WO2020218514A1

WO2020218514A1 - Compound, organic electroluminescent element and electronic device

Info

Publication number: WO2020218514A1
Application number: PCT/JP2020/017699
Authority: WO
Inventors: 太郎八巻; 裕亮糸井; 裕基中野; 聡美田崎
Original assignee: 出光興産株式会社
Priority date: 2019-04-26
Filing date: 2020-04-24
Publication date: 2020-10-29
Also published as: JP2022123149A

Abstract

A compound represented by general formula (1). In the formula, at least one of R₁₁ to R₁₈ represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group or a substituted or unsubstituted terphenyl group.

Description

Compounds, organic electroluminescence devices and electronic devices

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

When a voltage is applied to an organic electroluminescence device (hereinafter, may be referred to as an “organic EL device”), holes are injected into the light emitting layer from the anode, and electrons are injected into the light emitting layer from the cathode. Then, in the light emitting layer, the injected holes and electrons are recombined to form excitons. At this time, according to the statistical law of electron spin, singlet excitons are generated at a rate of 25%, and triplet excitons are generated at a rate of 75%.
Organic EL elements are applied to full-color displays such as mobile phones and televisions. In order to improve the performance of organic EL devices, various studies have been conducted on compounds used in organic EL devices (see, for example, Patent Documents 1 to 5). Examples of the performance of the organic EL element include brightness, emission wavelength, chromaticity, luminous efficiency, drive voltage, and life.

Korean Publication No. 10-2013-0075982 U.S. Patent Application Publication No. 2016/0351818 International Publication No. 2010/013676 International Publication No. 2010/114263 U.S. Patent Application Publication No. 2016/0351817

The present invention provides a compound capable of lowering the drive voltage of an organic electroluminescence device, provides an organic electroluminescence device having a lowered drive voltage, and provides an electronic device equipped with the organic electroluminescence device. The purpose is to do.

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

(In the general formula (1),
One or more of two or more adjacent pairs of R ₁₁ , R ₁₂ , R ₁₇ and R ₁₈
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
One or more of two or more adjacent pairs of R ₁₃ , R ₁₄ , R ₁₅ and R ₁₆
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
R ₁₁ to R ₁₈ that do not form the monocyclic ring and do not form the condensed ring are independent of each other.
Hydrogen atom,
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
However, at least one of R ₁₁ to R ₁₈ is
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L ₁₁ is a substituted or unsubstituted ring-forming carbon number 6 to 13 arylene group.
m is 0, 1, or 2
When m is 0, the fused ring containing X in the general formula (1) and the anthracene ring are bonded by a single bond.
when m is 2, two _{L 11} may be identical to each other or different,
Sets of the two _{L 11} is
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
X is an oxygen atom or a sulfur atom,
Of R ₁₀₁ to R ₁₀₇ , one or more pairs of two or more adjacent pairs do not join each other.
R ₁₀₁ to R ₁₀₇ are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Cyano group,
Halogen atom,
-A group represented by Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
A group represented by -O- (R ₉₀₄ ),
A group represented by -S- (R ₉₀₅ ),
A group represented by -N (R ₉₀₆ ) (R ₉₀₇ ),
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
Ar ₃ is
A group represented by the following general formula (1a),
The group represented by the following general formula (1b),
A group represented by the following general formula (1c),
A group represented by the following general formula (1d),
Substituted or unsubstituted fluorenyl group,
A substituted or unsubstituted ring-forming aryl group having 15 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 16 atoms.
However, Ar ₃ bonded to one of the 9-position carbon atom and the 10-position carbon atom of the anthracene ring shown in the general formula (1) and the other of the 9-position carbon atom and the 10-position carbon atom of the anthracene ring The groups to which they bind are different from each other. )

(In the general formula (1a), R ₁₁₁ to R ₁₁₅ are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Cyano group,
Halogen atom,
-A group represented by Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
A group represented by -O- (R ₉₀₄ ),
A group represented by -S- (R ₉₀₅ ),
A group represented by -N (R ₉₀₆ ) (R ₉₀₇ ),
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
However, when m is 0, the general formula (1a) satisfies the following condition (i) or (ii).
(I) At least one of R ₁₁₁ to R ₁₁₅ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted ring-forming carbon. Cycloalkyl group of number 3 to 50, cyano group, halogen atom, group represented by -Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ), group represented by -O- (R ₉₀₄ ), -S A group represented _by- (R ₉₀₅ ), a group represented by -N (R ₉₀₆ ) (R ₉₀₇ ), a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring. It is a heterocyclic group having 5 to 50 atoms.
(Ii) R ₁₁₁ to R ₁₁₅ are hydrogen atoms, and at least one of R ₁₁ to R ₁₈ is independently substituted phenyl group, substituted or unsubstituted biphenyl group, or substituted or unsubstituted. It is a terphenyl group. )

(In the general formula (1b), R ₁₂₁ to R ₁₂₇ are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Cyano group,
Halogen atom,
-A group represented by Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
A group represented by -O- (R ₉₀₄ ),
A group represented by -S- (R ₉₀₅ ),
A group represented by -N (R ₉₀₆ ) (R ₉₀₇ ),
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
However, the general formula (1b) satisfies the following condition (iii) or (iv).
(Iii) At least one of R ₁₂₁ to R ₁₂₇ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted ring formation. Cycloalkyl group having 3 to 50 carbon atoms, cyano group, halogen atom, group represented by -Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ), group represented by -O- (R ₉₀₄ ),- A group represented by S- (R ₉₀₅ ), a group represented by -N (R ₉₀₆ ) (R ₉₀₇ ), a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted aryl group. It is a heterocyclic group having 5 to 50 ring-forming atoms.
(Iv) R ₁₂₁ to R ₁₂₇ are hydrogen atoms, and at least one of R ₁₁ to R ₁₈ is independently substituted phenyl group, substituted or unsubstituted biphenyl group, or substituted or unsubstituted. It is a terphenyl group. )

(In the general formula (1c),
When m is 0, R ₁₃₁ to R ₁₃₇ are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Cyano group,
Halogen atom,
-A group represented by Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
A group represented by -O- (R ₉₀₄ ),
A group represented by -S- (R ₉₀₅ ),
A group represented by -N (R ₉₀₆ ) (R ₉₀₇ ),
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
When m is 1 or 2, at least one of R ₁₃₁ to R ₁₃₇ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, substituted or unsubstituted. Substituent ring formation Cycloalkyl group having 3 to 50 carbon atoms, cyano group, halogen atom, group represented by -Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ), represented by -O- (R ₉₀₄ ). Group, a group represented by -S- (R ₉₀₅ ), a group represented by -N (R ₉₀₆ ) (R ₉₀₇ ), a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted group. Alternatively, it is an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. )

(In the general formula (1d),
L ₁₂ is a substituted or unsubstituted ring-forming carbon number 6 to 13 arylene group.
HAR is a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. )
(R ₉₀₁ , R ₉₀₂ , R ₉₀₃ , R ₉₀₄ , R ₉₀₅ , R ₉₀₆ and R ₉₀₇ in the general formulas (1), (1a) to (1c) are independent of each other.
Substituent or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
Substituted or unsubstituted ring-forming heterocyclic groups having 5 to 50 atoms,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms.
If R ₉₀₁ is plural, _{R 901} may be identical to each other or different,
If R ₉₀₂ is plural, _{R 902} may be identical to each other or different,
If R ₉₀₃ is plural, _{R 903} may be identical to each other or different,
If R ₉₀₄ is plural, _{R 904} may be identical to each other or different,
If R ₉₀₅ is plural, _{R 905} may be identical to each other or different,
When there are multiple R- _906s , the plurality of R- _906s are the same as or different from each other.
If R ₉₀₇ is plural, _{R 907} may be identical to each other or different,
* In the general formulas (1a) to (1d) indicate the bonding position with the anthracene ring. )

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

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

According to one aspect of the present invention, providing a compound capable of lowering the drive voltage of the organic electroluminescence device, providing an organic electroluminescence device having a lowered drive voltage, and mounting the organic electroluminescence device. Electronic devices can be provided.

It is a figure which shows the schematic structure of an example of the organic electroluminescence device which concerns on one Embodiment of this invention.

[Definition]
In the present specification, a hydrogen atom includes isotopes having different numbers of neutrons, that is, hydrogen (protium), deuterium (deuterium), and tritium (tritium).

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

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

In the present specification, the number of ring-forming atoms refers to a compound (for example, a monocyclic compound, a fused ring compound, a crosslinked compound, a carbocycle) having a structure in which atoms are cyclically bonded (for example, a monocycle, a fused ring, and a ring assembly). Represents the number of atoms constituting the ring itself of a compound and a heterocyclic compound). Atoms that do not form a ring (for example, a hydrogen atom that terminates the bond of atoms that form a ring) and atoms that are included in the substituent when the ring is substituted by a substituent are not included in the number of ring-forming atoms. The "number of ring-forming atoms" described below shall be the same unless otherwise specified. For example, the pyridine ring has 6 ring-forming atoms, the quinazoline ring has 10 ring-forming atoms, and the furan ring has 5 ring-forming atoms. For example, the number of hydrogen atoms bonded to the pyridine ring or the number of atoms constituting the substituent is not included in the number of pyridine ring-forming atoms. Therefore, the number of ring-forming atoms of the pyridine ring to which the hydrogen atom or the substituent is bonded is 6. Further, for example, a hydrogen atom bonded to a carbon atom of a quinazoline ring or an atom constituting a substituent is not included in the number of ring-forming atoms of the quinazoline ring. Therefore, the number of ring-forming atoms of the quinazoline ring to which the hydrogen atom or the substituent is bonded is 10.

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

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

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

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

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

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

• Unsubstituted aryl group (Specific example group G1A):
Phenyl group,
p-biphenyl group,
m-biphenyl group,
o-biphenyl group,
p-terphenyl-4-yl group,
p-terphenyl-3-yl group,
p-terphenyl-2-yl group,
m-terphenyl-4-yl group,
m-terphenyl-3-yl group,
m-terphenyl-2-yl group,
o-terphenyl-4-yl group,
o-terphenyl-3-yl group,
o-terphenyl-2-yl group,
1-naphthyl group,
2-naphthyl group,
Anthril group,
Benzodiazepine tolyl group,
Phenantril group,
Benzophenanthryl group,
Fenarenyl group,
Pyrenyl group,
Chrysenyl group,
Benzocrisenyl group,
Triphenylenyl group,
Benzodiazepineyl group,
Tetrasenyl group,
Pentacenyl group,
Fluorenyl group,
9,9'-spirobifluorenyl group,
Benzofluorenyl group,
Dibenzofluorenyl group,
Fluorantenyl group,
Benzodiazepineyl group,
A perylenyl group and a monovalent aryl group derived by removing one hydrogen atom from the ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

-Substituted aryl group (Specific example group G1B):
o-tolyl group,
m-tolyl group,
p-tolyl group,
Parakisilyl group,
Meta-kisilyl group,
Ortho-kisilyl group,
Para-isopropylphenyl group,
Meta-isopropylphenyl group,
Ortho-isopropylphenyl group,
Para-t-butylphenyl group,
Meta-t-butylphenyl group,
Ortho-t-butylphenyl group,
3,4,5-trimethylphenyl group,
9,9-Dimethylfluorenyl group,
9,9-diphenylfluorenyl group,
9,9-bis (4-methylphenyl) fluorenyl group,
9,9-bis (4-isopropylphenyl) fluorenyl group,
9,9-bis (4-t-butylphenyl) fluorenyl group,
Cyanophenyl group,
Triphenylsilylphenyl group,
Trimethylsilylphenyl group,
Phenylnaphthyl group,
A naphthylphenyl group and a group in which one or more hydrogen atoms of a monovalent group derived from the ring structure represented by the general formulas (TEMP-1) to (TEMP-15) are replaced with a substituent.

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

The specific example group G2A includes, for example, an unsubstituted heterocyclic group containing the following nitrogen atom (specific example group G2A1), an unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2), and an unsubstituted heterocyclic group containing a sulfur atom. (Specific example group G2A3) and a monovalent heterocyclic group 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) is included.

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

-Unsubstituted heterocyclic group containing a nitrogen atom (specific example group G2A1):
Pyrrolyl group,
Imidazolyl group,
Pyrazolyl group,
Triazolyl group,
Tetrazoleyl group,
Oxazolyl group,
Isooxazolyl group,
Oxaziazolyl group,
Thiazolyl group,
Isothiazolyl group,
Thiasia Zoryl group,
Pyridyl group,
Pyridadinyl group,
Pyrimidinyl group,
Pyrazinel group,
Triazinyl group,
Indrill group,
Isoin drill group,
Indridinyl group,
Kinolidinyl group,
Quinoline group,
Isoquinolyl group,
Synnolyl group,
Phthaladinyl group,
Kinazolinyl group,
Kinoxalinyl group,
Benzoimidazolyl group,
Indazolyl group,
Phenantrolinyl group,
Phenantridinyl group,
Acridinyl group,
Phenazinyl group,
Carbazoleyl group,
Benzodiazepine group,
Morpholine group,
Phenoxadinyl group,
Phenothiadinyl group,
Azacarbazolyl group and diazacarbazolyl group.

-Unsubstituted heterocyclic group containing an oxygen atom (specific example group G2A2):
Frill group,
Oxazolyl group,
Isooxazolyl group,
Oxaziazolyl group,
Xanthenyl group,
Benzofuranyl group,
Isobenzofuranyl group,
Dibenzofuranyl group,
Naftbenzofuranyl group,
Benzoxazolyl group,
Benzoisoxazolyl group,
Phenoxadinyl group,
Morpholine group,
Ginaftfuranyl group,
Azadibenzofuranyl group,
Diazadibenzofuranyl group,
Azanaftbenzofuranyl group and diazanaphthobenzofuranyl group.

-Unsubstituted heterocyclic group containing a sulfur atom (specific example group G2A3):
Thienyl group,
Thiazolyl group,
Isothiazolyl group,
Thiasia Zoryl group,
Benzothiophenyl group (benzothienyl group),
Isobenzothiophenyl group (isobenzothienyl group),
Dibenzothiophenyl group (dibenzothienyl group),
Naftbenzothiophenyl group (naphthobenzothienyl group),
Benzothiazolyl group,
Benzoisothiazolyl group,
Phenothiadinyl group,
Dinaftthiophenyl group (dinaftthienyl group),
Azadibenzothiophenyl group (azadibenzothienyl group),
Diazadibenzothiophenyl group (diazadibenzothienyl group),
Azanaftbenzothiophenyl group (azanaftbenzothienyl group) and diazanaphthobenzothiophenyl group (diazanaftbenzothienyl group).

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

In Formula (TEMP-16) ~ (TEMP -33), the _{X A} and _{Y A,} each independently, an oxygen atom, a sulfur atom, NH, or is CH _2. Provided that at least one of _{X A} and _{Y A} represents an oxygen atom, a sulfur atom, or is NH.
In Formula (TEMP-16) ~ (TEMP -33), at least one is NH of _{X A} and _{Y A,} or a CH _2, in the general formula (TEMP-16) ~ (TEMP -33) The monovalent heterocyclic group derived from the ring structure represented includes a monovalent group obtained by removing one hydrogen atom from these NH or CH ₂ .

