WO2020075783A1

WO2020075783A1 - Novel compound, organic electroluminescence element, and electronic device

Info

Publication number: WO2020075783A1
Application number: PCT/JP2019/039915
Authority: WO
Inventors: 裕基中野; 太郎八巻; 聡美田崎; 加藤　朋希
Original assignee: 出光興産株式会社
Priority date: 2018-10-09
Filing date: 2019-10-09
Publication date: 2020-04-16
Also published as: KR20210075089A; CN112789269A; WO2020075784A1

Abstract

This compound is represented by formula (1) (in formula (1), at least one of R₁-R₈ is a deuterium atom, and Ar₂ is a monovalent group represented by formula (2), (3), or (4)).

Description

Novel compounds, organic electroluminescent devices, electronic devices

The present invention relates to a novel compound, an organic electroluminescence device and an electronic device.

When a voltage is applied to the organic electroluminescence element (hereinafter, also referred to as “organic EL element”), holes are injected from the anode and electrons are injected from the cathode into the light emitting layer. Then, in the light emitting layer, the injected holes and electrons are recombined to form excitons.

In order to improve the element performance of the organic EL element, the materials used for the organic EL element are gradually being improved (for example, Patent Documents 1 to 7), but higher performance is required. In particular, the improvement of the life of the organic EL element is an important issue that leads to the life of a commercialized product, and therefore a material capable of realizing a long-life organic EL element is required.

Korean Published Patent No. 2016-0141361 U.S. Patent Application Publication No. 20170020099 Korean Published Patent No. 2017-055541 International Publication No. WO 2010/099534 International Publication No. 2010/135395 International Publication No. 2010/071362 International Publication No. 2010/066830

An object of the present invention is to provide a compound capable of producing a long-life organic EL element, a long-life organic EL element, and an electronic device using the organic EL element.

The present inventors have conducted extensive studies to achieve the above object, and as a result, have found that an organic EL device having an excellent life can be obtained by using a compound having a specific structure represented by the formula (1). Completed the invention.
According to the present invention, the following compounds, organic EL devices and electronic devices are provided.
1. A compound represented by the following formula (1).

(In equation (1),
R ₁ to R ₈ are each independently:
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more R ₉₀₁ to R ₉₀₇ exist, each of the two or more R ₉₀₁ to R ₉₀₇ may be the same or different.
At least one of R ₁ to R ₈ is a deuterium atom.
Two or more of R ₁ to R ₄ and two or more of R ₅ to R ₈ are not bonded to each other to form a ring.
L ₁ and L ₂ are each independently:
Single bond,
It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atom (s).
Ar ₁ is
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
Ar ₂ is a monovalent group represented by the following formula (2), (3) or (4).

In formulas (2) to (4),
Two or more adjacent pairs of R ₁₅ to R ₂₀ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring is formed. Do not form.
When two or more adjacent pairs of R ₁₅ to R ₂₀ are not bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, one of R ₁₃ to R ₂₀ is L ₂ Is a single bond that binds to.
When two or more adjacent pairs of R ₁₅ to R ₂₀ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, the substituted or unsubstituted saturated or unsaturated ring is R ₁₅ to R ₂₀ that are not formed, and one of R ₁₃ and R ₁₄ is a single bond that is bonded to L ₂ .
R ₁₃ to R ₂₀ , which do not form a substituted or unsubstituted saturated or unsaturated ring and which are not a single bond bonded to L ₂ , and R ₁₁ and R ₁₂ are each independently,
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1). )
2. An organic material having a cathode, an anode, and one or more organic layers arranged between the cathode and the anode, at least one of the organic layers containing the compound described in 1. Electroluminescent device.
An electronic device comprising the organic electroluminescence element according to 3.2.

According to the present invention, it is possible to provide a compound capable of manufacturing a long-life organic EL element, a long-life organic EL element, and an electronic device using the organic EL element.

[Definition]
As used herein, the term “hydrogen atom” includes isotopes having different neutron numbers, that is, protium, deuterium, and tritium.

In the present specification, in the chemical structural formula, at a bondable position where a symbol such as “R” or “D” representing a deuterium atom is not specified, a hydrogen atom, that is, a light hydrogen atom, a deuterium atom, or It is assumed that a tritium atom is bonded.

In the present specification, the number of ring-forming carbon atoms refers to 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 bridged compound, a carbocyclic compound, and a heterocyclic compound). Indicates the number of carbon atoms among the atoms. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the ring-forming carbon number. The "number of ring carbon atoms" described below is the same unless otherwise specified. For example, a benzene ring has 6 ring-forming carbons, a naphthalene ring has 10 ring-forming carbons, a pyridine ring has 5 ring-forming carbons, and a furan ring has 4 ring-forming carbons. Further, for example, the 9,9-diphenylfluorenyl group has 13 ring-forming carbon atoms, and the 9,9′-spirobifluorenyl group has 25 ring-forming carbon atoms.
When a benzene ring or a naphthalene ring is substituted with, for example, an alkyl group as a substituent, the number of carbon atoms of the alkyl group is not included in the number of ring-forming carbon atoms.

In the present specification, the number of ring-forming atoms means a compound having a structure in which atoms are cyclically bonded (for example, a monocyclic compound, a condensed ring, a ring assembly) (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, Ring compound) represents the number of atoms constituting the ring itself. The atoms that do not form a ring (eg, hydrogen atoms that terminate the bonds of the atoms that make up the ring) and the atoms that are included in the substituent when the ring is substituted with a substituent are not included in the number of ring-forming atoms. The “number of ring-forming atoms” described below is 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. A hydrogen atom bonded to a carbon atom of a pyridine ring or a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms.

In the present specification, the “carbon number XX to YY” in the expression “substituted or unsubstituted ZZ group having XX to YY carbon atoms” represents the number of carbon atoms when the ZZ group is unsubstituted. The carbon number of the substituent in the case where it is performed is not included. Here, “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.

In the present specification, “atom number XX to YY” in the expression “substituted or unsubstituted ZZ group having XX to YY atoms” means the number of atoms when the ZZ group is unsubstituted, The number of atoms of the substituent when it is included is not included. Here, “YY” is larger than “XX”, and “XX” and “YY” each mean an integer of 1 or more.

<< "Unsubstituted" in the case of "substituted or unsubstituted ZZ group" means that the ZZ group is not substituted with a substituent and a hydrogen atom is bonded. Alternatively, “substituted” in the case of “substituted or unsubstituted ZZ group” means that one or more hydrogen atoms in the ZZ group have been replaced by a substituent. Similarly, “substitution” in the case of “BB group substituted with AA group” means that one or more hydrogen atoms in BB group are replaced with AA group.

Hereinafter, the substituents described in the present specification will be described.
The ring-forming carbon number of the “unsubstituted aryl group” described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification. .
The number of ring-forming atoms of the “unsubstituted heterocyclic group” described herein is from 5 to 50, preferably from 5 to 30, more preferably from 5 to 18, unless otherwise specified herein. is there.
The carbon number of the “unsubstituted alkyl group” described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in the present specification.
The carbon number of the “unsubstituted alkenyl group” described in the present specification is 2 to 50, preferably 2 to 20, more preferably 2 to 6, unless otherwise specified in the present specification.
The carbon number of the “unsubstituted alkynyl group” described in the present specification is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise specified in the present specification.
The number of ring-forming carbon atoms of the “unsubstituted cycloalkyl group” described herein is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise specified in this specification. is there.
The number of ring-forming carbon atoms of the “unsubstituted arylene group” described in the present specification is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified in the present specification. .
The number of ring-forming atoms of the “unsubstituted divalent heterocyclic group” described in the present specification is 5 to 50, preferably 5 to 30, and more preferably 5 unless otherwise specified in the present specification. ~ 18.
The carbon number of the “unsubstituted alkylene group” described in the present specification is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified in the present specification.

Specific examples (specific example group G1) of the “substituted or unsubstituted aryl group” described in the present specification include the following unsubstituted aryl groups and substituted aryl groups. (Here, the unsubstituted aryl group refers to the case where the “substituted or unsubstituted aryl group” is the “unsubstituted aryl group”, and the substituted aryl group is the “substituted or unsubstituted aryl group”. The term "substituted aryl group" is used below.) Hereinafter, the term "aryl group" includes both "unsubstituted aryl group" and "substituted aryl group".
The “substituted aryl group” is a case where the “unsubstituted aryl group” has a substituent, and examples thereof include a group in which the following “unsubstituted aryl group” has a substituent and examples of a substituted aryl group. . Note that the examples of the “unsubstituted aryl group” and the examples of the “substituted aryl group” listed here are merely examples, and the “substituted aryl group” described in the present specification includes “unsubstituted aryl group”. The group in which the “group” has a substituent further has a substituent, and the “substituted aryl group” further has a substituent.

Unsubstituted aryl group:
Phenyl group,
p-biphenyl group,
m-biphenyl group,
o-biphenyl group,
p-terphenyl-4-yl group,
a p-terphenyl-3-yl group,
p-terphenyl-2-yl group,
m-terphenyl-4-yl group,
m-terphenyl-3-yl group,
m-terphenyl-2-yl group,
o-terphenyl-4-yl group,
o-terphenyl-3-yl group,
o-terphenyl-2-yl group,
1-naphthyl group,
2-naphthyl group,
Anthryl group,
Benzoanthryl group,
Phenanthryl group,
Benzophenanthryl group,
Phenalenyl group,
Pyrenyl group,
A chrysenyl group,
Benzochrysenyl group,
Triphenylenyl group,
Benzotriphenylenyl group,
Tetracenyl group,
Pentacenyl group,
Fluorenyl group,
9,9′-spirobifluorenyl group,
Benzofluorenyl group,
Dibenzofluorenyl group,
A fluoranthenyl group,
Benzofluoranthenyl group,
Perylenyl group

Substituted aryl group:
o-tolyl group,
m-tolyl group,
p-tolyl group,
Para-xylyl group,
Meta-xylyl group,
Ortho-xylyl group,
Para-isopropylphenyl group,
Meta-isopropylphenyl group,
Ortho-isopropylphenyl group,
Para-t-butylphenyl group,
Meta-t-butylphenyl group,
Ortho-t-butylphenyl group,
3,4,5-trimethylphenyl group,
9,9-dimethylfluorenyl group,
9,9-diphenylfluorenyl group,
9,9-di (4-methylphenyl) fluorenyl group,
9,9-di (4-isopropylphenyl) fluorenyl group,
9,9-di (4-tbutylphenyl) fluorenyl group,
A cyanophenyl group,
Triphenylsilylphenyl group,
Trimethylsilylphenyl group,
Phenylnaphthyl group,
Naphthylphenyl group

The "heterocyclic group" described in the present specification is a cyclic group containing at least one hetero atom as a ring forming atom. Specific examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.
The “heterocyclic group” described in the present specification may be a monocyclic group or a condensed ring group.
The “heterocyclic group” described in the present specification may be an aromatic heterocyclic group or an aliphatic heterocyclic group.
Specific examples of the "substituted or unsubstituted heterocyclic group" (specific example group G2) described in the present specification include the following unsubstituted heterocyclic groups and substituted heterocyclic groups. (Here, an unsubstituted heterocyclic group refers to a case where “substituted or unsubstituted heterocyclic group” is an “unsubstituted heterocyclic group”, and a substituted heterocyclic group refers to “substituted or unsubstituted heterocyclic group.” Hereinafter, the term “heterocyclic group” is a “substituted heterocyclic group”.) Hereinafter, when simply referred to as “heterocyclic group”, both “unsubstituted heterocyclic group” and “substituted heterocyclic group” are used. Including.
The “substituted heterocyclic group” is a case where the “unsubstituted heterocyclic group” has a substituent, and the following “unsubstituted heterocyclic group” has a substituent or an example of a substituted heterocyclic group. And the like. The examples of the “unsubstituted heterocyclic group” and the examples of the “substituted heterocyclic group” are merely examples, and the “substituted heterocyclic group” described in the present specification includes “unsubstituted heterocyclic group”. A group in which the “substituted heterocyclic group” has a substituent further has a substituent, and a group in which the “substituted heterocyclic group” further has a substituent is also included.

Unsubstituted heterocyclic group containing nitrogen atom:
A pyrrolyl group,
Imidazolyl group,
Pyrazolyl group,
Triazolyl group,
Tetrazolyl group,
An oxazolyl group,
Isoxazolyl group,
An oxadiazolyl group,
Thiazolyl group,
An isothiazolyl group,
Thiadiazolyl group,
Pyridyl group,
A pyridazinyl group,
Pyrimidinyl group,
Pyrazinyl group,
Triazinyl group,
Indolyl group,
Isoindolyl group,
An indolizinyl group,
Quinolizinyl group,
Quinolyl group,
An isoquinolyl group,
Cinnolyl group,
Phthalazinyl group,
Quinazolinyl group,
Quinoxalinyl group,
Benzimidazolyl group,
Indazolyl group,
A phenanthrolinyl group,
Phenanthridinyl group,
Acridinyl group,
Phenazinyl group,
Carbazolyl group,
Benzocarbazolyl group,
Morpholino group,
Phenoxazinyl group,
Phenothiazinyl group,
Azacarbazolyl group,
Diazacarbazolyl group

Unsubstituted heterocyclic group containing oxygen atom:
Frill group,
An oxazolyl group,
Isoxazolyl group,
An oxadiazolyl group,
Xanthenyl group,
Benzofuranyl group,
An isobenzofuranyl group,
Dibenzofuranyl group,
Naphthobenzofuranyl group,
Benzoxazolyl group,
Benzoisoxazolyl group,
Phenoxazinyl group,
Morpholino group,
Dinaphthofuranyl group,
Azadibenzofuranyl group,
Diazadibenzofuranyl group,
Azanaphthobenzofuranyl group,
Diazanaphthobenzofuranyl group

Unsubstituted heterocyclic group containing a sulfur atom:
Thienyl group,
Thiazolyl group,
An isothiazolyl group,
Thiadiazolyl group,
Benzothiophenyl group,
Isobenzothiophenyl group,
Dibenzothiophenyl group,
Naphthobenzothiophenyl group,
Benzothiazolyl group,
Benzoisothiazolyl group,
Phenothiazinyl group,
A dinaphthothiophenyl group,
Azadibenzothiophenyl group,
Diazadibenzothiophenyl group,
Azanaphthobenzothiophenyl group,
Diazanaphthobenzothiophenyl group

A substituted heterocyclic group containing a nitrogen atom:
(9-phenyl) carbazolyl group,
(9-biphenylyl) carbazolyl group,
(9-phenyl) phenylcarbazolyl group,
(9-naphthyl) carbazolyl group,
A diphenylcarbazol-9-yl group,
A phenylcarbazol-9-yl group,
A methylbenzimidazolyl group,
Ethyl benzimidazolyl group,
Phenyltriazinyl group,
Biphenylyltriazinyl group,
Diphenyltriazinyl group,
Phenylquinazolinyl group,
Biphenylylquinazolinyl group

A substituted heterocyclic group containing an oxygen atom:
Phenyldibenzofuranyl group,
Methyldibenzofuranyl group,
t-butyldibenzofuranyl group,
Monovalent residue of spiro [9H-xanthene-9,9 '-[9H] fluorene]

Substituted heterocyclic groups containing a sulfur atom:
Phenyldibenzothiophenyl group,
A methyldibenzothiophenyl group,
t-butyldibenzothiophenyl group,
Monovalent residue of spiro [9H-thioxanthene-9,9 '-[9H] fluorene]

A monovalent group derived by removing one hydrogen atom bonded to a ring-forming atom of the following unsubstituted heterocycle containing at least one of a nitrogen atom, an oxygen atom, and a sulfur atom, and the following unsubstituted A group in which a monovalent group derived by removing one hydrogen atom bonded to a ring-forming atom of a heterocycle has a substituent:

In the formulas (XY-1) to (XY-18), X _A and Y _A are each independently an oxygen atom, a sulfur atom, NH, or CH ₂ . However, at least one of X _A and Y _A is an oxygen atom, a sulfur atom, or NH.
The heterocyclic ring represented by the above formulas (XY-1) to (XY-18) has a bond at an arbitrary position to be a monovalent heterocyclic group.
The monovalent group derived from the unsubstituted heterocyclic ring represented by the above formulas (XY-1) to (XY-18) has a substituent when the carbon atom constituting the skeleton in these formulas is when bonded hydrogen atoms is replaced by a substituent, or, X _a and Y _a is NH or CH _2, hydrogen atoms in these NH or CH ₂ may refer to a state in which is replaced by a substituent.

Specific examples (specific example group G3) of the “substituted or unsubstituted alkyl group” described in the present specification include the following unsubstituted alkyl groups and substituted alkyl groups. (Here, the unsubstituted alkyl group refers to a case where the “substituted or unsubstituted alkyl group” is an “unsubstituted alkyl group”, and the substituted alkyl group refers to a “substituted or unsubstituted alkyl group” Hereinafter, the term “substituted alkyl group” is referred to.) Hereinafter, the term “alkyl group” includes both “unsubstituted alkyl group” and “substituted alkyl group”.
The “substituted alkyl group” is a case where the “unsubstituted alkyl group” has a substituent, and examples thereof include a group in which the following “unsubstituted alkyl group” has a substituent and examples of a substituted alkyl group. . The examples of the “unsubstituted alkyl group” and the examples of the “substituted alkyl group” listed here are merely examples, and the “substituted alkyl group” described in this specification includes “unsubstituted alkyl group”. The group in which the “group” has a substituent further has a substituent, and the “substituted alkyl group” further has a substituent.

