JP2024040050A - Organic electroluminescent devices and electronic equipment - Google Patents

Abstract

[Problem] To provide an organic electroluminescence element with improved element performance, and an electronic device including such an organic electroluminescence element. [Solution] An organic electroluminescence element having an anode, a cathode, and an organic layer present between the anode and the cathode, the organic layer including a light-emitting layer and a hole-transporting zone present between the anode and the light-emitting layer, the hole-transporting zone including a compound A-containing hole-transporting layer containing a specific compound A having fluorene, and a compound B-containing hole-transporting layer present on the light-emitting layer side of the compound A-containing hole-transporting layer and containing a specific compound B which is a triarylamine different from compound A; and an electronic device including the organic electroluminescence element. [Selected Figure] None

Description

The present invention relates to an organic electroluminescent device and an electronic device including the organic electroluminescent device.

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

Patent Documents 1 to 3 disclose compounds used as materials for organic electroluminescent devices.

International Publication No. 2013/118846 International Publication No. 2015/162912 International Publication No. 2022/009999

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

The present invention was made to solve the above-mentioned problems, and provides an organic EL device whose device performance is further improved by including a combination of specific compounds, and an electronic device including such an organic EL device. The purpose is to

As a result of extensive research into the performance of organic EL devices containing the compounds described in Patent Documents 1 to 3, the present inventors found that the organic layer contains compound A containing compound A represented by formula (1). An organic EL including a hole transport zone including a hole transport layer and a hole transport layer containing a compound B represented by formula (2) and containing a compound B different from compound A represented by formula (1). It has been found that the device exhibits higher performance.

In one embodiment, the present invention provides an organic electroluminescent device having an anode, a cathode, and an organic layer present between the anode and the cathode, the organic layer including a light emitting layer, a light emitting layer between the anode and the light emitting layer. a hole transport zone existing between the layers, the hole transport zone includes a compound A-containing hole transport layer containing compound A represented by the following formula (1); A compound B-containing hole transport layer that is present on the light-emitting layer side of the transport layer, is represented by the following formula (2), and contains a compound B that is different from compound A represented by the following formula (1); An organic electroluminescent device is provided.
(In the above formula (1),
N ^* is the central nitrogen atom.
Ar ¹ and Ar ² are each independently a substituted or unsubstituted aryl group having 6 to 30 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
L ¹ to L ³ are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 18 ring atoms, or a substituted or unsubstituted divalent hetero group having 5 to 30 ring atoms; It is a ring group.
Ar ³ is each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 ring carbon atoms; ~30 aryl group, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. However, at least one of Ar ³ is a substituted or unsubstituted aryl group having 6 to 30 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
n is an integer from 1 to 4, and when n is 2 or more, the plurality of Ar ³ 's are the same or different.
R ⁹ and R ¹⁰ are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring-forming carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms; An aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
R ⁹ and R ¹⁰ may be bonded to each other to form a ring structure, or may not be bonded to each other to form a ring structure. However, when R ⁹ and R ¹⁰ do not combine with each other to form a ring, at least one of R ⁹ and R ¹⁰ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
One selected from R ¹ to R ⁴ is a single bond bonded to *1,
*R ¹ to R ⁴ that are not single bonds bonded to 1 are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. Substituted alkenyl group having 2 to 50 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 ring forming carbon atoms, substituted or unsubstituted ring forming carbon Aryl group with 6 to 50 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 50 carbon atoms, substituted or unsubstituted heterocyclic group with 5 to 50 ring atoms, substituted or unsubstituted heterocyclic group with 1 to 50 carbon atoms Haloalkyl group, substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms, group represented by -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ), group represented by -O-(R ₉₀₄ ) , or a group represented by -S-(R ₉₀₅ ),
R ₉₀₁ to R ₉₀₅ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms; an 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 _901s exist, the two or more R _901s are the same or different,
When two or more R _902s exist, the two or more R _902s are the same or different,
When two or more R _903s exist, the two or more R _903s are the same or different,
When two or more R _904s exist, the two or more R _904s are the same or different,
When two or more R _905s exist, the two or more R _905s are the same or different.
However, two adjacent ones selected from R ¹ to R ⁴ that are not single bonds bonded to *1 may bond to each other to form a substituted or unsubstituted benzene ring, and do not bond to each other, thus forming a ring. It does not need to be formed.
n selected from R ⁵ to R ⁸ are single bonds bonded to *2,
*R ⁵ to R ⁸ that are not single bonds bonded to *2 are each independently hydrogen atoms. )
(In the above formula (2),
N ^* is the central nitrogen atom.
L ^A1 , L ^A2 and L ^A3 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring atoms, or a substituted or unsubstituted arylene group having 5 to 50 ring atoms; is a valent heterocyclic group.
Ar ¹¹¹ , Ar ¹¹² and Ar ¹¹³ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or -Si(R ^C1 )(R ^C2 )(R ^C3 ).
R ^C1 , R ^C2 and R ^C3 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
When there are multiple R ^C1s , the multiple R ^C1s are the same or different,
When a plurality of R ^C2s exist, the plurality of R ^C2s are the same or different from each other,
When a plurality of R ^C3s exist, the plurality of R ^C3s are the same or different from each other. )

In another aspect, the present invention provides an electronic device including the organic electroluminescent device.

A compound A-containing hole transport layer containing compound A represented by formula (1), and compound B containing compound B represented by formula (2) and different from compound A represented by formula (1). An organic EL device having an organic layer including a hole transport zone containing a hole transport layer exhibits improved device performance.

1 is a schematic diagram showing an example of a layer structure of an organic EL element according to one embodiment of the present invention. FIG. 3 is a schematic diagram illustrating another example of the layer structure of an organic EL element according to one embodiment of the present invention. FIG. 3 is a schematic diagram showing still another example of the layer structure of an organic EL element according to one embodiment of the present invention.

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

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

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

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

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

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

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

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

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

・“Substituted or unsubstituted aryl group”
Specific examples (specific example group G1) of the "substituted or unsubstituted aryl group" described in this specification include the following unsubstituted aryl groups (specific example group G1A) and substituted aryl groups (specific example group G1B). ) etc. (Here, the unsubstituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is an "unsubstituted aryl group", and the substituted aryl group refers to the case where the "substituted or unsubstituted aryl group" is (Refers to the case where it is a "substituted aryl group.") In this specification, the mere mention of "aryl group" includes both "unsubstituted aryl group" and "substituted aryl group."
"Substituted aryl group" means a group in which one or more hydrogen atoms of "unsubstituted aryl group" are replaced with a substituent. Examples of the "substituted aryl group" include a group in which one or more hydrogen atoms of the "unsubstituted aryl group" in the specific example group G1A below are replaced with a substituent, and a substituted aryl group in the following specific example group G1B. Examples include: The examples of "unsubstituted aryl group" and "substituted aryl group" listed here are just examples, and the "substituted aryl group" described in this specification includes the following specific examples. A group in which the hydrogen atom bonded to the carbon atom of the aryl group itself in the "substituted aryl group" of Group G1B is further replaced with a substituent, and a hydrogen atom of the substituent in the "substituted aryl group" in the following specific example group G1B is Furthermore, groups substituted with substituents are also included.

・Unsubstituted aryl group (specific example group G1A):
phenyl group,
p-biphenyl group,
m-biphenyl group,
o-biphenyl group,
p-terphenyl-4-yl group,
p-terphenyl-3-yl group,
p-terphenyl-2-yl group,
m-terphenyl-4-yl group,
m-terphenyl-3-yl group,
m-terphenyl-2-yl group,
o-terphenyl-4-yl group,
o-terphenyl-3-yl group,
o-terphenyl-2-yl group,
1-naphthyl group,
2-naphthyl group,
anthryl group,
benzanthryl group,
phenanthryl group,
benzophenanthryl group,
phenalenyl group,
pyrenyl group,
chrysenyl group,
benzocrysenyl group,
triphenylenyl group,
benzotriphenylenyl group,
tetracenyl group,
pentacenyl group,
fluorenyl group,
9,9'-spirobifluorenyl group,
benzofluorenyl group,
dibenzofluorenyl group,
fluoranthenyl group,
benzofluoranthenyl group,
A monovalent aryl group derived by removing one hydrogen atom from a perylenyl group and a ring structure represented by the following general formulas (TEMP-1) to (TEMP-15).

・Substituted aryl group (specific example group G1B):
o-tolyl group,
m-tolyl group,
p-tolyl group,
para-xylyl group,
meta-xylyl group,
ortho-xylyl group,
para-isopropylphenyl group,
meta-isopropylphenyl group,
ortho-isopropylphenyl group,
para-t-butylphenyl group,
meta-t-butylphenyl group,
ortho-t-butylphenyl group,
3,4,5-trimethylphenyl group,
9,9-dimethylfluorenyl group,
9,9-diphenylfluorenyl group 9,9-bis(4-methylphenyl)fluorenyl group,
9,9-bis(4-isopropylphenyl)fluorenyl group,
9,9-bis(4-t-butylphenyl)fluorenyl group,
cyanophenyl group,
triphenylsilylphenyl group,
trimethylsilylphenyl group,
phenylnaphthyl group,
A group in which one or more hydrogen atoms of a monovalent group derived from a naphthylphenyl group and a ring structure represented by the above general formulas (TEMP-1) to (TEMP-15) are replaced with a substituent.

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

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

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

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

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

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

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

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

・Substituted heterocyclic group containing a nitrogen atom (specific example group G2B1):
(9-phenyl)carbazolyl group,
(9-biphenylyl)carbazolyl group,
(9-phenyl)phenylcarbazolyl group,
(9-naphthyl)carbazolyl group,
diphenylcarbazol-9-yl group,
phenylcarbazol-9-yl group,
methylbenzimidazolyl group,
ethylbenzimidazolyl group,
phenyltriazinyl group,
biphenylyltriazinyl group,
diphenyltriazinyl group,
phenylquinazolinyl group, and biphenylylquinazolinyl group.

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

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

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

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

・“Substituted or unsubstituted alkyl group”
Specific examples (specific example group G3) of the "substituted or unsubstituted alkyl group" described in this specification include the following unsubstituted alkyl groups (specific example group G3A) and substituted alkyl groups (specific example group G3B). ). (Here, an unsubstituted alkyl group refers to a case where a "substituted or unsubstituted alkyl group" is an "unsubstituted alkyl group," and a substituted alkyl group refers to a case where a "substituted or unsubstituted alkyl group" is (This refers to the case where it is a "substituted alkyl group.") Hereinafter, when it is simply referred to as an "alkyl group," it includes both an "unsubstituted alkyl group" and a "substituted alkyl group."
"Substituted alkyl group" means a group in which one or more hydrogen atoms in "unsubstituted alkyl group" are replaced with a substituent. Specific examples of the "substituted alkyl group" include groups in which one or more hydrogen atoms in the "unsubstituted alkyl group" (specific example group G3A) below are replaced with a substituent, and substituted alkyl groups (specific examples Examples include group G3B). In this specification, the alkyl group in "unsubstituted alkyl group" means a chain alkyl group. Therefore, the "unsubstituted alkyl group" includes a linear "unsubstituted alkyl group" and a branched "unsubstituted alkyl group". The examples of "unsubstituted alkyl group" and "substituted alkyl group" listed here are just examples, and the "substituted alkyl group" described in this specification includes specific example group G3B. A group in which the hydrogen atom of the alkyl group itself in the "substituted alkyl group" in "Substituted alkyl group" is further replaced with a substituent, and a group in which the hydrogen atom of the substituent in the "substituted alkyl group" in Example Group G3B is further replaced with a substituent. included.

・Unsubstituted alkyl group (specific example group G3A):
methyl group,
ethyl group,
n-propyl group,
isopropyl group,
n-butyl group,
isobutyl group,
s-butyl group and t-butyl group.

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

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

・Unsubstituted alkenyl group (specific example group G4A):
vinyl group,
allyl group,
1-butenyl group,
2-butenyl group and 3-butenyl group.

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

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

・Unsubstituted alkynyl group (specific example group G5A):
ethynyl group

・“Substituted or unsubstituted cycloalkyl group”
Specific examples (specific example group G6) of the "substituted or unsubstituted cycloalkyl group" described in this specification include the following unsubstituted cycloalkyl groups (specific example group G6A) and substituted cycloalkyl groups ( Examples include specific example group G6B). (Here, the term "unsubstituted cycloalkyl group" refers to the case where "substituted or unsubstituted cycloalkyl group" is "unsubstituted cycloalkyl group", and the term "substituted cycloalkyl group" refers to "substituted or unsubstituted cycloalkyl group"). ("cycloalkyl group" refers to the case where "substituted cycloalkyl group" is used.) In this specification, when simply referring to "cycloalkyl group", it refers to "unsubstituted cycloalkyl group" and "substituted cycloalkyl group". including both.
"Substituted cycloalkyl group" means a group in which one or more hydrogen atoms in "unsubstituted cycloalkyl group" are replaced with a substituent. Specific examples of the "substituted cycloalkyl group" include the following "unsubstituted cycloalkyl group" (specific example group G6A) in which one or more hydrogen atoms are replaced with a substituent, and a substituted cycloalkyl group. (Specific example group G6B) and the like can be mentioned. The examples of "unsubstituted cycloalkyl group" and "substituted cycloalkyl group" listed here are just examples, and the "substituted cycloalkyl group" described in this specification includes specific A group in which one or more hydrogen atoms bonded to the carbon atom of the cycloalkyl group itself is replaced with a substituent in the "substituted cycloalkyl group" of example group G6B, and in the "substituted cycloalkyl group" of specific example group G6B Also included are groups in which the hydrogen atom of a substituent is further replaced with a substituent.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

The substituted or unsubstituted heterocyclic group described herein is preferably a pyridyl group, a pyrimidinyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a quinazolinyl group, a benzimidazolyl group, or a phenol group, unless otherwise specified herein. Nanthrolinyl group, carbazolyl group (1-carbazolyl group, 2-carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, or 9-carbazolyl group), benzocarbazolyl group, azacarbazolyl group, diazacarbazolyl group , dibenzofuranyl group, naphthobenzofuranyl group, azadibenzofuranyl group, diazadibenzofuranyl group, dibenzothiophenyl group, naphthobenzothiophenyl group, azadibenzothiophenyl group, diazadibenzothiophenyl group, ( 9-phenyl)carbazolyl group ((9-phenyl)carbazol-1-yl group, (9-phenyl)carbazol-2-yl group, (9-phenyl)carbazol-3-yl group, or (9-phenyl)carbazole -4-yl group), (9-biphenylyl)carbazolyl group, (9-phenyl)phenylcarbazolyl group, diphenylcarbazol-9-yl group, phenylcarbazol-9-yl group, phenyltriazinyl group, biphenylyl group These include riazinyl group, diphenyltriazinyl group, phenyldibenzofuranyl group, and phenyldibenzothiophenyl group.

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

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

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

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

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

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

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

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

・“Substituted or unsubstituted alkylene group”
Unless otherwise specified, the "substituted or unsubstituted alkylene group" described in this specification refers to 2 derived from the above "substituted or unsubstituted alkyl group" by removing one hydrogen atom on the alkyl chain. It is the basis of valence. As a specific example of a "substituted or unsubstituted alkylene group" (specific example group G14), one hydrogen atom on the alkyl chain is removed from the "substituted or unsubstituted alkyl group" described in specific example group G3. Examples include divalent groups derived from the derivatives.

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

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

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

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

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

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

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

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

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

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

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

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

The "single ring" or "fused ring" that is formed may be a saturated ring or an unsaturated ring as the structure of only the formed ring. Even if "one set of two adjacent rings" forms a "monocycle" or "fused ring," the "monocycle" or "fused ring" is a saturated ring, or Can form unsaturated rings. For example, ring Q _A and ring Q _B formed in the general formula (TEMP-104) are each a "monocyclic ring" or a "fused ring." Furthermore, the ring Q _A and the ring Q _C formed in the general formula (TEMP-105) are "fused rings". Ring Q _A and ring Q _C in the general formula (TEMP-105) are a condensed ring due to the condensation of ring Q _A and ring Q _C. When ring Q _A in the general formula (TEMP-104) is a benzene ring, ring Q _A is a monocyclic ring. When ring Q _A in the general formula (TEMP-104) is a naphthalene ring, ring Q _A is a fused ring.

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

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

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

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

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

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

Unless otherwise specified in this specification, any adjacent substituents may form a "saturated ring" or "unsaturated ring", preferably a substituted or unsubstituted saturated ring. Forms a membered ring, a substituted or unsubstituted saturated 6-membered ring, a substituted or unsubstituted unsaturated 5-membered ring, or a substituted or unsubstituted unsaturated 6-membered ring, more preferably a benzene ring do.
Unless otherwise specified herein, any substituent may further have a substituent. The substituents that the arbitrary substituents further have are the same as the above arbitrary substituents.

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

[Organic EL element]
The organic EL device of the present invention will be explained below.
The organic EL device of the present invention has an anode, a cathode, and an organic layer existing between the anode and the cathode. The organic layer includes an emissive layer and a hole transport zone located between the anode and the emissive layer. The hole transport zone exists in the compound A-containing hole transport layer containing compound A represented by formula (1) and on the light-emitting layer side from the compound A-containing hole transport layer, and ) and a compound B-containing hole transport layer containing a compound B different from compound A represented by formula (1).
Hereinafter, the compound represented by formula (1) will be referred to as "compound A", and the compound represented by formula (2), which is different from compound A represented by formula (1), will be referred to as "compound B".
Note that "compound B represented by formula (2) and different from compound A represented by formula (1)" means "compound B is a compound represented by formula (2) that is different from compound A represented by formula (1)". "It is a compound excluding the expressed compound."

The hole transport layer containing compound A may be a single layer or a multilayer. For example, when compound A is contained in both the first hole transport layer and the second hole transport layer, the compound A is present closer to the anode than the second hole transport layer (the layer closest to the anode ) The first hole transport layer corresponds to a compound A-containing hole transport layer.
The hole transport layer containing compound B may be a single layer or a multilayer. For example, when compound B is contained in both the second hole transport layer and the third hole transport layer, the compound B is present closer to the light emitting layer than the second hole transport layer (the layer closest to the light emitting layer). ) The third hole transport layer corresponds to the compound B-containing hole transport layer.

