound 4 by analysis of ASAP-MS (yield 93%).

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 (20)

A compound represented by any of the following general formulas (1) to (3).


(In the general formulas (1) to (3),
R ₁ is a group represented by any of the following general formulas (101) to (115) and (201) to (204).
R ₂ is a group represented by any of the following general formulas (101) to (115), (201) to (204) and the following general formula (X).
However, R ₁ and R ₂ are different from each other. )

(In the general formulas (101) to (115), R _{11 to} R ₂₀ are independent hydrogen atoms or substituents, and R ₃₁ and R ₃₂ are independent substituents.
R _{11 to} R ₂₀ as substituents are independent of each other.
Substituted or unsubstituted ring-forming aryl groups having 6 to 14 carbon atoms,
Substituted or unsubstituted heterocyclic groups having 5 to 14 ring-forming atoms,
Substituent or unsubstituted alkyl groups with 1 to 6 carbon atoms,
Substituent or unsubstituted alkoxy groups having 1 to 6 carbon atoms,
Substituent or unsubstituted alkylthio groups having 1 to 6 carbon atoms,
Substituent or unsubstituted ring-forming aryloxy groups having 6 to 14 carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming arylamino group having 6 to 14 carbon atoms.
R ₃₁ and R ₃₂ as substituents are independent of each other.
Substituted or unsubstituted ring-forming aryl groups having 6 to 14 carbon atoms,
Substituted or unsubstituted heterocyclic groups having 5 to 14 ring-forming atoms,
Substituent or unsubstituted alkyl groups with 1 to 6 carbon atoms,
It is a substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming aryloxy group having 6 to 14 carbon atoms. * Independently represent the binding site of the benzene ring with the carbon atom in the general formulas (1) to (3). )


(In the general formulas (201) to (204), R _{21 to} R ₃₀ are independently hydrogen atoms or substituents, and R ₃₃ is a substituent.
R _{21 to} R ₃₀ as substituents are independent of each other.
Substituted or unsubstituted ring-forming aryl groups having 6 to 14 carbon atoms,
Substituted or unsubstituted heterocyclic groups having 5 to 14 ring-forming atoms,
Substituent or unsubstituted alkyl groups with 1 to 6 carbon atoms,
Substituent or unsubstituted alkoxy groups having 1 to 6 carbon atoms,
Substituent or unsubstituted alkylthio groups having 1 to 6 carbon atoms,
Substituent or unsubstituted ring-forming aryloxy groups having 6 to 14 carbon atoms,
A substituted or unsubstituted alkylthio group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming arylamino group having 6 to 14 carbon atoms.
R ₃₃ as a substituent is
Substituted or unsubstituted ring-forming aryl groups having 6 to 14 carbon atoms,
Substituted or unsubstituted heterocyclic groups having 5 to 14 ring-forming atoms,
Substituent or unsubstituted alkyl groups with 1 to 6 carbon atoms,
A substituted or unsubstituted alkoxy group having 1 to 6 carbon atoms, or a substituted or unsubstituted ring-forming aryloxy group having 6 to 14 carbon atoms.
However, when R ₃₃ is a substituted aryl group having 6 to 14 carbon atoms, the substituent is not a cyano group. * Independently represent the binding site of the benzene ring with the carbon atom in the general formulas (1) to (3). )

