JP2023155624A - Compound, organic electroluminescent element material, organic electroluminescent element, and electronic apparatus - Google Patents

Abstract

To provide a compound with which a higher-performance organic EL element can be obtained.SOLUTION: The invention provides a compound represented by formula (1).SELECTED DRAWING: None

Description

The present invention relates to a novel compound, a material for an organic electroluminescent device, an organic electroluminescent device, and an electronic device.

When a voltage is applied to an organic electroluminescent device (hereinafter also referred to as an organic EL device), 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 recombine to form excitons.
Conventional organic EL devices still have insufficient device performance. Although improvements in materials used in organic EL devices are gradually being made in order to improve device performance, there is a need for even higher performance.
Patent Documents 1 to 3 disclose the use of a compound having a specific structure in an organic layer of an organic EL element.

International Publication No. 2018/225940 Korean Published Patent No. 2020-0068398 International Publication No. 2013/077352

An object of the present invention is to provide a compound that can realize a higher performance organic EL device.

［式（１）中、
ＹはＯ又はＳである。
Ｒ_１～Ｒ_４のうちいずれか１つはＬ_１との結合を表す。Ｌ_１との結合を表さないＲ_１～Ｒ_４の少なくとも１つはＡｒ_１である。
Ａｒ_１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環形成炭素数６～１０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。ただし、前記環形成炭素数６～１０のアリール基における「置換もしくは無置換の」という場合の置換基はアリール基ではない。Ａｒ_１が２以上存在する場合、２以上のＡｒ_１のそれぞれは同一でもよく、異なってもよい。
Ｌ_１との結合を表さず、かつ、Ａｒ_１でもないＲ_１～Ｒ_４は、それぞれ独立に、水素原子又は置換基Ｒである。Ｌ_１との結合を表さないＲ_１～Ｒ_４のうち隣接する２つ以上からなる組は互いに結合しない。
Ｒ_５～Ｒ_８のうち隣接する２つ以上からなる組の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_５～Ｒ_８は、それぞれ独立に、水素原子又は置換基Ｒである。
Ｌ_１は、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。
ｎ１は０～２の整数であり、ｎ１が０である場合、（Ｌ_１）_ｎ１は単結合である。Ｌ_１が複数存在する場合、複数のＬ_１のそれぞれは同一でもよく、異なってもよい。
Ｒ_１１及びＲ_１２は、それぞれ独立に、水素原子又は置換基Ｒである。Ｒ_１１及びＲ_１２は互いに結合しない。
Ｒ_１３～Ｒ_１６のうち隣接する２つ以上からなる組の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_１３～Ｒ_１６は、それぞれ独立に、水素原子又は置換基Ｒである。
Ｘ_１～Ｘ_３は、それぞれ独立に、Ｎ又はＣ（Ｒ_２１）であり、Ｘ_１～Ｘ_３のうち少なくとも２つはＮである。Ｒ_２１は、水素原子又は置換基Ｒである。
Ａｒ_２及びＡｒ_３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_２及びＬ_３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。
ｎ２は０～２の整数であり、ｎ２が０である場合、（Ｌ_２）_ｎ２は単結合である。Ｌ_２が複数存在する場合、複数のＬ_２のそれぞれは同一でもよく、異なってもよい。
ｎ３は０～２の整数であり、ｎ３が０である場合、（Ｌ_３）_ｎ３は単結合である。Ｌ_３が複数存在する場合、複数のＬ_３のそれぞれは同一でもよく、異なってもよい。
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）
（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、異なってもよい。）、
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、及び
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
からなる群から選択される。
置換基Ｒが２以上存在する場合、２以上の置換基Ｒは同一でもよく、異なってもよい。］
２．陰極と、
陽極と、
前記陰極と前記陽極との間に配置された１又は２以上の有機層と、
を有し、
前記有機層のうちの少なくとも１層が、１．に記載の化合物を含む、有機エレクトロルミネッセンス素子。
３．２．に記載の有機エレクトロルミネッセンス素子を備える電子機器。 As a result of intensive research to achieve the above object, the present inventors discovered that a higher performance organic EL device could be obtained by using a compound having a specific structure, and completed the present invention.
According to the present invention, the following compounds and the like are provided.
1. A compound represented by the following formula (1).

[In formula (1),
Y is O or S.
Any one of R ₁ to R ₄ represents a bond with L ₁ . At least one of R ₁ to R ₄ that does not represent a bond with L ₁ is Ar ₁ .
Ar ₁ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 ring atoms, or a substituted or unsubstituted monovalent group having 5 to 50 ring atoms; is a heterocyclic group. However, in the above-mentioned aryl group having 6 to 10 ring carbon atoms, the substituent in the term "substituted or unsubstituted" is not an aryl group. When two or more Ar ₁ 's exist, each of the two or more Ar ₁ 's may be the same or different.
R ₁ to R ₄ that do not represent a bond with L ₁ and are not Ar ₁ are each independently a hydrogen atom or a substituent R. A set of two or more adjacent ones of R ₁ to R ₄ that do not represent a bond with L ₁ does not bond to each other.
One or more of the groups consisting of two or more adjacent ones of R ₅ to R ₈ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or Does not form unsaturated rings.
The substituted or unsubstituted saturated or unsaturated ring-forming R ₅ to R ₈ are each independently a hydrogen atom or a substituent R.
L ₁ is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.
n1 is an integer from 0 to 2, and when n1 is 0, (L ₁ ) _n1 is a single bond. When a plurality of L _1s exist, each of the plurality of L _1s may be the same or different.
R ₁₁ and R ₁₂ are each independently a hydrogen atom or a substituent R. R ₁₁ and R ₁₂ do not bond to each other.
One or more of the groups consisting of two or more adjacent ones of R ₁₃ to R ₁₆ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or Does not form unsaturated rings.
The substituted or unsubstituted saturated or unsaturated ring-forming R ₁₃ to R ₁₆ are each independently a hydrogen atom or a substituent R.
X ₁ to X ₃ are each independently N or C(R ₂₁ ), and at least two of X ₁ to X ₃ are N. R ₂₁ is a hydrogen atom or a substituent R.
Ar ₂ and Ar ₃ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
L ₂ and L ₃ are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; It is.
n2 is an integer from 0 to 2, and when n2 is 0, (L ₂ ) _n2 is a single bond. When a plurality of L ₂ exists, each of the plurality of L ₂ may be the same or different.
n3 is an integer from 0 to 2, and when n3 is 0, (L ₃ ) _n3 is a single bond. When a plurality of L ₃ exists, each of the plurality of L ₃ may be the same or different.
The substituent R is
Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring 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 each independently,
hydrogen atom,
Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. When two or more R ₉₀₁ to R ₉₀₇ 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 a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more substituents R exist, the two or more substituents R may be the same or different. ]
2. a cathode;
an anode;
one or more organic layers disposed between the cathode and the anode;
has
At least one of the organic layers comprises 1. An organic electroluminescent device comprising the compound described in .
3.2. An electronic device comprising the organic electroluminescent element according to .

According to the present invention, a compound that can realize a higher performance organic EL element can be provided.

1 is a diagram showing a schematic configuration of an organic EL element according to one embodiment of the present invention.

[Definition]
In this specification, the hydrogen atom includes isotopes having different numbers of neutrons, ie, light hydrogen (protium), deuterium (deuterium), and tritium (tritium).

In this specification, in a chemical structural formula, a hydrogen atom, that is, a light hydrogen atom, a deuterium atom, or Assume that tritium atoms are bonded.

In this specification, the number of carbon atoms forming a ring refers to the number of carbon atoms constituting the ring itself of a compound having a structure in which atoms are bonded in a cyclic manner (for example, a monocyclic compound, a condensed ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound). represents the number of carbon atoms among the atoms. When the ring is substituted with a substituent, the carbon contained in the substituent is not included in the number of carbon atoms forming the ring. The "number of ring carbon atoms" described below is the same unless otherwise specified. For example, a benzene ring has 6 carbon atoms, a naphthalene ring has 10 carbon atoms, a pyridine ring has 5 carbon atoms, and a furan ring has 4 carbon atoms. Further, for example, the number of ring carbon atoms in the 9,9-diphenylfluorenyl group is 13, and the number of ring carbon atoms in the 9,9'-spirobifluorenyl group is 25.
Further, when the benzene ring is substituted with an alkyl group as a substituent, for example, the number of carbon atoms of the alkyl group is not included in the number of carbon atoms forming the benzene ring. Therefore, the number of ring carbon atoms in the benzene ring substituted with an alkyl group is 6. Further, when the naphthalene ring is substituted with an alkyl group as a substituent, for example, the number of carbon atoms of the alkyl group is not included in the number of carbon atoms forming the naphthalene ring. Therefore, the number of ring carbon atoms in the naphthalene ring substituted with an alkyl group is 10.

