JP7710104B2 - Compound, material for organic electroluminescence device, organic electroluminescence device, and electronic device - Google Patents

Description

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

Generally, an organic electroluminescence element (hereinafter sometimes referred to as "organic EL element") is composed of an anode, a cathode, and an organic layer sandwiched between the anode and cathode. When a voltage is applied between the two electrodes, electrons are injected from the cathode side and holes are injected from the anode side into the light-emitting region, where they recombine to generate an excited state, and light is emitted when the excited state returns to the ground state. Therefore, in order to obtain a high-performance organic EL element, it is important to find a combination of materials that efficiently transports electrons or holes to the light-emitting region, facilitates recombination of electrons and holes, and efficiently emits excitons.

Patent documents 1 to 13 disclose compounds used as materials for organic electroluminescence devices.

China Patent Publication No. 111675701 China Patent Publication No. 109096179 Korean Patent Publication No. 10-2019-0035567 Korean Patent Publication No. 10-2018-0066855 US Patent Application Publication No. 2016/0293843 US Patent Application Publication No. 2015/0179953 US Patent Application Publication No. 2016/0301005 Korean Patent Publication No. 10-2018-0116740 US Patent Application Publication No. 2017/0194569 US Patent Application Publication No. 2017/0186978 US Patent Application Publication No. 2017/0186969 Korean Patent Publication No. 10-2019-0005522 International Publication No. 2021/045590

Although many compounds for organic EL devices have been reported, there is still a need to further improve the performance of organic EL devices.

The present invention has been made to solve the above-mentioned problems, and aims to provide a compound that further improves the performance of an organic EL element, an organic EL element having further improved element performance, and an electronic device including such an organic EL element.

As a result of extensive research into the performance of organic EL elements containing the compounds described in Patent Documents 1 to 13, the inventors have found that an organic EL element containing a compound represented by the following formula (1) has improved performance.

In one aspect, the present invention provides a compound represented by formula (1):

(In formula (1),
N ^* is the central nitrogen atom.
One of R ^a and R ^b is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and the other is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
However, R ^a and R ^b may be bonded to each other to form a substituted or unsubstituted ring.
One selected from R ² , R ³ , R ⁶ and R ⁷ is a single bond bonding to *1, and R ¹ , R ⁴ , R ⁵ , R ⁸ , and R ² , R ³ , R ⁶ and R ⁷ that are not a single bond bonding to *1 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 15 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
Any two adjacent groups selected from R ¹ , R ⁴ , R ⁵ , R ⁸ , and R ² , R ³ , R ⁶ and R ⁷ that are not a single bond are not bonded to each other and therefore do not form a ring.
R ¹¹ to R ¹⁴ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.
Adjacent two selected from R ¹¹ to R ¹⁴ are not bonded to each other and therefore do not form a ring.
L ¹ to L ⁴ each independently represent a single bond or an arylene group having 6 to 30 ring carbon atoms.
Ar ¹ and Ar ² are groups represented by any one of the following formulas (1a) to (1g).

(In formula (1a),
*21 is the bonding position to ^L1 or ^L2 .
One selected from R ¹⁰¹ to R ¹⁰⁵ is a single bond bonding to *22, one selected from R ¹⁰⁶ to R ¹¹⁰ is a single bond bonding to *23, and one selected from R ¹¹¹ to R ¹¹⁵ is a single bond bonding to *24.
The R ¹⁰¹ to R ¹¹⁵ that are not single bonds are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms.
adjacent two of R ¹⁰¹ to R ¹⁰⁵ which are not single bonds are not bonded to each other and therefore do not form a ring;
any two adjacent R ¹⁰⁶ to R ¹¹⁰ which are not single bonds are not bonded to each other and therefore do not form a ring;
Any two adjacent groups selected from R ¹¹¹ to R ¹¹⁵ which are not single bonds are not bonded to each other and therefore do not form a ring.
m is 0 or 1, n is 0 or 1, and l is 0 or 1.
R ¹¹⁶ to R ¹²⁰ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
Any two adjacent groups selected from R ¹¹⁶ to R ¹²⁰ are not bonded to each other and therefore do not form a ring.

(In formula (1b),
*25 is the bonding position to ^L1 or ^L2 .
One selected from R ¹²¹ to R ¹²⁸ is a single bond bonded to *26.
The R ¹²¹ to R ¹²⁸ that are not single bonds are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms.
Any two adjacent groups selected from R ¹²¹ to R ¹²⁸ that are not single bonds are not bonded to each other and therefore do not form a ring.
provided that when L ¹ is a p-phenylene group and Ar ¹ is represented by formula (1b), one selected from R ¹²¹ , R ¹²⁴ , R ¹²⁵ , and R ¹²⁸ in the group represented by formula (1b) which is bonded to the p-phenylene group is a single bond bonded to *26;
When L ² is a p-phenylene group and Ar ² is represented by formula (1b), one selected from R ¹²¹ , R ¹²⁴ , R ¹²⁵ , and R ¹²⁸ in the group represented by formula (1b) which is bonded to the p-phenylene group is a single bond bonded to *26.

(In formula (1c),
*27 is the bonding position to ^L1 or ^L2 .
One selected from R ¹³¹ to R ¹⁴⁰ is a single bond bonded to *28.
The R ¹³¹ to R ¹⁴⁰ that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
Any two adjacent groups selected from R ¹³¹ to R ¹⁴⁰ that are not single bonds are not bonded to each other and therefore do not form a ring.

(In formula (1d),
*29 is the bonding position to ^L1 or ^L2 .
One selected from R ¹⁴¹ to R ¹⁵² is a single bond bonded to *30.
The R ¹⁴¹ to R ¹⁵² that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
Any two adjacent groups selected from R ¹⁴¹ to R ¹⁵² that are not single bonds are not bonded to each other and therefore do not form a ring structure.

(In formula (1e),
*31 is the bonding position to ^L1 or ^L2 .
One selected from R ¹⁶¹ to R ¹⁶⁵ is a single bond bonding to *32, and the other selected from R ¹⁶¹ to R ¹⁶⁵ is a single bond bonding to *33.
R ¹⁶¹ to R ¹⁶⁵ which are not a single bond bonded to the *32 and are not a single bond bonded to the *33 are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group.
Any two adjacent bonds selected from R ¹⁶¹ to R ¹⁶⁵ that are not a single bond bonded to *32 and that are not a single bond bonded to *33 are not bonded to each other and therefore do not form a ring.
R ¹⁷¹ to R ¹⁷⁵ and R ¹⁸¹ to R ¹⁸⁵ each independently represent a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms.
any two adjacent ones selected from R ¹⁷¹ to R ¹⁷⁵ may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore not form a ring;
Any two adjacent groups selected from R ¹⁸¹ to R ¹⁸⁵ may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore not form a ring.

(In formula (1f),
*34 is the bonding position to ^L1 or ^L2 .
X is an oxygen atom, a sulfur atom, or NR ^A.
One selected from R ¹⁹¹ to R ¹⁹⁸ and R ^A is a single bond bonded to *35.
The R ^{3 A} that is not a single bond is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
The R ¹⁹¹ to R ¹⁹⁸ that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
Any two adjacent groups selected from R ¹⁹¹ to R ¹⁹⁸ that are not single bonds may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore not form a ring.

(In formula (1g),
*36 is the bonding position to ^L1 or ^L2 .
One selected from R ^B , R ^C , and R ²⁰¹ to R ²⁰⁸ is a single bond bonded to *37.
The ^R and ^R that are not single bonds are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
The R ^B and R ^C which are not single bonds may be bonded to each other to form a substituted or unsubstituted ring.
The R ²⁰¹ to R ²⁰⁸ that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
Any two adjacent non-single bonds selected from R ²⁰¹ to R ²⁰⁸ are not bonded to each other and therefore do not form a ring.

In another aspect, the present invention provides a material for an organic electroluminescent device comprising a compound represented by formula (1).

In yet another aspect, the present invention provides an organic electroluminescent device comprising a cathode, an anode, and an organic layer between the cathode and the anode, the organic layer comprising an emitting layer, and at least one layer of the organic layer comprising a compound represented by formula (1).

In yet another aspect, the present invention provides an electronic device comprising the organic electroluminescent element.

Organic EL devices containing the compound represented by formula (1) exhibit improved device performance.

FIG. 1 is a schematic diagram illustrating an example of a layer structure of an organic EL element according to one embodiment of the present invention. FIG. 2 is a schematic diagram showing another example of a layer structure of an organic EL element according to an embodiment of the present invention. FIG. 2 is a schematic diagram showing still another example of a layer structure of an organic EL element according to an embodiment of the present invention.

[Definition]
In this specification, hydrogen atoms include isotopes having different numbers of neutrons, namely protium, deuterium, and tritium.

In this specification, in a chemical structural formula, any possible bonding position that is not explicitly indicated with a symbol such as "R" or "D" representing a deuterium atom is assumed to have a hydrogen atom, i.e., a light hydrogen atom, a deuterium atom, or a tritium atom, bonded thereto.

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

In this specification, the number of ring atoms refers to the number of atoms constituting the ring itself of a compound (e.g., a monocyclic compound, a fused ring compound, a bridged compound, a carbocyclic compound, and a heterocyclic compound) having a structure in which atoms are bonded in a ring (e.g., a monocyclic ring, a fused ring, and a ring assembly). The number of ring atoms does not include atoms that do not constitute a ring (e.g., a hydrogen atom that terminates the bond of an atom constituting a ring) or atoms contained in a substituent when the ring is substituted with a substituent. The "number of ring atoms" described below is the same unless otherwise specified. For example, the number of ring atoms of a pyridine ring is 6, the number of ring atoms of a quinazoline ring is 10, and the number of ring atoms of a furan ring is 5. For example, the number of hydrogen atoms or atoms constituting a substituent bonded to a pyridine ring is not included in the number of pyridine ring atoms. Therefore, the number of ring atoms of a pyridine ring to which a hydrogen atom or a substituent is bonded is 6. For example, hydrogen atoms bonded to carbon atoms of a quinazoline ring or atoms constituting a substituent are not included in the number of ring atoms of the quinazoline ring. Therefore, the number of ring atoms of a quinazoline ring to which a hydrogen atom or a substituent is bonded is 10.

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

In this specification, the "atomic number XX to YY" in the expression "substituted or unsubstituted ZZ group having atomic number XX to YY" refers to the number of atoms when the ZZ group is unsubstituted, and does not include the number of atoms of the substituents when the ZZ group is substituted. Here, "YY" is larger than "XX", "XX" means an integer of 1 or more, and "YY" means an integer of 2 or more.

In this specification, the term "unsubstituted ZZ group" refers to the case where "a substituted or unsubstituted ZZ group" is an "unsubstituted ZZ group", and the term "substituted ZZ group" refers to the case where "a substituted or unsubstituted ZZ group" is a "substituted ZZ group".
In the present specification, "unsubstituted" in the case of "a substituted or unsubstituted ZZ group" means that a hydrogen atom in the ZZ group is not replaced with a substituent. The hydrogen atom in the "unsubstituted ZZ group" is a protium atom, a deuterium atom, or a tritium atom.
In the present specification, "substitution" in the case of "a substituted or unsubstituted ZZ group" means that one or more hydrogen atoms in the ZZ group are replaced with a substituent. Similarly, "substitution" in the case of "a BB group substituted with an AA group" means that one or more hydrogen atoms in the BB group are replaced with an AA group.

"Substituents Described Herein"
The substituents described in this specification will be described below.

The "unsubstituted aryl group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification.
The "unsubstituted heterocyclic group" described in this specification has 5 to 50 ring atoms, preferably 5 to 30, and more preferably 5 to 18 ring atoms, unless otherwise specified in this specification.
The "unsubstituted alkyl group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.
The number of carbon atoms in the "unsubstituted alkenyl group" described in this specification is, unless otherwise specified in this specification, 2 to 50, preferably 2 to 20, and more preferably 2 to 6.
The number of carbon atoms in the "unsubstituted alkynyl group" described in this specification, unless otherwise specified in this specification, is 2 to 50, preferably 2 to 20, and more preferably 2 to 6.
The "unsubstituted cycloalkyl group" described in this specification has 3 to 50 ring carbon atoms, preferably 3 to 20, and more preferably 3 to 6 ring carbon atoms, unless otherwise specified in this specification.
The "unsubstituted arylene group" described in this specification has 6 to 50 ring carbon atoms, preferably 6 to 30, and more preferably 6 to 18 ring carbon atoms, unless otherwise specified in this specification.
The number of ring atoms in the “unsubstituted divalent heterocyclic group” described in this specification is 5 to 50, preferably 5 to 30, and more preferably 5 to 18, unless otherwise specified in this specification.
The "unsubstituted alkylene group" described in this specification has 1 to 50 carbon atoms, preferably 1 to 20 carbon atoms, and more preferably 1 to 6 carbon atoms, unless otherwise specified in this specification.

- "Substituted or unsubstituted aryl group"
Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in this specification include the following unsubstituted aryl group (specific example group G1A) and substituted aryl group (specific example group G1B). (Here, the term "unsubstituted aryl group" refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group", and the term "substituted aryl group" refers to the case where the "substituted or unsubstituted aryl group" is a "substituted aryl group".) In this specification, the term "aryl group" simply refers to both an "unsubstituted aryl group" and a "substituted aryl group".
The term "substituted aryl group" refers to a group in which one or more hydrogen atoms of an "unsubstituted aryl group" are replaced with a substituent. Examples of the "substituted aryl group" include the "unsubstituted aryl group" in the specific example group G1A below in which one or more hydrogen atoms are replaced with a substituent, and the substituted aryl group in the specific example group G1B below. The examples of the "unsubstituted aryl group" and the examples of the "substituted aryl group" listed here are merely examples, and the "substituted aryl group" described in this specification also includes a group in which a hydrogen atom bonded to a carbon atom of the aryl group itself in the "substituted aryl group" in the specific example group G1B below is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted aryl group" in the specific example group G1B below is further replaced with a substituent.

Unsubstituted aryl groups (specific example group G1A):
Phenyl group,
p-biphenyl group,
m-biphenyl group,
o-biphenyl group,
p-terphenyl-4-yl group,
p-terphenyl-3-yl group,
p-terphenyl-2-yl group,
m-terphenyl-4-yl group,
m-terphenyl-3-yl group,
m-terphenyl-2-yl group,
o-terphenyl-4-yl group,
o-terphenyl-3-yl group,
o-terphenyl-2-yl group,
1-naphthyl group,
2-naphthyl group,
anthryl group,
Benzanthryl group,
A phenanthryl group,
Benzophenanthryl group,
A phenalenyl group,
Pyrenyl group,
Chrysenyl group,
benzochrysenyl group,
A triphenylenyl group,
Benzotriphenylenyl group,
tetracenyl group,
Pentacenyl group,
fluorenyl group,
9,9'-spirobifluorenyl group,
Benzofluorenyl group,
Dibenzofluorenyl group,
fluoranthenyl group,
Benzofluoranthenyl group,
A perylenyl group, or a monovalent aryl group derived by removing one hydrogen atom from a ring structure represented by the following general formulae (TEMP-1) to (TEMP-15).

Substituted aryl groups (specific example group G1B):
o-tolyl group,
m-tolyl group,
p-tolyl group,
para-xylyl group,
meta-xylyl group,
ortho-xylyl group,
para-isopropylphenyl group,
meta-isopropylphenyl group,
ortho-isopropylphenyl group,
para-t-butylphenyl group,
A 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,
naphthylphenyl group, and monovalent groups derived from the ring structures represented by the above general formulae (TEMP-1) to (TEMP-15) in which one or more hydrogen atoms are replaced with substituents.

- "Substituted or unsubstituted heterocyclic group"
The "heterocyclic group" described herein is a cyclic group containing at least one heteroatom as a ring-forming atom. Specific examples of the heteroatom include a nitrogen atom, an oxygen atom, a sulfur atom, a silicon atom, a phosphorus atom, and a boron atom.
The "heterocyclic groups" described herein are either monocyclic or fused ring groups.
The "heterocyclic group" described herein may be 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 this specification include the following unsubstituted heterocyclic group (specific example group G2A) and substituted heterocyclic group (specific example group G2B). (Here, the term "unsubstituted heterocyclic group" refers to the case where the "substituted or unsubstituted heterocyclic group" is an "unsubstituted heterocyclic group", and the term "substituted heterocyclic group" refers to the case where the "substituted or unsubstituted heterocyclic group" is a "substituted heterocyclic group".) In this specification, the term "heterocyclic group" simply includes both an "unsubstituted heterocyclic group" and a "substituted heterocyclic group".
The term "substituted heterocyclic group" refers to a group in which one or more hydrogen atoms of an "unsubstituted heterocyclic group" are replaced with a substituent. Specific examples of the "substituted heterocyclic group" include the groups in which the hydrogen atoms of the "unsubstituted heterocyclic group" in the specific example group G2A below are replaced, and the examples of the substituted heterocyclic group in the specific example group G2B below are exemplified. The examples of the "unsubstituted heterocyclic group" and the examples of the "substituted heterocyclic group" listed here are merely examples, and the "substituted heterocyclic group" described in this specification also includes the groups in the "substituted heterocyclic group" in the specific example group G2B in which a hydrogen atom bonded to a ring-forming atom of the heterocyclic group itself is further replaced with a substituent, and the "substituted heterocyclic group" in the specific example group G2B in which a hydrogen atom of a substituent is further replaced with a substituent.

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

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

Unsubstituted heterocyclic groups containing a nitrogen atom (specific example group G2A1):
Pyrrolyl group,
imidazolyl group,
A pyrazolyl group,
A triazolyl group,
Tetrazolyl group,
oxazolyl group,
an isoxazolyl group,
oxadiazolyl group,
A thiazolyl group,
isothiazolyl group,
A thiadiazolyl group,
Pyridyl group,
pyridazinyl group,
pyrimidinyl group,
A pyrazinyl group,
Triazinyl group,
Indolyl groups,
isoindolyl group,
Indolizinyl group,
A quinolizinyl group,
A quinolyl group,
isoquinolyl group,
Cinnolyl group,
phthalazinyl group,
A quinazolinyl group,
A quinoxalinyl group,
Benzimidazolyl group,
Indazolyl group,
A phenanthrolinyl group,
A phenanthridinyl group,
acridinyl group,
A phenazinyl group,
A carbazolyl group,
Benzocarbazolyl group,
morpholino group,
phenoxazinyl group,
A phenothiazinyl group,
Azacarbazolyl and diazacarbazolyl groups.