For a hole transport layer containing both compound A and compound B, if the content of compound A in the same hole transport layer is greater than the content of compound B, it is considered a hole transport layer containing compound A, On the other hand, when the content of compound B in the same hole transport layer is greater than the content of compound A, the hole transport layer is treated as a compound B-containing hole transport layer.
The compound A-containing hole transport layer may contain compound B, or may not contain compound B, as long as it contains compound A.
The compound B-containing hole transport layer may contain compound A, or may not contain compound A, as long as it contains compound B.

<Compound A>
Compound A is represented by formula (1) and is included in the compound A-containing hole transport layer in the organic layer of the organic EL element.

Compound A will be explained below.
Compound A is represented by formula (1). Hereinafter, equation (1) and symbols included in equation (1) and included in each equation described below will be explained. Unless otherwise specified, identical symbols have the same meaning.
Formula (1) and a compound represented by the below-described formula included in formula (1) may be referred to as "compound A."

The first compound A is represented by the following formula (1).

In the above formula (1), N ^* is a central nitrogen atom.

(Ar ¹ and Ar ² )
In the above formula (1), Ar ¹ and Ar ² are each independently a substituted or unsubstituted aryl group having 6 to 30 ring atoms, or a substituted or unsubstituted aryl group having 5 to 30 ring atoms. A heterocyclic group, preferably a group represented by the following formula (2A), the following formula (2B), the following formula (2C), the following formula (2D), the following formula (2E), or the following formula (2F) It is.

Examples of the unsubstituted aryl group having 6 to 30 ring carbon atoms include:
Phenyl group, biphenyl group, terphenyl group, naphthyl group, anthryl group, benzanthryl group, phenanthryl group, benzophenanthryl group, pyrenyl group, chrysenyl group, benzochrysenyl group, fluorenyl group, fluoranthenyl group, perylenyl group, or is a triphenylenyl group;
Preferably, it is a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group;
More preferably, phenyl group, 2-, 3-, or 4-biphenylyl group, 2-, 3-, or 4-o-terphenylyl group, 2-, 3-, or 4-m-terphenylyl group, 2-, 3- or 4-p-terphenylyl group, or 1- or 2-naphthyl group;
More preferably, it is a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group;
Particularly preferred is a phenyl group.

The unsubstituted heterocyclic group having 5 to 30 ring carbon atoms is, for example,
Pyrrolyl group, furyl group, thienyl group, pyridyl group, imidazopyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, imidazolyl group, oxazolyl group, thiazolyl group, pyrazolyl group, isoxazolyl group, isothiazolyl group, oxadiazolyl group, thiadiazolyl group group, triazolyl group, tetrazolyl 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, benzisoxazolyl group, benzisothiazolyl group, phenanthridinyl group, acridinyl group, phenanthrolinyl group, phenazinyl group, phenothiazinyl group, phenoxazinyl group, xanthenyl group, benzofuranyl group, isobenzofuranyl group Nyl group, naphthobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group (benzothienyl group, same below), isobenzothiophenyl group (isobenzothienyl group, same below), naphthobenzothiophenyl group (naphthobenzothiophenyl group, same below) a thienyl group (the same applies hereinafter), a dibenzothiophenyl group (dibenzothienyl group, the same hereinafter), or a carbazolyl group;
Preferably, it is a benzofuranyl group, isobenzofuranyl group, naphthobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group, isobenzothiophenyl group, naphthobenzothiophenyl group, dibenzothiophenyl group, or carbazolyl group. ,
More preferred are a dibenzofuranyl group, a dibenzothiophenyl group, or a carbazolyl group (including a 9-carbazolyl group or a 1-, 2-, 3-, or 4-carbazolyl group; the same applies hereinafter).

((Formula (2A)))
In formula (2A), *21 is the bonding position to L ¹ or L ² .
One selected from R ¹⁰¹ to R ¹⁰⁵ is a single bond bonded to *22, and one selected from R ¹⁰⁶ to R ¹¹⁰ is a single bond bonded to *23.
R ¹⁰¹ to R ¹⁰⁵ and R ¹⁰⁶ to R ¹¹⁰ , which are not single bonds, are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted ring having 6 to 12 carbon atoms. is an aryl group.

Examples of the unsubstituted alkyl group having 1 to 10 carbon atoms include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, and pentyl group. group, hexyl group, heptyl group, octyl group, nonyl group, or decyl group;
Preferably, it is a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, or hexyl group;
More preferably a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, or t-butyl group;
More preferably a methyl group or a t-butyl group;
Particularly preferred is t-butyl group.

Examples of the unsubstituted aryl group having 6 to 12 ring carbon atoms include:
a phenyl group, a biphenyl group, or a naphthyl group;
Preferably, it is a phenyl group, a 2-, 3-, or 4-biphenylyl group, or a 1- or 2-naphthyl group;
More preferably a phenyl group or a 1- or 2-naphthyl group;
Particularly preferred is a phenyl group.

Two adjacent ones selected from R ¹⁰¹ to R ¹⁰⁵ that are not single bonds do not bond to each other and do not form a ring.
Two adjacent ones selected from R ¹⁰⁶ to R ¹¹⁰ that are not single bonds do not bond to each other and do not form a ring.

R ¹¹¹ to R ¹¹⁵ 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 aryl group having 6 to 12 ring carbon atoms; It is a substituted heterocyclic group having 5 to 13 ring atoms.
Two adjacent ones selected from R ¹¹¹ to R ¹¹⁵ do not bond to each other and do not form a ring.

The details and preferred examples of the unsubstituted alkyl group having 1 to 10 carbon atoms are the same as the explanation of the substituents for R ¹⁰¹ to R ¹⁰⁵ and R ¹⁰⁶ to R ¹¹⁰ above.
The details and preferred examples of the unsubstituted aryl group having 6 to 12 ring carbon atoms are the same as the description of the substituents for R ¹⁰¹ to R ¹⁰⁵ and R ¹⁰⁶ to R ¹¹⁰ above.

Examples of the unsubstituted heterocyclic group having 5 to 13 ring carbon atoms 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, and an imidazolyl group. , oxazolyl group, thiazolyl group, pyrazolyl group, isoxazolyl group, isothiazolyl group, oxadiazolyl group, thiadiazolyl group, triazolyl group, tetrazolyl group, indolyl group, isoindolyl group, indolizinyl group, quinolidinyl group, quinolyl group, isoquinolyl group, cinnolyl group, phthalazinyl group group, quinazolinyl group, quinoxalinyl group, benzimidazolyl group, benzoxazolyl group, benzothiazolyl group, indazolyl group, benzisoxazolyl group, benzisothiazolyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, a benzothiophenyl group (benzothienyl group, the same hereinafter), an isobenzothiophenyl group (isobenzothienyl group, the same hereinafter), a dibenzothiophenyl group (dibenzothienyl group, the same hereinafter), or a carbazolyl group;
Preferred are pyrrolyl group, furyl group, thienyl group, pyridyl group, pyrimidinyl group, triazinyl group, quinolyl group, isoquinolyl group, quinazolinyl group, benzimidazolyl group, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, and benzothiophenyl group. , an isobenzothiophenyl group, a dibenzothiophenyl group, or a carbazolyl group;
More preferably, benzofuranyl group, isobenzofuranyl group, dibenzofuranyl group, benzothiophenyl group, isobenzothiophenyl group, dibenzothiophenyl group, carbazolyl group (9-carbazolyl group, or 1-, 2-, 3- or 4-carbazolyl group).
Examples of the substituted heterocyclic group having 5 to 13 ring atoms include 9-phenylcarbazolyl group, 9-biphenylylcarbazolyl group, 9-phenylphenylcarbazolyl group, and 9-naphthylcarbazolyl group. group, phenyldibenzofuranyl group, or phenyldibenzothiophenyl group (phenyldibenzothienyl group, hereinafter the same).
The substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms includes isomer groups if present.

All of R ¹⁰¹ to R ¹⁰⁵ , R ¹⁰⁶ to R ¹¹⁰ and R ¹¹¹ to R ¹¹⁵ that are not single bonds in formula (2A) may be hydrogen atoms.

In formula (2A), m is 0, 1 or 2, and n is 0 or 1. Except when m is 2 and n is 0.
When m=0 and n=0, *23 represents *21.
When m=0 and n=1, *22 represents *21.
When m=1 and n=0, *23 represents *22.

In one aspect of the invention, m is 0 and n is 0. In this case, *23 represents *21, and formula (2A) is represented by the following formula.

In other embodiments of the invention, m is 0 and n is 1. In this case, *22 represents *21, and formula (2A) is represented by the following formula.

In other embodiments of the invention, m is 1 and n is 0. In this case, *23 represents *22, and formula (2A) is represented by the following formula.

In other embodiments of the invention, m is 1 and n is 1. In this case, formula (2A) is represented by the following formula.

In other embodiments of the invention, m is 2 and n is 1. In this case, formula (2A) is represented by the following formula.

The group represented by formula (2A) is preferably represented by the following formula. In the following formula, R is omitted for simplification.

((Formula (2B)))
In formula (2B), *24 is the bonding position to L ¹ or L ² .
One selected from R ¹²¹ to R ¹²⁸ is a single bond bonded to *25.
R ¹²¹ to R ¹²⁸ which 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 having 6 to 12 ring carbon atoms. It is the basis.
Two adjacent ones selected from R ¹²¹ to R ¹²⁸ that are not single bonds do not bond to each other and do not form a ring.

The details and preferred examples of the unsubstituted alkyl group having 1 to 10 carbon atoms are the same as the explanation of the substituents for R ¹⁰¹ to R ¹⁰⁵ and R ¹⁰⁶ to R ¹¹⁰ above.

The details and preferred examples of the unsubstituted aryl group having 6 to 12 ring carbon atoms are the same as the description of the substituents for R ¹⁰¹ to R ¹⁰⁵ and R ¹⁰⁶ to R ¹¹⁰ above.

In one aspect of the present invention, one selected from R ¹²¹ , R ¹²⁴ , R ¹²⁵ , and R ¹²⁸ is preferably a single bond bonded to *25.

All of R ¹²¹ to R ¹²⁸ that are not single bonds bonded to *25 may be hydrogen atoms.

((Formula (2C)))
In formula (2C), *26 is the bonding position to L ¹ or L ² .
One selected from R ¹³¹ to R ¹⁴⁰ is a single bond bonded to *27.
R ¹³¹ to R ¹⁴⁰ which 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 having 6 to 12 ring carbon atoms. It is the basis.
Two adjacent ones selected from R ¹³¹ to R ¹⁴⁰ that are not single bonds do not bond to each other and do not form a ring.

The details and preferred examples of the unsubstituted alkyl group having 1 to 10 carbon atoms are the same as the explanation of the substituents for R ¹⁰¹ to R ¹⁰⁵ and R ¹⁰⁶ to R ¹¹⁰ above.

The details and preferred examples of the unsubstituted aryl group having 6 to 12 ring carbon atoms are the same as the description of the substituents for R ¹⁰¹ to R ¹⁰⁵ and R ¹⁰⁶ to R ¹¹⁰ above.

In one aspect of the present invention, preferably one selected from R ¹³⁷ , R ¹³⁸ and R ¹³⁹ is a single bond bonded to *27, and more preferably one selected from R ¹³⁷ and R ¹³⁹ is a single bond bonded to *27. It is a single bond that binds, more preferably a single bond that R ¹³⁹ binds to *27.

*R ¹³¹ to R ¹⁴⁰ that are not single bonds bonded to *27 may all be hydrogen atoms.

((Formula (2D)))
In formula (2D), *28 is the bonding position to L ¹ or L ² .
X ¹¹ is an oxygen atom, a sulfur atom, CR ^a R ^b , or NR ^c , preferably an oxygen atom.

R ^a and R ^b are each independently 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 30 ring carbon atoms, and are bonded to each other. may be used to form a substituted or unsubstituted ring structure, or may not be bonded to each other and therefore do not form a ring.

The unsubstituted alkyl group having 1 to 30 carbon atoms is, for example,
Methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, is an undecyl group or a dodecyl group;
Preferably, it is a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group, or pentyl group;
More preferably a methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, or t-butyl group;
More preferably a methyl group, ethyl group, isopropyl group or t-butyl group;
Particularly preferred is a methyl group.

The details and preferred examples of the unsubstituted aryl group having 6 to 30 ring carbon atoms are the same as the explanation of the substituent for Ar ¹ and Ar ² above.

R ^c is 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 30 ring carbon atoms.

The details and preferred examples of the unsubstituted alkyl group having 1 to 30 carbon atoms are the same as the explanation of the substituents for R ^a and R ^b .
The details and preferred examples of the unsubstituted aryl group having 6 to 30 ring carbon atoms are the same as the explanation of the substituent for Ar ¹ and Ar ² above.

The substituted or unsubstituted ring structure that R ^a and R ^b may form by bonding with each other refers to a spiro ring including the carbon atom at position 9 of the fluorene skeleton to which R ^a and R ^b are bonded. may be formed. The spiro ring is a hydrocarbon ring or a heterocycle, and is selected from a monocyclic ring, a fused ring, a bridged bicyclo ring, and a bridged tricyclo ring.
Examples of the substituted or unsubstituted ring structure that R ^a and R ^b may form by combining with each other include, but are not limited to, the ring structures shown below. . Note that * in the ring structure shown below indicates the bonding position of the fluorene skeleton to the benzene ring.

n is 0 or 1.
^When n is 0, one selected ^from R ^a , R ^b , R ^c , and R ¹⁴¹ to R ¹⁴⁸ is a single bond bonded to *29, or a substitution or An unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted ring structure that can be formed by bonding R ^a or R ^b to each other, or a substituted or unsubstituted ring-forming carbon that can be represented by R ^c Six to thirty aryl groups may be bonded to *29 via a single bond.
When n is 1, one of R ¹⁴¹ and R ¹⁴² , R ¹⁴² and R ¹⁴³ , or R ¹⁴³ and R ¹⁴⁴ is a single bond bonded to *a, and the other is a single bond bonded to *b, and *a and *One selected from R ¹⁴¹ to R ¹⁴⁴ , R ¹⁴⁵ to R ¹⁴⁸ , R ^a , R ^b , R ^c , and R ²⁰⁰ to R ²⁰³ that is not a single bond bonded to *b is a single bond bonded to *29. or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms that R ^a or R ^b may represent; a substituted or unsubstituted ring structure that R ^a or R ^b may form by bonding with each other; Alternatively, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms that R ^c may represent may be bonded to *29 via a single bond.

The above non-single bonds R ¹⁴¹ to R ¹⁴⁸ and the above non-single bonds R ²⁰⁰ to R ²⁰³ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. An aryl group having 6 to 12 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
Two adjacent ones selected from R ¹⁴¹ to R ¹⁴⁸ , which are not single bonds, and R ²⁰⁰ to R ²⁰³ , which are not single bonds, do not bond to each other and do not form a ring.

The details and preferred examples of the unsubstituted alkyl group having 1 to 10 carbon atoms are the same as the explanation of the substituents for R ¹⁰¹ to R ¹⁰⁵ and R ¹⁰⁶ to R ¹¹⁰ above.

The details and preferred examples of the unsubstituted aryl group having 6 to 12 ring carbon atoms are the same as the description of the substituents for R ¹⁰¹ to R ¹⁰⁵ and R ¹⁰⁶ to R ¹¹⁰ above.

The details and preferred examples of the substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms are the same as the explanation of the substituents for R ¹¹¹ to R ¹¹⁵ above.

All of R ¹⁴¹ to R ¹⁴⁸ that are not single bonds and R ²⁰⁰ to R ²⁰³ that are not single bonds may all be hydrogen atoms.

((Formula (2E)))

In formula (2E), *30 is the bonding position to L ¹ or L ² .
One selected from R ¹⁵¹ to R ¹⁵⁵ is a single bond bonded to *31, and the other selected from R ¹⁵¹ to R ¹⁵⁵ is a single bond bonded to *32.
Each of R ¹⁵¹ to R ¹⁵⁵ that is not a single bond is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group.
Two adjacent ones selected from R ¹⁵¹ to R ¹⁵⁵ that are not single bonds do not bond to each other and do not form a ring.
R ¹⁶¹ to R ¹⁶⁵ and R ¹⁷¹ to R ¹⁷⁵ each independently represent a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms.
At least two adjacent atoms selected from R ¹⁶¹ to R ¹⁶⁵ that are not hydrogen atoms may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form a ring. You don't have to.
At least two adjacent atoms selected from R ¹⁷¹ to R ¹⁷⁵ that are not hydrogen atoms may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore form a ring. does not have to be formed.

Details and preferred examples of the unsubstituted alkyl group having 1 to 10 carbon atoms represented by R ¹⁵¹ to R ¹⁵⁵ , R ¹⁶¹ to R ¹⁶⁵ and R ¹⁷¹ to R ¹⁷⁵ are as follows: R ¹⁰¹ to R ¹⁰⁵ and R ¹⁰⁶ to R The explanation of the same substituent for ¹¹⁰ is the same.

In one embodiment of the present invention, two adjacent groups selected from R ¹⁶¹ to R ¹⁶⁵ are bonded to each other to form an unsubstituted benzene ring. In another aspect of the invention, two adjacent ones selected from R ¹⁶¹ to R ¹⁶⁵ do not bond to each other and therefore do not form a ring.
In one embodiment of the present invention, two adjacent groups selected from R ¹⁷¹ to R ¹⁷⁵ are bonded to each other to form an unsubstituted benzene ring. In another aspect of the invention, two adjacent ones selected from R ¹⁷¹ to R ¹⁷⁵ do not bond to each other and therefore do not form a ring.

R ¹⁵¹ to R ¹⁵⁵ that are not single bonds may all be hydrogen atoms, R ¹⁶¹ to R ¹⁶⁵ may all be hydrogen atoms, and R ¹⁷¹ to R ¹⁷⁵ may all be hydrogen atoms. .

((Formula (2F)))
In formula (2F), *32 is the bonding position to L ¹ or L ² .
One selected from R ¹⁸¹ to R ¹⁹² is a single bond bonded to *33.
R ¹⁸¹ to R ¹⁹² which 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 having 6 to 12 ring carbon atoms. It is the basis.
Two adjacent ones selected from R ¹⁸¹ to R ¹⁹² that are not single bonds do not bond to each other and do not form a ring.