In this specification, the number of ring-forming atoms refers to compounds with a structure in which atoms are bonded in a cyclic manner (e.g., monocyclic, fused ring, and ring assembly) (e.g., monocyclic compound, fused ring compound, bridged compound, carbocyclic compound). Represents the number of atoms that constitute the ring itself (compounds and heterocyclic compounds). Atoms that do not form a ring (for example, a hydrogen atom that terminates a bond between atoms that form a ring) and atoms that are included in a substituent when the ring is substituted with a substituent are not included in the number of ring-forming atoms. The "number of ring-forming atoms" described below is the same unless otherwise specified. For example, the number of ring atoms in the pyridine ring is 6, the number of ring atoms in the quinazoline ring is 10, and the number of ring atoms in the furan ring is 5. For example, the number of hydrogen atoms bonded to the pyridine ring or atoms constituting substituents is not included in the number of atoms forming the pyridine ring. Therefore, the number of ring atoms of the pyridine ring to which hydrogen atoms or substituents are bonded is six. Furthermore, for example, hydrogen atoms bonded to carbon atoms of the quinazoline ring or atoms constituting substituents are not included in the number of ring-forming atoms of the quinazoline ring. Therefore, the number of ring atoms in the quinazoline ring to which hydrogen atoms or substituents are bonded is 10.

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

In this specification, "number of atoms XX to YY" in the expression "substituted or unsubstituted ZZ group with number of atoms XX to YY" represents the number of atoms when the ZZ group is unsubstituted, and is substituted. Do not include the number of atoms of substituents in 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 this specification, an unsubstituted ZZ group refers to a case where a "substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and a substituted ZZ group refers to a "substituted or unsubstituted ZZ group". represents the case where is a "substituted ZZ group".
In the present specification, "unsubstituted" in the case of "substituted or unsubstituted ZZ group" means that the hydrogen atom in the ZZ group is not replaced with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a light hydrogen atom, a deuterium atom, or a tritium atom.
Furthermore, in this specification, "substituted" in the case of "substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced with a substituent. "Substitution" in the case of "BB group substituted with an AA group" similarly means that one or more hydrogen atoms in the BB group are replaced with an AA group.

"Substituents described herein"
The substituents described in this specification will be explained below.

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

・“Substituted or unsubstituted aryl group”
Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in this specification include the following unsubstituted aryl groups (specific example group G1A) and substituted aryl groups (specific example group G1B). ) etc. (Here, the unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group", and the substituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is (Refers to the case where it is a "substituted aryl group.") In this specification, the mere mention of "aryl group" includes both "unsubstituted aryl group" and "substituted aryl group."
"Substituted aryl group" means a group in which one or more hydrogen atoms of "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" in the specific example group G1A below are replaced with a substituent, and a substituted aryl group in the following specific example group G1B. Examples include: The examples of "unsubstituted aryl group" and "substituted aryl group" listed here are just examples, and the "substituted aryl group" described in this specification includes the following specific examples. A group in which the hydrogen atom bonded to the carbon atom of the aryl group itself in the "substituted aryl group" of Group G1B is further replaced with a substituent, and a hydrogen atom of the substituent in the "substituted aryl group" in the following specific example group G1B is Furthermore, groups substituted with substituents are 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,
anthryl group,
benzanthryl group,
phenanthryl group,
benzophenanthryl group,
phenalenyl group,
pyrenyl group,
chrysenyl group,
benzocrysenyl group,
triphenylenyl group,
benzotriphenylenyl group,
tetracenyl group,
pentacenyl group,
fluorenyl group,
9,9'-spirobifluorenyl group,
benzofluorenyl group,
dibenzofluorenyl group,
fluoranthenyl group,
benzofluoranthenyl group,
A monovalent aryl group derived by removing one hydrogen atom from a perylenyl group and a 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,
para-xylyl group,
meta-xylyl group,
ortho-xylyl group,
para-isopropylphenyl group,
meta-isopropylphenyl group,
ortho-isopropylphenyl group,
para-t-butylphenyl group,
meta-t-butylphenyl group,
ortho-t-butylphenyl group,
3,4,5-trimethylphenyl group,
9,9-dimethylfluorenyl group,
9,9-diphenylfluorenyl group 9,9-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 group in which one or more hydrogen atoms of a monovalent group derived from a naphthylphenyl group and a ring structure represented by the above 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 as a ring-forming atom. Specific examples of heteroatoms include nitrogen atom, oxygen atom, sulfur atom, silicon atom, phosphorus atom, and boron atom.
A "heterocyclic group" as described herein is a monocyclic group or a fused ring group.
A "heterocyclic group" as described herein is an aromatic heterocyclic group or a non-aromatic heterocyclic group.
Specific examples of the "substituted or unsubstituted heterocyclic group" (specific example group G2) described in this specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group ( Examples include specific example group G2B). (Here, the term "unsubstituted heterocyclic group" refers to the case where "substituted or unsubstituted heterocyclic group" is "unsubstituted heterocyclic group", and the term "substituted heterocyclic group" refers to "substituted or unsubstituted heterocyclic group"). "Heterocyclic group" refers to a "substituted heterocyclic group.") In this specification, simply "heterocyclic group" refers to "unsubstituted heterocyclic group" and "substituted heterocyclic group." including both.
"Substituted heterocyclic group" means a group in which one or more hydrogen atoms of "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" in specific example group G2A is replaced, and examples of substituted heterocyclic groups in specific example group G2B below. Can be mentioned. The examples of "unsubstituted heterocyclic group" and "substituted heterocyclic group" listed here are just examples, and the "substituted heterocyclic group" described in this specification includes specific A group in which the hydrogen atom bonded to the ring-forming atom of the heterocyclic group itself in the "substituted heterocyclic group" in example group G2B is further replaced with a substituent, and a substituent in the "substituted heterocyclic group" in specific example group G2B Also included are groups in which a hydrogen atom is further replaced with a substituent.

Specific example group G2A includes, for example, the following unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1), unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2), and unsubstituted heterocyclic groups containing a sulfur atom. heterocyclic group (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).

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

・Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1):
pyrrolyl group,
imidazolyl group,
pyrazolyl group,
triazolyl group,
Tetrazolyl group,
oxazolyl group,
isoxazolyl group,
oxadiazolyl group,
thiazolyl group,
isothiazolyl group,
thiadiazolyl group,
pyridyl group,
pyridazinyl group,
pyrimidinyl group,
pyrazinyl group,
triazinyl group,
indolyl group,
isoindolyl group,
indolizinyl group,
quinolidinyl group,
quinolyl group,
isoquinolyl group,
cinnolyl group,
phthalazinyl group,
quinazolinyl group,
quinoxalinyl group,
benzimidazolyl group,
indazolyl group,
phenanthrolinyl group,
phenanthridinyl group,
acridinyl group,
phenazinyl group,
carbazolyl group,
benzocarbazolyl group,
morpholino group,
phenoxazinyl group,
phenothiazinyl group,
Azacarbazolyl group and diazacarbazolyl group.

・Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2):
frill group,
oxazolyl group,
isoxazolyl group,
oxadiazolyl group,
xanthenyl group,
benzofuranyl group,
isobenzofuranyl group,
dibenzofuranyl group,
naphthobenzofuranyl group,
benzoxazolyl group,
benzisoxazolyl group,
phenoxazinyl group,
morpholino group,
dinaphthofuranyl group,
azadibenzofuranyl group,
diazadibenzofuranyl group,
Azanaphthobenzofuranyl group, and diazanaphthobenzofuranyl group.

・Unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3):
thienyl group,
thiazolyl group,
isothiazolyl group,
thiadiazolyl group,
benzothiophenyl group (benzothienyl group),
Isobenzothiophenyl group (isobenzothienyl group),
dibenzothiophenyl group (dibenzothienyl group),
naphthobenzothiophenyl group (naphthobenzothienyl group),
benzothiazolyl group,
benzisothiazolyl group,
phenothiazinyl group,
dinaphthothiophenyl group (dinaphthothienyl group),
Azadibenzothiophenyl group (azadibenzothienyl group),
Diazadibenzothiophenyl group (diazadibenzothienyl group),
Azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

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

In the general formulas (TEMP-16) to (TEMP-33), X _A and Y _A are each independently an oxygen atom, a sulfur atom, NH, or CH ₂ . However, at least one of X _A and Y _A is an oxygen atom, a sulfur atom, or NH.
In the general formulas (TEMP-16) to (TEMP-33), when at least one of X _A and Y _A is NH or CH ₂ , in the general formulas (TEMP-16) to (TEMP-33), 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,
diphenylcarbazol-9-yl group,
phenylcarbazol-9-yl group,
methylbenzimidazolyl group,
ethylbenzimidazolyl group,
phenyltriazinyl group,
biphenylyltriazinyl group,
diphenyltriazinyl group,
phenylquinazolinyl group, and biphenylylquinazolinyl group.