Unsubstituted heterocyclic groups containing an oxygen atom (specific example group G2A2):
Furyl group,
oxazolyl group,
an isoxazolyl group,
oxadiazolyl group,
xanthenyl group,
benzofuranyl group,
isobenzofuranyl group,
Dibenzofuranyl group,
naphthobenzofuranyl group,
benzoxazolyl group,
benzoisoxazolyl group,
phenoxazinyl group,
morpholino group,
Dinaphthofuranyl group,
azadibenzofuranyl group,
diazadibenzofuranyl group,
Azanaphthobenzofuranyl group, and diazanaphthobenzofuranyl group.

Unsubstituted heterocyclic groups containing a sulfur atom (specific example group G2A3):
A thienyl group,
A thiazolyl group,
isothiazolyl group,
A thiadiazolyl group,
Benzothiophenyl group (benzothienyl group),
isobenzothiophenyl group (isobenzothienyl group),
Dibenzothiophenyl group (dibenzothienyl group),
Naphthobenzothiophenyl group (naphthobenzothienyl group),
benzothiazolyl group,
Benzisothiazolyl group,
A phenothiazinyl group,
Dinaphthothiophenyl group (dinaphthothienyl group),
Azadibenzothiophenyl group (azadibenzothienyl group),
Diazadibenzothiophenyl group (diazadibenzothienyl group),
Azanaphthobenzothiophenyl group (azanaphthobenzothienyl group), and diazanaphthobenzothiophenyl group (diazanaphthobenzothienyl group).

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

In the general formulae (TEMP-16) to (TEMP-33), X _A and Y _A are each independently an oxygen atom, a sulfur atom, NH, or _CH2 , provided that at least one of X _A and Y _A is an oxygen atom, a sulfur atom, or NH.
In the general formulae (TEMP-16) to (TEMP-33), when at least one of _XA and _YA is NH or _CH2 , the monovalent heterocyclic group derived from the ring structure represented by the general formulae (TEMP-16) to (TEMP-33) includes a monovalent group obtained by removing one hydrogen atom from the NH or _CH2 .

Substituted heterocyclic groups containing a nitrogen atom (specific example group G2B1):
A (9-phenyl)carbazolyl group,
A (9-biphenylyl)carbazolyl group,
(9-phenyl)phenylcarbazolyl group,
(9-naphthyl)carbazolyl group,
diphenylcarbazol-9-yl group,
A phenylcarbazol-9-yl group,
methylbenzimidazolyl group,
Ethyl benzimidazolyl group,
phenyltriazinyl group,
Biphenylyltriazinyl group,
diphenyltriazinyl group,
a phenylquinazolinyl group, and a biphenylylquinazolinyl group.

Substituted heterocyclic groups containing an oxygen atom (specific example group G2B2):
phenyldibenzofuranyl group,
methyldibenzofuranyl group,
The t-butyldibenzofuranyl group, and the monovalent radical of spiro[9H-xanthene-9,9'-[9H]fluorene].

Substituted heterocyclic groups containing a sulfur atom (specific example group G2B3):
Phenyldibenzothiophenyl group,
methyldibenzothiophenyl group,
The t-butyldibenzothiophenyl group, and the monovalent radical of spiro[9H-thioxanthene-9,9'-[9H]fluorene].

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

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

- "Substituted or unsubstituted alkyl group"
Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification include the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B). (Here, the unsubstituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group", and the substituted alkyl group refers to the case where the "substituted or unsubstituted alkyl group" is a "substituted alkyl group".) Hereinafter, when the term "alkyl group" is simply mentioned, it includes both the "unsubstituted alkyl group" and the "substituted alkyl group".
The term "substituted alkyl group" refers to 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 the following "unsubstituted alkyl group" (specific example group G3A) in which one or more hydrogen atoms are replaced with a substituent, and the examples of the substituted alkyl group (specific example group G3B). In this specification, the alkyl group in the "unsubstituted alkyl group" refers to a chain-like alkyl group. Therefore, the "unsubstituted alkyl group" includes a straight-chain "unsubstituted alkyl group" and a branched "unsubstituted alkyl group". Note that the examples of the "unsubstituted alkyl group" and the examples of the "substituted alkyl group" listed here are merely examples, and the "substituted alkyl group" described in this specification also includes a group in which a hydrogen atom of the alkyl group itself in the "substituted alkyl group" in the specific example group G3B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkyl group" in the specific example group G3B is further replaced with a substituent.

Unsubstituted alkyl groups (specific example group G3A):
Methyl group,
Ethyl group,
n-propyl group,
isopropyl group,
n-butyl group,
isobutyl group,
s-Butyl group, and t-butyl group.

Substituted alkyl groups (specific example group G3B):
Heptafluoropropyl group (including isomers),
pentafluoroethyl group,
A 2,2,2-trifluoroethyl group, and a trifluoromethyl group.

- "Substituted or unsubstituted alkenyl group"
Specific examples (specific example group G4) of the "substituted or unsubstituted alkenyl group" described in this specification include the following unsubstituted alkenyl group (specific example group G4A) and substituted alkenyl group (specific example group G4B). (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" refers to the case where the "substituted or unsubstituted alkenyl group" is a "substituted alkenyl group".) In this specification, when the term "alkenyl group" is simply used, it includes both an "unsubstituted alkenyl group" and a "substituted alkenyl group".
The term "substituted alkenyl group" refers to a group in which one or more hydrogen atoms in an "unsubstituted alkenyl group" are replaced with a substituent. Specific examples of the "substituted alkenyl group" include the following "unsubstituted alkenyl group" (specific example group G4A) having a substituent, and the examples of substituted alkenyl groups (specific example group G4B). Note that the examples of the "unsubstituted alkenyl group" and the examples of the "substituted alkenyl group" listed here are merely examples, and the "substituted alkenyl group" described in this specification also includes a group in which a hydrogen atom of the alkenyl group itself in the "substituted alkenyl group" in specific example group G4B is further replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted alkenyl group" in specific example group G4B is further replaced with a substituent.

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

Substituted alkenyl groups (specific example group G4B):
1,3-butadienyl group,
1-methylvinyl group,
1-methylallyl group,
1,1-dimethylallyl group,
2-methylallyl group, and 1,2-dimethylallyl group.

- "Substituted or unsubstituted alkynyl group"
Specific examples (specific example group G5) of the "substituted or unsubstituted alkynyl group" described in this specification include the following unsubstituted alkynyl groups (specific example group G5A). (Here, the unsubstituted alkynyl group refers to the case where the "substituted or unsubstituted alkynyl group" is an "unsubstituted alkynyl group.") Hereinafter, when the term "alkynyl group" is simply used, it includes both an "unsubstituted alkynyl group" and a "substituted alkynyl group."
The term "substituted alkynyl group" refers to an "unsubstituted alkynyl group" in which one or more hydrogen atoms have been replaced with a substituent. Specific examples of the "substituted alkynyl group" include the following "unsubstituted alkynyl group" (specific example group G5A) in which one or more hydrogen atoms have been replaced with a substituent.

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

- "Substituted or unsubstituted cycloalkyl groups"
Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group" described in this specification include the following unsubstituted cycloalkyl group (specific example group G6A) and substituted cycloalkyl group (specific example group G6B). (Here, the term "unsubstituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is an "unsubstituted cycloalkyl group", and the term "substituted cycloalkyl group" refers to the case where the "substituted or unsubstituted cycloalkyl group" is a "substituted cycloalkyl group".) In this specification, when the term "cycloalkyl group" is simply mentioned, it includes both an "unsubstituted cycloalkyl group" and a "substituted cycloalkyl group".
The term "substituted cycloalkyl group" refers to 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 the following "unsubstituted cycloalkyl group" (specific example group G6A) in which one or more hydrogen atoms are replaced with a substituent, and the examples of the substituted cycloalkyl group (specific example group G6B). The examples of the "unsubstituted cycloalkyl group" and the examples of the "substituted cycloalkyl group" listed here are merely examples, and the "substituted cycloalkyl group" described in this specification also includes a group in which one or more hydrogen atoms bonded to a carbon atom of the cycloalkyl group itself in the "substituted cycloalkyl group" in the specific example group G6B are replaced with a substituent, and a group in which a hydrogen atom of a substituent in the "substituted cycloalkyl group" in the specific example group G6B is further replaced with a substituent.

Unsubstituted cycloalkyl groups (specific example group G6A):
A cyclopropyl group,
A cyclobutyl group,
Cyclopentyl group,
cyclohexyl group,
1-adamantyl group,
2-adamantyl group,
1-norbornyl group, and 2-norbornyl group.

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

- "A group represented by -Si( _R901 )( _R902 )( _R903 )"
Specific examples (specific example group G7) of the group represented by --Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ) described in this 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)
Here,
G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2.
G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3.
G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
The multiple G1s in -Si(G1)(G1)(G1) are the same as or different from each other.
The multiple G2s in -Si(G1)(G2)(G2) are the same as or different from each other.
The multiple G1s in -Si(G1)(G1)(G2) are the same as or different from each other.
The multiple G2s in —Si(G2)(G2)(G2) are the same as or different from each other.
The multiple G3s in —Si(G3)(G3)(G3) are the same as or different from each other.
The multiple G6s in —Si(G6)(G6)(G6) are the same as or different from each other.

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

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

- "A group represented by -N(R ₉₀₆ )(R ₉₀₇ )"
Specific examples (specific example group G10) of the group represented by -N(R ₉₀₆ )(R ₉₀₇ ) described in this specification include:
-N(G1)(G1),
-N(G2)(G2),
-N (G1) (G2),
-N(G3)(G3), and -N(G6)(G6)
Examples include:
Where:
G1 is a "substituted or unsubstituted aryl group" described in specific example group G1.
G2 is a "substituted or unsubstituted heterocyclic group" described in specific example group G2.
G3 is a "substituted or unsubstituted alkyl group" described in specific example group G3.
G6 is a "substituted or unsubstituted cycloalkyl group" described in specific example group G6.
The multiple G1s in -N(G1)(G1) are the same or different from each other.
The multiple G2s in -N(G2)(G2) are the same or different from each other.
The multiple G3s in -N(G3)(G3) are the same or different.
The multiple G6s in -N(G6)(G6) are the same or different.

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

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

- "Substituted or unsubstituted haloalkyl group"
The term "substituted or unsubstituted haloalkyl group" as used herein means a group in which 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, and also includes a group in which all hydrogen atoms bonded to carbon atoms constituting the alkyl group in the "substituted or unsubstituted alkyl group" are replaced with halogen atoms. The number of carbon atoms in the "unsubstituted haloalkyl group" is 1 to 50, preferably 1 to 30, and more preferably 1 to 18, unless otherwise specified in the present specification. The term "substituted haloalkyl group" means a group in which one or more hydrogen atoms in the "haloalkyl group" are replaced with a substituent. The term "substituted haloalkyl group" as used herein also includes a group in which one or more hydrogen atoms bonded to a carbon atom in the alkyl chain in the "substituted haloalkyl group" are further replaced with a substituent, and a group in which one or more hydrogen atoms of the substituent in the "substituted haloalkyl group" are further replaced with a substituent. Specific examples of the "unsubstituted haloalkyl group" include the examples of the group in which one or more hydrogen atoms in the "alkyl group" (specific example group G3) are replaced with a halogen atom. Haloalkyl groups are sometimes referred to as halogenated alkyl groups.

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

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

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

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

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

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

Unless otherwise specified herein, 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-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, a m-terphenyl-4-yl group, a m-terphenyl-3-yl group, a m-terphenyl-2-yl group, an o-terphenyl-4-yl group, an o-terphenyl-3-yl group, an o-terphenyl-2-yl group, a 1-naphthyl group, a 2-naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a chrysenyl group, a triphenylenyl group, a fluorenyl group, a 9,9'-spirobifluorenyl group, a 9,9-dimethylfluorenyl group, and a 9,9-diphenylfluorenyl group.

The substituted or unsubstituted heterocyclic groups described in this specification, unless otherwise specified in this specification, are preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, a phenanthrolinyl group, a carbazolyl group (a 1-carbazolyl group, a 2-carbazolyl group, a 3-carbazolyl group, a 4-carbazolyl group, or a 9-carbazolyl group), a benzocarbazolyl group, an azacarbazolyl group, a diazacarbazolyl group, a dibenzofuranyl group, a naphthobenzofuranyl group, an azadibenzofuranyl group, a diazadibenzofuranyl group, a dibenzothiophenyl group, a naphthobenzothiophenyl group, an aza Examples of such groups include a dibenzothiophenyl group, a diazadibenzothiophenyl group, a (9-phenyl)carbazolyl group (a (9-phenyl)carbazol-1-yl group, a (9-phenyl)carbazol-2-yl group, a (9-phenyl)carbazol-3-yl group, or a (9-phenyl)carbazol-4-yl group), a (9-biphenylyl)carbazolyl group, a (9-phenyl)phenylcarbazolyl group, a diphenylcarbazol-9-yl group, a phenylcarbazol-9-yl group, a phenyltriazinyl group, a biphenylyltriazinyl group, a diphenyltriazinyl group, a phenyldibenzofuranyl group, and a phenyldibenzothiophenyl group.

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

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

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

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

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

The substituted or unsubstituted alkyl groups described in this specification are preferably methyl groups, ethyl groups, propyl groups, isopropyl groups, n-butyl groups, isobutyl groups, t-butyl groups, and the like, unless otherwise specified in this specification.

- "Substituted or unsubstituted arylene group"
Unless otherwise specified, the "substituted or unsubstituted arylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the aryl ring from the above-mentioned "substituted or unsubstituted aryl group". Specific examples of the "substituted or unsubstituted arylene group" (specific example group G12) include divalent groups derived by removing one hydrogen atom on the aryl ring from the "substituted or unsubstituted aryl group" described in specific example group G1.

- "Substituted or unsubstituted divalent heterocyclic group"
The "substituted or unsubstituted divalent heterocyclic group" described in this specification is, unless otherwise specified, a divalent group derived by removing one hydrogen atom on the heterocycle from the above-mentioned "substituted or unsubstituted heterocyclic group". Specific examples of the "substituted or unsubstituted divalent heterocyclic group" (specific example group G13) include divalent groups derived by removing one hydrogen atom on the heterocycle from the "substituted or unsubstituted heterocyclic group" described in specific example group G2.

- "Substituted or unsubstituted alkylene group"
Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification is a divalent group derived by removing one hydrogen atom on the alkyl chain from the above-mentioned "substituted or unsubstituted alkyl group". Specific examples of the "substituted or unsubstituted alkylene group" (specific example group G14) include divalent groups derived by removing one hydrogen atom on the alkyl chain from the "substituted or unsubstituted alkyl group" described in specific example group G3.

The substituted or unsubstituted arylene groups described in this specification are preferably any of the groups represented by the following general formulas (TEMP-42) to (TEMP-68), unless otherwise specified in this specification.

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

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

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

The substituted or unsubstituted divalent heterocyclic group described in this specification is preferably any one of the groups represented by the following general formulas (TEMP-69) to (TEMP-102), unless otherwise specified in this specification.

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

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

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

・"When bonded to form a ring"
In this specification, the phrase "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle, bond to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other" means the case where "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted monocycle", the case where "one or more of a set consisting of two or more adjacent groups bond to each other to form a substituted or unsubstituted fused ring", or the case where "one or more of a set consisting of two or more adjacent groups are not bonded to each other".
In this specification, the cases where "one or more of a group consisting of two or more adjacent rings are bonded to each other to form a substituted or unsubstituted monocyclic ring" and "one or more of a group consisting of two or more adjacent rings 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") will be explained below. The case of an anthracene compound represented by the following general formula (TEMP-103), in which the mother skeleton is an anthracene ring, will be explained as an example.

For example, in the case where "one or more pairs of adjacent two or more of R ₉₂₁ to R ₉₃₀ are bonded to each other to form a ring", the pair of adjacent two that constitutes one group includes the pair of R ₉₂₁ and R ₉₂₂ , the pair of R ₉₂₂ and R ₉₂₃ , the pair of R ₉₂₃ and R ₉₂₄ , the pair of R ₉₂₄ and R ₉₃₀ , the pair of R ₉₃₀ and R ₉₂₅ , the pair of R ₉₂₅ and R ₉₂₆ , the pair of R ₉₂₆ and R ₉₂₇ , the pair of R ₉₂₇ and R ₉₂₈ , the pair of R ₉₂₈ and R ₉₂₉ , and the pair of R ₉₂₉ and R ₉₂₁ .

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

The case where "a set of two or more adjacent rings" forms a ring includes not only the case where a set of "two" adjacent rings is bonded as in the above example, but also the case where a set of "three or more adjacent rings is bonded. For example, it means the case where R ₉₂₁ and R ₉₂₂ are bonded to each other to form a ring Q _A , and R ₉₂₂ and R ₉₂₃ are bonded to each other to form a ring Q _C , and a set of three adjacent rings (R ₉₂₁ , R ₉₂₂ and R ₉₂₃ ) are bonded to each other to form a ring and are condensed to the anthracene skeleton. In this case, the anthracene compound represented by the general formula (TEMP-103) is represented by the following general formula (TEMP-105). In the following general formula (TEMP-105), ring Q _A and ring Q _C share R ₉₂₂ .

The "monocyclic ring" or "fused ring" formed may be a saturated ring or an unsaturated ring as the structure of only the ring formed. Even when "one of the pairs of two adjacent rings" forms a "monocyclic ring" or a "fused ring", the "monocyclic ring" or the "fused ring" can form a saturated ring or an unsaturated ring. For example, the ring Q _A and the ring Q _B formed in the general formula (TEMP-104) are "monocyclic rings" or "fused rings", respectively. Furthermore, the ring Q _A and the ring Q C formed in the general formula (TEMP-105) are "fused rings". The ring Q A and the ring Q _C in the general formula (TEMP-105) are fused rings by the fusion of the ring Q _A and _{the ring Q C. If} the ring Q _A in the general formula (TEMP-104) is a _{benzene ring, the ring Q A is} a monocyclic ring. When ring Q _{1 A} in the general formula (TEMP-104) is a naphthalene ring, ring Q 1 _A is a fused ring.