Unsubstituted alkyl group:
Methyl group,
Ethyl group,
n-propyl group,
Isopropyl group,
n-butyl group,
Isobutyl group,
s-butyl group,
t-butyl group

Substituted alkyl group:
Heptafluoropropyl group (including isomers),
Pentafluoroethyl group,
2,2,2-trifluoroethyl group,
Trifluoromethyl group

Specific examples (specific example group G4) of the “substituted or unsubstituted alkenyl group” described in the present specification include the following unsubstituted alkenyl groups and substituted alkenyl groups. (Here, the unsubstituted alkenyl group refers to a case where the “substituted or unsubstituted alkenyl group” is an “unsubstituted alkenyl group”, and the “substituted alkenyl group” refers to a “substituted or unsubstituted alkenyl group.” Is a "substituted alkenyl group".) Hereinafter, the term "alkenyl group" includes both "unsubstituted alkenyl group" and "substituted alkenyl group".
The `` substituted alkenyl group '' is a case where the `` unsubstituted alkenyl group '' has a substituent, and examples of the following `` unsubstituted alkenyl group '' include a group having a substituent and a substituted alkenyl group. . Note that the examples of the “unsubstituted alkenyl group” and the examples of the “substituted alkenyl group” are merely examples, and the “substituted alkenyl group” described in the present specification includes “unsubstituted alkenyl group”. The group in which the “group” has a substituent further has a substituent, and the “substituted alkenyl group” further has a substituent.

Unsubstituted alkenyl group and substituted alkenyl group:
Vinyl group,
Allyl group,
1-butenyl group,
2-butenyl group,
A 3-butenyl group,
1,3-butanedienyl group,
1-methylvinyl group,
1-methylallyl group,
1,1-dimethylallyl group,
2-methylallyl group,
1,2-dimethylallyl group

Specific examples (specific example group G5) of the “substituted or unsubstituted alkynyl group” described in the present specification include the following unsubstituted alkynyl groups. (Here, the unsubstituted alkynyl group refers to a case where the “substituted or unsubstituted alkynyl group” is an “unsubstituted alkynyl group”.) Hereinafter, when simply referred to as “alkynyl group”, Alkynyl group "and" substituted alkynyl group ".
The “substituted alkynyl group” is a case where the “unsubstituted alkynyl group” has a substituent, and examples thereof include the following “unsubstituted alkynyl group” having a substituent.

Unsubstituted alkynyl group:
Ethynyl group

Specific examples (specific example group G6) of the “substituted or unsubstituted cycloalkyl group” described in the present specification include the following unsubstituted cycloalkyl groups and substituted cycloalkyl groups. (Here, the unsubstituted cycloalkyl group refers to the case where the “substituted or unsubstituted cycloalkyl group” is an “unsubstituted cycloalkyl group”, and the substituted cycloalkyl group is the “substituted or unsubstituted The term "cycloalkyl group" means a "substituted cycloalkyl group".) Hereinafter, when simply referring to "cycloalkyl group", both "unsubstituted cycloalkyl group" and "substituted cycloalkyl group" are referred to. Including.
"Substituted cycloalkyl group" is a case where "unsubstituted cycloalkyl group" has a substituent, and examples of the following "unsubstituted cycloalkyl group" have a substituent and substituted cycloalkyl groups. And the like. It should be noted that the examples of the “unsubstituted cycloalkyl group” and the examples of the “substituted cycloalkyl group” are merely examples, and the “substituted cycloalkyl group” described in this specification includes “unsubstituted cycloalkyl group”. A group in which the “substituted cycloalkyl group” further has a substituent, a group in which the “substituted cycloalkyl group” further has a substituent, and the like are also included.

Unsubstituted aliphatic ring group:
Cyclopropyl group,
Cyclobutyl group,
Cyclopentyl group,
Cyclohexyl group,
A 1-adamantyl group,
A 2-adamantyl group,
1-norbornyl group,
2-norbornyl group

Substituted cycloalkyl group:
4-methylcyclohexyl group

Specific examples of the group represented by —Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ) described in the present specification (specific example group G7) include:
-Si (G1) (G1) (G1),
-Si (G1) (G2) (G2),
-Si (G1) (G1) (G2),
-Si (G2) (G2) (G2),
-Si (G3) (G3) (G3),
-Si (G5) (G5) (G5),
-Si (G6) (G6) (G6)
Is mentioned.
here,
G1 is an "aryl group" described in Specific Example Group G1.
G2 is the “heterocyclic group” described in Specific Example Group G2.
G3 is the “alkyl group” described in Specific Example Group G3.
G5 is the “alkynyl group” described in Specific Example Group G5.
G6 is the “cycloalkyl group” described in Specific Example Group G6.

Specific examples of the group represented by —O— (R ₉₀₄ ) described in the present specification (specific example group G8) include
-O (G1),
-O (G2),
-O (G3),
-O (G6)
Is mentioned.
here,
G1 is an "aryl group" described in Specific Example Group G1.
G2 is the “heterocyclic group” described in Specific Example Group G2.
G3 is the “alkyl group” described in Specific Example Group G3.
G6 is the “cycloalkyl group” described in Specific Example Group G6.

Specific examples of the group represented by -S- (R ₉₀₅ ) described in the present specification (specific example group G9) include
-S (G1),
-S (G2),
-S (G3),
-S (G6)
Is mentioned.
here,
G1 is an "aryl group" described in Specific Example Group G1.
G2 is the “heterocyclic group” described in Specific Example Group G2.
G3 is the “alkyl group” described in Specific Example Group G3.
G6 is the “cycloalkyl group” described in Specific Example Group G6.

Specific examples of the group represented by -N (R ₉₀₆ ) (R ₉₀₇ ) (specific example group G10) described in the present specification include:
-N (G1) (G1),
-N (G2) (G2),
-N (G1) (G2),
-N (G3) (G3),
-N (G6) (G6)
Is mentioned.
here,
G1 is an "aryl group" described in Specific Example Group G1.
G2 is the “heterocyclic group” described in Specific Example Group G2.
G3 is the “alkyl group” described in Specific Example Group G3.
G6 is the “cycloalkyl group” described in Specific Example Group G6.

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

A specific example of the “alkoxy group” described in the present specification is a group represented by —O (G3), where G3 is an “alkyl group” described in the specific example group G3. The carbon number of the “unsubstituted alkoxy group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
A specific example of the “alkylthio group” described in the present specification is a group represented by —S (G3), where G3 is the “alkyl group” described in the specific example group G3. The carbon number of the “unsubstituted alkylthio group” is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in this specification.
A specific example of the “aryloxy group” described in the present specification is a group represented by —O (G1), where G1 is the “aryl group” described in the specific example group G1. The ring-forming carbon number of the “unsubstituted aryloxy group” is from 6 to 50, preferably from 6 to 30, and more preferably from 6 to 18, unless otherwise specified herein.
A specific example of the “arylthio group” described in the present specification is a group represented by —S (G1), where G1 is the “aryl group” described in the specific example group G1. The ring-forming carbon number of the “unsubstituted arylthio group” is from 6 to 50, preferably from 6 to 30, and more preferably from 6 to 18, unless otherwise specified herein.
A specific example of the “aralkyl group” described in the present specification is a group represented by — (G3) — (G1), wherein G3 is an “alkyl group” described in the specific example group G3. , G1 is the “aryl group” described in Specific Example Group G1. Thus, an “aralkyl group” is an embodiment of a “substituted alkyl group” substituted with an “aryl group”. The carbon number of the “unsubstituted aralkyl group” which is the “unsubstituted alkyl group” substituted by the “unsubstituted aryl group” is 7 to 50, preferably 7 unless otherwise specified in the present specification. -30, more preferably 7-18.
Specific examples of the “aralkyl group” include, for example, benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, 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-naphthylethyl group, 2- β-naphthylethyl group, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group and the like.

Unless otherwise specified, the substituted or unsubstituted aryl group described in the present specification is preferably a phenyl group, a p-biphenyl group, an m-biphenyl group, an o-biphenyl group, a p-terphenyl- 4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl- 2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, phenanthryl group , A pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-diphenylfluorenyl group and the like.

The substituted or unsubstituted heterocyclic group described in the present specification is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, unless otherwise specified in the present specification. Nanthrolinyl group, carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group, Dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, (9 -Phenyl) carbazolyl group ((9-phenyl) carbazolyl -1-yl group, (9-phenyl) carbazol-2-yl group, (9-phenyl) carbazol-3-yl group, or (9-phenyl) carbazol-4-yl group), (9-biphenylyl) carbazolyl Group, (9-phenyl) phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyltriazinyl group, diphenyltriazinyl group, phenyldibenzofura Nyl, phenyldibenzothiophenyl, indolocarbazolyl, pyrazinyl, pyridazinyl, quinazolinyl, cinnolinyl, phthalazinyl, quinoxalinyl, pyrrolyl, indolyl, pyrrolo [3,2,1-jk] Carbazolyl group, furanyl group, benzofuranyl group, thiophenyl group, Benzothiophenyl, pyrazolyl, imidazolyl, benzimidazolyl, triazolyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, isothiazolyl, benzisothiazolyl, thiadiazolyl, isoxazolyl, benzisoxazolyl And a pyridinyl group, a piperidinyl group, a piperazinyl group, an imidazolidinyl group, an indolo [3,2,1-jk] carbazolyl group, a dibenzothiophenyl group, and the like.

The above-mentioned dibenzofuranyl group and dibenzothiophenyl group are specifically any one of the following groups unless otherwise described in this specification.

In the formulas (XY-76) to (XY-79), X _B is an oxygen atom or a sulfur atom.

Unless otherwise specified, the substituted or unsubstituted alkyl group described in the present specification is preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group. And the like.

Unless otherwise specified, the “substituted or unsubstituted arylene group” described in the present specification means a divalent group of the above “aryl group”. Specific examples of the “substituted or unsubstituted arylene group” (specific example group G12) include a divalent group of the “aryl group” described in specific example group G1. That is, as a specific example (specific group G12) of the "substituted or unsubstituted arylene group", a group excluding one hydrogen bonded to the ring-forming carbon of the "aryl group" described in the specific group G1. Is.

Specific examples (specific example group G13) of the “substituted or unsubstituted divalent heterocyclic group” described in the present specification include groups obtained by divalently converting the “heterocyclic group” described in the specific example group G2. Is mentioned. That is, specific examples (specific example group G13) of the “substituted or unsubstituted divalent heterocyclic group” include one of the “heterocyclic groups” bonded to the ring-forming atom of the “heterocyclic group” described in the specific example group G2. It is a group excluding hydrogen.

具体 As a specific example (specific example group G14) of the “substituted or unsubstituted alkylene group” described in the present specification, a group in which the “alkyl group” described in the specific example group G3 is divalent is exemplified. That is, as a specific example (specific example group G14) of the “substituted or unsubstituted alkylene group”, one hydrogen bonded to the carbon forming the alkane structure of the “alkyl group” described in the specific example group G3 Excluded groups.

置換 The substituted or unsubstituted arylene group described in the present specification is preferably any one of the following groups unless otherwise described in the present specification.

In the formulas (XY-20) to (XY-29), (XY-83) and (XY-84), R ₉₀₈ is a substituent.
m901 is 0 to a 4 integer, when m901 represents 2 or more, to _{R 908} of existing in plural numbers may be the same as each other or may be different.

In the formulas (XY-30) to (XY-40), R ₉₀₉ is each independently a hydrogen atom or a substituent. Two R ₉₀₉ may be bonded to each other via a single bond to form a ring.

In formulas (XY-41) to (XY-46), R ₉₁₀ is a substituent.
m902 is an integer of 0 to 6. When m902 is 2 or more, a plurality of R ₉₁₀ may be the same as or different from each other.

置換 The substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably any one of the following groups unless otherwise described in the present specification.

In the formulas (XY-50) to (XY-60), R ₉₁₁ is a hydrogen atom or a substituent.

In the formula (XY-65) ~ (XY -75), X B is an oxygen atom or a sulfur atom.

In the present specification, the following formula (where the parent skeleton is an anthracene ring) in the case where “one or more pairs of adjacent two or more bind to each other to form a substituted or unsubstituted saturated or unsaturated ring” XY-80) will be described as an example.

For example, among R ₉₂₁ to R ₉₃₀ , “adjacent two which form a ring when one or more adjacent two or more are bonded to each other to form a ring” includes R ₉₂₁ and R ₉₂₂ , R ₉₂₂ and _R _{923, R 923} and _R _{924, R 924} and _R _{930, R 930} and _R _{925, R 925} and _R _{926, R 926} and _R _{927, R 927} and _R _{928, R 928} and _{R 929,} and R ₉₂₉ and R ₉₂₁ .

The “one or more sets” means that two or more adjacent two sets may form a ring at the same time. For example, when R ₉₂₁ and R ₉₂₂ combine with each other to form ring A, and at the same time, R ₉₂₅ and R ₉₂₆ combine with each other to form ring B, the compound is represented by the following formula (XY-81) .

“When two or more adjacent groups form a ring”, for example, R ₉₂₁ and R ₉₂₂ combine with each other to form ring A, and R ₉₂₂ and R ₉₂₃ combine with each other to form ring C In the case where three adjacent R ₉₂₁ to R ₉₂₃ are fused to the anthracene mother skeleton to form a ring A and a ring C sharing R ₉₂₂ , they are represented by the following formula (XY-82).

The rings A to C formed in the above formulas (XY-81) and (XY-82) are saturated or unsaturated rings.
“Unsaturated ring” means an aromatic hydrocarbon ring or an aromatic heterocyclic ring. “Saturated ring” means an aliphatic hydrocarbon ring or an aliphatic heterocyclic ring.
For example, in Formula (XY-81), a ring A formed by bonding R ₉₂₁ and R ₉₂₂ to each other has a carbon atom of an anthracene skeleton to which R ₉₂₁ is bonded and a carbon atom of an anthracene skeleton to which R ₉₂₂ is bonded. A ring formed by atoms and one or more optional elements is meant. As a specific example, when a ring A is formed by R ₉₂₁ and R ₉₂₂ , the carbon atom of the anthracene skeleton to which R ₉₂₁ is bonded, the carbon atom of the anthracene skeleton to which R ₉₂₂ is bonded, and four carbon atoms are different. When forming a saturated ring, the ring formed by R ₉₂₁ and R ₉₂₂ is a benzene ring. When a saturated ring is formed, the ring is a cyclohexane ring.

Here, the “arbitrary element” is preferably a C element, an N element, an O element, or an S element. In any element (for example, in the case of the C element or the N element), a bond that does not participate in ring formation may be terminated with a hydrogen atom or the like, or may be substituted with an arbitrary substituent. When any element other than the C element is included, the formed ring is a heterocyclic ring.
“One or more optional elements” constituting a saturated or unsaturated ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and still more preferably 3 or more and 5 or less. .

As a specific example of the aromatic hydrocarbon ring, a structure in which the aryl group mentioned as a specific example in the specific example group G1 is terminated with a hydrogen atom is given.
As a specific example of the aromatic heterocyclic ring, a structure in which the aromatic heterocyclic group described as a specific example in the specific example group G2 is terminated with a hydrogen atom is given.
Specific examples of the aliphatic hydrocarbon ring include a structure in which the cycloalkyl group mentioned as a specific example in Specific Example Group G6 is terminated with a hydrogen atom.
When the above “saturated or unsaturated ring” has a substituent, the substituent is, for example, an “optional substituent” described later. Specific examples of the substituent in the case where the above “saturated or unsaturated ring” has a substituent are the substituents described in the above section of “the substituent described in the present specification”.

In one embodiment of the present specification, the substituent in the case of “substituted or unsubstituted” (hereinafter, may be referred to as “optional substituent”) may be:
An unsubstituted alkyl group having 1 to 50 carbon atoms,
An unsubstituted alkenyl group having 2 to 50 carbon atoms,
An unsubstituted alkynyl group having 2 to 50 carbon atoms,
An unsubstituted cycloalkyl group having 3 to 50 carbon atoms for ring formation,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N ( _R906 ) ( _R907 )
(here,
R ₉₀₁ to R ₉₀₇ are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. When two or more R ₉₀₁ to R ₉₀₇ exist, each of the two or more R ₉₀₁ to R ₉₀₇ may be the same or different. ),
Halogen atom, cyano group, nitro group,
It is a group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms and an unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.

In one embodiment, the substituents when referred to as "substituted or unsubstituted" are:
An alkyl group having 1 to 50 carbon atoms,
It is a group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a monovalent heterocyclic group having 5 to 50 ring atoms.

In one embodiment, the substituents when referred to as "substituted or unsubstituted" are:
An alkyl group having 1 to 18 carbon atoms,
It is a group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a monovalent heterocyclic group having 5 to 18 ring atoms.

具体 Specific examples of each of the optional substituents are as described above.

In the present specification, unless otherwise specified, adjacent substituents may be substituted with a saturated or unsaturated ring (preferably a substituted or unsubstituted saturated or unsaturated 5- or 6-membered ring, (Preferably, a benzene ring).
In the present specification, an optional substituent may further have a substituent unless otherwise specified. Examples of the substituent further included in the optional substituent include those similar to the optional substituent described above.

[New compound]
The compound according to one embodiment of the present invention is represented by the following formula (1).