The details and preferred examples of the unsubstituted alkyl group having 1 to 10 carbon atoms are the same as the explanation of the substituents for R ¹⁰¹ to R ¹⁰⁵ and R ¹⁰⁶ to R ¹¹⁰ above.

The details and preferred examples of the unsubstituted aryl group having 6 to 12 ring carbon atoms are the same as the description of the substituents for R ¹⁰¹ to R ¹⁰⁵ and R ¹⁰⁶ to R ¹¹⁰ above.

In one aspect of the invention, R ¹⁸⁴ is a single bond attached to *33, and in another aspect R ¹⁸³ is a single bond attached to *33.

All of R ¹⁸¹ to R ¹⁹² that are not single bonds may be hydrogen atoms.

(L ¹ ~L ³ )
In the above formula (1), L ¹ to L ³ are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 18 ring carbon atoms, or a substituted or unsubstituted arylene group having 5 ring atoms. -30 divalent heterocyclic group, preferably a single bond or a substituted or unsubstituted phenylene group.

Examples of the unsubstituted arylene group having 6 to 18 ring carbon atoms represented by L ¹ to L ³ include a phenylene group (1,2-phenylene group, 1,3-phenylene group, 1,4-phenylene group), Naphthylene group (1,4-naphthylene group, 1,5-naphthylene group, etc.), biphenylylene group, fluorenylene group (2,7-fluorenylene group, etc.), 9,9-disubstituted fluorenylene group (9,9-dimethyl-2 , 7-fluorenylene group, 9,9-diphenyl-2,7-fluorenylene group, etc.), benzofluorenylene group, tetrathenylene group, pyrenylene group, chrysenylene group, s-indacenylene group, as-indacenylene group, and triphenylene group etc. The number of ring carbon atoms in the arylene group is preferably 6 to 14, more preferably 6 to 12, still more preferably 6 to 10, even more preferably 6.

Examples of the unsubstituted divalent heterocyclic group having 5 to 30 ring atoms represented by L ¹ to L ³ include the unsubstituted heterocyclic group having 5 to 30 ring atoms represented by Ar ¹ and Ar ² ; A divalent group derived by removing one hydrogen atom on the ring is preferred.

(Ar ³ )
In the above formula (1), Ar ³ is each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably 10 to 30 carbon atoms, or a substituted or unsubstituted alkyl group having 3 to 30 ring forming carbon atoms, preferably is a cycloalkyl group having 10 to 30 carbon atoms, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, preferably 10 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 5 to 30 ring carbon atoms, preferably 10 to 30 carbon atoms; 30 heterocyclic groups. However, in this case, at least one of Ar ³ is a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, preferably 10 to 30 carbon atoms, or a substituted or unsubstituted aryl group having 5 to 30 ring-forming atoms, Preferably it is a 10 to 30 heterocyclic group.

The details and preferred examples of the unsubstituted alkyl group having 1 to 30 carbon atoms are the same as the explanation of the substituents for R ^a and R ^b .

The unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms is, for example, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-norbornyl group, a 2-norbornyl group, a 1-adamantyl group, or a 2-norbornyl group. - adamantyl group;
Preferably, it is a cyclohexyl group, a 1-norbornyl group, a 2-norbornyl group, a 1-adamantyl group, or a 2-adamantyl group;
More preferred is a cyclohexyl group, 1-adamantyl group, or 2-adamantyl group.

The details and preferred examples of the unsubstituted aryl group having 6 to 30 ring carbon atoms are the same as the explanation of the substituent for Ar ¹ and Ar ² above.

The details and preferred examples of the unsubstituted heterocyclic group having 5 to 30 ring atoms are the same as the explanation of the substituent for Ar ¹ and Ar ² above.

(n)
In the above formula (1), n is an integer of 1 to 4, preferably an integer of 1 or 2. When n is 2 or more, the plurality of Ar ³ 's are the same or different.

(R ⁹ and R ¹⁰ )
In the above formula (1), R ⁹ and R ¹⁰ are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, A substituted or unsubstituted aryl group having 6 to 30 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
R ⁹ and R ¹⁰ may be bonded to each other to form a ring structure, or may not be bonded to each other to form a ring structure. However, when R ⁹ and R ¹⁰ do not combine with each other to form a ring, at least one of R ⁹ and R ¹⁰ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.

The details and preferred examples of the unsubstituted alkyl group having 1 to 30 carbon atoms are the same as the explanation of the substituents for R ^a and R ^b .

Details and preferred examples of the unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms are the same as the explanation of the substituent for Ar ³ above.

The details and preferred examples of the unsubstituted aryl group having 6 to 30 ring carbon atoms are the same as the explanation of the substituent for Ar ¹ and Ar ² above.

The details and preferred examples of the unsubstituted heterocyclic group having 5 to 30 ring atoms are the same as the explanation of the substituent for Ar ¹ and Ar ² above.

(R ¹ to R ⁴ )
In the above formula (1), one selected from R ¹ to R ⁴ is a single bond bonded to *1.
In the above formula (1), R ¹ to R ⁴ that are not single bonds bonded to *1 are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, a substituted or unsubstituted carbon number of 1 to 50 Alkyl group, substituted or unsubstituted alkenyl group having 2 to 50 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, substituted or unsubstituted aryl group having 6 to 50 ring atoms, substituted or unsubstituted aralkyl group having 7 to 50 ring atoms, substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, substituted or unsubstituted A haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms, a group represented by -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ), -O-(R ₉₀₄ ) or a group represented by -S-(R ₉₀₅ ).

Examples of the unsubstituted alkyl group having 1 to 50 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a s-butyl group, a t-butyl group, a pentyl group (including isomeric groups), a hexyl group (including isomeric groups), a heptyl group (including isomeric groups), an octyl group (including isomeric groups), a nonyl group (including isomeric groups), a decyl group (including isomeric groups), an undecyl group (including isomeric groups), and a dodecyl group (including isomeric groups).
Among these, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group, t-butyl group and pentyl group (including isomeric groups) are preferred, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, s-butyl group and t-butyl group are more preferred, and methyl group, ethyl group, isopropyl group and t-butyl group are particularly preferred.

Examples of the unsubstituted alkenyl group having 2 to 50 carbon atoms include vinyl group, allyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1,3-butandienyl group, and 1-methylvinyl group. , styryl group, 2,2-diphenylvinyl group, 1,2-diphenylvinyl group, 1-methylallyl group, 1,1-dimethylallyl group, 2-methylallyl group, 1-phenylallyl group, 2-phenylallyl group, Examples include 3-phenylallyl group, 3,3-diphenylallyl group, 1,2-dimethylallyl group, 1-phenyl-1-butenyl group, and 3-phenyl-1-butenyl group.
Among these, styryl group, 2,2-diphenylvinyl group, and 1,2-diphenylvinyl group are preferred.

Examples of the unsubstituted alkynyl group having 2 to 50 carbon atoms include propargyl group, 3-pentynyl group, and phenylethynyl group.

Examples of the unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclooctyl group, 1-norbornyl group, 2-norbornyl group, and 1-adamantyl group. group, 2-adamantyl group, etc.
Among these, cyclohexyl group, cyclooctyl group, 1-norbornyl group, 2-norbornyl group, 1-adamantyl group, and 2-adamantyl group are preferred.

Examples of the unsubstituted aryl group having 6 to 50 ring carbon atoms include phenyl group, naphthyl group, biphenylyl group, anthryl group, phenanthryl group, and terphenylyl group.
Among these, phenyl group, naphthyl group, and biphenylyl group are preferred.

Examples of the aralkyl group having 7 to 50 carbon atoms include benzyl group, α,α-phenylmethylbenzyl group, α,α-dimethylbenzyl group, α-phenoxybenzyl group, α,α-methylphenylbenzyl group, α , α-ditrifluoromethylbenzyl group, triphenylmethyl group, α-benzyloxybenzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2-phenylisopropyl group, phenyl-t-butyl group, α-naphthylmethyl group, 1-α-naphthylethyl group, 2-α-naphthylethyl group, 1-α-naphthylisopropyl group, 2-α-naphthylisopropyl group, β-naphthylmethyl group, 1-β- Naphthylethyl group, 2-β-naphthylethyl group, 1-β-naphthylisopropyl group, 2-β-naphthylisopropyl group, 1-pyrrolylmethyl group, 2-(1-pyrrolyl)ethyl group, p-methylbenzyl group, m -Methylbenzyl group, o-methylbenzyl group, p-chlorobenzyl group, m-chlorobenzyl group, o-chlorobenzyl group, p-bromobenzyl group, m-bromobenzyl group, o-bromobenzyl group, p-iodo Benzyl group, m-iodobenzyl group, o-iodobenzyl group, p-hydroxybenzyl group, m-hydroxybenzyl group, o-hydroxybenzyl group, p-aminobenzyl group, m-aminobenzyl group, o-aminobenzyl group , p-nitrobenzyl group, m-nitrobenzyl group, o-nitrobenzyl group, p-cyanobenzyl group, m-cyanobenzyl group, o-cyanobenzyl group, 1-hydroxy-2-phenylisopropyl group, 1-chloro Examples include -2-phenylisopropyl group.

Examples of the unsubstituted heterocyclic group having 5 to 50 ring atoms include 1-pyrrolyl group, 2-pyrrolyl group, 3-pyrrolyl group, pyrazinyl group, 2-pyridinyl group, 3-pyridinyl group, 4-pyrrolyl group, Pyridinyl group, 1-indolyl group, 2-indolyl group, 3-indolyl group, 4-indolyl group, 5-indolyl group, 6-indolyl group, 7-indolyl group, 1-isoindolyl group, 2-isoindolyl group, 3- Isoindolyl group, 4-isoindolyl group, 5-isoindolyl group, 6-isoindolyl group, 7-isoindolyl group, 2-furyl group, 3-furyl group, 2-benzofuranyl group, 3-benzofuranyl group, 4-benzofuranyl group, 5- Benzofuranyl group, 6-benzofuranyl group, 7-benzofuranyl group, 1-isobenzofuranyl group, 3-isobenzofuranyl group, 4-isobenzofuranyl group, 5-isobenzofuranyl group, 6-isobenzofuranyl group Nyl group, 7-isobenzofuranyl group, quinolyl group, 3-quinolyl group, 4-quinolyl group, 5-quinolyl group, 6-quinolyl group, 7-quinolyl group, 8-quinolyl group, 1-isoquinolyl group, 3 -isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 6-isoquinolyl group, 7-isoquinolyl group, 8-isoquinolyl group, 2-quinoxalinyl group, 5-quinoxalinyl group, 6-quinoxalinyl group, 1-carbazolyl group, 2 -Carbazolyl group, 3-carbazolyl group, 4-carbazolyl group, 9-carbazolyl group, 1-phenanthridinyl group, 2-phenanthridinyl group, 3-phenanthridinyl group, 4-phenanthridinyl group , 6-phenanthridinyl group, 7-phenanthridinyl group, 8-phenanthridinyl group, 9-phenanthridinyl group, 10-phenanthridinyl group, 1-acridinyl group, 2-acridinyl group , 3-acridinyl group, 4-acridinyl group, 9-acridinyl group, 1,7-phenanthrolin-2-yl group, 1,7-phenanthrolin-3-yl group, 1,7-phenanthrolin- 4-yl group, 1,7-phenanthrolin-5-yl group, 1,7-phenanthrolin-6-yl group, 1,7-phenanthrolin-8-yl group, 1,7-phenanth lolin-9-yl group, 1,7-phenanthrolin-10-yl group, 1,8-phenanthrolin-2-yl group, 1,8-phenanthrolin-3-yl group, 1,8- phenanthrolin-4-yl group, 1,8-phenanthrolin-5-yl group, 1,8-phenanthrolin-6-yl group, 1,8-phenanthrolin-7-yl group, 1, 8-phenanthrolin-9-yl group, 1,8-phenanthrolin-10-yl group, 1,9-phenanthrolin-2-yl group, 1,9-phenanthrolin-3-yl group, 1,9-phenanthrolin-4-yl group, 1,9-phenanthrolin-5-yl group, 1,9-phenanthrolin-6-yl group, 1,9-phenanthrolin-7-yl group group, 1,9-phenanthrolin-8-yl group, 1,9-phenanthrolin-10-yl group, 1,10-phenanthrolin-2-yl group, 1,10-phenanthrolin-3 -yl group, 1,10-phenanthrolin-4-yl group, 1,10-phenanthrolin-5-yl group, 2,9-phenanthrolin-1-yl group, 2,9-phenanthrolin -3-yl group, 2,9-phenanthrolin-4-yl group, 2,9-phenanthrolin-5-yl group, 2,9-phenanthrolin-6-yl group, 2,9-phenanthrolin-6-yl group, Nanthrolin-7-yl group, 2,9-phenanthrolin-8-yl group, 2,9-phenanthrolin-10-yl group, 2,8-phenanthrolin-1-yl group, 2,8 -phenanthrolin-3-yl group, 2,8-phenanthrolin-4-yl group, 2,8-phenanthrolin-5-yl group, 2,8-phenanthrolin-6-yl group, 2 , 8-phenanthrolin-7-yl group, 2,8-phenanthrolin-9-yl group, 2,8-phenanthrolin-10-yl group, 2,7-phenanthrolin-1-yl group , 2,7-phenanthrolin-3-yl group, 2,7-phenanthrolin-4-yl group, 2,7-phenanthrolin-5-yl group, 2,7-phenanthrolin-6-yl group yl group, 2,7-phenanthrolin-8-yl group, 2,7-phenanthrolin-9-yl group, 2,7-phenanthrolin-10-yl group, 1-phenazinyl group, 2-phenazinyl group group, 1-phenothiazinyl group, 2-phenothiazinyl group, 3-phenothiazinyl group, 4-phenothiazinyl group, 10-phenothiazinyl group, 1-phenoxazinyl group, 2-phenoxazinyl group, 3-phenoxazinyl group, 4-phenoxazinyl group group, 10-phenoxazinyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 2-oxadiazolyl group, 5-oxadiazolyl group, 3-furazanyl group, 2-thienyl group, 3-thienyl group, 2-methyl Pyrrol-1-yl group, 2-methylpyrrol-3-yl group, 2-methylpyrrol-4-yl group, 2-methylpyrrol-5-yl group, 3-methylpyrrol-1-yl group, 3-methyl Pyrrol-2-yl group, 3-methylpyrrol-4-yl group, 3-methylpyrrol-5-yl group, 2-t-butylpyrrol-4-yl group, 3-(2-phenylpropyl)pyrrole-1 -yl group, 2-methyl-1-indolyl group, 4-methyl-1-indolyl group, 2-methyl-3-indolyl group, 4-methyl-3-indolyl group, 2-t-butyl-1-indolyl group, Examples include 4-t-butyl 1-indolyl group, 2-t-butyl 3-indolyl group, and 4-t-butyl 3-indolyl group.
Among these, phenyl group, naphthyl group, biphenyl group, anthranyl group, phenanthryl group, pyrenyl group, chrysenyl group, fluoranthenyl group, and fluorenyl group are preferable.

Examples of the unsubstituted haloalkyl group having 1 to 50 carbon atoms include trifluoromethyl group, 2,2,2-trifluoroethyl group, pentafluoroethyl group, chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1,2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group , 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo-t-butyl group, 1,2,3-tribromopropyl group, Iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group, 2,3-diiodo-t-butyl group, 1,2, Examples include 3-triiodopropyl group.

Examples of the unsubstituted haloalkoxy group having 1 to 50 carbon atoms include trifluoromethoxy group, 1,1,2,2-tetrafluoroethoxy group, 2,2,3,3-tetrafluoropropoxy group, 2,2 , 2-trifluoroethoxy group, 2,2,3,3,3-pentafluoropropyl group, 2,2,3,3,4,4,4-heptafluorobutoxy group, nonafluoro-tert-butoxy group, etc. can be mentioned.

R ₉₀₁ to R ₉₀₅ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms; is an aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, and when two or more R _901s are present, two or more R _901s are: are the same or different from each other, and when two or more R _902s exist, two or more R _902s are the same or different from each other, and when two or more R _903s exist, two or more R ₉₀₃ are the same or different from each other, and when two or more R _904s exist, two or more R _904s are the same or different from each other, and when two or more R _905s exist, Two or more R ₉₀₅ 's are the same or different.
However, two adjacent ones selected from R ¹ to R ⁴ that are not single bonds bonded to *1 may bond to each other to form a substituted or unsubstituted benzene ring, and do not bond to each other, thus forming a ring. It does not need to be formed.

The details and preferred examples of the unsubstituted alkyl group having 1 to 50 carbon atoms are the same as the explanation of the substituent for R ¹ to R ⁴ that are not a single bond bonded to *1 above.

The details and preferred examples of the unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms are the same as the explanation of the substituent for R ¹ to R ⁴ that are not a single bond bonded to *1 above.

Details and preferred examples of the unsubstituted aryl group having 6 to 50 ring carbon atoms are the same as the explanation of the substituent for R ¹ to R ⁴ that are not a single bond bonded to *1 above.

The details and preferred examples of the unsubstituted heterocyclic group having 5 to 50 ring atoms are the same as the description of the substituent for R ¹ to R ⁴ that are not a single bond bonded to *1 above.

(R ⁵ to R ⁸ )
In the above formula (1), n selected from R ⁵ to R ⁸ are single bonds bonded to *2, and preferably R ⁷ is a single bond bonded to *2.
*R ⁵ to R ⁸ that are not single bonds bonded to *2 are each independently hydrogen atoms.