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

・Substituted heterocyclic group containing a sulfur atom (specific example group G2B3):
phenyldibenzothiophenyl group,
methyldibenzothiophenyl group,
A t-butyldibenzothiophenyl group and a monovalent residue of 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) is replaced with a substituent (specific example group G2B4) ):

The above-mentioned "one or more hydrogen atoms of a monovalent heterocyclic group" refers to a hydrogen atom bonded to a ring-forming carbon atom of the monovalent heterocyclic group, and at least one of XA and YA is NH. It means one or more hydrogen atoms selected from the hydrogen atom bonded to the nitrogen atom in the case where XA and YA are CH2, 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 this specification include the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B). ). (Here, an unsubstituted alkyl group refers to a case where a "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and a substituted alkyl group refers to a case where a "substituted or unsubstituted alkyl group" is (This refers to the case where it is a "substituted alkyl group.") Hereinafter, when it is simply referred to as an "alkyl group," it includes both an "unsubstituted alkyl group" and a "substituted alkyl group."
"Substituted alkyl group" means a group in which one or more hydrogen atoms in "unsubstituted alkyl group" are replaced with a substituent. Specific examples of the "substituted alkyl group" include groups in which one or more hydrogen atoms in the "unsubstituted alkyl group" (specific example group G3A) below are replaced with a substituent, and substituted alkyl groups (specific examples Examples include group G3B). In this specification, the alkyl group in "unsubstituted alkyl group" means a chain alkyl group. Therefore, the "unsubstituted alkyl group" includes a linear "unsubstituted alkyl group" and a branched "unsubstituted alkyl group". The examples of "unsubstituted alkyl group" and "substituted alkyl group" listed here are just examples, and the "substituted alkyl group" described in this specification includes specific example group G3B. A group in which the hydrogen atom of the alkyl group itself in the "substituted alkyl group" in "Substituted alkyl group" is further replaced with a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkyl group" in 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.

・Substituted alkyl group (specific example group G3B):
heptafluoropropyl group (including isomers),
pentafluoroethyl group,
2,2,2-trifluoroethyl group and trifluoromethyl group.

・“Substituted or unsubstituted alkenyl group”
Specific examples of the "substituted or unsubstituted alkenyl group" (specific example group G4) described in this specification include the following unsubstituted alkenyl groups (specific example group G4A) and substituted alkenyl groups (specific example group G4B), etc. (Here, the term "unsubstituted alkenyl group" refers to the case where "substituted or unsubstituted alkenyl group" is "unsubstituted alkenyl group", and "substituted alkenyl group" refers to "substituted or unsubstituted alkenyl group"). " refers to the case where it is a "substituted alkenyl group.") In the present specification, simply "alkenyl group" includes both "unsubstituted alkenyl group" and "substituted alkenyl group."
"Substituted alkenyl group" means a group in which one or more hydrogen atoms in "unsubstituted alkenyl group" are replaced with a substituent. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl group" (specific example group G4A) having a substituent, and the substituted alkenyl group (specific example group G4B). It will be done. The examples of "unsubstituted alkenyl group" and "substituted alkenyl group" listed here are just examples, and the "substituted alkenyl group" described in this specification includes specific example group G4B. A group in which the hydrogen atom of the alkenyl group itself in the "substituted alkenyl group" is further replaced with a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkenyl group" in 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.

・Substituted alkenyl group (specific example group G4B):
1,3-butandienyl 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 of the "substituted or unsubstituted alkynyl group" (specific example group G5) described in this specification include the following unsubstituted alkynyl group (specific example group G5A). (Here, the term "unsubstituted alkynyl group" refers to the case where "substituted or unsubstituted alkynyl group" is "unsubstituted alkynyl group.") Hereinafter, when simply "alkynyl group" is used, "unsubstituted alkynyl group" is referred to as "unsubstituted alkynyl group." ``alkynyl group'' and ``substituted alkynyl group.''
"Substituted alkynyl group" means a group in which one or more hydrogen atoms in "unsubstituted alkynyl group" are replaced with a substituent. Specific examples of the "substituted alkynyl group" include groups in which one or more hydrogen atoms in the following "unsubstituted alkynyl group" (specific example group G5A) are replaced with a substituent.

・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 this specification include the following unsubstituted cycloalkyl groups (specific example group G6A) and substituted cycloalkyl groups ( Examples include specific example group G6B). (Here, the term "unsubstituted cycloalkyl group" refers to the case where "substituted or unsubstituted cycloalkyl group" is "unsubstituted cycloalkyl group", and the term "substituted cycloalkyl group" refers to "substituted or unsubstituted cycloalkyl group"). ("cycloalkyl group" refers to the case where "substituted cycloalkyl group" is used.) In this specification, when simply referring to "cycloalkyl group", it refers to "unsubstituted cycloalkyl group" and "substituted cycloalkyl group". including both.
"Substituted cycloalkyl group" means a group in which one or more hydrogen atoms in "unsubstituted cycloalkyl group" are replaced with a substituent. Specific examples of the "substituted cycloalkyl group" include the following "unsubstituted cycloalkyl group" (specific example group G6A) in which one or more hydrogen atoms are replaced with a substituent, and a substituted cycloalkyl group. (Specific example group G6B) and the like can be mentioned. The examples of "unsubstituted cycloalkyl group" and "substituted cycloalkyl group" listed here are just examples, and the "substituted cycloalkyl group" described in this specification includes specific A group in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself is replaced with a substituent in the "substituted cycloalkyl group" of example group G6B, and in the "substituted cycloalkyl group" of specific example group G6B Also included are groups in which the hydrogen atom of a substituent is further replaced with a substituent.

・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.

・Substituted cycloalkyl group (specific example group G6B):
4-methylcyclohexyl group.

・"Group represented by -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ )"
Specific examples of the group represented by -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ) described in this specification (specific example group G7) include:
-Si(G1)(G1)(G1),
-Si (G1) (G2) (G2),
-Si (G1) (G1) (G2),
-Si(G2)(G2)(G2),
-Si(G3)(G3)(G3), and -Si(G6)(G6)(G6)
can be mentioned. here,
G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2.
G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3.
G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
- A plurality of G1's in Si(G1) (G1) (G1) are the same or different from each other.
- A plurality of G2's in Si(G1)(G2)(G2) are mutually the same or different.
- A plurality of G1's in Si(G1) (G1) (G2) are mutually the same or different.
- A plurality of G2's in Si(G2) (G2) (G2) are mutually the same or different.
- A plurality of G3's in Si(G3) (G3) (G3) are mutually the same or different.
- A plurality of G6's in Si(G6) (G6) (G6) are mutually the same or different.

・"Group represented by -O-(R ₉₀₄ )"
Specific examples of the group represented by -O-(R ₉₀₄ ) described in this specification (specific example group G8) include:
-O(G1),
-O(G2),
-O (G3) and -O (G6)
can be mentioned.
here,
G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2.
G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3.
G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

・"Group represented by -S-(R ₉₀₅ )"
Specific examples of the group represented by -S-(R ₉₀₅ ) described in this specification (specific example group G9) include:
-S (G1),
-S (G2),
-S (G3) and -S (G6)
can be mentioned.
here,
G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2.
G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3.
G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.

・"Group represented by -N(R ₉₀₆ )(R ₉₀₇ )"
Specific examples of the group represented by -N(R ₉₀₆ )(R ₉₀₇ ) described in this specification (specific example group G10) include:
-N(G1)(G1),
-N(G2)(G2),
-N (G1) (G2),
-N (G3) (G3), and -N (G6) (G6)
can be mentioned.
here,
G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2.
G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3.
G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
-N(G1) A plurality of G1's in (G1) are mutually the same or different.
-N(G2) A plurality of G2's in (G2) are the same or different.
-N(G3) A plurality of G3's in (G3) are mutually the same or different.
-N(G6) Multiple G6s in (G6) are the same or different from each other

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

・“Substituted or unsubstituted fluoroalkyl group”
The "substituted or unsubstituted fluoroalkyl group" described in this specification refers to a "substituted or unsubstituted alkyl group" in which at least one hydrogen atom bonded to a carbon atom constituting the alkyl group is replaced with a fluorine atom. It also includes a group in which all hydrogen atoms bonded to the carbon atoms constituting the alkyl group in a "substituted or unsubstituted alkyl group" are replaced with fluorine atoms (perfluoro group). The number of carbon atoms in the "unsubstituted fluoroalkyl group" is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18, unless otherwise specified herein. "Substituted fluoroalkyl group" means a group in which one or more hydrogen atoms of the "fluoroalkyl group" are replaced with a substituent. In addition, the "substituted fluoroalkyl group" described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the "substituted fluoroalkyl group" is further replaced with a substituent, and Also included are groups in which one or more hydrogen atoms of a substituent in a "substituted fluoroalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted fluoroalkyl group" include 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”
The "substituted or unsubstituted haloalkyl group" described herein means that 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 also includes a group in which all hydrogen atoms bonded to carbon atoms constituting an alkyl group in a "substituted or unsubstituted alkyl group" are replaced with halogen atoms. Unless otherwise specified herein, the number of carbon atoms in the "unsubstituted haloalkyl group" is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18. "Substituted haloalkyl group" means a group in which one or more hydrogen atoms of the "haloalkyl group" are replaced with a substituent. In addition, the "substituted haloalkyl group" described in this specification includes a group in which one or more hydrogen atoms bonded to the carbon atom of the alkyl chain in the "substituted haloalkyl group" is further replaced with a substituent; Also included are groups in which one or more hydrogen atoms of a substituent in the "haloalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted haloalkyl group" include a group in which one or more hydrogen atoms in the "alkyl group" (specific example group G3) are replaced with a halogen atom. A haloalkyl group is sometimes referred to as a halogenated alkyl group.

