JP2022022632A - Compound and organic electroluminescent device - Google Patents

Abstract

To provide a compound that can produce an organic EL device having a long service life.SOLUTION: The present invention discloses a compound represented by the formula (1). At least one of a hydrogen atom included in R1-R10 and L1-L4, a hydrogen atom included in Ar1-Ar4, a hydrogen atom included in a substituent in the case of L1-L4 being substituted, and a hydrogen atom included in a substituent in the case of Ar1-Ar4 being substituted is a deuterium atom.SELECTED DRAWING: None

Description

The present invention relates to novel compounds and organic electroluminescence devices.

When a voltage is applied to an organic electroluminescence element (hereinafter, may be referred to as an 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.

The element performance of the conventional organic EL element has not been sufficient yet. Although the materials used for organic EL devices are being gradually improved in order to improve the device performance, further improvement in performance is required. In particular, improvement of the life of an organic EL element is an important issue that leads to the life of a practically used product, and therefore, a material capable of realizing an organic EL element having a long life is required.

Patent Documents 1 and 2 disclose that a compound having a specific structure is used in the light emitting layer of an organic EL device.

International Publication No. 2018/235953 International Publication No. 2014/104144

An object of the present invention is to provide a compound capable of producing an organic EL device having a long life.

（式（１）において、
Ｒ_１～Ｒ_１０は、水素原子である。
Ｌ_１～Ｌ_４は、それぞれ独立に、
単結合、
置換もしくは無置換の環形成炭素数６～５０のアリーレン基、又は
置換もしくは無置換の環形成原子数５～５０の２価の複素環基である。
Ｌ_１及びＬ_２は、互いに単結合で結合するか、あるいは互いに単結合で結合しない。
Ｌ_３及びＬ_４は、互いに単結合で結合するか、あるいは互いに単結合で結合しない。
Ａｒ_１～Ａｒ_４は、それぞれ独立に、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
Ｌ_１及びＬ_２が単結合である場合、Ａｒ_１及びＡｒ_２は、互いに単結合で結合するか、あるいは互いに単結合で結合しない。
Ｌ_３及びＬ_４が単結合である場合、Ａｒ_３及びＡｒ_４は、互いに単結合で結合するか、あるいは互いに単結合で結合しない。
「置換もしくは無置換の」という場合における置換基は、
無置換の炭素数１～５０のアルキル基、
無置換の炭素数２～５０のアルケニル基、
無置換の炭素数２～５０のアルキニル基、
無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ_９０１）（Ｒ_９０２）（Ｒ_９０３）、
－Ｏ－（Ｒ_９０４）、
－Ｓ－（Ｒ_９０５）、
－Ｎ（Ｒ_９０６）（Ｒ_９０７）
（ここで、Ｒ_９０１～Ｒ_９０７は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ_９０１～Ｒ_９０７が２個以上存在する場合、２個以上のＲ_９０１～Ｒ_９０７のそれぞれは同一でもよく、異なっていてもよい。）、
ハロゲン原子、シアノ基、ニトロ基、
無置換の環形成炭素数６～５０のアリール基、及び
無置換の環形成原子数５～５０の１価の複素環基
からなる群から選択される。
Ｒ_１～Ｒ_１０、Ｌ_１～Ｌ_４が有する水素原子、Ａｒ_１～Ａｒ_４が有する水素原子、Ｌ_１～Ｌ_４が置換されている場合の置換基が有する水素原子、及びＡｒ_１～Ａｒ_４が置換されている場合の置換基が有する水素原子のうち１つ以上は、重水素原子である。） As a result of diligent research to achieve the above object, the present inventors have found that a compound having a specific structure can be used to obtain an organic EL element having a long life, and completed the present invention.
According to the present invention, the following compounds and the like are provided.
A compound represented by the following formula (1).

(In equation (1)
R ₁ to R ₁₀ are hydrogen atoms.
L ₁ to L ₄ are independent of each other.
Single bond,
It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
L ₁ and L ₂ are either single-bonded to each other or not single-bonded to each other.
L ₃ and L ₄ are either single-bonded to each other or not single-bonded to each other.
Ar ₁ to Ar ₄ are independent of each other.
It is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a monovalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
When L ₁ and L ₂ are single bonds, Ar ₁ and Ar ₂ either bind to each other in a single bond or do not bind to each other in a single bond.
When L ₃ and L ₄ are single bonds, Ar ₃ and Ar ₄ either bind to each other in a single bond or do not bind to each other in a single bond.
The substituent in the case of "substituent or unsubstituted" is
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,
-Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
-O- (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ )
(Here, R ₉₀₁ to R ₉₀₇ are independent of each other.
Hydrogen atom,
Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms,
It is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a monovalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms. When two or more R ₉₀₁ to R ₉₀₇ are present, 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 selected from the group consisting of an aryl group having an unsubstituted ring-forming carbon number of 6 to 50 and a monovalent heterocyclic group having an unsubstituted ring-forming atom number of 5 to 50.
Hydrogen atoms of R ₁ to R ₁₀ , L ₁ to L ₄ , hydrogen atoms of Ar ₁ to Ar ₄ , hydrogen atoms of substituents when L ₁ to L ₄ are substituted, and Ar ₁ to Ar. One or more of the hydrogen atoms of the substituent when ₄ is substituted is a deuterium atom. )

According to the present invention, it is possible to provide a compound capable of producing an organic EL device having a long life.

It is a figure which shows the schematic structure of the organic EL element which concerns on one aspect of this invention.

[Definition]
As used herein, hydrogen atom includes isotopes having different numbers of neutrons, that is, hydrogen (protium), deuterium (deuterium), and tritium (tritium).

In the present specification, a hydrogen atom, that is, a light hydrogen atom, a heavy hydrogen atom, or a hydrogen atom is located at a bondable position in which a symbol such as "R" or "D" representing a deuterium atom is not specified in the chemical structural formula. It is assumed that the triple hydrogen atom is bonded.

In the present specification, the number of ring-forming carbons constitutes the ring itself of a compound having a structure in which atoms are cyclically bonded (for example, a monocyclic compound, a fused ring compound, a crosslinked compound, a carbocyclic compound, and a heterocyclic compound). Represents the number of carbon atoms among the atoms to be used. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of carbons forming the ring. The "ring-forming carbon number" described below shall be the same unless otherwise stated. For example, the benzene ring has 6 ring-forming carbon atoms, the naphthalene ring has 10 ring-forming carbon atoms, the pyridine ring has 5 ring-forming carbon atoms, and the furan ring has 4 ring-forming carbon atoms. Further, for example, the ring-forming carbon number of the 9,9-diphenylfluorenyl group is 13, and the ring-forming carbon number of the 9,9'-spirobifluorenyl group is 25.
Further, when the benzene ring is substituted with, for example, an alkyl group as a substituent, the carbon number of the alkyl group is not included in the ring-forming carbon number of the benzene ring. Therefore, the ring-forming carbon number of the benzene ring substituted with the alkyl group is 6. Further, when the naphthalene ring is substituted with, for example, an alkyl group as a substituent, the carbon number of the alkyl group is not included in the ring-forming carbon number of the naphthalene ring. Therefore, the ring-forming carbon number of the naphthalene ring substituted with the alkyl group is 10.

In the present specification, the number of ring-forming atoms is a compound having a structure in which atoms are cyclically bonded (for example, a monocycle, a fused ring, and a ring assembly) (for example, a monocyclic compound, a condensed ring compound, a crosslinked compound, and a carbocycle). Represents the number of atoms constituting the ring itself of the compound and the heterocyclic compound). Atoms that do not form a ring (for example, a hydrogen atom that terminates the bond of atoms that form a ring) and atoms included in the substituent when the ring is substituted by a substituent are not included in the number of ring-forming atoms. The "number of ring-forming atoms" described below shall be the same unless otherwise stated. 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. For example, the number of hydrogen atoms bonded to the pyridine ring or the number of atoms constituting the substituent is not included in the number of pyridine ring forming atoms. Therefore, the number of ring-forming atoms of the pyridine ring to which the hydrogen atom or the substituent is bonded is 6. Further, for example, a hydrogen atom bonded to a carbon atom of a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms of the quinazoline ring. Therefore, the number of ring-forming atoms of the quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

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

In the present specification, "the number of atoms XX to YY" in the expression "the ZZ group having the number of atoms XX to YY substituted or unsubstituted" represents the number of atoms when the ZZ group is unsubstituted and is substituted. Does not include the number of atoms of the substituent in the case. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

In the present specification, the unsubstituted ZZ group represents the case where the "substituted or unsubstituted ZZ group" is the "unsubstituted ZZ group", and the substituted ZZ group is the "substituted or unsubstituted ZZ group". Represents the case where is a "substitute ZZ group".
As used herein, the term "unsubstituted" in the case of "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group is not replaced with the substituent. The hydrogen atom in the "unsubstituted ZZ group" is a light hydrogen atom, a heavy hydrogen atom, or a triple hydrogen atom.
Further, in the present specification, "substitution" in the case of "substituent or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced with the substituent. Similarly, "substitution" in the case of "BB group substituted with AA group" means that one or more hydrogen atoms in the BB group are replaced with the AA group.

"Substituents described herein"
Hereinafter, the substituents described in the present specification will be described.

The ring-forming carbon number of the "unsubstituted aryl group" described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise stated herein. ..
The number of ring-forming atoms of the "unsubstituted heterocyclic group" described herein is 5 to 50, preferably 5 to 30, more preferably 5 to 18, unless otherwise stated herein. be.
The carbon number of the "unsubstituted alkyl group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise stated herein.
The carbon number of the "unsubstituted alkenyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise stated herein.
The carbon number of the "unsubstituted alkynyl group" described herein is 2 to 50, preferably 2 to 20, and more preferably 2 to 6, unless otherwise stated herein.
The ring-forming carbon number of the "unsubstituted cycloalkyl group" described herein is 3 to 50, preferably 3 to 20, more preferably 3 to 6, unless otherwise stated herein. be.
The ring-forming carbon number of the "unsubstituted arylene group" described herein is 6 to 50, preferably 6 to 30, more preferably 6 to 18, unless otherwise stated herein. ..
Unless otherwise stated herein, the number of ring-forming atoms of the "unsubstituted divalent heterocyclic group" described herein is 5 to 50, preferably 5 to 30, and more preferably 5. ~ 18.
The carbon number of the "unsubstituted alkylene group" described herein is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise stated herein.

-"Substituted or unsubstituted aryl group"
Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in the present specification include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B). ) Etc. can be mentioned. (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". Refers to the case of "substituted aryl group".) In the present specification, the term "aryl group" includes both "unsubstituted aryl group" and "substituted aryl group".
The "substituted aryl group" means a group in which one or more hydrogen atoms of the "unsubstituted aryl group" are replaced with a substituent. Examples of the "substituted aryl group" include a group in which one or more hydrogen atoms of the "unsubstituted aryl group" of the following specific example group G1A are replaced with a substituent, and a substituted aryl group of the following specific example group G1B. Examples are given. The examples of the "unsubstituted aryl group" and the "substituted aryl group" listed here are merely examples, and the "substituted aryl group" described in the present specification is the following specific example. The group in which the hydrogen atom bonded to the carbon atom of the aryl group itself in the "substituted aryl group" of the group G1B is further replaced with the substituent, and the hydrogen atom of the substituent in the "substituted aryl group" of the following specific example group G1B Further, a group replaced with a substituent is also included.

• Unsubstituted aryl group (specific example group G1A):
Phenyl group,
p-biphenyl group,
m-biphenyl group,
o-biphenyl group,
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,
Anthril group,
Benzoanthril group,
Phenantril group,
Benzophenanthril group,
Fenarenyl group,
Pyrenyl group,
Chrysenyl group,
Benzocrisenyl group,
Triphenylenyl group,
Benzotriphenylenyl group,
Tetrasenyl group,
Pentacenyl group,
Fluolenyl group,
9,9'-spirobifluolenyl group,
Benzofluorenyl group,
Dibenzofluorenyl group,
Fluoranthenyl group,
Benzofluoranthenyl group,
A perylenyl group and a monovalent aryl group derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

-Substituted aryl group (specific example group G1B):
o-tolyl group,
m-tolyl group,
p-tolyl group,
Parakisilyl group,
Meta-kisilyl group,
Ortho-kisilyl 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-bis (4-methylphenyl) fluorenyl group,
9,9-bis (4-isopropylphenyl) fluorenyl group,
9,9-bis (4-t-butylphenyl) fluorenyl group,
Cyanophenyl group,
Triphenylsilylphenyl group,
Trimethylsilylphenyl group,
Phenylnaphthyl group,
A naphthylphenyl group and a group in which one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the general formulas (TEMP-1) to (TEMP-15) are replaced with a substituent.

-"Substituted or unsubstituted heterocyclic group"
The "heterocyclic group" described herein is a cyclic group containing at least one heteroatom in the ring-forming atom. Specific examples of the hetero atom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.
The "heterocyclic group" described herein is a monocyclic group or a fused ring group.
The "heterocyclic group" described herein is an aromatic heterocyclic group or a non-aromatic heterocyclic group.
Specific examples (specific example group G2) of the "substituted or unsubstituted heterocyclic group" described in the present specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2). Specific example group G2B) and the like can be mentioned. (Here, the unsubstituted heterocyclic group refers to the case where the "substituted or unsubstituted heterocyclic group" is the "unsubstituted heterocyclic group", and the substituted heterocyclic group is "substituted or unsubstituted". Refers to the case where the "heterocyclic group" is a "substituted heterocyclic group".) In the present specification, the term "heterocyclic group" is simply referred to as "unsubstituted heterocyclic group" and "substituted heterocyclic group". Including both.
The "substituted heterocyclic group" means a group in which one or more hydrogen atoms of the "unsubstituted heterocyclic group" are replaced with a substituent. Specific examples of the "substituted heterocyclic group" include a group in which the hydrogen atom of the "unsubstituted heterocyclic group" of the following specific example group G2A is replaced, an example of the substituted heterocyclic group of the following specific example group G2B, and the like. Can be mentioned. The examples of the "unsubstituted heterocyclic group" and the "substituted heterocyclic group" listed here are merely examples, and the "substituted heterocyclic group" described in the present specification is specifically referred to as a "substituted heterocyclic group". A group in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself in the "substituent heterocyclic group" of the example group G2B is further replaced with a substituent, and a substituent in the "substituent heterocyclic group" of the specific example group G2B. Also included are groups in which the hydrogen atom of is replaced with a substituent.