The term "unsaturated ring" refers to an aromatic hydrocarbon ring or an aromatic heterocyclic ring. The term "saturated ring" refers to an aliphatic hydrocarbon ring or a non-aromatic heterocyclic ring.
Specific examples of the aromatic hydrocarbon ring include structures in which the groups given as specific examples in specific example group G1 are terminated with a hydrogen atom.
Specific examples of the aromatic heterocycle include structures in which the aromatic heterocyclic groups exemplified as specific examples in the specific example group G2 are terminated with a hydrogen atom.
Specific examples of the aliphatic hydrocarbon ring include structures in which the groups given as specific examples in the specific example group G6 are terminated with a hydrogen atom.
"Forming a ring" means forming a ring only with a plurality of atoms of the mother skeleton, or with a plurality of atoms of the mother skeleton and one or more arbitrary elements. For example, the ring _QA formed by bonding R ₉₂₁ and R ₉₂₂ shown in the general formula (TEMP-104) means a ring formed by the carbon atom of the anthracene skeleton to which R ₉₂₁ is bonded, the carbon atom of the anthracene skeleton to which R ₉₂₂ is bonded, and one or more arbitrary elements. As a specific example, when R ₉₂₁ and R ₉₂₂ form a ring _QA , when the carbon atom of the anthracene skeleton to which R ₉₂₁ is bonded, the carbon atom of the anthracene skeleton to which R ₉₂₂ is bonded, and four carbon atoms form a monocyclic unsaturated ring, the ring formed by R ₉₂₁ and R ₉₂₂ is a benzene ring.

Here, unless otherwise specified in the present specification, the "arbitrary element" is preferably at least one element selected from the group consisting of carbon, nitrogen, oxygen, and sulfur. In the arbitrary element (for example, in the case of a carbon or nitrogen element), a bond that does not form a ring may be terminated with a hydrogen atom or the like, or may be substituted with an "arbitrary substituent" described below. When an arbitrary element other than a carbon element is included, the ring formed is a heterocycle.
Unless otherwise specified in this specification, the "one or more arbitrary elements" constituting the single ring or the condensed ring is preferably 2 or more and 15 or less, more preferably 3 or more and 12 or less, and even more preferably 3 or more and 5 or less.
Unless otherwise specified in this specification, of the "monocyclic ring" and the "condensed ring", the "monocyclic ring" is preferred.
Unless otherwise specified in this specification, of the "saturated ring" and the "unsaturated ring", the "unsaturated ring" is preferred.
Unless otherwise specified in this specification, a "monocyclic ring" is preferably a benzene ring.
Unless otherwise specified in this specification, the "unsaturated ring" is preferably a benzene ring.
When "one or more of a set consisting of two or more adjacent rings""combine with each other to form a substituted or unsubstituted monocyclic ring" or "combine with each other to form a substituted or unsubstituted fused ring", unless otherwise specified in this specification, preferably, one or more of a set consisting of two or more adjacent rings combine with each other to form a substituted or unsubstituted "unsaturated ring" consisting of a plurality of atoms of the parent skeleton and at least one element selected from the group consisting of 1 to 15 carbon elements, nitrogen elements, oxygen elements, and sulfur elements.

When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, the substituent is, for example, the "optional substituent" described later. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above-mentioned section "Substituents described in this specification".
When the above-mentioned "saturated ring" or "unsaturated ring" has a substituent, the substituent is, for example, the "optional substituent" described below. When the above-mentioned "monocyclic ring" or "condensed ring" has a substituent, specific examples of the substituent are the substituents described in the above section "Substituents described in this specification".
The above is an explanation of the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted monocyclic ring" and the case where "one or more pairs of adjacent groups bond with each other to form a substituted or unsubstituted fused ring"("combined to form a ring").

In one embodiment of the present specification, the substituent in the case of "substituted or unsubstituted" (sometimes referred to as "optional substituent" in the present specification) is, for example, an unsubstituted alkyl group having 1 to 50 carbon atoms,
an unsubstituted alkenyl group having 2 to 50 carbon atoms,
an unsubstituted alkynyl group having 2 to 50 carbon atoms,
an unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ),
-O-(R ₉₀₄ ),
-S- (R ₉₀₅ ),
-N(R ₉₀₆ )(R ₉₀₇ ),
Halogen atoms, cyano groups, nitro groups,
a group selected from the group consisting of an unsubstituted aryl group having 6 to 50 ring carbon atoms and an unsubstituted heterocyclic group having 5 to 50 ring atoms,
In the formula, R ₉₀₁ to R ₉₀₇ each independently represent
Hydrogen atoms,
a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms,
a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms,
It is a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.
When two or more R ₉₀₁ are present, the two or more R ₉₀₁ are the same or different from each other,
When two or more R ₉₀₂ are present, the two or more R ₉₀₂ are the same or different from each other,
When two or more R ₉₀₃ are present, the two or more R ₉₀₃ are the same or different from each other,
When two or more R ₉₀₄ are present, the two or more R ₉₀₄ are the same or different from each other,
When two or more R ₉₀₅ are present, the two or more R ₉₀₅ are the same or different from each other,
When two or more R ₉₀₆ are present, the two or more R ₉₀₆ are the same or different from each other,
When two or more R ₉₀₇ are present, the two or more R ₉₀₇ are the same or different.

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

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

Specific examples of each of the above optional substituents are the specific examples of the substituents described in the section "Substituents described in this specification" above.

Unless otherwise specified in this specification, any adjacent substituents may be combined with each other to form a "saturated ring" or an "unsaturated ring", preferably a substituted or unsubstituted saturated 5-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.
Unless otherwise specified in the present specification, the optional substituent may further have a substituent. The substituent that the optional substituent further has is the same as the optional substituent described above.

In this specification, a numerical range expressed using "AA-BB" means a range including the number AA written before "AA-BB" as the lower limit and the number BB written after "AA-BB" as the upper limit.

The compounds of the present invention will be described below.
The compound of the present invention is represented by the above formula (1). The symbols in formula (1) and each formula contained in formula (1) will be explained below. Unless otherwise specified, the same symbols have the same meaning.
The compounds of the present invention represented by formula (1) and the formulae contained in formula (1) described below are sometimes referred to as "invention compounds".

N ^* is the central nitrogen atom.

One of R ^a and R ^b is a substituted or unsubstituted alkyl group having 1 to 30, preferably 1 to 18, more preferably 1 to 10, and even more preferably 1 to 6, carbon atoms, and the other is a substituted or unsubstituted aryl group having 6 to 30, preferably 6 to 25, and more preferably 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30, preferably 5 to 18, and more preferably 5 to 13 ring atoms.
However, R ^a and R ^b may be bonded to each other to form a substituted or unsubstituted ring.

In one embodiment of the present invention, it is preferable that one of R ^a and R ^b is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and the other is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and it is more preferable that one of R ^a and R ^b is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and the other is a substituted or unsubstituted phenyl group.

The unsubstituted alkyl group having 1 to 30 carbon atoms represented by R ^a and R ^b is, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, or a dodecyl group, preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, a t-butyl group, or a pentyl group, more preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, an s-butyl group, or a t-butyl group, and even more preferably a methyl group or a t-butyl group.

The unsubstituted aryl group having 6 to 30 ring carbon atoms represented by R ^a and R ^b is, for example, a phenyl group, a biphenylyl group, a terphenylyl group, a biphenylenyl group, a naphthyl group, an anthryl group, a benzoanthryl group, a phenanthryl group, a benzophenanthryl group, a phenalenyl group, a picenyl group, a pentaphenyl group, a pyrenyl group, a chrysenyl group, a benzochrysenyl group, a fluorenyl group, a fluoranthenyl group, a perylenyl group, or a triphenylenyl group, and preferably a phenyl group, a biphenyl group, The alkyl group is preferably a phenyl group, a terphenylyl group, or a naphthyl group, more preferably a phenyl group, a 2-, 3-, or 4-biphenylyl group, a 2-, 3-, or 4-o-terphenylyl group, a 2-, 3-, or 4-m-terphenylyl group, a 2-, 3-, or 4-p-terphenylyl group, or a 1- or 2-naphthyl group, still more preferably a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group, and particularly preferably a phenyl group.

Examples of the unsubstituted aromatic heterocyclic group having 5 to 30 ring atoms represented by R ^a and R ^b include a pyrrolyl group, a furyl group, a thienyl group, a pyridyl group, an imidazopyridyl group, a pyridazinyl group, a pyrimidinyl group, a pyrazinyl group, a triazinyl group, an imidazolyl group, an oxazolyl group, a thiazolyl group, a pyrazolyl group, an isoxazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a triazolyl group, a tetrazolyl group, aryl group, indolyl group, isoindolyl group, indolizinyl group, quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, indazolyl group, benzoisoxazolyl group, benzoisothiazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group , a phenazinyl group, a phenothiazinyl group, a phenoxazinyl group, a xanthenyl group, a benzofuranyl group, an isobenzofuranyl group, a naphthobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group (benzothienyl group, the same applies below), an isobenzothiophenyl group (isobenzothienyl group, the same applies below), a naphthobenzothiophenyl group (naphthobenzothienyl group, the same applies below), a dibenzothiophenyl group (dibenzothienyl group, the same applies below), or a carbazolyl group, preferably a benzofuranyl group, an isobenzofuranyl group, a naphthobenzofuranyl group, a dibenzofuranyl group, a benzothiophenyl group, an isobenzothiophenyl group, a naphthobenzothiophenyl group, a dibenzothiophenyl group, or a carbazolyl group (9-carbazolyl group, or a 1-, 2-, 3-, or 4-carbazolyl group).

The unsubstituted monocyclic ring formed by R ^a and R ^b is, for example, a benzene ring, a cyclopentane ring, or a cyclohexane ring.
The unsubstituted fused ring formed by R ^a and R ^b is, for example, a naphthalene ring or an anthracene ring.
In addition, when R ^a and R ^b are bonded to each other to form an unsubstituted monocyclic ring or an unsubstituted condensed ring, R ^a and R ^b may form a ring with the fluorene skeleton to which they are bonded to form a spiro ring. The spiro ring is a hydrocarbon ring or a heterocyclic ring, and is selected from a monocyclic ring, a condensed ring, a bridged bicyclo ring, and a bridged tricyclo ring. Examples of substituted or unsubstituted spiro rings are shown below, but are not limited thereto. * indicates the bonding position of the fluorene skeleton to the benzene ring.

In one embodiment of the present invention, it is preferred that R ^a and R ^b do not combine with each other to form a substituted or unsubstituted ring.

One selected from R ² , R ³ , R ⁶ and R ⁷ is a single bond bonding to *1, and R ¹ , R ⁴ , R ⁵ , R ⁸ , and R ² , R ³ , R ⁶ and R ⁷ that are not a single bond bonding to *1 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30, preferably 1 to 18, more preferably 1 to 10, and even more preferably 1 to 6, ring carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 15, preferably 3 to 10, and more preferably 3 to 6 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
Any two adjacent groups selected from R ¹ , R ⁴ , R ⁵ , R ⁸ , and R ² , R ³ , R ⁶ and R ⁷ that are not a single bond are not bonded to each other and therefore do not form a ring.

In one embodiment of the present invention, ^R2 or ^R7 is preferably a single bond bonded to *1.

The details of the unsubstituted alkyl group having 1 to 30 carbon atoms represented by R ¹ , R ⁴ , R ⁵ , R ⁸ , and R ² , R ³ , R ⁶ and R ⁷ which are not single bonds bonded to *1 are as described for R ^a and R ^b .

The unsubstituted cycloalkyl group having 3 to 15 ring carbon atoms represented by R ¹ , R ⁴ , R ⁵ , R ⁸ , and R ² , R ³ , R ⁶ and R ⁷ which are not single bonds bonded to *1 is, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, or a cyclooctyl group, and preferably a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group.

Details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R ¹ , R ⁴ , R ⁵ , R ⁸ , and R ² , R ³ , R ⁶ and R ⁷ which are not a single bond bonded to *1 are as described for R ^a and R ^b , except that the number of ring carbon atoms is 6 to 12.

Details of the unsubstituted heterocyclic group having 5 to 13 ring atoms represented by R ¹ , R ⁴ , R ⁵ , R ⁸ , and R ² , R ³ , R ⁶ and R ⁷ which are not single bonds bonded to *1 are as described for R ^a and R ^b , except that the number of ring atoms is 5 to 13.

The R ¹ , R ⁴ , R ⁵ , R ⁸ , and R ² , R ³ , R ⁶ and R ⁷ which are not single bonds bonded to *1 may all be hydrogen atoms.

R ¹¹ to R ¹⁴ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30, preferably 1 to 18, more preferably 1 to 10, and even more preferably 1 to 6, carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18, preferably 6 to 12, ring carbon atoms.
Adjacent two selected from R ¹¹ to R ¹⁴ are not bonded to each other and therefore do not form a ring.

Details of the unsubstituted alkyl group having 1 to 30 carbon atoms represented by R ¹¹ to R ¹⁴ are as described for R ^a and R ^b .

Details of the unsubstituted aryl group having 6 to 18 ring carbon atoms represented by R ¹¹ to R ¹⁴ are as described for R ^a and R ^b except that the ring carbon atoms are 6 to 18.

All of R ¹¹ to R ¹⁴ may be hydrogen atoms.

L ¹ to L ⁴ each independently represent a single bond or an arylene group having 6 to 30, preferably 6 to 25, and more preferably 6 to 12 ring carbon atoms.

In one embodiment of the present invention, it is preferred that L ¹ and L ² each independently represent a single bond or an arylene group having 6 to 12 ring carbon atoms.
L ¹ may be a single bond and L ² may be a single bond.

In one embodiment of the present invention, ^L3 is preferably a single bond.
In one embodiment of the present invention, ^L4 is preferably a single bond.
In one embodiment of the present invention, ^L3 and ^L4 are preferably a single bond.

The unsubstituted arylene group having 6 to 30 ring carbon atoms represented by L ¹ to L ⁴ is a divalent group obtained by removing one hydrogen atom from an unsubstituted aryl group having 6 to 30 ring carbon atoms. Details of the unsubstituted aryl group having 6 to 30 ring carbon atoms are as described for R ^a and R ^b .

Ar ¹ and Ar ² are groups represented by any one of the following formulas (1a) to (1g).

In formula (1a),
*21 is the bonding position to ^L1 or ^L2 .
One selected from R ¹⁰¹ to R ¹⁰⁵ is a single bond bonding to *22, one selected from R ¹⁰⁶ to R ¹¹⁰ is a single bond bonding to *23, and one selected from R ¹¹¹ to R ¹¹⁵ is a single bond bonding to *24.
The R ¹⁰¹ to R ¹¹⁵ that are not single bonds are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms.
adjacent two of R ¹⁰¹ to R ¹⁰⁵ which are not single bonds are not bonded to each other and therefore do not form a ring;
any two adjacent R ¹⁰⁶ to R ¹¹⁰ which are not single bonds are not bonded to each other and therefore do not form a ring;
Any two adjacent groups selected from R ¹¹¹ to R ¹¹⁵ which are not single bonds are not bonded to each other and therefore do not form a ring.

When ^L1 is a single bond, *21 in the group represented by formula (1a) which is ^Ar1 represents the bonding position to the central nitrogen atom N ^* ;
When ^L2 is a single bond, *21 in the group represented by formula (1a) which is ^Ar2 represents the bonding position to the central nitrogen atom N ^* .

Details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R ¹⁰¹ to R ¹¹⁵ that is not a single bond are as described for R ^a and R ^b , except that the number of carbon atoms is 1 to 10.

Details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R ¹⁰¹ to R ¹¹⁵ are as described for R ^a and R ^b except that the ring carbon atoms are 6 to 12.

All of R ¹⁰¹ to R ¹⁰⁵ that are not single bonds bonded to *22 may be hydrogen atoms, all of R ¹⁰⁶ to R ¹¹⁰ that are not single bonds bonded to *23 may be hydrogen atoms, and all of R ¹¹¹ to R ¹¹⁵ that are not single bonds bonded to *24 may be hydrogen atoms.

m is 0 or 1, n is 0 or 1, and l is 0 or 1.
When m is 0, n is 1, and l is 0 or 1, *22 represents the bonding position to ^L1 or ^L2 (*22 represents *21); when m is 0, n is 0, and l is 1, *23 represents the bonding position to ^L1 or ^L2 (*23 represents *21); and when m is 0, n is 0, and l is 0, *24 represents the bonding position to ^L1 or ^L2 (*24 represents *21).

In one embodiment of the present invention, m is 0, n is 0, and 1 is 0. In this case, *24 represents *21, and formula (1a) is represented by the following formula.

In another embodiment of the present invention, m is 1, n is 0, and l is 0. In this case, *24 represents *22, and formula (1a) is represented by the following formula:

In yet another embodiment of the present invention, m is 0, n is 1, and l is 0. In this case, *22 represents *21, *24 represents *23, and formula (1a) is represented by the following formula:

In yet another embodiment of the present invention, m is 0, n is 0, and l is 1. In this case, *23 represents *21, and formula (1a) is represented by the following formula:

In yet another embodiment of the present invention, m is 1, n is 1, and l is 0. In this case, *24 represents *23, and formula (1a) is represented by the following formula:

In yet another embodiment of the present invention, m is 1, n is 0, and l is 1. In this case, *23 represents *22, and formula (1a) is represented by the following formula:

In yet another embodiment of the present invention, m is 0, n is 1, and l is 1. In this case, *22 represents *21, and formula (1a) is represented by the following formula:

In yet another embodiment of the present invention, m is 1, n is 1 and l is 1. In this case, formula (1a) is represented by the following formula:

The group represented by the formula (1a) preferably satisfies at least one of the following (i) to (iii).
(i) R ¹⁰¹ or R ¹⁰⁵ is a single bond bonded to *22; (ii) R ¹⁰⁶ or R ¹¹⁰ is a single bond bonded to *23; (iii) R ¹¹¹ or R ¹¹⁵ is a single bond bonded to *24.

R ¹¹⁶ to R ¹²⁰ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
Any two adjacent groups selected from R ¹¹⁶ to R ¹²⁰ are not bonded to each other and therefore do not form a ring.