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

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

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

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

The term "monovalent one or more hydrogen atoms of the heterocyclic group", said monovalent hydrogen atoms bonded to ring carbon atoms of the heterocyclic group, at least one of X _A and Y _A is NH the hydrogen atoms attached to the nitrogen atom of the case where, and one of X _a and Y _a means one or more hydrogen atoms selected from a hydrogen atom of the methylene group in the case is CH _2.

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

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

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

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

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

Substituent alkenyl group (specific example group G4B):
1,3-Butandienyl group,
1-Methyl vinyl group,
1-methylallyl group,
1,1-dimethylallyl group,
2-Methylallyl group and 1,2-dimethylallyl group.

-"Substituted or unsubstituted alkynyl group"
Specific examples (specific example group G5) of the "substituted or unsubstituted alkynyl group" described in the present specification include the following unsubstituted alkynyl groups (specific example group G5A) and the like. (Here, the unsubstituted alkynyl group refers to the case where the "substituted or unsubstituted alkynyl group" is the "unsubstituted alkynyl group".) Hereinafter, the term "alkynyl group" is simply referred to as "unsubstituted alkynyl group". Includes both "alkynyl groups" and "substituted alkynyl groups".
The "substituted alkynyl group" means a group in which one or more hydrogen atoms in the "unsubstituted alkynyl group" are replaced with a substituent. Specific examples of the "substituted alkynyl group" include a group in which one or more hydrogen atoms are replaced with a substituent in the following "unsubstituted alkynyl group" (specific example group G5A).

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

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

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

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

-"A group represented by -Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ )"
Specific examples (specific example group G7) of the groups represented by −Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ) described in the present specification 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 the "substituted or unsubstituted aryl group" described in the specific example group G1.
G2 is the "substituted or unsubstituted heterocyclic group" described in the specific example group G2.
G3 is the "substituted or unsubstituted alkyl group" described in the specific example group G3.
G6 is the "substituted or unsubstituted cycloalkyl group" described in the specific example group G6.
-A plurality of G1s in Si (G1) (G1) (G1) are the same as or different from each other.
-A plurality of G2s in Si (G1) (G2) (G2) are the same as or different from each other.
-A plurality of G1s in Si (G1) (G1) (G2) are the same as or different from each other.
-A plurality of G2s in Si (G2) (G2) (G2) are the same as or different from each other.
-A plurality of G3s in Si (G3) (G3) (G3) are the same as or different from each other.
-A plurality of G6s in Si (G6) (G6) (G6) are the same as or different from each other.

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

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

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

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

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

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

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

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

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

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

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

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

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

The substituted or unsubstituted heterocyclic groups described herein are preferably pyridyl, pyrimidinyl, triazinyl, quinolyl, isoquinolyl, quinazolinyl, benzoimidazolyl, fe, unless otherwise stated herein. Nantrolinyl group, carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group , Dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, ( 9-phenyl) carbazolyl group ((9-phenyl) carbazole-1-yl group, (9-phenyl) carbazole-2-yl group, (9-phenyl) carbazole-3-yl group, or (9-phenyl) carbazole group -4-yl group), (9-biphenylyl) carbazolyl group, (9-phenyl) phenylcarbazolyl group, diphenylcarbazole-9-yl group, phenylcarbazole-9-yl group, phenyltriazinyl group, biphenylylt A riazinyl group, a diphenyltriazinyl group, a phenyldibenzofuranyl group, a phenyldibenzothiophenyl group and the like.

In the present specification, the carbazolyl group is specifically one of the following groups unless otherwise described in the present specification.

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

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

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

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

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

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

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

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

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

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

In the general formula (TEMP-53) ~ (TEMP -62), Q 1 ~ Q 10 are each independently a hydrogen atom or a substituent.
The formulas Q ₉ and Q ₁₀ may be bonded to each other via a single bond to form a ring.
In the general formulas (TEMP-53) to (TEMP-62), * represents a bonding position.

In the general formula (TEMP-63) ~ (TEMP -68), Q 1 ~ Q 8 are each independently hydrogen atom or a substituent.
In the general formulas (TEMP-63) to (TEMP-68), * represents a bonding position.

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

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

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

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

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

For example, in the case of "one or more sets of two or more adjacent sets of R ₉₂₁ to R ₉₃₀ are combined with each other to form a ring", the set of two adjacent sets is one set. Is a pair of R ₉₂₁ and R ₉₂₂ , a pair of R ₉₂₂ and R ₉₂₃ , a pair of R ₉₂₃ and R ₉₂₄ , a pair of R ₉₂₄ and R ₉₃₀ , a pair of R ₉₃₀ and R _925, and a pair of R ₉₂₅ . A pair with R ₉₂₆ , a pair with R ₉₂₆ and R ₉₂₇ , a pair with R ₉₂₇ and R ₉₂₈ , a pair with R ₉₂₈ and R _929, and a pair with R ₉₂₉ and R ₉₂₁ .

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

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

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

The "unsaturated ring" means an aromatic hydrocarbon ring or an aromatic heterocycle. By "saturated ring" is meant an aliphatic hydrocarbon ring or a non-aromatic heterocycle.
Specific examples of the aromatic hydrocarbon ring include a structure in which the group given as a specific example in the specific example group G1 is terminated by a hydrogen atom.
Specific examples of the aromatic heterocycle include a structure in which the aromatic heterocyclic group given as a specific example in the specific example group G2 is terminated by a hydrogen atom.
Specific examples of the aliphatic hydrocarbon ring include a structure in which the group given as a specific example in the specific example group G6 is terminated by a hydrogen atom.
By "forming a ring" is meant forming a ring with only a plurality of atoms in the mother skeleton, or with a plurality of atoms in the mother skeleton and one or more arbitrary elements. For example, the shown in the general formula _(TEMP-104), the ring _{Q A} where the _{R 921} and _{R 922} are bonded formed with each _other, the carbon atoms of the anthracene _{skeleton R 921} are _{attached, anthracene R 922} are bonded It means a ring formed by a carbon atom of a skeleton and one or more arbitrary elements. As a specific _example, in the case of forming the ring _{Q A} in the _{R 921} and _{R _922,} and the carbon atoms of the anthracene _{skeleton R 921} are _attached, the carbon atom of the anthracene skeleton and _{R 922} are attached, four carbon atoms When a monocyclic unsaturated ring is formed with and, the ring formed by R ₉₂₁ and R ₉₂₂ is a benzene ring.

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

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

Substituent in the case of "substitution or unsubstituted" In one embodiment of the present specification, the substituent in the case of "substitution or unsubstituted" (referred to as "arbitrary substituent" in the present specification). ), For example,
Unsubstituted alkyl groups with 1 to 50 carbon atoms,
An unsubstituted alkenyl group having 2 to 50 carbon atoms,
An unsubstituted alkynyl group having 2 to 50 carbon atoms,
Unsubstituted ring-forming cycloalkyl group with 3 to 50 carbon atoms,
-Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
-O- (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom, cyano group, nitro group,
It is a group selected from the group consisting of an aryl group having an unsubstituted ring-forming carbon number of 6 to 50 and a heterocyclic group having an unsubstituted ring-forming atom number of 5 to 50.
here,
R ₉₀₁ to R ₉₀₇ are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
If there are two or more R _901s , the two or more R _901s are the same or different from each other.
If there are two or more R _902s , the two or more R _902s are the same or different from each other.
If there are two or more R _903s , the two or more R _903s are the same or different from each other.
If there are two or more R _904s , the two or more R _904s are the same or different from each other.
If there are two or more R _905s , the two or more R _905s are the same or different from each other.
If there are two or more R- _906s , the two or more R- _906s are the same or different from each other.
If there are two or more R _907s , the two or more R _907s are the same or different from each other.

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

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

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

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

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

[First Embodiment]
(Compound)
The compound according to this embodiment is a compound represented by the following general formula (1).

The "group bonded to the other of the 9-position carbon atom and the 10-position carbon atom of the anthracene ring" is a group represented by the following general formula (1x).

In the general formula (1x), L ₁₁ , m, X, and R ₁₀₁ to R ₁₀₇ are synonymous with L ₁₁ , m, X, and R ₁₀₁ to R ₁₀₇ in the general formula (1), respectively. * Indicates the bond position with the anthracene ring.

(In the general formula (1a),
R ₁₁₁ to R ₁₁₅ are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Cyano group,
Halogen atom,
-A group represented by Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
A group represented by -O- (R ₉₀₄ ),
A group represented by -S- (R ₉₀₅ ),
A group represented by -N (R ₉₀₆ ) (R ₉₀₇ ),
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
However, when m is 0, the general formula (1a) satisfies the following condition (i) or (ii).
(I) At least one of R ₁₁₁ to R ₁₁₅ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted ring-forming carbon. Cycloalkyl group of number 3 to 50, cyano group, halogen atom, group represented by -Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ), group represented by -O- (R ₉₀₄ ), -S A group represented _by- (R ₉₀₅ ), a group represented by -N (R ₉₀₆ ) (R ₉₀₇ ), a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring. It is a heterocyclic group having 5 to 50 atoms.
(Ii) R ₁₁₁ to R ₁₁₅ are hydrogen atoms, and at least one of R ₁₁ to R ₁₈ is independently substituted phenyl group, substituted or unsubstituted biphenyl group, or substituted or unsubstituted. It is a terphenyl group.

However, among R ₁₁₁ to R ₁₁₅ in the compound of the present embodiment, one or more pairs of two or more adjacent pairs do not bind to each other.

In the general formula (1a), R ₁₁₁ to R ₁₁₅ are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Cyano group,
Halogen atom,
-A group represented by Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
It is also preferable that it is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms or a heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.

In the general formula (1a), R ₁₁₁ to R ₁₁₅ are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
It is also preferable that it is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms or a heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.

In the general formula (1a), R ₁₁₁ to R ₁₁₅ are independent of each other.
Hydrogen atom,
Unsubstituted alkyl groups with 1 to 50 carbon atoms,
It is also preferable that it is an aryl group having an unsubstituted ring-forming carbon number of 6 to 50 or a heterocyclic group having an unsubstituted ring-forming atom number of 5 to 50.

It is also preferable that the aryl group having 6 to 50 carbon atoms forming a ring as R ₁₁₁ to R ₁₁₅ of the general formula (1a) is not an anthryl group.

When m is 0, the general formula (1a) preferably satisfies the following condition (i-1) or the condition (ii).
(I-1) At least one of R ₁₁₁ to R ₁₁₅ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted ring. A cycloalkyl group having 3 to 50 carbon atoms, a cyano group, a halogen atom, a group represented by −Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ), and a substituted or unsubstituted ring-forming carbon number of 6 to 50. It is an aryl group or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.

When m is 0, the general formula (1a) preferably satisfies the following condition (i-2) or the condition (ii).
(I-2) At least one of R ₁₁₁ to R ₁₁₅ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted alkyl group. A substituted ring-forming heterocyclic group having 5 to 50 atomic atoms.

When m is 0, the general formula (1a) preferably satisfies the following condition (i-3) or the condition (ii).
(I-3) At least one of R ₁₁₁ to R ₁₁₅ is an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted aryl group having 6 to 50 carbon atoms, or an unsubstituted ring-forming atomic number. It is a heterocyclic group of 5 to 50.

However, among R ₁₂₁ to R ₁₂₇ in the compound of the present embodiment, one or more sets of two or more adjacent sets do not bind to each other.

In the general formula (1b), R ₁₂₁ to R ₁₂₇ are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Cyano group,
Halogen atom,
-A group represented by Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
It is also preferable that the general formula (1b) satisfies the following condition (iii-1) or the above condition (iv).
(Iii-1) At least one of R ₁₂₁ to R ₁₂₇ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, substituted or unsubstituted. Cycloalkyl group having 3 to 50 ring-forming carbon atoms, cyano group, halogen atom, group represented by -Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ), substituted or unsubstituted ring-forming carbon number 6 to 50 Aryl group or a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms.

In the general formula (1b), R ₁₂₁ to R ₁₂₇ are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
It is also preferable that the general formula (1b) satisfies the following condition (iii-2) or the above condition (iv).
(Iii-2) At least one of R ₁₂₁ to R ₁₂₇ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or substituted ring. It is an unsubstituted heterocyclic group having 5 to 50 atoms.

In the general formula (1b), R ₁₂₁ to R ₁₂₇ are independent of each other.
Hydrogen atom,
Unsubstituted alkyl groups with 1 to 50 carbon atoms,
An unsubstituted ring-forming aryl group having 6 to 50 carbon atoms or an unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
It is also preferable that the general formula (1b) satisfies the following condition (iii-3) or the above condition (iv).
(Iii-3) At least one of R ₁₂₁ to R ₁₂₇ is an unsubstituted alkyl group having 1 to 50 carbon atoms, an unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or an unsubstituted ring-forming atom. It is a heterocyclic group of the number 5 to 50.

It is also preferable that the aryl group having 6 to 50 carbon atoms forming a ring as R ₁₂₁ to R ₁₂₇ of the general formula (1b) is not an anthryl group.

However, of R ₁₃₁ to R ₁₃₇ in the compound of the present embodiment, one or more sets of two or more adjacent sets do not bind to each other.

In the general formula (1c), when m is 0, R ₁₃₁ to R ₁₃₇ are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Cyano group,
Halogen atom,
-A group represented by Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
It is also preferable that it is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms or a heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.

In the general formula (1c), when m is 0, R ₁₃₁ to R ₁₃₇ are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
It is also preferable that it is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms or a heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.

In the general formula (1c), when m is 0, R ₁₃₁ to R ₁₃₇ are independent of each other.
Hydrogen atom,
Unsubstituted alkyl groups with 1 to 50 carbon atoms,
It is also preferable that it is an aryl group having an unsubstituted ring-forming carbon number of 6 to 50 or a heterocyclic group having an unsubstituted ring-forming atom number of 5 to 50.

In the general formula (1c), when m is 1 or 2, at least one of R ₁₃₁ to R ₁₃₇ is independent of each other.
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Cyano group,
Halogen atom,
-A group represented by Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
It is also preferable that it is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms or a heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.

In the general formula (1c), when m is 1 or 2, at least one of R ₁₃₁ to R ₁₃₇ is independent of each other.
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
It is also preferable that it is an aryl group having 6 to 50 substituted or unsubstituted ring-forming carbon atoms or a heterocyclic group having 5 to 50 substituted or unsubstituted ring-forming atoms.

In the general formula (1c), when m is 1 or 2, at least one of R ₁₃₁ to R ₁₃₇ is independent of each other.
Unsubstituted alkyl groups with 1 to 50 carbon atoms,
It is also preferable that it is an aryl group having an unsubstituted ring-forming carbon number of 6 to 50 or a heterocyclic group having an unsubstituted ring-forming atom number of 5 to 50.

It is also preferable that the aryl group having 6 to 50 carbon atoms forming a ring as R ₁₃₁ to R ₁₃₇ of the general formula (1c) is not an anthryl group.

