Adamantane compound, organic light-emitting device containing the adamantane compound, and electron transport material containing the adamantane compound

Abstract

To provide an adamantane compound that forms an organic light-emitting element having long life and exhibiting high luminous efficiency, and an organic light-emitting element that contains the adamantane compound.SOLUTION: The problem is solved by an adamantane compound having a particular structure represented by the formula (1). In the formula, Ad represents a divalent or trivalent linking group represented by the formula (2), and w1, each independently, is a methine group to which A, L or Z may be bound.SELECTED DRAWING: Figure 1

Description

Technical Field

[0001] The present disclosure relates to an adamantane compound, an organic light-emitting device containing the adamantane compound, and an electron transport material containing the adamantane compound.

Background Art

[0002] Organic light-emitting devices have begun to be put into practical use mainly for small mobile applications. However, for further expansion of applications, improvement in performance is essential, and materials having long-life characteristics while having low driving voltage and high luminous efficiency characteristics are required.

[0003] Patent Documents 1, 2, and 3 disclose materials containing an adamantane moiety, which are materials for organic light-emitting devices, respectively.

Prior Art Documents

Patent Documents

[0004]

Patent Document 1

Patent Document 2

Patent Document 3

Summary of the Invention

Problems to be Solved by the Invention

[0005] Regarding the three characteristics of driving voltage, luminous efficiency, and life characteristics, which are necessary for the expansion of applications and the environments in which they can be used, the materials containing an adamantane moiety according to Patent Documents 1 to 3 do not fully satisfy these, and there is a need for materials that achieve long life and high luminous efficiency.

[0006] Therefore, one aspect of the present invention aims to provide an adamantane compound that contributes to the formation of an organic light-emitting device with long lifespan and high luminous efficiency, and an electron transport material containing the adamantane compound. Another aspect of the present invention aims to provide an organic light-emitting device with long lifespan and high luminous efficiency.

Means for Solving the Problems

[0007] Each aspect of the present invention is as follows. 1) An adamantane compound represented by formula (1).

[0008]

Chemical formula

[0009]

Chemical formula

[0010]

Chem.

[0011]

Chemical formula

[0012]

Chemical formula

[0013]

Chemical formula

[0014] In formula (T), X 3 each independently is a nitrogen atom, or a carbon atom optionally substituted with R 5 and at least one of the three X is a nitrogen atom. 3 R 4is independently an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms. R 4 is an alkyl group having 1 to 10 carbon atoms, a cyano group, a fluorine atom, an alkoxy group having 1 to 10 carbon atoms an aryl group having 6 to 20 carbon atoms composed only of an aromatic ring which may be linked and / or condensed, and optionally substituted with one or more groups selected from the group consisting of a heteroaryl group having 2 to 20 carbon atoms composed only of an aromatic ring which may be linked and / or condensed. R 5 is independently an alkyl group having 1 to 10 carbon atoms, a cyano group, a fluorine atom, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 6 to 20 carbon atoms, and adjacent R 4 and R 5 may be bonded to each other to form a condensed ring. However, in the compound represented by the general formula (1), the following group (E)

[0015]

Chemical formula

[0016]

Chemical formula

[0017] 2) A first electrode, a second electrode provided opposite to the first electrode, and an organic light-emitting device including a plurality of organic layers provided between the first electrode and the second electrode, wherein one or more of the plurality of organic layers contain the adamantane compound described in 1). 3) An electron transport material containing the adamantane compound described in 1).

Advantages of the Invention

[0018] According to one aspect of the present invention, an adamantane compound contributing to the formation of an organic light-emitting device having a long lifespan and high luminous efficiency, and an electron transport material containing the adamantane compound can be provided.

[0019] Also, according to another aspect of the present invention, an organic light-emitting device having a long lifespan and high luminous efficiency can be provided.

Brief Description of the Drawings

[0020]

Figure 1

Embodiments for Carrying Out the Invention

[0021] Hereinafter, an adamantane compound according to one aspect of the present invention (hereinafter, may also be referred to as adamantane compound (1)) will be described in detail.

[0022] The compound according to one aspect of the present invention is an adamantane compound represented by formula (1).

[0023]

Chemical formula

[0024] [Regarding Ad] In formula (1), Ad is a divalent or trivalent linking group represented by formula (2).

[0025]

Chemical formula

[0026] [Regarding A] A is, independently of each other, composed only of an azine ring; or composed only of an azine ring and a six-membered ring which may be linked and / or fused to the azine ring; an unsubstituted heteroaryl group having 2 to 30 carbon atoms, wherein the unsubstituted heteroaryl group is an alkyl group having 1 to 30 carbon atoms, a cyano group, a fluorine atom, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms composed only of an aromatic ring which may be linked and / or fused; and a heteroaryl group having 2 to 30 carbon atoms composed only of an aromatic ring which may be linked and / or fused, a substituted heteroaryl group having 2 to 30 carbon atoms substituted with one or more groups selected from the group consisting of, or a group represented by formula (3).

[0027]

Chemical formula

[0028] [Regarding the unsubstituted heteroaryl group having 2 to 30 carbon atoms] Examples of the unsubstituted heteroaryl group represented by A include pyridyl group, pyrazyl group, pyrimidyl group, pyridazyl group, triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinoxalyl group, quinazolinyl group, cinnolyl group, phthalazinyl group, pteridinyl group, phenylpyridyl group, pyridylphenyl group, benzoquinolyl group, phenanthridinyl group, phenanthrolinyl group, naphthyridinyl group, benzonaphthyridinyl group, acridinyl group, phenazinyl group, antiridinyl group, azapirenyl group, benzocinnolinyl group, benzophenanthridinyl group, phenanthradinyl group, octaazaphenanthradinyl group, anthradinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, bipyridyl group, bipyrazyl group, bipyrimidyl group, bipyridazyl group, terpyridinyl group, biquinolyl group, binaphthyridinyl group, dipyridophenazinyl group, benzoquinazolinyl group, benzoquinoxalinyl group, dibenzoquinoxalinyl group, dipyridophenazilinyl group, phenylquinolinyl group, phenylisoquinolinyl group, phenylquinoxalyl group, phenylquinazolinyl group, phenylcinnolyl group, phenylphthalazinyl group, diphenylpyridyl group, diphenyltriazinyl group, bisnaphthyltriazinyl group, bisbiphenylyltriazinyl group, pyridylterpyridinyl group, phenylquinoxalinyl group, diphenylquinoxalinyl group, diphenyldibenzoquinoxalinyl group, naphthylpyridyl group, and the like.

[0029] In terms of good performance in the organic light-emitting element, the unsubstituted heteroaryl group is preferably a heteroaryl group having 2 to 20 carbon atoms, more preferably a triazinyl group, pyridyl group, pyrimidyl group, phenylpyridyl group, diphenylpyridyl group, diphenylpyrimidyl group, quinolyl group, diphenyltriazinyl group, or acridinyl group.

[0030] [Regarding the substituted heteroaryl group having 2 to 30 carbon atoms] The unsubstituted heteroaryl group represented by A may be substituted with an alkyl group having 1 to 30 carbon atoms. The alkyl group may be any of a linear, branched, or cyclic alkyl group. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a 2-methylpropyl group, a cyclopropyl group, a methylcyclopropyl group, a butyl group, a 2-butyl group, a tert-butyl group, a 2-methylbutyl group, a 3-methylbutyl group, a 2,3-dimethylbutyl group, a 2-ethylbutyl group, a cyclobutyl group, a pentyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 4-methylpentyl group, a 2,2-dimethylpentyl group, a cyclopentyl group, a hexyl group, a 2-methylhexyl group, a 3-methylhexyl group, a cyclohexyl group, a heptyl group, a 2-methylheptyl group, a cycloheptyl group, an octyl group, a 2-methyloctyl group, a cyclooctyl group, a nonyl group, a 2-methylnonyl group, a cyclononyl group, a decyl group, a cyclodecyl group, an undecyl group, a 2-methylundecyl group, a cycloundecyl group, a dodecyl group, a cyclododecyl group, a tridecyl group, a cyclotridecyl group, a tetradecyl group, a cyclotetradecyl group, a pentadecyl group, a cyclopentadecyl group, a hexadecyl group, a cyclohexadecyl group, a heptadecyl group, a cycloheptadecyl group, an octadecyl group, a cyclooctadecyl group, a nonadecyl group, a cyclononadecyl group, an icosyl group, a cyclicosyl group, a henicicosyl group, a docosyl group, a tricosyl group, a tetracosyl group, a pentacosyl group, a hexacosyl group, a heptacosyl group, an octacosyl group, a nonacosyl group, a triacontyl group.