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

・“Substituted or unsubstituted alkylthio group”
A specific example of the "substituted or unsubstituted alkylthio group" described in this specification is a group represented by -S(G3), where G3 is the "substituted or unsubstituted alkylthio group" described in specific example group G3. "unsubstituted alkyl group". Unless otherwise specified herein, the number of carbon atoms in the "unsubstituted alkylthio group" is from 1 to 50, preferably from 1 to 30, and more preferably from 1 to 18.

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

・“Substituted or unsubstituted arylthio group”
A specific example of the "substituted or unsubstituted arylthio group" described in this specification is a group represented by -S(G1), where G1 is the "substituted or unsubstituted arylthio group" described in the specific example group G1. "Unsubstituted aryl group". The number of ring carbon atoms in the "unsubstituted arylthio group" is from 6 to 50, preferably from 6 to 30, and more preferably from 6 to 18, unless otherwise specified herein.

・“Substituted or unsubstituted trialkylsilyl group”
A specific example of the "trialkylsilyl group" described in this specification is a group represented by -Si(G3)(G3)(G3), where G3 is a group described in specific example group G3. It is a "substituted or unsubstituted alkyl group." - A plurality of G3's in Si(G3) (G3) (G3) are mutually the same or different. The number of carbon atoms in each alkyl group of the "trialkylsilyl group" is from 1 to 50, preferably from 1 to 20, and more preferably from 1 to 6, unless otherwise specified herein.

・“Substituted or unsubstituted aralkyl group”
A specific example of the "substituted or unsubstituted aralkyl group" described in this specification is a group represented by -(G3)-(G1), where G3 is a group described in 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, an "aralkyl group" is a group in which the hydrogen atom of an "alkyl group" is replaced with an "aryl group" as a substituent, and is one embodiment of a "substituted alkyl group." An "unsubstituted aralkyl group" is an "unsubstituted alkyl group" substituted with an "unsubstituted aryl group", and the number of carbon atoms in the "unsubstituted aralkyl group" is determined unless otherwise specified herein. , 7 to 50, preferably 7 to 30, more preferably 7 to 18.
Specific examples of "substituted or unsubstituted aralkyl groups" include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α - Naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β-naphthylethyl group , 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, and 2-β-naphthylisopropyl group.

The substituted or unsubstituted aryl group described herein is preferably a phenyl group, p-biphenyl group, m-biphenyl group, o-biphenyl group, p-terphenyl group, unless otherwise specified herein. 4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl- 2-yl group, o-terphenyl-4-yl group, o-terphenyl-3-yl group, o-terphenyl-2-yl group, 1-naphthyl group, 2-naphthyl group, anthryl group, phenanthryl group , pyrenyl group, chrysenyl group, triphenylenyl group, fluorenyl group, 9,9'-spirobifluorenyl group, 9,9-dimethylfluorenyl group, and 9,9-diphenylfluorenyl group.

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 benzimidazolyl group, or a phenol group, unless otherwise specified herein. Nanthrolinyl 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)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazole -4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyl group These include riazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group.

In this specification, the carbazolyl group is specifically any of the following groups unless otherwise specified in this specification.

In this specification, the (9-phenyl)carbazolyl group is specifically any of the following groups, unless otherwise specified in the specification.

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

In this specification, the dibenzofuranyl group and dibenzothiophenyl group are specifically any of the following groups, unless otherwise specified in the specification.

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

Unless otherwise specified herein, the substituted or unsubstituted alkyl group described herein is preferably a methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, isobutyl group, and t- Butyl group, etc.

・“Substituted or unsubstituted arylene group”
Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification refers to 2 derived from the above "substituted or unsubstituted aryl group" by removing one hydrogen atom on the aryl ring. It is the basis of valence. As a specific example of the "substituted or unsubstituted arylene group" (specific example group G12), by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in specific example group G1, Examples include divalent groups derived from the derivatives.

・“Substituted or unsubstituted divalent heterocyclic group”
Unless otherwise specified, the "substituted or unsubstituted divalent heterocyclic group" described herein refers to the "substituted or unsubstituted heterocyclic group" described above, in which one hydrogen atom on the heterocycle is removed. It is a divalent group derived from Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include one hydrogen on the heterocycle from the "substituted or unsubstituted heterocyclic group" described in specific example group G2. Examples include divalent groups derived by removing atoms.

・“Substituted or unsubstituted alkylene group”
Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification refers to 2 derived from the above "substituted or unsubstituted alkyl group" by removing one hydrogen atom on the alkyl chain. It is the basis of valence. As a specific example of a "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 specific example group G3. Examples include divalent groups derived from the derivatives.

The substituted or unsubstituted arylene group described herein is preferably a group represented by any of the following general formulas (TEMP-42) to (TEMP-68), unless otherwise specified herein.

In the general formulas (TEMP-42) to (TEMP-52), Q ₁ to Q ₁₀ are each independently a hydrogen atom or a substituent.
In the general formulas (TEMP-42) to (TEMP-52), * represents a binding site.

In the general formulas (TEMP-53) to (TEMP-62), Q ₁ to Q ₁₀ are each independently a hydrogen atom or a substituent.
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), Q ₁ to Q ₈ are each independently a hydrogen atom or a substituent.
In the general formulas (TEMP-63) to (TEMP-68), * represents a binding site.

The substituted or unsubstituted divalent heterocyclic group described herein is preferably one of the following general formulas (TEMP-69) to (TEMP-102), unless otherwise specified herein. It is.

In the general formulas (TEMP-69) to (TEMP-82), Q ₁ to Q ₉ are each independently a hydrogen atom or a substituent.

In the general formulas (TEMP-83) to (TEMP-102), Q ₁ to Q ₈ are each independently a hydrogen atom or a substituent.

The above is the explanation about the "substituents described in this specification."

・"When combining to form a ring"
In the present specification, "one or more pairs of two or more adjacent groups are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring." or do not bond to each other'' means ``one or more pairs of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle''; One or more pairs of two or more adjacent groups bond to each other to form a substituted or unsubstituted condensed ring, and one or more pairs of two or more adjacent groups do not bond to each other. ” means if and.
In this specification, when "one or more sets of two or more adjacent rings are bonded to each other to form a substituted or unsubstituted monocycle" and "one or more sets of two or more adjacent rings are combined with each other to form a substituted or unsubstituted monocycle" Regarding the case where "a pair or more are combined with each other to form a substituted or unsubstituted condensed ring" (hereinafter, these cases may be collectively referred to as "a case where they are combined to form a ring"), the following ,explain. The case of an anthracene compound represented by the following general formula (TEMP-103) whose parent skeleton is an anthracene ring will be explained as an example.

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

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

The case where "a set of two or more adjacent items" forms a ring is not only the case where a set of "two" adjacent items are combined as in the example above, but also the case where a set of "three or more adjacent items" form a ring. This also includes the case where two sets are combined. For example, R ₉₂₁ and R ₉₂₂ combine with each other to form a ring Q _A , R ₉₂₂ and R ₉₂₃ combine with each other to form a ring Q _C , and the three adjacent to each other (R ₉₂₁ , R ₉₂₂ and R ₉₂₃ ) combine with each other to form a ring and are condensed to the anthracene mother skeleton. In this case, the anthracene compound represented by the general formula (TEMP-103) is as follows: 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 "single ring" or "fused ring" that is formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even if "one set of two adjacent rings" forms a "monocycle" or "fused ring," the "monocycle" or "fused ring" is a saturated ring, or Can form unsaturated rings. For example, ring Q _A and ring Q _B formed in the general formula (TEMP-104) are each a "monocyclic ring" or a "fused ring." Furthermore, the ring Q _A and the ring Q _C formed in the general formula (TEMP-105) are "fused rings". Ring Q _A and ring Q _C in the general formula (TEMP-105) are a condensed ring due to the condensation of ring Q _A and ring Q _C. When ring Q _A in the general formula (TMEP-104) is a benzene ring, ring Q _A is a monocyclic ring. When ring Q _A in the general formula (TMEP-104) is a naphthalene ring, ring Q _A is a fused ring.