(In the general formula (1d),
L ₁₂ is a substituted or unsubstituted ring-forming carbon number 6 to 13 arylene group.
HAR is a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. )

(R ₉₀₁ , R ₉₀₂ , R ₉₀₃ , R ₉₀₄ , R ₉₀₅ , R ₉₀₆ and R ₉₀₇ in the general formulas (1), (1a) to (1c) are independent of each other.
Substituent or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
Substituted or unsubstituted ring-forming heterocyclic groups having 5 to 50 atoms,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms.
If R ₉₀₁ is plural, _{R 901} may be identical to each other or different,
If R ₉₀₂ is plural, _{R 902} may be identical to each other or different,
If R ₉₀₃ is plural, _{R 903} may be identical to each other or different,
If R ₉₀₄ is plural, _{R 904} may be identical to each other or different,
If R ₉₀₅ is plural, _{R 905} may be identical to each other or different,
When there are multiple R- _906s , the plurality of R- _906s are the same as or different from each other.
If R ₉₀₇ is plural, _{R 907} may be identical to each other or different,
* In the general formulas (1a) to (1d) indicate the bonding position with the anthracene ring. )

In the compound according to this embodiment, it is preferable that at least one of R ₁₁ and R ₁₈ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

In the compound according to the present embodiment, one of R ₁₁ and R ₁₈ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group, and R ₁₁ and R ₁₈ The other is more preferably a hydrogen atom.

In the compound according to the present embodiment, it is preferable that R ₁₃ to R ₁₆ are hydrogen atoms.

In the compound according to this embodiment, any one of R ₁₁ , R ₁₂ , R ₁₇ , and R ₁₈ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group. It is more preferable that the remaining three of R ₁₁ , R ₁₂ , R ₁₇ and R ₁₈ are hydrogen atoms.
Further, in the compound according to the present embodiment, any one of R ₁₁ , R ₁₂ , R ₁₇ and R ₁₈ is a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted atom. It is also preferable that it is a phenyl group, the remaining three of R ₁₁ , R ₁₂ , R ₁₇ and R ₁₈ are hydrogen atoms, and R ₁₃ to R ₁₆ are hydrogen atoms. In this case, the compound according to this embodiment is represented by any of the following general formulas (11) to (14).

_{(R 11} in the general formula (11), _{R 12} in the general formula (12), _{R 17} in _{R 18,} and the general formula (14) in the general formula (13) are each independently,
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
_L 11 in the general formula _{(11) ~ (14),} m, X, R 101 ~ R 107, and Ar _3, respectively, wherein _L 11 in the general formula _{(1), m, X,} R 101 ~ R 107 , And Ar ₃ are synonymous with
However, Ar ₃ bonded to one of the 9-position carbon atom and the 10-position carbon atom of the anthracene ring shown in the general formulas (11) to (14), and the 9-position carbon atom and the 10-position carbon of the anthracene ring. The groups attached to the other of the atoms are different from each other. )

The compound according to the present embodiment is preferably a compound represented by the general formula (11) among the compounds represented by the general formulas (11) to (14).

In the compound according to this embodiment, it is also preferable that m is 0.
When m is 0, the structure in which the condensed ring containing X and the anthracene ring in the general formula (1) are bonded by a single bond is a structure represented by the following general formula (1X).

In the general formula _{_{_{(1X), R 11 ~ R}}} 18, R 101 ~ R 107, and Ar _3, respectively, and _{_{_{R 11 ~ R 18, R 101}}} ~ R 107, and Ar ₃ in the general formula (1) It is synonymous.

In the compound according to this embodiment, it is also preferable that m is 1 or 2.
In the compound according to this embodiment, it is also preferable that m is 1.

In the compound according to the present embodiment, Ar ₃ is also preferably a group represented by the general formula (1a).

For example, in the compound represented by the general formula (11), when Ar ₃ is a group represented by the general formula (1a), the compound according to the present embodiment is represented by the following general formula (11a). To.

(R ₁₁ in the general formula (11a) is
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L _11, m, X, and _R 101 _{~ R 107} are each, the _L 11 in the general formula (1), m, has the same meaning X, and the _R 101 _{~ R 107,}
R ₁₁₁ to R ₁₁₅ are independently synonymous with R ₁₁₁ to R ₁₁₅ in the general formula (1a). )

The compound represented by the general formula (11a) is represented by the following general formula (111a) when m is 0.

R ₁₁ in the general formula (111a) is
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
X and R ₁₀₁ to R ₁₀₇ are synonymous with X and R ₁₀₁ to R ₁₀₇ in the general formula (1), respectively.
R ₁₁₁ to R ₁₁₅ are independently synonymous with R ₁₁₁ to R ₁₁₅ in the general formula (1a), and R ₉₀₁ to R ₉₀₇ are independently independent of R ₉₀₁ to R ₉₀₁ in the general formula (1a). It is synonymous with R ₉₀₇ .
However, the compound represented by the general formula (111a) satisfies the following conditions (i) or (ii).

(I) At least one of R ₁₁₁ to R ₁₁₅ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted ring-forming carbon. Cycloalkyl group of number 3 to 50, cyano group, halogen atom, group represented by -Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ), group represented by -O- (R ₉₀₄ ), -S A group represented _by- (R ₉₀₅ ), a group represented by -N (R ₉₀₆ ) (R ₉₀₇ ), a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring. It is a heterocyclic group having 5 to 50 atoms.

(Ii) R ₁₁₁ to R ₁₁₅ are hydrogen atoms, and R ₁₁ is a substituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

In the compound represented by the general formula (11a), when m is 1, the compound according to the present embodiment is represented by the following general formula (112a).
In the compound represented by the general formula (11a), when m is 2, the compound according to the present embodiment is represented by the following general formula (113a).

(R ₁₁ in the general formulas (112a) and (113a) are independent of each other.
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L ₁₁ , L ₁₁₁ and L ₁₁₂ are independently substituted or unsubstituted ring-forming arylene groups having 6 to 13 carbon atoms, respectively.
The set consisting of L ₁₁₁ and L ₁₁₂ is
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
X and R ₁₀₁ to R ₁₀₇ are synonymous with X and R ₁₀₁ to R ₁₀₇ in the general formula (1), respectively.
R ₁₁₁ to R ₁₁₅ are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Cyano group,
Halogen atom,
-A group represented by Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
A group represented by -O- (R ₉₀₄ ),
A group represented by -S- (R ₉₀₅ ),
A group represented by -N (R ₉₀₆ ) (R ₉₀₇ ),
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
R ₉₀₁ to R ₉₀₇ are independently synonymous with R ₉₀₁ to R ₉₀₇ in the general formula (1a). )

The compound according to the present embodiment is preferably a compound represented by the general formula (13) among the compounds represented by the general formulas (11) to (14).

For example, in the compound represented by the general formula (13), when Ar ₃ is a group represented by the general formula (1a), the compound according to the present embodiment is represented by the following general formula (13a). To.

(R ₁₈ in the general formula (13a) is
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L _11, m, X, and _R 101 _{~ R 107} are each, the _L 11 in the general formula (1), m, has the same meaning X, and the _R 101 _{~ R 107,}
R ₁₁₁ to R ₁₁₅ are independently synonymous with R ₁₁₁ to R ₁₁₅ in the general formula (1a). )

In the compound represented by the general formula (13a), when m is 0, it is represented by the following general formula (131a).

(R ₁₈ in the general formula (131a) is
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
X and R ₁₀₁ to R ₁₀₇ are synonymous with X and R ₁₀₁ to R ₁₀₇ in the general formula (1), respectively.
R ₁₁₁ to R ₁₁₅ are independently synonymous with R ₁₁₁ to R ₁₁₅ in the general formula (1a).
R ₉₀₁ to R ₉₀₇ are independently synonymous with R ₉₀₁ to R ₉₀₇ in the general formula (1a).
However, the compound represented by the general formula (131a) satisfies the following conditions (v) or (vi). )

(V) At least one of R ₁₁₁ to R ₁₁₅ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted ring-forming carbon. Cycloalkyl group of number 3 to 50, cyano group, halogen atom, group represented by -Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ), group represented by -O- (R ₉₀₄ ), -S A group represented _by- (R ₉₀₅ ), a group represented by -N (R ₉₀₆ ) (R ₉₀₇ ), a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring. It is a heterocyclic group having 5 to 50 atoms.

(Vi) R ₁₁₁ to R ₁₁₅ are hydrogen atoms, and R ₁₈ is a substituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.

In the compound according to the present embodiment, Ar ₃ is preferably a group represented by the general formula (1b) or a group represented by the general formula (1c).

For example, in the compound represented by the general formula (11), when Ar ₃ is a group represented by the general formula (1b), the compound according to the present embodiment is represented by the following general formula (11b). To.

(R ₁₁ in the general formula (11b) is
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L _11, m, X, and _R 101 _{~ R 107} are each, the _L 11 in the general formula (1), m, has the same meaning X, and the _R 101 _{~ R 107,}
R ₁₂₁ to R ₁₂₇ are independently synonymous with R ₁₂₁ to R ₁₂₇ in the general formula (1b).
However, the compound represented by the general formula (11b) satisfies the following conditions (iii) or (iv).
(Iii) At least one of R ₁₂₁ to R ₁₂₇ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted ring formation. Cycloalkyl group having 3 to 50 carbon atoms, cyano group, halogen atom, group represented by -Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ), group represented by -O- (R ₉₀₄ ),- A group represented by S- (R ₉₀₅ ), a group represented by -N (R ₉₀₆ ) (R ₉₀₇ ), a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted aryl group. It is a heterocyclic group having 5 to 50 ring-forming atoms.
(Iv) R ₁₂₁ to R ₁₂₇ are hydrogen atoms, and R ₁₁ is a substituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group. )

For example, in the compound represented by the general formula (11), when Ar ₃ is a group represented by the general formula (1c), the compound according to the present embodiment is represented by the following general formula (11c). To.

(R ₁₁ in the general formula (11c) is
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L _11, m, X, and _R 101 _{~ R 107} are each, the _L 11 in the general formula (1), m, has the same meaning X, and the _R 101 _{~ R 107,}
R ₁₃₁ to R ₁₃₇ are independently synonymous with R ₁₃₁ to R ₁₃₇ in the general formula (1c). )

The compound represented by the general formula (11c) is represented by the following general formula (111c) when m is 0.

(R ₁₁ in the general formula (111c) is
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
_X, _R 101 _~ R _{_107,} and _R 131 _{~ R 137} are each, _X in the general formula _{_{(1), R 101 ~ R}} 107, and is synonymous with _{_R} 131 _~ _R _137. )

In the compound represented by the general formula (11c), when m is 1, the compound according to the present embodiment is represented by the following general formula (112c).
In the compound represented by the general formula (11c), when m is 2, the compound according to the present embodiment is represented by the following general formula (113c).

(R ₁₁ in the general formulas (112c) and (113c) are independent of each other.
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L ₁₁ , L _113, and L ₁₁₄ are independently substituted or unsubstituted ring-forming arylene groups having 6 to 13 carbon atoms, respectively.
The set consisting of L ₁₁₃ and L ₁₁₄ is
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
X and R ₁₀₁ to R ₁₀₇ are synonymous with X and R ₁₀₁ to R ₁₀₇ in the general formula (1), respectively.
R ₁₃₁ to R ₁₃₇ are independently synonymous with R ₁₃₁ to R ₁₃₇ in the general formula (1c).
However, at least one of R ₁₃₁ to R ₁₃₇ is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted ring-forming carbon number. 3 to 50 cycloalkyl groups, cyano groups, halogen atoms, groups represented by -Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ), groups represented by -O- (R ₉₀₄ ), -S- Group represented by (R ₉₀₅ ), group represented by -N (R ₉₀₆ ) (R ₉₀₇ ), substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or substituted or unsubstituted ring formation. It is a heterocyclic group having 5 to 50 atoms, and R ₉₀₁ to R ₉₀₇ are independently synonymous with R ₉₀₁ to R ₉₀₇ in the general formula (1a). )

In the compound according to the present embodiment, Ar ₃ is preferably a group represented by the general formula (1d) or a substituted or unsubstituted heterocyclic group having 5 to 16 ring-forming atoms.

For example, in the compound represented by the general formula (11), when Ar ₃ is a group represented by the general formula (1d), the compound according to the present embodiment is represented by the following general formula (11d). To.

(R ₁₁ in the general formula (11d) is
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L _11, m, X, and _R 101 _{~ R 107} are each, the _L 11 in the general formula (1), m, has the same meaning X, and the _R 101 _{~ R 107,}
L ₁₂ and HAR are synonymous with L ₁₂ and HAR in the general formula (1d). )

When m is 0 in the compound represented by the general formula (11d), the compound according to the present embodiment is represented by the following general formula (111d).

(R ₁₁ in the general formula (111d) is
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
X and R ₁₀₁ to R ₁₀₇ are synonymous with X and R ₁₀₁ to R ₁₀₇ in the general formula (1), respectively.
L ₁₂ is a substituted or unsubstituted ring-forming carbon number 6 to 13 arylene group.
HAR is a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. )

In the compound represented by the general formula (11d), when m is 1, the compound according to the present embodiment is represented by the following general formula (112d).
In the compound represented by the general formula (11d), when m is 2, the compound according to the present embodiment is represented by the following general formula (113d).

(R ₁₁ in the general formulas (112d) and (113d) are independent of each other.
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L ₁₁ , L ₁₁₅ and L ₁₁₆ are independently substituted or unsubstituted ring-forming arylene groups having 6 to 13 carbon atoms, respectively.
The set consisting of L ₁₁₅ and L ₁₁₆ is
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
X and R ₁₀₁ to R ₁₀₇ are synonymous with X and R ₁₀₁ to R ₁₀₇ in the general formula (1), respectively.
L ₁₂ is a substituted or unsubstituted ring-forming carbon number 6 to 13 arylene group.
HAR is a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. )

In the compound represented by the general formula (11), when Ar ₃ is a substituted or unsubstituted heterocyclic group having 5 to 16 ring-forming atoms, the compound according to the present embodiment has the following general formula (11f). It is represented by.

(In the general formula (11f),
Ar ₃ is a substituted or unsubstituted heterocyclic group having 5 to 16 ring-forming atoms.
R ₁₁ are independent of each other
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L ₁₁ is a substituted or unsubstituted ring-forming carbon number 6 to 13 arylene group.
X and R ₁₀₁ to R ₁₀₇ are synonymous with X and R ₁₀₁ to R ₁₀₇ in the general formula (1), respectively. )

In the general formula (11f), Ar ₃ as a heterocyclic group is preferably a group represented by the following general formulas (111 g), (112 g), (113 g) or (114 g).

(In the general formulas (111 g), (112 g), (113 g) and (114 g), R ₁₄₁ to R ₁₄₈ are independently hydrogen atoms, substituted or unsubstituted alkyl groups having 1 to 50 carbon atoms, respectively. Substituent or unsubstituted haloalkyl group having 1 to 50 carbon atoms, substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms, cyano group, halogen atom, -Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ) ), The group represented by -O- (R ₉₀₄ ), the group represented by -S- (R ₉₀₅ ), the group represented by -N (R ₉₀₆ ) (R ₉₀₇ ), the substitution. Alternatively, it is an aryl group having an unsubstituted ring-forming carbon number of 6 to 50, or a heterocyclic group having a substituted or unsubstituted ring-forming atom number of 5 to 50, and R ₉₀₁ to R ₉₀₇ are independently expressed in the above general formula ( Synonymous with R ₉₀₁ to R ₉₀₇ in 1a), X ₂ is an oxygen atom or a sulfur atom. * In the general formulas (111 g), (112 g), (113 g) and (114 g) is an anthracene ring. Indicates the connection position of.)