[0031] In terms of good performance in the organic light-emitting element, it is preferably an alkyl group having 1 to 10 carbon atoms, and more preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, a cyclopentyl group, a hexyl group, or a cyclohexyl group.

[0032] The unsubstituted heteroaryl group represented by A may be substituted with an alkoxy group having 1 to 10 carbon atoms. The alkoxy group may be any of a linear, branched, or cyclic alkyl group. Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a 2-methylpropoxy group, a cyclopropoxy group, a methylcyclopropoxy group, a butoxy group, a 2-butoxy group, a tert-butoxy group, a 2-methylbutoxy group, a 3-methylbutoxy group, a 2,3-dimethylbutoxy group, a 2-ethylbutoxy group, a cyclobutoxy group, a pentyloxy group, a 2-methylpentyloxy group, a 3-methylpentyloxy group, a 4-methylpentyloxy group, a 2,2-dimethylpentyloxy group, a cyclopentyloxy group, a hexyloxy group, a 2-methylhexyloxy group, a 3-methylhexyloxy group, a cyclohexyloxy group, a heptyloxy group, a 2-methylheptyloxy group, a cycloheptyloxy group, an octyloxy group, a 2-methyloctyloxy group, a cyclooctyloxy group, a nonyloxy group, a 2-methylnonyloxy group, a cyclononyloxy group, a decyloxy group, and a cyclodecyloxy group.

[0033] In terms of the ease of synthesizing the adamantane compound (1), it is preferably an alkoxy group having 1 to 6 carbon atoms, more preferably a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a tert-butoxy group, a pentyloxy group, a cyclopentyloxy group, a hexyloxy group, or a cyclohexyloxy group.

[0034] The unsubstituted heteroaryl group represented by A may be substituted with an aryl group having 6 to 30 carbon atoms, which is composed only of aromatic rings that may be linked and / or fused. Examples of the aryl group include phenyl group, naphthyl group, biphenylyl group, binaphthyl group, terphenyl group, anthryl group, phenanthryl group, tetracenyl group, pyrenyl group, fluoranthenyl group, triphenylenyl group, chrysenyl group, acenaphthyl group, perylenyl group, pentacenyl group, pentaphenyl group, benzopyrenyl group, naphthopyrenyl group, dibenzochrysenyl group, benzanthracenyl group, benzophenanthryl group, benzofluoranthenyl group, dibenzoanthracenyl group, picenyl group, tetraphenylenyl group, anthantrenyl group, benzoperylenyl group, coronulenyl group, coronenyl group, hexacenyl group, hexaphenyl group, heptacenyl group, heptaphenyl group, zethrenyl group, acephenanthryl group, aceanthrenyl group, benzoacephenanthryl group, quaterphenylyl group, kinkphenylyl group, dibenzopentaphenyl group, rubicenyl group, trinaphthylenyl group, pyranthrenyl group, diphenylanthryl group.

[0035] In terms of good performance in the organic light-emitting element, it is preferably an aryl group having 6 to 20 carbon atoms, and more preferably a phenyl group, naphthyl group, biphenylyl group, or phenanthryl group.

[0036] The unsubstituted heteroaryl group represented by A may be substituted with a heteroaryl group having 2 to 30 carbon atoms composed of only aromatic rings which may be linked and / or fused. Examples of the heteroaryl group include pyridyl group, pyrazyl group, pyrimidyl group, pyridazyl group, triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinoxalyl group, quinazolinyl group, cinnolyl group, phthalazinyl group, pteridinyl group, phenylpyridyl group, pyridylphenyl group, benzquinolyl group, phenanthridinyl group, phenanthrolinyl group, naphthyridinyl group, benzonaphthyridinyl group, acridinyl group, phenazinyl group, antiridinyl group, azapirenyl group, benzocinnolinyl group, benzophenanthridinyl group, phenanthradinyl group, octaazaphenanthradinyl group, anthradinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, bipyridyl group, bipyrazyl group, bipyrimidyl group, bipyridazyl group, terpyridinyl group, biquinolyl group, binaphthyridinyl group, dipyridophenazinyl group, benzquinazolinyl group, benzquinoxalinyl group, dibenzoquinoxalinyl group, dipyridophenazilinyl group, phenylquinolinyl group, phenylisoquinolinyl group, phenylquinoxalyl group, phenylquinazolinyl group, phenylcinnolyl group, phenylphthalazinyl group, diphenylpyridyl group, diphenyltriazinyl group, bisnaphthyltriazinyl group, bisbiphenylyltriazinyl group, pyridylterpyridinyl group, phenylquinoxalinyl group, diphenylquinoxalinyl group, diphenyldibenzoquinoxalinyl group, naphthylpyridyl group.

[0037] In terms of the excellent electron transport properties of the adamantane compound (1), the heteroaryl group is preferably a 1,3,5-triazinyl group substituted with a phenyl group, a naphthyl group or a biphenylyl group.

[0038] [Regarding formula (3)] R 1 and R 2Examples of the alkyl group having 1 to 30 carbon atoms represented by include the same ones as those exemplified for the alkyl group having 1 to 30 carbon atoms in the above-described substituted heteroaryl group having 2 to 30 carbon atoms. From the viewpoint of easy synthesis, it is preferably an alkyl group having 1 to 10 carbon atoms, and more preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, a cyclopentyl group, a hexyl group, or a cyclohexyl group.

[0039] R 1 and R 2 Examples of the aryl group having 6 to 30 carbon atoms represented by and include, for example, a phenyl group, a naphthyl group, a biphenylyl group, a binaphthyl group, a terphenyl group, an anthryl group, a phenanthryl group, a tetracenyl group, a pyrenyl group, a fluoranthenyl group, a triphenylenyl group, a chrysenyl group, an acenaphthyl group, a perylenyl group, a pentacenyl group, a pentaphenyl group, a benzopyrenyl group, a naphthopyrenyl group, a dibenzochrysenyl group, a benzanthracenyl group, a benzophenanthryl group, a benzofluoranthenyl group, a dibenzoanthracenyl group, a picenyl group, a tetraphenylenyl group, an anthenthrenyl group, a benzoperylenyl group, a coronulenyl group, a coronenyl group, a hexacenyl group, a hexaphenyl group, a heptacenyl group, a heptaphenyl group, a zetrenyl group, an acephenanthryl group, an acanthrenyl group, a benzoacephenanthryl group, a quaterphenylyl group, a kinkphenylyl group, a dibenzopentaphenyl group, a rubicenyl group, a trinaphthylenyl group, a pyranthrenyl group, a diphenylanthryl group, a fluorenyl group, a benzofluorenyl group, and a torquxenyl group.

[0040] R 1 and R 2 Examples of the heteroaryl group having 2 to 30 carbon atoms represented by and include, for example, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a xanthenyl group, a thioxanthenyl group, a benzoxanthenyl group, and a benzothioxanthenyl group. From the viewpoint of easy synthesis, it is preferably a phenyl group, a naphthyl group, a biphenylyl group, a phenanthryl group, a pyridyl group, a fluorenyl group, a dibenzofuranyl group, or a dibenzothienyl group.

