WO2023013615A1

WO2023013615A1 - Amine compound, hole injection layer and organic electroluminescent element

Info

Publication number: WO2023013615A1
Application number: PCT/JP2022/029569
Authority: WO
Inventors: 平野雅也; 野村真太朗; 松本直樹
Original assignee: 東ソー株式会社
Priority date: 2021-08-02
Filing date: 2022-08-01
Publication date: 2023-02-09

Abstract

The present invention provides: an amine compound which suppresses a transverse current of an organic electroluminescent element; a hole injection layer which uses this amine compound; and an organic electroluminescent element which has excellent drive voltage, excellent luminous efficiency and excellent durability, while being suppressed in the transverse current.　The present invention uses an amine compound that is represented by one of formula (1) to formula (3).

Description

Amine compounds, hole injection layers, and organic electroluminescent devices

The present disclosure relates to amine compounds for organic EL devices, hole injection layers, and organic electroluminescence devices.

An organic electroluminescence element is a surface-emitting element in which an organic thin film is sandwiched between a pair of electrodes. It has characteristics such as thinness and light weight, wide viewing angle, and high-speed response, and is applied to various display elements. An organic EL element is an element that utilizes light emitted when holes injected from the anode and electrons injected from the cathode recombine in the light-emitting layer. It is a multilayer lamination type in which an injection layer, a hole transport layer, a light emitting layer, and an electron transport layer are laminated.

In the hole injection layer, an electron-donating amine compound is doped with an electron-accepting p-dopant. By doping the amine compound with a p-dopant, holes are generated, and the amount of holes injected into the organic electroluminescence device can be increased, thereby reducing the driving voltage of the device. Normally, when an electric field is applied to an organic electroluminescence device, holes move perpendicularly from the anode to the cathode along the direction of the electric field. Since the holes are free to move, a "lateral current" in which the holes move horizontally with respect to the anode film may be partially generated. Generally, in an organic electroluminescence display, a hole injection layer and a hole transport layer are commonly used for a plurality of pixels. Therefore, when a lateral current as described above is generated, an unintended pixel emits light, Image quality deteriorates.

In an organic electroluminescence display in which a common hole injection layer and hole transport layer are applied to a plurality of pixels, a lateral current is generated in the conventional hole injection layer and hole transport layer, and the image quality of the organic electroluminescence display is deteriorated. There was a problem that the

Accordingly, one aspect of the present disclosure is an amine compound that suppresses lateral current in an electroluminescence element in which a hole injection layer is doped with a p-dopant, a hole transport layer and a hole injection layer using these, and a low lateral current It is directed to providing an organic electroluminescence device.

The present invention relates to the following [1] to [13].
[1]
Amine compounds represented by formulas (1) to (3):

In formulas (1) to (3),
R ¹ to R ⁴ are each independently;
hydrogen atom, deuterium atom, cyano group, linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, linear, branched or cyclic alkoxy group having 1 to 18 carbon atoms, optionally substituted carbon number 6 to 25 monocyclic, linked or condensed aromatic hydrocarbon groups, or
It is an optionally substituted monocyclic, linked or condensed heteroaromatic group having 3 to 25 carbon atoms.

^R5 and ^R6 are hydrogen.

L ¹ to L ⁵ are each independently;
one substituent selected from the group consisting of a linear, branched, or cyclic alkyl group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, a deuterium atom, and a cyano group; a monocyclic, linked or condensed divalent aromatic hydrocarbon group having 6 to 25 carbon atoms which may have more than
an optionally substituted monocyclic, linked or condensed divalent heteroaromatic group having 3 to 25 carbon atoms, or
It is a single bond.

^L6 represents a single bond.

X ¹ and X ² are each independently;
one substituent selected from the group consisting of a linear, branched, or cyclic alkyl group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, a deuterium atom, and a cyano group; A monocyclic, linked, or condensed divalent aromatic hydrocarbon group having 6 to 25 carbon atoms which may have more than, or
an optionally substituted monocyclic, linked or condensed divalent heteroaromatic group having 3 to 25 carbon atoms;
^X3 is a single bond.

B represents either group represented by the following chemical formula (4) or (5).

In formulas (1) to (5),
Ar ² , Ar ³ and Ar ⁵ to Ar ¹⁰ are each independently;
linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, linear, branched or cyclic alkoxy group having 1 to 18 carbon atoms, deuterium atom, cyano group, phenyl group, biphenylyl group, naphthyl group, phenanthryl group , a monocyclic ring having 6 to 25 carbon atoms optionally having one or more substituents selected from the group consisting of a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group, linked, or a condensed aromatic hydrocarbon group, or a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 18 carbon atoms, a deuterium atom, a cyano group, It may have one or more substituents selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group. It represents a monocyclic, linked or condensed heteroaromatic group having 3 to 25 carbon atoms.

Ar ¹ and Ar ⁴ are each independently one selected from groups represented by the following general formulas (6) to (14),
When B in formula (3) is represented by formula (4), at least one of Ar ⁷ , Ar ⁸ and Ar ⁹ is each independently represented by general formulas (6) to (16) above. is one selected from the groups
When B in formula (3) is represented by formula (5), at least one of Ar ⁷ , Ar ⁸ and Ar ¹⁰ is each independently represented by general formulas (6) to (16) above. is one selected from the groups

In formulas (6) to (16),
R ⁷ is;
a hydrogen atom, a deuterium atom, a cyano group, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, or a linear, branched or cyclic alkoxy group having 1 to 18 carbon atoms;
Ar ¹¹ is;
an optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 10 to 25 carbon atoms, or
an optionally substituted monocyclic, linked or condensed heteroaromatic group having 3 to 25 carbon atoms;
Ar ¹² and Ar ¹³ are each independently;
an optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 25 carbon atoms, or
an optionally substituted monocyclic, linked or condensed heteroaromatic group having 3 to 25 carbon atoms;
^L7 is;
an optionally substituted monocyclic, linked or condensed divalent aromatic hydrocarbon group having 6 to 25 carbon atoms, or
It is an optionally substituted monocyclic, linked or condensed divalent heteroaromatic group having 3 to 25 carbon atoms.

L ⁸ is;
an optionally substituted monocyclic, linked or condensed divalent aromatic hydrocarbon group having 6 to 25 carbon atoms,
an optionally substituted monocyclic, linked or condensed divalent heteroaromatic group having 3 to 25 carbon atoms, or
It is a single bond.

Y is an oxygen atom or a sulfur atom.
[2]
Ar ² , Ar ³ and Ar ⁵ to Ar ¹⁰ are each independently
(i) phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spirobifluorenyl group, benzofluorenyl group, phenanthryl group, fluoranthenyl group, triphenylenyl group, anthryl group, pyrenyl group, carbazolyl group; , a dibenzofuranyl group, or a dibenzothienyl group, or
(ii) the group represented by (i) is a methyl group, an ethyl group, a methoxy group, an ethoxy group, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylsilyl group, or a carbazolyl; The amine compound according to [1], which is a group substituted with one or more groups selected from the group consisting of a group, a dibenzothienyl group, and a dibenzofuranyl group.
[3]
L ¹ to L ⁴ are each independently
a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, or a single bond which may have one or more substituents selected from the group consisting of a methyl group, a methoxy group, a cyano group, a deuterium atom, and a phenyl group; The amine compound according to [1] or [2].
[4]
X ¹ and X ² are each independently
A phenylene group optionally having one or more substituents selected from the group consisting of a methyl group, a methoxy group, a cyano group, a deuterium atom, and a phenyl group, a biphenylene group, a terphenylene group, a naphthylene group, and a fluorene-diyl spirobifluorene-diyl group, phenanthrene-diyl group, triphenylene-diyl group, carbazole-diyl group, dibenzofuran-diyl group, or dibenzothiophene-diyl group [1] to [3]. Amine compounds.
[5]
Ar ¹¹ is
A biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluore which optionally has one or more substituents selected from the group consisting of a methyl group, a methoxy group, a cyano group, a deuterium atom, and a phenyl group The amine compound according to any one of [1] to [4], which is a nyl group, phenanthryl group, triphenylenyl group, carbazolyl group, dibenzofuranyl group, or dibenzothienyl group.
[6]
Ar ¹² and Ar ¹³ are each independently
A phenyl group optionally having one or more substituents selected from the group consisting of a methyl group, a methoxy group, a cyano group, a deuterium atom, and a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spiro The amine compound according to any one of [1] to [5], which is a bifluorenyl group, phenanthryl group, triphenylenyl group, carbazolyl group, dibenzofuranyl group, or dibenzothienyl group.
[7]
In formula (3), B is represented by formula (4), and at least one of Ar ⁷ and Ar ⁹ is each independently selected from groups represented by general formulas (6) to (16). The amine compound according to any one of [1] to [6], which is one type.
[8]
In formula (3), B is represented by formula (5), and at least one of Ar ⁷ and Ar ¹⁰ is each independently selected from groups represented by general formulas (6) to (16). The amine compound according to any one of [1] to [7], which is one type.
[9]
In formula (3), B is represented by formula (5), and both Ar ⁷ and Ar ¹⁰ are each independently selected from the groups represented by the general formulas (6) to (16) The amine compound according to any one of [1] to [8], which is one type.
[10]
A hole injection layer containing two types of compounds, wherein the first compound is the amine compound according to any one of [1] to [9], and the second compound is an electron acceptor. A hole injection layer that is a p-dopant.
[11]
An organic electroluminescence device having at least an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer and a cathode, wherein the hole injection layer comprises at least [1] to [9]. An organic electroluminescence device comprising the amine compound according to any one of claims 1 to 3.
[12]
An organic electroluminescence device having at least an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer and a cathode, wherein both the hole injection layer and the hole transport layer have An organic electroluminescence device comprising the amine compound according to any one of [1] to [9].
[13]
An organic electroluminescence device having at least an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer and a cathode, wherein at least one layer is any one of [1] to [9]. 10. An organic electroluminescence device comprising the amine compound according to claim 1.

It is an organic electroluminescent device containing the compound of the present invention.

Hereinafter, the amine compound according to one aspect of the present disclosure, the hole transport layer and the hole injection layer using these, and the organic electroluminescence device with little lateral current will be described in detail.
[Amine compound]
Amine compounds according to one aspect of the present disclosure are represented by formulas (1) to (3).

^R5 and ^R6 are hydrogen.

L ¹ to L ⁶ are each independently;
one substituent selected from the group consisting of a linear, branched, or cyclic alkyl group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, a deuterium atom, and a cyano group; a monocyclic, linked or condensed divalent aromatic hydrocarbon group having 6 to 25 carbon atoms which may have more than
an optionally substituted monocyclic, linked or condensed divalent heteroaromatic group having 3 to 25 carbon atoms, or
It is a single bond.

^L6 represents a single bond.

X ¹ and X ² are each independently;
an optionally substituted monocyclic, linked or condensed divalent aromatic hydrocarbon group having 6 to 25 carbon atoms,
It is an optionally substituted monocyclic, linked or condensed divalent heteroaromatic group having 3 to 25 carbon atoms.

^X3 is a single bond.

In formulas (6) to (16),
R ⁷ is;
A hydrogen atom, a deuterium atom, a cyano group, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, or a linear, branched or cyclic alkoxy group having 1 to 18 carbon atoms.

Ar ¹¹ is;
an optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 10 to 25 carbon atoms, or
It is an optionally substituted monocyclic, linked or condensed heteroaromatic group having 3 to 25 carbon atoms.

Ar ¹² and Ar ¹³ are each independently;
an optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 25 carbon atoms, or
It is an optionally substituted monocyclic, linked or condensed heteroaromatic group having 3 to 25 carbon atoms.

^L7 is;
an optionally substituted monocyclic, linked or condensed divalent aromatic hydrocarbon group having 6 to 25 carbon atoms, or
It is an optionally substituted monocyclic, linked or condensed divalent heteroaromatic group having 3 to 25 carbon atoms.

　Y is an oxygen atom or a sulfur atom.

Examples of the linear, branched or cyclic alkyl groups having 1 to 18 carbon atoms described above include methyl group, propyl group, isopropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group and hexyl. group, heptyl group, octyl group, stearyl group, cyclopropyl group, cyclohexyl group, trifluoromethyl group, adamantyl group and the like.

Examples of the linear, branched or cyclic alkoxy groups having 1 to 18 carbon atoms described above include propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, A hexyloxy group, a stearyloxy group, a difluoromethoxy group, a trifluoromethoxy group and the like can be mentioned.

The monocyclic, linked or condensed aromatic hydrocarbon groups having 10 to 25 carbon atoms described above include, for example, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spirobifluorenyl group, benzofluoro orenyl group, dibenzofluorenyl group, phenanthryl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, anthryl group, tetracenyl group, chrysenyl group, perylenyl group and pentacenyl group, and benzene, naphthalene, and one or more condensed rings selected from the group consisting of phenanthrene.

Examples of the monocyclic, linked or condensed aromatic hydrocarbon groups having 6 to 25 carbon atoms described above include phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group and spirobifluorenyl group. , benzofluorenyl group, dibenzofluorenyl group, phenanthryl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, anthryl group, tetracenyl group, chrysenyl group, perylenyl group, and pentacenyl group, and benzene in these groups , naphthalene, and one or more condensed rings selected from the group consisting of phenanthrene.

Examples of the monocyclic, linked or condensed heteroaromatic groups having 3 to 25 carbon atoms described above include pyrrolyl, thienyl, furyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl, and isoxazolyl. group, pyridyl group, pyrazyl group, indolyl group, benzothienyl group, benzofuranyl group, benzimidazolyl group, indazolyl group, benzothiazolyl group, benzoisothiazolyl group, 2,1,3-benzothiadiazolyl group, benzoxazolyl group , benzoisoxazolyl, 2,1,3-benzoxadiazolyl, quinolyl, isoquinolyl, carbazolyl, dibenzothienyl, dibenzofuranyl, phenoxazinyl, phenothiazinyl, phenazinyl, and thianthrenyl groups, and these groups to which one or more selected from the group consisting of benzene, naphthalene, and phenanthrene are condensed.

The optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 10 to 25 carbon atoms described above; condensed aromatic hydrocarbon group; optionally substituted monocyclic, linked or condensed heteroaromatic group having 3 to 25 carbon atoms, each independently having 1 to 18 carbon atoms linear, branched or cyclic alkyl group, linear, branched or cyclic alkoxy group having 1 to 18 carbon atoms, deuterium atom, cyano group, phenyl group, biphenylyl group, naphthyl group, phenanthryl group, triphenylenyl group, triphenyl It is preferably substituted with one or more groups selected from the group consisting of a silyl group, a carbazolyl group, a dibenzothienyl group and a dibenzofuranyl group. At this time, the number of substituents is not particularly limited.