In formulas (2) to (4),
Two or more adjacent pairs of R ₁₅ to R ₂₀ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring is formed. Do not form.
When two or more adjacent pairs of R ₁₅ to R ₂₀ are not bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, one of R ₁₃ to R ₂₀ is L ₂ Is a single bond that binds to.
When two or more adjacent pairs of R ₁₅ to R ₂₀ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, the substituted or unsubstituted saturated or unsaturated ring is R ₁₅ to R ₂₀ that are not formed, and one of R ₁₃ and R ₁₄ is a single bond that is bonded to L ₂ .
R ₁₃ to R ₂₀ , which do not form a substituted or unsubstituted saturated or unsaturated ring and which are not a single bond bonded to L ₂ , and R ₁₁ and R ₁₂ are each independently,
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1). )

The compound according to one embodiment of the present invention, having the above structure, can improve device performance when used in an organic EL device. Specifically, it becomes possible to provide an organic EL element having a longer life.
Further, according to one aspect of the present invention, there can be provided a method for improving the performance of an organic EL device, which comprises using the above compound in a light emitting layer of the organic EL device. Specifically, the method specifically includes a compound having the same structure as the compound represented by the formula (1) except that the host material contains only a light hydrogen atom as a hydrogen atom (hereinafter, also referred to as a “light hydrogen form”). This makes it possible to improve the performance of the organic EL element, as compared with the case of using. Note that the case where a light hydrogen is used means that substantially only a light hydrogen is used as the host material in the light emitting layer (the content of the light hydrogen is based on the sum of the compound represented by the formula (1) and the light hydrogen). The ratio is 90 mol% or more, 95 mol% or more, or 99 mol% or more).
That is, as a host material, at least one of the light hydrogen atoms on the anthracene skeleton was replaced with a deuterium atom among the light hydrogen atoms of the light hydrogen form instead of or in addition to the light hydrogen form. By using a compound (a compound represented by the formula (1)), the performance can be enhanced.

All of R ₁ to R ₈ may be deuterium atoms, or some (eg, 1 or 2 or more) may be deuterium atoms.
R ₁ to R ₈ which are not deuterium atoms are preferably hydrogen atoms (light hydrogen atoms).

In one embodiment, at least one of the hydrogen atoms possessed by one or more selected from the group consisting of L ₁ and L ₂ is a deuterium atom. Specifically, in one embodiment, one or more selected from the group consisting of L ₁ and L ₂ is an unsubstituted arylene group having 6 to 30 ring-forming carbon atoms in which at least one of hydrogen atoms is a deuterium atom. Or an unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms in which at least one of hydrogen atoms is a deuterium atom.

In one embodiment, L ₁ and L ₂ are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 14 ring carbon atoms. Preferably, at least one of L ₁ and L ₂ is a single bond.

In one embodiment, R ₁₃ or R ₁₄ in formulas (2) to (4) is a single bond that is bonded to L ₂ .

In one embodiment, two or more adjacent pairs of R ₁₅ to R ₂₀ in formulas (2) to (4) do not bond with each other to form a substituted or unsubstituted saturated or unsaturated ring.

In one embodiment, among R ₁₁ to R ₂₀ in formulas (2) to (4), a hydrogen atom is not a single bond that bonds to L ₂ and does not contribute to ring formation.

In one embodiment, at least one of R ₁₁ to R ₂₀ in formulas (2) to (4) that is not a single bond that bonds to L ₂ and does not contribute to ring formation is a deuterium atom.

In one embodiment, at least one hydrogen atom contained in one or more of Ar ₁ is a deuterium atom. Specifically, in one embodiment, Ar ₁ is an unsubstituted aryl group having 6 to 50 ring carbon atoms in which at least one of hydrogen atoms is a deuterium atom, or at least one of hydrogen atoms is a deuterium atom. It is an unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.

Ar ₁ is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and more preferably selected from groups represented by the following formulas (a1) to (a4).

(In the formulas (a1) to (a4), * represents a single bond bonded to L ₁ .
R _21's are each independently
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1).
m1 is independently an integer of 0 to 4.
m2 is independently an integer of 0 to 5.
m3 is independently an integer of 0 to 7.
When each of m1 to m3 is 2 or more, a plurality of R _21's may be the same as or different from each other.
When m1 to m3 are each 2 or more, a plurality of adjacent R ₂₁ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form. )

The presence of a deuterium atom in the compound is confirmed by mass spectrometry or ¹ H-NMR analysis. Further, the bonding position of the deuterium atom in the compound is specified by ¹ H-NMR analysis. Specifically, it is as follows.
The target compound is subjected to mass spectrometry, and it can be confirmed that the target compound contains one deuterium atom by increasing the molecular weight by 1 as compared with the corresponding compound in which all hydrogen atoms are light hydrogen atoms. In addition, since no signal is generated for deuterium atoms by ¹ H-NMR analysis, the number of deuterium atoms contained in the molecule is determined by an integrated value obtained by performing ¹ H-NMR analysis on the target compound. You can check. In addition, ¹ H-NMR analysis is performed on the target compound, and the binding position of a deuterium atom can be specified by assigning a signal.

A composition according to one embodiment of the present invention contains a compound represented by the formula (1), and the content ratio of the latter is 99 mol% or less based on the total amount of the compound represented by the formula (1) and a hydrogen hydride. Is. The content ratio of the deuterium is confirmed by mass spectrometry.
Further, in the composition according to one embodiment of the present invention, the content ratio of the former to the total of the compound represented by the formula (1) and the light hydrogen compound is 30 mol% or more, 50 mol% or more, 70 mol% or more, 90 It is mol% or more, 95 mol% or more, 99 mol% or more, or 100 mol%.

In one embodiment, the compound represented by the formula (1) has the formula (1-1), (1-2), (1-3), (1-4), (1-5) or (1- It is a compound represented by 6).

(In the formulas (1-1), (1-2), (1-3), (1-4), (1-5) and (1-6), R ₁ to R ₈ and R ₁₁ to R ₂₀ , Ar ₁ , L ₁ and L ₂ are as defined in the above formula (1).)

In one embodiment, the compound represented by the formula (1) is represented by the following formula (1-11), (1-12), (1-13), (1-14), (1-15) or (1- It is a compound represented by 16).

(In the formulas (1-11), (1-12), (1-13), (1-14), (1-15) and (1-16), R ₁ to R ₈ , Ar ₁ and L ₁ Is as defined in the above formula (1).)

In one embodiment, the compound represented by the formula (1) is represented by the following formula (1-21), (1-22), (1-23), (1-24), (1-25) or (1- It is a compound represented by 26).

(In the formulas (1-21), (1-22), (1-23), (1-24), (1-25) and (1-26), Ar ₁ and L ₁ are the same as those in the formula (1). ) Is as defined in.)

The compound represented by the formula (1) can be synthesized by following the synthetic method described in the examples and using known alternative reactions or starting materials according to the intended product.

Examples of the compound according to one embodiment of the present invention are shown below. In the following specific examples, D represents a deuterium atom.

The above compound can be used as a material for an organic EL device, preferably as a host material for a light emitting layer.

[Organic EL device]
An organic EL device according to one aspect of the present invention has a cathode, an anode, and one or more organic layers arranged between the cathode and the anode, and the organic layer is represented by the formula (1). Contains the compound represented or the composition of the invention described above. As long as the organic layer does not contain the compound represented by formula (1) or the composition of the present invention described above, conventionally known materials and device configurations can be applied as long as the effects of the present invention are not impaired. In the organic EL device, the light emitting layer of the organic layer preferably contains the compound represented by the formula (1) or the composition of the present invention.

In one embodiment, the light emitting layer of the organic EL device according to one aspect of the present invention contains a compound represented by the formula (1) and a light hydrogen compound, and the content ratio of the latter to the total thereof is 99 mol% or less. Is.
In one embodiment, the light-emitting layer of the organic EL element according to one embodiment of the present invention includes the compound represented by the formula (1) and a deuterium compound, and the content of the former is 30 mols relative to the total. %, 50 mol% or more, 70 mol% or more, 90 mol% or more, 95 mol% or more, 99 mol% or more, or 100 mol%.

One aspect of the organic EL device of the present invention preferably has a hole transport layer between the anode and the light emitting layer.

One aspect of the organic EL device of the present invention preferably has an electron transport layer between the cathode and the light emitting layer.

As a typical element structure of the organic EL element of the present invention,
(1) Anode / light emitting layer / cathode (2) Anode / hole injection layer / light emitting layer / cathode (3) Anode / light emitting layer / electron injection / transport layer / cathode (4) Anode / hole injection layer / light emitting layer / Electron injection / transport layer / cathode (5) anode / organic semiconductor layer / light emitting layer / cathode (6) anode / organic semiconductor layer / electron barrier layer / light emitting layer / cathode (7) anode / organic semiconductor layer / light emitting layer / Adhesion improving layer / cathode (8) anode / hole injection / transport layer / light emitting layer / electron injection / transport layer / cathode (9) anode / insulating layer / light emitting layer / insulating layer / cathode (10) anode / inorganic semiconductor layer / Insulating layer / Light emitting layer / Insulating layer / Cathode (11) Anode / Organic semiconductor layer / Insulating layer / Light emitting layer / Insulating layer / Cathode (12) Anode / Insulating layer / Hole injection / transport layer / Light emitting layer / Insulating layer / Cathode (13) Anode / insulating layer / hole injecting / transporting layer / light emitting layer / electron injecting / transporting layer / cathode.
The configuration (8) is preferably used in the above, but the configuration is not limited thereto.

In the present specification, "hole injection / transport layer" means "at least one of a hole injection layer and a hole transport layer", and "electron injection / transport layer" means "electron injection layer and electron At least one of the transport layers ".

The light-emitting layer preferably contains, in addition to the compound (host material) represented by the formula (1), the following formulas (11), (21), (31), (41), (51), (61), It contains at least one compound (dopant material) selected from the group consisting of (71) and (81).

(Compound represented by Formula (11))
The compound represented by the formula (11) will be described.

[In formula (11),
One or more adjacent two or more of R ₁₀₁ to R ₁₁₀ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring; Does not form a ring.
At least one of R ₁₀₁ to R ₁₁₀ is a monovalent group represented by the following formula (12).
R ₁₀₁ to R ₁₁₀ which do not form a substituted or unsubstituted saturated or unsaturated ring and which are not a monovalent group represented by the following formula (12) are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1).

(In Formula (12), Ar ₁₀₁ and Ar ₁₀₂ are each independently
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
L ₁₀₁ to L ₁₀₃ are independently
Single bond,
It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atom (s). )]

In the formula (11), it is preferable that two of R ₁₀₁ to R ₁₁₀ are groups represented by the formula (12).

In one embodiment, the compound represented by the formula (11) is represented by the following formula (13).

(In the formula (13), R ₁₁₁ to R ₁₁₈ are the same as R ₁₀₁ to R ₁₁₀ in the formula (11), which are not the monovalent group represented by the formula (12). Ar ₁₀₁ and Ar ₁₀₂ , L ₁₀₁ , L _102, and L ₁₀₃ are as defined in the above formula (12).)

In the formula (11), L ₁₀₁ is preferably a single bond, and L ₁₀₂ and L ₁₀₃ are preferably single bonds.

In one embodiment, the compound represented by the formula (11) is represented by the following formula (14) or (15).

(In the formula (14), R ₁₁₁ to R ₁₁₈ are as defined in the formula (13). Ar ₁₀₁ , Ar ₁₀₂ , L ₁₀₂ and L ₁₀₃ are as defined in the formula (12). .)

(In the formula (15), R ₁₁₁ to R ₁₁₈ are as defined in the formula (13). Ar ₁₀₁ and Ar ₁₀₂ are as defined in the formula (12).)

In the formulas (11) and (12), preferably, at least one of Ar ₁₀₁ and Ar ₁₀₂ is a group represented by the following formula (16).

(In equation (16),
X ₁₀₁ represents an oxygen atom or a sulfur atom.
One or more of two or more of R ₁₂₁ to R ₁₂₇ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form a ring.
R ₁₂₁ to R ₁₂₇ which do not form a substituted or unsubstituted saturated or unsaturated ring are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1). )

X ₁₀₁ is preferably an oxygen atom.
At least one of R ₁₂₁ to R ₁₂₇ is
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
It is preferably a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.

In the formulas (11) and (12), Ar ₁₀₁ is preferably a group represented by the formula (16), and Ar ₁₀₂ is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. .

In one embodiment, the compound represented by the formula (11) is represented by the following formula (17).

(In the formula (17), R ₁₁₁ to R ₁₁₈ are as defined in the formula (13). R ₁₂₁ to R ₁₂₇ are as defined in the formula (16).
R ₁₃₁ to R ₁₃₅ are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1). )

化合物 Specific examples of the compound represented by the formula (11) include the following compounds. In the following specific examples, Me represents a methyl group.

(Compound represented by Formula (21))
The compound represented by formula (21) will be described.

(In formula (21),
Z is each independently CR _a or N.
The A1 ring and the A2 ring are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms.
When plural R _a are present, one or more adjacent two or more sets of plural R _a are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or substituted or Does not form an unsubstituted saturated or unsaturated ring.
When a plurality of R _b are present, one or more pairs of adjacent two or more of the plurality of R _b are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or Does not form an unsubstituted saturated or unsaturated ring.
When a plurality of R _c is present, one or more adjacent two or more sets of the plurality of R _c are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or substituted or Does not form an unsubstituted saturated or unsaturated ring.
n21 and n22 are each independently an integer of 0 to 4.
R _a to R _c which do not form a substituted or unsubstituted saturated or unsaturated ring are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1). )

The “aromatic hydrocarbon ring” of the A1 ring and the A2 ring has the same structure as the above-described compound in which a hydrogen atom has been introduced into the “aryl group”. The “aromatic hydrocarbon ring” of the A1 ring and the A2 ring includes two carbon atoms on the central fused bicyclic structure of the formula (21) as ring-forming atoms. Specific examples of the “substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms” include compounds in which a hydrogen atom has been introduced into the “aryl group” described in Specific Example Group G1.
The “heterocycle” of the A1 ring and the A2 ring has the same structure as the compound in which a hydrogen atom has been introduced into the above “heterocyclic group”. The "heterocycle" of the A1 ring and the A2 ring includes two carbon atoms on the central fused bicyclic structure of the formula (21) as ring-forming atoms. Specific examples of the “substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms” include compounds in which a hydrogen atom has been introduced into the “heterocyclic group” described in Specific Example Group G2.

R _b is bonded to any of the carbon atoms forming the aromatic hydrocarbon ring of A1 ring or to the atoms forming the heterocyclic ring of A1 ring.
R _c is bonded to any of the carbon atoms forming the aromatic hydrocarbon ring of the A2 ring or any of the atoms forming the heterocyclic ring of the A2 ring.

At least one (preferably two) of R _a to R _c is preferably a group represented by the following formula (21a).
—L ₂₀₁ —Ar ₂₀₁ (21a)
(In the equation (21a),
L ₂₀₁ is
Single bond,
It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atom (s).
Ar ₂₀₁ is
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
A substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms, or a group represented by the following formula (21b).

(In formula (21b),
L ₂₁₁ and L ₂₁₂ are each independently
Single bond,
It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atom (s).
Ar ₂₁₁ and Ar ₂₁₂ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring or no substituted or unsubstituted saturated or unsaturated ring.
Ar ₂₁₁ and Ar ₂₁₂ which do not form a substituted or unsubstituted saturated or unsaturated ring are each independently
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
It is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. ))

In one embodiment, the compound represented by the formula (21) is represented by the following formula (22).

(In formula (22),
One or more pairs of adjacent two or more of R ₂₀₁ to R ₂₁₁ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring; Does not form a ring.
R ₂₀₁ to R ₂₁₁ which do not form a substituted or unsubstituted saturated or unsaturated ring are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1). )

At least one (preferably two) of R ₂₀₁ to R ₂₁₁ is preferably a group represented by the above formula (21a). Preferably, R ₂₀₄ and R ₂₁₁ are groups represented by the above formula (21a).

In one embodiment, the compound represented by the formula (21) is a compound in which the structure represented by the following formula (21-1) or (21-2) is bonded to the A1 ring. Further, in one embodiment, the compound represented by the formula (22) is a compound in which the structure represented by the following formula (21-1) or (21-2) is bound to the ring to which R ₂₀₄ to R ₂₀₇ are bound. Is.

(In the formula (21-1), the two bonds * are each independently bonded to a ring-forming carbon atom of an aromatic hydrocarbon ring or a ring-forming atom of a heterocyclic ring of the A1 ring of the formula (21); Alternatively, it binds to any of R ₂₀₄ to R _{207 in} the formula (22).
The three bonds * in formula (21-2) are each independently bonded to the ring-forming carbon atom of the aromatic hydrocarbon ring of the A1 ring of formula (21) or the ring-forming atom of the heterocycle, or It is bonded to any of R ₂₀₄ to R _{207 in} (22).
At least one pair of two or more of R ₂₂₁ to R ₂₂₇ and R ₂₃₁ to R ₂₃₉ is bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or Does not form a substituted saturated or unsaturated ring.
R ₂₂₁ to R ₂₂₇ and R ₂₃₁ to R ₂₃₉ which do not form a substituted or unsubstituted saturated or unsaturated ring are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1). )

In one embodiment, the compound represented by the formula (21) is a compound represented by the following formula (21-3), (21-4) or (21-5).

(In the formulas (21-3), (21-4) and (21-5),
The ring A1 is as defined in the formula (21).
R ₂₄₀₁ to R ₂₄₀₇ are the same as R ₂₂₁ to R ₂₂₇ in formulas (21-1) and (21-2). R ₂₄₁₀ to R ₂₄₁₇ are the same as R ₂₀₁ to R _{211 in} the formula (22). The two R ₂₄₁₇ may be the same as or different from each other. )

In one embodiment, the substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms of the ring A1 in the formula (21-5) is a substituted or unsubstituted naphthalene ring or a substituted or unsubstituted naphthalene ring. It is a fluorene ring.
In one embodiment, the substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms in ring A1 of formula (21-5) is a substituted or unsubstituted dibenzofuran ring, a substituted or unsubstituted carbazole ring, or It is a substituted or unsubstituted dibenzothiophene ring.