[0041] R 1 and R 2 The alkyl group having 1 to 30 carbon atoms, aryl group having 6 to 30 carbon atoms, and heteroaryl group having 2 to 30 carbon atoms represented by may be substituted with an alkyl group having 1 to 30 carbon atoms, and those similar to the alkyl group having 1 to 30 carbon atoms exemplified for the heteroaryl group having 2 to 30 carbon atoms of the above-described substitution can be exemplified.

[0042] In terms of easy synthesis of the adamantane compound (1), it is preferably an alkyl group having 1 to 10 carbon atoms, and more preferably a methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group, pentyl group, cyclopentyl group, hexyl group, cyclohexyl group.

[0043] R 1 and R 2 The alkyl group having 1 to 30 carbon atoms, aryl group having 6 to 30 carbon atoms, and heteroaryl group having 2 to 30 carbon atoms represented by may be substituted with an alkoxy group having 1 to 10 carbon atoms, and those similar to the alkoxy group having 1 to 10 carbon atoms exemplified for the heteroaryl group having 2 to 30 carbon atoms of the above-described substitution can be exemplified.

[0044] In terms of easy synthesis of the adamantane compound (1), it is preferably an alkoxy group having 1 to 6 carbon atoms, and more preferably a methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, tert-butoxy group, pentyloxy group, cyclopentyloxy group, hexyloxy group, cyclohexyloxy group.

[0045] R 1 and R 2The alkyl group having 1 to 30 carbon atoms, aryl group having 6 to 30 carbon atoms, and heteroaryl group having 2 to 30 carbon atoms represented by may be substituted with an aryl group having 6 to 30 carbon atoms composed of only aromatic rings which may be linked and / or condensed, and examples thereof include the same as those of the aryl group having 6 to 30 carbon atoms composed of only aromatic rings which may be linked and / or condensed, exemplified by the heteroaryl group having 2 to 30 carbon atoms of the above-described substitution.

[0046] In terms of easy synthesis of the adamantane compound (1), it is preferably an aryl group having 6 to 20 carbon atoms, more preferably a phenyl group, naphthyl group, biphenylyl group, or phenanthryl group.

[0047] R in formula (3) 1 and R 2 The alkyl group having 1 to 30 carbon atoms, aryl group having 6 to 30 carbon atoms, and heteroaryl group having 2 to 30 carbon atoms represented by may be substituted with a heteroaryl group having 2 to 30 carbon atoms composed of only aromatic rings which may be linked and / or condensed, and examples thereof include the same as those of the heteroaryl group having 2 to 30 carbon atoms composed of only aromatic rings which may be linked and / or condensed, exemplified by the heteroaryl group having 2 to 30 carbon atoms of the above-described substitution.

[0048] In terms of easy synthesis of the adamantane compound (1), it is preferably a heteroaryl group having 4 to 18 carbon atoms, more preferably a pyridyl group, pyrimidyl group, triazinyl group, quinolyl group, phenylpyridyl group, pyridylphenyl group, diphenyltriazinyl group, dibenzofuranyl group, or dibenzothienyl group.

[0049] Examples of the group represented by formula (3) include groups represented by formulae (3-1) to (3-51), but the present invention is not limited thereto. Among these, in terms of good performance in the organic light-emitting element, the group represented by formula (3-1) is preferable.

[0050] [Chemical formula]

[0051] [Chemical formula]

[0052] [Chemical formula]

[0053] [Regarding L] Each of the above Ls is independently an arylene group having 6 to 30 carbon atoms or a heteroarylene group having 2 to 30 carbon atoms.

[0054] Examples of the arylene group having 6 to 30 carbon atoms represented by L include 1,2-phenylene group, 1,3-phenylene group, 1,4-phenylene group, 1,4-naphthylene group, 1,5-naphthylene group, 2,6-naphthylene group, 9,10-anthrylene group, 1,8-anthrylene group, 1,2-phenanthrylene group, 9,10-phenanthrylene group, 2,9-phenanthrylene group, 3,9-phenanthrylene group, 3,10-phenanthrylene group, naphthacene-1,2-diyl group, naphthacene-2,3-diyl group, naphthacene-1,12-diyl group, naphthacene-5,6-diyl group, pyrene-1,6-diyl group, 1,8-pyrenylene group, 2,7-pyrenylene group, biphenyl-2,2'-diyl group, biphenyl-4,4'-diyl group, biphenyl-3,4'-diyl group, biphenyl-2,3-diyl group, biphenyl-3,4-diyl group, p-terphenyl-4,4''-diyl group, m-terphenyl-4,4''-diyl group, p-terphenyl-3,3''-diyl group, o-terphenyl-4,4''-diyl group, o-terphenyl-3,3''-diyl group, chrysene-6,12-diyl group, coronene-1,8-diyltriphenylene-2,7-diyl group, binaphthyl-2,2'-diyl group, and the like.

[0055] The arylene group is preferably an arylene group having 6 to 18 carbon atoms in that the synthesis of the adamantane compound (1) is easy, and more preferably a 1,2-phenylene group, 1,3-phenylene group, 1,4-phenylene group, biphenyl-4,4'-diyl group, biphenyl-3,4'-diyl group, 2,9-phenanthrylene group.

[0056] Examples of the heteroarylene group having 2 to 30 carbon atoms represented by L include a 2,4-pyridylene group, 2,5-pyridylene group, 2,6-pyridylene group, 2,5-pyrazylene group, 2,5-pyrimidylene group, 2,4-quinolylene group, 2,6-quinolylene group, 1,3-isoquinolylene group, 2,6-quinoxalylene group, 5,8-quinoxalylene group, 5,8-quinazoline group, 5,8-cinnolylene group, 5,8-phthalazinylene group, 4,4'-phenylpyridylene group, 4,7-phenanthrylene group, 2,2'-bipyridine-4,4'-yl group, 2,2'-bipyridine-3,3'-yl group, 3,3'-bipyridine-4,4'-yl group, 3,3'-bipyridine-5,5'-yl group, 4,4'-bipyridine-3,5'-yl group, 2,2'-biquinoline-1,1'-yl group, 4,7-diphenylphenanthrene-2,9-yl group, and the like.

[0057] The heteroarylene group is preferably a heteroarylene group having 4 to 11 carbon atoms, and more preferably a 2,4-pyridylene group, 2,5-pyridylene group, 2,6-pyridylene group, 2,5-pyrazylene group, 2,5-pyrimidylene group, 2,4-quinolylene group, 2,6-quinolylene group in that the synthesis is easy.

[0058] The arylene group having 6 to 30 carbon atoms and the heteroarylene group having 2 to 30 carbon atoms represented by L are each independently an alkyl group having 1 to 30 carbon atoms, a cyano group, a fluorine atom, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms composed of only aromatic rings which may be linked and / or condensed, and It may be substituted with one or more groups selected from the group consisting of a heteroaryl group having 2 to 30 carbon atoms, which is composed only of aromatic rings that may be linked and / or condensed. As the alkyl group having 1 to 30 carbon atoms, those similar to the alkyl group having 1 to 30 carbon atoms exemplified for the heteroaryl group having 2 to 30 carbon atoms of the aforementioned substitution can be exemplified.

[0059] In terms of easy synthesis of the adamantane compound (1), it is preferably an alkyl group having 1 to 10 carbon atoms, more preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a pentyl group, a cyclopentyl group, a hexyl group, or a cyclohexyl group.

[0060] As the aryl group having 6 to 30 carbon atoms, which is composed only of aromatic rings that may be linked and / or condensed, those similar to the aryl group having 6 to 30 carbon atoms, which is composed only of aromatic rings that may be linked and / or condensed and exemplified for the heteroaryl group having 2 to 30 carbon atoms of the aforementioned substitution, can be exemplified.

[0061] In terms of easy synthesis of the adamantane compound (1), it is preferably an aryl group having 6 to 20 carbon atoms, more preferably a phenyl group, a naphthyl group, a biphenylyl group, an anthryl group, or a phenanthryl group.