Specific examples of the optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 10 to 25 carbon atoms include, but are not limited to, 4-biphenyl group, 3-biphenyl group, 2-biphenyl group, 2-methyl-1,1'-biphenyl-4-yl group, 3-methyl-1,1'-biphenyl-4-yl group, 2'-methyl-1,1'-biphenyl-4 -yl group, 3'-methyl-1,1'-biphenyl-4-yl group, 4'-methyl-1,1'-biphenyl-4-yl group, 2,6-dimethyl-1,1'-biphenyl -4-yl group, 2,2'-dimethyl-1,1'-biphenyl-4-yl group, 2,3'-dimethyl-1,1'-biphenyl-4-yl group, 2,4'-dimethyl -1,1'-biphenyl-4-yl group, 3,2'-dimethyl-1,1'-biphenyl-4-yl group, 2',3'-dimethyl-1,1'-biphenyl-4-yl group, 2',4'-dimethyl-1,1'-biphenyl-4-yl group, 2',5'-dimethyl-1,1'-biphenyl-4-yl group, 2',6'-dimethyl- 1,1′-biphenyl-4-yl group, p-terphenyl-2-yl group, p-terphenyl-3-yl group, p-terphenyl-4-yl group, p-terphenyl-2′- yl group, m-terphenyl-2-yl group, m-terphenyl-3-yl group, m-terphenyl-4-yl group, m-terphenyl-2'-yl group, m-terphenyl-4 '-yl group, m-terphenyl-5'-yl group, o-terphenyl-2-yl group, o-terphenyl-3-yl group, o-terphenyl-4-yl group, o-terphenyl -3'-yl group, o-terphenyl-4'-yl group, 1-naphthyl group, 2-naphthyl group, 2-methylnaphthalen-1-yl group, 4-methylnaphthalen-1-yl group, 6- methylnaphthalen-2-yl group, 4-(1-naphthyl)phenyl group, 4-(2-naphthyl)phenyl group, 3-(1-naphthyl)phenyl group, 3-(2-naphthyl)phenyl group, 3- methyl-4-(1-naphthyl)phenyl group, 3-methyl-4-(2-naphthyl)phenyl group, 4-(1-naphthyl)biphenyl group, 4-(2-naphthyl)biphenyl group, 3-(1 -naphthyl)biphenyl group, 3-(2-naphthyl)biphenyl group, 4-(2-methylnaphthalen-1-yl)phenyl group, 3-(2-methylnaphthalen-1-yl)phenyl group, 4-phenylnaphthalene -1-yl group, 4-( 2-methylphenyl)naphthalen-1-yl group, 4-(3-methylphenyl)naphthalen-1-yl group, 4-(4-methylphenyl)naphthalen-1-yl group, 6-phenylnaphthalen-2-yl group, 4-(2-methylphenyl)naphthalen-2-yl group, 4-(3-methylphenyl)naphthalen-2-yl group, 4-(4-methylphenyl)naphthalen-2-yl group, tetraphenylsilane -4-yl group, tetraphenylsilane-3-yl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, 9,9-diphenyl-2-fluorenyl group, 9,9-diphenyl-4- fluorenyl group, 9,9'-spirobifluoren-2-yl group, 9,9'-spirobifluoren-4-yl group, 4-(9,9'-spirobifluoren-4-yl)phenyl group, 3-(9,9'-spirobifluoren-4-yl)phenyl group, 4-(9,9'-spirobifluoren-4-yl)biphenyl group, 3-(9,9'-spirobifluorene- 4-yl)biphenyl group, 4-(9,9'-diphenylfluoren-4-yl)phenyl group, 3-(9,9'-diphenylfluoren-4-yl)phenyl group, 4-(9,9' -diphenylfluoren-4-yl)biphenyl group, 3-(9,9'-diphenylfluoren-4-yl)biphenyl group, 3-(1-triphenylenyl)biphenyl group, 9-phenanthryl group, 2-phenanthryl group, 4 -(9-phenanthryl)phenyl group, 3-(9-phenanthryl)phenyl group, 4-(9-phenanthryl)biphenyl group, 3-(1-naphthyl)biphenyl group, 3-(9-phenanthryl)biphenyl group, 1 -triphenylenyl group, 2-triphenylenyl group, 3-triphenylenyl group, 4-triphenylenyl group, 4-(1-triphenylenyl)phenyl group, 3-(1-triphenylenyl)phenyl group, 4-(1-triphenylenyl)biphenyl group, 3 -(1-triphenylenyl)biphenyl group, 3-(1-triphenylenyl)biphenyl group, 11,11'-dimethylbenzo[a]fluorene-9-yl group, 11,11'-dimethylbenzo[a]fluorene-3- yl group, 11,11′-dimethylbenzo[b]fluoren-9-yl group, 11,11′-dimethylbenzo[b]fluoren-3-yl group, 11,11′-dimethylbenzo[c]fluorene-9 -yl group, 11,11′-dimethylbenzo[c ] fluoren-2-yl group, 3-fluoranthenyl group, 8-fluoranthenyl group and the like can be exemplified.

Specific examples of the optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 25 carbon atoms are not particularly limited, but the number of carbon atoms which may be substituted is not particularly limited. In addition to the groups exemplified as 6 to 25 monocyclic, linked or condensed aromatic hydrocarbon groups, a phenyl group, a 4-methylphenyl group, a 3-methylphenyl group, a 2-methylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,6-dimethylphenyl group, 2,3,5-trimethylphenyl group, Examples include 2,3,6-trimethylphenyl group, 3,4,5-trimethylphenyl group and the like.

Specific examples of optionally substituted monocyclic, linked or condensed heteroaromatic groups having 3 to 25 carbon atoms include 1-imidazolyl group, 2-phenyl-1-imidazolyl group, 2-phenyl-3 ,4-dimethyl-1-imidazolyl group, 2,3,4-triphenyl-1-imidazolyl group, 2-(2-naphthyl)-3,4-dimethyl-1-imidazolyl group, 2-(2-naphthyl) -3,4-diphenyl-1-imidazolyl group, 1-methyl-2-imidazolyl group, 1-ethyl-2-imidazolyl group, 1-phenyl-2-imidazolyl group, 1-methyl-4-phenyl-2-imidazolyl group, 1-methyl-4,5-dimethyl-2-imidazolyl group, 1-methyl-4,5-diphenyl-2-imidazolyl group, 1-phenyl-4,5-dimethyl-2-imidazolyl group, 1-phenyl -4,5-diphenyl-2-imidazolyl group, 1-phenyl-4,5-dibiphenylyl-2-imidazolyl group, 1-methyl-3-pyrazolyl group, 1-phenyl-3-pyrazolyl group, 1-methyl-4 -pyrazolyl group, 1-phenyl-4-pyrazolyl group, 1-methyl-5-pyrazolyl group, 1-phenyl-5-pyrazolyl group, 2-thiazolyl group, 4-thiazolyl group, 5-thiazolyl group, 3-isothiazolyl group , 4-isothiazolyl group, 5-isothiazolyl group, 2-oxazolyl group, 4-oxazolyl group, 5-oxazolyl group, 3-isoxazolyl group, 4-isoxazolyl group, 5-isoxazolyl group, 2-pyridyl group, 3-methyl- 2-pyridyl group, 4-methyl-2-pyridyl group, 5-methyl-2-pyridyl group, 6-methyl-2-pyridyl group, 3-pyridyl group, 4-methyl-3-pyridyl group, 4-pyridyl group , 2-pyrimidyl group, 2,2′-bipyridin-3-yl group, 2,2′-bipyridin-4-yl group, 2,2′-bipyridin-5-yl group, 2,3′-bipyridin-3 -yl group, 2,3'-bipyridin-4-yl group, 2,3'-bipyridin-5-yl group, 5-pyrimidyl group, pyrazyl group, 1,3,5-triazyl group, 4,6-diphenyl -1,3,5-triazin-2-yl group, 1-benzimidazolyl group, 2-methyl-1-benzimidazolyl group, 2-phenyl-1-benzimidazolyl group, 1-methyl-2-benzimidazolyl group, 1-phenyl- 2-benzimidazolyl group, 1-methyl-5-benzimidazolyl group, 1,2-dimethyl-5-benzimidazolyl group, 1-methyl-2-phenyl-5-benzimidazolyl group, 1-phenyl-5-benzimidazolyl group, 1,2-diphenyl-5-benzimidazolyl group, 1-methyl-6-benzimidazolyl group, 1,2-dimethyl- 6-benzimidazolyl group, 1-methyl-2-phenyl-6-benzimidazolyl group, 1-phenyl-6-benzimidazolyl group, 1,2-diphenyl-6-benzimidazolyl group, 1-methyl-3-indazolyl group, 1-phenyl -3-indazolyl group, 2-benzothiazolyl group, 4-benzothiazolyl group, 5-benzothiazolyl group, 6-benzothiazolyl group, 7-benzothiazolyl group, 3-benzisothiazolyl group, 4-benzisothiazolyl group, 5-benzo isothiazolyl group, 6-benzisothiazolyl group, 7-benzisothiazolyl group, 2,1,3-benzothiadiazol-4-yl group, 2,1,3-benzothiadiazol-5-yl group, 2 -benzoxazolyl group, 4-benzoxazolyl group, 5-benzoxazolyl group, 6-benzoxazolyl group, 7-benzoxazolyl group, 3-benzoisoxazolyl group, 4- benzisoxazolyl group, 5-benzisoxazolyl group, 6-benzisoxazolyl group, 7-benzisoxazolyl group, 2,1,3-benzoxadiazolyl-4-yl group, 2,1,3-benzoxadiazolyl-5-yl group, 2-quinolyl group, 3-quinolyl group, 5-quinolyl group, 6-quinolyl group, 1-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group , 2-acridinyl group, 9-acridinyl group, 1,10-phenanthroline-3-yl group, 1,10-phenanthroline-5-yl group, 2-thienyl group, 3-thienyl group, 2-benzothienyl group, 3 -benzothienyl group, 2-dibenzothienyl group, 4-dibenzothienyl group, 2-furanyl group, 3-furanyl group, 2-benzofuranyl group, 3-benzofuranyl group, 2-dibenzofuranyl group, 4-dibenzofuranyl group , carbazol-9-yl group, 9-methylcarbazol-2-yl group, 9-methylcarbazol-3-yl group, 9-methylcarbazol-4-yl group, 9-phenylcarbazol-2-yl group, 9- phenylcarbazol-3-yl group, 9-phenylcarbazol-4-yl group, 9-biphenylcarbazol-2-yl group, 9-biphenylcarbazol-3-yl group, 9-biphenylcarbazole Ru-4-yl group, 2-(9-carbazolyl)phenyl group, 3-(9-carbazolyl)phenyl group, 4-(9-carbazolyl)phenyl group, 2-(9-carbazolyl)biphenyl group, 3-( 9-carbazolyl)biphenyl group, 4-(9-carbazolyl)biphenyl group, 2-(9-phenylcarbazol-3-yl)phenyl group, 3-(9-phenylcarbazol-3-yl)phenyl group, 4-( 9-phenylcarbazol-3-yl)phenyl group, 2-thiantryl group, 10-phenylphenothiazin-3-yl group, 10-phenylphenothiazin-2-yl group, 10-phenylphenoxazin-3-yl group, 10- phenylphenoxazin-2-yl group, 1-methylindol-2-yl group, 1-phenylindol-2-yl group, 1-methylindol-2-yl group, 1-phenylindol-2-yl group, 4 -(2-pyridyl)phenyl group, 4-(3-pyridyl)phenyl group, 4-(4-pyridyl)phenyl group, 3-(2-pyridyl)phenyl group, 3-(3-pyridyl)phenyl group, 3 -(4-pyridyl)phenyl group, 4-(2-phenylimidazol-1-yl)phenyl group, 4-(1-phenylimidazol-2-yl)phenyl group, 4-(2,3,4-triphenyl) imidazol-1-yl)phenyl group, 4-(1-methyl-4,5-diphenylimidazol-2-yl)phenyl group, 4-(2-methylbenzimidazol-1-yl)phenyl group, 4-(2 -phenylbenzimidazol-1-yl)phenyl group, 4-(1-methylbenzimidazol-2-yl)phenyl group, 4-(2-phenylbenzimidazol-1-yl)phenyl group, 3-(2-methyl) benzimidazol-1-yl)phenyl group, 3-(2-phenylbenzimidazol-1-yl)phenyl group, 3-(1-methylbenzimidazol-2-yl)phenyl group, 3-(2-phenylbenzimidazole -1-yl)phenyl group, 4-(3,5-diphenyltriazin-1-yl)phenyl group, 4-(2-thienyl)phenyl group, 4-(2-furanyl)phenyl group, 5-phenylthiophene- 2-yl group, 5-phenylfuran-2-yl group, 4-(5-phenylthiophen-2-yl)phenyl group, 4-(5-phenylfuran-2-yl)phenyl group, 3-(5- phenylthiophen-2-yl)phenyl group, 3-(5-phenylphenyl ran-2-yl)phenyl group, 4-(2-benzothienyl)phenyl group, 4-(3-benzothienyl)phenyl group, 3-(2-benzothienyl)phenyl group, 3-(3-benzothienyl) Phenyl group, 4-(2-dibenzothienyl) phenyl group, 4-(4-dibenzothienyl) phenyl group, 3-(2-dibenzothienyl) phenyl group, 3-(4-dibenzothienyl) phenyl group, 4-( 2-dibenzofuranyl)phenyl group, 4-(4-dibenzofuranyl)phenyl group, 3-(2-dibenzofuranyl)phenyl group, 3-(4-dibenzofuranyl)phenyl group, 4-(2- benzothienyl)phenyl group, 4-(3-benzothienyl)phenyl group, 3-(2-benzothienyl)biphenyl group, 3-(3-benzothienyl)biphenyl group, 4-(2-dibenzothienyl)biphenyl group, 4-(4-dibenzothienyl)biphenyl group, 3-(2-dibenzothienyl)biphenyl group, 3-(4-dibenzothienyl)biphenyl group, 4-(2-dibenzofuranyl)biphenyl group, 4-(4- dibenzofuranyl)biphenyl group, 3-(2-dibenzofuranyl)biphenyl group, 3-(4-dibenzofuranyl)biphenyl group, 5-phenylpyridin-2-yl group, 4-phenylpyridin-2-yl group , 5-phenylpyridin-3-yl group and the like.

Examples of the monocyclic, linked or condensed divalent aromatic hydrocarbon group having 6 to 25 carbon atoms described above include, for example, a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a fluorene-diyl group, a spiro bifluorene-diyl group, phenanthrene-diyl group, triphenylene-diyl group, pyrene-diyl group, anthracene-diyl group and the like.

Examples of the monocyclic, linked or condensed divalent heteroaromatic group having 3 to 25 carbon atoms described above include thiophene-diyl group, furan-diyl group, benzofuran-diyl group and benzothiophene-diyl group. , dibenzofuran-diyl group, dibenzothiophene-diyl group, carbazole-diyl group, pyridine-diyl group and the like.

The above-mentioned optionally substituted monocyclic, linked or condensed C6-25 monocyclic, linked or condensed divalent aromatic hydrocarbon group, optionally substituted C3-25 monocyclic, linked , or the substituents of the condensed divalent heteroaromatic group are each independently a linear, branched or cyclic alkyl group having 1 to 8 carbon atoms, a linear, branched or cyclic group having 1 to 18 carbon atoms one selected from the group consisting of an alkoxy group, a deuterium atom, a cyano group, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group; Substitution with the above groups is preferred. At this time, the number of substituents is not particularly limited.

optionally substituted monocyclic, linked or condensed divalent aromatic hydrocarbon group having 6 to 25 carbon atoms; optionally substituted monocyclic, linked or condensed ring having 3 to 25 carbon atoms Specific examples of the divalent heteroaromatic group include, but are not limited to, 1,4-phenylene group, 1,3-phenylene group, 1,2-phenylene group, 2-methyl-1,4-phenylene group, 3-methyl-1,4-phenylene group, 2-methyl-1,3-phenylene group, 4-methyl-1,3-phenylene group, 5-methyl-1,3-phenylene group, 6-methyl- 1,3-phenylene group, 4,4'-biphenylene group, 4,3'-biphenylene group, 4,2'-biphenylene group, 3,3'-biphenylene group, 3,2'-biphenylene group, 2,2 '-biphenylene group, 4,4''-p-terphenylene group, 4,3''-p-terphenylene group, 4,2''-p-terphenylene group, 3,3''-p-terphenylene group phenylene group, 3,2''-p-terphenylene group, 2,2''-p-terphenylene group, 4,2'-p-terphenylene group, 4,3'-p-terphenylene group, 3 , 2′-p-terphenylene group, 3,3′-p-terphenylene group, 2,3′-p-terphenylene group, 2,2′-p-terphenylene group, 4,4″-m -terphenylene group, 4,3''-m-terphenylene group, 4,2''-m-terphenylene group, 3,3''-m-terphenylene group, 3,2''-m-terphenylene group phenylene group, 2,2''-m-terphenylene group, 4,2'-m-terphenylene group, 4,4'-m-terphenylene group, 4,5'-m-terphenylene group, 4, 6'-m-terphenylene group, 3,2'-m-terphenylene group, 3,4'-m-terphenylene group, 3,5'-m-terphenylene group, 3,6'-m-terphenylene group phenylene group, 2,2'-m-terphenylene group, 2,4'-m-terphenylene group, 2,5'-m-terphenylene group, 2,6'-m-terphenylene group, 4,4 ''-o-terphenylene group, 4,3''-o-terphenylene group, 4,2''-o-terphenylene group, 3,3''-o-terphenylene group, 3,2'' -o-terphenylene group, 2,2''-o-terphenylene group, 4,3'-o-terphenylene group, 4,4'-o-terphenylene group, 4,5'-o-terphenylene group, 4,6'-o-terphenylene group, 3,3'-o-terphenylene group, 3,4'-o- terphenylene group, 3,5'-o-terphenylene group, 3,6'-o-terphenylene group, 2,3'-o-terphenylene group, 2,4'-o-terphenylene group, 2, 5′-o-terphenylene group, 2,6′-o-terphenylene group, 1,2-naphthylene group, 1,3-naphthylene group, 1,4-naphthylene group, 1,5-naphthylene group, 1, 6-naphthylene group, 1,7-naphthylene group, 1,8-naphthylene group, 2,3-naphthylene group, 2,4-naphthylene group, 2,5-naphthylene group, 2,6-naphthylene group, 2,7 -naphthylene group, 2,8-naphthylene group, 9,9-dimethyl-fluorene-2,7-diyl group, 9,9-dimethyl-fluorene-2,8-diyl group, 9,9-dimethyl-fluorene-2 ,4-diyl group, 9,9-dimethyl-fluorene-2,5-diyl group, 9,9-dimethyl-fluorene-2,6-diyl group, 9,9-dimethyl-fluorene-3,6-diyl group , 9,9-diphenyl-fluorene-2,7-diyl group, 9,9-diphenyl-fluorene-2,8-diyl group, 9,9-diphenyl-fluorene-2,4-diyl group, 9,9- Diphenyl-fluorene-2,5-diyl group, 9,9-diphenyl-fluorene-2,6-diyl group, 9,9-diphenyl-fluorene-3,6-diyl group, spirobifluorene-2,7-diyl spirobifluorene-2,8-diyl group, spirobifluorene-2,4-diyl group, spirobifluorene-2,5-diyl group, spirobifluorene-2,6-diyl group, spirobifluorene- 3,6-diyl group, phenanthrene-9,10-diyl group, phenanthrene-2,9-diyl group, phenanthrene-2,10-diyl group, phenanthrene-2,8-diyl group, phenanthrene-2,7-diyl phenanthrene-2,6-diyl group, phenanthrene-2,5-diyl group, phenanthrene-2,14-diyl group, phenanthrene-2,3-diyl group, phenanthrene-9,10-diyl group, phenanthrene-3 , 10-diyl group, phenanthrene-3,9-diyl group, phenanthrene-3,8-diyl group, phenanthrene-3,7-diyl group, phenanthrene-3,6-diyl group, phenanthrene-3,5-diyl group , phenanthrene-4,10-diyl group, phenanthrene-4,9-diyl group, phenanthrene-4,8-diyl group, phenanthrene-4,7-diyl group, phenanthrene-4,6-diyl group, triphenylene-1,3-diyl group, triphenylene-1,4-diyl group, triphenylene-1,5-diyl group, triphenylene-1,6-diyl group, triphenylene-1 ,7-diyl group, triphenylene-1,8-diyl group, triphenylene-2,3-diyl group, triphenylene-2,4-diyl group, triphenylene-2,5-diyl group, triphenylene-2,6-diyl group , triphenylene-2,7-diyl group, triphenylene-3,5-diyl group, triphenylene-3,6-diyl group, triphenylene-4,6-diyl group, pyrene-1,3-diyl group, pyrene-1, 6-diyl group, pyrene-1,8-diyl group, pyrene-2,7-diyl group, anthracene-2,6-diyl group, anthracene-9,10-diyl group, 9,10-diphenylanthracenediyl group, thiophene-2,5-diyl group, furan-2,5-diyl group, benzofuran-diyl group, benzothiophene-diyl group, dibenzofuran-2,8-diyl group, dibenzofuran-2,6-diyl group, dibenzofuran-3 , 7-diyl group, dibenzofuran-4,6-diyl group, dibenzothiophene-2,8-diyl group, dibenzothiophene-2,6-diyl group, dibenzothiophene-3,7-diyl group, dibenzothiophene-4, 6-diyl group, 9-phenylcarbazole-2,7-diyl group, pyridine-2,5-diyl group, pyridine-2,6-diyl group, pyridine-3,5-diyl group, pyridine-2,4- A diyl group and the like can be exemplified.

The optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 10 to 25 carbon atoms described above, or the optionally substituted monocyclic or linked ring having 3 to 25 carbon atoms. , or a condensed heteroaromatic group;
For example, phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spirobifluorenyl group, benzofluorenyl group, dibenzofluorenyl group, phenanthryl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, Anthryl group, tetracenyl group, chrysenyl group, perylenyl group and pentacenyl group, and those groups to which one or more selected from the group consisting of benzene, naphthalene and phenanthrene are condensed.

In the amine compounds represented by general formulas (1) to (3),
Since R ¹ to R ⁴ have high hole transport properties and can reduce the driving voltage, each independently
A methyl group, a phenyl group, a methylphenyl group or a hydrogen atom is preferred.

Since ^R7 has a high hole-transport property and can reduce the driving voltage, each independently
A methyl group or a hydrogen atom is preferred.

Since L ¹ to L ⁵ have high hole transport properties and can reduce the driving voltage, each independently
a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, or a single bond which may have one or more substituents selected from the group consisting of a methyl group, a methoxy group, a cyano group, a deuterium atom and a phenyl group; Preferably.

Since L ⁷ and L ⁸ have high hole transport properties and can reduce the driving voltage, each independently
a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, or a single bond which may have one or more substituents selected from the group consisting of a methyl group, a methoxy group, a cyano group, a deuterium atom and a phenyl group; Preferably.

Since X ¹ and X ² have high hole-transport properties, the drive voltage can be reduced, and the deposition temperature can be reduced.
A phenylene group optionally having one or more substituents selected from the group consisting of a methyl group, a methoxy group, a cyano group, a deuterium atom, and a phenyl group, a biphenylene group, a terphenylene group, a naphthylene group, and a fluorene-diyl The group, spirobifluorene-diyl group, phenanthrene-diyl group, triphenylene-diyl group, carbazole-diyl group, dibenzofuran-diyl group, or dibenzothiophene-diyl group X ¹ and X ² are highly hole-transporting and driving Since the voltage can be reduced and the deposition temperature can be reduced,
A phenylene group, a methylbenzene-diyl group, a biphenylene group, a naphthylene group, a fluorene-diyl group, or a dibenzofurandyl group is more preferable.

Ar ² , Ar ³ and Ar ⁵ to Ar ¹⁰ have high hole transport properties and can reduce the driving voltage.
(i) phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spirobifluorenyl group, benzofluorenyl group, phenanthryl group, fluoranthenyl group, triphenylenyl group, anthryl group, pyrenyl group, carbazolyl group; , a dibenzofuranyl group, or a dibenzothienyl group, or
(ii) the group represented by (i) is a methyl group, an ethyl group, a methoxy group, an ethoxy group, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylsilyl group, or a carbazolyl; It is preferably a group substituted with one or more groups selected from the group consisting of group, dibenzothienyl group and dibenzofuranyl group.

Ar ² , Ar ³ and Ar ⁵ to Ar ¹⁰ have high hole transport properties and can reduce the driving voltage.
(i′) a phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spirobifluorenyl group, phenanthryl group, fluoranthenyl group, triphenylenyl group, carbazolyl group, dibenzofuranyl group, or dibenzothienyl group; or,
(ii') the group represented by (i') is a methyl group, a methoxy group, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylsilyl group, a carbazolyl group, and a dibenzothienyl group; and a group substituted with one or more groups selected from the group consisting of a dibenzofuranyl group.

Ar ² , Ar ³ and Ar ⁵ to Ar ¹⁰ have high hole-transport properties and can reduce the driving voltage. , fluorophenyl group, triphenylsilylphenyl group, biphenylyl group, methylbiphenylyl group, terphenylyl group, naphthyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, spirobifluorenyl group, phenanthryl group, fluoranthenyl group, triphenylenyl group, 9-phenylcarbazolyl group, dibenzofuranyl group, dibenzothienyl group, naphthylphenyl group, phenylnaphthyl group, phenanthrylphenyl group, carbazolylphenyl group, More preferably, it is a dibenzofuranylphenyl group or a dibenzothienylphenyl group.

Since Ar ¹¹ has a high lateral current suppressing effect,
Biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spirobifluorenyl group optionally having one or more substituents selected from the group consisting of methyl group, methoxy group, cyano group, deuterium atom and phenyl group group, phenanthryl group, triphenylenyl group, carbazolyl group, dibenzofuranyl group or dibenzothienyl group.

Since Ar ¹¹ has a high lateral current suppressing effect,
biphenylyl group, terphenylyl group, naphthyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, spirobifluorenyl group, phenanthryl group, triphenylenyl group, 9-phenylcarbazolyl group, A carbazol-9-yl group, a dibenzofuranyl group, or a dibenzothienyl group is more preferred.

Since Ar ¹² and Ar ¹³ are highly effective in suppressing transverse current,
A phenyl group optionally having one or more substituents selected from the group consisting of a methyl group, a methoxy group, a cyano group, a deuterium atom, and a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spiro A bifluorenyl group, a phenanthryl group, a triphenylenyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothienyl group is preferred.

Since Ar ¹² and Ar ¹³ are highly effective in suppressing transverse current,
phenyl group, methylphenyl group, cyanophenyl group, deuterated phenyl group, fluorophenyl group, biphenylyl group, terphenylyl group, naphthyl group, 9,9-dimethylfluorenyl group, 9,9-diphenylfluorenyl group, A spirobifluorenyl group, a phenanthryl group, a triphenylenyl group, a 9-phenylcarbazolyl group, a carbazol-9-yl group, a dibenzofuranyl group, or a dibenzothienyl group is more preferred.

Since Ar ¹² and Ar ¹³ are highly effective in suppressing transverse current,
A phenyl group, a methylphenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a carbazol-9-yl group, a 9,9-dimethylfluorenyl group, a dibenzofuranyl group, or a dibenzothienyl group is more preferable.

The following (A1) to (A108) are preferable because the expressions (6) to (16) can suppress the transverse current.

Since the expressions (6) to (16) can suppress the transverse current and reduce the drive voltage, it is further that (A1) to (A28) and (A95) to (A107) preferable.

In the amine compound represented by formula (3), when B is represented by formula (4), ^transverse current can be ^suppressed . It is preferably one selected from groups represented by 6) to (16).

In the amine compound represented by the ^formula (3), when B is represented by the formula ( ⁵ ), the transverse current can be suppressed. It is preferably one selected from groups represented by 6) to (16).

In the amine compound represented by the formula (3), when B ^is represented by the formula ( ⁵ ), the transverse current can be suppressed. It is more preferably one selected from groups represented by 6) to (16).
[Specific examples of amine compounds]
Regarding the amine compound according to one aspect of the present disclosure, compounds (F1) to (F184), (G1) to (G168), (H1) to (H342), or (I1) to (I342) are exemplified below. However, the disclosure is not limited to these compounds.

[Organic electroluminescence element]
An organic electroluminescence device (hereinafter sometimes simply referred to as an organic electroluminescence device) containing the amine compounds represented by formulas (1) to (3) will be described below.

An organic electroluminescence device according to one aspect of the present invention contains an amine compound represented by formulas (1) to (3).

The configuration of the organic electroluminescence element is not particularly limited, but includes, for example, the configurations (i) to (v) shown below.

(i): anode/hole injection layer/light emitting layer/cathode (ii): anode/hole injection layer/hole transport layer/light emitting layer/cathode (iii): anode/hole injection layer/hole transport layer /electron-blocking layer/light-emitting layer/cathode (iv): anode/hole-injection layer/hole-transporting layer/electron-blocking layer/light-emitting layer/electron-transporting layer/cathode (v): anode/hole-injecting layer/hole Transport layer/Electron blocking layer/Emitting layer/Electron transport layer/Electron injection layer/Cathode The amine compounds represented by the formulas (1) to (3) are excellent in suppressing lateral current in the organic electroluminescence device. It is preferably included in the hole injection layer and/or the hole transport layer and/or the electron blocking layer. In addition, the amine compounds represented by formulas (1) to (3) are included in the hole injection layer and the hole transport layer because they are excellent in the light emission characteristics, driving voltage, and life of the organic electroluminescence device. is more preferred.

Hereinafter, the organic electroluminescence device according to one aspect of the present invention will be described in more detail with reference to FIG. 1, taking the above configuration (v) as an example.

The organic electroluminescence element shown in FIG. 1 has a so-called bottom emission type element configuration, but the organic electroluminescence element according to one aspect of the present invention is not limited to the bottom emission type element configuration. do not have. That is, the organic electroluminescence device according to one aspect of the present invention may have other known device configurations such as top emission type.

FIG. 1 is a schematic cross-sectional view showing an example of a laminated structure of an organic electroluminescence element according to one aspect of the present invention.

The organic electroluminescence element 100 includes a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an electron blocking layer 5, a light emitting layer 6, an electron transport layer 7, an electron injection layer 8, and a cathode 9 in this order. Prepare with. However, some of these layers may be omitted, or conversely, other layers may be added. For example, a hole-blocking layer may be provided between the light-emitting layer 6 and the electron-transporting layer 7, the electron-blocking layer 5 may be omitted, and the light-emitting layer 6 may be provided directly on the hole-transporting layer 4. good too. In addition, a single layer having the functions of a plurality of layers, such as a hole transport/electron blocking layer having both the function of the hole transport layer 4 and the function of the electron blocking layer 5 in a single layer. , may be provided instead of the plurality of layers. Further, for example, the single-layer electron transport layer 7 may be composed of multiple layers.

The organic electroluminescence device 100 in which the hole injection layer 3 and the hole transport layer 4 contain the amine compounds represented by formulas (1) to (3) will be described below.
[Substrate 1]
The substrate 1 is not particularly limited, and examples thereof include a glass plate, a quartz plate, a plastic plate and the like.

Examples of the substrate 1 include a glass plate, a quartz plate, a plastic plate, and a plastic film. Among these, a glass plate, a quartz plate, and a transparent plastic film are preferable.

Examples of light-transmitting plastic films include polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC ), cellulose triacetate (TAC), cellulose acetate propionate (CAP), and the like.

In addition, in the case of the configuration in which light emission is extracted from the substrate 1 side, the substrate 1 is transparent to the wavelength of light.
[Anode 2]
An anode 2 is provided on the substrate 1 (on the hole injection layer 3 side).

Materials for the anode include metals, alloys, electrically conductive compounds, and mixtures thereof having a large work function (for example, 4 eV or more). Specific examples of materials for the anode include metals such as Au; conductive transparent materials such as CuI, indium tin oxide (ITO), SnO ₂ and ZnO.

For organic electroluminescent devices configured such that emitted light is extracted through the anode, the anode is formed of a conductive transparent material that is transparent or substantially transparent to the emitted light.
[Hole injection layer 3]
A hole injection layer 3 is provided between the anode 2 and a hole transport layer 4 which will be described later.

The hole injection layer functions as a hole injection layer. By interposing a hole-injecting layer between the anode and the light-emitting layer, holes are injected into the light-emitting layer at a lower electric field. In particular, in the present invention, it is preferable to use the amine compounds represented by the formulas (1) to (3) as the material for the hole injection layer.

Also, the hole injection layer may further include an electron acceptor p-type dopant. In this case, the p-type dopant may be included in an amount of 0.5-20% by weight of the hole injection layer. The p-type dopant is not limited as long as it is used in an organic light-emitting device, and for example, a compound represented by the following chemical formula can be used:

[Hole transport layer 4]
A hole transport layer 4 is provided between the hole injection layer 3 and an electron blocking layer 5 which will be described later.

The hole transport layer is formed on the hole injection layer to improve the mobility of holes and improve the power efficiency of the organic light emitting device.

As the hole-transporting substance, a substance capable of smoothly injecting holes from the anode and transferring them to the light-emitting layer, and having a high mobility for holes, is suitable. The hole transport material is not limited as long as it is used in an organic light emitting device, and for example, an aromatic tertiary amine compound can be used.

In addition, the hole transport layer may contain the amine compounds represented by the above formulas (1) to (3).

Both the hole transport layer and the hole injection layer preferably contain the amine compounds represented by the formulas (1) to (3).

The hole transport layer may have a single structure composed of one or more materials, or may have a laminated structure composed of a plurality of layers having the same composition or different compositions.
[Electron blocking layer 5]
An electron-blocking layer 5 is provided between the hole-transporting layer 4 and the light-emitting layer 6, which will be described later.

The electron blocking layer functions as a layer that confines electrons in the light emitting layer. That is, electrons injected from the cathode and transported from the electron injection layer and/or the electron transport layer to the light emitting layer are blocked by the hole injection layer and/or the electron blocking layer due to the energy barrier present at the interface between the light emitting layer and the electron blocking layer. Leakage into the pore transport layer is suppressed. As a result, electrons are accumulated at the interface in the light-emitting layer, resulting in an effect such as an improvement in light-emitting efficiency, and an organic electroluminescence device having excellent light-emitting performance can be obtained.

The electron-blocking layer also has the function of transmitting holes injected from the anode to the light-emitting layer. of holes are injected into the light-emitting layer.

The material for the electron blocking layer has at least one of hole injection, hole transport, and electron blocking properties. The material of the electron blocking layer may be either organic or inorganic.

Specific examples of materials for the electron blocking layer include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, and styryl. Anthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers (especially thiophene oligomers), porphyrin compounds, aromatic tertiary amine compounds, styrylamine compounds, etc. . Among these, porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds are preferred, and aromatic tertiary amine compounds are particularly preferred, from the viewpoint of good performance of the organic electroluminescent device.