In one embodiment, the compound represented by the formula (21) or (22) is selected from the group consisting of compounds represented by the following formulas (21-6-1) to (21-6-7). You.

(In formulas (21-6-1) to (21-6-7),
R ₂₄₂₁ to R ₂₄₂₇ are the same as R ₂₂₁ to R ₂₂₇ in formulas (21-1) and (21-2). R ₂₄₃₀ to R ₂₄₃₇ and R ₂₄₄₁ to R ₂₄₄₄ are the same as R ₂₀₁ to R _{211 in} the formula (22).
X is O, NR ₉₀₁ , or C (R ₉₀₂ ) (R ₉₀₃ ).
R ₉₀₁ to R ₉₀₃ are as defined in the above formula (1). )

In one embodiment, in the compound represented by the formula (22), at least one set of two or more adjacent R ₂₀₁ to R ₂₁₁ is bonded to each other to form a substituted or unsubstituted saturated or unsaturated group. Form a ring. This embodiment will be described in detail below as Expression (25).

(Compound represented by Formula (25))
The compound represented by formula (25) will be described.

(In formula (25),
R ₂₅₁ and R ₂₅₂ , R ₂₅₂ and R ₂₅₃ , R ₂₅₄ and R ₂₅₅ , R ₂₅₅ and R ₂₅₆ , R ₂₅₆ and R ₂₅₇ , R ₂₅₈ and R ₂₅₉ , R ₂₅₉ and R ₂₆₀ , and R ₂₆₀ and R ₂₆₁ Two or more of the pairs selected from the group combine with each other to form a substituted or unsubstituted saturated or unsaturated ring.
However, a pair consisting of R ₂₅₁ and R ₂₅₂ and a pair consisting of R ₂₅₂ and R ₂₅₃ ; a pair consisting of R ₂₅₄ and R ₂₅₅ and a pair consisting of R ₂₅₅ and R ₂₅₆ ; a pair consisting of R ₂₅₅ and R ₂₅₆ and R ₂₅₆ A pair consisting of R ₂₅₇ ; a pair consisting of R ₂₅₈ and R ₂₅₉ and a pair consisting of R ₂₅₉ and R ₂₆₀ ; and a pair consisting of R ₂₅₉ and R ₂₆₀ and a pair consisting of R ₂₆₀ and R ₂₆₁ simultaneously forming a ring. There is no.
Two or more rings formed by R ₂₅₁ to R ₂₆₁ may be the same or different.
R ₂₅₁ to R ₂₆₁ which do not form a substituted or unsubstituted saturated or unsaturated ring are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1). )

In the formula (25), R _n and R _{n + 1} (n represents an integer selected from 251, 252, 254 to 256, and 258 to 260) are bonded to each other to form two rings where R _n and R _{n + 1} are bonded. Together with the forming carbon atom, it forms a substituted or unsubstituted saturated or unsaturated ring. The ring is preferably composed of atoms selected from C, O, S and N atoms, and the number of atoms is preferably 3 to 7, more preferably 5 or 6.

数 The number of the ring structures in the compound represented by the formula (25) is, for example, two, three, or four. The two or more ring structures may each be present on the same benzene ring on the mother skeleton of the formula (25), or may be present on different benzene rings. For example, in the case of having three ring structures, one ring structure may be present in each of the three benzene rings of formula (25).

Examples of the ring structure in the compound represented by the formula (25) include structures represented by the following formulas (251) to (260).

(In the formulas (251) to (257), * 1 and * 2, * 3 and * 4, * 5 and * 6, * 7 and * 8, * 9 and * 10, * 11 and * 12, and * 13 Each of * 14 represents the two ring-forming carbon atoms to which R _n and R _{n + 1} are bonded, and the ring-forming carbon atoms to which R _n is bonded are * 1 and * 2, * 3 and * 4, * 5 and It may be any of the two ring-forming carbon atoms represented by * 6, * 7 and * 8, * 9 and * 10, * 11 and * 12, and * 13 and * 14.
X ₂₅₀₁ is C (R ₂₅₁₂ ) (R ₂₅₁₃ ), NR ₂₅₁₄ , O or S.
One or more adjacent two or more sets of R ₂₅₀₁ to R ₂₅₀₆ and R ₂₅₁₂ to R ₂₅₁₃ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or substituted or unsubstituted. Does not form a substituted saturated or unsaturated ring.
R ₂₅₀₁ to R ₂₅₁₄ which do not form a substituted or unsubstituted saturated or unsaturated ring are the same as R ₂₅₁ to R ₂₆₁ described above. )

(In formulas (258) to (260), * 1 and * 2 and * 3 and * 4 each represent the two ring-forming carbon atoms to which R _n and R _{n + 1} are bonded, and R _n is bonded to The ring-forming carbon atom may be any of the two ring-forming carbon atoms represented by * 1 and * 2 or * 3 and * 4.
X ₂₅₀₁ is C (R ₂₅₁₂ ) (R ₂₅₁₃ ), NR ₂₅₁₄ , O or S.
One or more adjacent two or more sets of R ₂₅₁₅ to R ₂₅₂₅ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated Does not form a ring.
R ₂₅₁₅ to R ₂₅₂₁ and R ₂₅₂₂ to R ₂₅₂₅ which do not form a substituted or unsubstituted saturated or unsaturated ring are the same as R ₂₅₁ to R ₂₆₁ described above. )

In the formula (25), at least one of R ₂₅₂ , R ₂₅₄ , R ₂₅₅ , R ₂₆₀ and R ₂₆₁ (preferably, at least one of R ₂₅₂ , R ₂₅₅ and R ₂₆₀ , more preferably R ₂₅₂ ) is a ring It is preferable that the group does not form a structure.

(I) a substituent in the case where the ring structure formed by R _n and R _{n + 1} in the formula (25) has a substituent;
(Ii) In Formula (25), R ₂₅₁ to R ₂₆₁ that does not form a ring structure, and (iii) R ₂₅₀₁ to R ₂₅₁₄ and R ₂₅₁₅ to R ₂₅₂₅ in Formulas (251) to (260) are preferably Independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
-N (R ₉₀₆ ) (R ₉₀₇ ),
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
It is either a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms, or a group selected from the following group.

(In the formulas (261) to (264), R _d is each independently:
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
X is C (R ₉₀₁ ) (R ₉₀₂ ), NR ₉₀₃ , O or S.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1).
p1 is independently an integer of 0 to 5, p2 is independently an integer of 0 to 4, p3 is an integer of 0 to 3, and p4 is an integer of 0 to 7. )

In one embodiment, the compound represented by the formula (25) is represented by any of the following formulas (25-1) to (25-6).

(In the formulas (25-1) to (25-6), the rings d to i are each independently a substituted or unsubstituted saturated or unsaturated ring. R ₂₅₁ to R ₂₆₁ are the same as those in the formula (25) Same as).)

In one embodiment, the compound represented by formula (25) is represented by any of the following formulas (25-7) to (25-12).

(In the formulas (25-7) to (25-12), rings d to f, k, and j are each independently a substituted or unsubstituted saturated or unsaturated ring. R ₂₅₁ to R ₂₆₁ are This is the same as the equation (25).)

In one embodiment, the compound represented by the formula (25) is represented by any of the following formulas (25-13) to (25-21).

In (Equation (25-13) - (25-21), ring d-k are each independently a ring substituted or unsubstituted, saturated or unsaturated _.R 251 _{- R 261} is the formula (25 Same as).)

When the ring g or h further has a substituent, the substituent is, for example,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
Examples thereof include a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a group represented by the above formula (261), (263) or (264).

In one embodiment, the compound represented by the formula (25) is represented by any of the following formulas (25-22) to (25-25).

(In formulas (25-22) to (25-25), X ₂₅₀ is independently C (R ₉₀₁ ) (R ₉₀₂ ), NR ₉₀₃ , O or S. R ₂₅₁ to R ₂₆₁ , R ₂₇₁ to R ₂₇₈ is the same as R ₂₅₁ to R _{261 in} the above formula (25), and R ₉₀₁ to R ₉₀₃ are as defined in the above formula (1).)

In one embodiment, the compound represented by the formula (25) is represented by the following formula (25-26).

(In the formulas (25-26), X ₂₅₀ is C (R ₉₀₁ ) (R ₉₀₂ ), NR ₉₀₃ , O or S. R ₂₅₃ , R ₂₅₄ , R ₂₅₇ , R ₂₅₈ , R ₂₆₁ , and R ₂₇₁ -R ₂₈₂ are the same as R ₂₅₁ -R _{261 in} the formula (25). R ₉₀₁ -R ₉₀₃ are as defined in the formula (1).)

化合物 Specific examples of the compound represented by the formula (21) include the following compounds. In the following specific examples, Me represents a methyl group.

(Compound represented by Formula (31))
The compound represented by the formula (31) will be described. The compound represented by the formula (31) is a compound corresponding to the compound represented by the formula (21-3) described above.

(In equation (31),
At least one pair of adjacent two or more of R ₃₀₁ to R ₃₀₇ and R ₃₁₁ to R ₃₁₇ forms a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring Does not form a ring.
R ₃₀₁ to R ₃₀₇ and R ₃₁₁ to R ₃₁₇ which do not form a substituted or unsubstituted saturated or unsaturated ring are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₃₂₁ and R ₃₂₂ are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1). )

“One set of two or more adjacent to R ₃₀₁ to R ₃₀₇ and R ₃₁₁ to R ₃₁₇ ” is, for example, R ₃₀₁ and R ₃₀₂ , R ₃₀₂ and R ₃₀₃ , R ₃₀₃ and R ₃₀₄ , R ₃₀₅ and R _306. , R ₃₀₆ and R ₃₀₇ , R ₃₀₁ , R ₃₀₂ and R _{303, and the} like.

In one embodiment, at least one, preferably two of R ₃₀₁ to R ₃₀₇ and R ₃₁₁ to R ₃₁₇ are groups represented by —N (R ₉₀₆ ) (R ₉₀₇ ).

In one embodiment, R ₃₀₁ to R ₃₀₇ and R ₃₁₁ to R ₃₁₇ are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted ring group. It is a monovalent heterocyclic group having 5 to 50 atoms.

In one embodiment, the compound represented by the formula (31) is a compound represented by the following formula (32).

(In equation (32),
One or more of adjacent two or more of R ₃₃₁ to R ₃₃₄ and R ₃₄₁ to R ₃₄₄ form a substituted or unsubstituted saturated or unsaturated ring, or are substituted or unsubstituted saturated or unsaturated. Does not form a ring.
R ₃₃₁ to R ₃₃₄ , R ₃₄₁ to R ₃₄₄ and R ₃₅₁ and R ₃₅₂ which do not form a substituted or unsubstituted saturated or unsaturated ring are each independently
Hydrogen atom,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₃₆₁ to R ₃₆₄ are each independently
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. )

In one embodiment, the compound represented by formula (31) is a compound represented by formula (33) below.

(In the formula (33), R ₃₅₁ , R ₃₅₂ and R ₃₆₁ to R ₃₆₄ are as defined in the formula (32).)

In one embodiment, the compound represented by the formula (31) is a compound represented by the following formula (34) or (35).

(In equations (34) and (35),
R ₃₆₁ to R ₃₆₄ are as defined in the above formula (32).
At least one pair of adjacent two or more of R ₃₇₁ to R ₃₇₇ and R ₃₈₀ to R ₃₈₆ forms a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring Does not form a ring.
R ₃₇₁ to R ₃₇₇ and R ₃₈₀ to R ₃₈₆ , which do not form a substituted or unsubstituted saturated or unsaturated ring, and R ₃₈₇ are each independently
Hydrogen atom,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. The two R ₃₈₇ may be the same as or different from each other. )

In one embodiment, the compound represented by the formula (31) is a compound represented by the following formula (34-2) or (35-2).

(In the formulas (34-2) and (35-2), R ₃₆₁ to R ₃₆₄ , R ₃₇₅ to R ₃₇₇ and R ₃₈₄ to R ₃₈₇ are as defined in the formulas (34) and (35). )

In one embodiment, R ₃₆₁ to R ₃₆₄ in formulas (32), (33), (34), (35), (34-2), and (35-2) are each independently substituted or unsubstituted. Is an aryl group having 6 to 50 ring carbon atoms (preferably a phenyl group).

In one embodiment, R ₃₂₁ and R ₃₂₂ in formula (31) and R ₃₅₁ and R in formulas (32), (33), (34), (35), (34-2), and (35-2). ₃₅₂ is independently a hydrogen atom or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms (preferably a phenyl group).

In one embodiment, the compound represented by formula (31) is a compound represented by formula (36) below.

(In Formula (36), one or more adjacent two or more of R ₃₀₀₁ , R ₃₀₀₂ , R ₃₀₀₅ to R ₃₀₀₇ , R ₃₀₁₀ , R ₃₀₁₁ , R ₃₀₁₄ to R ₃₀₁₆ , and R ₃₀₃₁ to R ₃₀₃₄ are They are joined together to form a substituted or unsubstituted saturated or unsaturated ring, or no substituted or unsubstituted saturated or unsaturated ring.
X _a is independently selected from O, S and N (R ₃₅ ).
R ₃₅ is combined with R ₃₀₃₁ to form a substituted or unsubstituted saturated or unsaturated ring, or does not form the ring.
Wherein _R 3001 which do not form a ring substituted or unsubstituted, saturated or _{_{_{_{unsaturated, R 3002, R 3005 ~ R}}}} 3007, R 3010, R 3011, R 3014 ~ R 3016, and _{_R} 3031 _~ _R _3035, and _{R 3021,} R ₃₀₂₂ is each independently:
Hydrogen atom,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. )

In one embodiment, the substituent in the case of “substituted or unsubstituted” in formulas (31) to (36) is
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

Specific examples of the compound represented by the formula (31) include the compounds shown below. In the following specific examples, Me represents a methyl group.

(Compound represented by Formula (41))
The compound represented by the formula (41) will be described.

(In formula (41),
ring a, ring b and ring c are each independently
A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or
It is a substituted or unsubstituted heterocycle having 5 to 50 ring atoms.
R ₄₀₁ and R ₄₀₂ each independently form a substituted or unsubstituted heterocyclic ring or do not form a substituted or unsubstituted heterocyclic ring by combining with the a ring, the b ring or the c ring.
R ₄₀₁ and R ₄₀₂ which do not form the substituted or unsubstituted heterocyclic ring are each independently
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. )

Ring a, ring b and ring c are each a ring (substituted or unsubstituted aromatic ring having 6 to 50 ring-forming carbon atoms) fused to a central fused bicyclic structure of formula (41) composed of a B atom and two N atoms. Group hydrocarbon ring or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms.

The “aromatic hydrocarbon ring” of ring a, ring b and ring c has the same structure as the above-described compound in which a hydrogen atom has been introduced into the “aryl group”. The “aromatic hydrocarbon ring” of the ring a contains three carbon atoms on the fused bicyclic structure at the center of the formula (41) as ring-forming atoms. The “aromatic hydrocarbon ring” of the ring b and the ring c includes two carbon atoms on the central fused bicyclic structure of the formula (41) as ring-forming atoms. Specific examples of the “substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms” include compounds in which a hydrogen atom has been introduced into the “aryl group” described in Specific Example Group G1.
The “heterocycle” of ring a, ring b and ring c has the same structure as the above-mentioned compound in which a hydrogen atom has been introduced into the “heterocyclic group”. The “heterocycle” of ring a contains three carbon atoms on the condensed two-ring structure in the center of formula (41) as ring-forming atoms. The “heterocycle” of the b-ring and the c-ring includes two carbon atoms on the fused bicyclic structure at the center of the formula (41) as ring-forming atoms. Specific examples of the “substituted or unsubstituted heterocyclic ring having 5 to 50 ring atoms” include compounds in which a hydrogen atom has been introduced into the “heterocyclic group” described in Specific Example Group G2.

R ₄₀₁ and R ₄₀₂ may be independently bonded to ring a, ring b or ring c to form a substituted or unsubstituted heterocyclic ring. The heterocyclic ring in this case will contain a nitrogen atom on the fused bicyclic structure in the center of formula (41). In this case, the heterocyclic ring may contain a hetero atom other than a nitrogen atom. R ₄₀₁ and R ₄₀₂ are bonded to ring a, ring b or ring c, specifically, the atom forming ring a, ring b or ring c is bonded to the atom forming ring R ₄₀₁ or R _402. Means For example, R ₄₀₁ may be bonded to ring a to form a two-ring fused (or three-ring fused or more) nitrogen-containing heterocycle in which the ring containing R ₄₀₁ and the a ring are fused. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to a nitrogen-containing two-ring fused or more heterocyclic group in Specific Example Group G2.
The same _applies to the case where R ₄₀₁ is bonded to ring b, the case where R ₄₀₂ is bonded to ring a, and the case where R ₄₀₂ is bonded to ring c.

In one embodiment, ring a, ring b and ring c in formula (41) are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms.
In one embodiment, ring a, ring b and ring c in formula (41) are each independently a substituted or unsubstituted benzene ring or naphthalene ring.

In one embodiment, R ₄₀₁ and R ₄₀₂ in Formula (41) are each independently a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted ring-forming atom having 5 to 50 ring atoms. And is preferably a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, the compound represented by formula (41) is a compound represented by formula (42) below.