Details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R ¹¹⁶ to R ¹²⁰ are as described for R ^a and R ^b , except that the alkyl group has 1 to 10 carbon atoms.

Details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R ¹¹⁶ to R ¹²⁰ are as described for R ^a and R ^b except that the ring carbon atoms are 6 to 12.

Details of the unsubstituted aryl group having 5 to 13 ring carbon atoms represented by R ¹¹⁶ to R ¹²⁰ are as described for R ^a and R ^b except that the number of ring atoms is 5 to 13.

All of R ¹¹⁶ to R ¹²⁰ may be a hydrogen atom.

The group represented by formula (1a) is preferably represented by the following formula: In the following formula, R has been omitted for simplicity.

Equation (1b) is expressed as follows:

In formula (1b),
*25 is the bonding position to ^L1 or ^L2 .
One selected from R ¹²¹ to R ¹²⁸ is a single bond bonded to *26.
The R ¹²¹ to R ¹²⁸ that are not single bonds are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10, preferably 1 to 6, carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms.
Any two adjacent groups selected from R ¹²¹ to R ¹²⁸ that are not single bonds are not bonded to each other and therefore do not form a ring.
provided that when L ¹ is a p-phenylene group and Ar ¹ is represented by formula (1b), one selected from R ¹²¹ , R ¹²⁴ , R ¹²⁵ , and R ¹²⁸ in the group represented by formula (1b) which is bonded to the p-phenylene group is a single bond bonded to *26;
When L ² is a p-phenylene group and Ar ² is represented by formula (1b), one selected from R ¹²¹ , R ¹²⁴ , R ¹²⁵ , and R ¹²⁸ in the group represented by formula (1b) which is bonded to the p-phenylene group is a single bond bonded to *26.

When ^L1 is a single bond, *25 in the group represented by formula (1b) which is ^Ar1 represents the bonding position to the central nitrogen atom N ^* ;
When ^L2 is a single bond, *25 in the group represented by formula (1b) which is ^Ar2 represents the bonding position to the central nitrogen atom N ^* .

Details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R ¹²¹ to R ¹²⁸ are as described for R ^a and R ^b , except that the number of carbon atoms is 1 to 10.
Details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R ¹²¹ to R ¹²⁸ are as described for R ^a and R ^b except that the ring carbon atoms are 6 to 12.

In one embodiment of the present invention, it is preferred that R ¹²¹ is a single bond bonded to *26, and in another embodiment it is preferred that R ¹²² is a single bond bonded to *26.
*All of R ¹²¹ to R ¹²⁸ that are not the single bond bonded to 26 may be hydrogen atoms.

Equation (1c) is expressed as follows:

In formula (1c),
*27 is the bonding position to ^L1 or ^L2 .
One selected from R ¹³¹ to R ¹⁴⁰ is a single bond bonded to *28.
The R ¹³¹ to R ¹⁴⁰ that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10, preferably 1 to 6, carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
Any two adjacent groups selected from R ¹³¹ to R ¹⁴⁰ that are not single bonds are not bonded to each other and therefore do not form a ring.

When ^L1 is a single bond, *27 in the group represented by formula (1c) which is ^Ar1 represents the bonding position to the central nitrogen atom N ^* ;
When ^L2 is a single bond, *27 in the group represented by formula (1c) which is ^Ar2 represents the bonding position to the central nitrogen atom N ^* .

Details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R ¹³¹ to R ¹⁴⁰ are as described for R ^a and R ^b , except that the number of carbon atoms is 1 to 6.
Details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R ¹³¹ to R ¹⁴⁰ are as described for R ^a and R ^b except that the ring carbon atoms are 6 to 12.
In one embodiment of the present invention, it is preferable that R ¹³¹ , in another embodiment, R ¹³² , and in yet another embodiment, R ¹⁴⁰ are a single bond bonded to *28.
*All of R ¹³¹ to R ¹⁴⁰ that are not the single bond bonded to 28 may be hydrogen atoms.

Equation (1d) is expressed as follows:

In formula (1d),
*29 is the bonding position to ^L1 or ^L2 .
One selected from R ¹⁴¹ to R ¹⁵² is a single bond bonded to *30.
The R ¹⁴¹ to R ¹⁵² that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10, preferably 1 to 6, carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
Any two adjacent groups selected from R ¹⁴¹ to R ¹⁵² which are not single bonds are not bonded to each other and therefore do not form a ring structure.

When ^L1 is a single bond, *29 in the group represented by formula (1d) which is ^Ar1 represents the bonding position to the central nitrogen atom N ^* ;
When ^L2 is a single bond, *29 in the group represented by formula (1d) which is ^Ar2 represents the bonding position to the central nitrogen atom N ^* .

Details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R ¹⁴¹ to R ¹⁵² are as described for R ^a and R ^b , except that the number of carbon atoms is 1 to 10.
Details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R ¹⁴¹ to R ¹⁵² are as described for R ^a and R ^b except that the ring carbon atoms are 6 to 12.
*All of R ¹⁴¹ to R ¹⁵² that are not single bonds bonded to 30 may be hydrogen atoms.

Equation (1e) is expressed by the following equation.

In formula (1e),
*31 is the bonding position to ^L1 or ^L2 .
One selected from R ¹⁶¹ to R ¹⁶⁵ is a single bond bonding to *32, and the other selected from R ¹⁶¹ to R ¹⁶⁵ is a single bond bonding to *33.
R ¹⁶¹ to R ¹⁶⁵ which are not a single bond bonded to *32 and are not a single bond bonded to *33 each independently represent a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms, or an unsubstituted phenyl group.
Any two adjacent bonds selected from R ¹⁶¹ to R ¹⁶⁵ that are not a single bond bonded to *32 and that are not a single bond bonded to *33 are not bonded to each other and therefore do not form a ring.

When ^L1 is a single bond, *31 in the group represented by formula (1e) which is ^Ar1 represents the bonding position to the central nitrogen atom N ^* ;
When ^L2 is a single bond, *31 in the group represented by formula (1e) which is ^Ar2 represents the bonding position to the central nitrogen atom N ^* .

The details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R ¹⁶¹ to R ¹⁶⁵ which is not a single bond bonded to the *32 or the *33 are as described for R ^a and R ^b except that the number of carbon atoms is 1 to 10.
Details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R ¹⁴¹ to R ¹⁵² are as described for R ^a and R ^b except that the ring carbon atoms are 6 to 12.
All of R ¹⁶¹ to R ¹⁶⁵ that are not a single bond bonded to *32 and that are not a single bond bonded to said *33 may be hydrogen atoms.

R ¹⁷¹ to R ¹⁷⁵ and R ¹⁸¹ to R ¹⁸⁵ each independently represent a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms, preferably 1 to 6 carbon atoms.
any two adjacent ones selected from R ¹⁷¹ to R ¹⁷⁵ may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore not form a ring;
Any two adjacent groups selected from R ¹⁸¹ to R ¹⁸⁵ may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore not form a ring.

Details of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R ¹⁷¹ to R ¹⁷⁵ and R ¹⁸¹ to R ¹⁸⁵ are as described for R ^a and R ^b , except that the number of carbon atoms is 1 to 10.
All of R ¹⁷¹ to R ¹⁷⁵ and R ¹⁸¹ to R ¹⁸⁵ may be hydrogen atoms.

Formula (1e) includes groups represented by the following formulas (1e-1) to (1e-5), with formula (1e-1), (1e-2) or (1e-4) being preferred.

Equation (1f) is expressed by the following equation.

In formula (1f),
*34 is the bonding position to ^L1 or ^L2 .
X is an oxygen atom, a sulfur atom, or NR ^A.
X is preferably an oxygen atom or NR ^A.

One selected from R ¹⁹¹ to R ¹⁹⁸ and R ^A is a single bond bonded to *35.
The R ^{3 A} that is not a single bond is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.

When ^L1 is a single bond, *34 in the group represented by formula (1f) which is ^Ar1 represents the bonding position to the central nitrogen atom N ^* ;
When ^L2 is a single bond, *34 in the group represented by formula (1f) which is ^Ar2 represents the bonding position to the central nitrogen atom N ^* .

Details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R ^A are the same as those described for R ^a and R ^b , except that the alkyl group has 1 to 6 carbon atoms.
Details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R ^A are the same as those described for R ^a and R ^b , except that the ring carbon atom number is 6 to 12.

The R ¹⁹¹ to R ¹⁹⁸ that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
Any two adjacent groups selected from R ¹⁹¹ to R ¹⁹⁸ that are not single bonds may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore not form a ring.

Details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R ¹⁹¹ to R ¹⁹⁸ that is not a single bond are as described for R ^a and R ^b , except that the number of carbon atoms is 1 to 6.
Details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R ¹⁹¹ to R ¹⁹⁸ which is not a single bond are as described for R ^a and R ^b except that the ring carbon atoms are 6 to 12.
Details of the unsubstituted heterocyclic group having 5 to 13 ring atoms represented by R ¹⁹¹ to R ¹⁹⁸ that is not a single bond are as described for R ^a and R ^b except that the ring atoms are 5 to 13.

*All of R ¹⁹¹ to R ¹⁹⁸ that are not a single bond bonded to 35 may be hydrogen atoms.

When X is an oxygen atom or a sulfur atom, preferably one selected from R ¹⁹¹ to R ¹⁹⁴ is a single bond bonded to *35.
When X is NR ^A , preferably one selected from R ¹⁹¹ to R ¹⁹⁴ and R ^A is a single bond bonded to *35.
It is particularly preferable that R ^A is a single bond or an unsubstituted phenyl group bonded to *35.

Equation (1g) is expressed by the following formula.

In formula (1g),
*36 is the bonding position to ^L1 or ^L2 .
One selected from R ^B , R ^C , and R ²⁰¹ to R ²⁰⁸ is a single bond bonded to *37.
The ^R and ^R that are not single bonds are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
The R ^B and R ^C which are not single bonds may be bonded to each other to form a substituted or unsubstituted ring.

When ^L1 is a single bond, *36 in the group represented by formula (1g) which is ^Ar1 represents the bonding position to the central nitrogen atom N ^* ;
When ^L2 is a single bond, *36 in the group represented by formula (1g) which is ^Ar2 represents the bonding position to the central nitrogen atom N ^* .

In one embodiment of the present invention, R ^B and R ^C are preferably each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a phenyl group.

The details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R ^B and R ^C which are not a single bond are as described for R ^a and R ^b except that the number of carbon atoms is 1 to 6.
The details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R ^B and R ^C that are not a single bond are as described for R ^a and R ^b except that the ring carbon atoms are 6 to 12.
The details of the unsubstituted heterocyclic group having 5 to 13 ring atoms represented by R ^B and R ^C that are not single bonds are as described for R ^a and R ^b except that the number of ring atoms is 5 to 13.
The details of the unsubstituted ring formed by bonding together R ^B and R ^C which are not a single bond are as described for R ^a and R ^b .

The R ²⁰¹ to R ²⁰⁸ that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
However, adjacent two selected from R ²⁰¹ to R ²⁰⁸ which are not single bonds are not bonded to each other and therefore do not form a ring.

Details of the unsubstituted alkyl group having 1 to 6 carbon atoms represented by R ²⁰¹ to R ²⁰⁸ that is not a single bond are as described for R ^a and R ^b , except that the number of carbon atoms is 1 to 6.
Details of the unsubstituted aryl group having 6 to 12 ring carbon atoms represented by R ²⁰¹ to R ²⁰⁸ that is not a single bond are as described for R ^a and R ^b except that the ring carbon atoms are 6 to 12.
The details of the unsubstituted heterocyclic group having 5 to 13 ring atoms represented by R ²⁰¹ to R ²⁰⁸ that is not a single bond are as described for R ^a and R ^b except that the number of ring atoms is 5 to 13.

In one embodiment of the present invention, it is preferable that R ²⁰² or R ²⁰⁷ is a single bond bonded to *37.

In one embodiment of the present invention, at least one of Ar ¹ and Ar ² is preferably a group represented by formula (1a) or (1g).

In one embodiment of the present invention, Ar ¹ or Ar ² is a group represented by formula (1a), and the group represented by formula (1a) preferably satisfies at least one of the following (i) to (iii):
(i) R ¹⁰¹ or R ¹⁰⁵ is a single bond bonded to *22; (ii) R ¹⁰⁶ or R ¹¹⁰ is a single bond bonded to *23; (iii) R ¹¹¹ or R ¹¹⁵ is a single bond bonded to *24.

In one embodiment of the present invention, it is preferable that Ar ¹ or Ar ² is a group represented by formula (1g), and in the group represented by formula (1g), ^R and ^R are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group.

In one embodiment of the present invention, Ar ¹ or Ar ² is a group represented by formula (1g), and in the group represented by formula (1g), it is preferable that R ²⁰² or R ²⁰⁷ is a single bond bonded to *37.

As noted above, the term "hydrogen atom" as used herein includes protium, deuterium, and tritium atoms. Thus, the compounds of the invention may contain naturally occurring deuterium atoms.
Alternatively, a deuterium atom may be intentionally introduced into compound (1) by using a compound in which some or all of the raw material compounds are deuterated. Thus, in one embodiment of the present invention, compound (1) contains at least one deuterium atom. That is, the invention compound may be a compound represented by formula (1) in which at least one of the hydrogen atoms contained in the compound is a deuterium atom.

At least one hydrogen atom selected from the following hydrogen atoms may be a deuterium atom. In the following, "substituted or unsubstituted", the number of carbon atoms and the number of atoms are omitted.
When R ^a and R ^b in formula (1) are an alkyl group, an aryl group, or a heterocyclic group, a hydrogen atom contained therein;
A hydrogen atom represented by R ¹ to R ⁵ , R ⁸ , and R ⁶ and R ⁷ which are not single bonds bonded to *1 in formula (1);
When R ¹ to R ⁵ , R ⁸ , and R ⁶ and R ⁷ which are not single bonds bonded to *1 in formula (1) are an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group, a hydrogen atom possessed by these groups;
A hydrogen atom represented by R ¹¹ to R ¹⁴ in formula (1);
When R ¹¹ to R ¹⁴ in formula (1) are an alkyl group or an aryl group, a hydrogen atom contained therein;
When L ¹ to L ⁴ in formula (1) are arylene groups, a hydrogen atom contained therein;
A hydrogen atom represented by R ¹⁰¹ to R ¹⁰⁵ which are not a single bond bonded to *22, R ¹⁰⁶ to R ¹¹⁰ which are not a single bond bonded to *23, and R ¹¹¹ to R ¹¹⁵ which are not a single bond bonded to *24 in formula (1a);
When R ¹⁰¹ to R ¹⁰⁵ which are not single bonds bonded to *22, R ¹⁰⁶ to R ¹¹⁰ which are not single bonds bonded to *23, and R ¹¹¹ to R ¹¹⁵ which are not single bonds bonded to *24 in formula (1a) are alkyl groups or aryl groups, the hydrogen atoms possessed by these groups;
A hydrogen atom represented by R ¹¹⁶ to R ¹²⁰ in formula (1a);
When R ¹¹⁶ to R ¹²⁰ in the formula (1a) are an alkyl group, an aryl group, or a heterocyclic group, a hydrogen atom contained therein;
a hydrogen atom represented by R ¹²¹ to R ¹²⁸ which is not a single bond bonded to *26 in formula (1b);
When R ¹²¹ to R ¹²⁸ which are not single bonds bonded to *26 in formula (1b) are alkyl groups or aryl groups, a hydrogen atom contained therein;
a hydrogen atom represented by R ¹³¹ to R ¹⁴⁰ which is not a single bond bonded to *28 in formula (1c);
When R ¹³¹ to R ¹⁴⁰ which are not a single bond bonded to *28 in formula (1c) are an alkyl group or an aryl group, a hydrogen atom contained therein;
A hydrogen atom represented by R ¹⁴¹ to R ¹⁵² which is not a single bond bonded to *30 in formula (1d);
When R ¹⁴¹ to R ¹⁵² which are not a single bond bonded to *30 in formula (1d) are an alkyl group or an aryl group, a hydrogen atom contained therein;
A hydrogen atom represented by R ¹⁶¹ to R ¹⁶⁵ which is not a single bond bonded to *32 in formula (1e) and is not a single bond bonded to said *33;
When R ¹⁶¹ to R ¹⁶⁵ which are not a single bond bonded to *32 in formula (1e) and are not a single bond bonded to said *33 are an alkyl group or a phenyl group, a hydrogen atom contained therein;
a hydrogen atom represented by R ¹⁷¹ to R ¹⁷⁵ and R ¹⁸¹ to R ¹⁸⁵ in formula (1e);
When R ¹⁷¹ to R ¹⁷⁵ and R ¹⁸¹ to R ¹⁸⁵ in the formula (1e) are alkyl groups, the hydrogen atoms contained therein are each independently an alkyl group;
When R ^A which is not a single bond bonded to *35 in formula (1f) is an alkyl group or an aryl group, a hydrogen atom contained therein;
A hydrogen atom represented by R ¹⁹¹ to R ¹⁹⁸ which is not a single bond bonded to *35 in formula (1f);
When R ¹⁹¹ to R ¹⁹⁸ which are not single bonds bonded to *35 in formula (1f) are alkyl groups, aryl groups, or heterocyclic groups, a hydrogen atom contained therein;
When ^R and ^R in formula (1g) are an alkyl group, an aryl group, or a heterocyclic group, a hydrogen atom contained therein;
a hydrogen atom represented by R ²⁰¹ to R ²⁰⁸ which is not a single bond bonded to *37 in formula (1g);
When R ²⁰¹ to R ²⁰⁸ which are not single bonds bonded to *37 in formula (1g) are an alkyl group, an aryl group, or a heterocyclic group, a hydrogen atom contained therein.

The deuteration rate of the invention compound depends on the deuteration rate of the raw material compound used. Even if a raw material with a certain deuteration rate is used, a certain proportion of naturally occurring light hydrogen isotopes may be contained. Therefore, the deuteration rate of the invention compound shown below includes a ratio that takes into account trace amounts of naturally occurring isotopes, in addition to the ratio calculated by simply counting the number of deuterium atoms represented by the chemical formula.
The deuteration rate of the compound of the invention is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, still more preferably 10% or more, and even more preferably 50% or more.