In the compound represented by the general formula (11f), when Ar ₃ is a group represented by the general formula (111 g), the compound according to the present embodiment is represented by the following general formula (11 g).

(In the general formula (11 g),
R ₁₁ are independent of each other
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L ₁₁ is a substituted or unsubstituted ring-forming carbon number 6 to 13 arylene group.
X ₁ and X ₂ are independently synonymous with X in the general formula (1).
R ₁₀₁ to R ₁₀₇ are independently synonymous with R ₁₀₁ to R ₁₀₇ in the general formula (1).
R ₁₄₁ to R ₁₄₆ and R ₁₄₈ are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Cyano group,
Halogen atom,
-A group represented by Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
A group represented by -O- (R ₉₀₄ ),
A group represented by -S- (R ₉₀₅ ),
A group represented by -N (R ₉₀₆ ) (R ₉₀₇ ),
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
R ₉₀₁ to R ₉₀₇ are independently synonymous with R ₉₀₁ to R ₉₀₇ in the general formula (1). )

In the compound according to the present embodiment, at least one of R ₁₁ to R ₁₈ is preferably a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group, and is preferably an unsubstituted or unsubstituted phenyl group or no substituent. More preferably, it is a substituted biphenyl group.

In the compound according to the present embodiment, at least one of R ₁₁ to R ₁₈ is preferably a group represented by the following formulas (1e), (1f), (1g) or (1h).

(* In the formulas (1e), (1f), (1g) and (1h) indicates the bonding position with the anthracene ring.)

In the compound according to the present embodiment, the groups represented by the formulas (1e), (1f), (1g) and (1h) may have one or more substituents.

For example, when R ₁₁ is a group represented by the formula (1e), the compound represented by the general formula (11) is represented by the following general formula (11e).

_(L _11, in the general formula _{(11e) m, X, R} 101 ~ R 107, and Ar _3, respectively, wherein _L 11 in the general formula _{(1), m, X,} R 101 ~ R 107, and Ar _It is synonymous with _3. )

In the compound according to the present embodiment, L ₁₁ is preferably a substituted or unsubstituted phenylene group, m is 1, and L ₁₁ is more preferably a substituted or unsubstituted phenylene group.

In the compound according to the present embodiment, L ₁₁ is preferably a group represented by the following formula (100a) or (100b), m is 1, and L ₁₁ is the following formula (100a) or ( More preferably, it is a group represented by 100b).

(Of the two * in the formulas (100a) and (100b), one * indicates the bonding position with the anthracene ring, and the other * is the fused ring containing X in the general formula (1). Indicates the connection position of.)

For example, when m is 1 and L ₁₁ is a group represented by the formula (100a), the compound represented by the general formula (11) is represented by the following general formula (11L). ..

(R ₁₁ in the general formula (11L) is
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
X, R ₁₀₁ to R ₁₀₇ , and Ar ₃ in the general formula (11L) are synonymous with X, R ₁₀₁ to R ₁₀₇ , and Ar ₃ in the general formula (1), respectively. )

In the compound according to this embodiment, X is preferably an oxygen atom.

In the compound according to the present embodiment, R ₁₀₁ to R ₁₀₇ are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Substituent or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
Cyano group,
It is preferably a halogen atom or a group represented by −Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ).
In the compound according to the present embodiment, R ₁₀₁ to R ₁₀₇ are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Cyano group,
It is also preferable that it is a halogen atom or a group represented by −Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ).

In the compound according to the present embodiment, R ₁₀₁ to R ₁₀₇ are also preferably hydrogen atoms.
Further, in the compound according to the present embodiment, at least one of R ₁₀₁ to R ₁₀₇ is
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Substituent or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
Cyano group,
It is also preferable that it is a halogen atom or a group represented by −Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ).
Further, in the compound according to the present embodiment, it is also preferable that at least one of R ₁₀₁ to R ₁₀₇ is an unsubstituted aryl group having 6 to 12 carbon atoms.

-Method for producing a compound according to the present embodiment For the compound according to the present embodiment, a known alternative reaction and raw material suitable for the target product are used according to or following the synthesis example described in the section of Examples described later. It can be manufactured by using it.

-Specific Examples of Compounds According to This Embodiment Specific examples of the compounds according to this embodiment include the following compounds. However, the present invention is not limited to specific examples of these compounds.

According to the compound according to the present embodiment, the driving voltage of the organic electroluminescence device can be reduced. According to one aspect of the compound according to the present embodiment, the driving voltage can be lowered while maintaining the luminous efficiency of the organic electroluminescence device.

The above is the description of the compound according to the first embodiment.

[Second Embodiment]
(Organic electroluminescence element)
The organic EL device according to the second embodiment of the present invention will be described.
The organic EL device according to the present embodiment includes an organic layer between both electrodes of the anode and the cathode. This organic layer contains at least one layer composed of an organic compound. Alternatively, this organic layer is formed by laminating a plurality of layers composed of organic compounds. The organic layer may further contain an inorganic compound.

The organic EL device according to this embodiment has a first organic layer as an organic layer. The first organic layer contains the compound according to the first embodiment (the compound represented by the general formula (1) or the like).

In the organic EL device of the present embodiment, at least one of the organic layers is a light emitting layer. The organic layer may be composed of, for example, one light emitting layer, or may include a layer that can be adopted for an organic EL element. The layer that can be adopted for the organic EL device is not particularly limited, but is at least one selected from the group consisting of, for example, a hole injection layer, a hole transport layer, an electron injection layer, an electron transport layer, and a barrier layer. Layers are mentioned.

In the organic EL element according to the present embodiment, it is preferable that the first organic layer is a light emitting layer. The organic EL device according to the present embodiment has a light emitting layer included between the anode and the cathode. Even when the light emitting layer contains the compound according to the first embodiment, the organic layer other than the light emitting layer may contain the compound according to the first embodiment.

FIG. 1 shows a schematic configuration of an example of an organic EL device according to the present embodiment.
The organic EL element 1 includes a translucent substrate 2, an anode 3, a cathode 4, and an organic layer 10 arranged between the anode 3 and the cathode 4. The organic layer 10 is composed of a hole injection layer 6, a hole transport layer 7, a light emitting layer 5, an electron transport layer 8, and an electron injection layer 9 laminated in this order from the anode 3 side.
The present invention is not limited to the configuration of the organic EL element shown in FIG.

(First compound)
The first compound (compound according to the first embodiment) contained in the first organic layer of the organic EL device according to the present embodiment has the above-mentioned general formula (the compound according to the first embodiment) according to the characteristics required for the contained layer. It is appropriately selected from the compounds included in the range of compounds represented by 1).

(Second compound)
The first organic layer of the organic EL device according to the present embodiment preferably contains a first compound and a second compound, and the first organic layer as a light emitting layer is the first compound and It is more preferable to contain a second compound. In this embodiment, the second compound is preferably a dopant material (sometimes referred to as a guest material, emitter or luminescent material) and the first compound is sometimes referred to as a host material (sometimes referred to as a matrix material). .) Is preferable.

The second compound is preferably a fluorescent compound. A fluorescent compound is a compound capable of emitting light from a singlet excited state.

As the blue fluorescent light emitting material that can be used in the light emitting layer as the second compound, a pyrene derivative, a styrylamine derivative, a chrysene derivative, a fluoranthene derivative, a fluorene derivative, a triarylamine derivative or the like can be used. Specifically, N, N'-bis [4- (9H-carbazole-9-yl) phenyl] -N, N'-diphenylstylben-4,4'-diamine (abbreviation: YGA2S), 4- (9H) -Carbazole-9-yl) -4'-(10-Phenyl-9-anthryl) Triphenylamine (abbreviation: YGAPA), 4- (10-Phenyl-9-anthryl) -4'-(9-phenyl-9H) -Carbazole-3-yl) Triphenylamine (abbreviation: PCBAPA) and the like can be mentioned.

-Compound represented by the general formula (2) The second compound is preferably a compound represented by the following general formula (2).

(In the general formula (2),
One or more of the two or more adjacent pairs of R ₂₁ to R ₂₆
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
One or more of the two or more adjacent pairs of R ₂₇ to R ₃₀
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
One or more of two or more adjacent pairs of R ₂₀₁ to R ₂₀₅
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
One or more of two or more adjacent pairs of R ₂₀₆ to R ₂₁₀
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
R ₂₁ to R ₂₆ , R ₂₇ to R ₃₀ , R ₂₀₁ to R _205, and R ₂₀₆ to R ₂₁₀ , which do not form the monocyclic ring and do not form the condensed ring, are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Cyano group,
Halogen atom,
-A group represented by Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
A group represented by -O- (R ₉₀₄ ),
A group represented by -S- (R ₉₀₅ ),
A group represented by -N (R ₉₀₆ ) (R ₉₀₇ ),
Substituent or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
Substituted or unsubstituted ring-forming heterocyclic groups having 5 to 50 atoms,
Substituted or unsubstituted phosphanyl groups,
Substituted or unsubstituted phosphoryl groups,
Substituent or unsubstituted ring-forming arylcarbonyl group having 6 to 30 carbon atoms,
It is a nitro group or a carboxy group,
R ₉₀₁ , R ₉₀₂ , R ₉₀₃ , R ₉₀₄ , R ₉₀₅ , R ₉₀₆ and R ₉₀₇ are independent of each other.
Substituent or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
Substituted or unsubstituted ring-forming heterocyclic groups having 5 to 50 atoms,
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms. )

One or more pairs of two or more adjacent pairs of R ₂₁ to R ₂₆ ,
One or more pairs of two or more adjacent pairs of R ₂₇ to R ₃₀
At least one set of one or more pairs of two or more adjacent pairs of R ₂₀₁ to R ₂₀₅ and one or more pairs of two or more adjacent pairs of R ₂₀₆ to R ₂₁₀
They combine with each other to form a substituted or unsubstituted monocyclic ring, or they combine with each other to form a substituted or unsubstituted fused ring.

In one embodiment, two or more of R ₂₈ to R ₃₀ in the general formula (2) are bonded to each other to form a substituted or unsubstituted monocyclic or condensed ring having 3 to 30 ring-forming atoms. Form.

For example, as an example of the case where adjacent pairs of R ₂₈ , R _29, and R _{30 of} R ₂₇ to R ₃₀ are bonded to each other to form a fused ring, it is represented by the following general formula (21). Examples include compounds.

In the general formula (21),
One or more of the two or more adjacent pairs of R ₂₁ to R ₂₆
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
One or more of two or more adjacent pairs of R ₂₀₁ to R ₂₀₅
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
One or more of two or more adjacent pairs of R ₂₀₆ to R ₂₁₀
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
R ₂₁ to R ₂₆ , R ₂₇ , R ₂₀₁ to R _205, and R ₂₀₆ to R ₂₁₀ , which do not form the monocyclic ring and do not form the condensed ring, are independently described in the general formula (2). It is synonymous with R ₂₁ to R ₂₆ , R ₂₇ , R ₂₀₁ to R _205, and R ₂₀₆ to R _210, which do not form a single ring and do not form the condensed ring.
R ₂₁₁ to R ₂₁₇ are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Cyano group,
Halogen atom,
-A group represented by Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
A group represented by -O- (R ₉₀₄ ),
A group represented by -S- (R ₉₀₅ ),
A group represented by -N (R ₉₀₆ ) (R ₉₀₇ ),
Substituent or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
Substituted or unsubstituted ring-forming heterocyclic groups having 5 to 50 atoms,
Substituted or unsubstituted phosphanyl groups,
Substituted or unsubstituted phosphoryl groups,
Substituent or unsubstituted ring-forming arylcarbonyl group having 6 to 30 carbon atoms,
It is a nitro group or a carboxy group,
R ₉₀₁ , R ₉₀₂ , R ₉₀₃ , R ₉₀₄ , R ₉₀₅ , R ₉₀₆ and R ₉₀₇ are independent of each other.
Substituent or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
Substituted or unsubstituted ring-forming heterocyclic groups having 5 to 50 atoms,
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms. )

The compound represented by the general formula (21) is preferably represented by the following general formula (21a).

(In the general formula (21a),
One or more of the two or more adjacent pairs of R ₂₁ to R ₂₆
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
R ₂₁ to R ₂₆ and R ₂₇ , which do not form the monocyclic ring and do not form the condensed ring, independently do not form the monocyclic ring in the general formula (2) and form the condensed ring. It is synonymous with R ₂₁ to R ₂₆ and R ₂₇ that do not form. )

Further, for example, a pair consisting of adjacent R ₂₂ and R _{23 of} R ₂₁ to R ₂₆ is coupled to each other to form a single ring, and a pair consisting of R ₂₄ and R ₂₅ is further coupled to each other to form a single ring. As an example of the case of forming a ring, a compound represented by the following general formula (22) can be mentioned.

(In the general formula (22),
One or more of the two or more adjacent pairs of R ₂₇ to R ₃₀
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
One or more of two or more adjacent pairs of R ₂₀₁ to R ₂₀₅
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
One or more of two or more adjacent pairs of R ₂₀₆ to R ₂₁₀
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
R ₂₁ , R ₂₆ , R ₂₇ to R ₃₀ , R ₂₀₁ to R _205, and R ₂₀₆ to R ₂₁₀ , which do not form the monocyclic ring and do not form the condensed ring, are independently represented by the general formula (2). ), _Which is synonymous with R ₂₁ , R ₂₆ , R ₂₇ to R ₃₀ , R ₂₀₁ to R _205, and R ₂₀₆ to R _210, which do not form the monocyclic ring and do not form the condensed ring.
_R218 to _R225 are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Cyano group,
Halogen atom,
-A group represented by Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
A group represented by -O- (R ₉₀₄ ),
A group represented by -S- (R ₉₀₅ ),
A group represented by -N (R ₉₀₆ ) (R ₉₀₇ ),
Substituent or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
Substituted or unsubstituted ring-forming heterocyclic groups having 5 to 50 atoms,
Substituted or unsubstituted phosphanyl groups,
Substituted or unsubstituted phosphoryl groups,
Substituent or unsubstituted ring-forming arylcarbonyl group having 6 to 30 carbon atoms,
It is a nitro group or a carboxy group,
R ₉₀₁ , R ₉₀₂ , R ₉₀₃ , R ₉₀₄ , R ₉₀₅ , R ₉₀₆ and R ₉₀₇ are independent of each other.
Substituent or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
Substituted or unsubstituted ring-forming heterocyclic groups having 5 to 50 atoms,
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms. )

In one embodiment, R ₂₂ and R ₂₃ in the general formula (2) are bonded to each other to form a substituted or unsubstituted monocyclic or condensed ring having 3 to 30 ring-forming atoms.

In one embodiment, the compound represented by the general formula (2) is a compound represented by the following general formula (23).