The specific example group G2A is, for example, an unsubstituted heterocyclic group containing the following nitrogen atom (specific example group G2A1), an unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2), and a non-substituted complex ring group containing a sulfur atom. (Specific example group G2A3) and a monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33). (Specific example group G2A4) is included.

The specific example group G2B is, for example, a substituted heterocyclic group containing the following nitrogen atom (specific example group G2B1), a substituted heterocyclic group containing an oxygen atom (specific example group G2B2), and a substituted heterocycle containing a sulfur atom. The substituent is one or more hydrogen atoms of the group (specific example group G2B3) and the monovalent heterocyclic group derived from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33). Includes replaced groups (specific example group G2B4).

An unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1):
Pyrrolyl group,
Imidazolyl group,
Pyrazolyl group,
Triazolyl group,
Tetrazoleyl group,
Oxazolyl group,
Isooxazolyl group,
Oxadiazolyl group,
Thiazolyl group,
Isothiazolyl group,
Thiasia Zoryl group,
Pyridyl group,
Pyridadinyl group,
Pyrimidinyl group,
Pyrazinel group,
Triazinyl group,
Indrill group,
Isoin drill group,
Indridinyl group,
Kinolidinyl group,
Quinoline group,
Isoquinolyl group,
Synnolyl group,
Phthalazinyl group,
Kinazolinyl group,
Kinoxalinyl group,
Benzoimidazolyl group,
Indazolyl group,
Phenantrolinyl group,
Phenantridinyl group,
Acridinyl group,
Phenazinyl group,
Carbazole group,
Benzocarbazolyl group,
Morphorino group,
Phenoxazinyl group,
Phenothiadinyl group,
Azacarbazolyl group and diazacarbazolyl group.

An unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2):
Frill group,
Oxazolyl group,
Isooxazolyl group,
Oxadiazolyl group,
Xanthenyl group,
Benzofuranyl group,
Isobenzofuranyl group,
Dibenzofuranyl group,
Naftbenzofuranyl group,
Benzoxazolyl group,
Benzoisoxazolyl group,
Phenoxazinyl group,
Morphorino group,
Ginaftfuranyl group,
Azadibenzofuranyl group,
Diazadibenzofuranyl group,
Azanaftbenzofuranyl group and diazanaphthobenzofuranyl group.

An unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3):
Thienyl group,
Thiazolyl group,
Isothiazolyl group,
Thiasia Zoryl group,
Benzothiophenyl group (benzothienyl group),
Isobenzothiophenyl group (isobenzothienyl group),
Dibenzothiophenyl group (dibenzothienyl group),
Naftbenzothiophenyl group (naphthobenzothienyl group),
Benzothiazolyl group,
Benzoisothiazolyl group,
Phenothiadinyl group,
Dinaftthiophenyl group (dinaftthienyl group),
Azadibenzothiophenyl group (azadibenzothienyl group),
Diazadibenzothiophenyl group (diazadibenzothienyl group),
Azanaft benzothiophenyl group (azanaft benzothienyl group) and diazanaphthobenzothiophenyl group (diazanaft benzothienyl group).

A monovalent heterocyclic group derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-16) to (TEMP-33) (specific example group G2A4):

In the general formulas (TEMP-16) to (TEMP _- 33), _XA and YA are independently oxygen atom, sulfur atom, NH, or CH ₂ . However, at least one of _XA and _YA is an oxygen atom, a sulfur atom, or NH.
In the general formulas (TEMP-16) to (TEMP _- 33), when at least one of X _A and YA is NH or CH ₂ , the general formulas (TEMP-16) to (TEMP-33) are used. The monovalent heterocyclic group derived from the represented ring structure includes a monovalent group obtained by removing one hydrogen atom from these NH or CH ₂ .

-Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1):
(9-Phenyl) carbazolyl group,
(9-biphenylyl) carbazolyl group,
(9-Phenyl) Phenylcarbazolyl group,
(9-naphthyl) carbazolyl group,
Diphenylcarbazole-9-yl group,
Phenylcarbazole-9-yl group,
Methylbenzoimidazolyl group,
Ethylbenzoimidazolyl group,
Phenyltriazinyl group,
Biphenyll triazinyl group,
Diphenyltriazinyl group,
Phenylquinazolinyl group and biphenylylquinazolinyl group.

-Substituted heterocyclic group containing an oxygen atom (specific example group G2B2):
Phenyldibenzofuranyl group,
Methyldibenzofuranyl group,
A monovalent residue of the t-butyldibenzofuranyl group and spiro [9H-xanthene-9,9'-[9H] fluorene].

-Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):
Phenyl dibenzothiophenyl group,
Methyl dibenzothiophenyl group,
A monovalent residue of t-butyldibenzothiophenyl group and spiro [9H-thioxanthene-9,9'-[9H] fluorene].

A group in which one or more hydrogen atoms of a monovalent heterocyclic group derived from the ring structure represented by the general formulas (TEMP-16) to (TEMP-33) are replaced with a substituent (specific example group G2B4). ):

The "one or more hydrogen atoms of the monovalent heterocyclic group" means that at least one of hydrogen atoms, XA and YA bonded to the ring-forming carbon atom of the monovalent heterocyclic group is NH. It means one or more hydrogen atoms selected from the hydrogen atom bonded to the nitrogen atom of the case and the hydrogen atom of the methylene group when one of XA and YA is CH2.

-"Substituted or unsubstituted alkyl group"
Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in the present specification include the following unsubstituted alkyl group (specific example group G3A) and substituted alkyl group (specific example group G3B). ). (Here, the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group", and the substituted alkyl group is a "substituted or unsubstituted alkyl group". Refers to the case of "substituted alkyl group".) Hereinafter, the term "alkyl group" includes both "unsubstituted alkyl group" and "substituted alkyl group".
The "substituted alkyl group" means a group in which one or more hydrogen atoms in the "unsubstituted alkyl group" are replaced with a substituent. Specific examples of the "substituted alkyl group" include a group in which one or more hydrogen atoms in the following "unsubstituted alkyl group" (specific example group G3A) are replaced with a substituent, and a substituted alkyl group (specific example). Examples of group G3B) can be mentioned. As used herein, the alkyl group in the "unsubstituted alkyl group" means a chain-like alkyl group. Therefore, the "unsubstituted alkyl group" includes a linear "unsubstituted alkyl group" and a branched "unsubstituted alkyl group". The examples of the "unsubstituted alkyl group" and the "substituted alkyl group" listed here are merely examples, and the "substituted alkyl group" described in the present specification includes the specific example group G3B. A group in which the hydrogen atom of the alkyl group itself in the "substituted alkyl group" of the above is further replaced with a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkyl group" of the specific example group G3B is further replaced with a substituent. included.

• Unsubstituted alkyl group (specific example group G3A):
Methyl group,
Ethyl group,
n-propyl group,
Isopropyl group,
n-butyl group,
Isobutyl group,
s-butyl group and t-butyl group.

Substituent alkyl group (specific example group G3B):
Propylfluoropropyl group (including isomers),
Pentafluoroethyl group,
2,2,2-trifluoroethyl group and trifluoromethyl group.

-"Substituted or unsubstituted alkenyl group"
Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described in the present specification include the following unsubstituted alkenyl group (specific example group G4A) and substituted alkenyl group (specific example group). G4B) and the like can be mentioned. (Here, the unsubstituted alkenyl group refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group", and the "substituted alkenyl group" is a "substituted or unsubstituted alkenyl group". Refers to the case where "is a substituted alkenyl group".) In the present specification, the term "alkenyl group" includes both "unsubstituted alkenyl group" and "substituted alkenyl group".
The "substituted alkenyl group" means a group in which one or more hydrogen atoms in the "unsubstituted alkenyl group" are replaced with a substituent. Specific examples of the "substituted alkenyl group" include a group in which the following "unsubstituted alkenyl group" (specific example group G4A) has a substituent, an example of a substituted alkenyl group (specific example group G4B), and the like. Be done. The examples of the "unsubstituted alkenyl group" and the "substituted alkenyl group" listed here are merely examples, and the "substituted alkenyl group" described in the present specification includes the specific example group G4B. A group in which the hydrogen atom of the alkenyl group itself in the "substituted alkenyl group" of the above is further replaced with a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkenyl group" of the specific example group G4B is further replaced with a substituent. included.

• Unsubstituted alkenyl group (specific example group G4A):
Vinyl group,
Allyl group,
1-butenyl group,
2-butenyl group and 3-butenyl group.

Substituent alkenyl group (specific example group G4B):
1,3-Butanjienyl group,
1-Methylvinyl group,
1-methylallyl group,
1,1-dimethylallyl group,
2-Methylallyl group and 1,2-dimethylallyl group.

-"Substituted or unsubstituted alkynyl 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 (specific example group G5A) and the like. (Here, the unsubstituted alkynyl group refers to the case where the "substituted or unsubstituted alkynyl group" is the "unsubstituted alkynyl group".) Hereinafter, the term "alkynyl group" is simply referred to as "unsubstituted alkynyl group". Includes both "alkynyl groups" and "substituted alkynyl groups".
The "substituted alkynyl group" means a group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" are replaced with a substituent. Specific examples of the "substituted alkynyl group" include a group in which one or more hydrogen atoms are replaced with a substituent in the following "unsubstituted alkynyl group" (specific example group G5A).

• Unsubstituted alkynyl group (specific example group G5A):
Ethynyl group

-"Substituted or unsubstituted cycloalkyl group"
Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group" described in the present specification include the following unsubstituted cycloalkyl group (specific example group G6A) and substituted cycloalkyl group (specific example group G6A). Specific example group G6B) and the like can be mentioned. (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 "substituted or unsubstituted". Refers to the case where the "cycloalkyl group" is a "substituted cycloalkyl group".) In the present specification, the term "cycloalkyl group" is simply referred to as "unsubstituted cycloalkyl group" and "substituted cycloalkyl group". Including both.
The "substituted cycloalkyl group" means a group in which one or more hydrogen atoms in the "unsubstituted cycloalkyl group" are replaced with a substituent. Specific examples of the "substituted cycloalkyl group" include a group in which one or more hydrogen atoms in the following "unsubstituted cycloalkyl group" (specific example group G6A) are replaced with a substituent, and a substituted cycloalkyl group. Examples of (Specific example group G6B) can be mentioned. The examples of the "unsubstituted cycloalkyl group" and the "substituted cycloalkyl group" listed here are merely examples, and the "substituted cycloalkyl group" described in the present specification is specifically referred to as "substituted cycloalkyl group". In the "substituted cycloalkyl group" of the example group G6B, a group in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself are replaced with the substituent, and in the "substituted cycloalkyl group" of the specific example group G6B. A group in which the hydrogen atom of the substituent is further replaced with the substituent is also included.

• Unsubstituted cycloalkyl group (specific example group G6A):
Cyclopropyl group,
Cyclobutyl group,
Cyclopentyl group,
Cyclohexyl group,
1-adamantyl group,
2-adamantyl group,
1-norbornyl group and 2-norbornyl group.

Substituent cycloalkyl group (specific example group G6B):
4-Methylcyclohexyl group.

-"A group represented by -Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ )"
As a specific example (specific example group G7) of the group represented by —Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ) described in the present specification,
-Si (G1) (G1) (G1),
-Si (G1) (G2) (G2),
-Si (G1) (G1) (G2),
-Si (G2) (G2) (G2),
-Si (G3) (G3) (G3), and -Si (G6) (G6) (G6)
Can be mentioned. here,
G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1.
G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.
G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3.
G6 is the "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.
-A plurality of G1s in Si (G1) (G1) (G1) are the same as or different from each other.
-A plurality of G2s in Si (G1) (G2) (G2) are the same as or different from each other.
-A plurality of G1s in Si (G1) (G1) (G2) are the same as or different from each other.
-A plurality of G2s in Si (G2) (G2) (G2) are the same as or different from each other.
-A plurality of G3s in Si (G3) (G3) (G3) are the same as or different from each other.
-A plurality of G6s in Si (G6) (G6) (G6) are the same as or different from each other.

-"A group represented by -O- (R ₉₀₄ )"
As a specific example (specific example group G8) of the group represented by —O— (R ₉₀₄ ) described in the present specification,
-O (G1),
-O (G2),
-O (G3) and -O (G6)
Can be mentioned.
here,
G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1.
G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.
G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3.
G6 is the "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.

-"A group represented by -S- (R ₉₀₅ )"
As a specific example (specific example group G9) of the group represented by —S— (R ₉₀₅ ) described in the present specification,
-S (G1),
-S (G2),
-S (G3) and -S (G6)
Can be mentioned.
here,
G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1.
G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.
G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3.
G6 is the "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.

-"A group represented by -N (R ₉₀₆ ) (R ₉₀₇ )"
As a specific example (specific example group G10) of the group represented by −N (R ₉₀₆ ) (R ₉₀₇ ) described in the present specification,
-N (G1) (G1),
-N (G2) (G2),
-N (G1) (G2),
-N (G3) (G3) and -N (G6) (G6)
Can be mentioned.
here,
G1 is the "substituted or unsubstituted aryl group" described in the specific example group G1.
G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.
G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3.
G6 is the "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.
-The plurality of G1s in N (G1) (G1) are the same as or different from each other.
-The plurality of G2s in N (G2) (G2) are the same as or different from each other.
-The plurality of G3s in N (G3) (G3) are the same as or different from each other.
A plurality of G6s in -N (G6) (G6) are the same as or different from each other.