[0062] As the heteroaryl group having 2 to 30 carbon atoms, which is composed only of aromatic rings that may be linked and / or condensed, those similar to the heteroaryl group having 2 to 30 carbon atoms, which is composed only of aromatic rings that may be linked and / or condensed and exemplified for the heteroaryl group having 2 to 30 carbon atoms of the aforementioned substitution, can be exemplified.

[0063] In terms of easy synthesis of the adamantane compound (1), it is preferably the heteroaryl group having 4 to 23 carbon atoms, more preferably a pyridyl group, a pyrimidyl group, a triazinyl group, a quinolyl group, a pyridylphenyl group, a diphenyltriazinyl group, a bisnaphthyltriazinyl group, a dibenzofuranyl group, or a dibenzothienyl group.

[0064] It is more preferable that the substituent(s) possessed by L is / are one or more substituents selected from the group consisting of a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, a cyano group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and a ring formed by the bonding of these substituents.

[0065] It is more preferable that L is each independently a phenylene group, a naphthylene group, a fluorenylene group, an anthrylene group, or a phenanthrylene group.

[0066] [Regarding Z] Each of the said Z is independently a group represented by formula (4).

[0067] [Chemical formula]

[0068] In formula (4), m 1 each independently represents an integer from 0 to 4. m 2 each independently represents an integer from 1 to 4. L 1 each independently is an arylene group having 6 to 30 carbon atoms, or a heteroarylene group having 2 to 30 carbon atoms containing an azine ring, Ar 1 each independently is a cyano group, an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, a heteroarylene group having 2 to 30 carbon atoms containing a nitrogen atom, an oxygen atom, or a sulfur atom that forms a double bond with an adjacent atom, or a group represented by formula (5a), (5b), (5c), or (5d).

[0069] [Chemical formula]

[0070] In formulas (5a) to (5d), R 3a ~R 3h are each independently Hydrogen atoms, an alkyl group having 1 to 30 carbon atoms; an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms, Adjacent R 3a and R 3b ;R 3c and R 3d ; and R 3f , R 3g and R 3h may be bonded to each other to form a condensed ring.

[0071] [[L 1 About L 1 Examples of the arylene group having 6 to 30 carbon atoms represented by the formula (I) include the same arylene groups having 6 to 30 carbon atoms as exemplified for L. Among them, in terms of ease of synthesis of the adamantane compound (1), an arylene group having 6 to 18 carbon atoms is preferred, and a 1,2-phenylene group, a 1,3-phenylene group, a 1,4-phenylene group, a biphenyl-4,4'-diyl group, a 3,9-phenanthrylene group, or a 3,10-phenanthrylene group is more preferred.

[0072] L 1 Examples of the heteroarylene group having 2 to 30 carbon atoms and containing an azine ring represented by the formula (I) include the same heteroarylene groups having 2 to 30 carbon atoms as exemplified for L. Among them, from the viewpoint of ease of synthesis, a heteroarylene group having 4 to 12 carbon atoms is preferable, and a 2,4-pyridylene group, a 2,5-pyridylene group, a 2,6-pyridylene group, a 2,5-pyrazylene group, a 2,5-pyrimidylene group, a 2,4-quinolylene group, or a 2,6-quinolylene group is more preferable.

[0073] L 1The group represented by is each independently, an alkyl group having 1 to 30 carbon atoms, a cyano group, a fluorine atom, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms composed of only aromatic rings which may be linked and / or condensed, and a heteroaryl group having 2 to 30 carbon atoms composed of only aromatic rings which may be linked and / or condensed, and may be substituted with one or more groups selected from the group consisting of. Examples of the alkyl group having 1 to 30 carbon atoms include the same ones as those exemplified for the alkyl group having 1 to 30 carbon atoms in the heteroaryl group having 2 to 30 carbon atoms of the above-described substitution.

[0074] Among these, an alkyl group having 1 to 18 carbon atoms is preferable in terms of easy synthesis of the adamantane compound (1), and a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a cyclopentyl group, a cyclohexyl group, a methylcyclohexyl group, and a pentylcyclohexyl group are more preferable.

[0075] Examples of the alkoxy group having 1 to 10 carbon atoms include the same ones as those exemplified for the alkoxy group having 1 to 10 carbon atoms in the heteroaryl group having 2 to 30 carbon atoms of the above-described substitution. Among these,

[0076] an alkoxy group having 1 to 6 carbon atoms is preferably an alkoxy group having 1 to 6 carbon atoms in terms of easy synthesis of the adamantane compound (1), and a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a tert-butoxy group, a pentyloxy group, a cyclopentyloxy group, a hexyloxy group, and a cyclohexyloxy group are more preferable.

[0077] Examples of the aryl group having 6 to 30 carbon atoms, which is composed only of aromatic rings that may be linked and / or condensed, include the same groups as those of the aryl group having 6 to 30 carbon atoms, which is composed only of aromatic rings that may be linked and / or condensed, exemplified for the above-mentioned substituted heteroaryl group having 2 to 30 carbon atoms.

[0078] Among these, in terms of the ease of synthesis of the adamantane compound (1), an aryl group having 6 to 20 carbon atoms is preferable, and a phenyl group, a naphthyl group, a biphenylyl group, an anthryl group, or a phenanthryl group is more preferable.

[0079] Examples of the heteroaryl group having 2 to 30 carbon atoms, which is composed only of aromatic rings that may be linked and / or condensed, include the same groups as those of the heteroaryl group having 2 to 30 carbon atoms, which is composed only of aromatic rings that may be linked and / or condensed, exemplified for the above-mentioned substituted heteroaryl group having 2 to 30 carbon atoms.

[0080] Among these, in terms of the ease of synthesis of the adamantane compound (1), a heteroaryl group having 4 to 23 carbon atoms is preferable, and a pyridyl group, a pyrimidyl group, a triazinyl group, a quinolyl group, a pyridylphenyl group, a diphenyltriazinyl group, a bisnaphthyltriazinyl group, a dibenzofuranyl group, or a dibenzothienyl group is more preferable.

[0081] L 1 is preferably each independently a phenylene group, a naphthylene group, a fluorenylene group, an anthrylene group, a phenanthrylene group, a benzofluorenylene group, a pyrenylene group, a perylenylene group, a fluoranthenylene group, a triphenylenylene group, a chrysenylene group, an acenaphthylene group, a dibenzochrysenylene, a benzofuranylene group, a benzothienylene group, a dibenzofuranylene group, a dibenzothienylene group, a xanthenylene group, or a thioxanthenylene group, which may have a substituent. L 1is more preferably each independently a phenylene group, a naphthylene group, a fluorenylene group, an anthrylene group, or a phenanthrylene group.

[0082] L 1 The substituent that [Ar

[0083] [[has is more preferably one or more substituents selected from the group consisting of a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, a cyano group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and a ring formed by bonding these substituents. 1 for]] Ar 1 Examples of the alkyl group having 1 to 30 carbon atoms represented by [Ar

[0084] Ar 1 can be the same as those exemplified for the alkyl group having 1 to 30 carbon atoms in the above-described substituted heteroaryl group having 2 to 30 carbon atoms. Among them, an alkyl group having 1 to 18 carbon atoms is preferable in terms of ease of synthesis, and a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a cyclopentyl group, a cyclohexyl group, a methylcyclohexyl group, or a pentylcyclohexyl group is more preferable.