Specific examples of aromatic tertiary amine compounds and styrylamine compounds include N,N,N',N'-tetraphenyl-4,4'-diaminophenyl, N,N'-diphenyl-N,N'- Bis(m-tolyl)-[1,1′-biphenyl]-4,4′-diamine (TPD), 2,2-bis(4-di-p-tolylaminophenyl)propane, 1,1-bis( 4-di-p-tolylaminophenyl)cyclohexane, N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl, 1,1-bis(4-di-p-tolylamino phenyl)-4-phenylcyclohexane, bis(4-dimethylamino-2-methylphenyl)phenylmethane, bis(4-di-p-tolylaminophenyl)phenylmethane, N,N'-diphenyl-N,N'- Di(4-methoxyphenyl)-4,4'-diaminobiphenyl, N,N,N',N'-tetraphenyl-4,4'-diaminodiphenyl ether, 4,4'-bis(diphenylamino)quadriphenyl , N,N,N-tri(p-tolyl)amine, 4-(di-p-tolylamino)-4′-[4-(di-p-tolylamino)styryl]stilbene, 4-N,N-diphenylamino -(2-diphenylvinyl)benzene, 3-methoxy-4'-N,N-diphenylaminostilbenzene, N-phenylcarbazole, 4,4'-bis[N-(1-naphthyl)-N-phenylamino] Biphenyl (NPD), 4,4′,4″-tris[N-(m-tolyl)-N-phenylamino]triphenylamine (MTDATA), and the like, but are not limited to these.

The electron blocking layer may have a single structure made of one or more materials, or may have a laminated structure made up of multiple layers of the same composition or different compositions.

Amine compounds represented by the above formulas (1) to (3) can also be used in the electron blocking layer.
[Light emitting layer 6]
A light-emitting layer 6 is provided between the electron-blocking layer 5 and an electron-transporting layer 7, which will be described later.

Materials for the light-emitting layer include phosphorescent light-emitting materials, fluorescent light-emitting materials, and thermally activated delayed fluorescent light-emitting materials. In the light-emitting layer, electron-hole pairs recombine, resulting in light emission.

The light-emitting layer may consist of a single small molecule material or a single polymer material, but more commonly consists of a host material doped with a guest compound. Emission comes primarily from dopants and can have any color.

Examples of host materials include compounds having biphenylyl groups, fluorenyl groups, triphenylsilyl groups, carbazole groups, pyrenyl groups, and anthryl groups. More specifically, DPVBi (4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl), BCzVBi (4,4'-bis(9-ethyl-3-carbazovinylene) 1, 1′-biphenyl), TBADN (2-tert-butyl-9,10-di(2-naphthyl)anthracene), ADN (9,10-di(2-naphthyl)anthracene), CBP (4,4′-bis (carbazol-9-yl)biphenyl), CDBP (4,4′-bis(carbazol-9-yl)-2,2′-dimethylbiphenyl), 2-(9-phenylcarbazol-3-yl)-9- [4-(4-phenylphenylquinazolin-2-yl)carbazole, 9,10-bis(biphenyl)anthracene, and the like, but are not limited thereto.

Examples of fluorescent dopants include anthracene, pyrene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyran compounds, thiopyran compounds, polymethine compounds, pyrylium, thiapyrylium compounds, fluorene derivatives, periflanthene derivatives, and indenoperylenes. Examples include, but are not limited to, derivatives, bis(azinyl)amine boron compounds, bis(azinyl)methane compounds, carbostyril compounds, boron compounds, cyclic amine compounds, and the like.

Also, the fluorescent dopant may be a combination of two or more selected from these.

Examples of phosphorescent dopants include, but are not limited to, organometallic complexes of transition metals such as iridium, platinum, palladium, and osmium.

Specific examples of fluorescent dopants and phosphorescent dopants include Alq3 (tris(8-hydroxyquinoline)aluminum), DPAVBi (4,4′-bis[4-(di-p-tolylamino)styryl]biphenyl), perylene, bis[ 2-(4-n-hexylphenyl)quinoline](acetylacetonato)iridium(III), Ir(PPy)3(tris(2-phenylpyridine)iridium(III)), and FIrPic (bis(3,5- difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium (III)))) and the like, but are not limited thereto.

Also, the luminescent material is not limited to being contained only in the luminescent layer. For example, the light-emitting material may be contained in a layer adjacent to the light-emitting layer (electron blocking layer 5 or electron transport layer 7). This can further increase the luminous efficiency of the organic electroluminescence device.

The light-emitting layer may have a single-layer structure composed of one or more materials, or may have a laminated structure composed of a plurality of layers having the same composition or different compositions.
[Electron transport layer 7]
An electron transport layer 7 is provided between the light emitting layer 6 and an electron injection layer 8 which will be described later.

The electron transport layer has the function of transmitting electrons injected from the cathode to the light emitting layer. By interposing an electron-transporting layer between the cathode and the light-emitting layer, electrons are injected into the light-emitting layer at a lower electric field.

Specific examples of materials for the electron transport layer include tris(8-quinolinolato)aluminum derivatives, imidazole derivatives, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoline derivatives, quinoxaline derivatives, oxadiazole derivatives, phosphor derivatives, silole derivatives, phosphine oxide derivatives and the like. Among these, triazine derivatives and pyrimidine derivatives are preferable from the viewpoint of good performance of the organic electroluminescence device.

In addition, the electron transport layer may further contain one or more selected from conventionally known electron transport materials in addition to the materials shown above.

Conventionally known electron-transporting materials include alkali metal complexes, alkaline earth metal complexes, earth metal complexes, and the like. Alkali metal complexes, alkaline earth metal complexes, and earth metal complexes include, for example, 8-hydroxyquinolinatolithium (Liq), bis(8-hydroxyquinolinato)zinc, and bis(8-hydroxyquinolinato)copper. , bis(8-hydroxyquinolinato)manganese, tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis (10-hydroxybenzo[h]quinolinate) beryllium, bis(10-hydroxybenzo[h]quinolinate)zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinate)(o -cresolato) gallium, bis(2-methyl-8-quinolinato)-1-naphtholato aluminum, bis(2-methyl-8-quinolinato)-2-naphtholato gallium, and the like. Inorganic compounds such as Yb, Li and Ca may also be used.

The electron-transporting layer may have a single-layer structure composed of one or more materials, or may have a laminated structure composed of a plurality of layers having the same composition or different compositions.
[Electron injection layer 8]
An electron injection layer 8 is provided between the electron transport layer 7 and a cathode 9 which will be described later.

The electron injection layer has the function of transferring electrons injected from the cathode to the light emitting layer. By interposing an electron injection layer between the cathode and the light emitting layer, electrons are injected into the light emitting layer at a low electric field.

Materials for the electron injection layer include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, frelenylidenemethane, anthraquinodimethane, anthrone, and the like. Examples include organic compounds. Materials for the electron injection layer include various oxides such as SiO2, AlO, SiN, SiON, AlON, GeO, LiO, LiON, TiO, TiON, TaO, TaON, TaN, LiF, C, Yb, fluorides, Inorganic compounds such as nitrides and oxynitrides are also included.
[Cathode 9]
A cathode 9 is provided on the electron injection layer 8 .

In the case of an organic electroluminescence device configured so that only light emitted through the anode is taken out, the cathode can be made of any conductive material.

Examples of materials for the cathode include metals with a small work function (hereinafter also referred to as electron-injecting metals), alloys, electrically conductive compounds, and mixtures thereof. Here, a metal with a small work function is, for example, a metal of 4 eV or less.

Specific examples of cathode materials include sodium, sodium-potassium alloys, magnesium, lithium, magnesium/copper mixtures, magnesium/silver mixtures, magnesium/aluminum mixtures, magnesium/indium mixtures, aluminum/aluminum oxide (Al ₂ O ₃ ). mixtures, indium, lithium/aluminum mixtures, rare earth metals, and the like.

Among these, mixtures of electron-injecting metals and second metals, which are stable metals with a larger work function value, such as magnesium/silver mixtures, magnesium /aluminum mixtures, magnesium/ _indium mixtures, aluminum/aluminum oxide ( _Al2O3 ) mixtures, lithium/aluminum mixtures, etc. are preferred.

Next, a method for producing the amine compounds represented by formulas (1) to (3) will be described.

The arylamine compounds represented by the above formulas (1) to (3) can be produced by the methods shown in the following synthetic routes (p) to (s), but are not limited to these.

In formulas (17) to (31),
The definitions of Ar ¹ to Ar ⁸ , R ¹ to R ⁶ , L ¹ to L ⁶ , X ¹ to X ³ , and B are the same as Ar ¹ to Ar ⁸ and R ¹ in formulas (1) to (3), respectively. -R ⁶ , L ¹ -L ⁶ , X ¹ -X ³ , and the same as defined for B;
Y ¹ to Y ⁷ each independently represent a halogen atom;
Examples of halogen atoms represented by Y ¹ to Y ⁷ include fluorine, chlorine, bromine and iodine atoms.

Examples of B(OR ¹ ) ₂ include B(OH) ₂ , B(OMe) ₂ , B(O ⁱ Pr) ₂ , B(OBu) ₂ and B(OPh) ₂ . Me is a methyl group, ⁱ Pr is an isopropyl group, Bu is a butyl group, and Ph is a phenyl group.

Examples of B(OR ¹ ) ₂ when two OR ¹ groups and a boron atom form a ring together include groups represented by the following (I) to (VI) can be exemplified, and the group represented by (II) is preferable in that the yield is good.

The carbazole compound, formula (19), formula (23) and formula (27) can be produced according to, for example, Japanese Patent No. 5609256 and Japanese Patent No. 6115075, respectively. Moreover, you may use a commercial item.

The amination reaction in the synthetic routes (p) to (s) comprises a halogen compound represented by formula (19), formula (23), formula (27), or formula (31), formula (20), formula ( 24), a method of reacting an amine compound represented by formula (28), formula (29) or formula (30) in the presence of a palladium catalyst and a base, under general Buchwald-Hartwig amination reaction conditions. can be applied.

Palladium catalysts used in the above-mentioned amination reaction include, for example, palladium salts such as palladium chloride, palladium acetate, palladium trifluoroacetate, and palladium nitrate. Furthermore, complex compounds such as π-allylpalladium chloride dimer, palladium acetylacetonato, tris(dibenzylideneacetone)dipalladium, bis(dibenzylideneacetone)palladium, dichlorobis(acetonitrile)palladium, dichlorobis(benzonitrile)palladium; Dichlorobis(triphenylphosphine)palladium, Tetrakis(triphenylphosphine)palladium, Dichloro(1,1′-bis(diphenylphosphino)ferrocene)palladium, Bis(tri-tert-butylphosphine)palladium, Bis(tricyclohexylphosphine) palladium complexes having a tertiary phosphine as a ligand, such as palladium and dichlorobis(tricyclohexylphosphine)palladium; These can also be prepared in a reaction system by adding a tertiary phosphine to a palladium salt or complex compound.

Tertiary phosphines include, for example, triphenylphosphine, trimethylphosphine, tributylphosphine, tri(tert-butyl)phosphine, tricyclohexylphosphine, tert-butyldiphenylphosphine, 9,9-dimethyl-4,5-bis( diphenylphosphino)xanthene, 2-(diphenylphosphino)-2′-(N,N-dimethylamino)biphenyl, 2-(di-tert-butylphosphino)biphenyl, 2-(dicyclohexylphosphino)biphenyl, bis (diphenylphosphino)methane, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane, 1,4-bis(diphenylphosphino)butane, 1,1′-bis( diphenylphosphino)ferrocene, tri(2-furyl)phosphine, tri(o-tolyl)phosphine, tris(2,5-xylyl)phosphine, (±)-2,2′-bis(diphenylphosphino)-1, 1'-binaphthyl, 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl and the like.

Among them, a palladium complex having a tertiary phosphine as a ligand is preferable in that the yield is good, and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl, tri(o-tolyl)phosphine , tri(tert-butyl)phosphine, 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene or tricyclohexylphosphine as ligands are more preferred.

The molar ratio of the tertiary phosphine and the palladium salt or complex compound is preferably in the range of 1:10 to 10:1, more preferably in the range of 1:2 to 3:1 in terms of good yield. preferable. Although the amount of the palladium catalyst used in the amination reaction described above is not limited, the molar equivalent of the palladium catalyst is preferably in the range of 0.005 to 0.5 molar equivalents relative to the amine compound in terms of good yield. preferable.

Examples of the base used in the amination reaction include metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide; metal carbonates such as sodium carbonate, potassium carbonate, lithium carbonate and cesium carbonate; Metal acetates such as potassium and sodium acetate, metal phosphates such as potassium phosphate and sodium phosphate, metal fluoride salts such as sodium fluoride, potassium fluoride, and cesium fluoride, sodium methoxide, potassium methoxide, Metal alkoxides such as sodium ethoxide, potassium isopropyloxide, sodium tert-butoxide, potassium tert-butoxide and the like can be mentioned. Among them, sodium tert-butoxide is preferable in that the reaction yield is good. There are no particular restrictions on the amount of base used. The molar ratio between the base and the amine compound is preferably in the range of 1:2 to 10:1, more preferably in the range of 1:1 to 4:1, in terms of good reaction yield.

After the completion of the amination reaction, the target product can be obtained by appropriately combining general purification treatments such as recrystallization, column chromatography, sublimation purification, and preparative HPLC as necessary.

EXAMPLES The present invention will be described in more detail below based on examples, but the present invention should not be construed as being limited by these examples.
[ ¹ H-NMR measurement]
Bruker ASCEND HD (400 MHz; manufactured by BRUKER) was used for ¹ H-NMR measurement. ¹ H-NMR was measured using deuterated chloroform (CDCl ₃ ) as a measurement solvent and tetramethylsilane (TMS) as an internal standard substance.
[FDMS (Field Desorption Mass Spectroscopy) measurement]
FDMS measurement was performed using Hitachi M-80B.
[Lateral current measurement]
The lateral current was measured using a Source Meter 2400 manufactured by Keithley Instruments.

Synthesis Example 1 (N-([1,1':2',1'':4'',1'''-quaterphenyl]-4'''-yl)-9-(naphthalen-1-yl )-9H-carbazol-4-amine synthesis)

5.0 g (15 mmol) of 4-chloro-9-(naphthalen-1-yl)-9H-carbazole, [1,1′:2′,1″:4″, are placed in a 100 mL three-necked flask under a nitrogen stream. ,1'''-quaterphenyl]-4'''-amine 7.4 g (23 mmol), sodium-tert-butoxide 2.2 g (23 mmol), xylene 20 mL, palladium acetate 34 mg (0.15 mmol) and tri( 0.37 g (0.46 mmol) of a 25% by weight xylene solution of tert-butyl)phosphine was added and stirred at 140° C. for 15 hours. After allowing to cool to room temperature, 25 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent is distilled off under reduced pressure, and the obtained solid is recrystallized with a mixed solvent of toluene and butanol to obtain N-([1,1′:2′,1″:4″, 1'''-Quaterphenyl]-4'''-yl)-9-(naphthalen-1-yl)-9H-carbazol-4-amine 7.0 g (11 mmol) of white solid was isolated (yield rate 75%).

　Compounds were identified by FDMS measurement.

FDMS: 612
Synthesis Example 2 (Synthesis of N-(9,9-dimethylfluoren-2-yl)-N-(9-phenylcarbazol-2-yl)amine)

Under a nitrogen stream, 5.0 g (16 mmol) of 4-bromo-9-phenylcarbazole, 4.9 g (23 mmol) of 2-amino-9,9-dimethylfluorene, and 2.5 g of sodium-tert-butoxide are placed in a 300 mL three-necked flask. (26 mmol), xylene 52 mL, palladium acetate 35 mg (0.16 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene 0.18 g (0.31 mmol) were added and the mixture was heated at 140°C for 20 hours. Stirred. After allowing to cool to room temperature, 100 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent is distilled off under reduced pressure, and the obtained solid is recrystallized with a mixed solvent of toluene and butanol to give N-(9,9-dimethylfluoren-2-yl)-N-(9 -Phenylcarbazol-4-yl)amine 4.6 g (10 mmol) of white solid was isolated (66% yield).

Identification of the compound was performed by ¹ H-NMR measurement.

¹ H—NMR(CDCl ₃ ); 8.08 (d, J=8.00 Hz, 1H), 7.58-7.67 (m, 6H), 7.50 (t, J=7.2 Hz , 1H), 7.18-7.42 (m, 8H), 7.15 (d, J = 8.00Hz, 1H), 7.05 (d, J = 7.2Hz, 1H), 6.38 (s, 1H), 1.47 (s, 6H)
Synthesis Example 3 (Synthesis of N-([1,1′:4′,1″-terphenyl]-2-yl)-9-(phenanthren-9-yl)-9H-carbazol-4-amine)

Under a nitrogen stream, 6.4 g (19 mmol) of 9-(phenanthren-9-yl)-4-chloro-9H-carbazole and [1,1′:4′,1″-terphenyl] are placed in a 100 mL three-necked flask. -2-amine 6.9 g (28 mmol), sodium-tert-butoxide 2.7 g (28 mmol), xylene 20 mL, palladium acetate 42 mg (0.19 mmol), and 25% by weight xylene solution of tri(tert-butyl)phosphine 0. 45 g (0.56 mmol) was added and stirred at 140° C. for 20 hours. After allowing to cool to room temperature, 30 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent is distilled off under reduced pressure, and the obtained solid is recrystallized with a mixed solvent of toluene and butanol to obtain N-([1,1′:4′,1″-terphenyl]- 2-yl)-9-(phenanthren-9-yl)-9H-carbazol-4-amine 8.7 g (15 mmol) of white solid was isolated (80% yield).