(In the general formula (X), R _{161 to} R ₁₆₈ are independently hydrogen atoms or substituents, and R _{161 to} R ₁₆₈ as substituents are independent of each other.
Halogen atom,
Substituted or unsubstituted ring-forming aryl groups having 6 to 14 carbon atoms,
Substituted or unsubstituted heterocyclic groups having 5 to 14 ring-forming atoms,
Substituent or unsubstituted alkyl groups with 1 to 6 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkylsilyl group having 3 to 6 carbon atoms,
Substituent or unsubstituted alkoxy groups having 1 to 6 carbon atoms,
Substituent or unsubstituted ring-forming aryloxy groups having 6 to 14 carbon atoms,
Substituent or unsubstituted alkylamino groups having 2 to 12 carbon atoms,
It is 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. * Independently represent the binding site of the benzene ring with the carbon atom in the general formulas (1) to (3). ) In the general formulas (1) to (3), R ₂ is a group represented by any of the general formulas (101) to (115) and (201) to (204).
The compound according to claim 1. In the general formulas (1) to (3),
R ₁ is a group represented by any of the general formulas (101) to (110) and (201) to (204).
R ₂ is the formula (101) to (110), a group represented by any one of (201) to (204) and the general formula (X),
The compound according to claim 1. In the general formulas (1) to (3),
R ₁ is a group represented by any of the general formulas (101) to (105), (107), (109) to (115) and (201) to (204).
R ₂ is the formula (101) to (105), (107), (109) - (115), a group represented by any one of (201) to (204) and the general formula (X) is there,
The compound according to claim 1. In the general formulas (1) to (3),
R ₁ is a group represented by any of the general formulas (101) to (105).
R ₂ is a group represented by any of the general formulas (101) to (105).
The compound according to any one of claims 1 to 4. In the general formulas (1) to (3),
R ₁ is a group represented by any of the general formulas (106) to (110).
R ₂ is a group represented by any of the general formulas (106) to (110).
The compound according to any one of claims 1 to 3. In the general formulas (1) to (3),
R ₁ is a group represented by any of the general formulas (111) to (115).
R ₂ is a group represented by any of the general formulas (111) to (115).
The compound according to claim 1, claim 2 or claim 4. In the general formulas (101) to (115), (201) to (204) and the general formula (X), R _{11 to} R ₂₀ , R _{21 to} R ₃₀ , R _{31 to} R ₃₃ and R _{161 to} R _168. Are independently hydrogen atoms or substituents,
R _{11 to} R ₂₀ , R _{21 to} R ₃₀ , R _{31 to} R _33, and R _{161 to} R ₁₆₈ as substituents are independent of each other.
Substituted or unsubstituted ring-forming aryl groups having 6 to 14 carbon atoms,
Substituted or unsubstituted ring-forming heterocyclic group having 5 to 14 atoms, or substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.
The compound according to any one of claims 1 to 7. In the general formulas (101) to (115), (201) to (204) and the general formula (X), R _{11 to} R ₂₀ , R _{21 to} R ₃₀ and R _{161 to} R ₁₆₈ are hydrogen atoms. , And R _{31 to} R ₃₃ are independent of each other.
A substituted or unsubstituted ring-forming aryl group having 6 to 14 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.
The compound according to any one of claims 1 to 8. In the general formulas (101) to (115), (201) to (204) and the general formula (X), the substituent in the case of "substituted or unsubstituted" is
Substituent 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,
Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,
A heteroaryl group having 5 to 30 substituted or unsubstituted ring-forming atoms,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
Substituent or unsubstituted alkylthio groups having 1 to 30 carbon atoms,
Substituent or unsubstituted ring-forming aryloxy groups having 6 to 30 carbon atoms,
Substituted or unsubstituted ring-forming arylthio groups having 6 to 30 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 30 carbon atoms,
Substituent or unsubstituted alkynyl groups having 2 to 30 carbon atoms,
Substituent or unsubstituted aralkyl groups having 7 to 30 carbon atoms,
Substituent or unsubstituted alkylsulfonyl groups having 1 to 30 carbon atoms,
Substituent or unsubstituted ring-forming arylcarbonyl group having 6 to 30 carbon atoms,
Substituent or unsubstituted acyl groups having 1 to 30 carbon atoms,
Halogen atom,
Carboxy group,
Substituted or unsubstituted amino groups,
Nitro group,
Cyano group,
Substituted or unsubstituted silyl group,
Substituted phosphoryl group,
Hydroxy group,
Substituted phosphino group,
Ester group,
A siroxanyl group or a carbamoyl group,
The compound according to any one of claims 1 to 9. In the general formulas (101) to (115), (201) to (204) and the general formula (X), the substituent in the case of "substituted or unsubstituted" is
Unsubstituted alkyl groups with 1 to 30 carbon atoms,
An unsubstituted alkyl halide group having 1 to 30 carbon atoms,
Unsubstituted ring-forming cycloalkyl group with 3 to 30 carbon atoms,
Unsubstituted aryl groups with 6 to 30 carbon atoms,
An unsubstituted heteroaryl group having 5 to 30 ring-forming atoms,
Alkoxy groups having 1 to 30 carbon atoms, which are not substituted,
An unsubstituted alkoxy group having 1 to 30 carbon atoms,
Unsubstituted alkylthio groups with 1 to 30 carbon atoms,
An unsubstituted ring-forming aryloxy group having 6 to 30 carbon atoms,
Unsubstituted ring-forming arylthio groups having 6 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 aralkyl group having 7 to 30 carbon atoms,
An unsubstituted alkylsulfonyl group having 1 to 30 carbon atoms,
An unsubstituted ring-forming arylcarbonyl group having 6 to 30 carbon atoms,
Unsubstituted acyl groups with 1 to 30 carbon atoms,
Halogen atom,
Carboxy group,
Amino group,
Nitro group,
Cyano group,
Cyril group,
Hydroxy group,
Ester group,
A siroxanyl group or a carbamoyl group,
The compound according to any one of claims 1 to 10. A material for an organic electroluminescence device, which comprises the compound according to any one of claims 1 to 11. With the anode
With the cathode
A first organic layer contained between the anode and the cathode,
Have,
The first organic layer contains the first compound and contains
The first compound is the compound according to any one of claims 1 to 11.
Organic electroluminescence element. In the organic electroluminescence device according to claim 13,
The first organic layer is a light emitting layer.
Organic electroluminescence element. In the organic electroluminescence device according to claim 13 or 14.
The first organic layer contains the first compound and further a second compound.
The second compound is a fluorescent compound.
Organic electroluminescence element. In the organic electroluminescence device according to claim 15,
The first organic layer contains the first compound, the second compound, and a third compound.
The singlet energy _S 1 (Mat1) of the first compound, the third and singlet energy _S 1 of the compound (MAT3), but satisfies the following equation (Equation 2),
Organic electroluminescence element.
_{S 1 (Mat3)> S 1} (Mat1) ( number 2) In the organic electroluminescence device according to claim 15 or 16.
The second compound is a compound represented by the following general formula (20).
The singlet energy S ₁ (1) of the first compound and the singlet energy S ₁ (Mat 2) of the second compound satisfy the relationship of the following mathematical formula (Equation 3).
Organic electroluminescence element.
_{S 1 (Mat1)> S 1} (Mat2) ( number 3)