The invention compound may be a mixture containing deuterated and non-deuterated compounds, or a mixture of two or more compounds having different deuteration ratios, preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, still more preferably 10% or more, and even more preferably 50% or more, but less than 100%.
In addition, the ratio of the number of deuterium atoms to the total number of hydrogen atoms in the compound of the invention is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, and even more preferably 10% or more and 100% or less.

When the "substituted or unsubstituted XX group" included in the definition of each formula above is a substituted XX group, the details of the substituent are as described in "Substituents when "substituted or unsubstituted" is used", and are preferably an alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 12 ring carbon atoms, or an aromatic heterocyclic group having 5 to 13 ring atoms, and more preferably an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 12 ring carbon atoms. The details of each group are as described above.

A person skilled in the art can easily prepare the compound of the invention by referring to the synthesis examples below and known synthesis methods.

Specific examples of the compound of the invention are shown below, but the invention is not limited to these exemplary compounds.
In the following specific examples, D represents a deuterium atom.

Material for organic EL device The material for organic EL device of the present invention contains the compound of the present invention. The content of the compound of the present invention in the material for organic EL device is 1 mass% or more (including 100%), preferably 10 mass% or more (including 100%), more preferably 50 mass% or more (including 100%), further preferably 80 mass% or more (including 100%), and particularly preferably 90 mass% or more (including 100%). The material for organic EL device of the present invention is useful for manufacturing an organic EL device.

Organic EL device The organic EL device of the present invention comprises an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer comprises a light-emitting layer, and at least one of the organic layers comprises the compound of the present invention.
Examples of the organic layer containing the compound of the invention include, but are not limited to, a hole transport zone (hole injection layer, hole transport layer, electron blocking layer, exciton blocking layer, etc.) provided between the anode and the light emitting layer, a light emitting layer, a spacer layer, an electron transport zone (electron injection layer, electron transport layer, hole blocking layer, etc.) provided between the cathode and the light emitting layer, etc. The compound of the invention is preferably used as a material for the hole transport zone or light emitting layer of a fluorescent or phosphorescent EL device, more preferably as a material for the hole transport zone, even more preferably as a material for the hole injection layer, hole transport layer, electron blocking layer, or exciton blocking layer, and particularly preferably as a material for the hole injection layer or hole transport layer.

The organic EL element of the present invention may be a monochromatic fluorescent or phosphorescent light-emitting element, a fluorescent/phosphorescent hybrid white light-emitting element, a simple type having a single light-emitting unit, or a tandem type having multiple light-emitting units, and is preferably a fluorescent light-emitting element. Here, the term "light-emitting unit" refers to the smallest unit that includes an organic layer, at least one of which is a light-emitting layer, and emits light by recombining injected holes and electrons.

For example, the following device configuration can be given as a representative device configuration of a simple type organic EL device.
(1) Anode/Light-Emitting Unit/Cathode The light-emitting unit may be a multi-layer type having a plurality of phosphorescent or fluorescent light-emitting layers, in which case a spacer layer may be provided between each light-emitting layer to prevent excitons generated in the phosphorescent light-emitting layer from diffusing to the fluorescent light-emitting layer. A typical layer structure of a simple light-emitting unit is shown below. The layers in parentheses are optional.
(a) (hole injection layer/) hole transport layer/fluorescent light-emitting layer/electron transport layer (/electron injection layer)
(b) (hole injection layer/) hole transport layer/first fluorescent-emitting layer/second fluorescent-emitting layer/electron transport layer (/electron injection layer)
(c) (hole injection layer/) hole transport layer/phosphorescent emitting layer/space layer/fluorescent emitting layer/electron transport layer (/electron injection layer)
(d) (hole injection layer/) hole transport layer/first phosphorescent emitting layer/second phosphorescent emitting layer/space layer/fluorescent emitting layer/electron transport layer (/electron injection layer)
(e) (hole injection layer/) hole transport layer/phosphorescent emitting layer/space layer/first fluorescent emitting layer/second fluorescent emitting layer/electron transport layer (/electron injection layer)
(f) (hole injection layer/) hole transport layer/electron blocking layer/fluorescent emitting layer/electron transport layer (/electron injection layer)
(g) (hole injection layer/) hole transport layer/exciton blocking layer/fluorescent emitting layer/electron transport layer (/electron injection layer)
(h) (hole injection layer/) first hole transport layer/second hole transport layer/fluorescent emitting layer/electron transport layer (/electron injection layer)
(i) (hole injection layer/) first hole transport layer/second hole transport layer/fluorescent light-emitting layer/first electron transport layer/second electron transport layer (/electron injection layer)
(j) (hole injection layer/) hole transport layer/fluorescent light-emitting layer/hole blocking layer/electron transport layer (/electron injection layer)
(k) (hole injection layer/) hole transport layer/fluorescent emitting layer/exciton blocking layer/electron transport layer (/electron injection layer)
(l) (hole injection layer/) first hole transport layer/second hole transport layer/first fluorescent emitting layer/second fluorescent emitting layer/first electron transport layer/second electron transport layer (/electron injection layer)
(m) (hole injection layer/) first hole transport layer/second hole transport layer/third hole transport layer/first fluorescent emitting layer/second fluorescent emitting layer/first electron transport layer/second electron transport layer (/electron injection layer)
(n) (hole injection layer/) first hole transport layer/second hole transport layer/third hole transport layer/fluorescent light-emitting layer/first electron transport layer/second electron transport layer (/electron injection layer)

The phosphorescent or fluorescent emitting layers may each emit light of a different color. Specifically, the light emitting unit (f) may have a layer structure such as a hole injection layer/a hole transport layer/a first phosphorescent emitting layer (red light emission)/a second phosphorescent emitting layer (green light emission)/a spacer layer/a fluorescent emitting layer (blue light emission)/an electron transport layer.
An electron blocking layer may be provided between each light-emitting layer and the hole transport layer or between each spacer layer as needed. Also, a hole blocking layer may be provided between each light-emitting layer and the electron transport layer as needed. By providing an electron blocking layer or a hole blocking layer, electrons or holes can be confined within the light-emitting layer, increasing the probability of charge recombination in the light-emitting layer and improving the light-emitting efficiency.

Representative element configurations of the tandem type organic EL element include the following.
(2) Anode/First Light-Emitting Unit/Intermediate Layer/Second Light-Emitting Unit/Cathode Here, the first light-emitting unit and the second light-emitting unit can be, for example, each independently selected from the light-emitting units described above.
The intermediate layer is generally also called an intermediate electrode, intermediate conductive layer, charge generation layer, electron extraction layer, connection layer, or intermediate insulating layer, and can be made of a known material configuration that supplies electrons to the first light-emitting unit and holes to the second light-emitting unit.

Figure 1 is a schematic diagram showing an example of the configuration of an organic EL element of the present invention. The organic EL element 1 has a substrate 2, an anode 3, a cathode 4, and an emitting unit 10 arranged between the anode 3 and the cathode 4. The emitting unit 10 has an emitting layer 5. A hole transport zone 6 (hole injection layer, hole transport layer, etc.) is between the emitting layer 5 and the anode 3, and an electron transport zone 7 (electron injection layer, electron transport layer, etc.) is between the emitting layer 5 and the cathode 4. In addition, an electron blocking layer (not shown) may be provided on the anode 3 side of the emitting layer 5, and a hole blocking layer (not shown) may be provided on the cathode 4 side of the emitting layer 5. This allows electrons and holes to be trapped in the emitting layer 5, further increasing the efficiency of exciton generation in the emitting layer 5.

Figure 2 is a schematic diagram showing another configuration of the organic EL element of the present invention. The organic EL element 11 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 20 disposed between the anode 3 and the cathode 4. The light-emitting unit 20 has a light-emitting layer 5. The hole transport zone disposed between the anode 3 and the light-emitting layer 5 is formed of a hole injection layer 6a, a first hole transport layer 6b, and a second hole transport layer 6c. The electron transport zone disposed between the light-emitting layer 5 and the cathode 4 is formed of a first electron transport layer 7a and a second electron transport layer 7b.

Figure 3 is a schematic diagram showing another configuration of the organic EL element of the present invention. The organic EL element 12 has a substrate 2, an anode 3, a cathode 4, and a light-emitting unit 30 disposed between the anode 3 and the cathode 4. The light-emitting unit 30 has a light-emitting layer 5. The hole transport zone disposed between the anode 3 and the light-emitting layer 5 is formed of a hole injection layer 6a, a first hole transport layer 6b, a second hole transport layer 6c, and a third hole transport layer 6d. The electron transport zone disposed between the light-emitting layer 5 and the cathode 4 is formed of a first electron transport layer 7a and a second electron transport layer 7b.

In the present invention, a host combined with a fluorescent dopant material (fluorescent light-emitting material) is called a fluorescent host, and a host combined with a phosphorescent dopant material is called a phosphorescent host. Fluorescent hosts and phosphorescent hosts are not distinguished only by their molecular structures. In other words, a phosphorescent host means a material that forms a phosphorescent light-emitting layer containing a phosphorescent dopant, and does not mean that it cannot be used as a material that forms a fluorescent light-emitting layer. The same applies to fluorescent hosts.

Substrate The substrate is used as a support for the organic EL element. For example, a plate such as glass, quartz, or plastic can be used as the substrate. A flexible substrate may also be used. For example, a plastic substrate made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, or polyvinyl chloride can be used as the flexible substrate. An inorganic deposition film can also be used.

Anode For the anode formed on the substrate, it is preferable to use a metal, alloy, electrically conductive compound, or a mixture thereof having a large work function (specifically, 4.0 eV or more). Specific examples include indium oxide-tin oxide (ITO), indium oxide-tin oxide containing silicon or silicon oxide, indium oxide-zinc oxide, indium oxide containing tungsten oxide and zinc oxide, and graphene. Other examples include gold (Au), platinum (Pt), nickel (Ni), tungsten (W), chromium (Cr), molybdenum (Mo), iron (Fe), cobalt (Co), copper (Cu), palladium (Pd), titanium (Ti), or nitrides of the above metals (for example, titanium nitride).

These materials are usually formed into films by sputtering. For example, indium oxide-zinc oxide can be formed by sputtering using a target in which 1 to 10 wt % zinc oxide is added to indium oxide, and indium oxide containing tungsten oxide and zinc oxide can be formed by sputtering using a target in which 0.5 to 5 wt % tungsten oxide and 0.1 to 1 wt % zinc oxide are added to indium oxide. Other methods such as vacuum deposition, coating, inkjet, and spin coating may also be used to form the films.

Hole Transport Zone As described above, the organic layer may include a hole transport zone between the anode and the light emitting layer. The hole transport zone is composed of a hole injection layer, a hole transport layer, an electron blocking layer, etc. It is preferable that the hole transport zone contains the invention compound. It is preferable that at least one of these layers constituting the hole transport layer contains the invention compound, and it is more preferable that the invention compound is contained in the hole transport layer.

The hole injection layer formed in contact with the anode is formed using a material that easily injects holes regardless of the work function of the anode, and therefore materials that are commonly used as electrode materials (e.g., metals, alloys, electrically conductive compounds, and mixtures thereof, and elements belonging to Group 1 or Group 2 of the periodic table) can be used.
Materials with small work functions, such as elements belonging to Group 1 or Group 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these, can also be used. When forming an anode using alkali metals, alkaline earth metals, and alloys containing these, a vacuum deposition method or a sputtering method can be used. Furthermore, when using silver paste, a coating method, an inkjet method, or the like can be used.

Hole Injection Layer The hole injection layer is a layer containing a material with high hole injection properties (hole-injecting material) and is formed between the anode and the light-emitting layer, or, if present, between the hole transport layer and the anode.

Examples of hole injection materials that can be used other than the compound of the invention include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, manganese oxide, etc.

The low molecular weight organic compounds 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-phenylamino]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-di Examples of the hole injection layer material include aromatic amine compounds such as 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]benzene (abbreviation: DPA3B), 3-[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA1), 3,6-bis[N-(9-phenylcarbazol-3-yl)-N-phenylamino]-9-phenylcarbazole (abbreviation: PCzPCA2), and 3-[N-(1-naphthyl)-N-(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1).

Polymer compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, polymer compounds such as 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: Poly-TPD) can be used. In addition, polymer compounds to which an acid has been added, such as poly(3,4-ethylenedioxythiophene)/poly(styrenesulfonic acid) (PEDOT/PSS) and polyaniline/poly(styrenesulfonic acid) (PAni/PSS), can also be used.

Furthermore, it is also preferable to use an acceptor material such as a hexaazatriphenylene (HAT) compound represented by the following formula (K).

(In the above formula, R ²²¹ to R ²²⁶ each independently represent a cyano group, -CONH ₂ , a carboxyl group, or -COOR ²²⁷ (R ²²⁷ represents an alkyl group having 1 to 20 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms). In addition, adjacent two selected from R ²²¹ and R ²²² , R ²²³ and R ²²⁴ , and R ²²⁵ and R ²²⁶ may be bonded to each other to form a group represented by -CO-O-CO-.)
Examples of R ²²⁷ include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group, a cyclopentyl group, and a cyclohexyl group.

Hole Transport Layer The hole transport layer is a layer containing a material with high hole transport properties (hole transport material) and is formed between the anode and the light emitting layer, or, if present, between the hole injection layer and the light emitting layer. The invention compound may be used in the hole transport layer alone or in combination with the following compounds:

The hole transport layer may be a single layer structure or a multilayer structure including two or more layers. For example, the hole transport layer may be a two-layer structure including a first hole transport layer (anode side) and a second hole transport layer (cathode side). That is, the hole transport zone may include a first hole transport layer on the anode side and a second hole transport layer on the cathode side. The hole transport layer may also be a three-layer structure including a first hole transport layer, a second hole transport layer, and a third hole transport layer in this order from the anode side. That is, the third hole transport layer may be disposed between the second hole transport layer and the light-emitting layer.
In one embodiment of the present invention, the hole transport layer of the single layer structure is preferably adjacent to the light emitting layer, and the hole transport layer closest to the cathode in the multilayer structure, for example, the second hole transport layer of the two-layer structure or the third hole transport layer of the three-layer structure, is preferably adjacent to the light emitting layer. In another embodiment of the present invention, an electron blocking layer, which will be described later, may be interposed between the hole transport layer and the light emitting layer of the single layer structure, or between the hole transport layer closest to the light emitting layer in the multilayer structure and the light emitting layer.
When the hole transport layer has a two-layer structure, at least one of the first hole transport layer and the second hole transport layer contains the compound of the invention, i.e., the compound of the invention is contained only in the first hole transport layer, only in the second hole transport layer, or both in the first hole transport layer and the second hole transport layer.
In one embodiment of the present invention, the compound of the present invention is preferably contained in the second hole transport layer, i.e., the compound of the present invention is preferably contained only in the second hole transport layer, or the compound of the present invention is preferably contained in both the first hole transport layer and the second hole transport layer.
When the hole transport layer has a three-layer structure, at least one of the first to third hole transport layers contains the compound of the invention. That is, the compound of the invention is contained in only one layer selected from the first to third hole transport layers (only the first hole transport layer, only the second hole transport layer, or only the third hole transport layer), only two layers selected from the first to third hole transport layers (only the first hole transport layer and the second hole transport layer, only the first hole transport layer and the third hole transport layer, or only the second hole transport layer and the third hole transport layer), or all of the first to third hole transport layers.
In one embodiment of the present invention, the compound of the present invention is preferably contained in the third hole transport layer, i.e., the compound of the present invention is preferably contained only in the third hole transport layer, or the compound of the present invention is preferably contained in the third hole transport layer and one or both of the first hole transport layer and the second hole transport layer.
In one embodiment of the present invention, the invention compound contained in each of the hole transport layers is preferably a protium compound from the viewpoint of production cost. The protium compound is an invention compound in which all hydrogen atoms are protium atoms.
Therefore, the present invention includes an organic EL device in which one or both of the first hole transport layer and the second hole transport layer (in the case of a two-layer structure) and at least one of the first to third hole transport layers contain an invention compound substantially composed of protium compounds. The term "invention compound substantially composed of protium compounds" means that the content of protium compounds in the total amount of the invention compound is 90 mol % or more, preferably 95 mol % or more, and more preferably 99 mol % or more (each including 100%).

As the hole transport layer material other than the compound of the present invention, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used.
Examples of aromatic amine compounds include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB), 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), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The above compounds have a hole mobility of 10 ^-6 cm ² /Vs or more.

Examples of carbazole derivatives include 4,4'-di(9-carbazolyl)biphenyl (abbreviation: CBP), 9-[4-(9-carbazolyl)phenyl]-10-phenylanthracene (abbreviation: CzPA), and 9-phenyl-3-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: PCzPA).
Examples of anthracene derivatives include 2-t-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-BuDNA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), and 9,10-diphenylanthracene (abbreviation: DPAnth).
Polymer compounds such as poly(N-vinylcarbazole) (abbreviation: PVK) and poly(4-vinyltriphenylamine) (abbreviation: PVTPA) can also be used.
However, compounds other than those mentioned above may be used as long as they have a higher hole transporting property than an electron transporting property.

In the organic EL element of the present invention having a two-layer hole transport layer, the first hole transport layer preferably contains one or more compounds represented by the following formula (11) or formula (12).
In the organic EL element of the present invention having a three-layer hole transport layer structure, it is preferable that one or both of the first hole transport layer and the second hole transport layer contain one or more compounds represented by the following formula (11) or (12).
In the organic EL element of the present invention having a hole transport layer of an n-layer structure (n is an integer of 4 or more), it is preferable that at least one of the first hole transport layer to the (n-1)th hole transport layer contains one or more compounds represented by the following formula (11) or formula (12).

[In the formula (11) and formula (12),
L ^A1 , L ^B1 , L ^C1 , L ^A2 , L ^B2 , L ^C2 and L ^D2 each independently represent a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
k is 1, 2, 3 or 4;
When k is 1, L ^E2 is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms;
When k is 2, 3, or 4, 2, 3, or 4 L ^E2 are identical or different from each other;
when k is 2, 3 or 4, multiple L ^E2s are bonded to each other to form a substituted or unsubstituted monocycle, bonded to each other to form a substituted or unsubstituted fused ring, or are not bonded to each other,
L ^E2 which does not form a monocycle and does not form a condensed ring is a substituted or unsubstituted arylene group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted divalent heterocyclic group having 5 to 50 ring atoms,
A ¹ , B ¹ , C ¹ , A ² , B ² , C ² and D ² each independently represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or -Si(R' ₉₀₁ )(R' ₉₀₂ )(R' ₉₀₃ );
R' ₉₀₁ , R' ₉₀₂ and R' ₉₀₃ each independently represent a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms;
When a plurality of R' ₉₀₁ are present, the plurality of R' ₉₀₁ are the same or different,
When a plurality of R' ₉₀₂ are present, the plurality of R' ₉₀₂ are the same or different,
When a plurality of R' ₉₀₃ are present, the plurality of R' ₉₀₃ are the same or different.]