"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 triple bond in the ring structure (e.g., cyclohexene, cyclohexadiene, etc.), and non-aromatic heterocycles having unsaturated bonds (for example, dihydropyran, imidazoline, pyrazoline, quinolidine, indoline, isoindoline, 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 structures in which the groups listed as specific examples in specific example group G1 are terminated with hydrogen atoms.
Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic group listed as a specific example in specific example group G2 is terminated with a hydrogen atom.
Specific examples of the aliphatic hydrocarbon ring include structures in which the groups listed as specific examples in specific example group G6 are terminated with hydrogen atoms.
"Form a ring" means to form a ring with only a plurality of atoms of the parent skeleton, or with a plurality of atoms of the parent skeleton and one or more arbitrary atoms. For example, the ring Q _A shown in the general formula (TEMP-104) formed by R ₉₂₁ and R ₉₂₂ bonding to each other is a carbon atom of the anthracene skeleton to which R ₉₂₁ is bonded, and an anthracene bond to which R ₉₂₂ is bonded. It means a ring formed by a carbon atom of the skeleton and one or more arbitrary atoms. As a specific example, when R ₉₂₁ and R ₉₂₂ form a ring Q _A , the carbon atom of the anthracene skeleton to which R ₉₂₁ is bonded, the carbon atom of the anthracene skeleton to which R ₉₂₂ is bonded, and four carbon atoms. When R 921 and R 922 form a monocyclic unsaturated ring, the ring formed by R ₉₂₁ and R ₉₂₂ is a benzene ring.

Here, unless otherwise specified herein, "any atom" is preferably at least one atom selected from the group consisting of carbon atom, nitrogen atom, oxygen atom, and sulfur atom. In any atom (for example, in the case of a carbon atom or a nitrogen atom), a 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 below. When it contains any atoms other than carbon atoms, the ring formed is a heterocycle.
Unless otherwise specified herein, "one or more arbitrary atoms" constituting a monocyclic ring or a condensed ring are preferably 2 to 15 atoms, more preferably 3 to 12 atoms. , more preferably 3 or more and 5 or less.
Unless otherwise specified herein, "monocycle" is preferred among "monocycle" and "fused ring."
Unless otherwise specified herein, the "unsaturated ring" is preferred between the "saturated ring" and the "unsaturated ring".
Unless otherwise stated herein, a "monocycle" is preferably a benzene ring.
Unless otherwise stated herein, an "unsaturated ring" is preferably a benzene ring.
When "one or more pairs of two or more adjacent groups" are "bonded with each other to form a substituted or unsubstituted monocycle" or "bonded with each other to form a substituted or unsubstituted fused ring" In the case of "forming", unless otherwise specified herein, preferably, one or more of the pairs of two or more adjacent atoms are bonded to each other to form a bond with a plurality of atoms of the parent skeleton and one or more of the 15 or more atoms. A substituted or unsubstituted "unsaturated ring" is formed with at least one atom selected from the group consisting of carbon atoms, nitrogen atoms, oxygen atoms, and sulfur atoms.

When the above-mentioned "single ring" or "fused ring" has a substituent, the substituent is, for example, the "arbitrary substituent" described below. Specific examples of the substituent in the case where the above-mentioned "single ring" or "fused ring" has a substituent are the substituents described in the section of "Substituent described herein" above.
When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "arbitrary substituent" described below. Specific examples of the substituent in the case where the above-mentioned "single ring" or "fused ring" has a substituent are the substituents described in the section of "Substituent described herein" above.
The above applies to cases in which "one or more sets of two or more adjacent groups combine with each other to form a substituted or unsubstituted monocycle" and "one or more sets of two or more adjacent groups" are combined with each other to form a substituted or unsubstituted condensed ring ("the case where they are combined to form a ring").

・Substituent in the case of "substituted or unsubstituted" In one embodiment in this specification, the substituent in the case of "substituted or unsubstituted" (herein referred to as "arbitrary substituent") For example,
unsubstituted alkyl group having 1 to 50 carbon atoms,
unsubstituted alkenyl group having 2 to 50 carbon atoms,
unsubstituted alkynyl group having 2 to 50 carbon atoms,
an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),
-O-(R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N(R ₉₀₆ )(R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
A group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring carbon atoms, and an unsubstituted heterocyclic group having 5 to 50 ring atoms,
Here, R ₉₀₁ to R ₉₀₇ are each independently,
hydrogen atom,
Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
When two or more R _901s exist, the two or more R _901s are the same or different,
When two or more R _902s exist, the two or more R _902s are the same or different,
When two or more R _903s exist, the two or more R _903s are the same or different,
When two or more R _904s exist, the two or more R _904s are the same or different,
When two or more R _905s exist, the two or more R _905s are the same or different,
When two or more R _906s exist, the two or more R _906s are the same or different,
When two or more R _907s exist, the two or more R _907s are the same or different.

In one embodiment, the substituent in the case of "substituted or unsubstituted" is
an alkyl group having 1 to 50 carbon atoms,
A group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a heterocyclic group having 5 to 50 ring atoms.

In one embodiment, the substituent in the case of "substituted or unsubstituted" is
an alkyl group having 1 to 18 carbon atoms,
A group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a heterocyclic group having 5 to 18 ring atoms.

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

Unless otherwise specified in this specification, any adjacent substituents may form a "saturated ring" or "unsaturated ring", preferably a substituted or unsubstituted saturated ring. 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 specified herein, any substituent may further have a substituent. The substituents that the arbitrary substituents further have are the same as the above arbitrary substituents.

In this specification, the numerical range expressed using "AA-BB" has the numerical value AA written before "AA-BB" as the lower limit, and the numerical value BB written after "AA-BB". means a range that includes as an upper limit value.

［式（１）中、
ＹはＯ又はＳである。
Ｒ_１～Ｒ_４のうちいずれか１つはＬ_１との結合を表す。Ｌ_１との結合を表さないＲ_１～Ｒ_４の少なくとも１つはＡｒ_１である。
Ａｒ_１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環形成炭素数６～１０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。ただし、前記環形成炭素数６～１０のアリール基における「置換もしくは無置換の」という場合の置換基はアリール基ではない。Ａｒ_１が２以上存在する場合、２以上のＡｒ_１のそれぞれは同一でもよく、異なってもよい。
Ｌ_１との結合を表さず、かつ、Ａｒ_１でもないＲ_１～Ｒ_４は、それぞれ独立に、水素原子又は置換基Ｒである。Ｌ_１との結合を表さないＲ_１～Ｒ_４のうち隣接する２つ以上からなる組は互いに結合しない。
Ｒ_５～Ｒ_８のうち隣接する２つ以上からなる組の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_５～Ｒ_８は、それぞれ独立に、水素原子又は置換基Ｒである。
Ｌ_１は、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。
ｎ１は０～２の整数であり、ｎ１が０である場合、（Ｌ_１）_ｎ１は単結合である。Ｌ_１が複数存在する場合、複数のＬ_１のそれぞれは同一でもよく、異なってもよい。
Ｒ_１１及びＲ_１２は、それぞれ独立に、水素原子又は置換基Ｒである。Ｒ_１１及びＲ_１２は互いに結合しない。
Ｒ_１３～Ｒ_１６のうち隣接する２つ以上からなる組の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_１３～Ｒ_１６は、それぞれ独立に、水素原子又は置換基Ｒである。
Ｘ_１～Ｘ_３は、それぞれ独立に、Ｎ又はＣ（Ｒ_２１）であり、Ｘ_１～Ｘ_３のうち少なくとも２つはＮである。Ｒ_２１は、水素原子又は置換基Ｒである。
Ａｒ_２及びＡｒ_３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_２及びＬ_３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。
ｎ２は０～２の整数であり、ｎ２が０である場合、（Ｌ_２）_ｎ２は単結合である。Ｌ_２が複数存在する場合、複数のＬ_２のそれぞれは同一でもよく、異なってもよい。
ｎ３は０～２の整数であり、ｎ３が０である場合、（Ｌ_３）_ｎ３は単結合である。Ｌ_３が複数存在する場合、複数のＬ_３のそれぞれは同一でもよく、異なってもよい。
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）
（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、異なってもよい。）、
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、及び
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
からなる群から選択される。
置換基Ｒが２以上存在する場合、２以上の置換基Ｒは同一でもよく、異なってもよい。］ [New compound]
A compound according to one embodiment of the present invention is represented by the following formula (1).