(In the general formula (23),
One or more of the two or more adjacent pairs of R ₂₄ to R ₂₆
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
One or more of the two or more adjacent pairs of R ₂₇ to R ₃₀
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
One or more of two or more adjacent pairs of R ₂₀₁ to R ₂₀₅
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
One or more of two or more adjacent pairs of R ₂₀₆ to R ₂₁₀
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
R ₂₁ , R ₂₄ to R ₂₆ , R ₂₇ to R ₃₀ , R ₂₀₁ to R _205, and R ₂₀₆ to R ₂₁₀ , which do not form the monocyclic ring and do not form the condensed ring, are independently described in general. It is synonymous with R ₂₁ , R ₂₄ to R ₂₆ , R ₂₇ to R ₃₀ , R ₂₀₁ to R _205, and R ₂₀₆ to R _210, which do not form the monocyclic ring and do not form the condensed ring in the formula (2). ,
_R226 to _R231 are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Cyano group,
Halogen atom,
-A group represented by Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
A group represented by -O- (R ₉₀₄ ),
A group represented by -S- (R ₉₀₅ ),
A group represented by -N (R ₉₀₆ ) (R ₉₀₇ ),
Substituent or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
Substituted or unsubstituted ring-forming heterocyclic groups having 5 to 50 atoms,
Substituted or unsubstituted phosphanyl groups,
Substituted or unsubstituted phosphoryl groups,
Substituent or unsubstituted ring-forming arylcarbonyl group having 6 to 30 carbon atoms,
It is a nitro group or a carboxy group,
_R232 and _R233 are independent of each other.
Hydrogen atom,
Unsubstituted alkyl groups with 1 to 50 carbon atoms,
An unsubstituted alkenyl group having 2 to 50 carbon atoms,
An unsubstituted alkynyl group having 2 to 50 carbon atoms,
Unsubstituted ring-forming cycloalkyl group with 3 to 50 carbon atoms,
-Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
-O- (R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom,
Cyano group,
Nitro group,
An unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or an unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
R ₉₀₁ , R ₉₀₂ , R ₉₀₃ , R ₉₀₄ , R ₉₀₅ , R ₉₀₆ and R ₉₀₇ are independent of each other.
Substituent or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
Substituted or unsubstituted ring-forming heterocyclic groups having 5 to 50 atoms,
It is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms. )

In each of the general formulas (2), (21), (21a), (22) and (23),
If R ₉₀₁ is plural, _{R 901} may be identical to each other or different,
If R ₉₀₂ is plural, _{R 902} may be identical to each other or different,
If R ₉₀₃ is plural, _{R 903} may be identical to each other or different,
If R ₉₀₄ is plural, _{R 904} may be identical to each other or different,
If R ₉₀₅ is plural, _{R 905} may be identical to each other or different,
When there are multiple R- _906s , the plurality of R- _906s are the same as or different from each other.
If R ₉₀₇ is plural, _{R 907} may be identical to one another or different.

In one embodiment, R ₂₁ to R ₃₀ and R ₂₀₁ to R ₂₁₀ , which do not form the monocyclic ring and do not form the condensed ring in the general formula (2), are independent of each other.
Hydrogen atom,
Unsubstituted alkyl groups with 1 to 50 carbon atoms,
Cyano group,
Halogen atom,
An unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or an unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.

In one embodiment, R ₂₁ to R ₃₀ and R ₂₀₁ to R ₂₁₀ , which do not form the monocyclic ring and do not form the condensed ring in the general formula (2), are independent of each other.
Hydrogen atom,
An unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or an unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.

In one embodiment, one of R ₂₃ and R ₂₄ in the general formulas (21) and (21a) is an aryl group having an unsubstituted ring-forming carbon number of 6 to 50, or an unsubstituted ring-forming atom number of 5 to 5. It is a heterocyclic group of 50, and the other of R ₂₃ and R ₂₄ is a hydrogen atom.

In one embodiment, one of R ₂₃ and R ₂₄ in the general formulas (21) and (21a) is an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms, and the other of R ₂₃ and R ₂₄ . Is a hydrogen atom.

In one embodiment, one of R ₂₃ and R ₂₄ in the general formulas (21) and (21a) is a dibenzofuranyl group or a dibenzothiophenyl group, and the other of R ₂₃ and R ₂₄ is a hydrogen atom. is there.

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

-Compound represented by the general formula (5) The second compound is preferably a compound represented by the following general formula (5).

(In the general formula (5),
One or more of the two or more adjacent pairs of R ₅₀₁ to R ₅₀₇ and R ₅₁₁ to R ₅₁₇
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
R ₅₀₁ to R ₅₀₇ and R ₅₁₁ to R ₅₁₇ , which do not form the monocyclic ring and do not form the condensed ring, are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
-A group represented by Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
A group represented by -O- (R ₉₀₄ ),
A group represented by -S- (R ₉₀₅ ),
A group represented by -N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom,
Cyano group,
Nitro group,
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
R ₅₂₁ and R ₅₂₂ are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
-A group represented by Si (R ₉₀₁ ) (R ₉₀₂ ) (R ₉₀₃ ),
A group represented by -O- (R ₉₀₄ ),
A group represented by -S- (R ₉₀₅ ),
A group represented by -N (R ₉₀₆ ) (R ₉₀₇ ),
Halogen atom,
Cyano group,
Nitro group,
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms. )

"One set of two or more adjacent sets of R ₅₀₁ to R ₅₀₇ and R ₅₁₁ to R ₅₁₇ " is, for example, a set of R ₅₀₁ and R ₅₀₂ , a set of R ₅₀₂ and R ₅₀₃ , and R. It is a combination of a set of ₅₀₃ and R ₅₀₄ , a set of R ₅₀₅ and R ₅₀₆ , a set of R ₅₀₆ and R ₅₀₇ , a set of R ₅₀₁ , R ₅₀₂ and R ₅₀₃ , and the like.

In one embodiment, at least one, preferably two, of R ₅₀₁ to R ₅₀₇ and R ₅₁₁ to R ₅₁₇ are groups represented by -N (R ₉₀₆ ) (R ₉₀₇ ).

In one embodiment, R ₅₀₁ to R ₅₀₇ and R ₅₁₁ to R ₅₁₇ are independent of each other.
Hydrogen atom,
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.

In one embodiment, the compound represented by the general formula (5) is a compound represented by the following general formula (52).

(In the general formula (52),
One or more of the two or more adjacent pairs of R ₅₃₁ to R ₅₃₄ and R ₅₄₁ to R ₅₄₄
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
R ₅₃₁ to R ₅₃₄ , R ₅₄₁ to R ₅₄₄ , and R ₅₅₁ and R ₅₅₂ , which do not form the monocyclic ring and do not form the condensed ring, are independent of each other.
Hydrogen atom,
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
R ₅₆₁ to R ₅₆₄ are independent of each other.
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms. )

In one embodiment, the compound represented by the general formula (5) is a compound represented by the following general formula (53).

(In the general formula (53), R ₅₅₁ , R ₅₅₂ and R ₅₆₁ to R ₅₆₄ are independently synonymous with R ₅₅₁ , R ₅₅₂ and R ₅₆₁ to R ₅₆₄ in the general formula (52), respectively.)

In one embodiment, R ₅₆₁ to R ₅₆₄ in the general formula (52) and the general formula (53) are independently substituted or unsubstituted aryl groups having 6 to 50 carbon atoms (preferably phenyl groups). ).

In one embodiment, R ₅₂₁ and R ₅₂₂ in the general formula (5) and R ₅₅₁ and R ₅₅₂ in the general formula (52) and the general formula (53) are hydrogen atoms.

In one embodiment, the substituent in the case of "substituted or unsubstituted" in the general formula (5), general formula (52) and general formula (53) is
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituent or unsubstituted alkenyl groups having 2 to 50 carbon atoms,
Substituent or unsubstituted alkynyl groups having 2 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.

(Specific example of the compound represented by the general formula (5))
Specific examples of the compound represented by the general formula (5) include the compounds shown below.

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

<Relationship between the first compound and the second compound in the light emitting layer>
In the organic EL device according to this embodiment, if the first organic layer as the light emitting layer contains a second compound and the first compound, the first compound singlet energy S ₁ and _(H), the second It is preferable that the singlet energy S ₁ (D) of the compound of the above compound satisfies the relationship of the following mathematical formula (Equation 1).
S ₁ (H)> S ₁ (D) ... (Equation 1)

(Singlet energy S ₁ )
The method of measuring the solution using a singlet energy S ₁ (hereinafter sometimes referred to as solution method.), A method described below.
A 10 μmol / L toluene solution of the compound to be measured is prepared, placed in a quartz cell, and the absorption spectrum (vertical axis: absorption intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300 K). A tangent line is drawn for the fall on the long wavelength side of this absorption spectrum, and the wavelength value λedge [nm] at the intersection of the tangent line and the horizontal axis is substituted into the conversion formula (F2) shown below to calculate the singlet energy. To do.
Conversion formula (F2): S ₁ [eV] = 1239.85 / λedge
Examples of the absorption spectrum measuring device include, but are not limited to, a spectrophotometer (device name: U3310) manufactured by Hitachi, Ltd.

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

When the light emitting layer contains the first compound, it is preferable that the light emitting layer does not contain a phosphorescent material (dopant material).
When the light emitting layer contains the first compound, it is preferable that the light emitting layer does not contain a heavy metal complex and a phosphorescent rare earth metal complex. Here, examples of the heavy metal complex include an iridium complex, an osmium complex, a platinum complex, and the like.
Further, when the light emitting layer contains the first compound, it is also preferable that the light emitting layer does not contain a metal complex.

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

(Compound content in the light emitting layer)
When the light emitting layer contains the first compound and the second compound, the contents of the first compound and the second compound in the light emitting layer are preferably in the following ranges, for example, respectively.
The content of the first compound is preferably 80% by mass or more and 99% by mass or less, more preferably 90% by mass or more and 99% by mass or less, and preferably 95% by mass or more and 99% by mass or less. More preferred.
The content of the second compound is preferably 1% by mass or more and 10% by mass or less, more preferably 1% by mass or more and 7% by mass or less, and preferably 1% by mass or more and 5% by mass or less. More preferred.
However, the upper limit of the total content of the first compound and the second compound in the light emitting layer is 100% by mass.

In addition, this embodiment does not exclude that the light emitting layer contains a material other than the first compound and the second compound.
The light emitting layer may contain only one type of the first compound, or may contain two or more types. The light emitting layer may contain only one type of the second compound, or may contain two or more types.

The configuration of the organic EL element according to this embodiment will be further described. Hereinafter, the description of the reference numeral may be omitted.

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

(anode)
For the anode formed on the substrate, it is preferable to use a metal having a large work function (specifically, 4.0 eV or more), an alloy, an electrically conductive compound, a mixture thereof, or the like. Specifically, for example, indium tin oxide (ITO: Indium Tin Oxide), indium tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, tungsten oxide, and indium oxide containing zinc oxide. , Graphene and the like. In addition, gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium ( Pd), titanium (Ti), nitrides of metallic materials (for example, titanium nitride) and the like can be mentioned.

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

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

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

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

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

By providing the electron injection layer, a cathode is formed by using various conductive materials such as indium tin oxide containing Al, Ag, ITO, graphene, silicon or silicon oxide, regardless of the size of the work function. can do. These conductive materials can be formed into a film by using a sputtering method, an inkjet method, a spin coating method, or the like.

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

In addition, as a substance having high hole injection property, a low molecular weight organic compound 4,4', 4''-tris (N, N-diphenylamino) triphenylamine (abbreviation: TDATA), 4,4' , 4''-Tris [N- (3-Methylphenyl) -N-Phenylamino] triphenylamine (abbreviation: MTDATA), 4,4'-bis [N- (4-diphenylaminophenyl) -N-phenyl Amino] Biphenyl (abbreviation: DPAB), 4,4'-bis (N- {4- [N'-(3-methylphenyl) -N'-phenylamino] phenyl} -N-phenylamino) Biphenyl (abbreviation:: DNTPD), 1,3,5-tris [N- (4-diphenylaminophenyl) -N-phenylamino] benzene (abbreviation: DPA3B), 3- [N- (9-phenylcarbazole-3-yl) -N -Phenylamino] -9-Phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis [N- (9-phenylcarbazole-3-yl) -N-phenylamino] -9-phenylcarbazole (abbreviation: PCzPCA2), Aromatic amine compounds such as 3- [N- (1-naphthyl) -N- (9-phenylcarbazole-3-yl) amino] -9-phenylcarbazole (abbreviation: PCzPCN1) and dipyrazino [2,3-f : 20,30-h] Kinoxalin-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) can also be mentioned.

Further, as a substance having high hole injection property, a polymer compound (oligomer, dendrimer, polymer, etc.) can also be used. For example, poly (N-vinylcarbazole) (abbreviation: PVK), poly (4-vinyltriphenylamine) (abbreviation: PVTPA), poly [N- (4- {N'- [4- (4-diphenylamino)). Phenyl] phenyl-N'-phenylamino} phenyl) methacrylamide] (abbreviation: PTPDMA), poly [N, N'-bis (4-butylphenyl) -N, N'-bis (phenyl) benzidine] (abbreviation: Polymer compounds such as Poly-TPD) can be mentioned. Further, a polymer compound to which an acid such as poly (3,4-ethylenedioxythiophene) / poly (styrene sulfonic acid) (PEDOT / PSS) or polyaniline / poly (styrene sulfonic acid) (Pani / PSS) is added is used. You can also do it.

(Hole transport layer)
The hole transport layer is a layer containing a substance having a high hole transport property. An aromatic amine compound, a carbazole derivative, an anthracene derivative, or the like can be used for the hole transport layer. Specifically, 4,4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (abbreviation: NPB) and N, N'-bis (3-methylphenyl) -N, N'- Diphenyl- [1,1'-biphenyl] -4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl) triphenylamine (abbreviation: BAFLP), 4 , 4'-bis [N- (9,9-dimethylfluoren-2-yl) -N-phenylamino] biphenyl (abbreviation: DFLDPBi), 4,4', 4''-tris (N, N-diphenylamino) ) Triphenylamine (abbreviation: TDATA), 4,4', 4''-tris [N- (3-methylphenyl) -N-phenylamino] triphenylamine (abbreviation: MTDATA), 4,4'-bis [N- (Spiro-9,9'-bifluoren-2-yl) -N-phenylamino] Aromatic amine compounds such as biphenyl (abbreviation: BSBP) can be used. The substances described here are mainly substances having a hole mobility of ^10-6 cm ² / (V · s) or more.

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

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

When two or more hole transport layers are arranged, it is preferable to arrange a material having a larger energy gap closer to the light emitting layer. Examples of such a material include HT2 used in the examples described later.