As mentioned above, "hydrogen atom" as used herein includes light hydrogen atoms, deuterium atoms, and tritium atoms. Therefore, compound A may contain a naturally occurring deuterium atom.
Further, deuterium atoms may be intentionally introduced into compound A by using a deuterated compound as part or all of the raw material compounds. Thus, in one aspect of the invention, compound A contains at least one deuterium atom. That is, compound A 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 addition, in the following, "substituted or unsubstituted", the number of carbon atoms, and the number of atoms are omitted.
When either Ar ¹ or Ar ² of formula (1) is an aryl group or a heterocyclic group, a hydrogen atom possessed by the aryl group or the heterocyclic group;
When any of L ¹ to L ³ in formula (1) is an arylene group or a divalent heterocyclic group, a hydrogen atom possessed by the arylene group or the divalent heterocyclic group;
When Ar ³ in formula (1) is an alkyl group, cycloalkyl group, aryl group, or heterocyclic group, a hydrogen atom possessed by the alkyl group, cycloalkyl group, aryl group, or heterocyclic group;
When either R ⁹ or R ¹⁰ in formula (1) is an alkyl group, a cycloalkyl group, an aryl group, or a heterocyclic group, the alkyl group, the cycloalkyl group, the aryl group, or the heterocyclic group Hydrogen atom possessed by;
A hydrogen atom represented by any of R ¹ to R ⁴ that is not a single bond bonded to *1 in formula (1);
Any one of R ¹ to R ⁴ that is not a single bond bonded to *1 in formula (1) is an alkyl group, alkenyl group, alkynyl group, cycloalkyl group, aryl group, aralkyl group, heterocyclic group, haloalkyl group, halo an alkoxy group, a group represented by -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ), a group represented by -O-(R ₉₀₄ ), or a group represented by -S-(R ₉₀₅ ); In some cases, the alkyl group, the alkenyl group, the alkynyl group, the cycloalkyl group, the aryl group, the aralkyl group, the heterocyclic group, the haloalkyl group, the haloalkoxy group, the -Si(R ₉₀₁ )( A hydrogen atom possessed by the group represented by R ₉₀₂ ) (R ₉₀₃ ), the group represented by -O-(R ₉₀₄ ), or the group represented by -S-(R ₉₀₅ );
*Hydrogen atoms represented by R ⁵ to R ⁸ that are not single bonds bonded to 2;

The deuteration rate of compound A depends on the deuteration rate of the raw material compound used. Even if a raw material with a predetermined deuteration rate is used, a certain proportion of naturally derived light hydrogen isotopes may be included. Therefore, the aspect of the deuteration rate of Compound A includes a ratio that takes into consideration a trace amount of naturally occurring isotope, compared to a ratio that is determined simply by counting the number of deuterium atoms represented by the chemical formula.
The deuteration rate of compound A is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, even more preferably 50% or more.

Compound A may be a mixture containing a deuterated compound and a non-deuterated compound, or a mixture of two or more compounds having different deuteration rates. The deuteration rate of such a mixture is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, even more preferably 50% or more, and 100% or more. less than %.
Further, the ratio of the number of deuterium atoms to the total number of hydrogen atoms in compound A is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, and 100% or more. % or less.

If the "substituted or unsubstituted XX group" included in the definitions of the above formulas is a substituted XX group, the details of the substituent are as described in "Substituents in the case of "substituted or unsubstituted"". and preferably an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 10 ring carbon atoms, an aryl group having 6 to 12 ring carbon atoms, or a heterocyclic group having 5 to 13 ring atoms ( (heteroaryl group), more preferably an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 12 ring carbon atoms. Details of each group (alkyl group, cycloalkyl group, aryl group, heterocyclic group) are as described above.

Compound A can be easily produced by those skilled in the art with reference to the following synthesis examples and known synthesis methods.

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

<Compound B>
Compound B is represented by the following formula (2) and is a compound different from compound A represented by formula (1), and is included in the compound B-containing hole transport layer in the organic layer of the organic EL element.

In formula (2), N ^* is the central nitrogen atom.

( ^LA1 , ^LA2 and ^LA3 )
In formula (2), L ^A1 , L ^A2 and L ^A3 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring-forming carbon atoms, or a substituted or unsubstituted ring-forming atom It is a divalent heterocyclic group having a number of 5 to 50, and is preferably a single bond or a substituted or unsubstituted phenylene group.

Examples of the unsubstituted arylene group having 6 to 50 ring carbon atoms include a phenylene group, a naphthylene group, a biphenylylene group, an anthrylene group, an acenaphtylene group, an anthranylene group, a phenanthrylene group, a phenarenylene group, a quinolylene group, an isoquinolylene group, and s. -indacenylene group, as-indacenylene group, chrysenylene group, etc.
Among these, a phenylene group, a naphthylene group, and a biphenylylene group are preferred, a phenylene group is more preferred, and a 1,4-phenylene group is even more preferred.

The unsubstituted divalent heterocyclic group having 5 to 50 ring atoms is an unsubstituted heterocyclic group having 5 to 50 ring atoms represented by R ¹ to R ⁴ that is not a single bond bonded to *1. A divalent group derived by removing one hydrogen atom on a heterocycle from a cyclic group is preferable.

(Ar ¹¹¹ , Ar ¹¹² and Ar ¹¹³ )
In formula (2), Ar ¹¹¹ , Ar ¹¹² and Ar ¹¹³ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring atoms, or a substituted or unsubstituted aryl group having 5 to 50 ring atoms. A heterocyclic group or a group represented by -Si(R ^C1 )(R ^C2 )(R ^C3 ), preferably the above formula (2A), the above formula (2B), the above formula (2C), the above formula It is represented by the formula (2D), the above formula (2E), or the above formula (2F). However, the description of "L ¹ or L ² " in the explanation of formulas (2A) to (2F) above shall be replaced with "L ^A1 , L ^A2 , or L ^A3 ."

Details and preferred examples of the unsubstituted aryl group having 6 to 50 ring carbon atoms represented by Ar ¹¹¹ , Ar ¹¹² and Ar ¹¹³ are the same substitutions for R ¹ to R ⁴ that are not a single bond bonded to *1 above. This is the same as the explanation for the group.

The details and preferred examples of the unsubstituted heterocyclic group having 5 to 50 ring atoms represented by Ar ¹¹¹ , Ar ¹¹² and Ar ¹¹³ are the same as those for R ¹ to R ⁴ that are not a single bond bonded to *1 above. This is the same as the explanation of the substituents.

((R ^C1 , R ^C2 and R ^C3 ))
R ^C1 , R ^C2 and R ^C3 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, and when a plurality of R ^C1s exist, the plurality of R ^C1s are the same as each other. or different, and when there is a plurality of R ^C2s , the plurality of R ^C2s are the same or different from each other, and when there is a plurality of R ^C3s , the plurality of R ^C3s are the same or different from each other. .

Details and preferred examples of the unsubstituted aryl group having 6 to 50 ring carbon atoms represented by R ^C1 , R ^C2 and R ^C3 include the same substitutions for R ¹ to R ⁴ that are not a single bond bonded to *1 above. This is the same as the explanation for the group.

(Formula (C11))
Compound B represented by formula (2) and different from compound A represented by formula (1) is preferably a compound represented by formula (C11) below.

In formula (C11), Ar ¹¹¹ , Ar ¹¹² , Ar ¹¹³ and ^LA2 are respectively synonymous with Ar ¹¹¹ , Ar ¹¹² , Ar ¹¹³ and ^LA2 in formula (2), and n1 and n3 are 4. ,
The plurality of R ^C11s are the same or different from each other,
One or more sets of two or more adjacent R ^C11s are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring. do not form or combine with each other;
A plurality of R ^C13s are the same or different from each other,
One or more sets of two or more adjacent R ^C13s are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring. do not form or combine with each other;
R ^C11 and R ^C13 which do not form a substituted or unsubstituted monocyclic ring and which do not form a substituted or unsubstituted condensed ring are each independently a hydrogen atom, a cyano group, a substituted or unsubstituted group having 1 carbon number, ~50 alkyl group, substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, group represented by -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ), -O-(R ₉₀₄ ) a substituted or unsubstituted aryl group having 6 to 50 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms.

((R ^C11 and R ^C13 ))
The details and preferred examples of the unsubstituted alkyl group having 1 to 50 carbon atoms are the same as the explanation of the substituent for R ¹ to R ⁴ that are not a single bond bonded to *1 above.

The details and preferred examples of the unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms are the same as the explanation of the substituent for R ¹ to R ⁴ that are not a single bond bonded to *1 above.

The details of the group represented by -Si(R ₉₀₁ ⁾ (R ₉₀₂ )(R ₉₀₃ ) and its preferred examples are ^as follows: The same is true.

The details of the group represented by -O-(R ₉₀₄ ) and its preferred examples are the same as the explanation of the substituent for R ¹ to R ⁴ that are not a single bond bonded to *1 above.

Details and preferred examples of the unsubstituted aryl group having 6 to 50 ring carbon atoms are the same as the explanation of the substituent for R ¹ to R ⁴ that are not a single bond bonded to *1 above.

The details and preferred examples of the unsubstituted heterocyclic group having 5 to 50 ring atoms are the same as the description of the substituent for R ¹ to R ⁴ that are not a single bond bonded to *1 above.

The unsubstituted monocyclic ring formed by a group consisting of two or more adjacent R ^C11s or a group consisting of two or more adjacent R ^C13s preferably has a ring-forming atom number of 3 to 6. It is a monocyclic ring, more preferably a benzene ring, a furan ring, or a thiophene ring, and still more preferably a benzene ring.

((Ar ¹¹¹ , Ar ¹¹² and Ar ¹¹³ ))
In one aspect of the present invention, in the compound represented by formula (2) or formula (C11), at least one of Ar ¹¹¹ , Ar ¹¹² and Ar ¹¹³ is represented by the following formula (21a) or the following formula (21b). , the following formula (21c), the following formula (21d) and the following formula (21e).

In formula (21a), formula (21b), formula (21c), formula (21d) and formula (21e),
X ₂₁ is NR ₂₁ , CR ₂₂ R ₂₃ , an oxygen atom or a sulfur atom,
When there are multiple _X21s , the multiple _X21s are the same or different,
When X ₂₁ is CR ₂₂ R ₂₃ , the set consisting of R ₂₂ and R ₂₃ are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring. not forming a ring or bonding to each other;
R ₂₁ , and R ₂₂ and R ₂₃ that do not form a substituted or unsubstituted monocycle or a substituted or unsubstituted fused ring each independently represent a hydrogen atom, a cyano group, a substituted or unsubstituted carbon Alkyl group having 1 to 50 carbon atoms, substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ₉₀₁ )(R ₉₀₂ )( A group represented by R ₉₀₃ ), a group represented by -O-(R ₉₀₄ ), a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms, or a substituted or unsubstituted aryl group having 5 to 5 ring atoms 50 heterocyclic groups,
One or more sets of two or more adjacent ones of R ₂₁₁ to R ₂₁₈ are bonded to each other to form a substituted or unsubstituted monocycle, or bonded to each other to form a substituted or unsubstituted fused ring. or do not combine with each other,
R ₂₁₁ to R ₂₁₈ that do not form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed ring are each independently a hydrogen atom, a cyano group, or a substituted or unsubstituted group having 1 to 50 carbon atoms. an alkyl group, a substituted or unsubstituted haloalkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ) a group represented by -O-(R ₉₀₄ ), a substituted or unsubstituted aryl group having 6 to 50 ring atoms, or a substituted or unsubstituted heterocycle having 5 to 50 ring atoms is the basis,
* in formula (21a), formula (21b), formula (21c), formula (21d), and formula (21e) is each independently a bonding position with ^LA1 , ^LA2 , or ^LA3 .

Details of the unsubstituted alkyl group having 1 to 50 carbon atoms represented by R ₂₁ , and R ₂₂ and R ₂₃ that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring, and their Preferred examples are the same as the explanation of the substituents for R ¹ to R ⁴ that are not a single bond bonded to *1 above.

As the unsubstituted unsubstituted haloalkyl group having 1 to 50 carbon atoms represented by R ₂₁ , and R ₂₂ and R ₂₃ which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted condensed ring; are chloromethyl group, 1-chloroethyl group, 2-chloroethyl group, 2-chloroisobutyl group, 1,2-dichloroethyl group, 1,3-dichloroisopropyl group, 2,3-dichloro-t-butyl group, 1 , 2,3-trichloropropyl group, bromomethyl group, 1-bromoethyl group, 2-bromoethyl group, 2-bromoisobutyl group, 1,2-dibromoethyl group, 1,3-dibromoisopropyl group, 2,3-dibromo- t-Butyl group, 1,2,3-tribromopropyl group, iodomethyl group, 1-iodoethyl group, 2-iodoethyl group, 2-iodoisobutyl group, 1,2-diiodoethyl group, 1,3-diiodoisopropyl group , 2,3-diiodo-t-butyl group, 1,2,3-triiodopropyl group, fluoromethyl group, 1-fluoroethyl group, 2-fluoroethyl group, 2-fluoroisobutyl group, 1,2-difluoroethyl group group, difluoromethyl group, trifluoromethyl group, pentafluoroethyl group, perfluoroisopropyl group, perfluorobutyl group, perfluorocyclohexyl group, and the like.
Among these, fluoromethyl group, trifluoromethyl group, pentafluoroethyl group, perfluoroisopropyl group, perfluorobutyl group, and perfluorocyclohexyl group are preferred.

R ₂₁ , and the unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms represented by R ₂₂ and R ₂₃ that do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted condensed ring; Details and preferred examples thereof are the same as the explanation of the substituents for R ¹ to R ⁴ that are not a single bond bonded to *1 above.

-Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ) represented by R ₂₁ , and R ₂₂ and R ₂₃ which do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted condensed ring; The details of the group represented and its preferred examples are the same as the explanation of the substituents for R ¹ to R ⁴ that are not a single bond bonded to *1 above.

Details of the group represented by -O-(R ₉₀₄ ) represented by R ₂₁ , and R ₂₂ and R ₂₃ that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring; Preferred examples thereof are the same as the explanation of the substituents for R ¹ to R ⁴ that are not single bonds bonded to *1 above.

Details of the unsubstituted aryl group having 6 to 50 ring carbon atoms represented by R ₂₁ , and R ₂₂ and R ₂₃ that do not form a substituted or unsubstituted monocyclic ring and do not form a substituted or unsubstituted condensed ring. And preferred examples thereof are the same as the explanation of the substituents for R ¹ to R ⁴ that are not a single bond bonded to *1 above.

R ₂₁ , and the unsubstituted heterocyclic group having 5 to 50 ring atoms represented by R ₂₂ and R ₂₃ that do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted condensed ring; Details and preferred examples thereof are the same as the explanation of the substituents for R ¹ to R ⁴ that are not a single bond bonded to *1 above.

Details and preferred examples of the unsubstituted alkyl group having 1 to 50 carbon atoms represented by R ₂₁₁ to R ₂₁₈ that do not form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed ring are as follows: This is the same as the explanation of the substituents for R ¹ to R ⁴ that are not single bonds bonded to *1 above.

Details and preferred examples of the unsubstituted haloalkyl group having 1 to 50 carbon atoms represented by R ₂₁₁ to R ₂₁₈ that do not form a substituted or unsubstituted monocyclic ring or a substituted or unsubstituted condensed ring are as follows: This is the same as the explanation of the substituents for R ₂₁ and R ₂₂ and R ₂₃ that do not form a substituted or unsubstituted monocycle and do not form a substituted or unsubstituted condensed ring.

Details of the unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms represented by R ₂₁₁ to R ₂₁₈ which does not form a substituted or unsubstituted monocyclic ring and which does not form a substituted or unsubstituted condensed ring and their preferred Examples are the same as the explanation of the substituents for R ¹ to R ⁴ that are not single bonds bonded to *1 above.

A group represented by the above -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ) represented by R ₂₁₁ to R ₂₁₈ that does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring. The details and preferred examples thereof are the same as the explanation of the substituent for R ¹ to R ⁴ that are not a single bond bonded to *1 above.

The details and preferred examples of the group represented by -O-(R ₉₀₄ ) represented by R ₂₁₁ to R ₂₁₈ which do not form a substituted or unsubstituted monocyclic ring and which do not form a substituted or unsubstituted condensed ring are as follows: , is the same as the explanation of the substituent for R ¹ to R ⁴ that is not a single bond bonded to *1 above.

Details and preferred examples of the unsubstituted aryl group having 6 to 50 ring carbon atoms represented by R ₂₁₁ to R ₂₁₈ that does not form a substituted or unsubstituted monocyclic ring and does not form a substituted or unsubstituted condensed ring. is the same as the explanation of the substituents for R ¹ to R ⁴ that are not single bonds bonded to *1 above.

Details of the unsubstituted heterocyclic group having 5 to 50 ring atoms represented by R ₂₁₁ to R ₂₁₈ which does not form a substituted or unsubstituted monocyclic ring and which does not form a substituted or unsubstituted condensed ring and their preferred Examples are the same as the explanation of the substituents for R ¹ to R ⁴ that are not single bonds bonded to *1 above.

In one embodiment of the present invention, Ar ¹¹¹ , Ar ¹¹² and Ar ¹¹³ are each independently preferably a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms, and preferably a substituted or unsubstituted phenyl group or a substituted or unsubstituted biphenyl group. More preferred.

In one embodiment of the present invention, in the compound represented by formula (C11), two of Ar ¹¹¹ , Ar ¹¹² and Ar ¹¹³ are represented by formula (21a), formula (21b), formula (21c), or formula (21d ) and the group represented by formula (21e), and the other one of Ar ¹¹¹ , Ar ¹¹² and Ar ¹¹³ is a substituted or unsubstituted ring having 6 to 30 carbon atoms. It is also preferable that it is an aryl group.

In one aspect of the present invention, in the compound represented by formula (C11), one of Ar ¹¹¹ , Ar ¹¹² and Ar ¹¹³ is represented by formula (21a), formula (21b), formula (21c), or formula (21d ) and the group represented by formula (21e), and the other two of Ar ¹¹¹ , Ar ¹¹² and Ar ¹¹³ are substituted or unsubstituted rings having 6 to 30 carbon atoms. It is also preferable that it is an aryl group.

As mentioned above, "hydrogen atom" as used herein includes light hydrogen atoms, deuterium atoms, and tritium atoms. Therefore, compound B may contain a naturally occurring deuterium atom.
Further, deuterium atoms may be intentionally introduced into compound B by using a deuterated compound as part or all of the raw material compounds. Thus, in one aspect of the invention, compound B contains at least one deuterium atom. That is, compound B is a compound represented by formula (2) that is different from compound A represented by formula (1), and at least one of the hydrogen atoms contained in the compound is a deuterium atom. There may be.