[In formula (1),
Y is O or S.
Any one of R ₁ to R ₄ represents a bond with L ₁ . At least one of R ₁ to R ₄ that does not represent a bond with L ₁ is Ar ₁ .
Ar ₁ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 ring atoms, or a substituted or unsubstituted monovalent group having 5 to 50 ring atoms; is a heterocyclic group. However, in the above-mentioned aryl group having 6 to 10 ring carbon atoms, the substituent in the term "substituted or unsubstituted" is not an aryl group. When two or more Ar ₁ 's exist, each of the two or more Ar ₁ 's may be the same or different.
R ₁ to R ₄ that do not represent a bond with L ₁ and are not Ar ₁ are each independently a hydrogen atom or a substituent R. A set of two or more adjacent ones of R ₁ to R ₄ that do not represent a bond with L ₁ does not bond to each other.
One or more of the groups consisting of two or more adjacent ones of R ₅ to R ₈ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or Does not form unsaturated rings.
The substituted or unsubstituted saturated or unsaturated ring-forming R ₅ to R ₈ are each independently a hydrogen atom or a substituent R.
L ₁ is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.
n1 is an integer from 0 to 2, and when n1 is 0, (L ₁ ) _n1 is a single bond. When a plurality of L _1s exist, each of the plurality of L _1s may be the same or different.
R ₁₁ and R ₁₂ are each independently a hydrogen atom or a substituent R. R ₁₁ and R ₁₂ do not bond to each other.
One or more of the groups consisting of two or more adjacent ones of R ₁₃ to R ₁₆ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or Does not form unsaturated rings.
The substituted or unsubstituted saturated or unsaturated ring-forming R ₁₃ to R ₁₆ are each independently a hydrogen atom or a substituent R.
X ₁ to X ₃ are each independently N or C(R ₂₁ ), and at least two of X ₁ to X ₃ are N. R ₂₁ is a hydrogen atom or a substituent R.
Ar ₂ and Ar ₃ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
L ₂ and L ₃ are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; It is.
n2 is an integer from 0 to 2, and when n2 is 0, (L ₂ ) _n2 is a single bond. When a plurality of L ₂ exists, each of the plurality of L ₂ may be the same or different.
n3 is an integer from 0 to 2, and when n3 is 0, (L ₃ ) _n3 is a single bond. When a plurality of L ₃ exists, each of the plurality of L ₃ may be the same or different.
The substituent R is
Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),
-O-(R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N(R ₉₀₆ )(R ₉₀₇ )
(R ₉₀₁ to R ₉₀₇ are each independently,
hydrogen atom,
Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. When two or more R ₉₀₁ to R ₉₀₇ 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 a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more substituents R exist, the two or more substituents R may be the same or different. ]

Since the compound according to one embodiment of the present invention has the above structure, when used in an organic EL device, the device performance can be improved. As one of the specific effects, it is possible to realize an organic EL element with low driving voltage and high efficiency.

All of the hydrogen atoms contained in the compound represented by formula (1) may be light hydrogen atoms, or some or all of them may be deuterium atoms.

In one embodiment, Y is an O atom.

Any one of R ₁ to R ₄ represents a bond with L ₁ . "Representing a bond" means that L ₁ is directly bonded to any carbon atom on the condensed ring structure to which R ₁ to R ₄ are bonded. When n1 is 0, the carbon atom on the condensed ring structure to which (L ₁ ) _n1 is bonded (on the right side of the paper) and any of the carbon atoms on the condensed ring structure to which R ₁ to R ₄ are bonded are monomers. Connect directly with a join.
In one embodiment R ₁ , R ₂ or R ₄ represents a bond with L ₁ .
In one embodiment R ₂ represents a bond with L ₁ .

At least one of R ₁ to R ₄ that does not represent a bond with L ₁ is Ar ₁ .
In one embodiment, R ₄ is Ar ₁ .

In one embodiment, R ₂ represents a bond with L ₁ and R ₄ is Ar ₁ .

Ar ₁ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 ring atoms, or a substituted or unsubstituted monovalent group having 5 to 50 ring atoms; is a heterocyclic group. However, the substituent in the case of "substituted or unsubstituted" in an aryl group having 6 to 10 ring carbon atoms is not an aryl group.
Substituents in the case of "substituted or unsubstituted" in substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms and substituted or unsubstituted monovalent heterocyclic groups having 5 to 50 ring atoms are particularly The groups described as "substituent R" can be used without limitation.

In the case of "substituted or unsubstituted" in the aryl group having 6 to 10 ring carbon atoms, substituents include "substituted or unsubstituted ring carbon atoms 6 to 10" among the groups explained as "substituent R". Examples include groups other than "50 aryl groups". In one embodiment, the substituent in the case of "substituted or unsubstituted" in the aryl group having 6 to 10 ring carbon atoms is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted ring A cycloalkyl group having 3 to 50 carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

In one embodiment, Ar ₁ is a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms, such as a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group.
In one embodiment, Ar ₁ is an unsubstituted aryl group having 6 to 10 ring carbon atoms, such as an unsubstituted phenyl group or an unsubstituted naphthyl group.
In one embodiment, Ar ₁ is an aryl group having 6 to 10 ring carbon atoms in which some or all of the hydrogen atoms are deuterium atoms, such as phenyl group in which some or all of the hydrogen atoms are deuterium atoms. group, or a naphthyl group in which some or all of the hydrogen atoms are deuterium atoms.
In one embodiment, Ar ₁ is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
In one embodiment, Ar ₁ is an unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.

In one embodiment, adjacent sets of two or more of R ₅ to R ₈ are not bonded to each other.
In one embodiment, R ₅ -R ₈ are hydrogen atoms.

In one embodiment, one or more pairs of two or more adjacent ones of R ₅ to R ₈ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring. For example, one or two of the groups R ₅ and R ₆ , R ₆ and R ₇ , and R ₇ and R ₈ combine with each other to form a substituted or unsubstituted benzene ring structure.

In one embodiment, L ₁ is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, such as a substituted or unsubstituted phenylene group.
In one embodiment, n1 is 0 or 1. In one embodiment, n1 is 0.

In one embodiment, adjacent sets of two or more of R ₁₃ to R ₁₆ are not bonded to each other.
In one embodiment, R ₁₁ to R ₁₆ are hydrogen atoms.

In one embodiment, three of X ₁ -X ₃ are N.
In one embodiment, two of X ₁ -X ₃ are N.
In one embodiment, X ₁ and X ₃ are N and X ₂ is C(R ₂₁ ).

In one embodiment, Ar ₂ and Ar ₃ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms.
In one embodiment, Ar ₂ and Ar ₃ are each independently an unsubstituted aryl group having 6 to 50 ring carbon atoms.
In one embodiment, Ar ₂ and Ar ₃ are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted fluorenyl group. .
In one embodiment, Ar ₂ and Ar ₃ are each independently an unsubstituted phenyl group, an unsubstituted naphthyl group, an unsubstituted biphenyl group, a fluorenyl group substituted with an alkyl group having 1 to 30 carbon atoms, or It is an unsubstituted fluorenyl group.
In one embodiment, Ar ₂ and Ar ₃ are each independently an aryl group having 6 to 10 ring carbon atoms in which some or all of the hydrogen atoms are deuterium atoms, for example, some or all of the hydrogen atoms are deuterium atoms. is a phenyl group in which is a deuterium atom, or a naphthyl group in which some or all of the hydrogen atoms are deuterium atoms.

In one embodiment, L ₂ and L ₃ are each independently a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, such as a substituted or unsubstituted phenylene group.
In one embodiment, n2 and n3 are each independently 0 or 1. In one embodiment, n2 and n3 are zero.

（式（１１）中、Ｒ_１～Ｒ_８、Ｒ_１１～Ｒ_１６、Ｘ_１～Ｘ_３、Ａｒ_２及びＡｒ_３は、前記式（１）で定義した通りである。なお、Ｒ_１～Ｒ_４のうちいずれか１つは＊との結合を表す。） In one embodiment, the compound represented by formula (1) is a compound represented by formula (11) below.

(In formula (11), R ₁ to R ₈ , R ₁₁ to R ₁₆ , X ₁ to X ₃ , Ar ₂ and Ar ₃ are as defined in formula (1) above. Note that R ₁ to R Any one of ₄ represents a combination with *.)

（式（１２）中、Ｒ_１～Ｒ_４、Ｘ_１～Ｘ_３、Ａｒ_２及びＡｒ_３は、前記式（１）で定義した通りである。なお、Ｒ_１～Ｒ_４のうちいずれか１つは＊との結合を表す。） In one embodiment, the compound represented by formula (1) is a compound represented by formula (12) below.

(In formula (12), R ₁ to R ₄ , X ₁ to X ₃ , Ar ₂ and Ar ₃ are as defined in formula (1) above. Note that any one of R ₁ to R ₄ (T represents the combination with *.)

（式（１３）中、Ｒ_１～Ｒ_４、Ａｒ_２及びＡｒ_３は、前記式（１）で定義した通りである。なお、Ｒ_１～Ｒ_４のうちいずれか１つは＊との結合を表す。） In one embodiment, the compound represented by formula (1) is a compound represented by formula (13) below.

(In formula (13), R ₁ to R ₄ , Ar ₂ and Ar ₃ are as defined in formula (1) above. Any one of R ₁ to R ₄ is a bond with * )

In one embodiment, the substituent in the case of "substituted or unsubstituted" in the compound represented by formula (1) and the substituent R are:
an alkyl group having 1 to 50 carbon atoms,
A group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a monovalent heterocyclic group having 5 to 50 ring atoms.
However, as described above, when Ar ₁ is a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms, the substituent used in "substituted or unsubstituted" is not an aryl group.