・ "Halogen atom"
Specific examples of the “halogen atom” described in the present specification (specific example group G11) include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom and the like.

-"Substituted or unsubstituted fluoroalkyl group"
In the "substituted or unsubstituted fluoroalkyl group" described herein, at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a fluorine atom. It also includes a group (perfluoro group) in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with fluorine atoms. The "unsubstituted fluoroalkyl group" has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms, unless otherwise specified herein. The "substituted fluoroalkyl group" means a group in which one or more hydrogen atoms of the "fluoroalkyl group" are replaced with a substituent. The "substituted fluoroalkyl group" described in the present specification includes a group in which one or more hydrogen atoms bonded to a carbon atom of an alkyl chain in the "substituted fluoroalkyl group" are further replaced with a substituent, and a group. Also included is a group in which one or more hydrogen atoms of the substituent in the "substituted fluoroalkyl group" are further replaced with the substituent. Specific examples of the "unsubstituted fluoroalkyl group" include an example of a group in which one or more hydrogen atoms in the "alkyl group" (specific example group G3) are replaced with a fluorine atom.

-"Substituted or unsubstituted haloalkyl group"
In the "substituted or unsubstituted haloalkyl group" described herein, at least one hydrogen atom bonded to a carbon atom constituting the alkyl group in the "substituted or unsubstituted alkyl group" is replaced with a halogen atom. It means a group and includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The "unsubstituted haloalkyl group" has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms, unless otherwise specified herein. The "substituted haloalkyl group" means a group in which one or more hydrogen atoms of the "haloalkyl group" are replaced with a substituent. The "substituted haloalkyl group" described in the present specification includes a group in which one or more hydrogen atoms bonded to a carbon atom of the alkyl chain in the "substituted haloalkyl group" are further replaced with a substituent, and a "substitution". Also included are groups in which one or more hydrogen atoms of the substituents in the "haloalkyl group" are further replaced by the substituents. Specific examples of the "unsubstituted haloalkyl group" include an example of a group in which one or more hydrogen atoms in the "alkyl group" (specific example group G3) are replaced with a halogen atom. The haloalkyl group may be referred to as a halogenated alkyl group.

-"Substituted or unsubstituted alkoxy group"
A specific example of the "substituted or unsubstituted alkoxy group" described in the present specification is a group represented by —O (G3), where G3 is the “substituted or substituted” described in the specific example group G3. It is an unsubstituted alkyl group. " The "unsubstituted alkoxy group" has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms, unless otherwise specified herein.

-"Substituted or unsubstituted alkylthio group"
A specific example of the "substituted or unsubstituted alkylthio group" described in the present specification is a group represented by —S (G3), where G3 is the “substituted or substituted” described in the specific example group G3. It is an unsubstituted alkyl group. " The "unsubstituted alkylthio group" has 1 to 50 carbon atoms, preferably 1 to 30 carbon atoms, and more preferably 1 to 18 carbon atoms, unless otherwise specified herein.

-"Substituted or unsubstituted aryloxy group"
A specific example of the "substituted or unsubstituted aryloxy group" described in the present specification is a group represented by —O (G1), where G1 is the “substitution” described in the specific example group G1. Alternatively, it is an unsubstituted aryl group. " The ring-forming carbon number of the "unsubstituted aryloxy group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise specified herein.

-"Substituted or unsubstituted arylthio group"
A specific example of the "substituted or unsubstituted arylthio group" described in the present specification is a group represented by —S (G1), where G1 is the “substituted or substituted” described in the specific example group G1. It is an unsubstituted aryl group. " The ring-forming carbon number of the "unsubstituted arylthio group" is 6 to 50, preferably 6 to 30, and more preferably 6 to 18, unless otherwise stated herein.

-"Substituted or unsubstituted trialkylsilyl group"
A specific example of the "trialkylsilyl group" described in the present specification is a group represented by −Si (G3) (G3) (G3), where G3 is described in the specific example group G3. It is a "substituted or unsubstituted alkyl group". -A plurality of G3s in Si (G3) (G3) (G3) are the same as or different from each other. The carbon number of each alkyl group of the "trialkylsilyl group" is 1 to 50, preferably 1 to 20, and more preferably 1 to 6, unless otherwise specified herein.

-"Substituted or unsubstituted aralkyl group"
A specific example of the "substituted or unsubstituted arylyl group" described in the present specification is a group represented by-(G3)-(G1), where G3 is described in the specific example group G3. It is a "substituted or unsubstituted alkyl group", and G1 is a "substituted or unsubstituted aryl group" described in the specific example group G1. Therefore, the "aralkyl group" is a group in which the hydrogen atom of the "alkyl group" is replaced with the "aryl group" as a substituent, and is an embodiment of the "substituted alkyl group". The "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group", and the carbon number of the "unsubstituted aralkyl group" is unless otherwise specified herein. , 7 to 50, preferably 7 to 30, and more preferably 7 to 18.
Specific examples of the "substituted or unsubstituted aralkyl group" include a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylisopropyl group, a 2-phenylisopropyl group, a phenyl-t-butyl group and an α. -Naphtylmethyl 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.

The substituted or unsubstituted aryl groups described herein are preferably phenyl groups, p-biphenyl groups, m-biphenyl groups, o-biphenyl groups, p-terphenyl-unless otherwise described herein. 4-Il group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl- 2-Il 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 , Pyrenyl group, chrysenyl group, triphenylenyl group, fluorenyl group, 9,9'-spirobifluorenyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group and the like.

The substituted or unsubstituted heterocyclic group described herein is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzoimidazolyl group, or a phenyl group, unless otherwise specified herein. Nantrolinyl group, carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 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) Carbazole-1-yl Group, (9-Phenyl) Carbazole-2-yl Group, (9-Phenyl) Carbazole-3-yl Group, or (9-Phenyl) Carbazole Group -4-yl group), (9-biphenylyl) carbazolyl group, (9-phenyl) phenylcarbazolyl group, diphenylcarbazole-9-yl group, phenylcarbazole-9-yl group, phenyltriazinyl group, biphenylylt A lyazynyl group, a diphenyltriazinyl group, a phenyldibenzofuranyl group, a phenyldibenzothiophenyl group and the like.

As used herein, the carbazolyl group is specifically any of the following groups, unless otherwise stated herein.

As used herein, the (9-phenyl) carbazolyl group is specifically any of the following groups, unless otherwise stated herein.

In the general formulas (TEMP-Cz1) to (TEMP-Cz9), * represents a binding site.

As used herein, the dibenzofuranyl group and the dibenzothiophenyl group are specifically any of the following groups, unless otherwise stated herein.

In the general formulas (TEMP-34) to (TEMP-41), * represents a binding site.

Substituentally substituted or unsubstituted alkyl groups described herein are preferably methyl groups, ethyl groups, propyl groups, isopropyl groups, n-butyl groups, isobutyl groups, and t-, unless otherwise stated herein. It is a butyl group or the like.

-"Substituted or unsubstituted arylene group"
Unless otherwise stated, the "substituted or unsubstituted arylene group" described herein is derived by removing one hydrogen atom on the aryl ring from the above "substituted or unsubstituted aryl group" 2 It is the basis of the price. As a specific example of the "substituted or unsubstituted arylene group" (specific example group G12), one hydrogen atom on the aryl ring is removed from the "substituted or unsubstituted aryl group" described in the specific example group G1. Examples include the induced divalent group.

-"Substituted or unsubstituted divalent heterocyclic group"
Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described in the present specification shall exclude one hydrogen atom on the heterocycle from the above "substituted or unsubstituted heterocyclic group". It is a divalent group derived by. As a specific example (specific example group G13) of the "substituted or unsubstituted divalent heterocyclic group", one hydrogen on the heterocycle from the "substituted or unsubstituted heterocyclic group" described in the specific example group G2. Examples thereof include a divalent group derived by removing an atom.

-"Substituted or unsubstituted alkylene group"
Unless otherwise stated, the "substituted or unsubstituted alkylene group" described herein is derived by removing one hydrogen atom on the alkyl chain from the above "substituted or unsubstituted alkyl group" 2 It is the basis of the price. As a specific example of the "substituted or unsubstituted alkylene group" (specific example group G14), one hydrogen atom on the alkyl chain is removed from the "substituted or unsubstituted alkyl group" described in the specific example group G3. Examples include the induced divalent group.

The substituted or unsubstituted arylene group described in the present specification is preferably any group of the following general formulas (TEMP-42) to (TEMP-68), unless otherwise described in the present specification.

In the general formulas (TEMP-42) to (TEMP-52), _Q1 to _Q10 are independently hydrogen atoms or substituents, respectively.
In the general formulas (TEMP-42) to (TEMP-52), * represents a binding site.

In the general formulas (TEMP-53) to (TEMP-62), _Q1 to _Q10 are independently hydrogen atoms or substituents, respectively.
The formulas Q ₉ and Q ₁₀ may be bonded to each other via a single bond to form a ring.
In the general formulas (TEMP-53) to (TEMP-62), * represents a binding site.

In the general formulas (TEMP-63) to (TEMP _- 68), _Q1 to Q8 are independently hydrogen atoms or substituents, respectively.
In the general formulas (TEMP-63) to (TEMP-68), * represents a binding site.

The substituted or unsubstituted divalent heterocyclic group described in the present specification is preferably a group according to any one of the following general formulas (TEMP-69) to (TEMP-102), unless otherwise described in the present specification. Is.

In the general formulas (TEMP-69) to (TEMP-82), _Q1 to _Q9 are independently hydrogen atoms or substituents, respectively.

In the general formulas (TEMP-83) to (TEMP _- 102), _Q1 to Q8 are independently hydrogen atoms or substituents, respectively.

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

・ "When combining to form a ring"
In the present specification, "one or more sets of two or more adjacent pairs are bonded to each other to form a substituted or unsubstituted single ring, or are bonded to each other to form a substituted or unsubstituted fused ring. "Forming or not binding to each other" means "one or more pairs of two or more adjacent pairs combine with each other to form a substituted or unsubstituted monocycle" and "adjacent". One or more pairs of two or more pairs are bonded to each other to form a substituted or unsubstituted fused ring, and one or more pairs of two or more adjacent pairs are not bonded to each other. "When and means.
In the present specification, "one or more sets of two or more adjacent sets are combined with each other to form a substituted or unsubstituted monocycle", and "one of two or more adjacent sets". Regarding the case where a pair or more are bonded to each other to form a substituted or unsubstituted fused ring (hereinafter, these cases may be collectively referred to as "a case where they are bonded to form a ring"), the following. ,explain. The case of an anthracene compound represented by the following general formula (TEMP-103) in which the mother skeleton is an anthracene ring will be described as an example.

For example, in the case of "one or more sets of two or more adjacent sets of R ₉₂₁ to R ₉₃₀ are combined with each other to form a ring", the set of two adjacent sets is one set. Is a pair of R ₉₂₁ and R ₉₂₂ , a pair of R ₉₂₂ and R ₉₂₃ , a pair of R ₉₂₃ and R ₉₂₄ , a pair of R ₉₂₄ and R ₉₃₀ , a pair of R ₉₃₀ and R ₉₂₅ , and R ₉₂₅ . The pair with R ₉₂₆ , the pair with R ₉₂₆ and R ₉₂₇ , the pair with R ₉₂₇ and R ₉₂₈ , the pair with R ₉₂₈ and R ₉₂₉ , and the pair with R ₉₂₉ and R ₉₂₁ .

The above-mentioned "one or more sets" means that two or more sets of two or more adjacent sets may form a ring at the same time. For example, when R ₉₂₁ and R ₉₂₂ are coupled to each other to form ring Q _A , and at the same time R ₉₂₅ and R ₉₂₆ are coupled to each other to form ring Q _B , the above general formula (TEMP-103) is used. The anthracene compound represented is represented by the following general formula (TEMP-104).

The case where "a set consisting of two or more adjacent" forms a ring is not only the case where the pair consisting of adjacent "two" is combined as in the above example, but also from the adjacent "three or more". Including the case where the pairs are combined. For example, R ₉₂₁ and R ₉₂₂ are coupled to each other to form a ring Q _A , and _{R 922} and R ₉₂₃ are coupled to each other to form a ring QC, and three adjacent to each other (R ₉₂₁ , R). It means a case where a pair consisting of ₉₂₂ and _R923 ) is bonded to each other to form a ring and condensed into an anthracene mother skeleton. In this case, the anthracene compound represented by the general formula (TEMP-103) is described below. It is represented by the general formula (TEMP-105). In the following general formula (TEMP-105), ring Q _A and ring Q _C share R ₉₂₂ .

The formed "monocycle" or "condensed ring" may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even when "a set of two adjacent sets" forms a "monocycle" or a "condensed ring", the "monocycle" or "condensed ring" is a saturated ring or a ring of saturation. An unsaturated ring can be formed. For example, the ring _QA and the ring QB formed in the general formula (TEMP _- 104) are "single ring" or "condensed ring", respectively. Further, the ring Q _A and the ring Q _C formed in the general formula (TEMP-105) are "condensed rings". The ring Q _A and the ring Q _C of the general formula (TEMP-105) are formed into a fused ring by condensing the ring Q _A and the ring Q _C. If the ring QA of the general formula ( _{TMEP -} 104) is a benzene ring, the ring QA is a monocyclic ring. If the ring QA of the general formula ( _{TMEP -} 104) is a naphthalene ring, the ring QA is a fused ring.