At least one hydrogen atom selected from the following hydrogen atoms may be a deuterium atom. In addition, in the following, "substituted or unsubstituted", the number of carbon atoms, and the number of atoms are omitted.
When any of L ^A1 , L ^A2 and L ^A3 in formula (2) is an arylene group or a divalent heterocyclic group, a hydrogen atom possessed by the arylene group or the divalent heterocyclic group;
When Ar ¹¹¹ , Ar ¹¹² and Ar ¹¹³ in formula (2) are an aryl group, a heterocyclic group, or a group represented by -Si(R ^C1 )(R ^C2 )(R ^C3 ), the aryl group, the a hydrogen atom possessed by a heterocyclic group or a group represented by -Si(R ^C1 )(R ^C2 )(R ^C3 );

The deuteration rate of compound B depends on the deuteration rate of the raw material compound used. Even if a raw material with a predetermined deuteration rate is used, a certain proportion of naturally derived light hydrogen isotopes may be included. Therefore, the aspect of the deuteration rate of compound B includes a ratio that takes into account a trace amount of naturally occurring isotope, with respect to a ratio that is determined simply by counting the number of deuterium atoms represented by the chemical formula.
The deuteration rate of compound B is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, even more preferably 50% or more.

Compound B may be a mixture containing a deuterated compound and a non-deuterated compound, or a mixture of two or more compounds having different deuteration rates. The deuteration rate of such a mixture is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, even more preferably 50% or more, and 100% or more. less than %.
Further, the ratio of the number of deuterium atoms to the total number of hydrogen atoms in compound B is preferably 1% or more, more preferably 3% or more, even more preferably 5% or more, even more preferably 10% or more, and 100% or more. % or less.

If the "substituted or unsubstituted XX group" included in the definitions of the above formulas is a substituted XX group, the details of the substituent are as described in "Substituents in the case of "substituted or unsubstituted"". and preferably an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 50 carbon atoms, an aryl group having 6 to 12 ring atoms, or an aromatic heterocyclic group having 5 to 13 ring atoms ( (heteroaryl group), more preferably an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 50 carbon atoms, or an aryl group having 6 to 12 ring carbon atoms. Details of each group (alkyl group, cycloalkyl group, aryl group, aromatic heterocyclic group) are as described above.

Compound B can be easily produced by those skilled in the art with reference to the following synthesis examples and known synthesis methods.

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

<Details of organic EL element>
The organic EL device of the present invention has a cathode, an anode, and an organic layer between the cathode and the anode.
The organic layer includes a light emitting layer and a hole transport zone between the anode and the light emitting layer.
The hole transport zone exists in the compound A-containing hole transport layer containing compound A represented by formula (1) and on the light-emitting layer side from the compound A-containing hole transport layer, and ) and a compound B-containing hole transport layer containing a compound B different from compound A represented by formula (1), other than the compound A-containing hole transport layer and the compound B-containing hole transport layer. It is preferable to further include a hole transport layer (a hole injection layer, an electron blocking layer, an exciton blocking layer, etc.) adjacent to the compound A-containing hole transport layer.
Note that the hole transport layers other than the compound A-containing hole transport layer and the compound B-containing hole transport layer do not contain either compound A or compound B.

Further, it is preferable that a hole transport layer other than the compound A-containing hole transport layer and the compound B-containing hole transport layer be present between the compound A-containing hole transport layer and the compound B-containing hole transport layer. .

Moreover, it is preferable that the refractive index of the second hole transport layer existing on the light emitting layer side of the two layers, the compound A-containing hole transport layer and the other hole transport layer, is 1.85 or less.

Moreover, the refractive index of the first hole transport layer existing on the anode side of the two layers of the compound A-containing hole transport layer and the other hole transport layer is the same as that of the compound A-containing hole transport layer and the other hole transport layer. It is preferable that the refractive index of the second hole transport layer is larger than that of the second hole transport layer which is present on the light emitting layer side of the two layers.

Furthermore, of the two layers, the compound A-containing hole transport layer and the other hole transport layer, the second hole transport layer, which is present on the light emitting layer side, preferably has a thickness of 20 to 75 nm.

Further, the compound B-containing hole transport layer is preferably a layer adjacent to the light emitting layer.

Other examples of organic layers included in organic EL devices include a space layer, an electron transport zone (electron injection layer, electron transport layer, hole blocking layer, etc.) provided between a cathode and a light emitting layer, etc. , but not limited to these.

The organic EL device that is one embodiment of the present invention may be a monochromatic fluorescent or phosphorescent light emitting device, a fluorescent/phosphorescent hybrid white light emitting device, or a simple type having a single light emitting unit. It may also be a tandem type having a plurality of light emitting units, and a fluorescent light emitting type element is particularly preferable. Here, the "light-emitting unit" refers to a minimum 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, as a typical element configuration of a simple organic EL element, the following element configuration can be mentioned.
(1) Anode/Light-emitting unit/Cathode Further, the light-emitting unit may be a multilayer type having a plurality of phosphorescence-emitting layers or fluorescent light-emitting layers. A space layer may be provided for the purpose of preventing excitons from diffusing into 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/) First hole transport layer/Second hole transport layer/Fluorescence emitting layer/Electron transport layer (/Electron injection layer)
(b) (Hole injection layer/) First hole transport layer/Second hole transport layer/First fluorescent layer/Second fluorescent layer/Electron transport layer (/Electron injection layer)
(c) (Hole injection layer/) First hole transport layer/Second hole transport layer/Phosphorescent layer/Space layer/Fluorescent layer/Electron transport layer (/Electron injection layer)
(d) (Hole injection layer/) First hole transport layer/Second hole transport layer/First phosphorescent layer/Second phosphorescent layer/Space layer/Fluorescent layer/Electron transport layer (/Electron injection layer layer)
(e) (Hole injection layer/) First hole transport layer/Second hole transport layer/Phosphorescent layer/Space layer/First fluorescent layer/Second fluorescent layer/Electron transport layer (/Electron injection layer layer)
(f) (Hole injection layer/) First hole transport layer/Second hole transport layer/Exciton blocking layer/Fluorescence emitting layer/Electron transport layer (/Electron injection layer)
(g) (Hole injection layer/) First hole transport layer/Second hole transport layer/Fluorescence emitting layer/First electron transport layer/Second electron transport layer (/Electron injection layer)
(h) (Hole injection layer/) First hole transport layer/Second hole transport layer/Fluorescence emitting layer/Hole blocking layer/Electron transport layer (/Electron injection layer)
(i) (Hole injection layer/) First hole transport layer/Second hole transport layer/Fluorescence emitting layer/Exciton blocking layer/Electron transport layer (/Electron injection layer)
(j) (Hole injection layer/) First hole transport layer/Second hole transport layer/First fluorescent light emitting layer/Second fluorescent light emitting layer/First electron transport layer/Second electron transport layer (/Electron injection layer)
(k) (Hole injection layer/) First hole transport layer/Second hole transport layer/Third hole transport layer/First fluorescent layer/Second fluorescent layer/First electron transport layer/First 2 Electron transport layer (/electron injection layer)

Each of the phosphorescent or fluorescent light-emitting layers may emit light of a different color from each other. Specifically, in the light emitting unit (d), (hole injection layer/) first hole transport layer/second hole transport layer/first phosphorescent layer (red light emitting)/second phosphorescent layer ( The layer structure may include a green light emitting layer)/a space layer/a fluorescent light emitting layer (blue light emitting layer)/an electron transporting layer.
Note that an electron blocking layer may be provided between each light emitting layer and the hole transport layer or space layer, as appropriate. Further, a hole blocking layer may be provided between each light emitting layer and the electron transport layer as appropriate. By providing an electron blocking layer or a hole blocking layer, it is possible to confine electrons or holes within the light emitting layer, increase the probability of charge recombination in the light emitting layer, and improve luminous efficiency.
Further, a hole transport layer adjacent to the light emitting layer in a multilayer structure including two or more hole transport layers, for example, the second hole transport layer of the two-layer structure or the third hole transport layer of the three-layer structure However, it may also have a function as an electron blocking layer. That is, when the hole transport layer has a multilayer structure including two or more hole transport layers, the hole transport layer adjacent to the light emitting layer in the multilayer structure can also be used as an electron blocking layer.

Typical device configurations of tandem type organic EL devices include the following device configurations.
(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 independently selected from the above light emitting units, for example. .
Further, one of the first light emitting unit and the second light emitting unit may be selected from the light emitting units described above, and the other light emitting unit may be selected from the above-mentioned simple type light emitting unit. A light emitting unit having a single layer transport layer may be selected.
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 supplies electrons to the first light emitting unit and holes to the second light emitting unit. Any known material configuration can be used.

FIG. 1 is a schematic diagram showing an example of the structure of an organic EL element according to one embodiment of the present invention. The organic EL element 1 includes a substrate 2, an anode 3, a cathode 4, and a light emitting unit 10 disposed between the anode 3 and the cathode 4. The light emitting unit 10 has a light emitting layer 5. A hole transport zone 6 (hole injection layer, hole transport layer, etc.) is formed between the light emitting layer 5 and the anode 3, and an electron transport zone 7 (electron injection layer, electron transport layer, etc.) is formed between the light emitting layer 5 and the cathode 4. etc.). Further, an electron blocking layer (not shown) may be provided on the anode 3 side of the light emitting layer 5, and a hole blocking layer (not shown) may be provided on the cathode 4 side of the light emitting layer 5. Thereby, electrons and holes can be confined in the light-emitting layer 5, and the efficiency of exciton generation in the light-emitting layer 5 can be further increased.

FIG. 2 is a schematic diagram showing another structure of an organic EL element according to one embodiment of the present invention. The organic EL element 11 includes 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. Further, the electron transport zone arranged between the light emitting layer 5 and the cathode 4 is formed from the first electron transport layer 7a and the second electron transport layer 7b.
Moreover, in one aspect of the present invention, it is preferable that the compound A-containing hole transport layer and the compound B-containing hole transport layer are in direct contact. Moreover, it is preferable that the compound B-containing hole transport layer is a layer adjacent to the light emitting layer. Therefore, in one embodiment of the present invention, for example, when explaining using the structure of the organic EL element shown in the schematic diagram of FIG. 2, the first hole transport layer 6b is the hole transport layer containing the compound A, It is more preferable that the second hole transport layer 6c is a hole transport layer containing the compound B and also an electron blocking layer.

FIG. 3 is a schematic diagram showing another configuration of the organic EL element of the present invention. The organic EL element 12 includes 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 arranged between the anode 3 and the light emitting layer 5 is formed from a hole injection layer 6a, a first hole transport layer 6b, a second hole transport layer 6c, and a third hole transport layer 6d. has been done. Further, the electron transport zone arranged between the light emitting layer 5 and the cathode 4 is formed from the first electron transport layer 7a and the second electron transport layer 7b.
Moreover, in one aspect of the present invention, it is preferable that the compound B-containing hole transport layer is a layer adjacent to the light emitting layer. Therefore, in one embodiment of the present invention, for example, when explaining using the structure of an organic EL element shown in the schematic diagram of FIG. 3, the first hole transport layer 6b or the second hole transport layer 6c is It is preferable that the third hole transport layer 6d is a hole transport layer containing compound B and is an electron blocking layer.
Moreover, in one aspect of the present invention, it is preferable that the compound A-containing hole transport layer and the compound B-containing hole transport layer are in direct contact. Therefore, in one embodiment of the present invention, for example, when explaining using the structure of the organic EL element shown in the schematic diagram of FIG. 3, the second hole transport layer 6c is the hole transport layer containing the compound A, It is more preferable that the third hole transport layer 6d is a hole transport layer containing the compound B and also an electron blocking layer.

In the present invention, a host combined with a fluorescent dopant material (fluorescent material) is referred to as a fluorescent host, and a host combined with a phosphorescent dopant material is referred to as a phosphorescent host. Fluorescent hosts and phosphorescent hosts are not distinguished only by molecular structure. That is, the phosphorescent host refers to a material containing a phosphorescent dopant that forms a phosphorescent layer, and does not mean that it cannot be used as a material to form a fluorescent layer. The same applies to fluorescent hosts.

(substrate)
The substrate is used as a support for the organic EL element. As the substrate, for example, a plate of glass, quartz, plastic, etc. can be used. Alternatively, a flexible substrate may be used. Examples of the flexible substrate include plastic substrates made of polycarbonate, polyarylate, polyethersulfone, polypropylene, polyester, polyvinyl fluoride, and polyvinyl chloride. Moreover, an inorganic vapor-deposited film can also be used.

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

These materials are usually formed into films by sputtering. For example, for indium oxide-zinc oxide, use a target in which 1 to 10 wt% of zinc oxide is added to indium oxide, and for indium oxide containing tungsten oxide and zinc oxide, 0.5 to 5 wt% of tungsten oxide is added to indium oxide. %, and by using a target containing 0.1 to 1 wt % zinc oxide, it can be formed by a sputtering method. In addition, it may be produced by a vacuum evaporation method, a coating method, an inkjet method, a spin coating method, or the like.

(hole transport band)
As mentioned above, the organic layer may include a hole transport zone between the anode and the emissive layer. The hole transport zone is composed of a hole injection layer, a hole transport layer, an electron blocking layer, and the like. The hole transport zone may include one or more layers of a hole injection layer, a hole transport layer, and an electron blocking layer. That is, the hole transport zone may include one or more layers in addition to the compound A-containing hole transport layer and the compound B-containing hole transport layer. For example, layer C may be included between the compound A-containing hole transport layer and the anode (however, layer C is not "another hole transport layer"), and between layer C and the anode, layer C may be included. Layer D (provided that Layer D is not an "other hole transport layer"), and each layer in the hole transport zone that is not an "other hole transport layer" may contain two or more compounds. It may be a mixed layer containing Compound A and Compound B as one embodiment.
When there are multiple layers containing compound A, the layer closest to the anode is the compound A-containing hole transport layer.
When a plurality of layers containing compound B are present, the layer closest to the light-emitting layer is the compound B-containing hole transport layer.
From the above, for example, (1) anode/layer D containing compound A (hole injection layer)/layer C containing compound B (hole transport layer)/hole transport layer containing compound A/compound A and the compound Structure of other hole transport layer not containing B/hole transport layer containing compound B/light emitting layer, (2) Anode/layer D containing compound A (hole injection layer)/layer C containing compound B (Hole transport layer)/Compound A-containing hole transport layer/Compound B-containing hole transport layer/Light emitting layer configuration, etc. are included in the present invention.

The hole injection layer formed in contact with the anode is formed using a material that can easily inject holes regardless of the work function of the anode. , alloys, electrically conductive compounds, mixtures thereof, and elements belonging to Group 1 or Group 2 of the Periodic Table of Elements).
Elements belonging to Group 1 or Group 2 of the periodic table of elements, which are materials with a small work function, such as alkali metals such as lithium (Li) and cesium (Cs), as well as magnesium (Mg), calcium (Ca), and strontium. Alkaline earth metals such as (Sr), alloys containing these (for example, MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), alloys containing these, etc. can also be used. In addition, when forming an anode using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Furthermore, when silver paste or the like is used, a coating method, an inkjet method, etc. can be used.

((hole injection layer))
The hole injection layer is a layer containing a material with high hole injection property (hole injection material), and is located between the anode and the light emitting layer or, if present, between the hole transport layer and the anode. It is formed.

Examples of hole injection materials that can be used include molybdenum oxide, titanium oxide, vanadium oxide, rhenium oxide, ruthenium oxide, chromium oxide, zirconium oxide, hafnium oxide, tantalum oxide, silver oxide, tungsten oxide, and manganese oxide.

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-diphenylaminophenyl)-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), 3-[N-(1-naphthyl)-N Aromatic amine compounds such as -(9-phenylcarbazol-3-yl)amino]-9-phenylcarbazole (abbreviation: PCzPCN1) are also exemplified as hole injection layer materials.

High molecular compounds (oligomers, dendrimers, polymers, etc.) can also be used. For example, poly(N-vinylcarbazole) (abbreviation: PVK), poly(4-vinyltriphenylamine) (abbreviation: PVTPA), poly[N-(4-{N'-[4-(4-diphenylamino) phenyl]phenyl-N'-phenylamino}phenyl) methacrylamide] (abbreviation: PTPDMA), poly[N,N'-bis(4-butylphenyl)-N,N'-bis(phenyl)benzidine] (abbreviation: Polymer compounds such as Poly-TPD) can be mentioned. Additionally, a polymer compound to which an acid is added, such as poly(3,4-ethylenedioxythiophene)/poly(styrene sulfonic acid) (PEDOT/PSS) or polyaniline/poly(styrene sulfonic acid) (PAni/PSS), is used. You can also do that.

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

((hole transport layer, electron blocking layer))
The hole transport layer is a layer containing a material with high hole transport properties (hole transport material), and is located between the anode and the light emitting layer or, if present, between the hole injection layer and the light emitting layer. is formed. In a multilayer structure including two or more hole transport layers, the hole transport layer adjacent to the light emitting layer can also be used as an electron blocking layer.