(In the general formula (20),
X is a nitrogen atom or a carbon atom bonded to Y,
Y is a hydrogen atom or a substituent,
R _{21 to} R ₂₆ are independently hydrogen atoms or substituents, or R ₂₁ and R ₂₂ pairs, R ₂₂ and R ₂₃ pairs, R ₂₄ and R ₂₅ pairs, and R ₂₅ and R. Any one or more of the ₂₆ pairs combine with each other to form a ring.
Y and R _{21 to} R ₂₆ as substituents are independent of each other.
Substituent 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,
Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
Substituent or unsubstituted alkylthio groups having 1 to 30 carbon atoms,
Substituent or unsubstituted ring-forming aryloxy groups having 6 to 30 carbon atoms,
Substituted or unsubstituted ring-forming arylthio groups having 6 to 30 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 30 carbon atoms,
Substituent or unsubstituted aralkyl groups having 7 to 30 carbon atoms,
A heteroaryl group having 5 to 30 substituted or unsubstituted ring-forming atoms,
Halogen atom,
Carboxy group,
Substituted or unsubstituted ester groups,
Substituted or unsubstituted carbamoyl groups,
Substituted or unsubstituted amino groups,
Nitro group,
Cyano group,
Selected from the group consisting of substituted or unsubstituted silyl groups and substituted or unsubstituted siloxanyl groups.
Z ₂₁ and Z ₂₂ are independent substituents, or Z ₂₁ and Z ₂₂ are bonded to each other to form a ring.
Z ₂₁ and Z ₂₂ as substituents are independent of each other.
Halogen atom,
Substituent or unsubstituted alkyl groups having 1 to 30 carbon atoms,
Substituent or unsubstituted alkyl halide groups having 1 to 30 carbon atoms,
Substituted or unsubstituted ring-forming aryl groups having 6 to 30 carbon atoms,
Substituent or unsubstituted alkoxy group having 1 to 30 carbon atoms,
It is selected from the group consisting of substituted or unsubstituted alkoxy halide groups having 1 to 30 carbon atoms and substituted or unsubstituted ring-forming aryloxy groups having 6 to 30 carbon atoms. ) The organic electroluminescence device according to any one of claims 13 to 17.
The first organic layer does not contain a metal complex.
Organic electroluminescence element. The organic electroluminescence device according to any one of claims 13 to 18.
The first compound is a delayed fluorescent compound,
Organic electroluminescence element. An electronic device equipped with the organic electroluminescence device according to any one of claims 13 to 19.