(Electronic transport layer)
The electron transport layer is a layer containing a substance having a high electron transport property. The electron transport layer includes 1) metal complexes such as aluminum complexes, beryllium complexes and zinc complexes, 2) complex aromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives and phenanthroline derivatives, and 3) polymer compounds. Can be used. Specifically, as low-molecular-weight organic compounds, Alq, tris (4-methyl-8-quinolinolato) aluminum (abbreviation: Almq ₃ ), bis (10-hydroxybenzo [h] quinolinato) beryllium (abbreviation: BeBq ₂ ), Metal complexes such as BAlq, Znq, ZnPBO, and ZnBTZ can be used. In addition to the metal complex, 2- (4-biphenylyl) -5- (4-tert-butylphenyl) -1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis [5- (Phenyl-butylphenyl) -1,3,4-oxadiazole-2-yl] benzene (abbreviation: OXD-7), 3- (4-tert-butylphenyl) -4-phenyl-5- (4-) Biphenylyl) -1,2,4-triazole (abbreviation: TAZ), 3- (4-tert-butylphenyl) -4- (4-ethylphenyl) -5- (4-biphenylyl) -1,2,4- Complexes such as triazole (abbreviation: p-EtTAZ), vasofenantroline (abbreviation: BPhen), vasocuproin (abbreviation: BCP), 4,4'-bis (5-methylbenzoxadiazole-2-yl) stilben (abbreviation: BzOs) Aromatic compounds can also be used. In this embodiment, a benzimidazole compound can be preferably used. The substances described here are mainly substances having electron mobility of ^10-6 cm ² / (V · s) or more. A substance other than the above may be used as the electron transport layer as long as it is a substance having higher electron transport property than hole transport property. Further, the electron transport layer may be composed of a single layer, or may be composed of two or more layers made of the above substances.

Further, a polymer compound can be used for the electron transport layer. For example, poly [(9,9-dihexylfluorene-2,7-diyl) -co- (pyridine-3,5-diyl)] (abbreviation: PF-Py), poly [(9,9-dioctylfluorene-2) , 7-diyl) -co- (2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy) and the like can be used.

(Electron injection layer)
The electron injection layer is a layer containing a substance having a high electron injection property. The electron injection layer includes lithium (Li), cesium (Cs), calcium (Ca), lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF ₂ ), lithium oxide (LiOx), etc. Alkaline metals such as, alkaline earth metals, or compounds thereof can be used. In addition, a substance having an electron transporting property containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a substance containing magnesium (Mg) in Alq or the like may be used. In this case, electron injection from the cathode can be performed more efficiently.

Alternatively, a composite material obtained by mixing an organic compound and an electron donor (donor) may be used for the electron injection layer. Such a composite material is excellent in electron injection property and electron transport property because electrons are generated in the organic compound by the electron donor. In this case, the organic compound is preferably a material excellent in transporting generated electrons, and specifically, for example, a substance (metal complex, complex aromatic compound, etc.) constituting the above-mentioned electron transport layer is used. be able to. The electron donor may be any substance that exhibits electron donating property to the organic compound. Specifically, alkali metals, alkaline earth metals and rare earth metals are preferable, and lithium, cesium, magnesium, calcium, erbium, ytterbium and the like can be mentioned. Further, alkali metal oxides and alkaline earth metal oxides are preferable, and lithium oxides, calcium oxides, barium oxides and the like can be mentioned. A Lewis base such as magnesium oxide can also be used. Further, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.

(Layer formation method)
The method for forming each layer of the organic EL element of the present embodiment is not limited except as specifically mentioned above, but is limited to dry film deposition methods such as vacuum deposition method, sputtering method, plasma method, ion plating method, and spin coating. Known methods such as a coating method, a dipping method, a flow coating method, and a wet film forming method such as an inkjet method can be adopted.

(Film thickness)
The film thickness of each organic layer of the organic EL device of the present embodiment is not limited unless otherwise specified above. In general, if the film thickness is too thin, defects such as pinholes are likely to occur, and if the film thickness is too thick, a high applied voltage is required and efficiency is deteriorated. Therefore, the film thickness of each organic layer of an organic EL element is usually several. The range from nm to 1 μm is preferable.

(Electronics)
It is preferable that the electronic device according to the present embodiment is equipped with the organic EL element according to the present embodiment. Examples of electronic devices include display devices and light emitting devices.
Examples of the display device include display components (for example, organic EL panel modules, etc.), televisions, mobile phones, tablets, personal computers, and the like. Examples of the light emitting device include lighting and vehicle lighting equipment.

The organic electroluminescence element according to the present embodiment contains the compound according to the first embodiment (the compound represented by the general formula (1) or the like). Therefore, according to the organic electroluminescence device according to the present embodiment, the drive voltage can be lowered. Further, according to one aspect of the organic electroluminescence device according to the present embodiment, the driving voltage can be lowered while maintaining the luminous efficiency.

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

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

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

In addition, the specific structure, shape, etc. in the practice of the present invention may be other structures, etc. as long as the object of the present invention can be achieved.

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

<Compound>
The compounds represented by the general formula (1) used in Examples 1 to 13 below are shown below.

The compounds used in Comparative Examples 1 to 4 below are shown below.

The structures of other compounds used in the production of the organic EL devices according to Examples 1 to 13 and Comparative Examples 1 to 4 are shown below.

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

[Example 1]
A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) having a thickness of 25 mm × 75 mm × 1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes, and then UV ozone cleaning was performed for 1 minute. The film thickness of ITO was 130 nm.
The glass substrate with the transparent electrode line after cleaning is mounted on the substrate holder of the vacuum vapor deposition apparatus, and the compound HA is co-deposited on the surface on the side where the transparent electrode line is formed so as to cover the transparent electrode. A hole injection layer having a thickness of 5 nm was formed.
Next, the compound HT1 was deposited on the hole injection layer to form a first hole transport layer having a film thickness of 80 nm.
Next, the compound HT2 was deposited on the first hole transport layer to form a second hole transport layer having a film thickness of 10 nm.
Next, the compound BH1 as the first compound and the compound BD as the second compound were co-deposited on the second hole transport layer to form a light emitting layer having a film thickness of 25 nm. The concentration of compound BH1 in the light emitting layer was 98% by mass, and the concentration of compound BD was 2% by mass.
Next, the compound HBL was deposited on the light emitting layer to form a hole barrier layer having a film thickness of 10 nm.
Next, the compound ET was vapor-deposited on the hole barrier layer to form an electron transport layer having a film thickness of 15 nm.
Next, lithium fluoride (LiF) was vapor-deposited on the electron transport layer to form an electron-injectable electrode (cathode) having a film thickness of 1 nm.
Then, metallic aluminum (Al) was vapor-deposited on the electron-injectable electrode to form a metallic Al cathode having a film thickness of 80 nm.
The element configuration of the organic EL element according to the first embodiment is shown as follows.
ITO (130) / HA (5) / HT1 (80) / HT2 (10) / BH1: BD (25,98%: 2%) / HBL (10) / ET (15) / LiF (1) / Al ( 80)
The numbers in parentheses indicate the film thickness (unit: nm).
Similarly, in parentheses, the percentage displayed number (98%: 2%) indicates the ratio (mass%) of compound BH1 and compound BD in the light emitting layer. Hereinafter, the same notation will be used.

[Examples 2 to 7]
The organic EL device according to Examples 2 to 7 was produced in the same manner as in Example 1 except that the compound BH1 in the light emitting layer of the organic EL device according to Example 1 was changed to the compound shown in Table 1.

[Examples 8 to 13]
The organic EL device according to Examples 8 to 13 was produced in the same manner as in Example 1 except that the compound BD in the light emitting layer of the organic EL device according to Example 1 was changed to the second compound shown in Table 2. did.

[Comparative Examples 1 and 2]
The organic EL device according to Comparative Examples 1 and 2 was produced in the same manner as in Example 1 except that the compound BH1 in the light emitting layer of the organic EL device according to Example 1 was changed to the compound shown in Table 1.

[Comparative Examples 3 to 4]
The organic EL device according to Comparative Examples 3 to 4 was produced in the same manner as in Example 1 except that the compound BD in the light emitting layer of the organic EL device according to Example 1 was changed to the second compound shown in Table 2. did.

<Evaluation of organic EL elements>
The organic EL devices manufactured in Examples 1 to 13 and Comparative Examples 1 to 4 were evaluated as follows. The evaluation results are shown in Tables 1 and 2.
In Tables 1 and 2, the compound Ref-1 used in the light emitting layers of Comparative Examples 1 and 3 and the compound Ref-2 used in the light emitting layers of Comparative Examples 2 and 4 are the first compounds for convenience. It is described in the column of the compound of.

・ External quantum efficiency EQE
The spectral radiance spectrum when a voltage was applied to the element so that the current density was 10 mA / cm ² was measured with a spectral radiance meter CS-2000 (manufactured by Konica Minolta Co., Ltd.). From the obtained spectral radiance spectrum, the external quantum efficiency EQE (unit:%) was calculated on the assumption that Lambasian radiation was performed.

-Drive voltage The voltage (unit: V) when energized between the anode (ITO transparent electrode) and the cathode (metal Al cathode) was measured so that the current density was 10 mA / cm ² .

According to the organic EL device according to Examples 1 to 7 using the compound represented by the general formula (1) as the first compound, the EQE equal to or higher than that of the organic EL device according to Comparative Examples 1 and 2 is maintained. However, the drive voltage could be lowered. In the compound Ref-1 used for the organic EL device according to Comparative Example 1, a substituent is bonded to the carbon atoms at the 9- and 10-positions of anthracene, and a hydrogen atom is bonded to the carbon atoms at the 1- to 8-positions. On the other hand, the compounds BH1 to BH7 used in the organic EL elements according to Examples 1 to 7 have substituents not only on the carbon atoms at the 9- and 10-positions of anthracene but also on the carbon atoms at the 2- and 3-positions. Are combined. Compounds in which three or more substituents are bonded to the anthracene ring, such as compounds BH1 to BH7, have a higher EQE of the organic EL element than compounds in which two substituents are bonded to the anthracene ring, such as compound Ref-1. It was possible to improve and lower the drive voltage. Further, although the compound Ref-2 used in Comparative Example 2 has a structure in which three substituents are bonded to the anthracene ring, the driving voltage is higher than that of Examples 1 to 7. If the substituent bonded to the carbon atom at the 2-position, 3-position, 9-position, and 10-position of anthracene is a substituent defined by the general formula (1) or the like, as in the compounds BH1 to BH7, the EQE is It was possible to further reduce the drive voltage while maintaining the same level as in Comparative Example 2.

The organic EL elements of Examples 8 to 13 had a lower voltage and higher efficiency than the organic EL elements of Comparative Examples 3 to 4.

<Compound synthesis>
(Synthesis Example 1) Synthesis of compound BH1

The synthesis scheme of compound BH1 is shown below.

(1-1) Synthesis of Compound BH-1-1 Under an argon atmosphere, 20.0 g (78.0 mmol) of 2-bromoanthracene, 10.4 g (86.0 mmol) of phenylboronic acid, Pd (PPh ₃ ) ₄ 1. 330 mL of DME and 55 mL of water were added to a 1 L flask containing 80 g (1.56 mmol) and 16.5 g (156 mmol) of Na ₂ CO ₃ , and the mixture was heated and stirred at about 80 ° C. for 7 hours. DME is an abbreviation for 1,2-dimethoxyethane.
After completion of the reaction, the mixture was cooled to room temperature, water was added to precipitate a solid, and the solid was collected by filtration. The solid collected by filtration was purified by silica gel column chromatography to obtain 19.7 g of a white solid. The obtained compound was subjected to FD-MS (Field Delivery Mass Spectrometery) analysis and identified as compound BH-1-1 (yield 70%).

(1-2) Synthesis of Compound BH-1-2 A solution prepared by dissolving 15.0 g (59.0 mmol) of Compound BH-1-1 in 680 mL of DMF was heated and stirred at about 80 ° C. To this, 10.5 g (59.0 mmol) of N-bromosuccinimide (NBS) dissolved in 1.18 L of DMF was added dropwise. DMF is an abbreviation for N, N-dimethylformamide.
After completion of the reaction, the mixture was cooled to room temperature, water was added to precipitate a solid, and the solid was collected by filtration. The collected solid was purified by silica gel column chromatography. The solid obtained by purification was recrystallized from toluene and further purified to obtain 10.8 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH-1-2 (yield 55%).

(1-3) Synthesis of compound BH-1-3 Under an argon atmosphere, compound BH-1-2 10.0 g (30.0 mmol), biphenylboronic acid 5.94 g (30.0 mmol), Pd (PPh ₃ ) ₄ 0.694 g (0.600 mmol), and _Na 2 _CO 3 6.36g DME129mL flask 1L containing the (60.0 mmol), and filled with water 21 mL, and 24 hours under heating and stirring at about 80 ° C..
After completion of the reaction, the mixture was cooled to room temperature, the reaction solution was transferred to a separating funnel, and the organic layer was extracted with toluene. The extracted organic layer was dried over sulfonyl ₄ , filtered, and the filtrate was concentrated to give a solid. The solid obtained by concentration was purified by silica gel column chromatography to obtain 9.15 g of a solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH-1-3 (yield 75%).

(1-4) Synthesis of Compound BH-1-4 A solution prepared by adding 394 mL of DMF to 8.00 g (19.7 mmol) of Compound BH-1- was dissolved by heating at about 50 ° C. and then cooled to room temperature. .. A DMF solution of 3.50 g (19.7 mmol) of N-bromosuccinimide (NBS) was added dropwise thereto, and the mixture was stirred at room temperature.
After completion of the reaction, the mixture was cooled to room temperature, water was added to precipitate a solid, and the solid was collected by filtration. The collected solid was purified by silica gel column chromatography. The solid obtained by purification was recrystallized from toluene and further purified to obtain 4.30 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH-1-4 (yield 45%).

(1-5) Synthesis of compound BH1 Under an argon atmosphere, compound BH-1-4 4.00 g (8.24 mmol), dibenzofuran-2-boronic acid 1.75 g (8.24 mmol), Pd (PPh ₃ ) ₄₀ To a flask containing .190 g (0.165 mmol) and 1.75 g (16.5 mmol) of Na ₂ CO ₃ , 35 mL of DME and 6 mL of water were added, and the mixture was heated and stirred at about 80 ° C. for 7 hours.
After completion of the reaction, the mixture was cooled to room temperature, water was added to precipitate a solid, and the solid was collected by filtration. The collected solid was purified by silica gel column chromatography. Toluene recrystallization was repeated for the solid obtained by purification to obtain 4.72 g of a pale yellow solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH1 (yield 50%).

(Synthesis Example 2) Synthesis of compound BH2

The synthesis scheme of compound BH2 is shown below.

(2-1) Synthesis of compound BH-2-1 Under an argon atmosphere, compound BH-1-2 15.00 g (45.0 mmol), 2-naphthylboronic acid 7.74 g (45.0 mmol), Pd (PPh ₃ ). ) ₄ 1.04g (0.900mmol), and _Na 2 _CO 3 _{9.54g (90.0mmol)} of entering a DME193mL flask, and water 32mL was added, and heating for 24 hours stirring at about 80 ° C..
After completion of the reaction, the mixture was cooled to room temperature, the reaction solution was transferred to a separating funnel, and the organic layer was extracted with toluene. The extracted organic layer was dried over sulfonyl ₄ , filtered, and the filtrate was concentrated to give a solid. The solid obtained by concentration was purified by silica gel column chromatography to obtain 10.3 g of a solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH-2-1 (yield 60%).