The hole transport layer has a multilayer structure including two or more layers. For example, the hole transport layer may have a two-layer structure including a first hole transport layer (on the anode side) and a second hole transport layer (on the 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. Further, the hole transport layer may have a three-layer structure including, in order from the anode side, a first hole transport layer, a second hole transport layer, and a third hole transport layer. That is, the third hole transport layer may be arranged between the second hole transport layer and the light emitting layer.
In one aspect of the present invention, the hole transport layer closest to the cathode in the multilayer structure, for example, the second hole transport layer in the two-layer structure or the third hole transport layer in the three-layer structure is a light-emitting layer. Preferably, they are adjacent (directly in contact). In another embodiment of the present invention, an electron blocking layer or the like may be interposed between the hole transport layer closest to the light emitting layer and the light emitting layer in the multilayer structure. Further, as described above, in a multilayer structure including two or more hole transport layers, the hole transport layer adjacent to the light emitting layer can also be used as an electron blocking layer.
When the hole transport layer has a three-layer structure, at least one of the first or second hole transport layer is a compound A-containing hole transport layer containing compound A, and At least one of the second or third hole transport layers present on the light emitting layer side is a compound B-containing hole transport layer containing compound B.
As long as the compound B-containing hole-transporting layer is present closer to the light-emitting layer than the compound-A-containing hole-transporting layer, compound A can be added to only one of the first or second hole-transporting layer (the first hole-transporting layer). or only the second hole transport layer), or only any two of 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 may be included in the first to third hole transport layers. may be included in all.
As long as the compound B-containing hole-transporting layer is present closer to the light emitting layer than the compound A-containing hole-transporting layer, compound B can be added to only one of the second or third hole-transporting layers (second hole-transporting layer). or only the third hole transport layer), or only any two of 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 may be included in the first to third hole transport layers. may be included in all.
In one aspect of the present invention, Compound A and Compound B contained in each of the transport layers are preferably light hydrogen bodies from the viewpoint of manufacturing cost.
The light hydrogen compound refers to a compound in which all hydrogen atoms in Compound A and Compound B are light hydrogen atoms.
Therefore, the present invention provides one or both of the first hole transport layer and the second hole transport layer (in the case of a two-layer structure), at least one of the first to third hole transport layers (in the case of a three-layer structure). case) includes an organic EL element containing a compound A consisting essentially only of light hydrogen, one or both of the first hole transport layer and the second hole transport layer (in the case of a two-layer structure), the first to At least one of the third hole transport layers (in the case of a three-layer structure) includes an organic EL element containing a compound B consisting essentially of a light hydrogen substance. "Compound A consisting essentially only of light hydrogen bodies" means that the content ratio of light hydrogen bodies to the total amount of compound A is 90 mol% or more, preferably 95 mol% or more, more preferably 99 mol% or more (each "Compound B consisting essentially only of light hydrogen bodies" means that the content of light hydrogen bodies with respect to the total amount of Compound B is 90 mol% or more, preferably 95 mol % or more, more preferably 99 mol % or more (each including 100%).

As the material for the hole transport layer other than compound A and compound B, for example, aromatic amine compounds, carbazole derivatives, anthracene derivatives, etc. can be used.
Examples of the aromatic amine compound include 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (abbreviation: NPB) and N,N'-bis(3-methylphenyl)- N,N'-diphenyl-[1,1'-biphenyl]-4,4'-diamine (abbreviation: TPD), 4-phenyl-4'-(9-phenylfluoren-9-yl)triphenylamine (abbreviation) :BAFLP), 4,4'-bis[N-(9,9-dimethylfluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: DFLDPBi), 4,4',4''-tris(N, N-diphenylamino)triphenylamine (abbreviation: TDATA), 4,4',4''-tris[N-(3-methylphenyl)-N-phenylamino]triphenylamine (abbreviation: MTDATA), and 4 , 4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB). The above compound has a hole mobility of 10 ⁻⁶ cm ² /Vs or more.

Examples of the 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 the 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 higher hole transport properties than electron transport properties.

In one embodiment of the organic EL element having a two-layer structure or two or more hole transport layers according to the present invention, the first hole transport layer may contain a compound represented by the following formula (12).
In the organic EL element having a three-layer hole transport layer according to the present invention, one or both of the first hole transport layer and the second hole transport layer may contain one or more compounds represented by the following (12).
In the organic EL element according to the present invention having a hole transport layer of an n-layer structure (n is an integer of 4 or more), at least one of the first hole transport layer to the (n-1)th hole transport layer may contain one or more compounds represented by formula (12).
[In the formula (12),
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 the same 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 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 (12), A ² , B ² , C ² , and D ² are preferably each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenyl group, or a substituted or unsubstituted terphenyl group. group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibensofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, and a substituted or unsubstituted carbazolyl group.
More preferably, in formula (12), at least one of A ² , B ² , C ² and D ² is a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted terphenyl group, or a substituted or unsubstituted terphenyl group. a naphthyl group, a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted dibensofuranyl group, a substituted or unsubstituted dibenzothiophenyl group, or a substituted or unsubstituted carbazolyl group.

The fluorenyl group that A ² , B ² , C ² , and D ² can have may have a substituent at the 9-position, such as 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, and 9,9-diphenylfluorenyl group. It may also be an olenyl group. Further, the substituents at the 9-position may form a ring, for example, the substituents at the 9-position may form a fluorene skeleton or a xanthene skeleton.

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.

The substituted or unsubstituted arylene group having 6 to 12 ring carbon atoms is preferably each independently a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, or a substituted or unsubstituted naphthylene group. .
The phenylene group is an o-phenylene group, m-phenylene group, or p-phenylene group, with p-phenylene group being particularly preferred.
The biphenylene group is preferably a 4,2'-biphenylene group, a 4,3'-biphenylene group, a 4,4'-biphenylene group, or a 3,3'-biphenylene group, more preferably a 4,3'-biphenylene group. Biphenylene group, 4,4'-biphenylene group, or 3,3'-biphenylene group, particularly preferably 4,4'-biphenylene group.
The naphthylene group is preferably a 1,4-naphthylene group, a 2,6-naphthylene group, a 1,5-naphthylene group, or a 1,8 naphthylene group.

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

(emission band)
The light-emitting band is composed of a single light-emitting layer, a plurality of light-emitting layers, a space layer located between the plurality of light-emitting layers and each light-emitting layer, and the like. In one embodiment of the present invention, the light-emitting layer preferably includes two or more layers.

(Dopant material for light emitting layer)
The light-emitting layer is a layer containing a highly luminescent material (dopant material), and various materials can be used. For example, a fluorescent material or a phosphorescent material can be used as a dopant material. 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 element according to the present invention, the light emitting layer is preferably a single layer.
Furthermore, in another embodiment of the organic EL element according to the present invention, the light-emitting layer preferably includes a first light-emitting layer and a second light-emitting layer.

As the blue fluorescent material that can be used in the light emitting layer, pyrene derivatives, styrylamine derivatives, chrysene derivatives, fluoranthene derivatives, fluorene derivatives, diamine derivatives, triarylamine derivatives, etc. can be used. Specifically, 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).

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-carbazol-3-amine (abbreviation: 2PCAPA), N-[9,10-bis(1,1 '-biphenyl-2-yl)-2-anthryl]-N,9-diphenyl-9H-carbazol-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-carbazole) -9-yl)phenyl]-N-phenylanthracen-2-amine (abbreviation: 2YGABPhA), N,N,9-triphenylanthracen-9-amine (abbreviation: DPhAPhA), and the like.

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

In one embodiment 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-based 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), etc. Can be mentioned.

An iridium complex or the like is used as a green phosphorescent material that can be used in the light emitting layer. 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)), bis(benzo[ h] quinolinato) iridium (III) acetylacetonate (abbreviation: Ir(bzz)2(acac)), and the like.

Metal complexes such as iridium complexes, platinum complexes, terbium complexes, and europium complexes are used as red-colored phosphorescent materials that can be used in the light-emitting layer. Specifically, 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-fluoro) phenyl)quinoxalinato]iridium(III) (abbreviation: Ir(Fdpq)2(acac)), 2,3,7,8,12,13,17,18-octaethyl-21H,23H-porphyrin platinum(II) (abbreviation) :PtOEP) and other organometallic complexes.

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

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

(Host material of luminescent layer)
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 that has a higher lowest unoccupied orbital level (LUMO level) and a lower highest occupied orbital level (HOMO level) than the dopant material.
Examples of host materials include (1) metal complexes such as aluminum complexes, beryllium complexes, or zinc complexes;
(2) Heterocyclic compounds such as oxadiazole derivatives, benzimidazole derivatives, or phenanthroline derivatives,
(3) fused aromatic compounds such as carbazole derivatives, anthracene derivatives, phenanthrene derivatives, pyrene derivatives, or chrysene derivatives,
(4) Aromatic amine compounds such as triarylamine derivatives or fused polycyclic aromatic amine derivatives are used.
In one aspect of the organic EL device according to the present invention, the light-emitting layer may include (3) a fused aromatic compound such as a carbazole derivative, an anthracene derivative, a phenanthrene derivative, a pyrene derivative, or a chrysene derivative as a host material. Preferably, among these, it is more preferable to include anthracene derivatives (also referred to as "anthracene compounds").
In one embodiment of the organic EL device according to the present invention, the anthracene compound that the light emitting layer may contain as a suitable host material is preferably an anthracene compound having an anthracene ring and a dibenzofuran ring.

For example, 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), bis[2-(2-benzothiazolyl)phenolato]zinc(II) (abbreviation: ZnBTZ), etc. ;
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-benzentriyl)tris(1-phenyl-1H-benzimidazole) (abbreviation: TPBI), bathophenanthroline ( Heterocyclic compounds such as abbreviation: BPhen), 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-BuDNA), 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)tripyrene ( Condensed aromatic compounds such as abbreviation: TPB3), 9,10-diphenylanthracene (abbreviation: DPAnth), 6,12-dimethoxy-5,11-diphenylchrysene; 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-carbazol-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-phenyl Aromatic amine compounds such as amino]biphenyl (abbreviation: DFLDPBi), 4,4'-bis[N-(spiro-9,9'-bifluoren-2-yl)-N-phenylamino]biphenyl (abbreviation: BSPB) can be used. Multiple types of host materials may be used.

In particular, in the case of a blue fluorescent element, it is preferable to use the following anthracene compound as the host material.

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 contains the second light-emitting layer. It is different from the constituent components. 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. Different aspects are mentioned.

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

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 (300K). The emission spectrum can be measured using a spectrofluorometer (device name: F-7000) manufactured by Hitachi High-Tech Science Co., Ltd. Note that the emission spectrum measuring device is not limited to the device used here.
In the emission spectrum, the peak wavelength of the emission spectrum 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 fluorescence 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 may be the fluorescent compound.
Further, 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 contains the fluorescent compound. Alternatively, both of the light-emitting layers may contain the fluorescent compound. When the first light-emitting layer contains the fluorescent compound, only one of the dopant material and the host material contained in the first light-emitting layer may be the fluorescent compound, or both may be the fluorescent compound. There may be. Further, when the second light emitting layer contains the fluorescent compound, only one of the dopant material and the host material contained in the second light emitting layer may be the fluorescent compound, or both may be the fluorescent compound. It may be a sexual compound.

The film thickness in the emission band of the organic EL element is preferably 5 nm or more and 50 nm or less, more preferably 7 nm or more and 50 nm or less, and even more preferably 10 nm or more and 50 nm or less. If the film thickness of the emission band is 5 nm or more, it will be easier to form the emission band and the chromaticity will also be easier to adjust. If the film thickness in the emission band is 50 nm or less, it becomes easier to suppress an increase in drive voltage.

(electron transport band)
The electron transport zone is composed of an electron injection layer, an electron transport layer, a hole blocking layer, and the like. Any layer of the electron transport zone, in particular the electron transport layer, preferably comprises alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, alkali Selected from the group consisting of earth metal halides, rare earth metal oxides, rare earth metal halides, organic complexes containing alkali metals, organic complexes containing alkaline earth metals, and organic complexes containing rare earth metals. Contains one or more of the following.

(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 have a single layer structure or a multilayer structure including two or more layers. For example, the electron transport layer may have a two-layer structure including a first electron transport layer (on the anode side) and a second electron transport layer (on the cathode side). In one aspect of the present invention, the single-layer structure electron transport layer is preferably adjacent to (directly in contact with) the light emitting layer, and the electron transport layer closest to the anode in the multilayer structure, for example, It is preferable that the first electron transport layer of the two-layer structure is adjacent to (directly in contact with) the light emitting layer. In another aspect of the present invention, the hole blocking described below is provided between the electron transport layer and the light emitting layer of the single layer structure, or between the electron transport layer and the light emitting layer closest to the light emitting layer in the multilayer structure. A layer or the like may be interposed.
The electron transport layer includes, for example,
(1) Metal complexes such as aluminum complexes, beryllium complexes, zinc complexes,
(2) Heteroaromatic compounds such as imidazole derivatives, benzimidazole derivatives, azine derivatives, carbazole derivatives, phenanthroline derivatives,
(3) High molecular 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 the heteroaromatic compound 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)-1,2,4-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) are listed. It will be done.

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

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

The electron transport layer may be a single layer or a multilayer including two or more layers. For example, the electron transport layer may include a first electron transport layer (on the anode side) and a second electron transport layer (on the cathode side). The two or more electron transport layers are each formed from the electron transport material.

(electron injection layer)
The electron injection layer is a layer containing a material with high electron injection properties. The electron injection layer contains alkali metals such as lithium (Li) and cesium (Cs), alkaline earth metals such as magnesium (Mg), calcium (Ca), and strontium (Sr), europium (Eu), and ytterbium (Yb). Rare earth metals such as these 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, and rare earth metal oxides. Examples include lithium fluoride (LiF), cesium fluoride (CsF), calcium fluoride (CaF2), lithium oxide (LiOx), etc.). Moreover, a plurality of these compounds can also be used in combination.
In addition, a material having an electron transporting property containing an alkali metal, an alkaline earth metal, or a compound thereof, specifically a material containing magnesium (Mg) in Alq, may be used. Note that in this case, electron injection from the cathode can be performed more efficiently.
Alternatively, a composite material made of a mixture of an organic compound and an electron 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 an electron donor. In this case, the organic compound is preferably a material that is excellent in transporting received electrons, and specifically, for example, the above-mentioned materials constituting the electron transport layer (metal complexes, heteroaromatic compounds, etc.) are used. be able to. The electron donor may be any material as long as it exhibits electron donating properties to organic compounds. Specifically, alkali metals, alkaline earth metals, and rare earth metals are preferred, and examples include lithium, cesium, magnesium, calcium, erbium, and ytterbium. Moreover, alkali metal oxides and alkaline earth metal oxides are preferable, and examples thereof include lithium oxide, calcium oxide, barium oxide, and the like. Additionally, Lewis bases such as magnesium oxide can also be used. Moreover, organic compounds such as tetrathiafulvalene (abbreviation: TTF) can also be used.

(cathode)
For the cathode, it is preferable to use metals, alloys, electrically conductive compounds, mixtures thereof, etc. with a small work function (specifically, 3.8 eV or less). Specific examples of such cathode materials include elements belonging to Group 1 or Group 2 of the periodic table of elements, that is, alkali metals such as lithium (Li) and cesium (Cs), and magnesium (Mg) and calcium (Ca). ), alkaline earth metals such as strontium (Sr), alloys containing these (for example, MgAg, AlLi), rare earth metals such as europium (Eu), ytterbium (Yb), and alloys containing these.
In addition, when forming a cathode using an alkali metal, an alkaline earth metal, or an alloy containing these, a vacuum evaporation method or a sputtering method can be used. Further, when using silver paste or the like, a coating method, an inkjet method, etc. can be used.
By providing an electron injection layer, the cathode can be formed using various conductive materials such as Al, Ag, ITO, graphene, silicon, or indium oxide-tin oxide containing silicon oxide, regardless of the size of the work function. can do. These conductive materials can be formed into films using a sputtering method, an inkjet method, a spin coating method, or the like.

(insulating layer)
Since organic EL elements apply electric fields to ultra-thin films, pixel defects are likely to occur due to leakage or short circuits. In order to prevent this, an insulating layer made of an insulating thin film layer may be inserted between the 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, and silicon oxide. , germanium oxide, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, and the like. Note that a mixture or a laminate of these may also be used.

(Space layer)
The above-mentioned space layer is, for example, a layer that emits fluorescent light in order to prevent excitons generated in the phosphorescent layer from diffusing into the fluorescent layer or to adjust the carrier balance when a fluorescent layer and a phosphorescent layer are stacked. This layer is provided between the phosphorescent layer and the phosphorescent layer. Moreover, a space layer can also be provided between a plurality of phosphorescence-emitting layers. Note that the term "carrier" used herein means a charge carrier in a substance.
Since the space layer is provided between the light-emitting layers, it is preferably made of a material that has both electron-transporting properties and hole-transporting properties. Further, in order to prevent triplet energy from diffusing in adjacent phosphorescent emitting layers, it is preferable that the triplet energy is 2.6 eV or more. Examples of the material used for the space 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 (directly in contact with) 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 into surrounding layers and confining the excitons within the light emitting layer.

(Layer formation method)
Each layer of the organic EL element can be formed by a conventionally known vapor deposition method, coating method, or the like. For example, vapor deposition methods such as vacuum evaporation method and molecular beam evaporation method (MBE method); dry film forming methods such as sputtering method, plasma method, and ion plating method; dipping method using a solution of a compound forming a layer; It can be formed by a known method such as a wet film forming method such as a spin coating method, a casting method, a flow coating method, a bar coating method, a roll coating method, or an inkjet method.

The thickness of each layer mentioned above is not particularly limited, but from the viewpoint of preventing defects such as pinholes from easily occurring, it is preferably 5 nm or more, and from the viewpoint of easily suppressing the increase in drive voltage, it is preferably 10 nm or less. It is preferable that there be. From this point of view, the thickness is preferably 5 nm to 10 μm, more preferably 10 nm to 0.2 μm. Note that the thickness of the emission band is as described above.

In the organic EL element having a two-layered or three-layered hole transport layer of the present invention, 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 more. Hereinafter, it is more preferably 40 nm or more and 130 nm or less.
Further, in one embodiment of the present invention, the thickness of the second hole transport layer having a two-layer structure or a three-layer structure is preferably 5 nm or more, more preferably 20 nm or more, even more preferably 25 nm or more, and particularly preferably 35 nm or more. and preferably 100 nm or less.
Further, in one embodiment of the present invention, the thickness of the hole transport layer adjacent to (directly in contact with) 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. It is also preferably 100 nm or less.
Further, in the organic EL element having a hole transport layer having a two-layer structure or a three-layer structure according to the present invention, the ratio of the film thickness D2 of the second hole transport layer to the film thickness D1 of the first hole transport layer is preferably 0.3<D2/D1<4.0, more preferably 0.5<D2/D1<3.5, still more preferably 0.75<D2/D1<3.0.