FDMS: 586
Synthesis Example 4 (Synthesis of 9-([1,1′-biphenyl]-4-yl)-N-(4-phenylnaphthalen-1-yl)-9H-carbazol-4-amine)

Under a nitrogen stream, 5.9 g (17 mmol) of 9-([1,1'-biphenyl]-4-yl)-4-chloro-9H-carbazole and 5 of 4-phenylnaphthalen-1-amine are placed in a 100 mL three-necked flask. .5 g (25 mmol), 2.4 g (25 mmol) of sodium-tert-butoxide, 20 mL of xylene, 37 mg (0.17 mmol) of palladium acetate, and 0.40 g (0.50 mmol) of a 25% by weight xylene solution of tri(tert-butyl)phosphine ) was added and stirred at 140° C. for 15 hours. After allowing to cool to room temperature, 15 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent is distilled off under reduced pressure, and the obtained solid is recrystallized with a mixed solvent of toluene and butanol to obtain 9-([1,1′-biphenyl]-4-yl)-N-( 4-Phenylnaphthalen-1-yl)-9H-carbazol-4-amine 7.2 g (14 mmol) of white solid was isolated (yield 81%).

FDMS: 536
Synthesis Example 5 (Synthesis of N-(o-terphenyl-4'-yl)-N-(9-phenylcarbazol-2-yl)amine)

In a 200 mL three-necked flask under nitrogen stream, 10 g (31 mmol) of 2-bromo-9-phenylcarbazole, 11 g (47 mmol) of o-terphenyl-4'-amine, 5.1 g (53 mmol) of sodium-tert-butoxide, o -Xylene 100 mL, palladium acetate 0.070 g (0.31 mmol), and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene 0.36 g (0.62 mmol) are added and stirred at 140°C for 15 hours. bottom. After allowing to cool to room temperature, 40 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent is distilled off under reduced pressure, and the obtained solid is recrystallized with a mixed solvent of toluene and butanol to obtain N-(o-terphenyl-4'-yl)-N-(9-phenyl). 9.5 g (20 mmol) of a white solid of carbazol-2-yl)amine were isolated (63% yield).

Identification of the compound was performed by ¹ H-NMR measurement.

¹ H-NMR (CDCl ₃ ); 8.00-8.05 (m, 2H), 7.51-7.61 (m, 4H), 7.43-7.48 (m, 1H), 7. 30-7.36 (m, 3H), 7.23-7.28 (m, 3H), 7.14-7.22 (m, 6H), 7.04-7.12 (m, 6H), 6.01 (s, 1H)
Synthesis Example 6 Synthesis of 3-(4-chlorophenyl)-carbazole)

Under a nitrogen stream, 30 g (122 mmol) of 3-bromo-carbazole, 21 g (134 mmol) of 4-chlorophenylboronic acid, 183 mL (366 mmol) of 2M tripotassium phosphate aqueous solution, and 410 mL of THF are placed in a 1000 mL three-necked flask at 70°C for 20 hours. Stirred. After allowing to cool to room temperature, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with a mixed solvent of toluene and butanol to isolate 28 g (101 mmol) of 3-(4-chlorophenyl)-carbazole as a white solid. (83% yield).

　Compounds were identified by FDMS measurement.

FDMS: 277
Synthesis Example 7 (Synthesis of 3-(4-chlorophenyl)-9-(m-terphenyl-2′-yl)carbazole)

Under a nitrogen stream, 40 g (163 mmol) of 4-bromo-carbazole, 28 g (179 mmol) of 4-chlorophenylboronic acid, 244 mL (488 mmol) of 2M tripotassium phosphate aqueous solution, and 540 mL of THF are placed in a 1000 mL three-necked flask at 70°C for 24 hours. Stirred. After allowing to cool to room temperature, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with a mixed solvent of toluene and butanol to obtain 38 g (0.14 mol) of 4-(4-chlorophenyl)-carbazole as a white solid. Separated (85% yield).

　Compounds were identified by FDMS measurement.

FDMS: 277
Synthesis Example 8 (Synthesis of 9-([1,1′:4′,1″-terphenyl]-2-yl)-3-(4-chlorophenyl)-9H-carbazole)

Under a nitrogen stream, 3.0 g (11 mmol) of 3-(4-chlorophenyl)-9H-carbazole obtained in Synthesis Example 6 and 2-fluoro-1,1′:4′,1″ were placed in a 100 mL three-necked flask. -Terphenyl 3.2 g (13 mmol), tripotassium phosphate 4.6 g (22 mmol) and DMSO 20 mL were added and stirred at 180°C for 23 hours. After standing to cool to room temperature, 50 mL of pure water was added and stirred to precipitate a solid. The resulting solid was collected by filtration and recrystallized with a mixed solvent of toluene and butanol to give 9-([1,1′:4′,1″-terphenyl]-2-yl)-3-( 4-Chlorophenyl)-9H-carbazole (4.4 g (8.6 mmol) of white solid was isolated (yield 80%).

　Compounds were identified by FDMS measurement.

FDMS: 505
Synthesis Example 9 (Synthesis of 9-([1,1′:3′,1″-terphenyl]-4′-yl)-3-(4-chlorophenyl)-9H-carbazole)

Under a nitrogen stream, 3.0 g (11 mmol) of 3-(4-chlorophenyl)-9H-carbazole obtained in Synthesis Example 6 and 4'-fluoro-1,1':3',1' were placed in a 100 mL three-necked flask. 2.7 g (11 mmol) of '-terphenyl, 4.6 g (22 mmol) of tripotassium phosphate and 20 mL of DMSO were added and stirred at 180°C for 23 hours. After standing to cool to room temperature, 50 mL of pure water was added and stirred to precipitate a solid. The resulting solid was collected by filtration and recrystallized with a mixed solvent of toluene and butanol to give 9-([1,1′:3′,1″-terphenyl]-4′-yl)-3- (4-Chlorophenyl)-9H-carbazole (4.5 g (8.9 mmol) of white solid was isolated (yield 82%).

　Compounds were identified by FDMS measurement.

FDMS: 505
Synthesis Example 10 (Synthesis of 3-(4-chlorophenyl)-9-(m-terphenyl-2′-yl)carbazole)

Under a nitrogen stream, 5.5 g (20 mmol) of 3-(4-chlorophenyl)-carbazole obtained in Synthesis Example 6, 5.9 g (24 mmol) of 2-fluoro-m-terphenyl, phosphoric acid and 13 g (59 mmol) of tripotassium and 20 mL of DMSO were stirred at 150° C. for 20 hours. After standing to cool to room temperature, 20 mL of pure water was added and stirred to precipitate a solid. The resulting solid was collected by filtration and recrystallized with a mixed solvent of toluene and butanol to give 3-(4-chlorophenyl)-9-(m-terphenyl-2'-yl)carbazole as a white solid, 7.2 g. (14 mmol) was isolated (72% yield).

　Compounds were identified by FDMS measurement.

FDMS: 505
Synthesis Example 11 (Synthesis of 3-(4-chlorophenyl)-9-(2-(dibenzo[b,d]furan-2-yl)phenyl)-9H-carbazole)

Under a nitrogen stream, 3.0 g (11 mmol) of 3-(4-chlorophenyl)-9H-carbazole obtained in Synthesis Example 6 and 2-(2-fluorophenyl)dibenzo[b,d]furan were placed in a 100 mL three-necked flask. 2.8 g (11 mmol), 4.6 g (22 mmol) of tripotassium phosphate and 20 mL of DMSO were added and stirred at 180° C. for 23 hours. After standing to cool to room temperature, 50 mL of pure water was added and stirred to precipitate a solid. The resulting solid was collected by filtration and recrystallized with a mixed solvent of toluene and butanol to give 3-(4-chlorophenyl)-9-(2-(dibenzo[b,d]furan-2-yl)phenyl). -9H-carbazole (4.2 g (8.1 mmol) of white solid was isolated (yield 75%).

　Compounds were identified by FDMS measurement.

FDMS: 519
Synthesis Example 12 (Synthesis of 3-(4-chlorophenyl)-9-(2,6-di(naphthalen-1-yl)phenyl)-9H-carbazole)

Under a nitrogen stream, 2.6 g (9.4 mmol) of 3-(4-chlorophenyl)-9H-carbazole obtained in Synthesis Example 6, 1,1′-(2-fluoro-1,3 -phenylene)dinaphthalene 3.3 g (9.4 mmol), tripotassium phosphate 4.0 g (19 mmol) and DMSO 20 mL were added and stirred at 180°C for 23 hours. After standing to cool to room temperature, 50 mL of pure water was added and stirred to precipitate a solid. The resulting solid was collected by filtration and recrystallized with a mixed solvent of toluene and butanol to give 3-(4-chlorophenyl)-9-(2,6-di(naphthalen-1-yl)phenyl)-9H- Carbazole.　Compounds were identified by FDMS measurement.

FDMS: 605
Synthesis Example 13 (Synthesis of 9-([1,1′:4′,1″-terphenyl]-2′-yl)-3-(4-chloronaphthalen-1-yl)-9H-carbazole)

Under a nitrogen stream, 2.7 g (9.7 mmol) of 3-(4-chlorophenyl)-9H-carbazole and 2'-fluoro-1,1':4',1''-terphenyl were placed in a 100 mL three-necked flask. 4 g (9.7 mmol), tripotassium phosphate 4.1 g (19 mmol), and DMSO 20 mL were added, and the mixture was stirred at 180°C for 23 hours. After standing to cool to room temperature, 50 mL of pure water was added and stirred to precipitate a solid. The resulting solid was collected by filtration and recrystallized with a mixed solvent of toluene and butanol to give 9-([1,1′:4′,1″-terphenyl]-2′-yl)-3- (4-Chloronaphthalen-1-yl)-9H-carbazole (4.7 g (8.5 mmol) of white solid was isolated (yield 87%).

　Compounds were identified by FDMS measurement.

FDMS: 555
Synthesis Example 14 (Synthesis of 3-(4-chlorophenyl)-9-(2-methyl-6-(naphthalen-2-yl)phenyl)-9H-carbazole)

3.0 g (11 mmol) of 3-(4-chlorophenyl)-9H-carbazole obtained in Synthesis Example 6 and 2-(2-fluoro-3-methylphenyl)naphthalene were placed in a 100 mL three-necked flask under a nitrogen stream. 1 g (13 mmol), 4.6 g (22 mmol) of tripotassium phosphate, and 20 mL of DMSO were added and stirred at 180° C. for 23 hours. After standing to cool to room temperature, 50 mL of pure water was added and stirred to precipitate a solid. The resulting solid was collected by filtration and recrystallized with a mixed solvent of toluene and butanol to give 3-(4-chlorophenyl)-9-(2-methyl-6-(naphthalen-2-yl)phenyl)-9H. -Carbazole (3.6 g (7.3 mmol) of white solid was isolated (yield 68%).

　Compounds were identified by FDMS measurement.

FDMS: 493
Synthesis Example 15 (Synthesis of 9-([1,1′:4′,1″-terphenyl]-2-yl)-4-(4-chlorophenyl)-9H-carbazole)

Under a nitrogen stream, 3.5 g (13 mmol) of 4-(4-chlorophenyl)-9H-carbazole obtained in Synthesis Example 7 and 2-fluoro-1,1′:4′,1″ were placed in a 100 mL three-necked flask. -Terphenyl 3.8 g (15 mmol), tripotassium phosphate 5.3 g (25 mmol) and DMSO 20 mL were added and stirred at 180°C for 23 hours. After standing to cool to room temperature, 50 mL of pure water was added and stirred to precipitate a solid. The resulting solid was collected by filtration and recrystallized with a mixed solvent of toluene and butanol to give 9-([1,1′:4′,1″-terphenyl]-2-yl)-4-( 4-Chlorophenyl)-9H-carbazole (4.7 g (9.2 mmol) of white solid was isolated (yield 73%).

　Compounds were identified by FDMS measurement.

FDMS: 505
Synthesis Example 16 (Synthesis of 9-([1,1′:2′,1″-terphenyl]-3′-yl)-4-(4-chlorophenyl)-9H-carbazole)

Under a nitrogen stream, 3.5 g (13 mmol) of 4-(4-chlorophenyl)-9H-carbazole obtained in Synthesis Example 7 and 3'-fluoro-1,1':2',1' were placed in a 100 mL three-necked flask. 3.8 g (15 mmol) of '-terphenyl, 5.3 g (25 mmol) of tripotassium phosphate and 20 mL of DMSO were added and stirred at 180°C for 23 hours. After standing to cool to room temperature, 50 mL of pure water was added and stirred to precipitate a solid. The resulting solid was collected by filtration and recrystallized with a mixed solvent of toluene and butanol to give 9-([1,1′:2′,1″-terphenyl]-3′-yl)-4- (4-Chlorophenyl)-9H-carbazole (4.8 g (9.5 mmol) of white solid was isolated (yield 75%).

　Compounds were identified by FDMS measurement.

FDMS: 505
Synthesis Example 17 (Synthesis of 9-([1,1′:3′,1″-terphenyl]-4′-yl)-4-(4-chlorophenyl)-9H-carbazole)

Under a nitrogen stream, 3.0 g (11 mmol) of 4-(4-chlorophenyl)-9H-carbazole obtained in Synthesis Example 7 and 4'-fluoro-1,1':3',1' were placed in a 100 mL three-necked flask. 3.2 g (13 mmol) of '-terphenyl, 4.6 g (22 mmol) of tripotassium phosphate and 20 mL of DMSO were added and stirred at 180°C for 23 hours. After standing to cool to room temperature, 50 mL of pure water was added and stirred to precipitate a solid. The resulting solid was collected by filtration and recrystallized with a mixed solvent of toluene and butanol to give 9-([1,1′:3′,1″-terphenyl]-4′-yl)-4- (4-Chlorophenyl)-9H-carbazole (4.3 g (8.4 mmol) of white solid was isolated (yield 78%).

　Compounds were identified by FDMS measurement.

FDMS: 505
Synthesis Example 18 (Synthesis of 4-(4-chlorophenyl)-9-(2-(dibenzo[b,d]thiophen-2-yl)phenyl)-9H-carbazole)

Under a nitrogen stream, 2.8 g (10 mmol) of 4-(4-chlorophenyl)-9H-carbazole obtained in Synthesis Example 7 and 2-(2-fluorophenyl)dibenzo[b,d]thiophene were placed in a 100 mL three-necked flask. 3.4 g (12 mmol), 4.3 g (20 mmol) of tripotassium phosphate and 20 mL of DMSO were added and stirred at 180° C. for 23 hours. After standing to cool to room temperature, 50 mL of pure water was added and stirred to precipitate a solid. The resulting solid was collected by filtration and recrystallized with a mixed solvent of toluene and butanol to give 4-(4-chlorophenyl)-9-(2-(dibenzo[b,d]thiophen-2-yl)phenyl). -9H-carbazole (3.7 g (7.0 mmol) of white solid was isolated (yield 69%).

　Compounds were identified by FDMS measurement.

FDMS: 535
Synthesis Example 19 (Synthesis of 4-(4-chlorophenyl)-9-(2-methyl-6-(naphthalen-2-yl)phenyl)-9H-carbazole)

Under a nitrogen stream, 3.2 g (12 mmol) of 4-(4-chlorophenyl)-9H-carbazole obtained in Synthesis Example 7 and 3 of 2-(2-fluoro-3-methylphenyl)naphthalene were placed in a 100 mL three-necked flask. .3 g (14 mmol), 4.9 g (23 mmol) of tripotassium phosphate and 20 mL of DMSO were added and stirred at 180° C. for 23 hours. After standing to cool to room temperature, 50 mL of pure water was added and stirred to precipitate a solid. The resulting solid was collected by filtration and recrystallized with a mixed solvent of toluene and butanol to give 4-(4-chlorophenyl)-9-(2-methyl-6-(naphthalen-2-yl)phenyl)-9H. -Carbazole (4.2 g (8.5 mmol) of white solid was isolated (yield 74%).

　Compounds were identified by FDMS measurement.