(In equation (42),
R _401A combines with one or more selected from the group consisting of R ₄₁₁ and R ₄₂₁ to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring. R _402A bonds to one or more selected from the group consisting of R ₄₁₃ and R ₄₁₄ to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring.
R _401A and R _402A which do not form a substituted or unsubstituted heterocyclic ring are each independently
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
One or more of adjacent two or more of R ₄₁₁ to R ₄₂₁ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form a ring.
R ₄₁₁ to R ₄₂₁ which do not form the substituted or unsubstituted heterocyclic ring or the substituted or unsubstituted saturated or unsaturated ring are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1). )

R _401A and R _402A in the formula (42) are groups corresponding to R ₄₀₁ and R ₄₀₂ in the formula (41).
For example, R _401A and R ₄₁₁ may combine to form a bicyclic fused (or tricyclic fused or more) nitrogen-containing heterocycle in which a ring containing these and a benzene ring corresponding to ring a are fused. Specific examples of the nitrogen-containing heterocyclic ring include compounds corresponding to a nitrogen-containing two-ring fused or more heterocyclic group in Specific Example Group G2. The same _applies to the case where R _401A and R ₄₁₂ combine, the case where R _402A and R ₄₁₃ combine, and the case where R _402A and R ₄₁₄ combine.

One or more pairs of adjacent two or more of R ₄₁₁ to R ₄₂₁ may be bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring. For example, R ₁₁ and R ₁₂ may be bonded to form a structure in which a benzene ring, an indole ring, a pyrrole ring, a benzofuran ring, a benzothiophene ring, or the like is condensed to a 6-membered ring to which these are bonded, The formed condensed ring becomes a naphthalene ring, a carbazole ring, an indole ring, a dibenzofuran ring or a dibenzothiophene ring.

In one embodiment, R ₄₁₁ to R ₄₂₁ that do not contribute to ring formation are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted ring carbon number having 6 to 50 carbon atoms. Or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

In one embodiment, R ₄₁₁ to R ₄₂₁ that do not contribute to ring formation are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted ring-forming atom number. 5 to 50 monovalent heterocyclic groups.

In one embodiment, R ₄₁₁ to R ₄₂₁ that do not contribute to ring formation are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, R ₄₁₁ to R ₄₂₁ that do not contribute to ring formation are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and at least one of R ₄₁₁ to R ₄₂₁ One is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, the compound represented by the formula (42) is a compound represented by the following formula (43).

(In formula (43),
R ₄₃₁ combines with R ₄₄₆ to form a substituted or unsubstituted heterocyclic ring or does not form a substituted or unsubstituted heterocyclic ring. R ₄₃₃ combines with R ₄₄₇ to form a substituted or unsubstituted heterocyclic ring or does not form a substituted or unsubstituted heterocyclic ring. R ₄₃₄ bonds to R ₄₅₁ to form a substituted or unsubstituted heterocyclic ring, or does not form a substituted or unsubstituted heterocyclic ring. R ₄₄₁ combines with R ₄₄₂ to form a substituted or unsubstituted heterocyclic ring or does not form a substituted or unsubstituted heterocyclic ring.
One or more of adjacent two or more of R ₄₃₁ to R ₄₅₁ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form a ring.
R ₄₃₁ to R ₄₅₁ which do not form the substituted or unsubstituted heterocyclic ring or the substituted or unsubstituted saturated or unsaturated ring are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1). )

R ₄₃₁ may combine with R ₄₄₆ to form a substituted or unsubstituted heterocycle. For example, R ₄₃₁ and R ₄₄₆ combine to form a 3- or more-fused nitrogen-containing heterocycle in which the benzene ring to which R ₄₆ is attached, the ring containing N, and the benzene ring corresponding to ring a are fused. You may. Specific examples of the nitrogen-containing heterocycle include compounds corresponding to a nitrogen-containing three-ring fused or more heterocyclic group in Specific Example Group G2. The same _applies to the case where R ₄₃₃ and R ₄₄₇ are bonded, the case where R ₄₃₄ and R ₄₅₁ are bonded, and the case where R ₄₄₁ and R ₄₄₂ are bonded.

In one embodiment, R ₄₃₁ to R ₄₅₁ which do not contribute to ring formation are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted ring-forming carbon number 6 to 50. Or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

In one embodiment, R ₄₃₁ to R ₄₅₁ that do not contribute to ring formation are each independently a hydrogen atom, a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted ring-forming atom number. 5 to 50 monovalent heterocyclic groups.

In one embodiment, R ₄₃₁ to R ₄₅₁ that do not contribute to ring formation are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, R ₄₃₁ to R ₄₅₁ that do not contribute to ring formation are each independently a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, and at least one of R ₄₃₁ to R ₄₅₁ is _preferred. One is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, the compound represented by the formula (43) is a compound represented by the following formula (43A).

(In the formula (43A),
R ₄₆₁ is
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
It is a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
R ₄₆₂ to R ₄₆₅ are each independently
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
It is a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. )

In one embodiment, R ₄₆₁ to R ₄₆₅ are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, R ₄₆₁ to R ₄₆₅ are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

In one embodiment, the compound represented by the formula (43) is a compound represented by the following formula (43B).

(In equation (43B),
R ₄₇₁ and R ₄₇₂ are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—N (R ₉₀₆ ) (R ₉₀₇ ) or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
R ₄₇₃ to R ₄₇₅ are each independently
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—N (R ₉₀₆ ) (R ₉₀₇ ) or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
R ₉₀₆ and R ₉₀₇ are as defined in the above formula (1). )

In one embodiment, the compound represented by the formula (43) is a compound represented by the following formula (43B ′).

(In the formula (43B ′), R ₄₇₂ to R ₄₇₅ are as defined in the formula (43B).)

In one embodiment, at least one of R ₄₇₁ to R ₄₇₅ is
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—N (R ₉₀₆ ) (R ₉₀₇ ) or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment,
R ₄₇₂ is
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
—N (R ₉₀₆ ) (R ₉₀₇ ), or a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms,
R ₄₇₁ and R ₄₇₃ to R ₄₇₅ are each independently
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
—N (R ₉₀₆ ) (R ₉₀₇ ) or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, the compound represented by the formula (43) is a compound represented by the following formula (43C).

(In the formula (43C),
R ₄₈₁ and R ₄₈₂ are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
It is a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
R ₄₈₃ to R ₄₈₆ are each independently
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
It is a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. )

In one embodiment, the compound represented by the formula (43) is a compound represented by the following formula (43C ′).

(In the formula (43C ′), R ₄₈₃ to R ₄₈₆ are as defined in the formula (43C).)

In one embodiment, R ₄₈₁ to R ₄₈₆ are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, R ₄₈₁ to R ₄₈₆ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

The compound represented by the formula (41) is prepared as an intermediate by first connecting the a ring, b ring and c ring with a linking group (a group containing NR ₁ and a group containing NR ₂ ). (First reaction), the final product can be produced by bonding ring a, ring b and ring c with a linking group (group containing B) (second reaction). In the first reaction, an amination reaction such as a Bhabhurt-Hartwig reaction can be applied. In the second reaction, a tandem hetero Friedel-Crafts reaction or the like can be applied.

Hereinafter, specific examples of the compound represented by the formula (41) will be described, but these are merely examples, and the compound represented by the formula (41) is not limited to the following specific examples. In the following specific examples, Me represents a methyl group and tBu represents a tert-butyl group.

(Compound represented by Formula (51))
The compound represented by the formula (51) will be described.

(In equation (51),
The r ring is a ring represented by the formula (52) or the formula (53) fused at an arbitrary position of an adjacent ring.
The q ring and the s ring are each independently a ring represented by the formula (54) fused at an arbitrary position of an adjacent ring.
The p-ring and the t-ring each have a structure represented by the formula (55) or (56), which is independently condensed at an arbitrary position of an adjacent ring.
If R ₅₀₁ there are a plurality and do not form a plurality of adjacent R ₅₀₁ is bonded to either form a ring substituted or unsubstituted, saturated or unsaturated with one another, or a substituted or unsubstituted saturated or unsaturated ring .
X ₅₀₁ is an oxygen atom, a sulfur atom, or NR ₅₀₂ .
R ₅₀₁ and R ₅₀₂ which do not form a substituted or unsubstituted saturated or unsaturated ring are
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1).
Ar ₅₀₁ and Ar ₅₀₂ are each independently
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
L ₅₀₁ is
A substituted or unsubstituted alkylene group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenylene group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynylene group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkylene group having 3 to 50 ring carbon atoms,
A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
m1 is each independently an integer of 0 to 2, m2 is each independently an integer of 0 to 4, m3 is each independently an integer of 0 to 3, and m4 is each independently 0 to 2. It is an integer of 5. If R ₅₀₁ there are a plurality to plurality of R ₅₀₁ may be the same as each other or may be different. )

において In the formula (51), each of the rings p to t is fused by sharing two carbon atoms with an adjacent ring. The position and direction of condensation are not limited, and condensation can be performed at any position and direction.

In one embodiment, in Formula (52) or Formula (53) for the r-ring, R ₅₀₁ is a hydrogen atom.

In one embodiment, the compound represented by the formula (51) is represented by any of the following formulas (51-1) to (51-6).

(In the formulas (51-1) to (51-6), R ₅₀₁ , X ₅₀₁ , Ar ₅₀₁ , Ar ₅₀₂ , L ₅₀₁ , m1 and m3 are as defined in the formula (51).)

In one embodiment, the compound represented by the formula (51) is represented by any of the following formulas (51-11) to (51-13).

(In Formulas (51-11) to (51-13), R ₅₀₁ , X ₅₀₁ , Ar ₅₀₁ , Ar ₅₀₂ , L ₅₀₁ , m1, m3, and m4 are as defined in Formula (51).)

In one embodiment, the compound represented by the formula (51) is represented by any of the following formulas (51-21) to (51-25).

(In the formulas (51-21) to (51-25), R ₅₀₁ , X ₅₀₁ , Ar ₅₀₁ , Ar ₅₀₂ , L ₅₀₁ , m1 and m4 are as defined in the formula (51).)

In one embodiment, the compound represented by the formula (51) is represented by any of the following formulas (51-31) to (51-33).

(In the formulas (51-31) to (51-33), R ₅₀₁ , X ₅₀₁ , Ar ₅₀₁ , Ar ₅₀₂ , L ₅₀₁ , and m2 to m4 are as defined in the formula (51).)

In one embodiment, Ar ₅₀₁ and Ar ₅₀₂ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, one of Ar ₅₀₁ and Ar ₅₀₂ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and the other is a substituted or unsubstituted monovalent monovalent having 5 to 50 ring atom atoms. It is a heterocyclic group.

化合物 Specific examples of the compound represented by the formula (51) include the following compounds. In the following specific examples, Me represents a methyl group.

(Compound represented by Formula (61))
The compound represented by the formula (61) will be described.

(In equation (61),
At least one pair of R ₆₀₁ and R ₆₀₂ , R ₆₀₂ and R ₆₀₃ , and R ₆₀₃ and R ₆₀₄ combine with each other to form a divalent group represented by the following formula (62).
At least one pair of R ₆₀₅ and R ₆₀₆ , R ₆₀₆ and R ₆₀₇ , and R ₆₀₇ and R ₆₀₈ combine with each other to form a divalent group represented by the following formula (63).

Of R ₆₀₁ to R ₆₀₄ , those which do not form a divalent group represented by the above formula (62), and at least one of R ₆₁₁ to R ₆₁₄ are monovalent groups represented by the following formula (64) .
Among R ₆₀₅ to R ₆₀₈ , those which do not form the divalent group represented by the above formula (63), and at least one of R ₆₂₁ to R ₆₂₄ are monovalent groups represented by the following formula (64). .
X ₆₀₁ is an oxygen atom, a sulfur atom, or NR ₆₀₉ .
R ₆₀₁ to R ₆₀₈ , which do not form the divalent group represented by the formulas (62) and (63) and are not the monovalent group represented by the formula (64), the formula (64) R ₆₁₁ to R ₆₁₄ and R ₆₂₁ to R ₆₂₄ , and R ₆₀₉ which are not a monovalent group represented by
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1).

In the formula (64), Ar ₆₀₁ and Ar ₆₀₂ are each independently:
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
L ₆₀₁ to L ₆₀₃ are independently
Single bond,
A substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms, or a divalent linking group formed by combining 2 to 4 of these. )

In the formula (61), the positions where the divalent group represented by the formula (62) and the divalent group represented by the formula (63) are formed are not particularly limited, and the positions where R ₆₀₁ to R ₆₀₈ are possible Such groups can be formed.

In one embodiment, the compound represented by the formula (61) is represented by any of the following formulas (61-1) to (61-6).

(In the formulas (61-1) to (61-6), X ₆₀₁ is as defined in the formula (61).
At least two of R ₆₀₁ to R ₆₂₄ are monovalent groups represented by the above formula (64).
R ₆₀₁ to R ₆₂₄ which are not a monovalent group represented by the formula (64) are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1). )

In one embodiment, the compound represented by the formula (61) is represented by any of the following formulas (61-7) to (61-18).

(In the formulas (61-7) to (61-18), X ₆₀₁ is as defined in the formula (61). * Represents a single bond bonded to the monovalent group represented by the formula (64). R ₆₀₁ to R ₆₂₄ are the same as R ₆₀₁ to R ₆₂₄ which are not a monovalent group represented by the formula (64).

R ₆₀₁ to R ₆₀₈ which do not form the divalent group represented by the formulas (62) and (63) and are not the monovalent group represented by the formula (64); R ₆₁₁ to R ₆₁₄ and R ₆₂₁ to R ₆₂₄ which are not monovalent groups represented by 64) are preferably each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

The monovalent group represented by the formula (64) is preferably represented by the following formula (65) or (66).

(In the formula (65), R ₆₃₁ to R ₆₄₀ are independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1). )

(In the formula (66), Ar ₆₀₁ , L ₆₀₁ and L ₆₀₃ are as defined in the above formula (64). HAr ₆₀₁ is a structure represented by the following formula (67).

In the formula (67), X ₆₀₂ is an oxygen atom or a sulfur atom.
Any one of R ₆₄₁ to R ₆₄₈ is a single bond bonded to L ₆₀₃ .
R ₆₄₁ to R ₆₄₈ which are not a single bond are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1). )

As the compound represented by the formula (61), in addition to the compounds described in International Publication 2014/104144, for example, the compounds shown below can be mentioned as specific examples. In the following specific examples, Me represents a methyl group.

(Compound represented by Formula (71))
The compound represented by the formula (71) will be described.

(In equation (71),
A ₇₀₁ ring and A ₇₀₂ ring are each independently
A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or
It is a substituted or unsubstituted heterocycle having 5 to 50 ring atoms.
At least one selected from the group consisting of the ring A _{701 and the} ring A ₇₀₂ bonds to a bond * of a structure represented by the following formula (72).

In equation (72),
A ₇₀₃ rings are each independently:
A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or
It is a substituted or unsubstituted heterocycle having 5 to 50 ring atoms.
X ₇₀₁ is NR ₇₀₃ , C (R ₇₀₄ ) (R ₇₀₅ ), Si (R ₇₀₆ ) (R ₇₀₇ ), Ge (R ₇₀₈ ) (R ₇₀₉ ), O, S or Se.
R ₇₀₁ and R ₇₀₂ combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.
R ₇₀₁ and R ₇₀₂ which do not form a substituted or unsubstituted saturated or unsaturated ring, and R ₇₀₃ to R ₇₀₉ are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1). )

At least one selected from the group consisting of the ring A _{701 and the} ring A ₇₀₂ bonds to a bond * of the structure represented by the formula (72). That is, in one embodiment, the ring-forming carbon atoms of the aromatic hydrocarbon ring A ₇₀₁ ring, or ring-forming atoms of the heterocycle, binds to bond structure represented by the formula (72) *. Also, in one embodiment, the ring-forming carbon atoms of the aromatic hydrocarbon ring A ₇₀₂ ring, or ring-forming atoms of the heterocycle, binds to bond structure represented by the formula (72) *.

In one _embodiment, the group represented by the following formula (73) to one or both of the _{A 701} ring and _{A 702} ring is bonded.

(In the formula (73), Ar ₇₀₁ and Ar ₇₀₂ are each independently
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
L ₇₀₁ to L ₇₀₃ are each independently
Single bond,
A substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms, or a divalent linking group formed by combining 2 to 4 of these. )

In one embodiment, in addition to the ring A ₇₀₁ , the ring-forming carbon atom of the aromatic hydrocarbon ring of the ring A ₇₀₂ or the ring-forming atom of the heterocyclic ring has a bond of a structure represented by the formula (72). Combine with *. In this case, the structures represented by formula (72) may be the same or different.

In one embodiment, R ₇₀₁ and R ₇₀₂ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In one embodiment, R ₇₀₁ and R ₇₀₂ combine with each other to form a fluorene structure.

In one embodiment, Ring A ₇₀₁ and Ring A ₇₀₂ are a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring.

In one embodiment, ring A ₇₀₃ is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, for example, a substituted or unsubstituted benzene ring.
In one embodiment, X ₇₀₁ is O or S.

Specific examples of the compound represented by the formula (71) include the compounds shown below. In the following specific examples, Me represents a methyl group.

(Compound represented by Formula (81))
The compound represented by the formula (81) will be described.