Preferred embodiments of the organic EL device of the present invention include, for example,
(1) Organic EL device having a two-layered hole transport layer - A first embodiment in which the first hole transport layer contains compound A and the second hole transport layer contains compound B;
-Both the first hole transport layer and the second hole transport layer contain compound A and compound B (however, the first hole transport layer contains more compound A, and the second hole transport layer contains compound A and compound B). A second embodiment containing more B;
- A third embodiment in which the first hole transport layer contains compound A and compound B (but contains more compound A) and the second hole transport layer contains compound B;
- A fourth embodiment in which the first hole transport layer contains compound A and the second hole transport layer contains compound A and compound B (however, it contains more compound B);
(2) Organic EL device having a three-layer hole transport layer - The first hole transport layer contains compound A, the second hole transport layer contains compound B, and the third hole transport layer contains compound A. and a fourth embodiment free of compound B;
- A fifth embodiment in which the first hole transport layer does not contain compound A and compound B, the second hole transport layer contains compound A, and the third hole transport layer contains compound B;
- A sixth embodiment in which the first hole transport layer contains compound A, the second hole transport layer does not contain compound A and compound B, and the third hole transport layer contains compound B;
- The first hole transport layer contains compound A and compound B (but contains more compound A), the second hole transport layer contains compound B, and the third hole transport layer contains compound A and compound B. A seventh embodiment that does not contain B;
- The first hole transport layer contains compound A, the second hole transport layer contains compound A and compound B (but contains more compound B), and the third hole transport layer contains compound A and compound B. An eighth embodiment that does not contain compound B;
- The first hole transport layer contains compound A and compound B (but contains more compound A), and the second hole transport layer contains compound A and compound B (however, contains more compound B) ), a ninth embodiment in which the third hole transport layer does not contain compound A and compound B;
- The first hole transport layer contains compound A and compound B (but contains more compound A), the second hole transport layer does not contain compound A and compound B, and the third hole transport layer contains compound A and compound B. A tenth embodiment comprising compound B;
- The first hole transport layer contains compound A, the second hole transport layer does not contain compound A and compound B, and the third hole transport layer contains compound A and compound B (however, compound B is 11th embodiment;
- The first hole transport layer contains compound A and compound B (but contains more compound A), the second hole transport layer does not contain compound A and compound B, and the third hole transport layer contains compound A and compound B. A twelfth embodiment comprising Compound A and Compound B (but containing more Compound B);
- The first hole transport layer does not contain compound A and compound B, the second hole transport layer contains compound A and compound B (however, it contains more compound A), and the third hole transport layer contains compound A and compound B. A thirteenth embodiment comprising compound B;
- The first hole transport layer does not contain compound A and compound B, the second hole transport layer contains compound A, and the third hole transport layer contains compound A and compound B (however, compound B is not included). 14th embodiment;
- The first hole transport layer does not contain compound A and compound B, the second hole transport layer contains compound A and compound B (however, it contains more compound A), and the third hole transport layer contains compound A and compound B. A fifteenth embodiment comprising Compound A and Compound B (but containing more Compound B);

[Electronics]
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 the light emitting device include lighting, vehicle lamps, and the like.

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

Hereinafter, the present invention will be explained in more detail using examples, but the present invention is not limited to the following examples.

Compound Inv-1 used as compound A in the production of organic EL devices of Examples 1 and 3 to 6

Compound Inv-2 used as compound A in the production of organic EL devices in Examples 2 and 7

Compound Ref-1 used for manufacturing organic EL devices of Comparative Examples 1 and 2

Compounds HTM-1 to HTM-3 used in the production of organic EL devices of Examples 3 to 7 and Comparative Example 2

Compounds HTM-4 to HTM-6 used as compound B in producing organic EL devices of Examples 1 to 7 and Comparative Examples 1 and 2

Other compounds used in manufacturing the organic EL devices of Examples 1 to 7 and Comparative Examples 1 and 2

Fabrication Example 1 of organic EL device
A 25 mm x 75 mm x 1.1 mm glass substrate with an ITO transparent electrode (anode) (manufactured by Geomatec Co., Ltd.) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.
The cleaned glass substrate with an ITO transparent electrode was mounted on a substrate holder of a vacuum evaporation apparatus, and the compound Inv-1 as compound HT-1 and the compound were first covered with the transparent electrode on the surface on which the transparent electrode was formed. HA was co-evaporated to form a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-1 and compound HA (compound HT-1:HA) was 95:5.
Next, compound Inv-1 as compound HT-1 was deposited on the hole injection layer to form a first hole transport layer (hole transport layer containing compound A) with a thickness of 70 nm.
Next, HTM-4 as compound HT-2 was deposited on this first hole transport layer (hole transport layer containing compound A), and a second hole transport layer (hole transport layer containing compound B) was deposited to have a thickness of 15 nm. transport layer) was formed.
Next, compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated onto this second hole transport layer (hole transport layer containing compound B), and a light emitting layer with a thickness of 20 nm was formed. was formed. The mass ratio of compound BH-1 and compound BD-1 (BH-1:BD-1) was 98:2.
Next, compound ET-1 was deposited on this light emitting layer to form an electron transport layer with a thickness of 10 nm.
Next, on this electron transport layer, compound ET-3 and Li were co-deposited to form an electron injection electrode with a thickness of 20 nm. The mass ratio of compound ET-3 and Li (ET-3:Li) was 96:4.
Then, metal Al was deposited on this electron injection electrode to form a metal cathode with a thickness of 80 nm.
The layer structure of the organic EL device thus obtained is shown below.
ITO(130)/HT-1:HA=95:5(10)/HT-1(70)/HT-2(15)/BH-1:BD-1=98:2(20)/ET-1 (10)/ET-3:Li=96:4(20)/Al(80)
In the above layer structure, the numbers in parentheses are film thicknesses (nm), and the ratios are mass ratios.

Example 2
An organic EL device was produced in the same manner as in Example 1, except that Compound Inv-2 was used as Compound HT-1 instead of Compound Inv-1.

Comparative example 1
An organic EL device was produced in the same manner as in Example 1, except that Compound Ref-1 was used as Compound HT-1 instead of Compound Inv-1.

Example 3
A glass substrate (manufactured by Geomatec Co., Ltd.) with a 25 mm x 75 mm x 1.1 mm ITO transparent electrode (anode) was ultrasonically cleaned in isopropyl alcohol for 5 minutes and then UV ozone cleaned for 30 minutes. The ITO film thickness was 130 nm.
The cleaned glass substrate with an ITO transparent electrode was mounted on a substrate holder of a vacuum evaporation apparatus, and the compound Inv-1 as compound HT-3 and the compound were first covered with the transparent electrode on the surface on which the transparent electrode was formed. HA was co-evaporated to form a hole injection layer with a thickness of 10 nm. The mass ratio of compound HT-3 and compound HA (compound HT-3:HA) was 95:5.
Next, compound Inv-1 as compound HT-3 was deposited on the hole injection layer to form a first hole transport layer (hole transport layer containing compound A) with a thickness of 37.5 nm.
Next, compound HTM-1 as compound HT-4 was deposited on the first hole transport layer (hole transport layer containing compound A), and a second hole transport layer (hole transport layer containing compound B) with a thickness of 37.5 nm was deposited. When there are multiple layers containing compound B, the layer closest to the light-emitting layer is the compound B-containing hole transport layer, so the second hole transport layer is not a compound B-containing hole transport layer. did.
Next, compound HTM-4 as compound HT-5 was vapor-deposited on this second hole transport layer to form a third hole transport layer (hole transport layer containing compound B) with a thickness of 15 nm. On this third hole transport layer (hole transport layer containing compound B), compound BH-1 (host material) and compound BD-1 (dopant material) were co-evaporated to form a light emitting layer with a thickness of 20 nm. did. The mass ratio of compound BH-1 and compound BD-1 (BH-1:BD-1) was 98:2.
Next, compound ET-2 was deposited on this light emitting layer to form an electron transport layer with a thickness of 10 nm.
Next, on this electron transport layer, compound ET-3 and Li were co-deposited to form an electron injection electrode with a thickness of 20 nm. The mass ratio of compound ET-3 and Li (ET-3:Li) was 96:4.
Then, metal Al was deposited on this electron injection electrode to form a metal cathode with a thickness of 80 nm.
The layer structure of the organic EL device thus obtained is shown below.
ITO(130)/HT-3:HA=95:5(10)/HT-3(37.5)/HT-4(37.5)/HT-5(15)/BH-1:BD-1=98:2 (20)/ET-2(10)/ET-3:Li=96:4(20)/Al(80)
In the above layer structure, the numbers in parentheses are film thicknesses (nm), and the ratios are mass ratios.

Example 4
In the same manner as in Example 3, except that compound HTM-2 was used as compound HT-4 instead of compound HTM-1, and compound HTM-5 was used as compound HT-5 instead of compound HTM-4. An organic EL device was produced.

Example 5
An organic EL device was produced in the same manner as in Example 3, except that compound HTM-3 was used as compound HT-4 instead of compound HTM-1.

Example 6
The same procedure as in Example 3 was carried out, except that compound HTM-3 was used as compound HT-4 instead of compound HTM-1, and compound HTM-6 was used as compound HT-5 instead of compound HTM-4. An organic EL device was produced.

Example 7
An organic EL device was produced in the same manner as in Example 4, except that Compound Inv-2 was used as Compound HT-3 instead of Compound Inv-1.

Comparative example 2
An organic EL device was produced in the same manner as in Example 4, except that compound Ref-1 was used as compound HT-3 instead of compound Inv-1.

Evaluation of Organic EL Device (1) Measurement of External Quantum Efficiency (EQE) The obtained organic EL device was driven at constant DC current at room temperature at a current density of 10 mA/cm ² . Luminance was measured using a luminance meter (Spectroluminance radiometer CS-1000 manufactured by Minolta), and the external quantum efficiency (%) was determined from the results. The results are shown in Tables 1 and 2.

As is clear from the results in Table 1, the organic EL devices of Examples 1 and 2 have higher external quantum efficiencies than the organic EL device of Comparative Example 1.

As is clear from the results in Table 2, the organic EL devices of Examples 3 to 7 have higher external quantum efficiencies than the organic EL device of Comparative Example 2.

Compound A (compound Inv-1 and compound Inv-2) and compound B (compound HTM-4 to compound HTM-6) synthesized in synthesis examples

Synthesis Example 1: Synthesis of compound Inv-1
Under an argon atmosphere, 2-chloro-7-iodo-9,9-diphenyl-9H-fluorene (14.36 g, 30 mmol), 4-biphenylboronic acid (5.94 g, 30 mmol), bis(triphenylphosphine) palladium ( II) A mixture of dichloride (0.632g, 0.90mmol), potassium carbonate (12.44g, 90mmol), DME (180mL), ethanol (7.21mL) and water (45mL) was stirred at 80°C for 7 hours. . The reaction solution was cooled to room temperature and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain Intermediate A as a white solid (10.91 g). The yield was 72%.
Furthermore, under an argon atmosphere, Intermediate A (10.91 g, 21.6 mmol), bis(biphenyl-4-yl)amine (6.94 g, 21.6 mmol), tris(dibenzylideneacetone)dipalladium(0) ( 0.396 g, 0.432 mmol), tri-t-butylphosphonium tetrafluoroborate (0.501 g, 1.728 mmol), sodium-t-butoxide (2.91 g, 30.2 mmol), and a mixture of xylene (144 mL). was stirred at 120°C for 5 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 15.36 g of white solid. The yield was 90%.
As a result of mass spectrometry analysis, the obtained product was found to be compound Inv-1, with a molecular weight of 790.02 and m/e=790.

Synthesis Example 2: Synthesis of compound Inv-2
Under an argon atmosphere, 2-bromo-7-iodo-9,9'-spirobi[fluorene] (15.64 g, 30 mmol), 4-biphenylboronic acid (5.94 g, 30 mmol), bis(triphenylphosphine) palladium ( II) A mixture of dichloride (0.632g, 0.90mmol), potassium carbonate (12.44g, 90mmol), DME (180mL), ethanol (7.21mL) and water (45mL) was stirred at 80°C for 8 hours. . The reaction solution was cooled to room temperature and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain Intermediate B as a white solid (11.33 g). The yield was 69%.
Further, under an argon atmosphere, Intermediate B (11.33 g, 20.62 mmol), bis(biphenyl-4-yl)amine (6.63 g, 20.62 mmol), tris(dibenzylideneacetone)dipalladium(0) ( 0.378g, 0.412mmol), tri-t-butylphosphonium tetrafluoroborate (0.479g, 1.649mmol), sodium-t-butoxide (2.77g, 28.9mmol), xylene (137mL). was stirred at 120°C for 3 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 13.49 g of white solid. The yield was 83%.
As a result of mass spectrometry analysis, the obtained compound was found to be compound Inv-2, with a molecular weight of 788.01 and m/e=788.

Synthesis Example 3: Synthesis of compound HTM-4
Compound 3v described on page 99 was synthesized in the same manner as in Example 3a (page 93) of WO 2013/120577. Specifically, under an argon atmosphere, a mixture of 4-bromo-9,9'-spirobi[9H-fluorene] (3.56 g, 9.01 mmol), bis(biphenyl-4-yl)amine (2.89 g, 9.01 mmol), tris(dibenzylideneacetone)dipalladium(0) (0.165 g, 0.180 mmol), tri-t-butylphosphonium tetrafluoroborate (0.209 g, 0.720 mmol), sodium-t-butoxide (1.212 g, 12.61 mmol), and toluene (60 mL) was stirred under heating and reflux for 3 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 2.86 g of a white solid. The yield was 50%.
Mass spectrometry revealed that the product was compound HTM-4, with an m/e of 636 for a molecular weight of 635.81.

Synthesis Example 4: Synthesis of compound HTM-5
As described in International Publication No. 2022/009999. Specifically, under an argon atmosphere, 2.25 g (7.00 mmol) of 4-(1-naphthalenyl)-N-[4-(1-naphthalenyl)phenyl]benzenamine, 2.53 g (7.70 mmol) of intermediate C , tris(dibenzylideneacetone)dipalladium(0) 0.128 g, (0.140 mmol), tri-t-butylphosphonium tetrafluoroborate 0.162 g (0.56 mmol), sodium-t-butoxide 0.942 g ( A mixture of 9.80 mmol) and 70 mL of xylene was stirred at 130°C for 2 hours. After the reaction solution was cooled to room temperature, it was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid. The yield was 61%.
As a result of mass spectrometry analysis, the obtained compound was found to be compound HTM-5, with a molecular weight of 713.88 and m/e=714.

Note that intermediates X and C were synthesized as follows.
Under an argon atmosphere, 1.25 g of naphtho[1,2-b]benzofuran-7-ol, 65 mg of N,N-dimethyl-4-aminopyridine, 1.08 mL of trifluoromethanesulfonic anhydride, and 27 mL of dichloromethane (dehydrated) were added to a flask. and cooled to 0°C. 10.6 mL of pyridine (dehydrated) was added dropwise, followed by stirring at room temperature for 2 hours. After the reaction was completed, it was deactivated with a sufficient amount of water. The solution was transferred to a separating funnel, extracted with dichloromethane, dried over anhydrous sodium sulfate, passed through a silica gel short column to remove origin impurities, concentrated the solution, and the resulting sample was vacuum-dried at room temperature for 3 hours. 1.50 g (77%) of a white solid of naphtho[1,2-b]benzofuran-7-yl trifluoromethanesulfonate (Intermediate X) was obtained.

Under argon atmosphere, Intermediate A mixture of 0.327 g (0.400 mmol) of 2M sodium carbonate aqueous solution (40.0 mmol), and 66.7 mL of DME was stirred at 80° C. for 2 hours. The reaction solution was cooled to room temperature, water was added, and then filtered. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain 6.07 g of white solid (Intermediate C). The yield was 92%.

Synthesis Example 5: Synthesis of compound HTM-6
As described in International Publication No. 2020/241826. Specifically, 1-(4-chlorophenyl)dibenzo[b,d]furan (7.48 g, 26.8 mmol) synthesized in the same manner as described in International Publication No. 2018/164201 under an argon atmosphere. , Intermediate D (3.16 g, 12.2 mmol), Tris(dibenzylideneacetone)dipalladium(0) (0.223 g, 0.244 mmol), Tri-t-butylphosphonium tetrafluoroborate (0.283 g, A mixture of sodium t-butoxide (3.52 g, 36.6 mmol) and toluene (48.8 mL) was stirred at 100° C. for 4 hours. After the reaction solution was cooled to room temperature, silica gel (100 mL) was added and stirred. The silica gel was removed by filtration, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography and recrystallization to obtain a white solid (3.72 g). As a result of mass spectrometry analysis (m/e=744 for a molecular weight of 743.86), the obtained white solid was compound HTM-6, and the yield was 41%.

Note that Intermediate D was synthesized as follows.

Under an argon atmosphere, 1-(4-chlorophenyl)dibenzo[b,d]furan (4.18g, 15.0mmol), tris(dibenzylidene acetone) dipalladium(0) (0.275 g, 0.30 mmol), tri-t-butylphosphonium tetrafluoroborate (0.348 g, 1.20 mmol), 1.0 M toluene solution of lithium bis(trimethylsilyl)amide ( A mixture of 30 ml, 30.0 mmol) and toluene (30 mL) was stirred at 100°C for 6 hours. After the reaction solution was cooled to room temperature, 1M hydrochloric acid (30 mL) was added and stirred. The mixture was made basic by adding 1M aqueous sodium hydroxide solution, extracted with toluene, and the organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain Intermediate D (3.16 g). The yield was 81%.