FDMS: 496
Synthetic Example 20 (9-([1,1′:4′,1″-terphenyl]-2′-yl)-4-(4′-chloro-[1,1′-biphenyl]-4-yl ) Synthesis of -9H-carbazole)

Under a nitrogen stream, 2.5 g (7.1 mmol) of 4-(4'-chloro-[1,1'-biphenyl]-4-yl)-9H-carbazole and 2'-fluoro-1 are placed in a 100 mL three-necked flask. ,1′:4′,1″-terphenyl 2.1 g (8.5 mmol), tripotassium phosphate 3.0 g (14 mmol) and DMSO 20 mL were added and stirred at 180° C. for 23 hours. After standing to cool to room temperature, 50 mL of pure water was added and stirred to precipitate a solid. The resulting solid was collected by filtration and recrystallized with a mixed solvent of toluene and butanol to give 9-([1,1′:4′,1″-terphenyl]-2′-yl)-4- (4'-Chloro-[1,1'-biphenyl]-4-yl)-9H-carbazole (3.2 g (5.6 mmol) of white solid was isolated (yield 79%).

　Compounds were identified by FDMS measurement.

FDMS: 581
Synthesis Example 21 (Synthesis of 4-(7-chloro-9,9-dimethyl-9H-fluoren-2-yl)-9-(2-(phenanthren-9-yl)phenyl)-9H-carbazole)

Under a nitrogen stream, 2.0 g (5.1 mmol) of 4-(7-chloro-9,9-dimethyl-9H-fluoren-2-yl)-9H-carbazole, 9-(2-fluoro 1.7 g (6.1 mmol) of phenyl)phenanthrene, 2.2 g (10 mmol) of tripotassium phosphate and 20 mL of DMSO were added and stirred at 180°C for 23 hours. After standing to cool to room temperature, 50 mL of pure water was added and stirred to precipitate a solid. The resulting solid was collected by filtration and recrystallized with a mixed solvent of toluene and butanol to give 4-(7-chloro-9,9-dimethyl-9H-fluoren-2-yl)-9-(2-( Phenanthren-9-yl)phenyl)-9H-carbazole (2.1 g (3.2 mmol) of white solid was isolated (64% yield).

　Compounds were identified by FDMS measurement.

FDMS: 645
Synthesis Example 22 (Synthesis of 4-(7-chloro-9,9-dimethyl-9H-fluoren-2-yl)-9-(2-(phenanthren-9-yl)phenyl)-9H-carbazole)

Under a nitrogen stream, 4.0 g (14 mmol) of 4-(4-chlorophenyl)-9H-carbazole obtained in Synthesis Example 7, 2-(2-fluorophenyl)-9,9-dimethyl- 5.0 g (17 mmol) of 9H-fluorene, 6.1 g (29 mmol) of tripotassium phosphate and 20 mL of DMSO were added and stirred at 180° C. for 23 hours. After standing to cool to room temperature, 50 mL of pure water was added and stirred to precipitate a solid. The resulting solid was collected by filtration and recrystallized with a mixed solvent of toluene and butanol to give 4-(4-chlorophenyl)-9-(2-(9,9-dimethyl-9H-fluoren-2-yl) Phenyl)-9H-carbazole (6.3 g (12 mmol) of white solid was isolated (yield 80%).

　Compounds were identified by FDMS measurement.

FDMS: 545

Example 1 (Synthesis of compound (F69))

Under a nitrogen stream, 2.1 g (7.7 mmol) of 2-chloro-9-phenyl-9H-carbazole and N-(2-(dibenzo[b,d]furan-4-yl)phenyl) are placed in a 100 mL three-necked flask. -[1,1'-biphenyl]-4-amine 3.0 g (7.3 mmol), sodium-tert-butoxide 0.91 g (9.5 mmol), xylene 20 mL, palladium acetate 16 mg (73 μmol) and tri(tert- 0.18 g (0.22 mmol) of a 25% by weight xylene solution of butyl)phosphine was added and stirred at 140° C. for 22 hours. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with a mixed solvent of toluene and butanol to isolate 3.6 g (5.5 mmol) of a white solid compound (F69) ( Yield 76%). The sublimation temperature of F69 was 300° C., and it was confirmed that the sublimated F69 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 727
Example 2 (Synthesis of compound (F98))

N-([1,1′:2′,1″:4″,1′″-quaterphenyl]-4″ obtained in Synthesis Example 1 was placed in a 100 mL three-necked flask under a nitrogen stream. '-yl)-9-(naphthalen-1-yl)-9H-carbazol-4-amine 2.3 g (3.8 mmol), 2-chloro-9-(2-(dibenzo[b,d]furan-4 -yl)phenyl)-9H-carbazole 1.7 g (3.8 mmol), sodium-tert-butoxide 0.43 g (4.5 mmol), xylene 20 mL, palladium acetate 8.4 mg (38 μmol) and tri(tert-butyl) ) 91 mg (0.11 mmol) of a 25% by weight xylene solution of phosphine was added and stirred at 140° C. for 24 hours. After allowing to cool to room temperature, 30 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with a mixed solvent of toluene and butanol to isolate 2.3 g (2.3 mmol) of a white solid compound (F98) ( Yield 61%). The sublimation temperature of F98 was 355° C., and it was confirmed that the sublimated F98 was glassy.
Compound identification was performed by FDMS measurement.

FDMS: 1019
Example 3 (Synthesis of compound (F103))

N,9-diphenyl-9H-carbazol-4-amine 3.1 g (9.3 mmol), 9-(4,4''-dimethyl-[1,1':4 ',1''-terphenyl]-2'-yl)-9H-carbazole 3.9 g (9.3 mmol), sodium-tert-butoxide 1.1 g (11 mmol), xylene 20 mL, palladium acetate 21 mg (93 μmol) And 0.23 g (0.28 mmol) of a 25% by weight xylene solution of tri(tert-butyl)phosphine was added and stirred at 140° C. for 16 hours. After allowing to cool to room temperature, 25 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with a mixed solvent of toluene and butanol to isolate 5.5 g (7.3 mmol) of a white solid compound (F103) ( Yield 79%). The sublimation temperature of F103 was 285° C., and it was confirmed that the sublimated F103 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 755
Example 4 (Synthesis of compound (F105))

1.6 g of N-(9,9-dimethylfluoren-2-yl)-N-(9-phenylcarbazol-2-yl)amine obtained in Synthesis Example 2 (3. 6 mmol), 2-chloro-9-(m-terphenyl-2-yl)carbazole 1.1 g (1.7 mmol), sodium-tert-butoxide 0.44 g (4.6 mmol), o-xylene 12 mL, palladium acetate 8.0 mg (36 μmol) and 86 mg (0.11 mmol) of a 25% by weight toluene solution of tri(tert-butyl)phosphine were added and stirred at 140° C. for 20 hours. After allowing to cool to room temperature, 32 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with a mixed solvent of toluene and butanol to isolate 2.1 g (2.5 mmol) of a yellow solid compound (F105) ( Yield 70%). The sublimation temperature of F105 was 300° C., and it was confirmed that the sublimated F105 was glassy.

FDMS: 844
Example 5 (Synthesis of compound (F108))

N-([1,1′:4′,1″-terphenyl]-2-yl)-9-(phenanthren-9-yl) obtained in Synthesis Example 3 was placed in a 100 mL three-necked flask under a nitrogen stream. -9H-carbazol-4-amine 2.0 g (3.4 mmol), 2-chloro-9-(2-phenylnaphthalen-1-yl)-9H-carbazole 1.4 g (3.4 mmol), sodium-tert- 0.39 g (4.1 mmol) of butoxide, 20 mL of xylene, 7.7 mg (34 μmol) of palladium acetate, and 83 mg (0.10 mmol) of a 25% by weight xylene solution of tri(tert-butyl)phosphine were added and the mixture was heated at 140°C for 22 hours. Stirred. After allowing to cool to room temperature, 30 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with a mixed solvent of toluene and butanol to isolate 2.4 g (2.5 mmol) of compound (F108) as a white solid ( Yield 73%). The sublimation temperature of F108 was 340° C., and it was confirmed that the sublimated F108 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 953
Example 6 (Synthesis of compound (F110))

Under a nitrogen stream, 9-([1,1′-biphenyl]-4-yl)-N-(4-phenylnaphthalen-1-yl)-9H-carbazole- 4-amine 1.6 g (3.0 mmol), 2-chloro-9-(1-phenylnaphthalen-2-yl)-9H-carbazole 1.2 g (3.0 mmol), sodium-tert-butoxide 0.34 g ( 3.6 mmol), 20 mL of xylene, 6.7 mg (30 μmol) of palladium acetate, and 72 mg (89 μmol) of a 25% by weight xylene solution of tri(tert-butyl)phosphine were added and stirred at 140° C. for 22 hours. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the obtained solid was recrystallized with a mixed solvent of toluene and butanol to isolate 1.7 g (1.9 mmol) of a white solid compound (F110) ( Yield 64%). The sublimation temperature of F110 was 340° C., and it was confirmed that the sublimated F110 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 903
Example 7 (Synthesis of compound (F112))

Under a nitrogen stream, 3.5 g (6.1 mmol) of N-(9,9-diphenyl-9H-fluoren-2-yl)-9-phenyl-9H-carbazol-4-amine, 2- Chloro-9-(4-methyl-[1,1'-biphenyl]-2-yl)-9H-carbazole 2.2 g (6.1 mmol), sodium-tert-butoxide 0.70 g (7.3 mmol), xylene 20 mL, 14 mg (61 μmol) of palladium acetate and 0.15 g (0.18 mmol) of a 25% by weight xylene solution of tri(tert-butyl)phosphine were added and stirred at 140° C. for 17 hours. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with a mixed solvent of toluene and butanol to isolate 4.8 g (5.3 mmol) of a white solid compound (F112) ( Yield 87%). The sublimation temperature of F112 was 315° C., and it was confirmed that the sublimated F112 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 905
Example 8 (Synthesis of compound (F132))

Under a nitrogen stream, 9-([1,1′-biphenyl]-2-yl)-N-(4-(dibenzo[b,d]furan-4-yl)phenyl)-9H- is placed in a 100 mL three-necked flask. Carbazol-4-amine 1.9 g (3.3 mmol), 9-([1,1':2',1''-terphenyl]-3'-yl)-2-chloro-9H-carbazole 1.4 g (3.3 mmol), 0.38 g (4.0 mmol) of sodium-tert-butoxide, 20 mL of xylene, 7.4 mg (33 μmol) of palladium acetate, and 80 mg (99 μmol) of a 25% by weight xylene solution of tri(tert-butyl)phosphine. and stirred at 140° C. for 22 hours. After allowing to cool to room temperature, 26 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the obtained solid was recrystallized with a mixed solvent of toluene and butanol to isolate 1.9 g (1.9 mmol) of a white solid compound (F132) ( Yield 58%). The sublimation temperature of F132 was 350° C., and it was confirmed that the sublimated F132 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 969
Example 9 (Synthesis of compound (F158))

Under a nitrogen stream, 4.7 g of N-(o-terphenyl-4'-yl)-N-(9-phenylcarbazol-2-yl)amine obtained in Synthesis Example 5 (9.0 g) was placed in a 100 mL three-necked flask. 7 mmol), 2-bromo-9-phenylcarbazole 3.3 g (10.2 mmol), sodium-tert-butoxide 1.21 g (12.6 mmol), o-xylene 32 mL, palladium acetate 22 mg (0.10 mmol), and tri 0.24 g (0.29 mmol) of a 25% by weight toluene solution of (tert-butyl)phosphine was added and stirred at 140° C. for 20 hours. After allowing to cool to room temperature, 32 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the obtained solid was recrystallized with a mixed solvent of toluene and butanol to isolate 4.2 g (5.8 mmol) of a yellow solid compound (F158) ( Yield 59%). The sublimation temperature of F158 was 325° C., and it was confirmed that the sublimated F158 was glassy. .

　Compounds were identified by FDMS measurement.

FDMS: 727
Example 10 (Synthesis of compound (F178))

Under a nitrogen stream, 2.0 g (5.2 mmol) of 4-chloro-9-(dibenzo[b,d]furan-4-yl)-9H-carbazole, 9-(dibenzo[b,d ]thiophen-4-yl)-N-(11,11-dimethyl-11H-benzo[a]fluoren-9-yl)-9H-carbazol-2-amine 3.2 g (5.2 mmol), sodium-tert- 0.60 g (6.3 mmol) of butoxide, 20 mL of xylene, 12 mg (52 μmol) of palladium acetate, and 0.13 g (0.16 mmol) of a 25% by weight xylene solution of tri(tert-butyl)phosphine are added and stirred at 140°C for 22 hours. bottom. After allowing to cool to room temperature, 25 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the obtained solid was recrystallized with a mixed solvent of toluene and butanol to isolate 2.4 g (2.6 mmol) of a white solid compound (F178) ( Yield 49%). The sublimation temperature of F178 was 320° C., and it was confirmed that the sublimated F178 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 937
Example 11 (Synthesis of compound (G27))

Under a nitrogen stream, 3.0 g (7.0 mmol) of 9-([1,1′:2′,1″-terphenyl]-3′-yl)-2-chloro-9H-carbazole is placed in a 100 mL three-necked flask. ), 9-(naphthalen-1-yl)-N-(triphenylen-1-yl)-9H-carbazol-2-amine 3.7 g (7.0 mmol), sodium-tert-butoxide 0.80 g (8.4 mmol ), 20 mL of xylene, 16 mg (70 μmol) of palladium acetate and 0.17 g (0.21 mmol) of a 25% by weight xylene solution of tri(tert-butyl)phosphine were added and stirred at 140° C. for 22 hours. After allowing to cool to room temperature, 30 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Next, the solvent was distilled off under reduced pressure, and the obtained solid was recrystallized with a mixed solvent of toluene and butanol to isolate 4.5 g (4.8 mmol) of a white solid compound (G27) ( Yield 69%). The sublimation temperature of G27 was 335° C., and it was confirmed that the sublimated G27 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 927
Example 12 (Synthesis of compound (G33))

Under a nitrogen stream, 2.9 g (6.7 mmol) of 9-([1,1′:3′,1″-terphenyl]-2′-yl)-2-chloro-9H-carbazole is placed in a 100 mL three-necked flask. ), N-([1,1′:2′,1″-terphenyl]-4′-yl)-9-phenyl-9H-carbazol-2-amine 3.3 g (6.7 mmol), sodium- 0.78 g (8.1 mmol) of tert-butoxide, 20 mL of xylene, 15 mg (67 μmol) of palladium acetate, and 0.16 g (0.20 mmol) of a 25% by weight xylene solution of tri(tert-butyl)phosphine were added and heated at 140°C. Stirred for 22 hours. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the obtained solid was recrystallized with a mixed solvent of toluene and butanol to isolate 4.7 g (5.4 mmol) of a white solid compound (G33) ( Yield 80%). The sublimation temperature of G33 was 320° C., and it was confirmed that the sublimated G33 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 879
Example 13 (Synthesis of compound (G64))

Under a nitrogen stream, 0.80 g (8.6 mmol) of aniline, 8.1 g (19 mmol) of 2-chloro-9-(m-terphenyl-2-yl)carbazole, and 2 sodium-tert-butoxide are placed in a 100 mL three-necked flask. .5 mg (21 mmol), 29 mL of xylene, 39 mg (0.17 mmol) of palladium acetate, and 0.42 mg (0.52 mmol) of a 25% by weight toluene solution of tri(tert-butyl)phosphine were added and stirred at 140°C for 20 hours. . After allowing to cool to room temperature, 29 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with a mixed solvent of toluene and butanol to isolate 6.4 g (7.2 mmol) of a white solid compound (G64) ( Yield 68%). The sublimation temperature of G64 was 320° C., and it was confirmed that the sublimated G64 was glassy.

FDMS: 879
Example 14 (Synthesis of compound (G72))

Under a nitrogen stream, 5.0 g (12 mmol) of 9-([1,1′:3′,1″-terphenyl]-2′-yl)-2-chloro-9H-carbazole are placed in a 100 mL three-necked flask, 3,5-dimethylaniline 0.49 g (5.3 mmol), sodium-tert-butoxide 1.2 g (12 mmol), xylene 20 mL, palladium acetate 12 mg (53 μmol) and tri(tert-butyl)phosphine in 25 wt% xylene 0.13 g (0.16 mmol) of the solution was added and stirred at 140°C for 22 hours. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the obtained solid was recrystallized with a mixed solvent of toluene and butanol to isolate 4.0 g (4.5 mmol) of a white solid compound (G72) ( Yield 85%). The sublimation temperature of G72 was 285° C., and it was confirmed that the sublimated G72 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 908
Example 15 (Synthesis of compound (G88))

Under a nitrogen stream, 5.1 g (14 mmol) of 9-([1,1′-biphenyl]-2-yl)-2-chloro-9H-carbazole, 4-(9H-carbazole-9- yl)aniline 1.7 g (6.6 mmol), sodium-tert-butoxide 1.5 g (16 mmol), xylene 20 mL, palladium acetate 15 mg (66 μmol), and 25% by weight xylene solution of tri(tert-butyl)phosphine 0.16 g (0.20 mmol) was added and stirred at 140° C. for 22 hours. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the obtained solid was recrystallized with a mixed solvent of toluene and butanol to isolate 5.3 g (5.9 mmol) of a white solid compound (G88) ( Yield 90%). The sublimation temperature of G88 was 340° C., and it was confirmed that the sublimated G88 was glassy.