(In equation (81),
The ring A ₈₀₁ is a ring represented by the formula (82) fused at an arbitrary position of an adjacent ring.
The ring A ₈₀₂ is a ring represented by the formula (83) fused at an arbitrary position of an adjacent ring. The two bonding hands * bond to an arbitrary position on the _A803 ring.
X ₈₀₁ and X ₈₀₂ are each independently C (R ₈₀₃ ) (R ₈₀₄ ), Si (R ₈₀₅ ) (R ₈₀₆ ), an oxygen atom, or a sulfur atom.
Ring A ₈₀₃ is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms.
Ar ₈₀₁ is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
R ₈₀₁ to R ₈₀₆ are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
—O— (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R ₉₀₁ to R ₉₀₇ are as defined in the above formula (1).
m801 and m802 are each independently an integer of 0 to 2. When these are 2, a plurality of R ₈₀₁ or R ₈₀₂ may be the same as or different from each other.
a801 is an integer of 0 to 2. When a801 is 0 or 1, the structures in parentheses represented by “3-a801” may be the same or different. If a801 is _2, to _{Ar 801} may be the same as each other or may be different. )

In one embodiment, Ar ₈₀₁ is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.

In one embodiment, ring A ₈₀₃ is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, such as a substituted or unsubstituted benzene ring, a substituted or unsubstituted naphthalene ring, or It is a substituted or unsubstituted anthracene ring.

In one embodiment, R ₈₀₃ and R ₈₀₄ are each independently a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.

において In one embodiment, a801 is 1.

Specific examples of the compound represented by the formula (81) include the compounds shown below.

The content of the compound (host material) represented by the formula (1) in the light emitting layer is preferably 80% by mass or more and 99% by mass or less based on the entire light emitting layer. In addition, one or more compounds (dopant materials) selected from the group consisting of formulas (11), (21), (31), (41), (51), (61), (71) and (81) The content in the light emitting layer is preferably 1% by mass or more and 20% by mass or less based on the entire light emitting layer.

Hereinafter, members that can be used in the organic EL element according to one embodiment of the present invention and materials other than the above compounds, which constitute each layer, will be described.

(substrate)
The substrate is used as a support for the light emitting device. As the substrate, for example, glass, quartz, plastic, or the like can be used. Alternatively, a flexible substrate may be used. The flexible substrate is a substrate that can be bent (flexible), and examples thereof include a plastic substrate made of polycarbonate and polyvinyl chloride.

(anode)
It is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a large work function (specifically, 4.0 eV or more) for the anode formed on the substrate. Specifically, for example, indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, and indium oxide containing zinc oxide , Graphene and the like. In addition, gold (Au), platinum (Pt), a nitride of a metal material (for example, titanium nitride), and the like are given.

(Hole injection layer)
The hole-injection layer is a layer containing a substance having a high hole-injection property. Materials having a high hole-injecting property include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, Tungsten oxide, manganese oxide, aromatic amine compounds, or high molecular compounds (oligomers, dendrimers, polymers, and the like) can also be used.

(Hole transport layer)
The hole-transporting layer is a layer containing a substance having a high hole-transporting property. An aromatic amine compound, a carbazole derivative, an anthracene derivative or the like can be used for the hole transport layer. A high molecular compound such as poly (N-vinylcarbazole) (abbreviation: PVK) or poly (4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. However, any substance other than these substances may be used as long as it has a property of transporting more holes than electrons. Note that the layer containing a substance having a high hole-transport property is not limited to a single layer, and may be a layer in which two or more layers of the above substances are stacked.

(Guest material of the light emitting layer)
The light-emitting layer is a layer containing a substance having a high light-emitting property, and various materials can be used. For example, as the substance having a high light emitting property, a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used. The fluorescent compound is a compound capable of emitting light from a singlet excited state, and the phosphorescent compound is a compound capable of emitting light from a triplet excited state.
As a blue fluorescent light-emitting material that can be used for the light-emitting layer, a pyrene derivative, a styrylamine derivative, a chrysene derivative, a fluoranthene derivative, a fluorene derivative, a diamine derivative, a triarylamine derivative, or the like can be used. As a green fluorescent light emitting material that can be used for the light emitting layer, an aromatic amine derivative or the like can be used. As a red fluorescent light emitting material that can be used for the light emitting layer, a tetracene derivative, a diamine derivative, or the like can be used.
As a blue phosphorescent material that can be used for the light-emitting layer, a metal complex such as an iridium complex, an osmium complex, and a platinum complex is used. An iridium complex or the like is used as a green phosphorescent material that can be used for the light emitting layer. A metal complex such as an iridium complex, a platinum complex, a terbium complex, or a europium complex is used as a red phosphorescent light emitting material that can be used for the light emitting layer.

(The host material of the light emitting layer)
The light-emitting layer may have a structure in which the above substance having a high light-emitting property (guest material) is dispersed in another substance (host material). As a substance for dispersing a substance having a high light-emitting property, various substances can be used, the lowest unoccupied orbital level (LUMO level) is higher than the substance having a high light-emitting property, and the highest occupied orbital level ( It is preferable to use a substance having a low HOMO level).
As a substance (host material) for dispersing a substance having a high light-emitting property, 1) a metal complex such as an aluminum complex, a beryllium complex, or a zinc complex; 2) an oxadiazole derivative, a benzimidazole derivative, or a phenanthroline derivative; A heterocyclic compound, 3) a condensed aromatic compound such as a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, or a chrysene derivative; 3) an aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative; used.

(Electron transport layer)
The electron-transporting layer is a layer containing a substance having a high electron-transporting property. In the electron transport layer, 1) a metal complex such as an aluminum complex, a beryllium complex or a zinc complex, 2) a heteroaromatic compound such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative or a phenanthroline derivative, 3) a polymer compound Can be used.

(Electron injection layer)
The electron-injection layer is a layer containing a substance having a high electron-injection property. For the electron injection layer, lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), 8-hydroxyquinolinolato-lithium (Liq), etc. Or an alkali metal such as lithium oxide (LiO _x ), an alkaline earth metal, or a compound thereof.

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

方法 In the organic EL element according to one embodiment of the present invention, a method for forming each layer is not particularly limited. A conventionally known formation method such as a vacuum evaporation method and a spin coating method can be used. Each layer such as a light-emitting layer is formed by a known method such as a vacuum evaporation method, a molecular beam evaporation method (MBE method), or a dipping method of a solution dissolved in a solvent, a spin coating method, a casting method, a bar coating method, a roll coating method, or the like. It can be formed by a method.

In the organic EL element according to one embodiment of the present invention, the thickness of each layer is not particularly limited, but is generally from several nm to suppress defects such as pinholes, suppress applied voltage, and improve luminous efficiency. A range of 1 μm is preferred.

[Electronics]
An electronic device according to one embodiment of the present invention includes the organic EL element according to one embodiment of the present invention.
Specific examples of the electronic device include a display component such as an organic EL panel module, a display device such as a television, a mobile phone, or a personal computer, and a light emitting device such as a lighting device or a vehicular lamp.

Next, the present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited to the description of these Examples.

Synthesis Example 1 [Synthesis of Compound BH-1]
(Synthesis of Intermediate 1)
Under argon atmosphere, 13.3-g (50.0 mmol) of 9-bromoanthracene-d9, 6.4 g (52.5 mmol) of phenylboronic acid, 1.2 g (1.00 mmol) of Pd [PPh ₃ ] _{4 in} 75 ml of toluene and dimethoxy. 75 ml of ethane and 75 ml (150.0 mmol) of a 2M Na ₂ CO ₃ aqueous solution were added, and the mixture was heated under reflux with stirring for 10 hours.
After completion of the reaction, the mixture was cooled to room temperature, transferred to a separating funnel and extracted with dichloromethane. The organic phase was dried over MgSO ₄ , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 10.9 g of white solid. The obtained compound was subjected to FD-MS analysis and identified as the following intermediate 1 (yield 83%).

(Synthesis of Intermediate 2)
A solution prepared by dissolving 5.3 g (20.0 mmol) of Intermediate 1 in 120 ml of dichloromethane was added dropwise to a solution prepared by dissolving 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane at room temperature and stirred for 1 hour. did.
After the reaction was completed, the sample was transferred to a separating funnel and washed with a 2M Na ₂ S ₂ O ₃ aqueous solution. Furthermore, the organic phase was washed with 10% Na ₂ CO ₃ and then with water, and the separated organic phase was dried over MgSO ₄ , filtered and concentrated.
The concentrated residue was dispersed in methanol (100 ml) and the precipitated crystals were obtained to obtain 6.5 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as the following intermediate 2 (yield 95%).

(Synthesis of Compound BH-1)
Under an argon atmosphere, 1.7 g (5.0 mmol) of intermediate 2, 1.4 g (5.3 mmol) of benzo [b] naphtho [2,3-d] furan-2-boronic acid, Pd [PPh ₃ ] ₄₀ To 0.1 g (0.1 mmol), 7.5 ml of toluene, 7.5 ml of dimethoxyethane, and 7.5 ml (15.0 mmol) of a 2M Na ₂ CO ₃ aqueous solution were added, and the mixture was heated under reflux with stirring for 10 hours.
After completion of the reaction, the mixture was cooled to room temperature, transferred to a separating funnel and extracted with dichloromethane. The organic phase was dried over MgSO ₄ , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 1.7 g of white solid. The obtained compound was subjected to FD-MS analysis and identified as the following compound BH-1 (yield 70%).

Synthesis Example 2 [Synthesis of Compound BH-2]
(Synthesis of Intermediate 3)
Under an argon atmosphere, 13.3-g (50.0 mmol) of 9-bromoanthracene-d9, 9.0 g (52.5 mmol) of 1-naphthaleneboronic acid, 1.2 g (1.00 mmol) of Pd [PPh ₃ ] ₄ and 75 ml of toluene. , Dimethoxyethane (75 ml) and a 2M Na ₂ CO ₃ aqueous solution (75 ml, 150.0 mmol) were added, and the mixture was heated under reflux with stirring for 10 hours.
After completion of the reaction, the mixture was cooled to room temperature, transferred to a separating funnel and extracted with dichloromethane. The organic phase was dried over MgSO ₄ , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 13.3 g of white solid. The obtained compound was subjected to FD-MS analysis and identified as the following intermediate 3 (yield 85%).

(Synthesis of Intermediate 4)
A solution prepared by dissolving 6.3 g (20.0 mmol) of Intermediate 3 in 120 ml of dichloromethane was added dropwise to a solution prepared by dissolving 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane at room temperature and stirred for 1 hour. did.
After the reaction was completed, the sample was transferred to a separating funnel and washed with a 2M Na ₂ S ₂ O ₃ aqueous solution. Furthermore, the organic phase was washed with 10% Na ₂ CO ₃ and then with water three times. The organic phase was dried over MgSO ₄ , filtered and concentrated.
The concentrated residue was dispersed in methanol (100 mL) to precipitate crystals, and 7.5 g of a white solid was obtained. The obtained compound was subjected to FD-MS analysis and identified as the following intermediate 4 (yield 96%).

(Synthesis of Compound BH-2)
Under an argon atmosphere, 2.0 g (5.0 mmol) of intermediate ₄ , 1.4 g (5.3 mmol) of benzo [b] naphtho [2,3-d] furan-2-boronic acid, Pd [PPh ₃ ] ₄₀ To 0.1 g (0.1 mmol), 7.5 ml of toluene, 7.5 ml of dimethoxyethane, 7.5 ml (15.0 mmol) of 2M Na ₂ CO ₃ aqueous solution were added, and the mixture was heated under reflux with stirring for 10 hours.
After completion of the reaction, the mixture was cooled to room temperature, transferred to a separating funnel and extracted with dichloromethane. The organic phase was dried over MgSO ₄ , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 1.9 g of white solid. The obtained compound was subjected to FD-MS analysis and identified as the following compound BH-2 (yield 73%).

Synthesis Example 3 [Synthesis of Compound BH-3]
(Synthesis of Intermediate 5)
Under an argon atmosphere, 13.3-g (50.0 mmol) of 9-bromoanthracene-d9, 13.0 g (52.5 mmol) of 4- (1-naphthyl) phenylboronic acid, and 1.2 g of Pd [PPh ₃ ] ₄ (1. (00 mmol), 75 ml of toluene, 75 ml of dimethoxyethane, and 75 ml (150.0 mmol) of a 2M Na ₂ CO ₃ aqueous solution were added, and the mixture was heated under reflux with stirring for 10 hours.
After completion of the reaction, the mixture was cooled to room temperature, transferred to a separating funnel and extracted with dichloromethane. The organic phase was dried over MgSO ₄ , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 15.6 g of white solid. The obtained compound was subjected to FD-MS analysis and identified as the following intermediate 5 (yield 80%).

(Synthesis of Intermediate 6)
Intermediate 5: A solution prepared by dissolving 7.8 g (20.0 mmol) of dichloromethane in 120 ml of dichloromethane was added dropwise to a solution prepared by dissolving 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane at room temperature and stirred for 1 hour. did.
After the reaction was completed, the sample was transferred to a separating funnel and washed with a 2M Na ₂ S ₂ O ₃ aqueous solution. Furthermore, the organic phase was washed with 10% Na ₂ CO ₃ and then with water three times. The organic phase was dried over MgSO ₄ , filtered and concentrated.
The concentrated residue was dispersed in methanol (100 ml) and the precipitated crystals were collected to obtain 8.6 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as the following intermediate 6 (yield 92%).

(Synthesis of Compound BH-3)
Under an argon atmosphere, 2.3 g (5.0 mmol) of intermediate 6, 1.4 g (5.3 mmol) of benzo [b] naphtho [2,3-d] furan-2-boronic acid, Pd [PPh ₃ ] ₄₀ To 0.1 g (0.1 mmol), 7.5 ml of toluene, 7.5 ml of dimethoxyethane, and 7.5 ml (15.0 mmol) of a 2M Na ₂ CO ₃ aqueous solution were added, and the mixture was heated under reflux with stirring for 10 hours.
After completion of the reaction, the mixture was cooled to room temperature, transferred to a separating funnel and extracted with dichloromethane. The organic phase was dried over MgSO ₄ , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 2.1 g of a white solid. The obtained compound was identified by the following compound BH-3 by FD-MS analysis (yield 68%).

Synthesis Example 4 [Synthesis of Compound BH-4]
In Synthesis Example 1, 1.4 g (5%) of benzo [b] naphtho [1,2-d] furan-10-boronic acid was used instead of benzo [b] naphtho [2,3-d] furan-2-boronic acid. The reaction was performed in the same manner as above except that 1.7 g of white crystals were obtained. The obtained compound was subjected to FD-MS analysis and identified as the following compound BH-4 (yield 71%).

Synthesis Example 5 [Synthesis of Compound BH-5]
In Synthesis Example 1, benzo [b] naphtho [2,1-d] furan-8-boronic acid was replaced by 1.4 g (5 .3 mmol) was used, and the reaction was performed in the same manner to obtain 1.6 g of white crystals. The obtained compound was subjected to FD-MS analysis and identified as the following compound BH-5 (yield 65%).

Synthesis Example 6 [Synthesis of Compound BH-6]
In Synthesis Example 1, benzo [b] naphtho [2,3-d] furan-1-boronic acid was replaced by 1.4 g (5 .3 mmol) was used, and the same reaction was performed to obtain 1.4 g of white crystals. The obtained compound was subjected to FD-MS analysis and identified as the following compound BH-6 (yield 57%).

Synthesis Example 7 [Synthesis of Compound BH-7]
(Synthesis of Intermediate 7)
Under an argon atmosphere, 13.3-g (50.0 mmol) of 9-bromoanthracene-d9, 10.4 g (52.5 mmol) of 3-biphenylboronic acid, 1.2 g (1.00 mmol) of Pd [PPh ₃ ] ₄ and 75 ml of toluene. , Dimethoxyethane (75 ml) and a 2M Na ₂ CO ₃ aqueous solution (75 ml, 150.0 mmol) were added, and the mixture was heated under reflux with stirring for 10 hours.
After completion of the reaction, the mixture was cooled to room temperature, transferred to a separating funnel and extracted with dichloromethane. The organic phase was dried over MgSO ₄ , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 13.6 g of white solid. The obtained compound was subjected to FD-MS analysis and identified as the following intermediate 7 (yield 80%).

(Synthesis of Intermediate 8)
Intermediate 7: A solution prepared by dissolving 6.8 g (20.0 mmol) of dichloromethane in 120 ml of dichloromethane was added dropwise to a solution prepared by dissolving 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane at room temperature and stirred for 1 hour. did.
After the reaction was completed, the sample was transferred to a separating funnel and washed with a 2M Na ₂ S ₂ O ₃ aqueous solution. Furthermore, the organic phase was washed with 10% Na ₂ CO ₃ and then with water three times. The organic phase was dried over MgSO ₄ , filtered and concentrated.
The concentrated residue was dispersed in methanol (100 mL) and the precipitated crystals were obtained to obtain 8.0 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as the following intermediate 8 (yield 96%).

(Synthesis of Compound BH-7)
Under an argon atmosphere, 2.1 g (5.0 mmol) of intermediate 8, 1.4 g (5.3 mmol) of benzo [b] naphtho [2,3-d] furan-1-boronic acid, Pd [PPh ₃ ] ₄₀ To 0.1 g (0.1 mmol), 7.5 ml of toluene, 7.5 ml of dimethoxyethane, and 7.5 ml (15.0 mmol) of a 2M Na ₂ CO ₃ aqueous solution were added, and the mixture was heated under reflux with stirring for 10 hours.
After completion of the reaction, the mixture was cooled to room temperature, transferred to a separating funnel and extracted with dichloromethane. The organic phase was dried over MgSO ₄ , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 1.7 g of white solid. The obtained compound was subjected to FD-MS analysis and identified as the following compound BH-7 (yield 60%).