[0085] Ar 1Examples of the C2-30 heteroaryl group containing a nitrogen atom, an oxygen atom, or a sulfur atom that forms a double bond with an adjacent atom, represented by , include a pyridyl group, a pyrazyl group, a pyrimidyl group, a pyridazyl group, a triazinyl group, a tetrazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalyl group, a quinazolinyl group, a cinnolyl group, a phthalazinyl group, a pteridinyl group, a phenylpyridyl group, a pyridylphenyl group, a benzquinolyl group, a phenanthridinyl group, a phenanthrolinyl group, a naphthyridinyl group, a benzonaphthyridinyl group, an acridinyl group, a phenazinyl group, an antiridinyl group, an azapirenyl group, a benzocinnolinyl group, a benzophenanthridinyl group, a phenanthradinyl group, an octaazaphenanthradinyl group, an anthradinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group, a bipyridyl group, a bipyrazyl group, a bipyrimidyl group, a bipyridazyl group, a terpyridinyl group, a biquinolyl group, a binaphthyridinyl group, a dipyridophenazinyl group, a benzquinazolinyl group, a benzquinoxalinyl group, a dibenzquinoxalinyl group, a dipyridophenazilinyl group, a phenylquinolinyl group, a phenylisoquinolinyl group, a phenylquinoxalyl group, a phenylquinazolinyl group, a phenylcinnolyl group, a phenylphthalazinyl group, a diphenylpyridyl group, a diphenyltriazinyl group, a bisnaphthyltriazinyl group, a bisbiphenylyltriazinyl group, a pyridylterpyridinyl group, a phenylquinoxalinyl group, a diphenylquinoxalinyl group, a diphenyldibenzquinoxalinyl group, a naphthylpyridyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzonaphthofuranyl group, a benzonaphthothienyl group, a dinaphthofuranyl group, a dinaphthothienyl group, a xanthenyl group, a thioxanthenyl group, a benzoxanthenyl group, a benzothioxanthenyl group, a benzodioxanthenyl group, an oxanthrenyl group, a thianthrenyl group, a phenoxathiinyl group, and the like.

[0086] Among these, in terms of the ease of synthesizing the adamantane compound (1), it is preferably a benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, xanthenyl group, thioxanthenyl group, triazinyl group, pyrazyl group, pyrimidyl group, pyridyl group, quinolyl group, isoquinolyl group, quinoxalyl group, quinazolinyl group, cinnolyl group, acridinyl group, and more preferably a dibenzofuranyl group, dibenzothienyl group, xanthenyl group, pyridyl group, quinolyl group, acridinyl group. Ar 1 is preferably a cyano group.

[0087] [[Regarding the group represented by formula (5a), (5b), (5c) or (5d)]] R 3a ~R 3h Examples of the alkyl group having 1 to 30 carbon atoms represented by can be the same as those of the alkyl group having 1 to 30 carbon atoms exemplified for the substituted heteroaryl group having 2 to 30 carbon atoms described above.

[0088] Among these, in terms of the ease of synthesizing the adamantane compound (1), it is preferably an alkyl group having 1 to 18 carbon atoms, and more preferably a methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group, hexyl group, heptyl group, octyl group, nonyl group, cyclopentyl group, cyclohexyl group, methylcyclohexyl group, pentylcyclohexyl group.

[0089] R 3a ~R 3h Examples of the aryl group having 6 to 30 carbon atoms represented by can be the same as those of the aryl group having 6 to 30 carbon atoms exemplified for the substituted heteroaryl group having 2 to 30 carbon atoms described above.

[0090] Among these, in terms of the ease of synthesis of the adamantane compound (1), it is preferably an aryl group having 6 to 26 carbon atoms, and is preferably a phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, chrysenyl group, acenaphthyl group, dibenzochrysenyl group.

[0091] R 3a ~R 3h Examples of the heteroaryl group having 2 to 30 carbon atoms represented by ~R 3h can be the same as those of the heteroaryl group having 2 to 30 carbon atoms exemplified by the above-described substituted heteroaryl group having 2 to 30 carbon atoms.

[0092] Among these, in terms of the ease of synthesis of the adamantane compound (1), it is preferably a heteroaryl group having 2 to 18 carbon atoms, and is preferably a benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, xanthenyl group, thioxanthenyl group, triazolyl group, pyrazyl group, pyrimidyl group, pyridyl group, quinolyl group, isoquinolyl group, quinoxalyl group, quinazolinyl group, cinnolyl group.

[0093] Also, adjacent R 3a and R 3b ; R 3c and R 3d ; and R 3f , R 3g and R 3h may be bonded to each other to form a condensed ring.

[0094] The alkyl group having 1 to 30 carbon atoms, aryl group having 6 to 30 carbon atoms and heteroaryl group having 2 to 30 carbon atoms represented by R 3a ~R 3h in formula (5) may be substituted with an alkyl group having 1 to 30 carbon atoms.

[0095] ​​​​​​​​​​​​​​​​​​Among these, the same alkyl groups having 1 to 30 carbon atoms as those exemplified by the above-described heteroaryl groups having 2 to 30 carbon atoms for substitution can be exemplified. In terms of the ease of synthesis of the adamantane compound (1), alkyl groups having 1 to 10 carbon atoms are preferable, and methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group, pentyl group, cyclopentyl group, hexyl group, cyclohexyl group are more preferable.

[0096] R 3a ~R 3h The alkyl group having 1 to 30 carbon atoms, the aryl group having 6 to 30 carbon atoms, and the heteroaryl group having 2 to 30 carbon atoms represented by ~ may be substituted with an alkoxy group having 1 to 10 carbon atoms.

[0097] Among these, the same alkoxy groups having 1 to 10 carbon atoms as those exemplified by the above-described heteroaryl groups having 2 to 30 carbon atoms for substitution can be exemplified.

[0098] In terms of the ease of synthesis of the adamantane compound (1), it is preferable that the alkoxy group has 1 to 6 carbon atoms, and it is more preferable that the alkoxy group is methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, tert-butoxy group, pentyloxy group, cyclopentyloxy group, hexyloxy group, cyclohexyloxy group.

[0099] R 3a ~R 3h The alkyl group having 1 to 30 carbon atoms, the aryl group having 6 to 30 carbon atoms, and the heteroaryl group having 2 to 30 carbon atoms represented by ~ may be substituted with an aryl group having 6 to 30 carbon atoms which is composed of only aromatic rings which may be linked and / or condensed. Among these, the same aryl groups having 6 to 30 carbon atoms which are composed of only aromatic rings which may be linked and / or condensed as those exemplified by the above-described heteroaryl groups having 2 to 30 carbon atoms for substitution can be exemplified.

[0100] It is preferably an aryl group having 6 to 20 carbon atoms in that the synthesis of the adamantane compound (1) is easy, and more preferably a phenyl group, a naphthyl group, a biphenylyl group, or a phenanthryl group.

[0101] R in formula (5) 3a ~R 3h The alkyl group having 1 to 30 carbon atoms, the aryl group having 6 to 30 carbon atoms, and the heteroaryl group having 2 to 30 carbon atoms represented by may be substituted with a heteroaryl group having 2 to 30 carbon atoms composed of only aromatic rings which may be linked and / or condensed. Among these, the same ones as the heteroaryl group having 2 to 30 carbon atoms composed of only aromatic rings which may be linked and / or condensed, exemplified by the heteroaryl group having 2 to 30 carbon atoms of the above-described substitution, can be exemplified.

[0102] It is preferably a heteroaryl group having 4 to 18 carbon atoms in that the synthesis of the adamantane compound (1) is easy, and more preferably a pyridyl group, a pyrimidyl group, a triazinyl group, a quinolyl group, a phenylpyridyl group, a pyridylphenyl group, a diphenyltriazinyl group, a dibenzofuranyl group, or a dibenzothienyl group.

[0103] Specific examples of the group represented by formula (5a), (5b), (5c) or (5d) include formula (5a-1) to (5a-24), (5b-1) to (5b-24), (5c-1) to (5c-24) and (5d-1) to (5d-24).

[0104]

Chemical formula

[0105]

Chemical formula

[0106]

Chemical formula

[0107]

Chem.

[0108]

Chem.

[0109]

Chem.

[0110]

Chem.