In formula (11) and formula (12), A1, B1, C1, A2, B2, C2, and D2 are preferably each independently selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.
More preferably, at least one of A1, B1, and C1 in formula (11), and at least one of A2, B2, C2, and D2 in formula (12) are a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibenzofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

The fluorenyl group which A1, B1, C1, A2, B2, C2, and D2 may have a substituent at the 9-position, for example, a 9,9-dimethylfluorenyl group or a 9,9-diphenylfluorenyl group. In addition, the substituents at the 9-position may form a ring together, for example, a fluorene skeleton or a xanthene skeleton together.

L ^A1 , L ^B1 , L ^C1 , L ^A2 , L ^B2 , L ^C2 and L ^D2 are preferably each independently a single bond or a substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms.

Specific examples of compounds represented by formula (11) and formula (12) include the following compounds.

Dopant material of the light-emitting layer The light-emitting layer is a layer containing a highly light-emitting material (dopant material), and various materials can be used. For example, fluorescent materials and phosphorescent materials can be used as dopant materials. Fluorescent materials are compounds that emit light from a singlet excited state, and phosphorescent materials are compounds that emit light from a triplet excited state.
In one embodiment of the organic EL device according to the present invention, the light-emitting layer is a single layer.
In another embodiment of the organic EL element according to the present invention, the light-emitting layer includes a first light-emitting layer and a second light-emitting layer.

Blue fluorescent materials that can be used in the light-emitting layer include pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. Specific examples include N,N'-bis[4-(9H-carbazol-9-yl)phenyl]-N,N'-diphenylstilbene-4,4'-diamine (abbreviation: YGA2S), 4-(9H-carbazol-9-yl)-4'-(10-phenyl-9-anthryl)triphenylamine (abbreviation: YGAPA), 4-(10-phenyl-9-anthryl)-4'-(9-phenyl-9H-carbazol-3-yl)triphenylamine (abbreviation: PCBAPA), etc.

As a green fluorescent material that can be used in the light-emitting layer, aromatic amine derivatives and the like can be used. Specifically, N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazole-3-amine (abbreviation: 2PCABPhA), N-(9,10-diphenyl-2-anthryl)-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPAPA), N-[ 9,10-bis(1,1'-biphenyl-2-yl)-2-anthryl]-N,N',N'-triphenyl-1,4-phenylenediamine (abbreviation: 2DPABPhA), N-[9,10-bis(1,1'-biphenyl-2-yl)]-N-[4-(9H-carbazol-9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), and the like.

Red fluorescent materials that can be used in the light-emitting layer include tetracene derivatives and diamine derivatives. Specific examples include N,N,N',N'-tetrakis(4-methylphenyl)tetracene-5,11-diamine (abbreviation: p-mPhTD) and 7,14-diphenyl-N,N,N',N'-tetrakis(4-methylphenyl)acenaphtho[1,2-a]fluoranthene-3,10-diamine (abbreviation: p-mPhAFD).

In one aspect of the present invention, it is preferable that the light-emitting layer contains a fluorescent material (fluorescent dopant material).

Metal complexes such as iridium complexes, osmium complexes, and platinum complexes are used as blue phosphorescent materials that can be used in the light-emitting layer. Specifically, bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) tetrakis(1-pyrazolyl)borate (abbreviation: FIr6), bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviation: FIrpic), bis[2-(3',5'bistrifluoromethylphenyl)pyridinato-N,C2']iridium(III) picolinate (abbreviation: Ir(CF3ppy)2(pic)), bis[2-(4',6'-difluorophenyl)pyridinato-N,C2']iridium(III) acetylacetonate (abbreviation: FIracac), and the like can be mentioned.

Iridium complexes are used as green phosphorescent materials that can be used in the light-emitting layer. Examples include tris(2-phenylpyridinato-N,C2')iridium(III) (abbreviation: Ir(ppy)3), bis(2-phenylpyridinato-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(ppy)2(acac)), bis(1,2-diphenyl-1H-benzimidazolato)iridium(III) acetylacetonate (abbreviation: Ir(pbi)2(acac)), and bis(benzo[h]quinolinato)iridium(III) acetylacetonate (abbreviation: Ir(bzq)2(acac)).

Metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used as red phosphorescent materials that can be used in the light-emitting layer. Specific examples of the organic metal complex include bis[2-(2'-benzo[4,5-α]thienyl)pyridinato-N,C3']iridium(III) acetylacetonate (abbreviation: Ir(btp)2(acac)), bis(1-phenylisoquinolinato-N,C2')iridium(III) acetylacetonate (abbreviation: Ir(piq)2(acac)), (acetylacetonato)bis[2,3-bis(4-fluorophenyl)quinoxalinato]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), and 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation: PtOEP).

In addition, rare earth metal complexes such as tris(acetylacetonato)(monophenanthroline)terbium(III) (abbreviation: Tb(acac)3(Phen)), tris(1,3-diphenyl-1,3-propandionato)(monophenanthroline)europium(III) (abbreviation: Eu(DBM)3(Phen)), and tris[1-(2-thenoyl)-3,3,3-trifluoroacetonato](monophenanthroline)europium(III) (abbreviation: Eu(TTA)3(Phen)) can be used as phosphorescent materials because they emit light from rare earth metal ions (electron transition between different multiplicities).

The light-emitting layer may have a structure in which the above-mentioned dopant material is dispersed in another material (host material). It is preferable to use a material having a lower lowest unoccupied molecular orbital (LUMO) level and a lower highest occupied molecular orbital (HOMO) level than the dopant material.

Examples of the host material include (1) metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes;
(2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, and phenanthroline derivatives,
(3) Condensed aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, and chrysene derivatives;
(4) An aromatic amine compound such as a triarylamine derivative or a condensed polycyclic aromatic amine derivative is used.

For example, metal complexes such as tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum(III) (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium(II) (abbreviation: BeBq2), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ);
Heterocyclic compounds such as 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(p-tert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-biphenylyl)-4-phenyl-5-(4-tert-butylphenyl)-1,2,4-triazole (abbreviation: TAZ), 2,2',2''-(1,3,5-benzenetriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), bathophenanthroline (abbreviation: BPhen), and bathocuproine (abbreviation: BCP);
9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: CzPA), 3,6-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole (abbreviation: DPCzPA), 9,10-bis(3,5-diphenylphenyl)anthracene (abbreviation: DPPA), 9,10-di(2-naphthyl)anthracene (abbreviation: DNA), 2-tert-butyl-9,10-di(2-naphthyl)anthracene (abbreviation: t-Bu DNA), 9,9'-bianthryl (abbreviation: BANT), 9,9'-(stilbene-3,3'-diyl)diphenanthrene (abbreviation: DPNS), 9,9'-(stilbene-4,4'-diyl)diphenanthrene (abbreviation: DPNS2), 3,3',3''-(benzene-1,3,5-triyl)tripylene (abbreviation: TPB3), 9,10-diphenylanthracene (abbreviation: DPAnth), 6,12-dimethoxy-5,11-diphenylchrysene and other condensed aromatic compounds; and N,N-diphenyl-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: CzA1PA), 4-(10-phenyl-9-anthryl)triphenylamine (abbreviation: DPhPA), N,9-diphenyl-N-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazol-3-amine (abbreviation: PCAPA), N,9-diphenyl-N-{4-[4-(10-phenyl-9-anthryl)phenyl]phenyl}-9H-carbazol-3-amine (abbreviation: PCAPBA), N-(9,10-diphenyl-2-anthryl)-N,9-diphenyl-9H Aromatic amine compounds such as N-carbazole-3-amine (abbreviation: 2PCAPA), 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB or α-NPD), N,N'-bis(3-methylphenyl)-N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), and 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) can be used. A plurality of types of host materials may be used.

In particular, in the case of blue fluorescent elements, it is preferable to use the following anthracene compounds as host materials.

In one embodiment of the organic EL element according to the present invention, when the light-emitting layer includes a first light-emitting layer and a second light-emitting layer, at least one of the components constituting the first light-emitting layer is different from the components constituting the second light-emitting layer. For example, the dopant material contained in the first light-emitting layer may be different from the dopant material contained in the second light-emitting layer, or the host material contained in the first light-emitting layer may be different from the host material contained in the second light-emitting layer.

In the organic EL element of the present invention, the light-emitting layer may contain a light-emitting compound that exhibits fluorescent emission having a main peak wavelength of 500 nm or less (hereinafter, sometimes simply referred to as a "fluorescent compound").

The method for measuring the main peak wavelength of a compound is as follows. A 5 μmol/L toluene solution of the compound to be measured is prepared and placed in a quartz cell, and the emission spectrum (vertical axis: emission intensity, horizontal axis: wavelength) of this sample is measured at room temperature (300 K). The emission spectrum can be measured using a spectrofluorophotometer (device name: F-7000) manufactured by Hitachi High-Tech Science Corporation. Note that the emission spectrum measuring device is not limited to the device used here.
In the emission spectrum, the peak wavelength at which the emission intensity is maximum is defined as the main peak wavelength. Note that in this specification, the main peak wavelength may be referred to as the fluorescent emission main peak wavelength (FL-peak).

The fluorescent compound may be the dopant material or the host material.

When the light-emitting layer is a single layer, only one of the dopant material and the host material may be the fluorescent compound, or both of them may be the fluorescent compound.
In addition, when the light-emitting layer includes a first light-emitting layer (anode side) and a second light-emitting layer (cathode side), only one of the first light-emitting layer and the second light-emitting layer may contain the fluorescent compound, or both light-emitting layers may contain the fluorescent compound. When the first light-emitting layer includes the fluorescent compound, only one of the dopant material and the host material included in the first light-emitting layer may be the fluorescent compound, or both may be the fluorescent compound. In addition, when the second light-emitting layer includes the fluorescent compound, only one of the dopant material and the host material included in the second light-emitting layer may be the fluorescent compound, or both may be the fluorescent compound.

Electron Transport Layer The electron transport layer is a layer containing a material with high electron transport properties (electron transport material) and is formed between the light emitting layer and the cathode, or, if present, between the electron injection layer and the light emitting layer.
The electron transport layer may be a single-layer structure or a multi-layer structure including two or more layers. For example, the electron transport layer may be a two-layer structure including a first electron transport layer (anode side) and a second electron transport layer (cathode side). In one embodiment of the present invention, the electron transport layer of the single-layer structure is preferably adjacent to the light-emitting layer, and the electron transport layer closest to the anode in the multi-layer structure, for example, the first electron transport layer of the two-layer structure, is preferably adjacent to the light-emitting layer. In another embodiment of the present invention, a hole blocking layer, which will be described later, may be interposed between the electron transport layer of the single-layer structure and the light-emitting layer, or between the electron transport layer closest to the light-emitting layer in the multi-layer structure and the light-emitting layer.

The electron transport layer may contain, for example,
(1) Metal complexes such as aluminum complexes, beryllium complexes, and zinc complexes,
(2) Heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, and phenanthroline derivatives;
(3) Polymer compounds can be used.

Examples of metal complexes include tris(8-quinolinolato)aluminum(III) (abbreviation: Alq), tris(4-methyl-8-quinolinolato)aluminum (abbreviation: Almq3), bis(10-hydroxybenzo[h]quinolinato)beryllium (abbreviation: BeBq ₂ ), bis(2-methyl-8-quinolinolato)(4-phenylphenolato)aluminum(III) (abbreviation: BAlq), bis(8-quinolinolato)zinc(II) (abbreviation: Znq), bis[2-(2-benzoxazolyl)phenolato]zinc(II) (abbreviation: ZnPBO), and bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ).

Examples of heteroaromatic compounds include 2-(4-biphenylyl)-5-(4-tert-butylphenyl)-1,3,4-oxadiazole (abbreviation: PBD), 1,3-bis[5-(ptert-butylphenyl)-1,3,4-oxadiazol-2-yl]benzene (abbreviation: OXD-7), 3-(4-tert-butylphenyl)-4-phenyl-5-(4-biphenylyl)-1,2, Examples of such compounds include 4-triazole (abbreviation: TAZ), 3-(4-tert-butylphenyl)-4-(4-ethylphenyl)-5-(4-biphenylyl)-1,2,4-triazole (abbreviation: p-EtTAZ), bathophenanthroline (abbreviation: BPhen), bathocuproine (abbreviation: BCP), and 4,4'-bis(5-methylbenzoxazol-2-yl)stilbene (abbreviation: BzOs).

Examples of polymer compounds include poly[(9,9-dihexylfluorene-2,7-diyl)-co-(pyridine-3,5-diyl)] (abbreviation: PF-Py) and poly[(9,9-dioctylfluorene-2,7-diyl)-co-(2,2'-bipyridine-6,6'-diyl)] (abbreviation: PF-BPy).

The above-mentioned materials have an electron mobility of 10 ⁻⁶ cm ² /Vs or more. Note that materials other than the above-mentioned materials may be used for the electron transport layer as long as they have a higher electron transport property than a hole transport property.

Electron injection layer The electron injection layer is a layer containing a material with high electron injection properties. For the electron injection layer, alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), rare earth metals such as europium (Eu), ytterbium (Yb), and compounds containing these metals can be used. Examples of such compounds include alkali metal oxides, alkali metal halides, alkali metal-containing organic complexes, alkaline earth metal oxides, alkaline earth metal halides, alkaline earth metal-containing organic complexes, rare earth metal oxides, rare earth metal halides, and rare earth metal-containing organic complexes. In addition, a mixture of a plurality of these compounds can also be used.
Alternatively, a material having electron transport properties containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically, a material containing magnesium (Mg) in Alq, etc., 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 has excellent electron injection and electron transport properties because the organic compound receives electrons from the electron donor. In this case, the organic compound is preferably a material that is excellent in transporting the received electrons, and specifically, for example, the above-mentioned materials constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) can be used. The electron donor may be any material that exhibits electron donating properties to the organic compound. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples of such materials include lithium, cesium, magnesium, calcium, erbium, and ytterbium. In addition, alkali metal oxides and alkaline earth metal oxides are preferred, and examples of such materials include lithium oxide, calcium oxide, and barium oxide. In addition, a Lewis base such as magnesium oxide can also be used. In addition, an organic compound such as tetrathiafulvalene (abbreviation: TTF) can also be used.

Cathode For the cathode, it is preferable to use a metal, alloy, electrically conductive compound, or mixture thereof having a small work function (specifically, 3.8 eV or less). Specific examples of such a cathode material include elements belonging to Group 1 or Group 2 of the periodic table, i.e., alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), and alloys containing these (e.g., MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.
When an alkali metal, an alkaline earth metal, or an alloy containing these is used to form a cathode, a vacuum deposition method or a sputtering method can be used. When a silver paste or the like is used, a coating method or an inkjet method can be used.
By providing an electron injection layer, the cathode can be formed using various conductive materials, such as Al, Ag, ITO, graphene, indium oxide-tin oxide containing silicon or silicon oxide, regardless of the magnitude of the work function. These conductive materials can be formed into films by a sputtering method, an inkjet method, a spin coating method, or the like.

Insulating Layer Organic EL elements are prone to pixel defects due to leakage and short circuits because an electric field is applied to an ultra-thin film. To prevent this, an insulating layer made of an insulating thin film may be inserted between a pair of electrodes.
Examples of materials used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, titanium oxide, silicon oxide, germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, etc. Mixtures or laminates of these materials may also be used.

The space layer is a layer provided between a fluorescent light-emitting layer and a phosphorescent light-emitting layer for the purpose of preventing excitons generated in the phosphorescent light-emitting layer from diffusing into the fluorescent light-emitting layer or for the purpose of adjusting the carrier balance, for example, when a fluorescent light-emitting layer and a phosphorescent light-emitting layer are laminated. The space layer can also be provided between a plurality of phosphorescent light-emitting layers.
Since the spacer layer is provided between the light-emitting layers, it is preferable that the spacer layer is made of a material having both electron transport properties and hole transport properties. In addition, in order to prevent the diffusion of triplet energy in the adjacent phosphorescent light-emitting layer, it is preferable that the triplet energy is 2.6 eV or more. Materials used for the spacer layer include the same materials as those used for the hole transport layer described above.

Blocking layer A blocking layer such as an electron blocking layer, a hole blocking layer, or an exciton blocking layer may be provided adjacent to the light-emitting layer. The electron blocking layer is a layer that prevents electrons from leaking from the light-emitting layer to the hole transport layer, and the hole blocking layer is a layer that prevents holes from leaking from the light-emitting layer to the electron transport layer. The exciton blocking layer has the function of preventing excitons generated in the light-emitting layer from diffusing to surrounding layers and trapping the excitons within the light-emitting layer.

Each layer of the organic EL element can be formed by a conventionally known deposition method, coating method, etc. For example, it can be formed by a conventional deposition method such as vacuum deposition method or molecular beam deposition method (MBE method), or a coating method such as dipping method, spin coating method, casting method, bar coating method, roll coating method, etc. using a solution of a compound that forms the layer.

There are no particular restrictions on the thickness of each layer, but generally, if the thickness is too thin, defects such as pinholes are likely to occur, while if it is too thick, a high driving voltage is required, resulting in poor efficiency, so the thickness is usually 5 nm to 10 μm, and 10 nm to 0.2 μm is more preferable.