The "unsaturated ring" includes an aromatic hydrocarbon ring, an aromatic heterocycle, and an aliphatic hydrocarbon ring having an unsaturated bond, that is, a double bond and / or a triple bond in the ring structure (for example, an unsaturated ring). Cyclohexene, cyclohexadiene, etc.), and non-aromatic heterocycles with unsaturated bonds (eg, dihydropyran, imidazoline, pyrazoline, quinolidine, indolin, isoindrin, etc.). The "saturated ring" includes an aliphatic hydrocarbon ring having no unsaturated bond or a non-aromatic heterocycle having no unsaturated bond.
Specific examples of the aromatic hydrocarbon ring include a structure in which the group given as a specific example in the specific example group G1 is terminated by a hydrogen atom.
Specific examples of the aromatic heterocycle include a structure in which the aromatic heterocyclic group given as a specific example in the specific example group G2 is terminated by a hydrogen atom.
Specific examples of the aliphatic hydrocarbon ring include a structure in which the group given as a specific example in the specific example group G6 is terminated by a hydrogen atom.
By "forming a ring" is meant forming a ring with only a plurality of atoms in the mother skeleton, or with a plurality of atoms in the mother skeleton and one or more arbitrary atoms. For example, the ring QA formed by bonding R ₉₂₁ and _{R 922} to each other, which is represented by the general formula (TEMP-104), has a carbon atom of an anthracene skeleton to which R ₉₂₁ is bonded and an anthracene to which R ₉₂₂ is bonded. It means a ring formed by carbon atoms in the skeleton and one or more arbitrary atoms. As a specific example, in the case of forming a ring QA with _{R 921} and R ₉₂₂ , a carbon atom of an anthracene skeleton to which R ₉₂₁ is bonded, a carbon atom of an anthracene skeleton to which R ₉₂₂ is bonded, and four carbon atoms. When forming a monocyclic unsaturated ring with, the ring formed by R ₉₂₁ and R ₉₂₂ is a benzene ring.

Here, "arbitrary atom" is preferably at least one atom selected from the group consisting of a carbon atom, a nitrogen atom, an oxygen atom, and a sulfur atom, unless otherwise specified in the present specification. At any atom (for example, in the case of a carbon atom or a nitrogen atom), the bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described later. If it contains any atom other than a carbon atom, the ring formed is a heterocycle.
Unless otherwise described herein, the number of "one or more arbitrary atoms" constituting the monocyclic or condensed ring is preferably 2 or more and 15 or less, and more preferably 3 or more and 12 or less. , More preferably 3 or more and 5 or less.
Unless otherwise described herein, the "monocycle" and the "condensed ring" are preferably "monocycles".
Unless otherwise described herein, the "saturated ring" and the "unsaturated ring" are preferably "unsaturated rings".
Unless otherwise stated herein, a "monocycle" is preferably a benzene ring.
Unless otherwise stated herein, the "unsaturated ring" is preferably a benzene ring.
When "one or more pairs of two or more adjacent pairs""bond to each other to form a substituted or unsubstituted monocycle", or "bond to each other to form a substituted or unsubstituted fused ring". In the case of "forming", unless otherwise described herein, preferably one or more pairs of two or more adjacent pairs are bonded to each other with a plurality of atoms in the matrix and one or more 15 pairs. It forms a substituted or unsubstituted "unsaturated ring" consisting of at least one atom selected from the group consisting of the following carbon atom, nitrogen atom, oxygen atom, and sulfur atom.

When the above-mentioned "monocycle" or "condensed ring" has a substituent, the substituent is, for example, an "arbitrary substituent" described later. Specific examples of the substituent when the above-mentioned "monocycle" or "condensed ring" has a substituent are the substituents described in the above-mentioned "Substituents described in the present specification" section.
When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, an "arbitrary substituent" described later. Specific examples of the substituent when the above-mentioned "monocycle" or "condensed ring" has a substituent are the substituents described in the above-mentioned "Substituents described in the present specification" section.
The above is the case where "one or more sets of two or more adjacent sets are combined with each other to form a substituted or unsubstituted monocycle" and "one or more sets of two or more adjacent sets". However, it is a description of the case of "bonding to each other to form a substituted or unsubstituted fused ring"("the case of bonding to form a ring").

Substituent in the case of "substitutable or unsubstituted" In one embodiment of the present specification, the substituent in the case of "substitutable or unsubstituted" (referred to as "arbitrary substituent" in the present specification). May be.), For example.
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,
-Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
-O- (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
It is a group selected from the group consisting of an aryl group having an unsubstituted ring-forming carbon number of 6 to 50 and a heterocyclic group having an unsubstituted ring-forming atom number of 5 to 50.
Here, R ₉₀₁ to R ₉₀₇ are independent of each other.
Hydrogen atom,
Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms,
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.
If there are two or more R _901s , the two or more R _901s are the same or different from each other.
When two or more R _902s are present, the two or more R _902s are the same as or different from each other.
When two or more R _903s are present, the two or more R _903s are the same as or different from each other.
If there are two or more R _904s , the two or more R _904s are the same or different from each other.
If there are two or more R _905s , the two or more R _905s are the same or different from each other.
If there are two or more R- _906s , the two or more R- _906s are the same or different from each other.
When two or more R _907s are present, the two or more R _907s are the same as or different from each other.

In one embodiment, the substituent in the case of "substitutable or unsubstituted" is
Alkyl group with 1 to 50 carbon atoms,
It is a group selected from the group consisting of an aryl group having 6 to 50 ring-forming carbon atoms and a heterocyclic group having 5 to 50 ring-forming atoms.

In one embodiment, the substituent in the case of "substitutable or unsubstituted" is
Alkyl groups with 1 to 18 carbon atoms,
It is a group selected from the group consisting of an aryl group having 6 to 18 ring-forming carbon atoms and a heterocyclic group having 5 to 18 ring-forming atoms.

Specific examples of each of the above-mentioned arbitrary substituents are specific examples of the substituents described in the above-mentioned "Substituents described in the present specification" section.

Unless otherwise stated herein, any adjacent substituents may form a "saturated ring" or an "unsaturated ring", preferably substituted or unsaturated 5 It forms a membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring. do.
Unless otherwise stated herein, any substituent may further have a substituent. The substituent further possessed by the arbitrary substituent is the same as that of the above-mentioned arbitrary substituent.

In the present specification, the numerical range expressed by using "AA to BB" has the numerical value AA described before "AA to BB" as the lower limit value and the numerical value BB described after "AA to BB". Means the range including as the upper limit value.

（式（１）において、
Ｒ_１～Ｒ_１０は、水素原子である。
Ｌ_１～Ｌ_４は、それぞれ独立に、
単結合、
置換もしくは無置換の環形成炭素数６～５０のアリーレン基、又は
置換もしくは無置換の環形成原子数５～５０の２価の複素環基である。
Ｌ_１及びＬ_２は、互いに単結合で結合するか、あるいは互いに単結合で結合しない。
Ｌ_３及びＬ_４は、互いに単結合で結合するか、あるいは互いに単結合で結合しない。
Ａｒ_１～Ａｒ_４は、それぞれ独立に、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
Ｌ_１及びＬ_２が単結合である場合、Ａｒ_１及びＡｒ_２は、互いに単結合で結合するか、あるいは互いに単結合で結合しない。
Ｌ_３及びＬ_４が単結合である場合、Ａｒ_３及びＡｒ_４は、互いに単結合で結合するか、あるいは互いに単結合で結合しない。
「置換もしくは無置換の」という場合における置換基は、
無置換の炭素数１～５０のアルキル基、
無置換の炭素数２～５０のアルケニル基、
無置換の炭素数２～５０のアルキニル基、
無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ_９０１）（Ｒ_９０２）（Ｒ_９０３）、
－Ｏ－（Ｒ_９０４）、
－Ｓ－（Ｒ_９０５）、
－Ｎ（Ｒ_９０６）（Ｒ_９０７）
（ここで、Ｒ_９０１～Ｒ_９０７は、それぞれ独立に、
水素原子、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。Ｒ_９０１～Ｒ_９０７が２個以上存在する場合、２個以上のＲ_９０１～Ｒ_９０７のそれぞれは同一でもよく、異なっていてもよい。）、
ハロゲン原子、シアノ基、ニトロ基、
無置換の環形成炭素数６～５０のアリール基、及び
無置換の環形成原子数５～５０の１価の複素環基
からなる群から選択される。
Ｒ_１～Ｒ_１０、Ｌ_１～Ｌ_４が有する水素原子、Ａｒ_１～Ａｒ_４が有する水素原子、Ｌ_１～Ｌ_４が置換されている場合の置換基が有する水素原子、及びＡｒ_１～Ａｒ_４が置換されている場合の置換基が有する水素原子のうち１つ以上は、重水素原子である。） [New compound]
The compound according to one aspect of the present invention is represented by the following formula (1).

(In equation (1)
R ₁ to R ₁₀ are hydrogen atoms.
L ₁ to L ₄ are independent of each other.
Single bond,
It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
L ₁ and L ₂ are either single-bonded to each other or not single-bonded to each other.
L ₃ and L ₄ are either single-bonded to each other or not single-bonded to each other.
Ar ₁ to Ar ₄ are independent of each other.
It is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a monovalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
When L ₁ and L ₂ are single bonds, Ar ₁ and Ar ₂ either bind to each other in a single bond or do not bind to each other in a single bond.
When L ₃ and L ₄ are single bonds, Ar ₃ and Ar ₄ either bind to each other in a single bond or do not bind to each other in a single bond.
The substituent in the case of "substituent or unsubstituted" is
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,
-Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
-O- (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ )
(Here, R ₉₀₁ to R ₉₀₇ are independent of each other.
Hydrogen atom,
Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms,
It is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a monovalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms. When two or more R ₉₀₁ to R ₉₀₇ are present, 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 selected from the group consisting of an aryl group having an unsubstituted ring-forming carbon number of 6 to 50 and a monovalent heterocyclic group having an unsubstituted ring-forming atom number of 5 to 50.
Hydrogen atoms of R ₁ to R ₁₀ , L ₁ to L ₄ , hydrogen atoms of Ar ₁ to Ar ₄ , hydrogen atoms of substituents when L ₁ to L ₄ are substituted, and Ar ₁ to Ar. One or more of the hydrogen atoms of the substituent when ₄ is substituted is a deuterium atom. )

By using the compound according to one aspect of the present invention, a long-life organic EL device can be manufactured.

The inclusion of deuterium atoms in the compound is confirmed by mass spectrometry or ¹ H-NMR analysis. In addition, the bond position of the deuterium atom in the compound is specified by ¹ H-NMR analysis method. Specifically, it is as follows.
Mass analysis is performed on the target compound, and it can be confirmed that one heavy hydrogen atom is contained because the molecular weight is increased by 1 as compared with the corresponding compound in which all hydrogen atoms are light hydrogen atoms. In addition, since deuterium atoms do not give a signal in ¹ H-NMR analysis, the number of deuterium atoms contained in the molecule is determined by the integrated value obtained by performing ¹ H-NMR analysis on the target compound. You can check. In addition, the bond position of the deuterium atom can be specified by performing ¹ H-NMR analysis on the target compound and assigning the signal.

_In one embodiment, a hydrogen atom of L1 to L4, a hydrogen atom of _Ar1 to _Ar4 , _a hydrogen atom of _a substituent when L1 to _L4 are substituted, and _Ar1 to _Ar4 One or more of the hydrogen atoms contained in the substituent when is substituted is a deuterium atom.

_{In one} embodiment, _one or more of the hydrogen atoms of L1 to L4 and the hydrogen atoms of the substituents when L1 to _L4 are substituted are deuterium atoms.

In one embodiment, one or more of R ₁ to R ₁₀ are deuterium atoms.

In one embodiment, one or more of R ₁ to R ₁₀ are deuterium atoms.
The hydrogen atom of L ₁ to L ₄ , the hydrogen atom of Ar ₁ to Ar ₄ , the hydrogen atom of the substituent when L ₁ to L ₄ is substituted, and the hydrogen atom of Ar ₁ to Ar ₄ are substituted. One or more of the hydrogen atoms of the substituents in the case are heavy hydrogen atoms.

（式（１－１）において、Ｒ_１～Ｒ_１０及びＡｒ_１～Ａｒ_４は、前記式（１）で定義したとおりである。
Ｒ_１～Ｒ_１０、Ａｒ_１～Ａｒ_４が有する水素原子、及びＡｒ_１～Ａｒ_４が置換されている場合の置換基が有する水素原子のうち１つ以上は、重水素原子である。） In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (1-1).

(In the formula (1-1), R ₁ to R ₁₀ and Ar ₁ to Ar ₄ are as defined in the above formula (1).
One or more of the hydrogen atoms contained in R ₁ to R ₁₀ , Ar ₁ to Ar ₄ , and the hydrogen atoms contained in the substituents when Ar ₁ to Ar ₄ are substituted are deuterium atoms. )

In one embodiment, among the hydrogen atoms of Ar ₁ to Ar ₄ of the compound represented by the above formula (1-1) and the hydrogen atoms of the substituent when Ar ₁ to Ar ₄ are substituted. One or more are heavy hydrogen atoms. From the viewpoint of producing an organic EL device having a longer life, it is preferable that one or more of the hydrogen atoms contained in Ar ₁ to Ar ₄ are deuterium atoms.

In one embodiment, one or more of R ₁ to R ₁₀ of the compound represented by the above formula (1-1) is a deuterium atom.

In one embodiment, one or more of R ₁ to R ₁₀ of the compound represented by the above formula (1-1) is a deuterium atom.
One or more of the hydrogen atoms contained in Ar ₁ to Ar ₄ and the hydrogen atoms contained in the substituents when Ar ₁ to Ar ₄ are substituted are deuterium atoms.