FDMS: 892
Example 16 (Synthesis of compound (G129))

N,9-diphenyl-9H-carbazol-2-amine 2.0 g (6.0 mmol), 9-(2-(9H-carbazol-9-yl)-6-methyl Phenyl)-2-chloro-9H-carbazole 2.7 g (6.0 mmol), sodium-tert-butoxide 0.69 g (7.2 mmol), xylene 20 mL, palladium acetate 13 mg (60 μmol) and tri(tert-butyl)phosphine 0.15 g (0.18 mmol) of a 25% by weight xylene solution of was added and stirred at 140° C. for 22 hours. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with a mixed solvent of toluene and butanol to isolate 3.4 g (4.5 mmol) of compound (G129) as a white solid ( Yield 75%). The sublimation temperature of G129 was 310° C., and it was confirmed that the sublimated G129 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 754
Example 17 (Synthesis of compound (G134))

Under a nitrogen stream, 4.5 g (10 mmol) of 9-([1,1′:2′,1″-terphenyl]-4′-yl)-2-chloro-9H-carbazole are placed in a 100 mL three-necked flask, Phenanthrene-9-amine 0.96 g (5.0 mmol), sodium-tert-butoxide 1.1 g (12 mmol), xylene 20 mL, palladium acetate 11 mg (50 μmol), and 25 wt% xylene solution of tri(tert-butyl)phosphine 0 .12 g (0.15 mmol) was added and stirred at 140° C. for 22 hours. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with a mixed solvent of toluene and butanol to isolate 4.2 g (4.3 mmol) of compound (G134) as a white solid ( Yield 86%). The sublimation temperature of G134 was 315° C., and it was confirmed that the sublimated G134 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 979
Example 18 (Synthesis of compound (G142))

Under a nitrogen stream, 4.4 g of 2-chloro-9-(2-(naphthalen-2-yl)-[1,1′-biphenyl]-3-yl)-9H-carbazole (9.4 g of 2-chloro-9-(2-(naphthalen-2-yl)-[1,1′-biphenyl]-3-yl)-9H-carbazole was placed in a 100 mL three-necked flask. 2 mmol), 6-phenylnaphthalen-2-amine 0.96 g (4.4 mmol), sodium-tert-butoxide 0.93 g (9.7 mmol), xylene 20 mL, palladium acetate 9.9 mg (44 μmmol) and tri(tert- 0.11 g (0.13 mmol) of a 25% by weight xylene solution of butyl)phosphine was added and stirred at 140° C. for 22 hours. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the obtained solid was recrystallized with a mixed solvent of toluene and butanol to isolate 3.4 g (3.1 mmol) of a white solid compound (G142) ( Yield 70%). The sublimation temperature of G142 was 340° C., and it was confirmed that the sublimated G142 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 1106
Example 19 (Synthesis of compound (G148))

Under a nitrogen stream, 5.0 g (12 mmol) of 9-([1,1′:3′,1″-terphenyl]-4′-yl)-2-chloro-9H-carbazole are placed in a 100 mL three-necked flask, Dibenzo[b,d]thiophen-4-amine 1.1 g (5.5 mmol), sodium-tert-butoxide 1.2 g (12 mmol), xylene 20 mL, palladium acetate 12 mg (55 μmmol) and tri(tert-butyl)phosphine 0.13 g (0.16 mmol) of a 25% by weight xylene solution was added and stirred at 140° C. for 26 hours. After allowing to cool to room temperature, 40 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the obtained solid was recrystallized with a mixed solvent of toluene and butanol to isolate 4.0 g (4.0 mmol) of a white solid compound (G148) ( Yield 73%). The sublimation temperature of G148 was 335° C., and it was confirmed that the sublimated G148 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 986
Example 20 (Synthesis of compound (G161))

Under a nitrogen stream, 3.0 g of 2-chloro-9-(3-(naphthalen-2-yl)-[1,1'-biphenyl]-2-yl)-9H-carbazole (6. 2 mmol), 9,9′-spiro bi[fluorene]-2-amine 1.0 g (3.1 mmol), sodium-tert-butoxide 0.66 g (6.8 mmol), xylene 20 mL, palladium acetate 7.0 g (31 μmmol) ) and 75 mg (93 μmmol) of a 25% by weight xylene solution of tri(tert-butyl)phosphine were added and stirred at 140° C. for 22 hours. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the obtained solid was recrystallized with a mixed solvent of toluene and butanol to isolate 3.4 g (2.7 mmol) of a white solid compound (G161) ( Yield 88%). The sublimation temperature of G161 was 345° C., and it was confirmed that the sublimated G161 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 1217
Example 21 (Synthesis of compound (G167))

Under a nitrogen stream, 3.0 g (2.8.2 mmol) of 2-chloro-9-(dibenzo[b,d]furan-4-yl)-4-chloro-9H-carbazole, 4- (Naphthalen-1-yl)aniline 0.81 g (3.7 mmol), sodium-tert-butoxide 0.78 g (8.1 mmol), xylene 20 mL, palladium acetate 8.3 mg (37 μmol) and tri(tert-butyl)phosphine 90 mg (0.11 mmol) of a 25% by weight xylene solution of was added and stirred at 140° C. for 22 hours. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Next, the solvent was distilled off under reduced pressure, and the obtained solid was recrystallized with a mixed solvent of toluene and butanol to isolate 2.5 g (2.9 mmol) of a white solid compound (G167) ( Yield 77%). The sublimation temperature of G167 was 325° C., and it was confirmed that the sublimated G167 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 881
Example 22 (Synthesis of compound (H7))

9-([1,1′:4′,1″-terphenyl]-2-yl)-3-(4-chlorophenyl)- 9H-carbazole 2.8 g (5.5 mmol), N-([1,1'-biphenyl]-4-yl)-[1,1':2',1''-terphenyl]-4'-amine 2.1 g (5.3 mmol), sodium-tert-butoxide 0.76 g (7.9 mmol), xylene 20 mL, palladium acetate 12 mg (53 μmol) and tri(tert-butyl)phosphine 25% by weight xylene solution 0.13 g ( 0.16 mmol) was added and stirred at 140° C. for 22 hours. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Next, the solvent was distilled off under reduced pressure, and the obtained solid was recrystallized with a mixed solvent of toluene and butanol to isolate 3.6 g (4.2 mmol) of a white solid compound (H7) ( Yield 79%). The sublimation temperature of H7 was 310° C., and it was confirmed that the sublimated H7 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 866
Example 23 (Synthesis of compound (H124))

Under a nitrogen stream, 9-([1,1′:3′,1″-terphenyl]-4′-yl)-3-(4-chlorophenyl) obtained in Synthesis Example 9 was placed in a 100 mL three-necked flask. -9H-carbazole 2.5 g (4.9 mmol), N-([1,1'-biphenyl]-4-yl)naphthalen-1-amine 1.8 g (5.9 mmol), sodium-tert-butoxide 0. 57 g (5.9 mmol), 20 mL of xylene, 11 mg (49 μmol) of palladium acetate, and 0.12 g (0.15 mmol) of a 25% by weight xylene solution of tri(tert-butyl)phosphine were added and stirred at 140° C. for 22 hours. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with a mixed solvent of toluene and butanol to isolate 3.1 g (4.0 mmol) of a white solid compound (H124) ( Yield 81%). The sublimation temperature of H124 was 300° C., and it was confirmed that the sublimated H124 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 764
Example 24 (Synthesis of compound (H144))

Under a nitrogen stream, 5.0 g (9.1 mmol) of 3-(4-chlorophenyl)-9-(m-terphenyl-2′-yl)carbazole obtained in Synthesis Example 10 was placed in a 100 mL three-necked flask, N, N-bis(biphenyl-4-yl)amine 2.7 g (8.3 mmol), sodium-tert-butoxide 1.0 g (11 mmol), o-xylene 28 mL, palladium acetate 19 mg (83 μmmol), and tri(tert-butyl ) 0.20 g (0.25 mmol) of a 25% by weight toluene solution of phosphine was added and stirred at 140°C for 20 hours. After standing to cool to room temperature, 20 mL of pure water was added and stirred to precipitate a solid. The resulting solid was collected by filtration and recrystallized with a mixed solvent of toluene and butanol to isolate 4.9 g (6.2 mmol) of compound (H144) as a white solid (yield 75%). The sublimation temperature of H144 was 340° C., and it was confirmed that the sublimated H144 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 790
Example 25 (Synthesis of compound (H290))

3-(4-chlorophenyl)-9-(2-(dibenzo[b,d]furan-2-yl)phenyl)-9H-carbazole 2 obtained in Synthesis Example 11 was added to a 100 mL three-necked flask under a nitrogen stream. .5 g (4.8 mmol), N-phenyl-9,9'-spirobi[fluorene]-4-amine 1.9 g (4.6 mmol), sodium-tert-butoxide 0.53 g (5.5 mmol), xylene 20 mL , 10 mg (46 μmol) of palladium acetate and 0.11 g (0.14 mmol) of a 25% by weight xylene solution of tri(tert-butyl)phosphine were added and stirred at 140° C. for 22 hours. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the obtained solid was recrystallized with a mixed solvent of toluene and butanol to isolate 2.5 g (2.8 mmol) of a white solid compound (H290) ( Yield 61%). The sublimation temperature of H290 was 320° C., and it was confirmed that the sublimated H290 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 890
Example 26 (Synthesis of compound (H299))

2.0 g of 3-(4-chlorophenyl)-9-(2,6-di(naphthalen-1-yl)phenyl)-9H-carbazole obtained in Synthesis Example 12 ( 3.3 mmol), N-([1,1'-biphenyl]-4-yl)-9,9-dimethyl-9H-fluoren-2-amine 1.1 g (3.1 mmol), sodium-tert-butoxide 0 .36 g (3.7 mmol), 20 mL of xylene, 7.0 mg (31 μmol) of palladium acetate, and 76 mg (93 μmol) of a 25% by weight xylene solution of tri(tert-butyl)phosphine were added and stirred at 140° C. for 22 hours. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with a mixed solvent of toluene and butanol to isolate 2.5 g (2.7 mmol) of a white solid compound (H299) ( Yield 87%). The sublimation temperature of H299 was 300° C., and it was confirmed that the sublimated H299 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 930
Example 27 (Synthesis of compound (H322))

Under a nitrogen stream, 9-([1,1′:4′,1″-terphenyl]-2′-yl)-3-(4-chloronaphthalene obtained in Synthesis Example 13 was placed in a 100 mL three-necked flask. -1-yl)-9H-carbazole 2.0 g (3.6 mmol), N-([1,1'-biphenyl]-4-yl)pyren-1-amine 1.3 g (3.4 mmol), sodium- 0.39 g (4.1 mmol) of tert-butoxide, 20 mL of xylene, 7.7 mg (34 μmol) of palladium acetate, and 83 mg (0.10 mmol) of a 25% by weight xylene solution of tri(tert-butyl)phosphine were added and Stirred for an hour. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with a mixed solvent of toluene and butanol to isolate 1.5 g (1.7 mmol) of a white solid compound (H322) ( 50% yield). The sublimation temperature of H322 was 335° C., and it was confirmed that the sublimated H322 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 888
Example 28 (Synthesis of compound (H335))

Under a nitrogen stream, 2.1 g of 3-(4-chlorophenyl)-9-(2-methyl-6-(naphthalen-2-yl)phenyl)-9H-carbazole obtained in Synthesis Example 14 was placed in a 100 mL three-necked flask. (4.3 mmol), N-phenyl-[1,1'-biphenyl]-4-amine 1.0 g (4.3 mmol), sodium-tert-butoxide 0.49 g (5.1 mmol), xylene 20 mL, palladium acetate 9.5 mg (43 μmol) and 0.10 g (0.13 mmol) of a 25% by weight xylene solution of tri(tert-butyl)phosphine were added and stirred at 140° C. for 22 hours. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the obtained solid was recrystallized with a mixed solvent of toluene and butanol to isolate 1.9 g (2.7 mmol) of a white solid compound (H335) ( Yield 63%). The sublimation temperature of H335 was 290° C., and it was confirmed that the sublimated H335 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 702
Example 29 (Synthesis of compound (I18))

Under a nitrogen stream, 9-([1,1′:4′,1″-terphenyl]-2-yl)-4-(4-chlorophenyl) obtained in Synthesis Example 15 was placed in a 100 mL three-necked flask. -9H-carbazole 2.2 g (4.3 mmol), N-(4-(9H-carbazol-9-yl)phenyl)naphthalene-2-amine 1.6 g (4.1 mmol), sodium-tert-butoxide 0. 48 g (5.0 mmol), 20 mL of xylene, 9.3 mg (41 μmol) of palladium acetate, and 0.10 g (0.12 mmol) of a 25% by weight xylene solution of tri(tert-butyl)phosphine were added and stirred at 140° C. for 22 hours. . After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with a mixed solvent of toluene and butanol to isolate 2.8 g (3.3 mmol) of compound (I18) as a white solid ( Yield 80%). The sublimation temperature of I18 was 345° C., and it was confirmed that the sublimated I18 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 854
Example 30 (Synthesis of compound (I125))

Under a nitrogen stream, 9-([1,1′:2′,1″-terphenyl]-3′-yl)-4-(4-chlorophenyl )-9H-carbazole 3.0 g (5.9 mmol), di([1,1'-biphenyl]-4-yl)amine 1.9 g (5.9 mmol), sodium-tert-butoxide 0.68 g (7. 1 mmol), 20 mL of xylene, 13 mg (59 μmol) of palladium acetate, and 0.14 g (0.18 mmol) of a 25% by weight xylene solution of tri(tert-butyl)phosphine were added and stirred at 140° C. for 22 hours. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with a mixed solvent of toluene and butanol to isolate 3.8 g (4.8 mmol) of compound (I125) as a white solid ( Yield 81%). The sublimation temperature of I125 was 320° C., and it was confirmed that the sublimated I125 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 791
Example 31 (Synthesis of Compound (I131))

Under a nitrogen stream, 9-([1,1′:3′,1″-terphenyl]-4′-yl)-4-(4-chlorophenyl )-9H-carbazole 3.1 g (6.1 mmol), N-phenyl-[1,1′:4′,1″-terphenyl]-4-amine 2.0 g (6.1 mmol), sodium-tert 0.71 g (7.4 mmol) of -butoxide, 20 mL of xylene, 14 mg (61 μmol) of palladium acetate, and 0.15 g (0.18 mmol) of a 25% by weight xylene solution of tri(tert-butyl)phosphine were added, and the mixture was heated at 140°C for 22 hours. Stirred. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with a mixed solvent of toluene and butanol to isolate 3.6 g (4.6 mmol) of compound (I131) as a white solid ( Yield 75%). The sublimation temperature of I131 was 330° C., and it was confirmed that the sublimated I131 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 791
Example 32 (Synthesis of compound (I293))

4-(4-chlorophenyl)-9-(2-(dibenzo[b,d]thiophene- 2-yl)phenyl)-9H-carbazole 2.6 g (4.8 mmol), N-([1,1'-biphenyl]-4-yl)-7,7-dimethyl-7H-benzo[c]fluorene- 5-amine 2.0 g (4.8 mmol), sodium-tert-butoxide 0.56 g (5.8 mmol), xylene 20 mL, palladium acetate 11 mg (48 μmol), and 25 wt% xylene solution of tri(tert-butyl)phosphine 0 .12 g (0.15 mmol) was added and stirred at 140° C. for 22 hours. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with a mixed solvent of toluene and butanol to isolate 3.0 g (3.3 mmol) of compound (I293) as a white solid ( Yield 69%). The sublimation temperature of I293 was 320° C., and it was confirmed that the sublimated I293 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 910
Example 33 (Synthesis of compound (I313))