1, 11, 12 Organic EL element 2 Substrate 3 Anode 4 Cathode 5 Light emitting layer 6 Hole transport zone (hole transport 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 (18)

An organic electroluminescent device comprising an anode, a cathode, and an organic layer present between the anode and the cathode,
The organic layer includes a light emitting layer and a hole transport zone existing between the anode and the light emitting layer,
The hole transport zone is present in the compound A-containing hole transport layer containing compound A represented by the following formula (1) and on the light-emitting layer side of the compound A-containing hole transport layer, and is An organic electroluminescent device comprising a compound B-containing hole transport layer represented by formula (2) and containing a compound B different from compound A represented by formula (1) below.
(In the above formula (1),
N ^* is the central nitrogen atom.
Ar ¹ and Ar ² are each independently a substituted or unsubstituted aryl group having 6 to 30 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
L ¹ to L ³ are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 18 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms; be.
Ar ³ is each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring carbon atoms, or a substituted or unsubstituted cycloalkyl group having 6 ring carbon atoms; ~30 aryl group, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms. However, at least one of Ar ³ is a substituted or unsubstituted aryl group having 6 to 30 ring atoms, or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
n is an integer from 1 to 4, and when n is 2 or more, the plurality of Ar ³ 's are the same or different.
R ⁹ and R ¹⁰ are each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 ring-forming carbon atoms, or a substituted or unsubstituted ring-forming cycloalkyl group having 3 to 30 carbon atoms; An aryl group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 30 ring atoms.
R ⁹ and R ¹⁰ may be bonded to each other to form a ring structure, or may not be bonded to each other to form a ring structure. However, when R ⁹ and R ¹⁰ do not combine with each other to form a ring, at least one of R ⁹ and R ¹⁰ is a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms.
One selected from R ¹ to R ⁴ is a single bond bonded to *1,
*R ¹ to R ⁴ that are not single bonds bonded to 1 are each independently a hydrogen atom, a halogen atom, a nitro group, a cyano group, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms. Substituted alkenyl group having 2 to 50 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 50 carbon atoms, substituted or unsubstituted cycloalkyl group having 3 to 50 ring forming carbon atoms, substituted or unsubstituted ring forming carbon Aryl group with 6 to 50 carbon atoms, substituted or unsubstituted aralkyl group with 7 to 50 carbon atoms, substituted or unsubstituted heterocyclic group with 5 to 50 ring atoms, substituted or unsubstituted heterocyclic group with 1 to 50 carbon atoms Haloalkyl group, substituted or unsubstituted haloalkoxy group having 1 to 50 carbon atoms, group represented by -Si(R ₉₀₁ )(R ₉₀₂ )(R ₉₀₃ ), group represented by -O-(R ₉₀₄ ) , or a group represented by -S-(R ₉₀₅ ),
R ₉₀₁ to R ₉₀₅ are each independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms, or a substituted or unsubstituted cycloalkyl group having 3 to 50 ring carbon atoms; an 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 _901s exist, the two or more R _901s are the same or different,
When two or more R _902s exist, the two or more R _902s are the same or different,
When two or more R _903s exist, the two or more R _903s are the same or different,
When two or more R _904s exist, the two or more R _904s are the same or different,
When two or more R _905s exist, the two or more R _905s are the same or different.
However, two adjacent ones selected from R ¹ to R ⁴ that are not single bonds bonded to *1 may bond to each other to form a substituted or unsubstituted benzene ring, and do not bond to each other, thus forming a ring. It does not need to be formed.
n selected from R ⁵ to R ⁸ are single bonds bonded to *2,
*R ⁵ to R ⁸ that are not single bonds bonded to *2 are each independently hydrogen atoms. )
(In the above formula (2),
N ^* is the central nitrogen atom.
L ^A1 , L ^A2 and L ^A3 are each independently a single bond, a substituted or unsubstituted arylene group having 6 to 50 ring atoms, or a substituted or unsubstituted arylene group having 5 to 50 ring atoms; is a valent heterocyclic group.
Ar ¹¹¹ , Ar ¹¹² and Ar ¹¹³ are each independently a substituted or unsubstituted aryl group having 6 to 50 ring atoms, a substituted or unsubstituted heterocyclic group having 5 to 50 ring atoms, or -Si(R ^C1 )(R ^C2 )(R ^C3 ).
R ^C1 , R ^C2 and R ^C3 are each independently a substituted or unsubstituted aryl group having 6 to 50 ring carbon atoms,
When there are multiple R ^C1s , the multiple R ^C1s are the same or different from each other,
When a plurality of R ^C2s exist, the plurality of R ^C2s are the same or different from each other,
When a plurality of R ^C3s exist, the plurality of R ^C3s are the same or different from each other. ) The organic electroluminescent device according to claim 1, wherein L ¹ to L ³ are each independently a single bond or a substituted or unsubstituted phenylene group. Ar ³ is each independently a substituted or unsubstituted alkyl group having 10 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 10 to 30 ring carbon atoms, or a substituted or unsubstituted cycloalkyl group having 10 to 30 ring carbon atoms; ~30 aryl group, or a substituted or unsubstituted heterocyclic group having 10 to 30 ring atoms,
Claim 1 or 2, wherein at least one of Ar ³ is a substituted or unsubstituted aryl group having 10 to 30 ring atoms, or a substituted or unsubstituted heterocyclic group having 10 to 30 ring atoms. The organic electroluminescent device described in . The organic electroluminescent device according to any one of claims 1 to 3, wherein R ⁷ is a single bond bonded to *2. Ar ¹ and Ar ² are each independently represented by the following formula (2A), the following formula (2B), the following formula (2C), the following formula (2D), the following formula (2E), or the following formula (2F). The organic electroluminescent device according to any one of claims 1 to 4.
(In formula (2A),
*21 is the bonding position to L ¹ or L ² .
One selected from R ¹⁰¹ to R ¹⁰⁵ is a single bond bonded to *22, and one selected from R ¹⁰⁶ to R ¹¹⁰ is a single bond bonded to *23.
R ¹⁰¹ to R ¹⁰⁵ and R ¹⁰⁶ to R ¹¹⁰ , which are not single bonds, are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted ring having 6 to 12 carbon atoms. is an aryl group.
Two adjacent ones selected from R ¹⁰¹ to R ¹⁰⁵ that are not single bonds do not bond to each other and do not form a ring.
Two adjacent ones selected from R ¹⁰⁶ to R ¹¹⁰ that are not single bonds do not bond to each other and do not form a ring.
R ¹¹¹ to R ¹¹⁵ 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 aryl group having 6 to 12 ring carbon atoms; It is a substituted heterocyclic group having 5 to 13 ring atoms.
Two adjacent ones selected from R ¹¹¹ to R ¹¹⁵ do not bond to each other and do not form a ring.
m is 0, 1 or 2, and n is 0 or 1. Except when m is 2 and n is 0.
When m=0 and n=0, *23 represents *21.
When m=0 and n=1, *22 represents *21.
When m=1 and n=0, *23 represents *22. )
(In formula (2B),
*24 is the bonding position to L ¹ or L ² .
One selected from R ¹²¹ to R ¹²⁸ is a single bond bonded to *25.
R ¹²¹ to R ¹²⁸ which 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 having 6 to 12 ring carbon atoms. It is the basis.
Two adjacent ones selected from R ¹²¹ to R ¹²⁸ that are not single bonds do not bond to each other and do not form a ring. )
(In formula (2C),
*26 is the bonding position to L ¹ or L ² .
One selected from R ¹³¹ to R ¹⁴⁰ is a single bond bonded to *27.
R ¹³¹ to R ¹⁴⁰ which 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 having 6 to 12 ring carbon atoms. It is the basis.
Two adjacent ones selected from R ¹³¹ to R ¹⁴⁰ that are not single bonds do not bond to each other and do not form a ring. )
(In formula (2D),
*28 is the bonding position to L ¹ or L ² .
X ¹¹ is an oxygen atom, a sulfur atom, CR ^a R ^b , or NR ^c .
R ^a and R ^b are each independently 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 30 ring carbon atoms, and are bonded to each other. may be used to form a substituted or unsubstituted ring structure, or may not be bonded to each other and therefore do not form a ring structure.
R ^c is 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 30 ring carbon atoms.
n is 0 or 1.
^When n is 0, one selected ^from R ^a , R ^b , R ^c , and R ¹⁴¹ to R ¹⁴⁸ is a single bond bonded to *29, or a substitution or An unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted ring structure that can be formed by bonding R ^a or R ^b to each other, or a substituted or unsubstituted ring-forming carbon that can be represented by R ^c Six to thirty aryl groups may be bonded to *29 via a single bond.
When n is 1, one of R ¹⁴¹ and R ¹⁴² , R ¹⁴² and R ¹⁴³ , or R ¹⁴³ and R ¹⁴⁴ is a single bond bonded to *a, and the other is a single bond bonded to *b, and *a and *One selected from R ¹⁴¹ to R ¹⁴⁴ , R ¹⁴⁵ to R ¹⁴⁸ , R ^a , R ^b , R ^c , and R ²⁰⁰ to R ²⁰³ that is not a single bond bonded to *b is a single bond bonded to *29. or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms that R ^a or R ^b may represent; a substituted or unsubstituted ring structure that R ^a or R ^b may form by bonding with each other; Alternatively, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms that R ^c may represent may be bonded to *29 via a single bond.
The above non-single bonds R ¹⁴¹ to R ¹⁴⁸ and the above non-single bonds R ²⁰⁰ to R ²⁰³ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. An aryl group having 6 to 12 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
Two adjacent ones selected from R ¹⁴¹ to R ¹⁴⁸ , which are not single bonds, and R ²⁰⁰ to R ²⁰³ , which are not single bonds, do not bond to each other and do not form a ring. )
(In formula (2E),
*30 is the bonding position to L ¹ or L ² .
One selected from R ¹⁵¹ to R ¹⁵⁵ is a single bond bonded to *31, and the other selected from R ¹⁵¹ to R ¹⁵⁵ is a single bond bonded to *32.
Each of R ¹⁵¹ to R ¹⁵⁵ that is not a single bond is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group.
Two adjacent ones selected from R ¹⁵¹ to R ¹⁵⁵ that are not single bonds do not bond to each other and do not form a ring.
R ¹⁶¹ to R ¹⁶⁵ and R ¹⁷¹ to R ¹⁷⁵ each independently represent a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms.
At least two adjacent atoms selected from R ¹⁶¹ to R ¹⁶⁵ that are not hydrogen atoms may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form a ring. You don't have to.
At least two adjacent atoms selected from R ¹⁷¹ to R ¹⁷⁵ that are not hydrogen atoms may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore form a ring. does not have to be formed. )
(In formula (2F),
*32 is the bonding position to L ¹ or L ² .
One selected from R ¹⁸¹ to R ¹⁹² is a single bond bonded to *33.
R ¹⁸¹ to R ¹⁹² which 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 having 6 to 12 ring carbon atoms. It is the basis.
Two adjacent ones selected from R ¹⁸¹ to R ¹⁹² that are not single bonds do not bond to each other and do not form a ring. )] The organic electroluminescent device according to any one of claims 1 to 5, wherein L ^A1 , L ^A2 and L ^A3 are each independently a single bond or a substituted or unsubstituted phenylene group. Ar ¹¹¹ to Ar ¹¹³ are each independently represented by the following formula (2A), the following formula (2B), the following formula (2C), the following formula (2D), the following formula (2E), or the following formula (2F). The organic electroluminescent device according to any one of claims 1 to 6.
(In formula (2A),
*21 is the bonding position to ^LA1 , ^LA2 , or ^LA3 .
One selected from R ¹⁰¹ to R ¹⁰⁵ is a single bond bonded to *22, and one selected from R ¹⁰⁶ to R ¹¹⁰ is a single bond bonded to *23.
R ¹⁰¹ to R ¹⁰⁵ and R ¹⁰⁶ to R ¹¹⁰ , which are not single bonds, are each independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted ring having 6 to 12 carbon atoms. is an aryl group.
Two adjacent ones selected from R ¹⁰¹ to R ¹⁰⁵ that are not single bonds do not bond to each other and do not form a ring.
Two adjacent ones selected from R ¹⁰⁶ to R ¹¹⁰ that are not single bonds do not bond to each other and do not form a ring.
R ¹¹¹ to R ¹¹⁵ 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 aryl group having 6 to 12 ring carbon atoms; It is a substituted heterocyclic group having 5 to 13 ring atoms.
Two adjacent ones selected from R ¹¹¹ to R ¹¹⁵ do not bond to each other and do not form a ring.
m is 0, 1 or 2, and n is 0 or 1. Except when m is 2 and n is 0.
When m=0 and n=0, *23 represents *21.
When m=0 and n=1, *22 represents *21.
When m=1 and n=0, *23 represents *22. )
(In formula (2B),
*24 is the bonding position to ^LA1 , ^LA2 , or ^LA3 .
One selected from R ¹²¹ to R ¹²⁸ is a single bond bonded to *25.
R ¹²¹ to R ¹²⁸ which 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 having 6 to 12 ring carbon atoms. It is the basis.
Two adjacent ones selected from R ¹²¹ to R ¹²⁸ that are not single bonds do not bond to each other and do not form a ring. )
(In formula (2C),
*26 is the bonding position to ^LA1 , ^LA2 , or ^LA3 .
One selected from R ¹³¹ to R ¹⁴⁰ is a single bond bonded to *27.
R ¹³¹ to R ¹⁴⁰ which 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 having 6 to 12 ring carbon atoms. It is the basis.
Two adjacent ones selected from R ¹³¹ to R ¹⁴⁰ that are not single bonds do not bond to each other and do not form a ring. )
(In formula (2D),
*28 is the bonding position to ^LA1 , ^LA2 , or ^LA3 .
X ¹¹ is an oxygen atom, a sulfur atom, CR ^a R ^b , or NR ^c .
R ^a and R ^b are each independently 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 30 ring carbon atoms, and are bonded to each other. may be used to form a substituted or unsubstituted ring structure, or may not be bonded to each other and therefore do not form a ring structure.
R ^c is 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 30 ring carbon atoms.
n is 0 or 1.
^When n is 0, one selected ^from R ^a , R ^b , R ^c , and R ¹⁴¹ to R ¹⁴⁸ is a single bond bonded to *29, or a substitution or An unsubstituted aryl group having 6 to 30 ring-forming carbon atoms, a substituted or unsubstituted ring structure that can be formed by bonding R ^a or R ^b to each other, or a substituted or unsubstituted ring-forming carbon that can be represented by R ^c Six to thirty aryl groups may be bonded to *29 via a single bond.
When n is 1, one of R ¹⁴¹ and R ¹⁴² , R ¹⁴² and R ¹⁴³ , or R ¹⁴³ and R ¹⁴⁴ is a single bond bonded to *a, and the other is a single bond bonded to *b, and *a and *One selected from R ¹⁴¹ to R ¹⁴⁴ , R ¹⁴⁵ to R ¹⁴⁸ , R ^a , R ^b , R ^c , and R ²⁰⁰ to R ²⁰³ that is not a single bond bonded to *b is a single bond bonded to *29. or a substituted or unsubstituted aryl group having 6 to 30 ring-forming carbon atoms that R ^a or R ^b may represent; a substituted or unsubstituted ring structure that R ^a or R ^b may form by bonding with each other; Alternatively, a substituted or unsubstituted aryl group having 6 to 30 ring carbon atoms that R ^c may represent may be bonded to *29 via a single bond.
The above non-single bonds R ¹⁴¹ to R ¹⁴⁸ and the above non-single bonds R ²⁰⁰ to R ²⁰³ each independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms. An aryl group having 6 to 12 ring carbon atoms or a substituted or unsubstituted heterocyclic group having 5 to 13 ring atoms.
Two adjacent ones selected from R ¹⁴¹ to R ¹⁴⁸ , which are not single bonds, and R ²⁰⁰ to R ²⁰³ , which are not single bonds, do not bond to each other and do not form a ring. )
(In formula (2E),
*30 is the bonding position to ^LA1 , ^LA2 , or ^LA3 .
One selected from R ¹⁵¹ to R ¹⁵⁵ is a single bond bonded to *31, and the other selected from R ¹⁵¹ to R ¹⁵⁵ is a single bond bonded to *32.
Each of R ¹⁵¹ to R ¹⁵⁵ that is not a single bond is independently a hydrogen atom, an unsubstituted alkyl group having 1 to 10 carbon atoms, or an unsubstituted phenyl group.
Two adjacent ones selected from R ¹⁵¹ to R ¹⁵⁵ that are not single bonds do not bond to each other and do not form a ring.
R ¹⁶¹ to R ¹⁶⁵ and R ¹⁷¹ to R ¹⁷⁵ each independently represent a hydrogen atom or an unsubstituted alkyl group having 1 to 10 carbon atoms.
At least two adjacent atoms selected from R ¹⁶¹ to R ¹⁶⁵ that are not hydrogen atoms may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other to form a ring. You don't have to.
At least two adjacent atoms selected from R ¹⁷¹ to R ¹⁷⁵ that are not hydrogen atoms may be bonded to each other to form one or more unsubstituted benzene rings, or may not be bonded to each other and therefore form a ring. does not have to be formed. )
(In formula (2F),
*32 is the bonding position to ^LA1 , ^LA2 , or ^LA3 .
One selected from R ¹⁸¹ to R ¹⁹² is a single bond bonded to *33.
R ¹⁸¹ to R ¹⁹² which 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 having 6 to 12 ring carbon atoms. It is the basis.
Two adjacent ones selected from R ¹⁸¹ to R ¹⁹² that are not single bonds do not bond to each other and do not form a ring. )] The hole transport zone further includes a hole transport layer other than the compound A-containing hole transport layer and the compound B-containing hole transport layer, and the other hole transport layer is the compound A-containing hole transport layer. The organic electroluminescent device according to any one of claims 1 to 7, adjacent to a hole transport layer. The organic electroluminescent device according to claim 8, wherein the other hole transport layer is present between the compound A-containing hole transport layer and the compound B-containing hole transport layer. According to claim 8 or 9, of the two layers, the compound A-containing hole transport layer and the other hole transport layer, the second hole transport layer existing on the light emitting layer side has a refractive index of 1.85 or less. The organic electroluminescent device described above. Of the two layers, the compound A-containing hole transport layer and the other hole transport layer, the first hole transport layer located on the anode side has a refractive index that is higher than the compound A-containing hole transport layer and the other hole transport layer. The organic electroluminescent device according to any one of claims 8 to 10, which has a refractive index greater than that of the second hole transport layer that is present on the light emitting layer side of the two transport layers. Any one of claims 8 to 11, wherein of the two layers, the compound A-containing hole transport layer and the other hole transport layer, the second hole transport layer existing on the light emitting layer side has a thickness of 20 to 75 nm. 2. The organic electroluminescent device according to item 1. The organic electroluminescent device according to any one of claims 1 to 12, wherein the compound B-containing hole transport layer is a layer adjacent to the light emitting layer. The organic electroluminescent device according to any one of claims 1 to 13, wherein the light emitting layer is a single layer. The organic electroluminescent device according to any one of claims 1 to 14, wherein the light-emitting layer contains a light-emitting compound that emits fluorescence with a main peak wavelength of 500 nm or less. The organic electroluminescent device according to any one of claims 1 to 15, wherein the light emitting layer contains an anthracene compound as a host material. The organic electroluminescent device according to any one of claims 1 to 16, wherein the light emitting layer contains a fluorescent dopant material. An electronic device comprising the organic electroluminescent device according to any one of claims 1 to 17.