（式（１－２）において、Ｒ_１～Ｒ_１０は、前記式（１）で定義したとおりである。
Ｒ_２１～Ｒ_４０のうちの隣接する２以上の１組以上は互いに結合して置換もしくは無置換の飽和又は不飽和の環を形成するか、あるいは置換もしくは無置換の飽和又は不飽和の環を形成しない。
前記置換もしくは無置換の飽和又は不飽和の環を形成しないＲ_２１～Ｒ_４０は、それぞれ独立に、水素原子、又は置換基Ｒである。
置換基Ｒは、
置換もしくは無置換の炭素数１～５０のアルキル基、
置換もしくは無置換の炭素数２～５０のアルケニル基、
置換もしくは無置換の炭素数２～５０のアルキニル基、
置換もしくは無置換の環形成炭素数３～５０のシクロアルキル基、
－Ｓｉ（Ｒ_９０１）（Ｒ_９０２）（Ｒ_９０３）、
－Ｏ－（Ｒ_９０４）、
－Ｓ－（Ｒ_９０５）、
－Ｎ（Ｒ_９０６）（Ｒ_９０７）、
ハロゲン原子、シアノ基、ニトロ基、
置換もしくは無置換の環形成炭素数６～５０のアリール基、又は
置換もしくは無置換の環形成原子数５～５０の１価の複素環基である。
前記置換基Ｒが２個以上存在する場合、２個以上の前記置換基Ｒは同一でもよく、異なっていてもよい。
Ｒ_９０１～Ｒ_９０７は、前記式（１）で定義したとおりである。
Ｒ_１～Ｒ_１０、水素原子であるＲ_２１～Ｒ_４０、及び置換基ＲであるＲ_２１～Ｒ_４０が有する水素原子のうち１つ以上は、重水素原子である。） In one embodiment, the compound represented by the formula (1) is a compound represented by the following formula (1-2).

(In the formula (1-2), R ₁ to R ₁₀ are as defined in the above formula (1).
Two or more adjacent pairs of R ₂₁ to R ₄₀ combine with 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 substituted or unsubstituted Saturated or unsaturated rings R ₂₁ to R ₄₀ are independently hydrogen atoms or substituents R, respectively.
Substituent R is
Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
Substituted or unsubstituted cycloalkyl group having 3 to 50 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,
It is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a monovalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
When two or more of the substituents R are present, the two or more of the substituents R may be the same or different.
_R901 to _R907 are as defined by the above equation (1).
One or more of the hydrogen atoms contained in R ₁ to R ₁₀ , hydrogen atoms R ₂₁ to R ₄₀ , and substituents R R ₂₁ to R ₄₀ are deuterium atoms. )

"One or more pairs of two or more adjacent pairs of R ₂₁ to R ₄₀ combine with each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or unsaturated ring. Does not form. "
"One set of two or more adjacent to each other from R ₂₁ to R ₄₀ " is, for example, R ₂₁ and R ₂₂ , R ₂₂ and R ₂₃ , R ₂₃ and R ₂₄ , R ₂₄ and R ₂₅ , R ₂₅ and R ₂₆ . , R ₂₁ and R ₂₂ and R ₂₃ and the like.

In one embodiment, one or _more of the hydrogen atoms of the hydrogen atom R ₂₁ to R ₄₀ and the substituent R of the compound represented by the formula ₍ 1-2) are one or more. , A deuterium atom.

In one embodiment, one or more of R ₁ to R ₁₀ of the compound represented by the above formula (1-2) is a deuterium atom.

In one embodiment, one or more of R ₁ to R ₁₀ of the compound represented by the above formula (1-2) is a deuterium atom.
One or more of the hydrogen atoms contained in the hydrogen atoms R ₂₁ to R ₄₀ and the substituents R R ₂₁ to R ₄₀ are deuterium atoms.

In one embodiment, the substituent in the case of "substituted or unsubstituted" in the compound represented by the formula (1) is an alkyl group having 1 to 50 carbon atoms, an aryl group having 6 to 50 ring-forming carbon atoms, and the like. And a monovalent heterocyclic group having 5 to 50 ring-forming atoms.

In one embodiment, the substituent in the case of "substituted or unsubstituted" in the compound represented by the formula (1) is an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 ring-forming carbon atoms, and the like. It is selected from the group consisting of monovalent heterocyclic groups having 5 to 30 ring-forming atoms.

In one embodiment, the substituent in the case of "substituted or unsubstituted" in the compound represented by the formula (1) is an alkyl group having 1 to 18 carbon atoms, an aryl group having 6 to 18 ring-forming carbon atoms, and the like. It is selected from the group consisting of monovalent heterocyclic groups having 5 to 18 ring-forming atoms.

Specific examples of each substituent of the compound represented by the formula (1), the substituent and the halogen atom in the case of "substituent or unsubstituted" are the same as those described above.

The compound represented by the formula (1) can be synthesized by using a known alternative reaction or raw material suitable for the desired product, following the examples.

Specific examples of the compound represented by the formula (1) will be described below, but these are merely examples, and the compound represented by the formula (1) is not limited to the following specific examples. In the specific examples below, D represents a deuterium atom.

[Material for organic EL elements]
The compound according to one aspect of the present invention is useful as a material for an organic EL device, is useful as a material for a light emitting layer of an organic EL device, and is particularly useful as a dopant material for a light emitting layer.
By using the compound according to one aspect of the present invention in the light emitting layer of the organic EL device, it is possible to obtain an organic EL device having a long life.

[Organic EL element]
The organic EL element according to one aspect of the present invention has a cathode, an anode, and at least one organic layer arranged between the cathode and the anode, and is composed of the at least one organic layer. At least one of the layers contains the compound represented by the above formula (1).

The schematic configuration of the organic EL element of one aspect of the present invention will be described with reference to FIG.
The organic EL element 1 according to one aspect of the present invention includes a substrate 2, an anode 3, a light emitting layer 5 which is an organic layer, a cathode 10, an organic layer 4 between the anode 3 and the light emitting layer 5, and the like. It has an organic layer 6 between the light emitting layer 5 and the cathode 10.
The organic layer 4 and the organic layer 6 may be a single layer or may be composed of a plurality of layers, respectively.
Further, the organic layer 4 may include a hole transport region. The hole transport region may include a hole injection layer, a hole transport layer, an electron barrier layer, and the like. The organic layer 6 may include an electron transport area. The electron transport area may include an electron injection layer, an electron transport layer, a hole barrier layer, and the like.
The compound represented by the formula (1) is contained in the organic layer 4, the light emitting layer 5 or the organic layer 6. In one embodiment, the compound represented by the formula (1) is contained in the light emitting layer 5. The compound represented by the formula (1) can function as a dopant material in the light emitting layer 5.

In the organic EL device according to one aspect of the present invention, at least one of the at least one organic layer contains a first compound and a second compound, and the first compound is the above-mentioned compound. It is a compound represented by the formula (1).

In the organic EL element according to one aspect of the present invention, the second compound is a heterocyclic compound or a condensed aromatic compound.
In the organic EL device according to one aspect of the present invention, the second compound is an anthracene derivative.

In the organic EL device according to one aspect of the present invention, the second compound is a compound represented by the following formula (10).

<Compound represented by the formula (10)>
The compound represented by the formula (10) will be described.

[In equation (10),
Two or more adjacent pairs of R ₁₀₁ to R ₁₁₀ form a substituted or unsubstituted saturated or unsaturated ring, or do not form the substituted or unsubstituted saturated or unsaturated ring. ..
R ₁₀₁ to R ₁₁₀ , which do not form the substituted or unsaturated saturated or unsaturated ring, are independently of each other.
Hydrogen atom,
Substituent R, or a group represented by the following formula (11).
-L ₁₀₁ -Ar ₁₀₁ (11)

(In equation (11),
L ₁₀₁ is
Single bond,
It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
Ar ₁₀₁ is
It is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a monovalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms. )
The substituent R is
Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
Substituted or unsubstituted cycloalkyl group having 3 to 50 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,
It is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a monovalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
When two or more of the substituents R are present, the two or more of the substituents R may be the same or different.
_R901 to _R907 are independent of each other.
Hydrogen atom,
Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
It is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a monovalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
When two or more R ₉₀₁ to R ₉₀₇ are present, each of the two or more R ₉₀₁ to R ₉₀₇ may be the same or different.
However, at least one of R ₁₀₁ to R ₁₁₀ that does not form the substituted or unsaturated saturated or unsaturated ring is a group represented by the above formula (11). When two or more of the above formulas (11) are present, each of the two or more groups represented by the above formula (11) may be the same or different. ]
The compound represented by the above formula (10) may have a deuterium atom as a hydrogen atom.

In one embodiment, at least one of Ar ₁₀₁ in the formula (10) is a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.

In one embodiment, at least one of Ar ₁₀₁ in the formula (10) is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms.

In one embodiment, all Ar _101s in the formula (10) are substituted or unsubstituted aryl groups having 6 to 50 ring-forming carbon atoms. The plurality of Ar _101s may be the same as each other or may be different from each other.

In one embodiment, one of the Ar _101s in the formula (10) is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring-forming atoms, and the remaining Ar ₁₀₁ is substituted or absent. The substituted ring-forming aryl group has 6 to 50 carbon atoms. The plurality of Ar _101s may be the same as each other or may be different from each other.

In one embodiment, at least one of L ₁₀₁ in the formula (10) is a single bond.
In one embodiment, all of L ₁₀₁ in the formula (10) are single bonds.
In one embodiment, at least one of L ₁₀₁ in the formula (10) is a substituted or unsubstituted arylene group having 6 to 50 carbon atoms.
In one embodiment, at least one of L ₁₀₁ in the formula (10) is a substituted or unsubstituted phenylene group or a substituted or unsubstituted naphthyl group.

In one embodiment, the group represented by -L ₁₀₁ -Ar ₁₀₁ in the above formula (10) is
Substituted or unsubstituted phenyl group,
Substituted or unsubstituted naphthyl groups,
Substituted or unsubstituted biphenyl group,
Substituted or unsubstituted phenanthrenyl group,
Substituted or unsubstituted benzophenanthrenyl group,
Substituted or unsubstituted fluorenyl group,
Substituted or unsubstituted benzofluorenyl group,
Substituted or unsubstituted dibenzofuranyl group,
Substituted or unsubstituted naphthobenzofuranyl group,
It is selected from the group consisting of a substituted or unsubstituted dibenzothiophenyl group and a substituted or unsubstituted carbazolyl group.

In one embodiment, the substituents R in the formula (10) are independent of each other.
Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms,
-Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
-O- (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
A halogen atom, a cyano group, a nitro group, or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
_R901 to _R907 are as defined by the above equation (10).

In one embodiment, the "substituted or unsubstituted" substituents in the above formula (10) are independent of each other.
Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
Substituted or unsubstituted cycloalkyl group having 3 to 50 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,
It is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a monovalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
_R901 to _R907 are as defined by the above equation (10).

In one embodiment, the "substituted or unsubstituted" substituents in the above formula (10) are independent of each other.
Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms,
-Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
-O- (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
A halogen atom, a cyano group, a nitro group, or a substituted or unsubstituted aryl group having 6 to 50 carbon atoms.
_R901 to _R907 are as defined by the above equation (10).

In one embodiment, the substituent in the case of "substituent or unsubstituted" in the above formula (10) is
Alkyl groups with 1 to 18 carbon atoms,
It is selected from the group consisting of an aryl group having 6 to 18 ring-forming carbon atoms and a monovalent heterocyclic group having 5 to 18 ring-forming atoms.

In one embodiment, the substituent in the case of "substituted or unsubstituted" in the above formula (10) is an alkyl group having 1 to 5 carbon atoms.

In one embodiment, the compound represented by the formula (10) is a compound represented by the following formula (20).

(In the formula (20), R ₁₀₁ to R ₁₀₈ , L ₁₀₁ and Ar ₁₀₁ are as defined in the above formula (10).)
The compound represented by the above formula (20) may have a deuterium atom as a hydrogen atom.

That is, in one embodiment, the compound represented by the formula (10) or the formula (20) has at least two groups represented by the formula (11).
In one embodiment, the compound represented by the formula (10) or the formula (20) has two or three groups represented by the formula (11).

In one embodiment, R ₁₀₁ to R ₁₁₀ in the formulas (10) and (20) do not form the substituted or unsubstituted saturated or unsaturated ring.
In one embodiment, R ₁₀₁ to R ₁₁₀ in the formulas (10) and (20) are hydrogen atoms.

In one embodiment, the compound represented by the formula (20) is a compound represented by the following formula (30).

(In the formula (30), L ₁₀₁ and Ar ₁₀₁ are as defined by the above formula (10).
Two adjacent R _101A to R _108A do not form a substituted or unsubstituted saturated or unsaturated ring.
R _101A to R _108A are independent of each other.
It is a hydrogen atom or a substituent R.
The substituent R is as defined by the above formula (10). )

That is, the compound represented by the above formula (30) is a compound having two groups represented by the above formula (11).
The compound represented by the above formula (30) has substantially only a light hydrogen atom as a hydrogen atom.
In addition, "substantially having only a light hydrogen atom" means a compound having only a light hydrogen atom as a hydrogen atom (a light hydrogen body) and a compound having a heavy hydrogen atom (a dehydrogen body) having the same structure. It means that the ratio of the light hydrogen compound to the total of is 90 mol% or more, 95 mol% or more, or 99 mol% or more.

In one embodiment, the compound represented by the formula (30) is a compound represented by the following formula (31).

(In the formula (31), L ₁₀₁ and Ar ₁₀₁ are as defined by the above formula (10).
R _101A to R _108A are as defined by the above equation (30).
X _b is O, S, N (R ₁₃₁ ), or C (R ₁₃₂ ) (R ₁₃₃ ).
One of R ₁₂₁ to R ₁₂₈ and R ₁₃₁ to R ₁₃₃ is a single bond that binds to L ₁₀₁ .
Two or more adjacent pairs of R ₁₂₁ to R ₁₂₈ that are not single bonds bound to L ₁₀₁ form a substituted or unsaturated saturated or unsaturated ring, or the substituted or unsaturated ring. Does not form a saturated or unsaturated ring.
R ₁₂₁ to R ₁₂₈ , which are not single bonds bound to L ₁₀₁ and do not form the substituted or unsaturated saturated or unsaturated ring, are independent of each other.
It is a hydrogen atom or a substituent R.
The substituent R is as defined by the above formula (10).
R ₁₃₁ to R ₁₃₃ , which are not single bonds that bind to L ₁₀₁ , are independent of each other.
Hydrogen atom,
Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms,
It is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a monovalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
When two or more R ₁₃₁ to R ₁₃₃ are present, each of the two or more R ₁₃₁ to R ₁₃₃ may be the same or different. )

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

(In the formula (32), R _101A to R _108A , L ₁₀₁ , Ar ₁₀₁ , R ₁₂₁ to R ₁₂₈ , R ₁₃₂ and R ₁₃₃ are as defined in the above formula (31).)