In one embodiment, the substituent in the case of "substituted or unsubstituted" in the compound represented by formula (1) and the substituent R are:
an alkyl group having 1 to 18 carbon atoms,
A group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a monovalent heterocyclic group having 5 to 18 ring atoms.
However, as described above, when Ar ₁ is a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms, the substituent used in "substituted or unsubstituted" is not an aryl group.

Specific examples of the compound represented by formula (1) are described below, but these are merely illustrative, and the compound represented by formula (1) is not limited to the following specific examples.

[Materials for organic electroluminescent devices]
The compound according to one embodiment of the present invention (the compound represented by formula (1) above) is useful as a material for an organic EL device, for example, as a material for an electron transport band of an organic EL device.

[Organic EL element]
An organic EL element according to one embodiment of the present invention will be described.
An organic EL element according to one aspect of the present invention includes a cathode, an anode, and one or more organic layers disposed between the cathode and the anode, and at least one of the organic layers. One layer contains a compound according to one aspect of the invention.

The organic EL device according to one embodiment of the present invention preferably includes an anode, a light-emitting layer, an electron transport zone, and a cathode in this order, and the electron transport zone contains the compound according to one embodiment of the present invention.

A typical element configuration of the organic EL element is a structure in which structures such as the following (1) to (4) are laminated on a substrate.
(1) Anode/Emissive layer/Cathode (2) Anode/Hole transport zone/Emissive layer/Cathode (3) Anode/Emissive layer/Electron transport zone/Cathode (4) Anode/Hole transport zone/Emissive layer/Electron Transport zone/cathode (“/” indicates that each layer is stacked adjacent to each other.)

The electron transport zone usually consists of one or more layers selected from an electron injection layer and an electron transport layer. The hole transport zone usually consists of one or more layers selected from a hole injection layer and a hole transport layer.

A schematic structure of an organic EL element according to one embodiment of the present invention will be described with reference to FIG.
An organic EL device 1 according to one embodiment of the present invention includes a substrate 2, an anode 3, a light emitting layer 5, a cathode 10, a hole transport zone 4 between the anode 3 and the light emitting layer 5, and a light emitting layer. 5 and an electron transport zone 6 between the cathode 10 and the cathode 10.

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

(substrate)
The substrate is used as a support for the light emitting device. As the substrate, for example, glass, quartz, plastic, etc. can be used. Alternatively, a flexible substrate may be used. The flexible substrate refers to a bendable (flexible) substrate, and includes, for example, a plastic substrate made of polycarbonate or polyvinyl chloride.

(anode)
For the anode formed on the substrate, it is preferable to use a metal, an alloy, an electrically conductive compound, a mixture thereof, or the like having a large work function (specifically, 4.0 eV or more). Specifically, for example, indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, indium oxide containing zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), and nitrides of metal materials (eg, titanium nitride).

(hole injection layer)
The hole injection layer is a layer containing a substance with high hole injection properties. Substances with high hole injection properties include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, Tungsten oxide, manganese oxide, aromatic amine compounds, or high molecular compounds (oligomers, dendrimers, polymers, etc.) can also be used.

(hole transport layer)
The hole transport layer is a layer containing a substance with high hole transport properties. For the hole transport layer, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used. Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used. However, materials other than these may be used as long as they have a higher transportability for holes than for electrons. Note that the layer containing a substance with high hole transport properties is not limited to a single layer, and may be a stack of two or more layers made of the above substance.

(Guest (dopant) material of light emitting layer)
The light-emitting layer is a layer containing a highly luminescent substance, and various materials can be used for the light-emitting layer. For example, as a highly luminescent substance, 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 material that can be used in the light emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. can be used. As a green fluorescent material that can be used in the light emitting layer, aromatic amine derivatives and the like can be used. Tetracene derivatives, diamine derivatives, etc. can be used as red fluorescent materials that can be used in the light emitting layer.
Metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used as blue-based phosphorescent materials that can be used in the light-emitting layer. An iridium complex or the like is used as a green phosphorescent material that can be used in the light emitting layer. Metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used as red-colored phosphorescent materials that can be used in the light-emitting layer.

(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). Various substances can be used to disperse highly luminescent substances, and the lowest unoccupied orbital level (LUMO level) is higher than that of highly luminescent substances, and the highest occupied orbital level (LUMO level) is higher than that of highly luminescent substances. It is preferable to use a substance with a low HOMO level.
Substances (host materials) for dispersing highly luminescent substances include 1) metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes, 2) oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives. Heterocyclic compounds, 3) fused aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives, 4) aromatic amine compounds such as triarylamine derivatives, or fused polycyclic aromatic amine derivatives. used.

(electron transport layer)
The electron transport layer is a layer containing a substance with high electron transport properties. The electron transport layer contains 1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes, 2) heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives, and 3) polymer compounds. can be used.

In one embodiment of the present invention, the electron transport layer may or may not contain the other substances described above in addition to the compound represented by formula (1) above.

(electron injection layer)
The electron injection layer is a layer containing a substance with high electron injection properties. The electron injection layer contains lithium (Li), ytterbium (Yb), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), 8-hydroxyquinolinolato-lithium (Liq), etc. metal complex compounds, alkali metals such as lithium oxide (LiO _x ), alkaline earth metals, or compounds thereof can be used.

In the organic EL device according to one embodiment of the present invention, an electron transport band is formed between a first layer (also referred to as a "first electron transport layer" or a "hole blocking layer") and a second layer from the light emitting layer side. (also referred to as "second electron transport layer") in this order, the first layer contains the compound represented by formula (1), and another layer is provided between the light emitting layer and the first layer. Contains no layers.
Further, as the second layer, one or more selected from the configurations explained in the above-mentioned electron transport layer and electron injection layer can be applied, for example, a combination of an azine derivative and a metal complex compound such as Liq. It may also be a layer made of mixed materials.
In one embodiment, the first layer consists only of the compound represented by the above formula (1), or substantially consists of only the compound represented by the above formula (1). In the latter case, it may contain unavoidable impurities. In one embodiment, the first layer is 90% by weight or more, 95% by weight or more, 99% by weight or more, 99.5% by weight or more, 99.9% by weight or more, 99.99% by weight or more, or 100% by weight. is a compound represented by the above formula (1).

(cathode)
For the cathode, it is preferable to use metals, alloys, electrically conductive compounds, mixtures thereof, etc. with a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg) and calcium ( Examples include alkaline earth metals such as Ca), strontium (Sr), alloys containing these (for example, MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.
The cathode is usually formed by vacuum evaporation or sputtering. Moreover, when using silver paste etc., a coating method, an inkjet method, etc. can be used.

In addition, when an electron injection layer is provided, the cathode can be formed using various conductive materials such as aluminum, silver, ITO, graphene, silicon, or indium oxide-tin oxide containing silicon oxide, regardless of the size of the work function. can be formed.

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

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

[Electronics]
An electronic device according to one embodiment of the present invention includes an organic EL element according to one embodiment 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, or personal computers, and light emitting devices such as lighting or vehicle lamps.

化合物１ <Compound>
The compound represented by formula (1) used for manufacturing the organic EL device of Example 1 is shown below.

Compound 1

化合物Ｒｅｆ The structure of the compound used to manufacture the organic EL device of Comparative Example 1 is shown below.

Compound Ref

The structures of other compounds used in manufacturing the organic EL devices of Example 1 and Comparative Example 1 are shown below.

Example 1
<Production of organic EL element>
An organic EL device was produced as follows.
A 25 mm x 75 mm x 1.1 mm thick glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatic Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.
The cleaned glass substrate with a transparent electrode is mounted on the substrate holder of a vacuum evaporation device, and first, compounds HT-1 and HI-1 are added to the surface on which the transparent electrode is formed so as to cover the transparent electrode. A first hole transport layer having a thickness of 10 nm was formed by co-evaporation so that the proportion of -1 was 3% by mass.
Compound HT-1 was deposited on the first hole transport layer to form a second hole transport layer with a thickness of 80 nm.
Compound EBL-1 was deposited on the second hole transport layer to form a third hole transport layer with a thickness of 5 nm.
Compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated on the third hole transport layer so that the proportion of compound BD-1 was 4% by mass, and a film with a thickness of 25 nm was formed to emit light. A layer was deposited.
Compound 1 was deposited on the light emitting layer to form a first electron transport layer with a thickness of 5 nm.
The compound ET-1 and 8-hydroxyquinolinolato-lithium (Liq) are co-deposited on the first electron transport layer so that the proportion of Liq is 50% by mass, and a second electron transport layer with a film thickness of 20 nm is formed. was formed.
Metal Yb was deposited on the second electron transport layer to form an electron injection layer with a thickness of 1 nm.
Metallic Al was deposited on the electron injection layer to form a cathode with a thickness of 50 nm to obtain an organic EL element.