(2-2) Synthesis of Compound BH-2-2 A solution prepared by adding 526 mL of DMF to 10.0 g (26.3 mmol) of Compound BH-2-1 was dissolved by heating at about 50 ° C. and then cooled to room temperature. .. A DMF solution of 4.68 g (26.3 mmol) of N-bromosuccinimide (NBS) was added dropwise thereto, and the mixture was stirred at room temperature.
After completion of the reaction, the mixture was cooled to room temperature, water was added to precipitate a solid, and the solid was collected by filtration. The collected solid was purified by silica gel column chromatography. The solid obtained by purification was recrystallized from toluene and further purified to obtain 4.83 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH-2-2 (yield 40%).

(2-3) Synthesis of compound BH-2 Under an argon atmosphere, compound BH-2-2 4.00 g (8.71 mmol), dibenzofuran-2-boronic acid 1.85 g (8.71 mmol), Pd (PPh ₃ ). ₄ 0.201 g (0.174 mmol), and _Na 2 _CO 3 1.85g _(17.4mmol) of entering a DME37mL the flask, and water 6mL was added, and heating for 24 hours stirring at about 80 ° C..
After completion of the reaction, the mixture was cooled to room temperature, water was added to precipitate a solid, and the solid was collected by filtration. The collected solid was purified by silica gel column chromatography. Toluene recrystallization was repeated on the solid obtained by purification to obtain 2.38 g of a pale yellow solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH2 (yield 50%).

(Synthesis Example 3) Synthesis of compound BH3

The synthesis scheme of compound BH3 is shown below.

(3-1) Synthesis of compound BH-3-1 Under an argon atmosphere, compound BH-1-2 15.00 g (45.0 mmol), phenylboronic acid 5.49 g (45.0 mmol), Pd (PPh ₃ ) ₄ 1.04 g (0.900 mmol), and _Na 2 _CO 3 _{9.54g (90.0mmol)} of entering a DME193mL the flask, and water 32mL was added, and heating for 24 hours stirring at about 80 ° C..
After completion of the reaction, the mixture was cooled to room temperature, the reaction solution was transferred to a separating funnel, and the organic layer was extracted with toluene. The extracted organic layer was dried over sulfonyl ₄ , filtered, and the filtrate was concentrated to give a solid. The solid obtained by concentration was purified by silica gel column chromatography to obtain 8.92 g of a solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH-3-1 (yield 60%).

(3-2) Synthesis of Compound BH-3-2 A solution prepared by adding 484 mL of DMF to 8.00 g (24.2 mmol) of Compound BH-3-1 was dissolved by heating at about 50 ° C. and then cooled to room temperature. .. A DMF solution of 4.31 g (24.2 mmol) of N-bromosuccinimide (NBS) was added dropwise thereto, and the mixture was stirred at room temperature.
After completion of the reaction, the mixture was cooled to room temperature, water was added to precipitate a solid, and the solid was collected by filtration. The collected solid was purified by silica gel column chromatography. The solid obtained by purification was recrystallized from toluene and further purified to obtain 4.76 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH-3-2 (yield 48%).

(3-3) Synthesis of compound BH3 Compound BH-3-2 4.00 g (9.77 mmol), 4- (2-dibenzofuran) phenylboronic acid 2.82 g (9.77 mmol), Pd (PPh) under an argon atmosphere. ₃ ) 42 mL of DME and 7 mL of water were added to a flask containing ₄ 0.226 g (0.195 mmol) and 2.07 g (19.5 mmol) of Na ₂ CO ₃ , and the mixture was heated and stirred at about 80 ° C. for 24 hours.
After completion of the reaction, the mixture was cooled to room temperature, water was added to precipitate a solid, and the solid was collected by filtration. The collected solid was purified by silica gel column chromatography. Toluene recrystallization was repeated on the solid obtained by purification to obtain 2.80 g of a pale yellow solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH3 (yield 50%).

(Synthesis Example 4) Synthesis of compound BH4

The synthesis scheme of compound BH4 is shown below.

(4-1) Synthesis of compound BH-4-1 Under an argon atmosphere, compound BH-1-2 15.00 g (45.0 mmol), dibenzofuran-2-boronic acid 9.54 g (45.0 mmol), Pd (PPh). ₃₎ ₄ 1.04g _(0.900mmol), and _Na 2 _CO 3 _{9.54g (90.0mmol)} of entering a DME193mL the flask, and water 32mL was added, and heating for 24 hours stirring at about 80 ° C..
After completion of the reaction, the mixture was cooled to room temperature, the reaction solution was transferred to a separating funnel, and the organic layer was extracted with toluene. The extracted organic layer was dried over sulfonyl ₄ , filtered, and the filtrate was concentrated to give a solid. The solid obtained by concentration was purified by silica gel column chromatography to obtain 14.2 g of a solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH-4-1 (yield 75%).

(4-2) Synthesis of Compound BH-4-2 A solution prepared by adding 476 mL of DMF to 10.0 g (23.8 mmol) of Compound BH-4-1 was heated and dissolved at about 50 ° C., and then cooled to room temperature. .. A DMF solution of 4.23 g (23.8 mmol) of N-bromosuccinimide (NBS) was added dropwise thereto, and the mixture was stirred at room temperature.
After completion of the reaction, the mixture was cooled to room temperature, water was added to precipitate a solid, and the solid was collected by filtration. The collected solid was purified by silica gel column chromatography. The solid obtained by purification was recrystallized from toluene and further purified to obtain 5.11 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH-4-2 (yield 43%).

(4-3) Synthesis of compound BH4 Under an argon atmosphere, compound BH-4-2 5.00 g (10.0 mmol), 3-biphenylboronic acid 1.98 g (10.0 mmol), Pd (PPh ₃ ) ₄₀ . 231 g (0.200 mmol), and _Na 2 _CO 3 2.12g (20.0mmol) of entering a DME42mL the flask, and water 7mL added and heating for 24 hours stirring at about 80 ° C..
After completion of the reaction, the mixture was cooled to room temperature, water was added to precipitate a solid, and the solid was collected by filtration. The collected solid was purified by silica gel column chromatography. Toluene recrystallization was repeated on the solid obtained by purification to obtain 2.87 g of a pale yellow solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH4 (yield 50%).

(Synthesis Example 5) Synthesis of compound BH5

The synthesis scheme of compound BH5 is shown below.

(5-1) Synthesis of compound BH-5-1 Under an argon atmosphere, 2-bromoanthracene 20.0 g (78.0 mmol), 3-biphenylboronic acid 15.4 g (78.0 mmol), Pd (PPh ₃ ) ₄ 330 mL of DME and 55 mL of water were added to a 1 L flask containing 1.80 g (1.56 mmol) and 16.5 g (156 mmol) of Na ₂ CO ₃ , and the mixture was heated and stirred at about 80 ° C. for 7 hours.
After completion of the reaction, the mixture was cooled to room temperature, water was added to precipitate a solid, and the solid was collected by filtration. The collected solid was purified by silica gel column chromatography to obtain 22.6 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH-5-1 (yield 88%).

(5-2) Synthesis of Compound BH-5-2 A solution prepared by dissolving 15.0 g (45.4 mmol) of Compound BH-5-1 in DMF908 mL was heated and stirred at about 80 ° C. To this, 8.08 g (45.4 mmol) of N-bromosuccinimide (NBS) dissolved in 1.18 L of DMF was added dropwise.
After completion of the reaction, the mixture was cooled to room temperature, water was added to precipitate a solid, and the solid was collected by filtration. The collected solid was purified by silica gel column chromatography. The solid obtained by purification was recrystallized from toluene and further purified to obtain 9.29 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH-5-2 (yield 50%).

(5-3) Synthesis of compound BH-5-3 Under an argon atmosphere, compound BH-5-2 9.00 g (22.0 mmol), 2-naphthylboronic acid 3.78 g (22.0 mmol), Pd (PPh ₃ ). ) ₄ 0.508 g (0.440 mmol) and Na ₂ CO ₃ 4.66 g (44.0 mmol) were placed in a 1 L flask containing 94 mL of DME and 15 mL of water, and the mixture was heated and stirred at about 80 ° C. for 24 hours.
After completion of the reaction, the mixture was cooled to room temperature, the reaction solution was transferred to a separating funnel, and the organic layer was extracted with toluene. The extracted organic layer was dried over sulfonyl ₄ , filtered, and the filtrate was concentrated to give a solid. The solid obtained by concentration was purified by silica gel column chromatography to obtain 8.03 g of a solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH-5-3 (yield 80%).

(5-4) Synthesis of Compound BH-5-4 A solution prepared by adding 350 mL of DMF to 8.00 g (17.5 mmol) of compound BH-5-3 was dissolved by heating at about 50 ° C., and then cooled to room temperature. .. A DMF solution of 3.12 g (17.5 mmol) of N-bromosuccinimide (NBS) was added dropwise thereto, and the mixture was stirred at room temperature.
After completion of the reaction, the mixture was cooled to room temperature, water was added to precipitate a solid, and the solid was collected by filtration. The collected solid was purified by silica gel column chromatography. The solid obtained by purification was recrystallized from toluene and further purified to obtain 3.75 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH-5-4 (yield 40%).

(5-5) Synthesis of compound BH5 Under an argon atmosphere, compound BH-5-4 3.00 g (5.60 mmol), dibenzofuran-2-boronic acid 1.19 g (5.60 mmol), Pd (PPh ₃ ) ₄₀ To a flask containing 129 g (0.112 mmol) and 1.19 g (11.2 mmol) of Na ₂ CO ₃ , 24 mL of DME and 4 mL of water were added, and the mixture was heated and stirred at about 80 ° C. for 7 hours.
After completion of the reaction, the mixture was cooled to room temperature, water was added to precipitate a solid, and the solid was collected by filtration. The collected solid was purified by silica gel column chromatography. Toluene recrystallization was repeated on the solid obtained by purification to obtain 1.74 g of a pale yellow solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH5 (yield 50%).

(Synthesis Example 6) Synthesis of compound BH6

The synthesis scheme of compound BH6 is shown below.

(6-1) Synthesis of compound BH-6-1 Under an argon atmosphere, compound BH-1-2 15.00 g (45.0 mmol), dibenzofuran-2-boronic acid 9.54 g (45.0 mmol), Pd (PPh). ₃₎ ₄ 1.04g _(0.900mmol), and _Na 2 _CO 3 _{9.54g (90.0mmol)} of entering a DME193mL flask, water 32mL was added, and heating for 24 hours stirring at about 80 ° C..
After completion of the reaction, the mixture was cooled to room temperature, the reaction solution was transferred to a separating funnel, and the organic layer was extracted with toluene. The extracted organic layer was dried over sulfonyl ₄ , filtered, and the filtrate was concentrated to give a solid. The solid obtained by concentration was purified by silica gel column chromatography to obtain 15.1 g of a solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH-6-1 (yield 80%).

(6-2) Synthesis of Compound BH-6-2 A solution prepared by adding 476 mL of DMF to 10.0 g (23.8 mmol) of Compound BH-6-1 was heated and dissolved at about 50 ° C., and then cooled to room temperature. .. A DMF solution of 4.23 g (23.8 mmol) of N-bromosuccinimide (NBS) was added dropwise thereto, and the mixture was stirred at room temperature.
After completion of the reaction, the mixture was cooled to room temperature, water was added to precipitate a solid, and the solid was collected by filtration. The collected solid was purified by silica gel column chromatography. The solid obtained by purification was recrystallized from toluene and further purified to obtain 5.94 g of a white solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH-6-2 (yield 50%).

(6-3) Synthesis of compound BH6 Under an argon atmosphere, compound BH-6-2 5.00 g (10.0 mmol), 3- (2-dibenzofuran) phenylboronic acid 2.88 g (10.0 mmol), Pd (PPh) ₃₎ ₄ _{0.231g (0.200mmol),} and _Na 2 _CO 3 2.12g (20.0mmol) of entering a DME42mL the flask, and water 7mL added and heating for 24 hours stirring at about 80 ° C..
After completion of the reaction, the mixture was cooled to room temperature, water was added to precipitate a solid, and the solid was collected by filtration. The collected solid was purified by silica gel column chromatography. Toluene recrystallization was repeated on the solid obtained by purification to obtain 2.99 g of a pale yellow solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH6 (yield 45%).

(Synthesis Example 7) Synthesis of compound BH7

The synthesis scheme of compound BH7 is shown below.

(7-1) Synthesis of Compound BH7 Compound BH-3-2 5.00 g (12.2 mmol), 4- (2-dibenzofuran) naphthylboronic acid 4.13 g (12.2 mmol), Pd (PPh) under an argon atmosphere. ₃ ) 52 mL of DME and 9 mL of water were added to a flask containing ₄ 0.282 g (0.244 mmol) and 2.59 g (24.4 mmol) of Na ₂ CO ₃ , and the mixture was heated and stirred at about 80 ° C. for 24 hours.
After completion of the reaction, the mixture was cooled to room temperature, water was added to precipitate a solid, and the solid was collected by filtration. The collected solid was purified by silica gel column chromatography. Toluene recrystallization was repeated on the solid obtained by purification to obtain 3.80 g of a pale yellow solid. The obtained compound was subjected to FD-MS analysis and identified as compound BH7 (yield 50%).

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

Claims

A compound represented by the following general formula (1).