Synthesis Example 8 [Synthesis of Compound BH-8]
In Synthesis Example 1, benzo [b] naphtho [2,1-d] furan-7-boronic acid was replaced by 1.4 g (5 .3 mmol) was used, and the reaction was performed in the same manner to obtain 1.6 g of white crystals. The obtained compound was subjected to FD-MS analysis and identified as the following compound BH-8 (yield 65%).

Synthesis Example 9 [Synthesis of Compound BH-9]
(Synthesis of Intermediate 9)
Under an argon atmosphere, 13.3-g (50.0 mmol) of 9-bromoanthracene-d9, 10.4 g (52.5 mmol) of 4-biphenylboronic acid, 1.2 g (1.00 mmol) of Pd [PPh ₃ ] ₄ and 75 ml of toluene. , Dimethoxyethane (75 ml) and a 2M Na ₂ CO ₃ aqueous solution (75 ml, 150.0 mmol) were added, and the mixture was heated under reflux with stirring for 10 hours.
After completion of the reaction, the mixture was cooled to room temperature, transferred to a separating funnel and extracted with dichloromethane. The organic phase was dried over MgSO ₄ , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 14.1 g of white solid. The obtained compound was subjected to FD-MS analysis and identified as the following intermediate 9 (yield 83%).

(Synthesis of Intermediate 10)
A solution prepared by dissolving 6.8 g (20.0 mmol) of Intermediate 9 in 120 ml of dichloromethane was added dropwise to a solution prepared by dissolving 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane at room temperature and stirred for 1 hour. did.
After the reaction was completed, the sample was transferred to a separating funnel and washed with a 2M Na ₂ S ₂ O ₃ aqueous solution. Furthermore, the organic phase was washed with 10% Na ₂ CO ₃ and then with water three times. The organic phase was dried over MgSO ₄ , filtered and concentrated.
The concentrated residue was dispersed in methanol (100 mL) and the precipitated crystals were obtained to obtain 8.0 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as the following intermediate 10 (yield 96%).

(Synthesis of Compound BH-9)
Under an argon atmosphere, 2.1 g (5.0 mmol) of intermediate 10, 1.4 g (5.3 mmol) of benzo [b] naphtho [2,3-d] furan-1-boronic acid, Pd [PPh ₃ ] ₄₀ To 0.1 g (0.1 mmol), 7.5 ml of toluene, 7.5 ml of dimethoxyethane, and 7.5 ml (15.0 mmol) of a 2M Na ₂ CO ₃ aqueous solution were added, and the mixture was heated under reflux with stirring for 10 hours.
After completion of the reaction, the mixture was cooled to room temperature, transferred to a separating funnel and extracted with dichloromethane. The organic phase was dried over MgSO ₄ , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 1.4 g of white solid. The obtained compound was subjected to FD-MS analysis and identified as the following compound BH-9 (yield 51%).

Synthesis Example 10 [Synthesis of Compound BH-10]
In Synthesis Example 7, benzo [b] naphtho [2,1-d] furan-7-boronic acid was replaced with 1.4 g (5%) instead of benzo [b] naphtho [2,3-d] furan-1-boronic acid. .3 mmol) was used, and the same reaction was performed to obtain 1.4 g of white crystals. The obtained compound was subjected to FD-MS analysis and identified as the following compound BH-10 (yield 52%).

Synthesis Example 11 [Synthesis of Compound BH-11]
In Synthesis Example 1, 3- (benzo [b] naphtho [2,3-d] furan-1-yl) phenylboronic acid was used instead of benzo [b] naphtho [2,3-d] furan-2-boronic acid. Was reacted in the same manner except that 1.8 g (5.3 mmol) was used, 1.5 g of white crystals were obtained. The obtained compound was subjected to FD-MS analysis and identified as the following compound BH-11 (yield 53%).

Synthesis Example 12 [Synthesis of Compound BH-12]
(Synthesis of Intermediate 11)
Under an argon atmosphere, 13.3-g (50.0 mmol) of 9-bromoanthracene-d9, 10.4 g (52.5 mmol) of 2-biphenylboronic acid, 1.2 g (1.00 mmol) of Pd [PPh ₃ ] ₄ and 75 ml of toluene. , Dimethoxyethane (75 ml) and a 2M Na ₂ CO ₃ aqueous solution (75 ml, 150.0 mmol) were added, and the mixture was heated under reflux with stirring for 10 hours.
After completion of the reaction, the mixture was cooled to room temperature, transferred to a separating funnel and extracted with dichloromethane. The organic phase was dried over MgSO ₄ , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 10.9 g of white solid. The obtained compound was subjected to FD-MS analysis and identified as the following Intermediate 11 (yield 64%).

(Synthesis of Intermediate 12)
A solution prepared by dissolving 6.8 g (20.0 mmol) of Intermediate 11 in 120 ml of dichloromethane was added dropwise to a solution prepared by dissolving 3.2 g (20.0 mmol) of bromine in 12 ml of dichloromethane at room temperature and stirred for 1 hour. did.
After the reaction was completed, the sample was transferred to a separating funnel and washed with a 2M Na ₂ S ₂ O ₃ aqueous solution. Furthermore, the organic phase was washed with 10% Na ₂ CO ₃ and then with water three times. The organic phase was dried over MgSO ₄ , filtered and concentrated.
The concentrated residue was dispersed in methanol (100 mL) and the precipitated crystals were obtained to obtain 8.0 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as the following intermediate 12 (yield 96%).

(Synthesis of Compound BH-12)
Under an argon atmosphere, 2.1 g (5.0 mmol) of intermediate 12, 1.4 g (5.3 mmol) of benzo [b] naphtho [2,3-d] furan-2-boronic acid, Pd [PPh ₃ ] ₄₀ To 0.1 g (0.1 mmol), 7.5 ml of toluene, 7.5 ml of dimethoxyethane, and 7.5 ml (15.0 mmol) of a 2M Na ₂ CO ₃ aqueous solution were added, and the mixture was heated under reflux with stirring for 10 hours.
After completion of the reaction, the mixture was cooled to room temperature, transferred to a separating funnel and extracted with dichloromethane. The organic phase was dried over MgSO ₄ , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 1.7 g of white solid. The obtained compound was subjected to FD-MS analysis and identified as the following compound BH-12 (yield 60%).

Synthesis Example 13 [Synthesis of Compound BH-13]
In Synthesis Example 1, 1.4 g (5%) of benzo [b] naphtho [2,1-d] furan-6-boronic acid was used instead of benzo [b] naphtho [2,3-d] furan-2-boronic acid. .3 mmol) was used, and the reaction was performed in the same manner to obtain 1.2 g of white crystals. The obtained compound was subjected to FD-MS analysis and identified as the following compound BH-13 (yield 50%).

Synthesis Example 14 [Synthesis of Compound BH-14]
In Synthesis Example 1, 4- (benzo [b] naphtho [2,3-d] furan-1-yl) phenylboronic acid was used instead of benzo [b] naphtho [2,3-d] furan-2-boronic acid. Was reacted in the same manner except that 1.8 g (5.3 mmol) was used, 1.5 g of white crystals were obtained. The obtained compound was subjected to FD-MS analysis and identified as the following compound BH-14 (yield 55%).

Synthesis Example 15 [Synthesis of Compound BH-15]
(Synthesis of Intermediate 13)
1.33 g (5.00 mmol) of 9-bromoanthracene-d9, 0.67 g (5.25 mmol) of phenyl-d5-boronic acid, 0.12 g (0.10 mmol) of Pd [PPh ₃ ] ₄ and toluene in an argon atmosphere. 7.5 ml, 7.5 ml of dimethoxyethane, 7.5 ml (15.0 mmol) of a 2M Na ₂ CO ₃ aqueous solution were added, and the mixture was heated under reflux with stirring for 10 hours.
After completion of the reaction, the mixture was cooled to room temperature, transferred to a separating funnel and extracted with dichloromethane. The organic phase was dried over MgSO ₄ , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 1.07 g of white solid. The obtained compound was subjected to FD-MS analysis and identified as the following Intermediate 13 (yield 80%).

(Synthesis of Intermediate 14)
A solution obtained by dissolving 1.07 g (4.0 mmol) of Intermediate 13 in 25 ml of dichloromethane was added dropwise to a solution prepared by dissolving 0.64 g (4.0 mmol) of bromine in 3 ml of dichloromethane at room temperature and stirred for 1 hour. did.
After the reaction was completed, the sample was transferred to a separating funnel and washed with a 2M Na ₂ S ₂ O ₃ aqueous solution. Further, the organic phase was washed with 10% Na ₂ CO ₃ and then with water, and the separated organic phase was dried over MgSO ₄ , filtered and concentrated.
The concentrated residue was dispersed in methanol (100 ml) to precipitate crystals, and 1.3 g of a white solid was obtained. The obtained compound was subjected to FD-MS analysis and identified as the following intermediate 14 (yield 95%).

(Synthesis of Compound BH-15)
Under argon atmosphere, 0.87 g (2.5 mmol) of intermediate 14, 0.69 g (2.65 mmol) of benzo [b] naphtho [2,3-d] furan-2-boronic acid, Pd [PPh ₃ ] ₄₀ To 0.06 g (0.05 mmol), 5 ml of toluene, 5 ml of dimethoxyethane, and 5 ml (10.0 mmol) of a 2M Na ₂ CO ₃ aqueous solution were added, and the mixture was heated under reflux with stirring for 10 hours.
After completion of the reaction, the mixture was cooled to room temperature, transferred to a separating funnel and extracted with dichloromethane. The organic phase was dried over MgSO ₄ , filtered and concentrated. The concentrated residue was purified by silica gel column chromatography to obtain 0.87 g of white solid. The obtained compound was subjected to FD-MS analysis and identified as the following compound BH-15 (yield 72%).

Synthesis Example 16 [Synthesis of Compound BH-16]
In Synthesis Example 2, benzo [b] naphtho [1,2-d] furan-10-boronic acid was replaced with 1.4 g (5 .3 mmol) was used and the reaction was carried out in the same manner to obtain 1.5 g of white crystals. The obtained compound was subjected to FD-MS analysis and identified as the following compound BH-16 (yield 56%).

Example 1
(Production of organic EL element)
A 25 mm × 75 mm × 1.1 mm thick glass substrate with ITO transparent electrode (anode) (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes, and then UV ozone cleaning for 30 minutes. The film thickness of ITO was 130 nm.
The cleaned glass substrate with a transparent electrode is mounted on a substrate holder of a vacuum vapor deposition apparatus, and a compound HI is vapor-deposited so that the transparent electrode is first covered on the surface on which the transparent electrode is formed to form a HI film having a thickness of 5 nm. A film was formed. This HI film functions as a hole injection layer.
Following the formation of this HI film, the compound HT-1 was vapor-deposited to form an HT-1 film having a film thickness of 80 nm on the HI film. This HT-1 film functions as a hole transport layer (first hole transport layer).
After forming the HT-1 film, a compound HT-2 was deposited, and a 10 nm-thick HT-2 film was formed on the HT-1 film. This HT-2 film functions as an electron blocking layer (second hole transport layer).
Compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated on the HT-2 film so that the ratio of compound BD-1 was 4% by mass, and BH-1 having a film thickness of 25 nm: A BD-1 film was formed. This BH-1: BD-1 film functions as a light emitting layer.

Compound ET-1 was deposited on this light emitting layer to form a 10 nm-thick ET-1 film. This ET-1 film functions as a hole barrier layer.
Compound ET-2 was deposited on the ET-1 film to form a 15 nm-thick ET-2 film. This ET-2 film functions as an electron transport layer. LiF was deposited on the ET-2 film to form a 1 nm-thick LiF film. Metal Al was vapor-deposited on this LiF film to form a metal cathode having a film thickness of 80 nm, and an organic EL device was produced.

The layer structure of the obtained organic EL device is as follows.
ITO (130) / HI (5) / HT-1 (80) / HT-2 (10) / BH-1: BD-1 (25: 4% by mass) / ET-1 (10) / ET-2 ( 15) / LiF (1) / Al (80)
The numbers in parentheses indicate the film thickness (unit: nm).

The materials used in Example 1 and Examples and Comparative Examples described later are shown below.

(Evaluation of organic EL element)
A voltage was applied to the obtained organic EL device so that the current density was 50 mA / cm ^2, and the time (LT95 (unit: hour)) until the brightness reached 95% of the initial brightness was measured. The results are shown in Table 1.
Further, the CIE1931 chromaticity coordinates (CIEx, CIEy) when a voltage was applied to the obtained organic EL device so that the current density became 10 mA / cm ² were measured using a spectral radiance meter CS-1000 (Konica Minolta, Inc.). Was used to obtain and measure the spectral radiance spectrum. The results are shown in Table 1.

Comparative Examples 1-1 and 1-2
An organic EL device was prepared and evaluated by the same method as in Example 1 except that the compounds shown in the following table were used as the host material of the light emitting layer. The results are shown in Table 1.

Example 2 and Comparative Example 2
An organic EL device was prepared and evaluated by the same method as in Example 1 except that the compounds shown in the following table were used as the host material of the light emitting layer. Table 2 shows the results.

Example 3, Comparative Examples 3-1 and 3-2
An organic EL device was prepared and evaluated by the same method as in Example 1 except that the compounds shown in the following table were used as the host material of the light emitting layer. The results are shown in Table 3.

Example 4, Comparative Example 4-1, Comparative Example 4-2
An organic EL device was prepared and evaluated by the same method as in Example 1 except that the compounds shown in the following table were used as the host material of the light emitting layer. The results are shown in Table 4.

Example 5, Comparative Example 5
An organic EL device was prepared and evaluated by the same method as in Example 1 except that the compounds shown in the following table were used as the host material of the light emitting layer. Table 5 shows the results.

Example 6, Comparative Example 6
An organic EL device was prepared and evaluated by the same method as in Example 1 except that the compounds shown in the following table were used as the host material of the light emitting layer. The results are shown in Table 6.

Example 11 and Comparative Example 11
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). Table 7 shows the results.

Example 12, Comparative Example 12
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). Table 8 shows the results.

Example 13, Comparative Example 13
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 9.

Example 14, Comparative Example 14
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 10.

Example 15 and Comparative Example 15
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 11.

Example 16, Comparative Example 16
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 12.

Example 17, Comparative Example 17
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 13.

Example 18, Comparative Example 18
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 14.

Example 21, Comparative Example 21
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 15.

Example 22, Comparative Example 22
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 16.

Example 23, Comparative Example 23
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 17.

Example 24, Comparative Example 24
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 18.

Example 25, Comparative Example 25
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 19.

Example 26, Comparative Example 26
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 20.

Example 27, Comparative Example 27
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 21.

Example 28, Comparative Example 28
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 22.

Example 31, Comparative Example 31
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 23.

Example 32, Comparative Example 32
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 24.

Example 33, Comparative Example 33
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 25.

Example 34, Comparative Example 34
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 26.

Example 35, Comparative Example 35
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 27.

Example 36, Comparative Example 36
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 28.

Example 37, Comparative Example 37
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 29.

Example 38, Comparative Example 38
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 30.

Example 41, Comparative Example 41
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 31.

Example 42, Comparative Example 42
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 32.

Example 43, Comparative Example 43
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 33.

Example 44, Comparative Example 44
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 34.

Example 45, Comparative Example 45
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 35.

Example 46, Comparative Example 46
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 36.

Example 47, Comparative Example 47
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 37.

Example 48, Comparative Example 48
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 38.

Example 51, Comparative Example 51
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 39.

Example 52, Comparative Example 52
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 40.

Example 53, Comparative Example 53
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 41.

Example 54, Comparative Example 54
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 42.

Example 55, Comparative Example 55
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 43.

Example 56, Comparative Example 56
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 44.

Example 57, Comparative Example 57
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 45.

Example 58, Comparative Example 58
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 46.

Example 61, Comparative Example 61
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 47.

Example 62, Comparative Example 62
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 48.

Example 63, Comparative Example 63
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 49.

Example 64, Comparative Example 64
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 50.

Example 65, Comparative Example 65
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 51.

Example 66, Comparative Example 66
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 52.

Example 67, Comparative example 67
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 53.

Example 68, Comparative Example 68
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 54.

Example 69, Comparative example 69
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 55.

Example 70, Comparative Example 70
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 56.

Example 71, Comparative example 71
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 57.

Example 72, Comparative Example 72
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 58.

Example 73, Comparative Example 73
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 59.

Example 74, Comparative Example 74
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 60.

Example 75, Comparative Example 75
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 61.

Example 76, Comparative Example 76
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 62.

Example 77
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 63.

Example 78, Comparative Example 78
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 64.

Comparative Example 79
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 65.

Example 80, Comparative Example 80
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 66.

Example 81, Comparative Example 81
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 67.

Example 82, Comparative Example 82
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 68.

Example 83, Comparative Example 83
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 69.

Example 84, Comparative Example 84
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 70.

Example 85, Comparative Example 85
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 71.

Example 86
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 72.

Example 87, Comparative Example 87
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 73.

Comparative Example 88
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 74.

Example 89, Comparative Example 89
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 75.

Example 90, Comparative Example 90
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 76.

Example 91, Comparative example 91
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 77.

Example 92, Comparative Example 92
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 78.

Example 93, Comparative Example 93
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 79.

Example 94, Comparative example 94
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 80.

Example 95
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 81.

Example 96, Comparative Example 96
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 82.

Comparative Example 97
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 83.

Example 98, Comparative Example 98
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 84.

Example 99, Comparative Example 99
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 85.

Example 100, Comparative example 100
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 86.

Example 101, Comparative Example 101
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 87.

Example 102, Comparative Example 102
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 88.

Example 103, Comparative Example 103
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 89.

Example 104
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 90.