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

(In the formula (33), R _101A to R _108A , L ₁₀₁ , Ar ₁₀₁ , and R ₁₂₁ to R ₁₂₈ are as defined in the above formula (31).
X _c is O, S, or NR ₁₃₁ .
R ₁₃₁ is as defined by the above equation (31). )

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

(In the formula (34), R _101A to R _108A , L ₁₀₁ and Ar ₁₀₁ are as defined in the above formula (31).
X _c is O, S or NR ₁₃₁ .
R ₁₃₁ is as defined by the above equation (31).
One of R _121A to R _128A is a single bond that binds to L ₁₀₁ .
Two or more adjacent pairs of R _121A to R _128A that are not single bonds bound to L ₁₀₁ do not form a substituted or unsubstituted saturated or unsaturated ring.
R _121A to R _128A , which are not single bonds that bind to L ₁₀₁ , are independent of each other.
It is a hydrogen atom or a substituent R.
The substituent R is as defined by the above formula (10). )

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

[In the formula (35), R _101A to R _108A , L ₁₀₁ , Ar ₁₀₁ and X _b are as defined in the above formula (31).
Two or more adjacent pairs of R _121A to R _124A do not combine with each other to form a substituted or unsubstituted saturated or unsaturated ring.
Any one set of R _125B and R _126B , R _126B and R _127B , and R _127B and R _128B are combined with each other to form a ring represented by the following formula (35a) or (35b).

(In formulas (35a) and (35b),
The two * combine with any one set of R _125B and R R _126B , R _126B and R _127B , and R _127B and R _128B , respectively.
R ₁₄₁ to R ₁₄₄ are independent of each other.
It is a hydrogen atom or a substituent R.
The substituent R is as defined by the above formula (10).
X _d is O or S. )
One of R _121A to R _124A , R _125B to R _128B which does not form a ring represented by the above formula (35a) or (35b), and R ₁₄₁ to R ₁₄₄ is a single bond which binds to L ₁₀₁ . ..
R _121A to R _124A , which are not single bonds bound to L ₁₀₁ , and R _125B to R _128B , which are not single bonds bound to L ₁₀₁ and do not form a ring represented by the above formula (35a) or (35b), are , Independently,
It is a hydrogen atom or a substituent R.
The substituent R is as defined by the above formula (10). ]

In one embodiment, the compound represented by the formula (35) is a compound represented by the following formula (36).

(In the formula (36), R _101A to R _108A , L ₁₀₁ , Ar ₁₀₁ , and R _125B to R _128B are as defined in the above formula (35).)

In one embodiment, the compound represented by the formula (34) is a compound represented by the following formula (37).

(In the formula (37), R _101A to R _108A , R _125A to R _128A , L ₁₀₁ and Ar ₁₀₁ are as defined in the above formula (34).)

In one embodiment, R _101A to R _108A in the formulas (30) to (37) are hydrogen atoms.

In one embodiment, the compound represented by the formula (10) is a compound represented by the following formula (40).

(In the formula (40), L ₁₀₁ and Ar ₁₀₁ are as defined by the above formula (10).
Two or more adjacent pairs of R _101A and R _103A to R _108A form a substituted or unsubstituted saturated or unsaturated ring, or the substituted or unsubstituted saturated or unsaturated ring. Does not form a ring.
R _101A and R _103A to R _108A , which do not form the substituted or unsaturated saturated or unsaturated ring, are independent of each other.
It is a hydrogen atom or a substituent R.
The substituent R is as defined by the above formula (10). )
That is, the compound represented by the formula (40) is a compound having three groups represented by the formula (11). Further, the compound represented by the above formula (40) has substantially only a light hydrogen atom as a hydrogen atom.

In one embodiment, the compound represented by the formula (40) is represented by the following formula (41).

(In the formula (41), L ₁₀₁ and Ar ₁₀₁ are as defined by the above formula (40).)

In one embodiment, the compound represented by the formula (40) is a compound represented by any of the following formulas (42-1) to (42-3).

(In formulas (42-1) to (42-3), R _101A to R _108A , L ₁₀₁ and Ar ₁₀₁ are as defined in the above formula (40).)

In one embodiment, the compound represented by the formulas (42-1) to (42-3) is a compound represented by any of the following formulas (43-1) to (43-3).

(In equations (43-1) to (43-3), L ₁₀₁ and Ar ₁₀₁ are as defined by the above equation (40).)

In one embodiment, it is represented by -L ₁₀₁ -Ar ₁₀₁ in the above formulas (40), (41), (42-1) to (42-3), and (43-1) to (43-3). The base is
Substituted or unsubstituted phenyl group,
Substituted or unsubstituted naphthyl groups,
Substituted or unsubstituted biphenyl group,
Substituted or unsubstituted phenanthrenyl group,
Substituted or unsubstituted benzophenanthrenyl group,
Substituted or unsubstituted fluorenyl group,
Substituted or unsubstituted benzofluorenyl group,
Substituted or unsubstituted dibenzofuranyl group,
Substituted or unsubstituted naphthobenzofuranyl group,
It is selected from the group consisting of a substituted or unsubstituted dibenzothiophenyl group and a substituted or unsubstituted carbazolyl group.

In one embodiment, the compound represented by the formula (10) or the formula (20) includes a compound in which at least one of the hydrogen atoms contained in these compounds is a deuterium atom.

In one embodiment, R ₁₀₁ to R ₁₀₈ , which are hydrogen atoms in the above formula (20),
Hydrogen atoms contained in the substituents R ₁₀₁ to R ₁₀₈ ,
Hydrogen atom of L ₁₀₁ ,
The hydrogen atom of the substituent of L ₁₀₁ ,
At least one of the hydrogen atom of Ar ₁₀₁ and the hydrogen atom of the substituent of Ar ₁₀₁ is a deuterium atom.

The compounds represented by the formulas (30) to (37) include compounds in which at least one of the hydrogen atoms contained in these compounds is a deuterium atom.
In one embodiment, at least one of the hydrogen atoms bonded to the carbon atoms constituting the anthracene skeleton in the compounds represented by the formulas (30) to (37) is a deuterium atom.

In one embodiment, the compound represented by the formula (30) is a compound represented by the following formula (30D).

(In the formula (30D), R _101A to R _108A , L ₁₀₁ and Ar ₁₀₁ are as defined in the above formula (30).
However, R _101A to R _110A , which are hydrogen atoms,
Hydrogen atoms contained in the substituents R _101A to R _110A ,
Hydrogen atom of L ₁₀₁ ,
The hydrogen atom of the substituent of L ₁₀₁ ,
At least one of the hydrogen atom of Ar ₁₀₁ and the hydrogen atom of the substituent of Ar ₁₀₁ is a deuterium atom. )
That is, the compound represented by the above formula (30D) is a compound in which at least one of the hydrogen atoms contained in the compound represented by the above formula (30) is a deuterium atom.

In one embodiment, at least one of R _101A to R _108A , which are hydrogen atoms in the formula (30D), is a deuterium atom.

In one embodiment, the compound represented by the formula (30D) is a compound represented by the following formula (31D).

(In the formula (31D), R _101A to R _108A , L ₁₀₁ and Ar ₁₀₁ are as defined in the above formula (30D).
X _d is O or S.
One of R ₁₂₁ to R ₁₂₈ is a single bond that binds to L ₁₀₁ .
Two or more adjacent pairs of R ₁₂₁ to R ₁₂₈ that are not single bonds bound to L ₁₀₁ form a substituted or unsubstituted saturated or unsaturated ring, or are substituted or unsaturated saturated. Or it does not form an unsaturated ring.
R ₁₂₁ to R ₁₂₈ , which are not single bonds bound to L ₁₀₁ and do not form the substituted or unsaturated saturated or unsaturated ring, are independent of each other.
It is a hydrogen atom or a substituent R.
The substituent R is as defined by the above formula (10).
However, R _101A to R _110A , which are hydrogen atoms,
Hydrogen atoms contained in the substituents R _101A to R _110A ,
Hydrogen atom of L ₁₀₁ ,
The hydrogen atom of the substituent of L ₁₀₁ ,
Hydrogen atom of Ar ₁₀₁ ,
At least one of the hydrogen atoms contained in the substituents of Ar ₁₀₁ , R ₁₂₁ to R ₁₂₈ , and the substituents R, R ₁₂₁ to R ₁₂₈ , is a deuterium atom. )

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

(In the formula (32D), R _101A to R _108A , R _125A to R _128A , L ₁₀₁ and Ar ₁₀₁ are as defined in the above formula (31D).
However,
R _101A to R _108A , which are hydrogen atoms,
Hydrogen atoms contained in the substituents R _101A to R _108A ,
Hydrogen atoms R _125A to R _128A ,
Hydrogen atoms contained in the substituents R _125A to R _128A ,
A hydrogen atom bonded to a carbon atom of the dibenzofuran skeleton in formula (32D),
Hydrogen atom of L ₁₀₁ ,
The hydrogen atom of the substituent of L ₁₀₁ ,
At least one of the hydrogen atom of Ar ₁₀₁ and the hydrogen atom of the substituent of Ar ₁₀₁ is a deuterium atom. )

In one embodiment, the compound represented by the formula (32D) is a compound represented by the following formula (32D-1) or (32D-2).

(In the formulas (32D-1) and (32D-2), R _101A to R _108A , R _125A to R _128A , L ₁₀₁ and Ar ₁₀₁ are as defined in the above formula (32D).
However,
R _101A to R _108A , which are hydrogen atoms,
Hydrogen atoms contained in the substituents R _101A to R _108A ,
Hydrogen atoms R _125A to R _128A ,
Hydrogen atoms contained in the substituents R _125A to R _128A ,
A hydrogen atom bonded to a carbon atom of the dibenzofuran skeleton in the formulas (32D-1) and (32D-2),
Hydrogen atom of L ₁₀₁ ,
The hydrogen atom of the substituent of L ₁₀₁ ,
At least one of the hydrogen atom of Ar ₁₀₁ and the hydrogen atom of the substituent of Ar ₁₀₁ is a deuterium atom. )

In one embodiment, among the hydrogen atoms contained in the compounds represented by the formulas (40), (41), (42-1) to (42-3) or (43-1) to (43-3). At least one of them is a deuterium atom.

In one embodiment, at least one of the hydrogen atoms (hydrogen atoms R _101A to R _108A ) bonded to the carbon atom constituting the anthracene skeleton in the compound represented by the above formula (41) is a heavy hydrogen atom. Is.

In one embodiment, the compound represented by the formula (40) is a compound represented by the following formula (40D).

(In the formula (40D), L ₁₀₁ and Ar ₁₀₁ are as defined by the above formula (10).
Two or more adjacent pairs of R _101A and R _103A to R _108A do not form a substituted or unsubstituted saturated or unsaturated ring.
R _101A and R _103A to R _108A are independent of each other.
It is a hydrogen atom or a substituent R.
The substituent R is as defined by the above formula (10).
However, R _101A and R _103A to R _108A , which are hydrogen atoms,
The hydrogen atoms contained in R _101A , which is the substituent R, and R _103A to R _108A ,
Hydrogen atom of L ₁₀₁ ,
The hydrogen atom of the substituent of L ₁₀₁ ,
The hydrogen atom of Ar ₁₀₁ and the hydrogen atom of the substituent of Ar ₁₀₁ ,
At least one of them is a deuterium atom. )

In one embodiment, at least one of R _101A and R _103A to R _108A in the formula (40D) is a deuterium atom.

In one embodiment, the compound represented by the formula (40D) is a compound represented by the following formula (41D).

(In the formula (41D), L ₁₀₁ and Ar ₁₀₁ are as defined by the above formula (40D).
However, the hydrogen atom bonded to the carbon atom constituting the anthracene skeleton in the formula (41D),
Hydrogen atom of L ₁₀₁ ,
The hydrogen atom of the substituent of L ₁₀₁ ,
The hydrogen atom of Ar ₁₀₁ and the hydrogen atom of the substituent of Ar ₁₀₁ ,
At least one of them is a deuterium atom. )

In one embodiment, the compound represented by the formula (40D) is a compound represented by any of the following formulas (42D-1) to (42D-3).

(In the formulas (42D-1) to (42D-3), R _101A to R _108A , L ₁₀₁ and Ar ₁₀₁ are as defined by the above formula (40D).
However, R _101A and R _103A to R _108A , which are hydrogen atoms in the above formula (42D-1),
The hydrogen atoms contained in R _101A , which is the substituent R, and R _103A to R _108A ,
Hydrogen atom of L ₁₀₁ ,
The hydrogen atom of the substituent of L ₁₀₁ ,
Hydrogen atom of Ar ₁₀₁ ,
At least one of the hydrogen atom contained in the substituent of Ar ₁₀₁ and the hydrogen atom bonded to the carbon atom constituting the phenyl group in the above formula (42D-1) is a heavy hydrogen atom.
R _101A and R _103A to R _108A , which are hydrogen atoms in the above formula (42D-2),
The hydrogen atoms contained in R _101A , which is the substituent R, and R _103A to R _108A ,
Hydrogen atom of L ₁₀₁ ,
The hydrogen atom of the substituent of L ₁₀₁ ,
Hydrogen atom of Ar ₁₀₁ ,
At least one of the hydrogen atom contained in the substituent of Ar ₁₀₁ and the hydrogen atom bonded to the carbon atom constituting the naphthyl group in the above formula (42D-2) is a heavy hydrogen atom.
R _101A and R _103A to R _108A , which are hydrogen atoms in the above formula (42D-3),
The hydrogen atoms contained in R _101A , which is the substituent R, and R _103A to R _108A ,
Hydrogen atom of L ₁₀₁ ,
The hydrogen atom of the substituent of L ₁₀₁ ,
Hydrogen atom of Ar ₁₀₁ ,
At least one of the hydrogen atom contained in the substituent of Ar ₁₀₁ and the hydrogen atom bonded to the carbon atom constituting the naphthyl group in the above formula (42D-3) is a heavy hydrogen atom. )

In one embodiment, the compound represented by the formulas (42D-1) to (42D-3) is a compound represented by any of the following formulas (43D-1) to (43D-3).