The element structure of the organic EL element of Example 1 is schematically shown as follows. The numbers in parentheses represent the film thickness (unit: nm). Moreover, the number expressed as a percentage in parentheses indicates the proportion (mass %) of the latter compound in the layer.
ITO(130)/HT-1:HI-1(10:3%)/HT-1(80)/EBL-1(5)/BH-1:BD-1(25:4%)/Compound 1( 5)/ET-1:Liq(20:50%)/Yb(1)/Al(50)

<Evaluation of organic EL elements>
The obtained organic EL device was evaluated as follows. The evaluation results are shown in Table 1.
- Driving voltage The initial characteristics of the organic EL element were measured at room temperature under DC (direct current) constant current 10 mA/cm ² driving.
- External quantum efficiency A voltage was applied to the organic EL element so that the current density was 10 mA/cm ² , and the EL emission spectrum was measured using a spectroradiometer CS-2000 (manufactured by Konica Minolta, Inc.). External quantum efficiency EQE (%) was calculated from the obtained spectral radiance spectrum.

Comparative example 1
An organic EL device was produced and evaluated in the same manner as in Example 1 except that Compound Ref was used instead of Compound 1. The results are shown in Table 1.

<Synthesis of compounds>
(Synthesis Example 1) Synthesis of Compound 1 Compound 1 was synthesized by the following synthetic route.

Under an argon atmosphere, intermediate 1 (4.80 g, 9.35 mmol), intermediate 2 (4.85 g, 13.1 mmol), PdCl ₂ (AmPhos) ₂ (265 mg, 0.374 mmol) were mixed with 1,2-dimethoxyethane. (90 mL) and a 2M aqueous sodium carbonate solution (12 mL) were added, and the mixture was heated and stirred at 70° C. for 7 hours. After the reaction was completed, extraction was performed using toluene, and the solvent was concentrated. The obtained solid was purified by column chromatography to obtain a white solid (5.93 g, yield 94%). The obtained solid was the target compound 1, and as a result of mass spectrometry analysis, it was found that the molecular weight was 676.8 and m/e = 677.

Claims (28)

A compound represented by the following formula (1).

[In formula (1),
Y is O or S.
Any one of R ₁ to R ₄ represents a bond with L ₁ . At least one of R ₁ to R ₄ that does not represent a bond with L ₁ is Ar ₁ .
Ar ₁ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted aryl group having 6 to 10 ring atoms, or a substituted or unsubstituted monovalent group having 5 to 50 ring atoms; is a heterocyclic group. However, in the above-mentioned aryl group having 6 to 10 ring carbon atoms, the substituent in the term "substituted or unsubstituted" is not an aryl group. When two or more Ar ₁ 's exist, each of the two or more Ar ₁ 's may be the same or different.
R ₁ to R ₄ that do not represent a bond with L ₁ and are not Ar ₁ are each independently a hydrogen atom or a substituent R. A set of two or more adjacent ones of R ₁ to R ₄ that do not represent a bond with L ₁ does not bond to each other.
One or more of the groups consisting of two or more adjacent ones of R ₅ to R ₈ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or Does not form unsaturated rings.
The substituted or unsubstituted saturated or unsaturated ring-forming R ₅ to R ₈ are each independently a hydrogen atom or a substituent R.
L ₁ is a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms.
n1 is an integer from 0 to 2, and when n1 is 0, (L ₁ ) _n1 is a single bond. When a plurality of L _1s exist, each of the plurality of L _1s may be the same or different.
R ₁₁ and R ₁₂ are each independently a hydrogen atom or a substituent R. R ₁₁ and R ₁₂ do not bond to each other.
One or more of the groups consisting of two or more adjacent ones of R ₁₃ to R ₁₆ are bonded to each other to form a substituted or unsubstituted saturated or unsaturated ring, or a substituted or unsubstituted saturated or Does not form unsaturated rings.
The substituted or unsubstituted saturated or unsaturated ring-forming R ₁₃ to R ₁₆ are each independently a hydrogen atom or a substituent R.
X ₁ to X ₃ are each independently N or C(R ₂₁ ), and at least two of X ₁ to X ₃ are N. R ₂₁ is a hydrogen atom or a substituent R.
Ar ₂ and Ar ₃ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
L ₂ and L ₃ are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms; It is.
n2 is an integer from 0 to 2, and when n2 is 0, (L ₂ ) _n2 is a single bond. When a plurality of L ₂ exists, each of the plurality of L ₂ may be the same or different.
n3 is an integer from 0 to 2, and when n3 is 0, (L ₃ ) _n3 is a single bond. When a plurality of L ₃ exists, each of the plurality of L ₃ may be the same or different.
The substituent R is
Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
Substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring 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 each independently,
hydrogen atom,
Substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
A substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. When two or more R ₉₀₁ to R ₉₀₇ 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 a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms and a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms.
When two or more substituents R exist, the two or more substituents R may be the same or different. ] 2. A compound according to claim 1, wherein Y is O. When Ar ₁ is a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms, the substituent in "substituted or unsubstituted" is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, The compound according to claim 1 or 2, which is a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. 4. The compound according to claim 1, wherein Ar ₁ is a substituted or unsubstituted aryl group having 6 to 10 ring carbon atoms. 5. The compound according to claim 1, wherein Ar ₁ is a substituted or unsubstituted phenyl group or a substituted or unsubstituted naphthyl group. 5. The compound according to claim 1, wherein Ar ₁ is an unsubstituted aryl group having 6 to 10 ring carbon atoms. 7. The compound according to claim 1, wherein Ar ₁ is an unsubstituted phenyl group or an unsubstituted naphthyl group. 3. The compound according to claim 1, wherein Ar ₁ is a substituted or unsubstituted monovalent heterocyclic group having 5 to 50 ring atoms. The compound according to any one of claims 1 to ₈ , wherein a group of two or more adjacent ones of R ₅ to R 8 do not bond to each other. The compound according to any one of claims 1 to 9, wherein a group of two or more adjacent ones of R ₁₃ to R ₁₆ do not bond to each other. The compound according to any one of claims 1 to 10, wherein R ₁₁ to R ₁₆ are hydrogen atoms. The compound according to any one of claims 1 to 11, wherein two of X ₁ to X ₃ are N. The compound according to any of claims 1 to 12, wherein X ₁ and X ₃ are N and X ₂ is C(R ₂₁ ). The compound according to any one of claims 1 to 13, wherein Ar ₂ and Ar ₃ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms. Claims 1 to 3, wherein Ar ₂ and Ar ₃ are each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted fluorenyl group. 15. The compound according to any one of 14. The compound according to any one of claims 1 to 15, wherein n1 is 0. The compound according to any one of claims 1 to 16, wherein n2 and n3 are 0. The compound according to claim 1, wherein the compound represented by the formula (1) is a compound represented by the following formula (11).

(In formula (11), R ₁ to R ₈ , R ₁₁ to R ₁₆ , X ₁ to X ₃ , Ar ₂ and Ar ₃ are as defined in formula (1) above.) The compound according to claim 1, wherein the compound represented by the formula (1) is a compound represented by the following formula (12).

(In formula (12), R ₁ to R ₄ , X ₁ to X ₃ , Ar ₂ and Ar ₃ are as defined in formula (1) above.) The compound according to claim 1, wherein the compound represented by the formula (1) is a compound represented by the following formula (13).

(In formula (13), R ₁ to R ₄ , Ar ₂ and Ar ₃ are as defined in formula (1) above.) The substituent in the case of “substituted or unsubstituted” and the substituent R are
an alkyl group having 1 to 50 carbon atoms,
The compound according to any one of claims 1 to 20, which is a group selected from the group consisting of an aryl group having 6 to 50 ring carbon atoms and a monovalent heterocyclic group having 5 to 50 ring atoms. The substituent in the case of “substituted or unsubstituted” and the substituent R are
an alkyl group having 1 to 18 carbon atoms,
The compound according to any one of claims 1 to 21, which is a group selected from the group consisting of an aryl group having 6 to 18 ring carbon atoms and a monovalent heterocyclic group having 5 to 18 ring atoms. The compound according to any one of claims 1 to 22, which is a material for an organic electroluminescent device. a cathode;
an anode;
one or more organic layers disposed between the cathode and the anode;
has
An organic electroluminescent device, wherein at least one of the organic layers contains the compound according to any one of claims 1 to 23. comprising an anode, a light emitting layer, an electron transport zone, and a cathode in this order,
The organic electroluminescent device according to claim 24, wherein the electron transport zone includes the compound. The electron transport zone has a first layer and a second layer in this order from the light emitting layer side,
The organic electroluminescent device according to claim 25, wherein the first layer contains the compound. 27. The organic electroluminescent device according to claim 26, wherein the first layer consists essentially of the compound. An electronic device comprising the organic electroluminescent device according to any one of claims 24 to 27.

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