4-(4-chlorophenyl)-9-(2-methyl-6-(naphthalen-2-yl)phenyl)-9H-carbazole obtained in Synthesis Example 19 was added to a 100 mL three-necked flask under a nitrogen stream2. 8 g (5.7 mmol), bis(9,9-dimethyl-9H-fluoren-2-yl)amine 2.3 g (5.7 mmol), sodium-tert-butoxide 0.65 g (6.8 mmol), xylene 20 mL, 13 mg (57 μmol) of palladium acetate and 0.14 g (0.17 mmol) of a 25% by weight xylene solution of tri(tert-butyl)phosphine were added and stirred at 140° C. for 22 hours. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with a mixed solvent of toluene and butanol to isolate 3.9 g (4.6 mmol) of compound (I313) as a white solid ( Yield 81%). The sublimation temperature of I313 was 310° C., and it was confirmed that the sublimated I313 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 859
Example 34 (Synthesis of compound (I321))

Under a nitrogen stream, 9-([1,1′:4′,1″-terphenyl]-2′-yl)-4-(4′- Chloro-[1,1'-biphenyl]-4-yl)-9H-carbazole 2.4 g (4.1 mmol), N-([1,1'-biphenyl]-2-yl)triphenylene-2-amine 1 .6 g (4.1 mmol), 0.48 g (4.9 mmol) of sodium-tert-butoxide, 20 mL of xylene, 9.3 mg (41 μmol) of palladium acetate, and 0.10 g of a 25% by weight xylene solution of tri(tert-butyl)phosphine (0.12 mmol) was added and stirred at 140° C. for 22 hours. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with a mixed solvent of toluene and butanol to isolate 2.3 g (2.4 mmol) of compound (I321) as a white solid ( Yield 58%). The sublimation temperature of I321 was 335° C., and it was confirmed that the sublimated I321 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 940
Example 35 (Synthesis of compound (I323))

4-(7-chloro-9,9-dimethyl-9H-fluoren-2-yl)-9-(2-(phenanthrene-9- yl)phenyl)-9H-carbazole 1.9 g (2.9 mmol), bis(dibenzo[b,d]furan-4-yl)amine 1.0 g (2.9 mmol), sodium-tert-butoxide 0.34 g ( 3.5 mmol), 20 mL of xylene, 6.6 mg (29 μmol) of palladium acetate, and 71 mg (88 μmol) of a 25% by weight xylene solution of tri(tert-butyl)phosphine were added and stirred at 140° C. for 22 hours. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with a mixed solvent of toluene and butanol to isolate 1.6 g (1.6 mmol) of compound (I323) as a white solid ( Yield 56%). The sublimation temperature of I323 was 330° C., and it was confirmed that the sublimated I323 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 958
Example 36 (Synthesis of compound (I334))

Under a nitrogen stream, 4-(4-chlorophenyl)-9-(2-(9,9-dimethyl-9H-fluoren-2-yl)phenyl)-9H obtained in Synthesis Example 22 was placed in a 100 mL three-necked flask. -carbazole 3.5 g (6.4 mmol), N-(naphthalen-2-yl)anthracen-9-amine 2.0 g (6.4 mmol), sodium-tert-butoxide 0.74 g (7.7 mmol), xylene 20 mL , 14 mg (64 μmol) of palladium acetate and 0.16 g (0.19 mmol) of a 25% by weight xylene solution of tri(tert-butyl)phosphine were added and stirred at 140° C. for 22 hours. After allowing to cool to room temperature, 22 mL of pure water was added and stirred. Then, the aqueous layer and the organic layer were separated, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then subjected to column chromatography using a small amount of silica gel to remove highly polar components. Then, the solvent was distilled off under reduced pressure, and the resulting solid was recrystallized with a mixed solvent of toluene and butanol to isolate 3.9 g (4.7 mmol) of compound (I334) as a white solid ( Yield 74%). The sublimation temperature of I334 was 320° C., and it was confirmed that the sublimated I334 was glassy.

　Compounds were identified by FDMS measurement.

FDMS: 828
Example 37 (Lateral current evaluation of compound (F69))
A glass substrate on which a comb-shaped ITO electrode with a thickness of 160 nm is formed is used to measure the transverse current. Two comb-shaped ITO electrodes having a width of 20 μm and a length of 2 mm are formed on the glass substrate. The gap between the two comb-shaped electrodes is arranged to be 80 μm.

The above glass substrate was subjected to ultrasonic cleaning with ultrapure water. Surface treatment was performed by ozone ultraviolet cleaning. The glass substrate was introduced into a vacuum deposition tank, and the pressure was reduced to 1.0×10 ⁻⁴ Pa by a vacuum pump. Then, each layer was produced in the following order according to the film forming conditions of each layer. In addition, each organic material was formed into a film by a resistance heating method.
(Preparation of hole injection layer)
The compound (F69) purified by sublimation in Example 1 and 1,2,3-tris[(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane were mixed at 99:1 (mass A film of 10 nm was formed at a ratio of ) to prepare a hole injection layer.
(Preparation of hole transport layer)
The compound (F69) purified by sublimation in Example 1 was deposited at a rate of 0.2 nm/sec to form a film having a thickness of 100 nm to prepare a hole transport layer.

Under a nitrogen atmosphere, a sealing glass plate was adhered with a UV curable resin to form a lateral current evaluation element. A voltage of 20 V was applied between the comb-shaped electrodes of the device thus produced, and the flowing current was measured as a transverse current. Table 1 shows the results.

Examples 38-72 (Lateral Current Evaluation of Compounds (F98)-(I334))
A lateral current evaluation element was produced in the same manner as in Example 37, except that the compounds (F98)-(I334) purified by sublimation in Example 2-34 were used instead of the compound (F69). Table 1 shows the lateral current measured by the same method as in Example 37 for the lateral current evaluation element.

Comparative Example 1-8 (Synthesis of Compounds (a)-(h), Lateral Current Evaluation)
Compounds (a) to (h), which are known compounds, were synthesized and purified by sublimation.

A lateral current evaluation element was produced in the same manner as in Example 37, except that compounds (a)-(h) were used instead of compound (F69). Table 1 shows the lateral current measured by the same method as in Example 36 for the lateral current evaluation element.

[Example of organic electroluminescence element]
The structural formulas and abbreviations of the compounds used in the production of the organic electroluminescence device are shown below.

Example 73 (Device evaluation of compound (F105))
A glass substrate with an ITO transparent electrode, on which an indium-tin oxide (ITO) film (thickness: 110 nm) with a width of 2 mm was patterned in stripes, was prepared. Then, after washing the substrate with isopropyl alcohol, the surface was treated by ozone ultraviolet washing. The glass substrate was introduced into a vacuum deposition tank, and the pressure was reduced to 1.0×10 −4 Pa. Then, each layer was produced in the following order according to the film forming conditions of each layer.

(Preparation of hole injection layer)
Compound (F105) and 1,2,3-tris[(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane were deposited at a ratio of 99:1 (mass ratio) to form a 10 nm film. , to prepare a hole injection layer.

(Preparation of hole transport layer)
A 100 nm film of compound (F105) was formed at a rate of 0.2 nm/sec to prepare a hole transport layer.

(Preparation of electron blocking layer)
EBL was deposited to a thickness of 5 nm at a rate of 0.15 nm/sec to form an electron blocking layer.

(Preparation of light-emitting layer)
HOST and DOPANT were deposited at a ratio of 95:5 (mass ratio) to a thickness of 20 nm to form a light-emitting layer. The deposition rate was 0.18 nm/sec.

(Preparation of electron transport layer)
HBL was deposited to a thickness of 6 nm at a rate of 0.05 nm/sec to form a first electron transport layer.

(Preparation of electron injection layer)
ETL and Liq were deposited at a ratio of 50:50 (mass ratio) to a thickness of 25 nm to form a second electron transport layer. The deposition rate was 0.15 nm/sec.

(Preparation of cathode)
Finally, a metal mask was placed perpendicular to the ITO stripes on the substrate, and a cathode was formed. The cathode was formed by depositing ytterbium, silver/magnesium (mass ratio 9/1), and silver in this order to thicknesses of 2 nm, 12 nm, and 90 nm, respectively, to form a three-layer structure. The deposition rate of ytterbium was 0.02 nm/second, the deposition rate of silver/magnesium was 0.5 nm/second, and the deposition rate of silver was 0.2 nm/second.

Thus, an organic electroluminescence element with a light emitting area of 4 mm2 was produced.

Furthermore, this device was sealed in a nitrogen atmosphere glove box with an oxygen and moisture concentration of 1 ppm or less. Sealing was performed by using a UV curable epoxy resin (manufactured by Moresco) between the glass sealing cap and the film formation substrate (element).

A current of 10 mA/cm2 was applied to the device thus produced, and the voltage and luminous efficiency were measured. Table 2 shows the results.

Examples 74-76 (element evaluation of compounds (G64) to (I131))
An organic electroluminescence device was produced in the same manner as in Example 73, except that compounds (G64) to (I131) were used instead of compound (F105). Table 2 shows the results.

Comparative Examples 9 to 12 (Compound (e), compound (i) to compound (k) element evaluation)
Compound (e) and compounds (i) to (k), which are known compounds, were synthesized and purified by sublimation.

An organic electroluminescence device was produced in the same manner as in Example 73, except that compound (e) and compounds (i) to (k) were used instead of compound (F105). Table 2 shows the results.

Although the present invention has been described in detail and with reference to specific embodiments, it will be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the invention.

In addition, Japanese Patent Application No. 2021-127012 filed on August 2, 2021, and Japanese Patent Application No. 2021-196537 filed on December 2, 2021, and filed on August 24, 2021 The entire contents of the specification, claims, drawings and abstract of Japanese Patent Application No. 2021-136716 are hereby incorporated into the disclosure of the specification of the present invention.

100: Organic electroluminescence device containing the compound of the present invention 1: Substrate 2: Anode 3: Hole injection layer 4: Hole transport layer 5: Electron blocking layer 6: Emitting layer 7: Electron transport layer 8: Electron injection layer 9 :cathode

Claims

Amine compounds represented by formulas (1) to (3):

In formulas (1) to (3),
R 1 to R 4 are each independently;
hydrogen atom, deuterium atom, cyano group, linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, linear, branched or cyclic alkoxy group having 1 to 18 carbon atoms, optionally substituted carbon number 6 to 25 monocyclic, linked or condensed aromatic hydrocarbon groups, or
It is an optionally substituted monocyclic, linked or condensed heteroaromatic group having 3 to 25 carbon atoms.
R5 and R6 are hydrogen.
L 1 to L 5 are each independently;
one substituent selected from the group consisting of a linear, branched, or cyclic alkyl group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, a deuterium atom, and a cyano group; a monocyclic, linked or condensed divalent aromatic hydrocarbon group having 6 to 25 carbon atoms which may have more than
an optionally substituted monocyclic, linked or condensed divalent heteroaromatic group having 3 to 25 carbon atoms, or
It is a single bond.
L6 represents a single bond.
X 1 and X 2 are each independently;
one substituent selected from the group consisting of a linear, branched, or cyclic alkyl group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, a deuterium atom, and a cyano group; A monocyclic, linked, or condensed divalent aromatic hydrocarbon group having 6 to 25 carbon atoms which may have more than, or
an optionally substituted monocyclic, linked or condensed divalent heteroaromatic group having 3 to 25 carbon atoms;
X3 is a single bond.
B represents any group represented by the following chemical formula (4) or (5).

In formulas (1) to (5),
Ar 2 , Ar 3 and Ar 5 to Ar 10 are each independently;
linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, linear, branched or cyclic alkoxy group having 1 to 18 carbon atoms, deuterium atom, cyano group, phenyl group, biphenylyl group, naphthyl group, phenanthryl group , a monocyclic ring having 6 to 25 carbon atoms optionally having one or more substituents selected from the group consisting of a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group, linked, or a condensed aromatic hydrocarbon group, or a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, a linear, branched or cyclic alkoxy group having 1 to 18 carbon atoms, a deuterium atom, a cyano group, It may have one or more substituents selected from the group consisting of a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylenyl group, a triphenylsilyl group, a carbazolyl group, a dibenzothienyl group, and a dibenzofuranyl group. It represents a monocyclic, linked or condensed heteroaromatic group having 3 to 25 carbon atoms.
Ar 1 and Ar 4 are each independently one selected from groups represented by the following general formulas (6) to (14),
When B in formula (3) is represented by formula (4), at least one of Ar 7 , Ar 8 and Ar 9 is each independently represented by general formulas (6) to (16) above. is one selected from the groups
When B in formula (3) is represented by formula (5), at least one of Ar 7 , Ar 8 and Ar 10 is each independently represented by general formulas (6) to (16) above. is one selected from the groups

In formulas (6) to (16),
R 7 is;
a hydrogen atom, a deuterium atom, a cyano group, a linear, branched or cyclic alkyl group having 1 to 18 carbon atoms, or a linear, branched or cyclic alkoxy group having 1 to 18 carbon atoms;
Ar 11 is;
an optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 10 to 25 carbon atoms, or
an optionally substituted monocyclic, linked or condensed heteroaromatic group having 3 to 25 carbon atoms;
Ar 12 and Ar 13 are each independently;
an optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 25 carbon atoms, or
an optionally substituted monocyclic, linked or condensed heteroaromatic group having 3 to 25 carbon atoms;
L7 is;
an optionally substituted monocyclic, linked or condensed divalent aromatic hydrocarbon group having 6 to 25 carbon atoms, or
It is an optionally substituted monocyclic, linked or condensed divalent heteroaromatic group having 3 to 25 carbon atoms.
L 8 is;
an optionally substituted monocyclic, linked or condensed divalent aromatic hydrocarbon group having 6 to 25 carbon atoms,
an optionally substituted monocyclic, linked or condensed divalent heteroaromatic group having 3 to 25 carbon atoms, or
It is a single bond.
Y is an oxygen atom or a sulfur atom.
Ar 2 , Ar 3 and Ar 5 to Ar 10 are each independently
(i) phenyl group, biphenylyl group, terphenylyl group, naphthyl group, fluorenyl group, spirobifluorenyl group, benzofluorenyl group, phenanthryl group, fluoranthenyl group, triphenylenyl group, anthryl group, pyrenyl group, carbazolyl group; , a dibenzofuranyl group, or a dibenzothienyl group, or
(ii) the group represented by (i) is a methyl group, an ethyl group, a methoxy group, an ethoxy group, a cyano group, a deuterium atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a triphenylsilyl group, or a carbazolyl; 2. The amine compound according to claim 1, which is a group substituted with one or more groups selected from the group consisting of a group, a dibenzothienyl group, and a dibenzofuranyl group.
L 1 to L 4 are each independently
a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, or a single bond which may have one or more substituents selected from the group consisting of a methyl group, a methoxy group, a cyano group, a deuterium atom, and a phenyl group; The amine compound according to claim 1, wherein
X 1 and X 2 are each independently
A phenylene group optionally having one or more substituents selected from the group consisting of a methyl group, a methoxy group, a cyano group, a deuterium atom, and a phenyl group, a biphenylene group, a terphenylene group, a naphthylene group, and a fluorene-diyl spirobifluorene-diyl group, phenanthrene-diyl group, triphenylene-diyl group, carbazole-diyl group, dibenzofuran-diyl group, or dibenzothiophene-diyl group.
Ar 11 is
A biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluore which optionally has one or more substituents selected from the group consisting of a methyl group, a methoxy group, a cyano group, a deuterium atom, and a phenyl group 2. The amine compound according to claim 1, which is a nyl group, a phenanthryl group, a triphenylenyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothienyl group.
Ar 12 and Ar 13 are each independently
A phenyl group optionally having one or more substituents selected from the group consisting of a methyl group, a methoxy group, a cyano group, a deuterium atom, and a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spiro 2. The amine compound according to claim 1, which is a bifluorenyl group, a phenanthryl group, a triphenylenyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothienyl group.
In formula (3), B is represented by formula (4), and at least one of Ar 7 and Ar 9 is each independently selected from groups represented by general formulas (6) to (16). The amine compound according to claim 1, which is one.
In formula (3), B is represented by formula (5), and at least one of Ar 7 and Ar 10 is each independently selected from groups represented by general formulas (6) to (16). The amine compound according to claim 1, which is one.
In formula (3), B is represented by formula (5), and both Ar 7 and Ar 10 are each independently selected from the groups represented by the general formulas (6) to (16) The amine compound according to claim 1, which is one.
A hole injection layer containing two kinds of compounds, wherein the first compound is the amine compound according to any one of claims 1 to 9, and the second compound is an electron acceptor p- A hole injection layer that is a dopant.
An organic electroluminescence device comprising at least an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer and a cathode, wherein the hole injection layer is at least any one of claims 1 to 9. 2. An organic electroluminescence device comprising the amine compound according to item 1.
An organic electroluminescence device having at least an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer and a cathode, wherein both the hole injection layer and the hole transport layer have An organic electroluminescence device comprising the amine compound according to claim 1 .
An organic electroluminescence device having at least an anode, a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer and a cathode, wherein at least one layer is according to any one of claims 1 to 9. An organic electroluminescence device comprising the amine compound described above.