[0111] Ar 1 The group represented by each is independently an alkyl group having 1 to 30 carbon atoms, a cyano group, a fluorine atom, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms composed only of aromatic rings which may be linked and / or condensed, and optionally substituted with one or more groups selected from the group consisting of a heteroaryl group having 2 to 30 carbon atoms composed only of aromatic rings which may be linked and / or condensed.

[0112] Examples of the alkyl group having 1 to 30 carbon atoms include the same ones as those of the alkyl group having 1 to 30 carbon atoms exemplified for the heteroaryl group having 2 to 30 carbon atoms with the aforementioned substitution.

[0113] Among these, in terms of easy synthesis of the adamantane compound (1), an alkyl group having 1 to 18 carbon atoms is preferable, and a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a cyclopentyl group, a cyclohexyl group, a methylcyclohexyl group, a pentylcyclohexyl group are more preferable.

[0114] In addition, examples of the aryl group having 6 to 30 carbon atoms composed only of aromatic rings which may be linked and / or condensed include the same as those of the aryl group having 6 to 30 carbon atoms composed only of aromatic rings which may be linked and / or condensed, as exemplified by the above-described substituted heteroaryl group having 2 to 30 carbon atoms.

[0115] Among these, in terms of the ease of synthesis of the adamantane compound (1), an aryl group having 6 to 20 carbon atoms is preferable, and a phenyl group, a naphthyl group, a biphenylyl group, an anthryl group, or a phenanthryl group is more preferable.

[0116] In addition, examples of the heteroaryl group having 2 to 30 carbon atoms composed only of aromatic rings which may be linked and / or condensed include the same as those of the heteroaryl group having 2 to 30 carbon atoms composed only of aromatic rings which may be linked and / or condensed, as exemplified by the above-described substituted heteroaryl group having 2 to 30 carbon atoms.

[0117] Among these, in terms of the ease of synthesis of the adamantane compound (1), a heteroaryl group having 4 to 23 carbon atoms is preferable, and a pyridyl group, a pyrimidyl group, a triazinyl group, a quinolyl group, a pyridylphenyl group, a diphenyltriazinyl group, a bisnaphthyltriazinyl group, a dibenzofuranyl group, or a dibenzothienyl group is more preferable.

[0118] Ar 1are each independently a cyano group, or a phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, benzofluorenyl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, chrysenyl group, acenaphthyl group, dibenzochrysenyl group, benzofuranyl group, benzothienyl group, dibenzofuranyl group, dibenzothienyl group, xanthenyl group, thioxanthenyl group, triazyl group, pyrazyl group, pyrimidyl group, pyridyl group, quinolyl group, isoquinolyl group, quinoxalyl group, quinazolyl group, or cinnolyl group, each of which may have a substituent.

[0119] Ar 1 is preferably one or more substituents selected from the group consisting of a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, a cyano group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and a ring formed by bonding these substituents.

[0120] Ar 1 are each independently a cyano group, or a phenyl group, naphthyl group, fluorenyl group, anthryl group, phenanthryl group, fluoranthenyl group, triphenylenyl group, dibenzofuranyl group, dibenzothienyl group, or xanthenyl group, each of which may have a substituent.

[0121] Ar 1 It is more preferable that the substituents contained in the ring are one or more substituents selected from the group consisting of a phenyl group, a tolyl group, a pyridyl group, a fluorine atom, a cyano group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and a ring formed by bonding these substituents.

[0122] [[m 1 , m 2 , p, n 1 and n 2 About m 1 each independently represents an integer of 0 to 4. m 2Each independently represents an integer from 1 to 4. m 2 is preferably 1, 2, or 3. Each p independently represents an integer from 0 to 4. p is preferably 1, 2, or 3. n 1 and n 2 Each independently represents an integer from 0 to 2. n 1 is preferably 0 or 1. n 1 and n 2 satisfy 1 ≤ n 1 + n 2 ≤ 2.

[0123] However, the adamantane compound (1) has at least one group represented by formula (T) in the molecule.

[0124]

Chemical formula

[0125] [Regarding (T)] In formula (T), X 3 each independently represents a nitrogen atom or a carbon atom optionally substituted by R 5 , and at least one of the three X 3 is a nitrogen atom.

[0126] [[Regarding R 5 R 5 each independently represents an alkyl group having 1 to 10 carbon atoms, a cyano group, a fluorine atom, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms.

[0127] R 5 ​The alkyl group having 1 to 10 carbon atoms represented by may be any of linear, branched, and cyclic alkyl groups. Specifically, methyl group, ethyl group, propyl group, isopropyl group, 2-methylpropyl group, cyclopropyl group, methylcyclopropyl group, butyl group, 2-butyl group, tert-butyl group, 2-methylbutyl group, 3-methylbutyl group, 2,3-dimethylbutyl group, 2-ethylbutyl group, cyclobutyl group, pentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group, 2,2-dimethylpentyl group, hexyl group, 2-methylhexyl group, 3-methylhexyl group, cyclohexyl group, heptyl group, 2-methylheptyl group, cycloheptyl group, octyl group, 2-methyloctyl group, cyclooctyl group, nonyl group, 2-methylnonyl group, cyclononyl group, decyl group, cyclodecyl group can be exemplified.

[0128] Among these, in terms of easy synthesis of the adamantane compound (1), it is preferably an alkyl group having 1 to 6 carbon atoms, and more preferably a methyl group, ethyl group, propyl group, isopropyl group, butyl group, tert-butyl group, hexyl group, cyclopentyl group, cyclohexyl group.

[0129] R 5 Examples of the aryl group having 6 to 20 carbon atoms represented by include phenyl group, naphthyl group, biphenylyl group, anthryl group, phenanthryl group, pyrenyl group, perylenyl group, fluoranthenyl group, triphenylenyl group, chrysenyl group, acenaphthyl group, fluorenyl group, benzofluorenyl group and the like.

[0130] In terms of easy synthesis of the adamantane compound (1), it is preferably an aryl group having 6 to 15 carbon atoms, and more preferably a phenyl group, naphthyl group, biphenylyl group, anthryl group, phenanthryl group.

[0131] R 5Examples of the heteroaryl group having 2 to 20 carbon atoms represented by include a pyridyl group, a pyrazyl group, a pyrimidyl group, a pyridazinyl group, a triazinyl group, a tetrazinyl group, a quinolyl group, an isoquinolyl group, a quinoxalyl group, a quinazolinyl group, a cinnolyl group, a phthalazinyl group, a phenylpyridyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, a xanthenyl group, a thioxanthenyl group, a benzoxanthenyl group, a benzothioxanthenyl group, a benzoquinolyl group, a phenanthridinyl group, a phenanthrolinyl group, a benzonaphthyldinyl group, an acridinyl group, a phenazinyl group, an anthridinyl group, an azapirenyl group, and the like.

[0132] In terms of the ease of synthesis of the adamantane compound (1), it is preferably a heteroaryl group having 4 to 18 carbon atoms, and preferably a pyridyl group, a pyrimidyl group, a triazinyl group, a quinolyl group, an isoquinolyl group, a phenylpyridyl group, a pyridylphenyl group, or a diphenyltriazinyl group.

[0133] R 5 is preferably, independently of each other, an alkyl group having 1 to 10 carbon atoms, a cyano group, a fluorine atom, or an aryl group having 6 to 20 carbon atoms.

[0134] [[R 4 with respect to]] R 4 is, independently of each other, an aryl group having 6 to 20 carbon atoms, or a heteroaryl group having 2 to 20 carbon atoms.

[0135] R 4 Examples of the aryl group having 6 to 20 carbon atoms represented by include the same groups as the aryl groups exemplified for the above R 5 In terms of good performance in the organic light-emitting element, it is preferably an aryl group having 6 to 18 carbon atoms, and more preferably a phenyl group, a naphthyl group, a biphenylyl group, an anthryl group, or a phenanthryl group.