In the organic EL element of the present invention having a two-layer or three-layer hole transport layer, the total thickness of the first hole transport layer and the second hole transport layer is preferably 30 nm or more and 150 nm or less, more preferably 40 nm or more and 130 nm or less.
In one embodiment of the present invention, the thickness of the second hole transport layer in the two-layer structure or three-layer structure is preferably 5 nm or more, more preferably 20 nm or more, even more preferably 25 nm or more, particularly preferably 35 nm or more, and is preferably 100 nm or less.
In one embodiment of the present invention, the thickness of the hole transport layer adjacent to the light-emitting layer is preferably 5 nm or more, more preferably 20 nm or more, even more preferably 25 nm or more, particularly preferably 30 nm or more, and is preferably 100 nm or less.
In the organic EL element having a hole transport layer of a two-layer structure or a three-layer structure of the present invention, the ratio of the thickness D2 of the second hole transport layer to the thickness D1 of the first hole transport layer is preferably 0.3<D2/D1<4.0, more preferably 0.5<D2/D1<3.5, and even more preferably 0.75<D2/D1<3.0.

As a preferred embodiment of the organic EL element of the present invention, for example,
(1) An organic EL device having a two-layer structure of hole transport layers: a first embodiment in which the second hole transport layer contains the compound of the invention and the first hole transport layer does not contain the compound of the invention;
A second embodiment, in which both the first hole transport layer and the second hole transport layer comprise an inventive compound;
A third embodiment in which the first hole transport layer comprises an inventive compound and the second hole transport layer does not comprise an inventive compound;
(2) A fourth embodiment of an organic EL device having a three-layer structure of hole transport layers, in which the first hole transport layer contains the compound of the invention, and the second and third hole transport layers do not contain the compound of the invention;
A fifth embodiment in which the second hole transport layer comprises an inventive compound and the first and third hole transport layers do not comprise an inventive compound;
A sixth embodiment in which the third hole transport layer comprises an inventive compound and the first and second hole transport layers do not comprise an inventive compound;
the seventh embodiment, in which the first and second hole transport layers comprise an inventive compound and the third hole transport layer does not comprise an inventive compound;
an eighth embodiment, in which the first and third hole transport layers comprise an inventive compound and the second hole transport layer does not comprise an inventive compound;
a tenth embodiment, in which the second and third hole transport layers comprise an inventive compound and the first hole transport layer does not comprise an inventive compound;
The tenth embodiment, in which all of the first to third hole transport layers contain the compound of the invention;

Electronic Device The organic EL element according to one embodiment of the present invention can be used in electronic devices such as display devices and light-emitting devices. Examples of display devices include display components such as organic EL panel modules, televisions, mobile phones, tablets, and personal computers. Examples of light-emitting devices include lighting and vehicle lamps.

The organic EL elements can be used in electronic devices such as display components such as organic EL panel modules, display devices for televisions, mobile phones, personal computers, etc., and light-emitting devices for lighting and vehicle lamps.

The present invention will be described in further detail below using examples, but the present invention is not limited to the following examples.

Invention compounds used in the production of organic EL devices (I) in Examples 1 to 3

Comparative compounds used in the manufacture of organic EL devices (I) of Comparative Examples 1 and 2

Other compounds used in the manufacture of the organic EL devices (I) of Examples 1 to 3 and Comparative Examples 1 and 2

Preparation of Organic EL Element (I) <Example 1>
A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) measuring 25 mm×75 mm×1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.
The glass substrate with the ITO transparent electrode after cleaning was attached to a substrate holder of a vacuum deposition apparatus, and the compound HT-1 and the compound HA were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer having a thickness of 10 nm. The mass ratio of the compound HT-1 to the compound HA (HT-1:HA) was 97:3.
Next, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 40 nm.
Next, the compound Inv-1 was deposited on the first hole transport layer to form a second hole transport layer having a thickness of 40 nm.
Next, the compound HT-2 was deposited on the second hole transport layer to form a third hole transport layer having a thickness of 5 nm.
Next, on the third hole transport layer, the compound BH-1 (host material) and the compound BD-1 (dopant material) were co-deposited to form a first light-emitting layer having a thickness of 20 nm. The mass ratio of the compound BH-1 to the compound BD-1 (BH-1:BD-1) was 99:1.
Next, the compound ET-1 was evaporated onto the light-emitting layer to form a first electron transport layer having a thickness of 5 nm.
Next, the compound ET-2 and Liq were co-deposited on the first electron transport layer to form a second electron transport layer having a thickness of 25 nm. The mass ratio of the compound ET-2 to Liq (ET-2:Liq) was 50:50.
Next, Yb was evaporated onto the second electron transport layer to form an electron injecting electrode having a thickness of 1 nm.
Then, metallic Al was evaporated onto this electron injecting electrode to form a metal cathode having a thickness of 50 nm.
The layer structure of the organic EL element of Example 1 thus obtained is shown below.
ITO (130)/HT-1:HA=97:3 (10)/HT-1 (40)/Inv-1 (40)/HT-2 (5)/BH-1:BD-1=99:1 (20)/ET-1 (5)/ET-2:Liq=50:50 (25)/Yb (1)/Al (50)
In the above layer configuration, the numbers in parentheses are film thicknesses (nm) and the ratios are mass ratios.

<Examples 2 and 3>
Each organic EL element (I) was prepared in the same manner as in Example 1, except that in Example 2, compound Inv-4 was used instead of compound Inv-1, and in Example 3, compound Inv-5 was used instead.

<Comparative Examples 1 and 2>
Each organic E(I)L element was fabricated in the same manner as in Example 1, except that in Comparative Example 1, comparative compound Ref-1 was used instead of compound Inv-1, and in Comparative Example 2, comparative compound Ref-2 was used.

Evaluation of Organic EL Element (I) The driving voltage and external quantum efficiency of the obtained organic EL element (I) were measured.
(1) Measurement of Driving Voltage The voltage (unit: V) was measured when a voltage was applied to the organic EL element (I) so that the current density was 10 mA/cm ^2. The results are shown in Table 1.
(2) Measurement of external quantum efficiency (EQE) The obtained organic EL element (I) was driven at room temperature with a constant direct current at a current density of 10 mA/ ^cm2 . The luminance was measured using a luminance meter (Spectroluminance Radiometer CS-1000 manufactured by Minolta Co., Ltd.), and the external quantum efficiency (%) was calculated from the results. The results are shown in Table 1.

Invention compounds used in the production of organic EL devices (II) in Examples 4 to 7

Comparative Compounds Used in the Production of Organic EL Device (II) of Comparative Example 2

Other compounds used in the manufacture of the organic EL devices (II) of Examples 4 to 7 and Comparative Example 3

Preparation of Organic EL Element (II) <Example 4>
A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) measuring 25 mm×75 mm×1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.
The glass substrate with the ITO transparent electrode after cleaning was attached to a substrate holder of a vacuum deposition apparatus, and the compound Inv-1 and the compound HA were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer having a thickness of 10 nm. The mass ratio of the compound Inv-1 to the compound HA (Inv-1:HA) was 97:3.
Next, the compound Inv-1 was evaporated onto the hole injection layer to form a first hole transport layer having a thickness of 80 nm.
Next, the compound HT-4 was deposited on the first hole transport layer to form a second hole transport layer having a thickness of 10 nm.
Next, on the second hole transport layer, the compound BH-2 (host material) and the compound BD-2 (dopant material) were co-deposited to form a light-emitting layer having a thickness of 25 nm. The mass ratio of the compound BH-2 to the compound BD-2 (BH-2:BD-2) was 96:4.
Next, the compound ET-3 was evaporated onto the light-emitting layer to form a first electron transport layer having a thickness of 10 nm.
Next, the compound ET-4 was deposited on the first electron transport layer to form a second electron transport layer having a thickness of 15 nm.
Next, LiF was evaporated onto the second electron transport layer to form an electron injecting electrode having a thickness of 1 nm.
Then, metallic Al was evaporated onto this electron injecting electrode to form a metal cathode having a thickness of 50 nm.
The layer structure of the organic EL element (II) of Example 4 thus obtained is shown below.
ITO (130)/Inv-1:HA=97:3 (10)/Inv-1 (80)/HT-4 (10)/BH-2:BD-2=96:4 (25)/ET-3 (10)/ET-4 (15)/LiF (1)/Al (50)
In the above layer configuration, the numbers in parentheses are film thicknesses (nm) and the ratios are mass ratios.

<Examples 5 to 7>
Organic EL elements (II) were prepared in the same manner as in Example 4, except that, instead of compound Inv-1, compound Inv-6 was used in Example 5, compound Inv-7 was used in Example 6, and compound Inv-8 was used in Example 7.

<Comparative Example 3>
Each organic EL device (II) was prepared in the same manner as in Example 4, except that the comparative compound Ref-2 was used instead of the inventive compound Inv-1.

Evaluation of Organic EL Element (II) The driving voltage and external quantum efficiency of the obtained organic EL element (II) were measured in the same manner as for the organic EL element (I). The results are shown in Table 2.

Invention compounds used in the production of organic EL devices (III) of Examples 8 to 17

Comparative compounds used in the manufacture of organic EL devices (III) of Comparative Examples 4 and 5

Other compounds used in the manufacture of organic EL devices in Examples 8 to 17 and Comparative Examples 4 and 5

Preparation of Organic EL Element (III) <Example 8>
A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) measuring 25 mm×75 mm×1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.
The glass substrate with the ITO transparent electrode after cleaning was attached to a substrate holder of a vacuum deposition apparatus, and the compound HT-1 and the compound HA were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer having a thickness of 10 nm. The mass ratio of the compound HT-1 to the compound HA (HT-1:HA) was 97:3.
Next, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 40 nm.
Next, the compound Inv-2 was evaporated onto the first hole transport layer to form a second hole transport layer having a thickness of 45 nm.
Next, the compound HT-6 was evaporated onto the second hole transport layer to form a third hole transport layer having a thickness of 5 nm.
Next, on the third hole transport layer, the compound BH-1 (host material) and the compound BD-3 (dopant material) were co-deposited to form a first light-emitting layer having a thickness of 5 nm. The mass ratio of the compound BH-1 to the compound BD-3 (BH-1:BD-3) was 99:1.
Next, on the first emitting layer, the compound BH-5 (host material) and the compound BD-3 (dopant material) were co-deposited to form a second emitting layer having a thickness of 20 nm. The mass ratio of the compound BH-5 to the compound BD-3 (BH-5:BD-3) was 99:1.
Next, the compound ET-1 was deposited on the second light-emitting layer to form a first electron transport layer having a thickness of 5 nm.
Next, a second electron transport layer having a thickness of 31 nm was formed on the first electron transport layer by co-evaporation of the compounds ET-2 and Liq. The mass ratio of the compounds ET-2 and Liq (ET-2:Liq) was 50:50.
Next, Liq was evaporated onto the second electron transport layer to form an electron injecting electrode having a thickness of 1 nm.
Then, metallic Al was evaporated onto this electron injecting electrode to form a metal cathode having a thickness of 80 nm.
The layer structure of the organic EL element (III) of Example 8 thus obtained is shown below.
ITO (130)/HT-1:HA=97:3 (10)/HT-1 (40)/Inv-2 (45)/HT-6 (5)/BH-1:BD-3=99:1 (5)/BH-5:BD-3=99:1 (20)/ET-1 (5)/ET-2:Liq=50:50 (31)/Liq (1)/Al (80)
In the above layer configuration, the numbers in parentheses are film thicknesses (nm) and the ratios are mass ratios.

<Example 9>
An organic EL element (III) was prepared in the same manner as in Example 8, except that compound Inv-3 was used instead of compound Inv-2.

Example 10
An organic EL element (III) was prepared in the same manner as in Example 8, except that compound Inv-9 was used instead of compound Inv-2.

Example 11
An organic EL element (III) was prepared in the same manner as in Example 8, except that the compound BD-4 was used instead of the compound BD-3.

<Example 12>
An organic EL element (III) was produced in the same manner as in Example 8, except that instead of forming a second light-emitting layer having a thickness of 20 nm by co-depositing compound BH-5 (host material) and compound BD-3 (dopant material) on the first light-emitting layer, a second light-emitting layer having a thickness of 20 nm was formed by co-depositing compound BH-4 (host material), compound BH-7 (host material), and compound BD-3 (dopant material). The mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was 70:30, and the concentration of compound BD-3 was 1 mass% with respect to the entire second light-emitting layer.

<Example 13>
An organic EL element (III) was prepared in the same manner as in Example 12, except that the mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was 50:50.

<Example 14>
An organic EL element (III) was prepared in the same manner as in Example 12, except that the mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was 30:70.

Example 15
An organic EL element (III) was prepared in the same manner as in Example 12, except that the mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was 20:80.

<Example 16>
A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) measuring 25 mm×75 mm×1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.
The glass substrate with the ITO transparent electrode after cleaning was attached to a substrate holder of a vacuum deposition apparatus, and the compound HT-1 and the compound HA were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer having a thickness of 10 nm. The mass ratio of the compound HT-1 to the compound HA (HT-1:HA) was 97:3.
Next, compound HT-1 was deposited on the hole injection layer to form a first hole transport layer having a thickness of 40 nm.
Next, the compound Inv-2 was evaporated onto the first hole transport layer to form a second hole transport layer having a thickness of 45 nm.
Next, the compound HT-2 was deposited on the second hole transport layer to form a third hole transport layer having a thickness of 5 nm.
Next, on the third hole transport layer, the compound BH-3 (host material) and the compound BD-5 (dopant material) were co-deposited to form a first light-emitting layer having a thickness of 5 nm. The mass ratio of the compound BH-3 to the compound BD-5 (BH-3:BD-5) was 99:1.
Next, on the first emitting layer, the compound BH-6 (host material) and the compound BD-5 (dopant material) were co-deposited to form a second emitting layer having a thickness of 20 nm. The mass ratio of the compound BH-6 to the compound BD-5 (BH-6:BD-5) was 99:1.
Next, the compound ET-3 was evaporated onto the second emitting layer to form a first electron transporting layer having a thickness of 10 nm.
Next, the compound ET-4 was deposited on the first electron transport layer to form a second electron transport layer having a thickness of 15 nm.
Then, metallic Al was evaporated onto this electron injecting electrode to form a metal cathode having a thickness of 80 nm.
The layer structure of the thus obtained organic EL element (III) of Example 16 is shown below.
ITO (130)/HT-1:HA=97:3 (10)/HT-1 (40)/Inv-2 (45)/HT-2 (5)/BH-3:BD-5=99:1 (5)/BH-6:BD-5=99:1 (20)/ET-3 (10)/ET-4 (15)/Al (80)
In the above layer configuration, the numbers in parentheses are film thicknesses (nm) and the ratios are mass ratios.

<Example 17>
An organic EL element (III) was prepared in the same manner as in Example 8, except that the compound HT-5 was used instead of the compound HT-1 and the compound Inv-1 was used instead of the compound Inv-2.

<Comparative Examples 4 and 5>
An organic EL element (III) was prepared in the same manner as in Example 8, except that the comparative compound Ref-3 or the comparative compound Ref-4 was used instead of the compound Inv-2.

Evaluation of Organic EL Element (III) The external quantum efficiency of the obtained organic EL element (III) was measured in the same manner as in the organic EL element (I). The results are shown in Table 3.
(3) 95% lifespan (LT95)
The organic EL element (III) thus obtained was driven with a constant direct current at a current density of 50 mA/ ^cm2 , and the time until the luminance decreased to 95% of the initial luminance was measured, which was taken as the 95% lifespan (LT95). The results are shown in Table 3.

Invention compounds used in the manufacture of organic EL devices (IV) of Examples 18 to 34

Comparative Compounds Used in the Production of Organic EL Device (IV) of Comparative Example 6

Other compounds used in the manufacture of organic EL devices in Examples 18 to 34 and Comparative Example 6

Preparation of Organic EL Element (IV) <Example 18>
A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) measuring 25 mm×75 mm×1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.
The glass substrate with the ITO transparent electrode after cleaning was attached to a substrate holder of a vacuum deposition apparatus, and the compound Inv-2 and the compound HA were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer having a thickness of 10 nm. The mass ratio of the compound Inv-2 to the compound HA (Inv-2:HA) was 97:3.
Next, the compound Inv-2 was evaporated onto the hole injection layer to form a first hole transport layer having a thickness of 85 nm.
Next, the compound HT-6 was deposited on the first hole transport layer to form a second hole transport layer having a thickness of 5 nm.
Next, on the second hole transport layer, the compound BH-1 (host material) and the compound BD-3 (dopant material) were co-deposited to form a first light-emitting layer having a thickness of 5 nm. The mass ratio of the compound BH-1 to the compound BD-3 (BH-1:BD-3) was 99:1.
Next, the compound BH-5 (host material) and the compound BD-3 (dopant material) were co-deposited on the first emitting layer to form a second emitting layer having a thickness of 15 nm. The mass ratio of the compound BH-5 to the compound BD-3 (BH-5:BD-3) was 99:1.
Next, the compound ET-1 was deposited on the second light-emitting layer to form a first electron transport layer having a thickness of 5 nm.
Next, a second electron transport layer having a thickness of 31 nm was formed on the first electron transport layer by co-evaporation of the compounds ET-2 and Liq. The mass ratio of the compounds ET-2 and Liq (ET-2:Liq) was 50:50.
Next, Liq was evaporated onto the second electron transport layer to form an electron injecting electrode having a thickness of 1 nm.
Then, metallic Al was evaporated onto this electron injecting electrode to form a metal cathode having a thickness of 80 nm.
The layer structure of the thus obtained organic EL element (IV) of Example 18 is shown below.
ITO (130)/Inv-2:HA=97:3 (10)/Inv-2 (85)/HT-6 (5)/BH-1:BD-3=99:1 (5)/BH-5:BD-3=99:1 (15)/ET-1 (5)/ET-2:Liq=50:50 (31)/Liq (1)/Al (80)
In the above layer configuration, the numbers in parentheses are film thicknesses (nm) and the ratios are mass ratios.

<Examples 19 to 21>
Organic EL elements (IV) were prepared in the same manner as in Example 18, except that, instead of compound Inv-2, compound Inv-4 was used in Example 19, compound Inv-3 was used in Example 20, and compound Inv-9 was used in Example 21.

<Example 22>
An organic EL element (IV) was prepared in the same manner as in Example 18, except that the compound HT-7 was used instead of the compound HT-6.

<Example 23>
An organic EL element (IV) was prepared in the same manner as in Example 18, except that the compound BH-9 was used instead of the compound BH-5.

<Example 24>
An organic EL element (IV) was produced in the same manner as in Example 18, except that compound BH-3 was used instead of compound BH-1, compound BH-6 was used instead of compound BH-5, and compound BD-4 was used instead of compound BD-3.