(In the formulas (43D-1) to (43D-3), L ₁₀₁ and Ar ₁₀₁ are as defined by the above formula (40D).
However, the hydrogen atom bonded to the carbon atom constituting the anthracene skeleton in the above formula (43D-1),
Hydrogen atom of L ₁₀₁ ,
The hydrogen atom of the substituent of L ₁₀₁ ,
Hydrogen atom of Ar ₁₀₁ ,
At least one of the hydrogen atom contained in the substituent of Ar ₁₀₁ and the hydrogen atom bonded to the carbon atom constituting the phenyl group in the above formula (43D-1) is a heavy hydrogen atom.
A hydrogen atom bonded to a carbon atom constituting the anthracene skeleton in the above formula (43D-2),
Hydrogen atom of L ₁₀₁ ,
The hydrogen atom of the substituent of L ₁₀₁ ,
Hydrogen atom of Ar ₁₀₁ ,
At least one of the hydrogen atom contained in the substituent of Ar ₁₀₁ and the hydrogen atom bonded to the carbon atom constituting the naphthyl group in the above formula (43D-2) is a heavy hydrogen atom.
A hydrogen atom bonded to a carbon atom constituting the anthracene skeleton in the above formula (43D-3),
Hydrogen atom of L ₁₀₁ ,
The hydrogen atom of the substituent of L ₁₀₁ ,
Hydrogen atom of Ar ₁₀₁ ,
At least one of the hydrogen atom contained in the substituent of Ar ₁₀₁ and the hydrogen atom bonded to the carbon atom constituting the naphthyl group in the above formula (43D-3) is a heavy hydrogen atom. )

In one embodiment, in the compound represented by the formula (20), at least one of Ar ₁₀₁ is a monovalent group having a structure represented by the following formula (50).

(In formula (50),
X ₁₅₁ is O, S or C (R ₁₆₁ ) (R ₁₆₂ ).
One of R ₁₅₁ to R ₁₆₀ is a single bond that binds to L ₁₀₁ .
Two or more adjacent pairs of R ₁₅₁ to R ₁₅₄ and one or more pairs of adjacent two or more of R ₁₅₅ to R ₁₆₀ , which are not single bonds bound to L ₁₀₁ , are coupled to each other and replaced or none. It forms a saturated or unsaturated ring of substitutions, or does not form a saturated or unsaturated ring of substitutions or unsaturateds.
R ₁₆₁ and R ₁₆₂ 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 ₁₆₁ and R ₁₆₂ that do not form the substituted or unsubstituted saturated or unsaturated ring, and R ₁₅₁ that is not a single bond that binds to L ₁₀₁ and does not form the substituted or unsubstituted saturated or unsaturated ring. ~ R ₁₆₀ are each independently a hydrogen atom or a substituent R.
The substituent R is as defined by the above formula (10).
Ar ₁₀₁ , which is not a monovalent group having a structure represented by the above formula (50), is
It is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms. )

The position of the single bond with L ₁₀₁ in the above formula (50) is not particularly limited.
In one embodiment, one of R ₁₅₁ to R ₁₅₄ or one of R ₁₅₅ to R ₁₆₀ in the formula (50) is a single bond that binds to L ₁₀₁ .

In one embodiment, Ar ₁₀₁ is represented by the following formula (50-R ₁₅₂ ), (50-R ₁₅₃ ), (50-R ₁₅₄ ), (50-R ₁₅₇ ) or (50-R ₁₅₈ ). It is the basis of monovalent.

In the formulas (50-R ₁₅₂ ), (50-R ₁₅₃ ), (50-R ₁₅₄ ), (50-R ₁₅₇ ) and (50-R ₁₅₈ ), X ₁₅₁ and R ₁₅₁ to R ₁₆₀ are the above-mentioned formulas. As defined in (50).
* Combines with L ₁₀₁ . )

Specific examples of the compound represented by the formula (10) include the compounds shown below. The compound represented by the formula (10) is not limited to these specific examples. In the specific examples below, D represents a deuterium atom.

As described above, the organic EL device according to one aspect of the present invention has a light emitting layer between a cathode, an anode, and the cathode and the anode, and the light emitting layer is represented by the formula (1). Conventionally known materials and device configurations can be applied as long as the effects of the present invention are not impaired, except that the compound is contained.
The content of the compound represented by the formula (1) in the light emitting layer is preferably 1% by mass or more and 20% by mass or less with respect to the entire light emitting layer.

In one embodiment, the compound having the same structure as the compound represented by the formula (1) in the light emitting layer and the compound represented by the formula (1) except that it contains only a light hydrogen atom as a hydrogen atom (hereinafter referred to as a compound). The content ratio of the latter to the total with "light hydrogen compound") is 99 mol% or less. The content ratio of the light hydrogen compound is confirmed by mass spectrometry.

As a typical element configuration of the organic EL element of the present invention,
(1) Anodic / 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) cathode / 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 improvement 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 / Insulation layer / Light emitting layer / Insulation layer / Cathode (11) Anodic / Organic semiconductor layer / Insulation layer / Light emitting layer / Insulation layer / Cathode (12) Adenator / Insulation layer / Hole injection / transport layer / Light emitting layer / Insulation layer / Cathode (13) The structure of the anode / insulating layer / hole injection / transport layer / light emitting layer / electron injection / transport layer / cathode and the like can be mentioned.
Of the above, the configuration of (8) is preferably used, but 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". It means "at least one of the transport layers".

Hereinafter, a member that can be used in the organic EL device according to one aspect of the present invention, materials other than the above compounds constituting each layer, and the like will be described.

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

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

(Hole injection layer)
The hole injection layer is a layer containing a substance having a high hole injection property. Substances with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, renium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, and silver oxide. Tungsten oxides, manganese oxides, aromatic amine compounds, polymer compounds (oligoforms, dendrimers, polymers, etc.) and the like can also be used.

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

(Guest (dopant) material of light emitting layer)
The light emitting layer is a layer containing a substance having high light emitting property, and various materials can be used in addition to the material used in the present invention described above (the compound represented by the formula (1)). For example, as a substance having high luminescence, a fluorescent compound that emits fluorescence or a phosphorescent compound that emits phosphorescence can be used. A fluorescent compound is a compound capable of emitting light from a singlet excited state, and a phosphorescent compound is a compound capable of emitting light from a triplet excited state.
As the 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 and 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, or 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. As the red 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.

(Host material of light emitting layer)
The light emitting layer may have a structure in which the above-mentioned highly luminescent substance (guest material) is dispersed in another substance (host material). As the substance for dispersing the highly luminescent substance, various substances can be used in addition to the material (compound represented by the formula (10)) used in the present invention described above, and the substance has high luminescence. It is preferable to use a substance having a higher minimum empty orbital level (LUMO level) and a lower maximum occupied molecular orbital level (HOMO level) than the substance.
Examples of the substance (host material) for dispersing a highly luminescent substance include 1) a metal complex such as an aluminum complex, a berylium complex, or a zinc complex, and 2) an oxadiazole derivative, a benzoimidazole derivative, a phenanthroline derivative, or the like. Condensed aromatic compounds such as heterocyclic compounds, 3) carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, naphthacene derivatives, fluoranthene derivatives, triphenylene derivatives, fluorene derivatives, or chrysene derivatives, 3) triarylamine derivatives, or condensed poly. Aromatic amine compounds such as ring aromatic amine derivatives are used.
Further, a compound having delayed fluorescence (thermally activated delayed fluorescence) can also be used as the host material. It is also preferable that the light emitting layer contains the material used in the present invention described above and the delayed fluorescent host compound.

(Electron transport layer)
The electron transport layer is a layer containing a substance having a high electron transport property. The electron transport layer includes 1) a metal complex such as an aluminum complex, a berylium complex, and a zinc complex, 2) a complex aromatic compound such as an imidazole derivative, a benzimidazole derivative, an azine derivative, a carbazole derivative, and a phenanthroline derivative, and 3) a polymer compound. Can be used.

(Electron injection layer)
The electron injection layer is a layer containing a substance having a high electron injection property. The electron injection layer includes lithium (Li), itterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), 8-hydroxyquinolinolato-lithium (Liq), etc. Metal complex compounds of the above, alkali metals such as lithium oxide (LiO _x ), alkaline earth metals, or compounds thereof can be used.

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

In the organic EL device according to one aspect of the present invention, the method for forming each layer is not particularly limited. Conventionally known forming methods such as a vacuum vapor deposition method and a spin coating method can be used. Each layer such as a light emitting layer is known by a vacuum vapor deposition method, a molecular beam epitaxy method (MBE method), 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 device according to one aspect of the present invention, the film thickness of each layer is not particularly limited, but generally, in order to suppress defects such as pinholes, keep the applied voltage low, and improve the luminous efficiency, it is usually from several nm. A range of 1 μm is preferred.

[Electronics]
The electronic device according to one aspect of the present invention is characterized by comprising an organic EL element according to one aspect of the present invention.
Specific examples of electronic devices include display components such as organic EL panel modules, display devices such as televisions, mobile phones, and personal computers, and light emitting devices such as lighting or lighting equipment for vehicles.

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

<Compound>
The compound represented by the formula (1) used in the examples is shown below.

The compounds used in the comparative examples are shown below.

The compounds used in Examples and Comparative Examples are shown below.

Example 1
<Manufacturing of organic EL element>
A glass substrate (manufactured by Geomatic Co., Ltd.) with an ITO transparent electrode (anode) having a thickness of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 30 minutes. The film thickness of ITO was 130 nm.
The cleaned glass substrate with a transparent electrode is attached to the substrate holder of the vacuum vapor deposition apparatus, and compound HI-1 is first vapor-deposited on the surface on the side where the transparent electrode is formed so as to cover the transparent electrode, and the film thickness is 5 nm. The compound HI-1 film of the above was formed. This HI-1 membrane functions as a hole injection layer.

Following the film formation of the HI-1 film, the compound HT-1 was deposited to form an HT-1 film having a film thickness of 80 nm on the HI-1 film. This HT-1 membrane functions as a first hole transport layer.
Following the film formation of the HT-1 film, the compound EBL-1 was deposited to form an EBL-1 film having a film thickness of 10 nm on the HT-1 film. This EBL-1 membrane functions as a second hole transport layer.
BH-1 (host material) and BD-1 (dopant material) are co-deposited on the EBL-1 film so that the ratio (weight ratio) of the compound BD-1 is 2%, and a light emitting layer having a film thickness of 25 nm is formed. A film was formed.

Compound HBL-1 was deposited on this light emitting layer to form an electron transport layer having a film thickness of 10 nm. The compound ET-1, which is an electron injection material, was vapor-deposited on the electron transport layer to form an electron injection layer having a film thickness of 15 nm. LiF was deposited on the electron injection layer to form a LiF film having a film thickness of 1 nm. A metal Al was deposited on the LiF film to form a metal cathode having a film thickness of 80 nm.

The element configuration of the organic EL element of the first embodiment is schematically as follows.
ITO (130) / HI-1 (5) / HT-1 (80) / EBL-1 (10) / BH-1: BD-1 (25: 2%) / HBL-1 (10) / ET-1 (15) / LiF (1) / Al (80)
The numbers in parentheses indicate the film thickness (unit: nm).

<Evaluation of organic EL element>
(Element life)
With respect to the obtained organic EL element, a voltage is applied to the organic EL element so that the current density becomes 50 mA / cm ² at room temperature, and the time until the brightness becomes 95% with respect to the initial brightness (LT95 (unit: unit:). Time)) was measured. The numerical values in the table are relative values when Comparative Example 1 described later is set to 100%.

Examples 2-3
An organic EL device was produced and evaluated by the same method as in Example 1 except that the compound shown in Table 1 was used as the dopant material of the light emitting layer. The results are shown in Table 1.

Comparative Example 1
An organic EL device was produced and evaluated by the same method as in Example 1 except that BD-Ref was used as the dopant material of the light emitting layer. The results are shown in Table 1.

<Compound synthesis>
(Synthesis Example 1) Synthesis of BD-1 Compound BD-1 was synthesized by the following synthetic route.
(1-1) Synthesis of compound 5

2,7-Dimethoxynaphthalene (Compound 1) (10 g, 53.1 mmol) was dissolved in tetrahydrofuran (THF) (200 mL) under an argon atmosphere. A solution of 1.6 mmol / L n-butyllithium (n-BuLi) in xan (36.5 mL) was added dropwise thereto at −10 ° C. After the dropping, iron (III) acetyl acetylase (Fe (acac) ₃ ) (20.6 g, 58.4 mmol, 1.1 eq) was added with stirring at −10 ° C. for 2 hours. After the addition, the temperature was raised to room temperature, and after the temperature was raised, the mixture was stirred for 4 hours. After stirring, it was allowed to stand overnight. After allowing to stand overnight, the precipitated solid was filtered through Serai and washed with hexane. The obtained residue was purified by column chromatography (100% toluene) and washed with hexane to obtain 4.42 g (yield 45%) of a white solid. The molecular weight of compound 2 was 374.43, and the mass-to-charge analysis result of the obtained white solid was m / z (mass-to-charge ratio) = 374. Therefore, the white solid is compound 2. It was confirmed.