[0136] R 4 Examples of the heteroaryl group having 2 to 20 carbon atoms represented by include the same as the heteroaryl groups exemplified for the above R5 Examples similar to the heteroaryl groups exemplified in [0000151] can be given. In terms of good performance in the organic light-emitting element, a heteroaryl group having 5 to 18 carbon atoms is preferable, and a pyridyl group, a pyrimidyl group, a phenylpyridyl group, a diphenylpyridyl group, a triazinyl group, a quinolyl group, and an acridinyl group are more preferable. Adjacent R 4 and R 5 may be bonded to each other to form a condensed ring.

[0137] R 4 The group represented by an alkyl group having 1 to 10 carbon atoms, a cyano group, a fluorine atom, an alkoxy group having 1 to 10 carbon atoms an aryl group having 6 to 20 carbon atoms composed only of an aromatic ring which may be linked and / or condensed, and may be substituted with one or more groups selected from the group consisting of a heteroaryl group having 2 to 20 carbon atoms composed only of an aromatic ring which may be linked and / or condensed.

[0138] Examples of the alkyl group having 1 to 10 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a 2-methylpropyl group, a cyclopropyl group, a methylcyclopropyl group, a butyl group, a 2-butyl group, a tert-butyl group, a 2-methylbutyl group, a 3-methylbutyl group, a 2,3-dimethylbutyl group, a 2-ethylbutyl group, a cyclobutyl group, a pentyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 4-methylpentyl group, a 2,2-dimethylpentyl group, a hexyl group, a 2-methylhexyl group, a 3-methylhexyl group, a cyclohexyl group, a heptyl group, a 2-methylheptyl group, a cycloheptyl group, an octyl group, a 2-methyloctyl group, a cyclooctyl group, a nonyl group, a 2-methylnonyl group, a cyclononyl group, a decyl group, a cyclodecyl group, and the like.

[0139] Among these, in terms of the ease of synthesizing the adamantane compound (1), it is preferably an alkyl group having 1 to 6 carbon atoms, and more preferably a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a tert-butyl group, a hexyl group, a cyclopentyl group, or a cyclohexyl group.

[0140] Examples of the alkoxy group having 1 to 10 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a 2-methylpropoxy group, a cyclopropoxy group, a methylcyclopropoxy group, a butoxy group, a 2-butoxy group, a tert-butoxy group, a 2-methylbutoxy group, a 3-methylbutoxy group, a 2,3-dimethylbutoxy group, a 2-ethylbutoxy group, a cyclobutoxy group, a pentyloxy group, a 2-methylpentyloxy group, a 3-methylpentyloxy group, a 4-methylpentyloxy group, a 2,2-dimethylpentyloxy group, a cyclopentyloxy group, a hexyloxy group, a 2-methylhexyloxy group, a 3-methylhexyloxy group, a cyclohexyloxy group, a heptyloxy group, a 2-methylheptyloxy group, a cycloheptyloxy group, an octyloxy group, a 2-methyloctyloxy group, a cyclooctyloxy group, a nonyloxy group, a 2-methylnonyloxy group, a cyclononyloxy group, a decyloxy group, and a cyclodecyloxy group.

[0141] Among these, in terms of the ease of synthesizing the adamantane compound (1), it is preferably an alkoxy group having 1 to 6 carbon atoms, and more preferably a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, a tert-butoxy group, a pentyloxy group, a cyclopentyloxy group, a hexyloxy group, or a cyclohexyloxy group.

[0142] Examples of the aryl group having 6 to 20 carbon atoms, which may be composed only of the aromatic rings that may be linked and / or condensed, include a phenyl group, a naphthyl group, a biphenylyl group, a binaphthyl group, a terphenyl group, an anthryl group, a phenanthryl group, a tetracenyl group, a pyrenyl group, a fluoranthenyl group, a triphenylenyl group, a chrysenyl group, an acenaphthyl group, a perylenyl group, a benzopyrenyl group, a benzanthracenyl group, a benzophenanthryl group, a benzofluoranthenyl group, a coronulenyl group, an acephenanthryl group, an acanthrylenyl group, and a benzoacephenanthryl group.

[0143] In terms of the ease of synthesizing the adamantane compound (1), it is preferably an aryl group having 6 to 15 carbon atoms, more preferably a phenyl group, a naphthyl group, a biphenylyl group, an anthryl group, or a phenanthryl group.

[0144] Examples of the heteroaryl group having 2 to 20 carbon atoms and composed of only the aromatic ring which may be linked and / or condensed include, for example, pyridyl group, pyrazyl group, pyrimidyl group, pyridazyl group, triazinyl group, tetrazinyl group, quinolyl group, isoquinolyl group, quinoxalyl group, quinazolinyl group, cinnolyl group, phthalazinyl group, pteridinyl group, phenylpyridyl group, pyridylphenyl group, benzoquinolyl group, phenanthridinyl group, phenanthrolinyl group, naphthyridinyl group, benzonaphthyridinyl group, acridinyl group, phenazinyl group, antiridinyl group, azopyrenyl group, benzocinnolinyl group, benzophenanthridinyl group, octaazaphenanthradinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, bipyridyl group, bipyrazyl group, bipyrimidyl group, bipyridazyl group, terpyridinyl group, biquinolyl group, binaphthyridinyl group, dipyridophenazinyl group, benzobenzoxalinyl group, benzobenzoxazinyl group, dibenzobenzoxazinyl group, dipyridophenazilinyl group, phenylquinolinyl group, phenylisoquinolinyl group, phenylquinoxalyl group, phenylquinazolinyl group, phenylcinnolyl group, phenylphthalazinyl group, diphenylpyridyl group, diphenyltriazinyl group, pyridylterpyridinyl group, phenylquinoxalinyl group, diphenylquinoxalinyl group, naphthylpyridyl group.

[0145] In terms of the ease of synthesis of the adamantane compound (1), it is preferably the heteroaryl group having 4 to 18 carbon atoms, more preferably pyridyl group, pyrimidyl group, triazinyl group, quinolyl group, phenylpyridyl group, pyridylphenyl group, diphenyltriazinyl group, dibenzofuranyl group, dibenzothienyl group.

[0146] The adamantane compound (1) has at least one group represented by the formula (T) and does not have two or more triazine rings. Here, not having two or more means not having a triazine ring or having only one triazine ring.

[0147] Examples of the group represented by the formula (T) include, but are not limited to, the groups represented by the formulas (T-1) to (T-36).

[0148]

Chemical formula

[0149]

Chemical formula

[0150] Among the groups represented by the formulas (T-1) to (T-36), the groups represented by the formulas (T-1), (T-3), (T-4), (T-5), (T-10), and (T-12) are preferred in terms of ease of synthesis of the adamantane compound (1).

[0151] In the compound represented by the general formula (1), the following group (E)

[0152]

Chemical formula

[0153]

Chemical formula

[0154] Here, having a different compositional formula means that the composition of the elements constituting each group is different as a whole. Thus, the adamantane compound (1) according to one aspect of the present invention preferably does not have a symmetry axis passing through Ad. That is, the adamantane compound (1) is preferably asymmetric about Ad. By adopting such a structure, the amorphous property can be improved.

[0155] <Specific examples of adamantane compounds> A more preferred structure of the adamantane compound (1) is represented by formula (1a), (1b), (1c), (1d) or (1e).

[0156]

Chem.

[0157]

Chem.

[0158]

Chem.

[0159]

Chem.

[0160]

Chem.

[0161] In each formula, A, L, Z, and p have the same meanings as described above.

[0162] Specific examples of the adamantane compound (1) are illustrated by Formulas 1-1 to 1-250, but the present invention is not limited thereto.

[0163]

Chem.

[0164]

Chem.

[0165]

Chem.

[0166]

Chem.

[0167]

Chem.

[0168]

Chem.

[0169]

Chem.

[0170]

Chem.

[0171]

Chem.

[0172]

Chem.

[0173]

Chem.

[0174]

Chem.

[0175]

Chem.

[0176]

Chem.

[0177]

Chem.