(In the general formula (1),
One or more of two or more adjacent pairs of R 11 , R 12 , R 17 and R 18
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
One or more of two or more adjacent pairs of R 13 , R 14 , R 15 and R 16
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
R 11 to R 18 that do not form the monocyclic ring and do not form the condensed ring are independent of each other.
Hydrogen atom,
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
However, at least one of R 11 to R 18 is
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L 11 is a substituted or unsubstituted ring-forming carbon number 6 to 13 arylene group.
m is 0, 1, or 2
When m is 0, the fused ring containing X in the general formula (1) and the anthracene ring are bonded by a single bond.
when m is 2, two L 11 may be identical to each other or different,
Sets of the two L 11 is
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
X is an oxygen atom or a sulfur atom,
Of R 101 to R 107 , one or more pairs of two or more adjacent pairs do not join each other.
R 101 to R 107 are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Cyano group,
Halogen atom,
-A group represented by Si (R 901 ) (R 902 ) (R 903 ),
A group represented by -O- (R 904 ),
A group represented by -S- (R 905 ),
A group represented by -N (R 906 ) (R 907 ),
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
Ar 3 is
A group represented by the following general formula (1a),
The group represented by the following general formula (1b),
A group represented by the following general formula (1c),
A group represented by the following general formula (1d),
Substituted or unsubstituted fluorenyl group,
A substituted or unsubstituted ring-forming aryl group having 15 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 16 atoms.
However, Ar 3 bonded to one of the 9-position carbon atom and the 10-position carbon atom of the anthracene ring shown in the general formula (1) and the other of the 9-position carbon atom and the 10-position carbon atom of the anthracene ring The groups to which they bind are different from each other. )

(In the general formula (1a), R 111 to R 115 are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Cyano group,
Halogen atom,
-A group represented by Si (R 901 ) (R 902 ) (R 903 ),
A group represented by -O- (R 904 ),
A group represented by -S- (R 905 ),
A group represented by -N (R 906 ) (R 907 ),
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
However, when m is 0, the general formula (1a) satisfies the following condition (i) or (ii).
(I) At least one of R 111 to R 115 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted ring-forming carbon. Cycloalkyl group of number 3 to 50, cyano group, halogen atom, group represented by -Si (R 901 ) (R 902 ) (R 903 ), group represented by -O- (R 904 ), -S A group represented by- (R 905 ), a group represented by -N (R 906 ) (R 907 ), a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring. It is a heterocyclic group having 5 to 50 atoms.
(Ii) R 111 to R 115 are hydrogen atoms, and at least one of R 11 to R 18 is independently substituted phenyl group, substituted or unsubstituted biphenyl group, or substituted or unsubstituted. It is a terphenyl group. )

(In the general formula (1b), R 121 to R 127 are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Cyano group,
Halogen atom,
-A group represented by Si (R 901 ) (R 902 ) (R 903 ),
A group represented by -O- (R 904 ),
A group represented by -S- (R 905 ),
A group represented by -N (R 906 ) (R 907 ),
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
However, the general formula (1b) satisfies the following condition (iii) or (iv).
(Iii) At least one of R 121 to R 127 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted ring formation. Cycloalkyl group having 3 to 50 carbon atoms, cyano group, halogen atom, group represented by -Si (R 901 ) (R 902 ) (R 903 ), group represented by -O- (R 904 ),- A group represented by S- (R 905 ), a group represented by -N (R 906 ) (R 907 ), a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted aryl group. It is a heterocyclic group having 5 to 50 ring-forming atoms.
(Iv) R 121 to R 127 are hydrogen atoms, and at least one of R 11 to R 18 is independently substituted phenyl group, substituted or unsubstituted biphenyl group, or substituted or unsubstituted. It is a terphenyl group. )

(In the general formula (1c),
When m is 0, R 131 to R 137 are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Cyano group,
Halogen atom,
-A group represented by Si (R 901 ) (R 902 ) (R 903 ),
A group represented by -O- (R 904 ),
A group represented by -S- (R 905 ),
A group represented by -N (R 906 ) (R 907 ),
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
When m is 1 or 2, at least one of R 131 to R 137 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, substituted or unsubstituted. Substituent ring formation Cycloalkyl group having 3 to 50 carbon atoms, cyano group, halogen atom, group represented by -Si (R 901 ) (R 902 ) (R 903 ), represented by -O- (R 904 ). Group, a group represented by -S- (R 905 ), a group represented by -N (R 906 ) (R 907 ), a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted group. Alternatively, it is an unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. )

(In the general formula (1d),
L 12 is a substituted or unsubstituted ring-forming carbon number 6 to 13 arylene group.
HAR is a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. )
(R 901 , R 902 , R 903 , R 904 , R 905 , R 906 and R 907 in the general formulas (1), (1a) to (1c) are independent of each other.
Substituent or unsubstituted ring-forming aryl groups having 6 to 50 carbon atoms,
Substituted or unsubstituted ring-forming heterocyclic groups having 5 to 50 atoms,
A substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms.
If R 901 is plural, R 901 may be identical to each other or different,
If R 902 is plural, R 902 may be identical to each other or different,
If R 903 is plural, R 903 may be identical to each other or different,
If R 904 is plural, R 904 may be identical to each other or different,
If R 905 is plural, R 905 may be identical to each other or different,
When there are multiple R- 906s , the plurality of R- 906s are the same as or different from each other.
If R 907 is plural, R 907 may be identical to each other or different,
* In the general formulas (1a) to (1d) indicate the bonding position with the anthracene ring. )
It is represented by any of the following general formulas (11) to (14).
The compound according to claim 1.

(R 11 in the general formula (11), R 12 in the general formula (12), R 17 in R 18, and the general formula (14) in the general formula (13) are each independently,
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L 11 in the general formula (11) ~ (14), m, X, R 101 ~ R 107, and Ar 3, respectively, wherein L 11 in the general formula (1), m, X, R 101 ~ R 107 , And Ar 3 are synonymous with
However, Ar 3 bonded to one of the 9-position carbon atom and the 10-position carbon atom of the anthracene ring shown in the general formulas (11) to (14), and the 9-position carbon atom and the 10-position carbon of the anthracene ring. The groups attached to the other of the atoms are different from each other. )
m is 0,
The compound according to claim 1 or 2.
m is 1 or 2,
The compound according to claim 1 or 2.
m is 1,
The compound according to claim 4.
It is represented by the general formula (11).
The compound according to claim 2.
Ar 3 is a group represented by the general formula (1a).
The compound according to any one of claims 1 to 6.
It is represented by the following general formula (11a).
The compound according to claim 6.

(R 11 in the general formula (11a) is
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L 11, m, X, and R 101 ~ R 107 are each, the L 11 in the general formula (1), m, has the same meaning X, and the R 101 ~ R 107,
R 111 to R 115 are independently synonymous with R 111 to R 115 in the general formula (1a). )
It is represented by the following general formula (111a).
The compound according to claim 8.

(R 11 in the general formula (111a) is
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
X and R 101 to R 107 are synonymous with X and R 101 to R 107 in the general formula (1), respectively.
R 111 to R 115 are independently synonymous with R 111 to R 115 in the general formula (1a).
However, the compound represented by the general formula (111a) satisfies the following conditions (i) or (ii).
(I) At least one of R 111 to R 115 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted ring-forming carbon. Cycloalkyl group of number 3 to 50, cyano group, halogen atom, group represented by -Si (R 901 ) (R 902 ) (R 903 ), group represented by -O- (R 904 ), -S A group represented by- (R 905 ), a group represented by -N (R 906 ) (R 907 ), a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring. It is a heterocyclic group having 5 to 50 atoms.
(Ii) R 111 to R 115 are hydrogen atoms, and R 11 is a substituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group. )
m is 1 or 2, and is represented by the following general formula (112a) or the following general formula (113a).
The compound according to claim 8.

(R 11 in the general formulas (112a) and (113a) are independent of each other.
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L 11 , L 111 and L 112 are independently substituted or unsubstituted ring-forming arylene groups having 6 to 13 carbon atoms, respectively.
The set consisting of L 111 and L 112 is
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
X and R 101 to R 107 are synonymous with X and R 101 to R 107 in the general formula (1), respectively.
R 111 to R 115 are independently synonymous with R 111 to R 115 in the general formula (1a). )
It is represented by the general formula (13).
The compound according to claim 2.
It is represented by the following general formula (13a).
The compound according to claim 11.

(R 18 in the general formula (13a) is
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L 11, m, X, and R 101 ~ R 107 are each, the L 11 in the general formula (1), m, has the same meaning X, and the R 101 ~ R 107,
R 111 to R 115 are independently synonymous with R 111 to R 115 in the general formula (1a). )
It is represented by the following general formula (131a).
The compound according to claim 12.

(R 18 in the general formula (131a) is
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
X and R 101 to R 107 are synonymous with X and R 101 to R 107 in the general formula (1), respectively.
R 111 to R 115 are independently synonymous with R 111 to R 115 in the general formula (1a).
However, the compound represented by the general formula (131a) satisfies the following conditions (v) or (vi).
(V) At least one of R 111 to R 115 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted ring-forming carbon. Cycloalkyl group of number 3 to 50, cyano group, halogen atom, group represented by -Si (R 901 ) (R 902 ) (R 903 ), group represented by -O- (R 904 ), -S A group represented by- (R 905 ), a group represented by -N (R 906 ) (R 907 ), a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring. It is a heterocyclic group having 5 to 50 atoms.
(Vi) R 111 to R 115 are hydrogen atoms, and R 18 is a substituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group. )
Ar 3 is a group represented by the general formula (1b) or a group represented by the general formula (1c).
The compound according to any one of claims 1 to 6.
It is represented by the following general formula (11b).
The compound according to claim 14.

(R 11 in the general formula (11b) is
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L 11, m, X, and R 101 ~ R 107 are each, the L 11 in the general formula (1), m, has the same meaning X, and the R 101 ~ R 107,
R 121 to R 127 are independently synonymous with R 121 to R 127 in the general formula (1b).
However, the compound represented by the general formula (11b) satisfies the following conditions (iii) or (iv).
(Iii) At least one of R 121 to R 127 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted ring formation. Cycloalkyl group having 3 to 50 carbon atoms, cyano group, halogen atom, group represented by -Si (R 901 ) (R 902 ) (R 903 ), group represented by -O- (R 904 ),- A group represented by S- (R 905 ), a group represented by -N (R 906 ) (R 907 ), a substituted or unsubstituted aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted aryl group. It is a heterocyclic group having 5 to 50 ring-forming atoms.
(Iv) R 121 to R 127 are hydrogen atoms, and R 11 is a substituted phenyl group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group. )
It is represented by the following general formula (11c).
The compound according to claim 14.

(R 11 in the general formula (11c) is
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L 11, m, X, and R 101 ~ R 107 are each, the L 11 in the general formula (1), m, has the same meaning X, and the R 101 ~ R 107,
R 131 to R 137 are independently synonymous with R 131 to R 137 in the general formula (1c). )
It is represented by the following general formula (111c).
The compound according to claim 16.

(R 11 in the general formula (111c) is
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
X, R 101 ~ R 107, and R 131 ~ R 137 are each, X in the general formula (1), R 101 ~ R 107, and is synonymous with R 131 ~ R 137. )
It is represented by the following general formula (112c) or the following general formula (113c).
The compound according to claim 16.

(R 11 in the general formulas (112c) and (113c) are independent of each other.
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L 11 , L 113, and L 114 are independently substituted or unsubstituted ring-forming arylene groups having 6 to 13 carbon atoms, respectively.
The set consisting of L 113 and L 114 is
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
X and R 101 to R 107 are synonymous with X and R 101 to R 107 in the general formula (1), respectively.
R 131 to R 137 are independently synonymous with R 131 to R 137 in the general formula (1c).
However, at least one of R 131 to R 137 is a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, and a substituted or unsubstituted ring-forming carbon number. 3 to 50 cycloalkyl groups, cyano groups, halogen atoms, groups represented by -Si (R 901 ) (R 902 ) (R 903 ), groups represented by -O- (R 904 ), -S- Group represented by (R 905 ), group represented by -N (R 906 ) (R 907 ), substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or substituted or unsubstituted ring formation. It is a heterocyclic group having 5 to 50 atoms. )
Ar 3 is a group represented by the general formula (1d) or a substituted or unsubstituted heterocyclic group having 5 to 16 ring-forming atoms.
The compound according to any one of claims 1 to 6.
It is represented by the following general formula (11d).
The compound according to claim 6.

(R 11 in the general formula (11d) is
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L 11, m, X, and R 101 ~ R 107 are each, the L 11 in the general formula (1), m, has the same meaning X, and the R 101 ~ R 107,
L 12 and HAR are synonymous with L 12 and HAR in the general formula (1d). )
It is represented by the following general formula (111d).
The compound according to claim 20.

(R 11 in the general formula (111d) is
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
X and R 101 to R 107 are synonymous with X and R 101 to R 107 in the general formula (1), respectively.
L 12 is a substituted or unsubstituted ring-forming carbon number 6 to 13 arylene group.
HAR is a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. )
It is represented by the following general formula (112d) or the following general formula (113d).
The compound according to claim 20.

(R 11 in the general formulas (112d) and (113d) are independent of each other.
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L 11 , L 115 and L 116 are independently substituted or unsubstituted ring-forming arylene groups having 6 to 13 carbon atoms, respectively.
The set consisting of L 115 and L 116 is
Combine with each other to form a substituted or unsubstituted monocycle,
Bond to each other to form substituted or unsubstituted fused rings, or not to each other
X and R 101 to R 107 are synonymous with X and R 101 to R 107 in the general formula (1), respectively.
L 12 is a substituted or unsubstituted ring-forming carbon number 6 to 13 arylene group.
HAR is a substituted or unsubstituted heterocyclic group having 5 to 50 ring-forming atoms. )
It is represented by the following general formula (11f).
The compound according to claim 19.

(In the general formula (11f),
Ar 3 is a substituted or unsubstituted heterocyclic group having 5 to 16 ring-forming atoms.
R 11 are independent of each other
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L 11 is a substituted or unsubstituted ring-forming carbon number 6 to 13 arylene group.
X and R 101 to R 107 are synonymous with X and R 101 to R 107 in the general formula (1), respectively. )
It is represented by the following general formula (11 g).
The compound according to claim 19.

(In the general formula (11 g),
R 11 are independent of each other
Substituted or unsubstituted phenyl group,
A substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group.
L 11 is a substituted or unsubstituted ring-forming carbon number 6 to 13 arylene group.
X 1 and X 2 are independently synonymous with X in the general formula (1).
R 101 to R 107 are independently synonymous with R 101 to R 107 in the general formula (1).
R 141 to R 146 and R 148 are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Cyano group,
Halogen atom,
-A group represented by Si (R 901 ) (R 902 ) (R 903 ),
A group represented by -O- (R 904 ),
A group represented by -S- (R 905 ),
A group represented by -N (R 906 ) (R 907 ),
A substituted or unsubstituted ring-forming aryl group having 6 to 50 carbon atoms, or a substituted or unsubstituted ring-forming heterocyclic group having 5 to 50 atoms.
R 901 to R 907 are independently synonymous with R 901 to R 907 in the general formula (1). )
At least one of R 11 to R 18 is a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group.
The compound according to any one of claims 1 to 24.
At least one of R 11 to R 18 is a group represented by the following formulas (1e), (1f), (1g) or (1h).
The compound according to any one of claims 1 to 25.

(* In the formulas (1e), (1f), (1g) and (1h) indicates the bonding position with the anthracene ring.)
L 11 is a substituted or unsubstituted phenylene group,
The compound according to any one of claims 1 to 26.
L 11 is a group represented by the following formula (100a) or (100b).
The compound according to any one of claims 1 to 27.

(Of the two * in the formulas (100a) and (100b), one * indicates the bonding position with the anthracene ring, and the other * is the fused ring containing X in the general formula (1). Indicates the connection position of.)
X is an oxygen atom,
The compound according to any one of claims 1 to 28.
R 101 to R 107 are independent of each other.
Hydrogen atom,
Substituent or unsubstituted alkyl groups having 1 to 50 carbon atoms,
Substituted or unsubstituted haloalkyl groups having 1 to 50 carbon atoms,
Substitutable or unsubstituted ring-forming cycloalkyl group having 3 to 50 carbon atoms,
Cyano group,
A halogen atom, or a group represented by -Si (R 901 ) (R 902 ) (R 903 ).
The compound according to any one of claims 1 to 29.
R 101 to R 107 are hydrogen atoms,
The compound according to any one of claims 1 to 29.
It has an anode, a cathode, and an organic layer.
The organic layer contains the compound according to any one of claims 1 to 31.
Organic electroluminescence element.
The organic layer includes a light emitting layer.
The light emitting layer contains the compound as the first compound.
The organic electroluminescence device according to claim 32.
The light emitting layer contains a second fluorescently luminescent compound and contains.
The singlet energy S 1 (H) of the first compound and the singlet energy S 1 (D) of the second compound satisfy the relationship of the following mathematical formula (Equation 1).
The organic electroluminescence device according to claim 33.
S 1 (H)> S 1 (D) ... (Equation 1)
An electronic device equipped with the organic electroluminescence device according to any one of claims 32 to 34.