<Example 25>
A glass substrate (manufactured by Geomatec Co., Ltd.) with an ITO transparent electrode (anode) measuring 25 mm×75 mm×1.1 mm was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.
The glass substrate with the ITO transparent electrode after cleaning was attached to a substrate holder of a vacuum deposition apparatus, and the compound Inv-2 and the compound HA were co-deposited on the surface on which the transparent electrode was formed so as to cover the transparent electrode, thereby forming a hole injection layer having a thickness of 10 nm. The mass ratio of the compound Inv-2 to the compound HA (Inv-2:HA) was 97:3.
Next, the invention compound Inv-2 was evaporated onto the hole injection layer to form a first hole transport layer having a thickness of 85 nm.
Next, the compound HT-8 was evaporated onto the first hole transport layer to form a second hole transport layer having a thickness of 5 nm.
Next, on the second hole transport layer, the compound BH-3 (host material) and the compound BD-5 (dopant material) were co-deposited to form a first light-emitting layer having a thickness of 5 nm. The mass ratio of the compound BH-3 to the compound BD-5 (BH-3:BD-5) was 99:1.
Next, on the first emitting layer, the compound BH-6 (host material) and the compound BD-5 (dopant material) were co-deposited to form a second emitting layer having a thickness of 15 nm. The mass ratio of the compound BH-6 to the compound BD-5 (BH-6:BD-5) was 99:1.
Next, the compound ET-3 was evaporated onto the second emitting layer to form a first electron transporting layer having a thickness of 10 nm.
Next, the compound ET-4 was deposited on the first electron transport layer to form a second electron transport layer having a thickness of 15 nm.
Then, metallic Al was evaporated onto the second electron transport layer to form a metal cathode having a thickness of 80 nm.
The layer structure of the thus obtained organic EL element (IV) of Example 25 is shown below.
ITO (130)/Inv-2:HA=97:3 (10)/Inv-2 (85)/HT-8 (5)/BH-3:BD-5=99:1 (5)/BH-6:BD-5=99:1 (15)/ET-3 (10)/ET-4 (15)/Al (80)
In the above layer configuration, the numbers in parentheses are film thicknesses (nm) and the ratios are mass ratios.

<Example 26>
An organic EL element (IV) was prepared in the same manner as in Example 18, except that the compound HT-9 was used instead of the compound HT-6.

<Example 27>
An organic EL element (IV) was prepared in the same manner as in Example 18, except that the compound HT-10 was used instead of the compound HT-6.

<Example 28>
An organic EL element (IV) was produced in the same manner as in Example 18, except that instead of forming a second light-emitting layer having a thickness of 15 nm by co-depositing compound BH-5 (host material) and compound BD-3 (dopant material) on the first light-emitting layer, a second light-emitting layer having a thickness of 20 nm was formed by co-depositing compound BH-4 (host material), compound BH-7 (host material), and compound BD-3 (dopant material). The mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was 70:30, and the concentration of compound BD-3 was 1 mass% with respect to the entire second light-emitting layer.

<Example 29>
An organic EL element (IV) was produced in the same manner as in Example 28, except that compound HT-7 was used instead of compound HT-6 and the mass ratio of compound BH-4 to compound BH-7 (BH-4:BH-7) was 60:40.

<Example 30>
An organic EL element (IV) was produced in the same manner as in Example 18, except that instead of forming a second light-emitting layer having a thickness of 15 nm by co-depositing compound BH-5 (host material) and compound BD-3 (dopant material) on the first light-emitting layer, a second light-emitting layer having a thickness of 20 nm was formed by co-depositing compound BH-8 (host material), compound BH-5 (host material), and compound BD-3 (dopant material). The mass ratio of compound BH-8 to compound BH-5 (BH-8:BH-5) was 70:30, and the concentration of compound BD-3 was 1 mass% with respect to the entire second light-emitting layer.

<Examples 31 to 34>
Organic EL elements (IV) were prepared in the same manner as in Example 18, except that, instead of the compound HT-6, the compound HT-11 was used in Example 31, the compound HT-4 was used in Example 32, the compound HT-12 was used in Example 33, and the compound HT-13 was used in Example 34.

<Comparative Example 6>
An organic EL element (IV) was produced in the same manner as in Example 17, except that the compound Ref-5 was used instead of the compound Inv-2, and the compound HT-13 was used instead of the compound HT-6.

Evaluation of Organic EL Element (IV) For the obtained organic EL element (IV), the external quantum efficiency was measured in the same manner as for the organic EL element (I), and the 95% lifetime was measured in the same manner as for the organic EL element (III). The results are shown in Table 4.

As is clear from the results in Tables 1 to 4, compounds Inv-1 to Inv-9 provide organic EL elements with lower driving voltages and higher external quantum efficiency than comparison compounds Ref-1 to Ref-5.

Compounds Inv-1 to Inv-9 of the invention synthesized in the synthesis examples

Intermediate Synthesis Example 1: Synthesis of Intermediate A

Under an argon atmosphere, a mixture of 7.40 g (22.1 mmol) of 2-bromo-9-phenyl-9-methyl-9H-fluorene, 5.08 g (23.2 mmol) of 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline, 0.404 g (0.441 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.845 g (1.77 mmol) of 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (XPhos), 33 ml of 2M aqueous potassium phosphate solution, and 110 mL of 1,4-dioxane was stirred at 80°C for 7 hours. The reaction solution was cooled to room temperature and then concentrated under reduced pressure. The resulting solid was purified by silica gel column chromatography to obtain 7.67 g of a white solid (intermediate A-1). The yield was 99%.

Under an argon atmosphere, a mixture of 7.67 g (22.1 mmol) of intermediate A-1, 5.15 g (22.1 mmol) of 2-bromobiphenyl, 0.406 g (0.443 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.552 g (0.886 mmol) of BINAP, 2.343 g (24.4 mmol) of sodium t-butoxide, and 111 mL of toluene was stirred at 100°C for 30 hours. The reaction solution was cooled to room temperature and then concentrated under reduced pressure. The resulting solid was purified by silica gel column chromatography to obtain 6.93 g of a white solid. The yield was 63%.

Intermediate Synthesis Example 2: Synthesis of Intermediate B

Under an argon atmosphere, a mixture of 9.05 g (27.0 mmol) of 2-bromo9-phenyl-9-methyl-9H-fluorene, 5.07 g (32.4 mmol) of 2-chlorophenylboronic acid, 0.395 g (0.540 mmol) of [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct, 40.5 mL of 2M aqueous sodium carbonate solution, and 135 mL of DME was refluxed at the boiling point for 7 hours. The reaction solution was cooled to room temperature and then concentrated under reduced pressure. The resulting solid was purified by silica gel column chromatography to obtain 9.82 g of a white solid. The yield was 99%.

Intermediate Synthesis Example 3: Synthesis of Intermediate C

In the synthesis of intermediate A, the same procedure was followed except that bromobenzene was used instead of 2-bromobiphenyl, and a white solid was obtained in a yield of 75%.

Synthesis Example 1: Synthesis of Compound Inv-1

Under an argon atmosphere, a mixture of 5.93 g (11.9 mmol) of intermediate A, 3.89 g (14.2 mmol) of 2-bromo-9,9-dimethyl-9H-fluorene, 0.217 g (0.237 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.275 g (0.949 mmol) of tri-tert-butylphosphonium tetrafluoroborate, 23.7 mL of lithium bis(trimethylsilyl)amide (1M toluene solution), and 119 mL of xylene was refluxed at the boiling point for 7 hours. The reaction solution was cooled to room temperature and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography and recrystallization to obtain 3.29 g of a white solid. The yield was 40%.
Mass spectrometry showed that the product was compound Inv-1, with an m/e of 692 for a molecular weight of 691.92.

Synthesis Example 2: Synthesis of Compound Inv-2

Under an argon atmosphere, a mixture of 3.47 g (10.0 mmol) of intermediate A-1, 6.28 g (23.0 mmol) of 2-bromo-9,9-dimethyl-9H-fluorene, 0.366 g (0.400 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.464 g (1.60 mmol) of tri-tert-butylphosphonium tetrafluoroborate, 2.69 g (28.0 mmol) of sodium-t-butoxide, and 100 mL of xylene was stirred at 110° C. for 7 hours. The reaction solution was cooled to room temperature and then concentrated under reduced pressure. The obtained solid was purified by silica gel column chromatography to obtain 1.88 g of a white solid. The yield was 26%.
Mass spectrometry showed that the product was compound Inv-2, with an m/e of 732 for a molecular weight of 731.98.

Synthesis Example 3: Synthesis of Compound Inv-3

The same procedure as in Synthesis Example 2 was carried out except that 4-bromobiphenyl was used instead of 2-bromo-9,9-dimethyl-9H-fluorene, to obtain 3.51 g of a white solid in a yield of 54%.
Mass spectrometry showed that the product was compound Inv-3, with an m/e of 652 for a molecular weight of 651.85.

Synthesis Example 4: Synthesis of Compound Inv-4

Under an argon atmosphere, a mixture of 2.43 g (8.51 mmol) of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, 3.44 g (9.37 mmol) of intermediate B, 0.156 g (0.170 mmol) of tris(dibenzylideneacetone)dipalladium(0), 0.280 g (0.681 mmol) of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (SPhos), 1.15 g (11.9 mmol) of sodium-t-butoxide, and 85 mL of xylene was stirred at 110°C for 7 hours. The reaction solution was cooled to room temperature and then concentrated under reduced pressure. The obtained solid was purified by silica gel column chromatography to obtain 1.88 g of a white solid. The yield was 35%.
Mass spectrometry showed that the product was compound Inv-4, with an m/e of 616 for a molecular weight of 615.82.

Synthesis Example 5: Synthesis of Compound Inv-5

The same procedure as in Synthesis Example 4 was carried out except that Intermediate D was used instead of Intermediate B and Intermediate C was used instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, to obtain a white solid. The yield was 62%.
Mass spectrometry showed that the product was compound Inv-5, with an m/e of 692 for a molecular weight of 691.92.

Synthesis Example 6: Synthesis of Compound Inv-6

The same procedure was carried out as in Synthesis Example 4, except that N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-9H-fluoren-2-amine was used instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, to obtain a white solid. The yield was 48%.
Mass spectrometry showed that the product was compound Inv-6, with an m/e of 692 for a molecular weight of 691.92.

Synthesis Example 7: Synthesis of Compound Inv-7

The same procedure as in Synthesis Example 4 was carried out except that Intermediate E was used instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, to obtain a white solid. The yield was 47%.
Mass spectrometry showed that the product was compound Inv-7, with an m/e of 754 for a molecular weight of 753.99.

Synthesis Example 8: Synthesis of Compound Inv-8

The same procedure as in Synthesis Example 4 was carried out except that Intermediate F was used instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, to obtain a white solid. The yield was 55%.
Mass spectrometry showed that the product was compound Inv-8, with an m/e of 768 for a molecular weight of 767.97.

Synthesis Example 9: Synthesis of Compound Inv-9

The same procedure was carried out as in Synthesis Example 4, except that bis([1,1'-biphenyl]-4-yl-d9)amine was used instead of 9,9-dimethyl-N-phenyl-9H-fluoren-2-amine, to obtain a white solid. The yield was 65%.
Mass spectrometry showed that the product was compound Inv-9, with an m/e of 670 for a molecular weight of 669.96.

Reference Signs List 1, 11, 12 Organic EL element 2 Substrate 3 Anode 4 Cathode 5 Light-emitting layer 5a First light-emitting layer 5b Second light-emitting layer 6 Hole-transporting region (hole-transporting layer)
6a Hole injection layer 6b First hole transport layer 6c Second hole transport layer 6d Third hole transport layer 7 Electron transport zone (electron transport layer)
7a: First electron transport layer; 7b: Second electron transport layer; 10, 20, 30: Light-emitting unit

Claims (23)

A compound represented by the following formula (1):

(In formula (1),
N ^* is the central nitrogen atom.
One of R ^a and R ^b is a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, and the other is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
However, R ^a and R ^b may be bonded to each other to form a substituted or unsubstituted ring.
One selected from R ² , R ³ , R ⁶ and R ⁷ is a single bond bonding to *1, and R ¹ , R ⁴ , R ⁵ , R ⁸ , and R ² , R ³ , R ⁶ and R ⁷ that are not a single bond bonding to *1 are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 15 ring carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
Any two adjacent groups selected from R ¹ , R ⁴ , R ⁵ , R ⁸ , and R ² , R ³ , R ⁶ and R ⁷ that are not a single bond are not bonded to each other and therefore do not form a ring.
R ¹¹ to R ¹⁴ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 18 ring carbon atoms.
Adjacent two selected from R ¹¹ to R ¹⁴ are not bonded to each other and therefore do not form a ring.
L ¹ to L ⁴ each independently represent a single bond or a substituted or unsubstituted arylene group having 6 to 30 ring carbon atoms.
Ar ¹ and Ar ² are groups represented by any one of the following formulae (1a), (1f) and (1g) , and at least one of Ar ¹ and Ar ² is a group represented by the formula (1a) or (1g).

(In formula (1a),
*21 is the bonding position to ^L1 or ^L2 .
One selected from R ¹⁰¹ to R ¹⁰⁵ is a single bond bonding to *22, one selected from R ¹⁰⁶ to R ¹¹⁰ is a single bond bonding to *23, and one selected from R ¹¹¹ to R ¹¹⁵ is a single bond bonding to *24.
The R ¹⁰¹ to R ¹¹⁵ that are not single bonds are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted aryl group having 6 to 12 ring carbon atoms.
adjacent two of R ¹⁰¹ to R ¹⁰⁵ which are not single bonds are not bonded to each other and therefore do not form a ring;
any two adjacent R ¹⁰⁶ to R ¹¹⁰ which are not single bonds are not bonded to each other and therefore do not form a ring;
Any two adjacent groups selected from R ¹¹¹ to R ¹¹⁵ which are not single bonds are not bonded to each other and therefore do not form a ring.
m is 0 or 1, n is 0 or 1, l is 0 or 1, and m+n+l is 0 or 1 .
R ¹¹⁶ to R ¹²⁰ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
Any two adjacent groups selected from R ¹¹⁶ to R ¹²⁰ are not bonded to each other and therefore do not form a ring.

(In formula (1f),
*34 is the bonding position to ^L1 or ^L2 .
X is an oxygen atom, a sulfur atom, or NR ^A.
One selected from R ¹⁹¹ to R ¹⁹⁸ and R ^A is a single bond bonded to *35.
The R ^{3 A} that is not a single bond is a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms.
The R ¹⁹¹ to R ¹⁹⁸ that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
Any two adjacent groups selected from R ¹⁹¹ to R ¹⁹⁸ that are not single bonds may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore not form a ring.

(In formula (1g),
*36 is the bonding position to ^L1 or ^L2 .
One selected from R ^B , R ^C , and R ²⁰¹ to R ²⁰⁸ is a single bond bonded to *37.
The R ^B and R ^C that are not single bonds are each independently a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
The R 3 ^B and R 3 ^C which are not single bonds do not bond to each other to form a substituted or unsubstituted ring.
The R ²⁰¹ to R ²⁰⁸ that are not single bonds are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted or unsubstituted aryl group having 6 to 12 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
Any two adjacent non-single bonds selected from R ²⁰¹ to R ²⁰⁸ are not bonded to each other and therefore do not form a ring. 2. The compound according to claim 1, wherein one of R ^a and R ^b is a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, and the other is a substituted or unsubstituted phenyl group. 3. The compound according to claim 1 or 2, wherein ^R2 or ^R7 is a single bond bonded to *1. The compound according to claim 1 or 2, wherein ^L3 is a single bond. The compound according to claim 1 or 2, wherein ^L4 is a single bond. The compound according to claim 1 or 2, wherein Ar ¹ or Ar ² is a group represented by formula (1a), and the group represented by formula (1a) satisfies at least one of the following (i) to (iii):
(i) R ¹⁰¹ or R ¹⁰⁵ is a single bond bonded to *22; (ii) R ¹⁰⁶ or R ¹¹⁰ is a single bond bonded to *23; (iii) R ¹¹¹ or R ¹¹⁵ is a single bond bonded to *24. The compound according to claim 1 or 2, wherein Ar ¹ or Ar ² is a group represented by formula (1g), and in the group represented by formula (1g), ^R and ^R each independently represent a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group. The compound according to claim 1 or 2, wherein Ar ¹ or Ar ² is a group represented by formula (1g), and in the group represented by formula (1g), R ²⁰² or R ²⁰⁷ is a single bond that bonds to *37. 3. The compound according to claim 1, wherein L ¹ and L ² each independently represent a single bond or an arylene group having 6 to 12 ring carbon atoms. The compound according to claim 1 or 2, wherein L ¹ and L ² are single bonds. The compound according to claim 1 or 2, wherein R ¹¹ to R ¹⁴ are all hydrogen atoms. The compound according to claim 1 or 2, which contains at least one deuterium atom. A material for an organic electroluminescence device comprising the compound according to claim 1 or 2. A hole transport layer material comprising the compound according to claim 1 or 2. An organic electroluminescence element having a cathode, an anode, and an organic layer between the cathode and the anode, the organic layer including a light-emitting layer, and at least one layer of the organic layer including the compound according to claim 1 or 2. The organic electroluminescence device according to claim 15, wherein the organic layer includes a hole transport zone between the anode and the light emitting layer, and the hole transport zone includes the compound. The organic electroluminescence element according to claim 16, wherein the hole transport zone includes a first hole transport layer on the anode side and a second hole transport layer on the cathode side, and one or both of the first hole transport layer and the second hole transport layer include the compound. The organic electroluminescence element according to claim 17, wherein the light-emitting layer and the second hole transport layer are in direct contact with each other. The organic electroluminescence element according to claim 17, wherein the sum of the thickness of the first hole transport layer and the thickness of the second hole transport layer is 30 nm or more and 150 nm or less. The organic electroluminescence element according to claim 15, wherein the light-emitting layer is a single layer. The organic electroluminescence element according to claim 15, wherein the light-emitting layer contains a light-emitting compound that exhibits fluorescent emission with a main peak wavelength of 500 nm or less. The organic electroluminescence device according to claim 15, wherein the light-emitting layer contains a fluorescent dopant material. An electronic device including the organic electroluminescence element according to claim 15.