Under an argon atmosphere, 4.35 g (11.6 mmol) of the above compound 2 was dissolved in methylene chloride (40 mL). A 1 mol / L boron tribromide (BBr ₃ ) methylene chloride solution (48.8 mL) was added dropwise thereto at −10 ° C. After the dropping, the mixture was stirred at room temperature for 4 hours and then allowed to stand overnight. The reaction solution, which had been allowed to stand overnight, was added to ice water, and the precipitated solid was collected by filtration. The obtained solid was purified by column chromatography (100% ethyl acetate) to obtain 3.45 g (yield 93%) of a brown solid. The molecular weight of the compound 3 was 318.32, and the mass-spectral analysis result of the obtained brown solid was m / z = 318. Therefore, it was confirmed that the brown solid was the compound 3.

Under an argon atmosphere, 3.1 g (9.7 mmol) of the above compound 3, zeolite HSZ-360HUA (Zeolite, manufactured by Tosoh Corporation) (1.24 g), and ortodichlorobenzene (o-DCB) ( 180 mL) was mixed and stirred at 160 ° C. for 6 hours. After stirring, the mixture was cooled to room temperature and allowed to stand overnight. After standing overnight, the precipitated solid was filtered and washed with methanol. The obtained solid was extracted with tetrahydrofuran to obtain 1.74 g (yield 60%) of a brown solid. Since the molecular weight of the compound 4 was 30.31 and the mass-speculous analysis result of the obtained brown solid was m / z = 300, it was confirmed that the brown solid was the compound 4.

Under an argon atmosphere, 1.5 g (5.0 mmol) of compound 4, pyridine (pyridine) (10 mL), and methylene chloride (25 mL) were mixed, and an anhydrous liffler (Tf ₂ O) was mixed therein at 0 ° C. ) (2.1 mL, 13.5 mmol) was added dropwise. After the dropping, the mixture was stirred at room temperature for 1 hour, methanol was added to stop the reaction, and a reaction solution was obtained. Water was added to the obtained reaction solution, methylene chloride was removed by concentration under reduced pressure, and the solid was precipitated. The precipitated solid was collected by filtration and washed with methanol to obtain 2.6 g (yield 86%) of a white solid. Since the molecular weight of the compound 5 was 564.43 and the mass spectral analysis result of the obtained white solid was m / z = 564, it was confirmed that the white solid was the compound 5.

(1-2) Synthesis of BD-1

Bis (phenyl-d5) amine (1.05 g, synthesized by the method described in Chemistry-A European Journal, 2015, 21 (24), 8723), compound 5 (1.5 g), tris (dibenzylideneacetone) dipalladium. (0) (0.05 g), di-tert-butyl (1-methyl-2,2-diphenylcyclopropyl) phosphine (cBRIDP, 0.075 g) is dissolved in toluene (50 mL) and heated to 70 ° C. in an argon atmosphere. Heated to. A toluene solution (1.0 M, 6.0 mL) of lithium bis (trimethylsilyl) amide (LiHMDS) was added dropwise to this reaction solution, and the mixture was then stirred at 70 ° C. for 4 hours. The obtained reaction solution was concentrated under reduced pressure, the residue was dissolved in ethyl acetate, hexane was added, and the precipitated solid was collected by filtration to obtain 0.9 g (55%) of a yellow solid. The molecular weight of compound BD-1 was 622.86, and the analysis result of the mass spectrum of the obtained compound was m / z = 622. Therefore, it was identified as BD-1.

(Synthesis Example 2) Synthesis of BD-2 Compound BD-2 was synthesized by the following synthetic route.
(2-1) Synthesis of compound 6

The reaction was carried out according to the method of the literature (Org. Process Res. Dev. 2019, 23, 648-653). 2,7-Dimethoxynaphthalene (0.2 g, manufactured by Tokyo Kasei Kogyo Co., Ltd.), platinum-supported carbon (10%, 0.06 g, manufactured by Sigma-Aldrich), 2-propanol (2.0 mL) in heavy water (4.0 mL) ) And stirred overnight in an argon atmosphere. After filtering the reaction mixture, the filtrate was extracted with ethyl acetate and concentrated under reduced pressure to give a white solid (0.18 g, 90%). Since the molecular weight of compound 6 was 194.26 and the analysis result of the mass spectrum of the obtained compound was m / z = 194, it was identified as compound 6.

(2-2) Synthesis of compound 10

Compound 10 was synthesized in the same manner as in Synthesis Example 1 (1-1) except that compound 6 (10 g) was used as a starting material instead of compound 1. The molecular weight of compound 10 was 574.49, and the analysis result of the mass spectrum of the obtained compound was m / z = 574. Therefore, it was identified as compound 10.

(2-3) Synthesis of BD-2

BD-2 was synthesized in the same manner as in (1-2) of Synthesis Example 1 except that compound 10 was used instead of compound 5. The m / z of BD-2 was 612.80, and the analysis result of the mass spectrum of the obtained compound was m / z = 612. Therefore, it was identified as BD-2.

(Synthesis Example 3) Synthesis of BD-3 Compound BD-3 was synthesized by the following synthetic route.

BD-3 was synthesized in the same manner as in (2-3) of Synthesis Example 2 except that bis (phenyl-d5) amine was used instead of diphenylamine. The m / z of BD-2 was 632.92, and the analysis result of the mass spectrum of the obtained compound was m / z = 632, so that it was identified as BD-3.

Claims (29)

A compound represented by the following formula (1).

(In equation (1)
R ₁ to R ₁₀ are hydrogen atoms.
L ₁ to L ₄ are independent of each other.
Single bond,
It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
L ₁ and L ₂ are either single-bonded to each other or not single-bonded to each other.
L ₃ and L ₄ are either single-bonded to each other or not single-bonded to each other.
Ar ₁ to Ar ₄ are independent of each other.
It is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a monovalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
When L ₁ and L ₂ are single bonds, Ar ₁ and Ar ₂ either bind to each other in a single bond or do not bind to each other in a single bond.
When L ₃ and L ₄ are single bonds, Ar ₃ and Ar ₄ either bind to each other in a single bond or do not bind to each other in a single bond.
The substituent in the case of "substituent or unsubstituted" is
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,
-Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
-O- (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ )
(Here, R ₉₀₁ to R ₉₀₇ are independent of each other.
Hydrogen atom,
Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms,
It is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a monovalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms. When two or more R ₉₀₁ to R ₉₀₇ are present, 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 selected from the group consisting of an aryl group having an unsubstituted ring-forming carbon number of 6 to 50 and a monovalent heterocyclic group having an unsubstituted ring-forming atom number of 5 to 50.
Hydrogen atoms of R ₁ to R ₁₀ , L ₁ to L ₄ , hydrogen atoms of Ar ₁ to Ar ₄ , hydrogen atoms of substituents when L ₁ to L ₄ are substituted, and Ar ₁ to Ar. One or more of the hydrogen atoms of the substituent when ₄ is substituted is a deuterium atom. ) The hydrogen atom of L ₁ to L ₄ , the hydrogen atom of Ar ₁ to Ar ₄ , the hydrogen atom of the substituent when L ₁ to L ₄ is substituted, and the hydrogen atom of Ar ₁ to Ar ₄ are substituted. The compound according to claim 1, wherein one or more of the hydrogen atoms contained in the substituent is a deuterium atom. The compound according to claim 1 or 2, wherein one or more of the hydrogen atoms contained in L ₁ to L ₄ and the hydrogen atoms contained in the substituents when L ₁ to L ₄ are substituted are heavy hydrogen atoms. .. The compound according to any one of claims 1 to 3, wherein one or more of R ₁ to R ₁₀ is a deuterium atom. One or more of R ₁ to R ₁₀ are deuterium atoms.
The hydrogen atom of L ₁ to L ₄ , the hydrogen atom of Ar ₁ to Ar ₄ , the hydrogen atom of the substituent when L ₁ to L ₄ is substituted, and the hydrogen atom of Ar ₁ to Ar ₄ are substituted. The compound according to any one of claims 1 to 4, wherein one or more of the hydrogen atoms contained in the substituent is a deuterium atom. The compound according to claim 1, wherein the compound represented by the formula (1) is a compound represented by the following formula (1-1).

(In the formula (1-1), R ₁ to R ₁₀ and Ar ₁ to Ar ₄ are as defined in the above formula (1).
One or more of the hydrogen atoms contained in R ₁ to R ₁₀ , Ar ₁ to Ar ₄ , and the hydrogen atoms contained in the substituents when Ar ₁ to Ar ₄ are substituted are deuterium atoms. ) The compound according to claim 6, wherein one or more of the hydrogen atoms contained in Ar ₁ to Ar ₄ and the hydrogen atoms contained in the substituents when Ar ₁ to Ar ₄ are substituted are heavy hydrogen atoms. The compound according to claim 6 or 7, wherein one or more of R ₁ to R ₁₀ is a deuterium atom. One or more of R ₁ to R ₁₀ are deuterium atoms.
The hydrogen atom of Ar ₁ to Ar ₄ and one or more of the hydrogen atoms of the substituent when Ar ₁ to Ar ₄ are substituted are all deuterium atoms according to any one of claims 6 to 8. The compound described. The compound according to claim 1, wherein the compound represented by the formula (1) is a compound represented by the following formula (1-2).

(In the formula (1-2), R ₁ to R ₁₀ are as defined in the above formula (1).
Two or more adjacent pairs of R ₂₁ to R ₄₀ combine with 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 substituted or unsubstituted Saturated or unsaturated rings R ₂₁ to R ₄₀ are independently hydrogen atoms or substituents R, respectively.
Substituent R is
Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
Substituted or unsubstituted cycloalkyl group having 3 to 50 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,
It is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a monovalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
When two or more of the substituents R are present, the two or more of the substituents R may be the same or different.
_R901 to _R907 are as defined by the above equation (1).
One or more of the hydrogen atoms contained in R ₁ to R ₁₀ , hydrogen atoms R ₂₁ to R ₄₀ , and substituents R R ₂₁ to R ₄₀ are deuterium atoms. ) The compound according to claim 10, wherein one or more of the hydrogen atoms contained in the hydrogen atoms R ₂₁ to R ₄₀ and the substituent R R ₂₁ to R ₄₀ are deuterium atoms. The compound according to claim 10 or 11, wherein one or more of R ₁ to R ₁₀ is a deuterium atom. One or more of R ₁ to R ₁₀ are deuterium atoms.
The compound according to any one of claims 10 to 12, wherein one or more of the hydrogen atoms contained in R ₂₁ to R ₄₀ which are hydrogen atoms and R ₂₁ to R ₄₀ which are substituents R are deuterium atoms. A material for an organic electroluminescence device containing the compound according to any one of claims 1 to 13. A compound represented by the formula (1) according to any one of claims 1 to 13 and a compound having the same structure as the compound represented by the formula (1) except that it contains only a light hydrogen atom as a hydrogen atom. The material for an organic electroluminescence element according to claim 14, wherein the content ratio of the former to the total thereof is 1 mol% or more. With the cathode
With the anode
At least one organic layer arranged between the cathode and the anode,
Have,
An organic electroluminescence device in which at least one of the at least one organic layer contains the compound according to any one of claims 1 to 13. The organic electroluminescence device according to claim 16, wherein at least one of the at least one organic layer contains a second compound that is not the same as the first compound according to any one of claims 1 to 13. .. The organic electroluminescence element according to claim 17, wherein the second compound is a heterocyclic compound or a condensed aromatic compound. The organic electroluminescence device according to claim 17 or 18, wherein the second compound is an anthracene derivative. The organic electroluminescence device according to any one of claims 17 to 19, wherein the second compound is a compound represented by the following formula (20).

Two or more adjacent pairs of R ₁₀₁ to R ₁₀₈ form a substituted or unsubstituted saturated or unsaturated ring, or do not form the substituted or unsubstituted saturated or unsaturated ring. ..
R ₁₀₁ to R ₁₀₈ , which do not form the substituted or unsaturated saturated or unsaturated ring, are independently of each other.
It is a group represented by a hydrogen atom or a substituent R.
L ₁₀₁ is
Single bond,
It is an arylene group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a divalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
Ar ₁₀₁ is
It is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a monovalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
The substituent R is
Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
Substituentally or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
Substituted or unsubstituted cycloalkyl group having 3 to 50 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,
It is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a monovalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
The two Ar _101s may be the same or different from each other.
The two L _101s may be the same or different from each other.
When two or more of the substituents R are present, the two or more of the substituents R may be the same or different.
_R901 to _R907 are independent of each other.
Hydrogen atom,
Substituentally substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms,
It is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms, or a monovalent heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.
When two or more R ₉₀₁ to R ₉₀₇ are present, each of the two or more R ₉₀₁ to R ₉₀₇ may be the same or different. The organic electroluminescence device according to any one of claims 16 to 20, wherein at least one of the at least one organic layer is a light emitting layer. The organic electroluminescence element according to claim 21, wherein the light emitting layer contains the compound according to any one of claims 1 to 13 as a fluorescent dopant. The light emitting layer is the same as the compound represented by the formula (1) except that the light emitting layer contains only the compound represented by the formula (1) according to any one of claims 1 to 13 and a light hydrogen atom as a hydrogen atom. The organic electroluminescence element according to claim 21 or 22, which comprises a compound having a structure, and the content ratio of the former to the total thereof is 1% by mass or more. The organic electroluminescence device according to any one of claims 21 to 23, which has a hole transport layer between the anode and the light emitting layer. The organic electroluminescence device according to any one of claims 21 to 24, which has an electron transport layer between the cathode and the light emitting layer. The organic electroluminescence device according to any one of claims 21 to 25, wherein the light emitting layer contains a compound represented by the formula (20). The electroluminescent layer contains a compound represented by the formula (1) according to any one of claims 1 to 13 and a compound represented by the formula (20), and the content ratio of the former to the total thereof is The organic electroluminescence element according to any one of claims 21 to 26, which is 1 to 20% by mass. The organic electroluminescence device according to any one of claims 21 to 27, wherein the light emitting layer further contains a delayed fluorescent host compound. An electronic device comprising the organic electroluminescence device according to any one of claims 16 to 28.

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