Example 105, Comparative Example 105
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 91.

Comparative Example 106
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 92.

Example 107, Comparative Example 107
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 93.

Example 108, Comparative Example 108
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 94.

Example 109, Comparative Example 109
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 95.

Example 110, Comparative Example 110
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 96.

Example 111, Comparative Example 111
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 97.

Example 112, Comparative example 112
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 98.

Example 113
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 99.

Example 114, Comparative example 114
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 100.

Comparative Example 115
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 101.

Example 116, Comparative Example 116
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 102.

Example 117, Comparative Example 117
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 103.

Example 118, Comparative example 118
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 104.

Example 119, Comparative Example 119
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 105.

Example 120, Comparative Example 120
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 106.

Example 121, Comparative Example 121
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 107.

Example 122
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 108.

Example 123, Comparative Example 123
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 109.

Comparative Example 124
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 110.

Example 125, Comparative Example 125
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 111.

Example 126, Comparative example 126
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 112.

Example 127, Comparative Example 127
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 113.

Example 128, Comparative Example 128
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 114.

Example 129, Comparative Example 129
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 115.

Example 130, Comparative Example 130
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 116.

Example 131
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 117.

Example 132, Comparative example 132
An organic EL device was prepared and evaluated in the same manner as in Example 1 except that the compounds shown in the following table were used as the light emitting layer materials (host material and dopant material). The results are shown in Table 118.

From the results of Tables 1 to 118, when the compound of the present invention having a deuterium atom at a specific site is used in the light emitting layer of the organic EL device, it is more organic than when a compound having no deuterium atom at the site is used. It can be seen that the life of the EL element is extended. Further, from the comparison between Example 3 and Comparative Example 3-2, even if the compound has a deuterium atom at a specific site, it is possible to extend the life of the organic EL element by adopting the structure of the present invention. I understand.

While certain embodiments and / or examples of the invention have been described in detail above, those skilled in the art will recognize those exemplary embodiments and / or examples without departing substantially from the novel teachings and advantages of the invention. It is easy to make many changes to the embodiments. Accordingly, many of these changes are within the scope of the invention.
The entire contents of the documents and the application based on the Paris Convention priority of the present application are incorporated herein by reference.

Claims

A compound represented by the following formula (1).

(In equation (1),
R 1 to R 8 are each independently:
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R 901 ) (R 902 ) (R 903 ),
—O— (R 904 ),
-S- (R 905 ),
-N (R 906 ) (R 907 ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more R 901 to R 907 exist, each of the two or more R 901 to R 907 may be the same or different.
At least one of R 1 to R 8 is a deuterium atom.
Two or more of R 1 to R 4 and two or more of R 5 to R 8 are not bonded to each other to form a ring.
L 1 and L 2 are each independently:
Single bond,
It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atom (s).
Ar 1 is
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
Ar 2 is a monovalent group represented by the following formula (2), (3) or (4).

In formulas (2) to (4),
Two or more adjacent pairs of R 15 to R 20 are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring is formed. Do not form.
When two or more adjacent pairs of R 15 to R 20 are not bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, one of R 13 to R 20 is L 2 Is a single bond that binds to.
When two or more adjacent pairs of R 15 to R 20 are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, the substituted or unsubstituted saturated or unsaturated ring is R 15 to R 20 that are not formed, and one of R 13 and R 14 is a single bond that is bonded to L 2 .
R 13 to R 20 , which do not form a substituted or unsubstituted saturated or unsaturated ring and which are not a single bond bonded to L 2 , and R 11 and R 12 are each independently,
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R 901 ) (R 902 ) (R 903 ),
—O— (R 904 ),
-S- (R 905 ),
-N (R 906 ) (R 907 ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are as defined in the above formula (1). )
The compound according to claim 1, wherein at least two of R 1 to R 8 are deuterium atoms.
The compound according to claim 1 or 2, wherein R 1 to R 8 are all deuterium atoms.
One or more selected from the group consisting of L 1 and L 2 is an unsubstituted arylene group having 6 to 30 ring carbon atoms in which at least one hydrogen atom is a deuterium atom, or at least one hydrogen atom is deuterium. The compound according to any one of claims 1 to 3, which is an unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms.
The compound according to any one of claims 1 to 4, wherein L 1 and L 2 are each independently a single bond or a substituted or unsubstituted arylene group having 6 to 14 ring-forming carbon atoms.
The compound according to any one of claims 1 to 5, wherein R 13 or R 14 is a single bond that bonds to L 2 .
The compound according to any one of claims 1 to 6, wherein two or more adjacent pairs of R 15 to R 20 do not bond with each other to form a substituted or unsubstituted saturated or unsaturated ring.
Ar 1 is an unsubstituted aryl group having 6 to 50 ring-forming carbon atoms in which at least one of hydrogen atoms is a deuterium atom, or an unsubstituted aryl group having 5 to 5 ring atoms in which at least one of hydrogen atoms is a deuterium atom. The compound according to any one of claims 1 to 7, which is 50 monovalent heterocyclic groups.
9. The compound according to claim 1, wherein Ar 1 is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
The compound according to claim 9, wherein Ar 1 is selected from groups represented by the following formulas (a1) to (a4).

(In the formulas (a1) to (a4), * represents a single bond bonded to L 1 .
R 21 is
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R 901 ) (R 902 ) (R 903 ),
—O— (R 904 ),
-S- (R 905 ),
-N (R 906 ) (R 907 ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are as defined in the above formula (1).
m1 is an integer of 0 to 4.
m2 is an integer of 0 to 5.
m3 is an integer of 0 to 7.
When each of m1 to m3 is 2 or more, a plurality of R 21's may be the same as or different from each other.
When m1 to m3 are each 2 or more, a plurality of adjacent R 21 are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form. )
At least one of R 13 to R 20 , which does not form a substituted or unsubstituted saturated or unsaturated ring, and which is not a single bond bonding to L 2 , and R 11 and R 12 , is a deuterium atom. Item 11. A compound according to any one of items 1 to 10.
The compound represented by the formula (1) is represented by the following formula (1-1), (1-2), (1-3), (1-4), (1-5) or (1-6). The compound according to claim 1, which is a compound to be treated.

(In the formulas (1-1), (1-2), (1-3), (1-4), (1-5) and (1-6), R 1 to R 8 and R 11 to R 20 , Ar 1 , L 1 and L 2 are as defined in the above formula (1).)
The compound represented by the formula (1) is represented by the following formula (1-11), (1-12), (1-13), (1-14), (1-15) or (1-16). The compound according to claim 1, which is a compound to be treated.

(In the formulas (1-11), (1-12), (1-13), (1-14), (1-15) and (1-16), R 1 to R 8 , Ar 1 and L 1 Is as defined in the above formula (1).)
The compound represented by the formula (1) is represented by the following formula (1-21), (1-22), (1-23), (1-24), (1-25) or (1-26). The compound according to claim 1, which is a compound to be treated.

(In the formulas (1-21), (1-22), (1-23), (1-24), (1-25) and (1-26), Ar 1 and L 1 are the same as those in the formula (1). ) Is as defined in.)
The compound according to any one of claims 1 to 14, which is a material for an organic electroluminescence device.
A composition comprising the compound according to any one of claims 1 to 15, which is represented by the formula (1) except that the compound represented by the formula (1) and only a light hydrogen atom as a hydrogen atom are contained. The composition containing 99 mol% or less of the latter relative to the total of the compound described above and a compound having the same structure.
A cathode,
An anode,
One or more organic layers disposed between the cathode and the anode,
Have
An organic electroluminescence device, wherein at least one layer of the organic layers contains the compound according to any one of claims 1 to 15 or the composition according to claim 16.
The organic electroluminescent device according to claim 17, wherein the organic layer includes a light emitting layer, and the light emitting layer includes the compound.
The light emitting layer further comprises one or more compounds selected from the group consisting of the following formulas (11), (21), (31), (41), (51), (61), (71) and (81). The organic electroluminescence device according to claim 17, which comprises:

(In equation (11),
One or more adjacent two or more of R 101 to R 110 are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring; Does not form a ring.
At least one of R 101 to R 110 is a monovalent group represented by the following formula (12).
R 101 to R 110 which do not form a substituted or unsubstituted saturated or unsaturated ring and which are not a monovalent group represented by the following formula (12) are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R 901 ) (R 902 ) (R 903 ),
—O— (R 904 ),
-S- (R 905 ),
-N (R 906 ) (R 907 ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are as defined in the above formula (1).

In the formula (12), Ar 101 and Ar 102 are each independently:
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
L 101 to L 103 are independently
Single bond,
It is a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring atom (s). )

(In formula (21),
Z is each independently CR a or N.
The A1 ring and the A2 ring are each independently a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms.
When plural R a are present, one or more adjacent two or more sets of plural R a are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or substituted or Does not form an unsubstituted saturated or unsaturated ring.
When a plurality of R b are present, one or more pairs of adjacent two or more of the plurality of R b are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or Does not form an unsubstituted saturated or unsaturated ring.
When a plurality of R c is present, one or more adjacent two or more sets of the plurality of R c are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or substituted or Does not form an unsubstituted saturated or unsaturated ring.
n21 and n22 are each independently an integer of 0 to 4.
R a to R c which do not form a substituted or unsubstituted saturated or unsaturated ring are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R 901 ) (R 902 ) (R 903 ),
—O— (R 904 ),
-S- (R 905 ),
-N (R 906 ) (R 907 ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are as defined in the above formula (1). )

(In equation (31),
At least one pair of adjacent two or more of R 301 to R 307 and R 311 to R 317 forms a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring Does not form a ring.
R 301 to R 307 and R 311 to R 317 which do not form a substituted or unsubstituted saturated or unsaturated ring are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R 901 ) (R 902 ) (R 903 ),
—O— (R 904 ),
-S- (R 905 ),
-N (R 906 ) (R 907 ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 321 and R 322 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R 901 ) (R 902 ) (R 903 ),
—O— (R 904 ),
-S- (R 905 ),
-N (R 906 ) (R 907 ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are as defined in the above formula (1). )

(In formula (41),
ring a, ring b and ring c are each independently
A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or
It is a substituted or unsubstituted heterocycle having 5 to 50 ring atoms.
R 401 and R 402 each independently form a substituted or unsubstituted heterocyclic ring or do not form a substituted or unsubstituted heterocyclic ring by combining with the a ring, the b ring or the c ring.
R 401 and R 402 which do not form the substituted or unsubstituted heterocyclic ring are each independently
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. )

(In equation (51),
The r ring is a ring represented by the formula (52) or the formula (53) fused at an arbitrary position of an adjacent ring.
The q ring and the s ring are each independently a ring represented by the formula (54) fused at an arbitrary position of an adjacent ring.
The p-ring and the t-ring each have a structure represented by the formula (55) or (56), which is independently condensed at an arbitrary position of an adjacent ring.
If R 501 there are a plurality and do not form a plurality of adjacent R 501 is bonded to either form a ring substituted or unsubstituted, saturated or unsaturated with one another, or a substituted or unsubstituted saturated or unsaturated ring .
X 501 is an oxygen atom, a sulfur atom, or NR 502 .
R 501 and R 502 which do not form a substituted or unsubstituted saturated or unsaturated ring are
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R 901 ) (R 902 ) (R 903 ),
—O— (R 904 ),
-S- (R 905 ),
-N (R 906 ) (R 907 ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are as defined in the above formula (1).
Ar 501 and Ar 502 are each independently
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
L 501 is
A substituted or unsubstituted alkylene group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenylene group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynylene group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkylene group having 3 to 50 ring carbon atoms,
A substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring-forming atoms.
m1 is an integer of 0 to 2, m2 is an integer of 0 to 4, m3 is each independently an integer of 0 to 3, and m4 is each independently an integer of 0 to 5. If R 501 there are a plurality to plurality of R 501 may be the same as each other or may be different. )

(In equation (61),
At least one pair of R 601 and R 602 , R 602 and R 603 , and R 603 and R 604 combine with each other to form a divalent group represented by the following formula (62).
At least one pair of R 605 and R 606 , R 606 and R 607 , and R 607 and R 608 combine with each other to form a divalent group represented by the following formula (63).

Of R 601 to R 604 , those which do not form a divalent group represented by the above formula (62), and at least one of R 611 to R 614 are monovalent groups represented by the following formula (64) .
Among R 605 to R 608 , those which do not form the divalent group represented by the above formula (63), and at least one of R 621 to R 624 are monovalent groups represented by the following formula (64). .
X 601 is an oxygen atom, a sulfur atom, or NR 609 .
R 601 to R 608 , which do not form the divalent group represented by the formulas (62) and (63) and are not the monovalent group represented by the formula (64), the formula (64) R 611 to R 614 and R 621 to R 624 , and R 609 which are not a monovalent group represented by
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R 901 ) (R 902 ) (R 903 ),
—O— (R 904 ),
-S- (R 905 ),
-N (R 906 ) (R 907 ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are as defined in the above formula (1).

In the formula (64), Ar 601 and Ar 602 are each independently:
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
L 601 to L 603 are independently
Single bond,
A substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms,
A substituted or unsubstituted divalent heterocyclic group having 5 to 30 ring-forming atoms, or a divalent linking group formed by combining 2 to 4 of these. )

(In equation (71),
A 701 ring and A 702 ring are each independently
A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or
It is a substituted or unsubstituted heterocycle having 5 to 50 ring atoms.
At least one selected from the group consisting of the ring A 701 and the ring A 702 bonds to a bond * of a structure represented by the following formula (72).

In equation (72),
A 703 rings are each independently:
A substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring carbon atoms, or
It is a substituted or unsubstituted heterocycle having 5 to 50 ring atoms.
X 701 is NR 703 , C (R 704 ) (R 705 ), Si (R 706 ) (R 707 ), Ge (R 708 ) (R 709 ), O, S or Se.
R 701 and R 702 combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or do not form a substituted or unsubstituted saturated or unsaturated ring.
R 701 and R 702 which do not form a substituted or unsubstituted saturated or unsaturated ring, and R 703 to R 709 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R 901 ) (R 902 ) (R 903 ),
—O— (R 904 ),
-S- (R 905 ),
-N (R 906 ) (R 907 ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are as defined in the above formula (1). )

(In equation (81),
The ring A 801 is a ring represented by the formula (82) fused at an arbitrary position of an adjacent ring.
The ring A 802 is a ring represented by the formula (83) fused at an arbitrary position of an adjacent ring. The two bonding hands * bond to an arbitrary position on the A803 ring.
X 801 and X 802 are each independently C (R 803 ) (R 804 ), Si (R 805 ) (R 806 ), an oxygen atom, or a sulfur atom.
Ring A 803 is a substituted or unsubstituted aromatic hydrocarbon ring having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted heterocyclic ring having 5 to 50 ring-forming atoms.
Ar 801 is a substituted or unsubstituted aryl group having 6 to 50 ring-forming carbon atoms or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.
R 801 to R 806 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R 901 ) (R 902 ) (R 903 ),
—O— (R 904 ),
-S- (R 905 ),
-N (R 906 ) (R 907 ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are as defined in the above formula (1).
m801 and m802 are each independently an integer of 0 to 2. When these are 2, a plurality of R 801 or R 802 may be the same as or different from each other.
a801 is an integer of 0 to 2. When a801 is 0 or 1, the structures in parentheses represented by “3-a801” may be the same or different. If a801 is 2, to Ar 801 may be the same as each other or may be different. )
The organic electroluminescence device according to claim 19, wherein in the formula (11), two of R 101 to R 110 are groups represented by the formula (12).
The organic electroluminescent device according to claim 19 or 20, wherein the compound represented by the formula (11) is a compound represented by the following formula (13).

(In the formula (13), R 111 to R 118 are the same as R 101 to R 110 in the formula (11), which are not the monovalent group represented by the formula (12). Ar 101 and Ar 102 , L 101 , L 102, and L 103 are as defined in the above formula (12).)
The organic electroluminescence device according to claim 21, wherein the compound represented by the formula (13) is a compound represented by the following formula (14).

(In the formula (14), R 111 to R 118 are as defined in the formula (13). Ar 101 , Ar 102 , L 102 and L 103 are as defined in the formula (12). .)
The organic electroluminescence device according to claim 21, wherein the compound represented by the formula (13) is a compound represented by the following formula (15).

(In the formula (15), R 111 to R 118 are as defined in the formula (13). Ar 101 and Ar 102 are as defined in the formula (12).)
The organic electroluminescence device according to claim 21, wherein the compound represented by the formula (13) is a compound represented by the following formula (17).

(In the formula (17), R 111 to R 118 are as defined in the formula (13).
One or more of two or more of R 121 to R 127 are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form a ring.
R 121 to R 127 which do not form a substituted or unsubstituted saturated or unsaturated ring are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R 901 ) (R 902 ) (R 903 ),
—O— (R 904 ),
-S- (R 905 ),
-N (R 906 ) (R 907 ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are as defined in the above formula (1).
R 131 to R 135 are each independently
Hydrogen atom,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
A substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
A substituted or unsubstituted cycloalkyl group having 3 to 50 ring-forming carbon atoms,
—Si (R 901 ) (R 902 ) (R 903 ),
—O— (R 904 ),
-S- (R 905 ),
-N (R 906 ) (R 907 ),
Halogen atom, cyano group, nitro group,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
R 901 to R 907 are as defined in the above formula (1). )
25. The organic electroluminescence device according to claim 17, further comprising a hole transport layer between the anode and the light emitting layer.
The organic electroluminescent element according to any one of claims 17 to 25, which has an electron transport layer between the cathode and the light emitting layer.
An electronic device comprising the organic electroluminescent element according to any one of claims 17 to 26.