[0178]

Chem.

[0179]

Chem.

[0180]

Chem.

[0181]

Chem.

[0182] Among the adamantane compounds represented by Formulas (1-1) to (1-250), in terms of good performance in an organic light-emitting device, Formulas (1-1) to (1-13), (1-14) to (1-16), (1-20) to (1-22), (1-25), (1-29) to (1-31), (1-38), (1-41), (1-44), (1-49), (1-55) to (1-58), (1-62) to (1-66), (1-70), (1-73) to (1-74), (1-78), (1-80), (1-82) to (1-83), (1-85) to (1-88), (1-93), (1-94), (1-98) to (1-101), (1-107) to (1-109), (1-114), (1-117), (1-122) to (1-125), (1-179), (1-198), (1-229), (1-239) to (1-241), (1-248) to (1-250) are preferred, and the compounds represented by Formulas (1-1), (1-3), (1-5), (1-6), (1-12), (1-14), (1-22), (1-29), (1-38), (1-41), (1-49), (1-85), (1-94), (1-107), (1-109), (1-114), (1-117), (1-122), (1-248) to (1-250) are more preferred.

[0183] The adamantane compound (1) according to one aspect of the present invention can be produced by appropriately combining known reactions. For example, the adamantane compounds (1'), (1''), and (1''') contained in the adamantane compound (1) according to one aspect of the present disclosure can be produced according to the production method shown by any one of the synthesis routes (i) to (vi) shown in the following reaction formulas, but should not be construed as being limited by these examples.

[0184]

Chemical formula

[0185]

Chemical formula

[0186] [Chemistry]

[0187] [Chemistry]

[0188] [Chemistry]

[0189] [Chemistry]

[0190] In synthetic routes (i) to (vi), A, L, L 1 , Ar 1 , m 1 and p represent the same meanings as described above. Q 1 , Q 2 , Q 3 and Q 4 each independently represent a leaving group. Examples of the leaving group include a chlorine atom, a bromine atom, an iodine atom, a trifluoromethanesulfonyloxy group, etc. Among these, a trifluoromethanesulfonyloxy group, a bromine atom, or a chlorine atom is preferable in terms of good reaction yield. G represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group. The two Gs in B(OG)2 may be the same or different. The two Gs may combine to form a ring containing an oxygen atom and a boron atom.

[0191] B(OG)2 is not particularly limited, and examples thereof include B(OH)2, B(OMe)2, B(O i Pr)2, B(OBu)2, B(OPh)2, etc. Here, Me represents a methyl group, iPr represents an isopropyl group, Bu represents a butyl group, and Ph represents a phenyl group. Examples of B(OG)2 when two Gs combine to form a ring containing an oxygen atom and a boron atom are not particularly limited, but for example, groups represented by the following formulas (I) to (VI) can be exemplified, and in terms of good yield, the group represented by formula (II) is preferred.

[0192]

Chemical formula

[0193] The coupling reactions in synthetic routes (i) to (vi) are methods of reacting a compound having a leaving group represented by formula (7), (8), (10), (14), (15), (16), (19) or (20) with a boron compound represented by formula (9), (11), (12), (13), (17) or (18) in the presence of a palladium catalyst and a base, and the reaction conditions of a general Suzuki-Miyaura reaction can be applied. The compound having a leaving group is preferably used in an amount of 0.5 to 3.0 molar equivalents relative to the boron compound in terms of good reaction yield.

[0194] The compound having a leaving group represented by formula (7) can be produced, for example, according to the methods disclosed in Journal of the American Chemical Society, Vol. 126, p. 14843, 2004 or Macromolecules, Vol. 49, p. 3838, 2016, or Chemistry of Materials, Vol. 18, p. 308, 2006, by synthesizing 1,3-bis(4-hydroxyphenyl)adamantane and applying a general trifluoromethanesulfonyloxylation reaction (for example, Published Patent Gazette No. 6492432). Commercially available products may also be used.

[0195] The compound having a leaving group represented by formula (14) can be produced, for example, by synthesizing 1,3,5-tris(4-hydroxyphenyl)adamantane according to the method disclosed in Journal of the American Chemical Society, Vol. 136, p. 10499, 2014 or Japanese Patent Laid-Open No. 2003 / 306461, and applying a general trifluoromethanesulfonyloxylation reaction (for example, Japanese Patent Laid-Open No. 6492432).

[0196] The compound having a leaving group represented by formula (19) and formula (20) can be produced, for example, according to Journal of the American Chemical Society, Vol. 74, p. 6289, 1952 or Synlett, p. 808, 2002. Commercially available products may also be used.

[0197] The boronation reaction in synthesis routes (i) to (vi) is a method of producing a boron compound represented by formula (9), (11) or (12) by reacting a compound having a leaving group represented by formula (7), (8) or (10) with a boron raw material (for example, pinacolato borane, bis(pinacolato)diborane, etc.) in the presence of a palladium catalyst and a base. The boronation reaction can obtain the target product in good yield by applying the reaction conditions for synthesizing a general organometallic compound (see, for example, Angew. Chem. Int. Ed. 2007, 46, 5359-5363).

[0198] The boron compound represented by formula (17) can be synthesized, for example, using a reaction for synthesizing a general organometallic compound from a compound having a leaving group represented by formula (20) (see, for example, Angew. Chem. Int. Ed. 2007, 46, 5359-5363). Commercially available products may also be used.

[0199] The boron compound represented by the formula (18) can be synthesized, for example, using a reaction for synthesizing a general organometallic compound from a compound having a leaving group represented by the formula (19) (see, for example, Angew. Chem. Int. Ed. 2007, 46, 5359-5363). Alternatively, a commercially available product may be used.

[0200] The palladium catalyst used in the above-mentioned coupling reaction and borylation reaction is not particularly limited, but specifically, palladium salts such as palladium chloride, palladium acetate, palladium trifluoroacetate, palladium nitrate, etc., π-allylpalladium chloride dimer, palladium acetylacetonate, tris(dibenzylideneacetone)dipalladium, bis(dibenzylideneacetone)palladium, dichlorobis(acetonitrile)palladium, dichlorobis(benzonitrile)palladium and other complex compounds, and dichlorobis(triphenylphosphine)palladium, tetrakis(triphenylphosphine)palladium, dichloro[1,1'-bis(diphenylphosphino)ferrocene]palladium, bis(tri-tert-butylphosphine)palladium, bis(tricyclohexylphosphine)palladium, dichlorobis(tricyclohexylphosphine)palladium and other palladium complexes having a tertiary phosphine as a ligand can be exemplified.

[0201] A palladium complex having a tertiary phosphine as a ligand can also be prepared in a reaction system by adding a tertiary phosphine to a palladium salt or complex compound. Examples of the tertiary phosphine that can be used in this case include 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.

[0202] Among these, a palladium complex having a tertiary phosphine as a ligand is preferable in terms of good yield, and a palladium complex having 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl or triphenylphosphine as a ligand is more preferable.

[0203] The molar ratio of the tertiary phosphine to the palladium salt or complex compound is preferably in the range of 1:10 to 10:1, and more preferably in the range of 1:2 to 3:1 in terms of good yield. Although there is no limit to the amount of the palladium catalyst used in the coupling reaction, in terms of good yield, the molar equivalent of the palladium catalyst is preferably in the range of 0.005 to 0.5 molar equivalent with respect to the boron compound.

[0204] The base used in the aforementioned coupling reaction and borylation reaction is not particularly limited. For example, metal hydroxide salts such as sodium hydroxide, potassium hydroxide, and calcium hydroxide; metal carbonate salts such as sodium carbonate, potassium carbonate, lithium carbonate, and cesium carbonate; metal acetate salts such as potassium acetate and sodium acetate; metal phosphate salts such as potassium phosphate and sodium phosphate; metal fluoride salts such as sodium fluoride, potassium fluoride, and cesium fluoride; metal alkoxides such as sodium methoxide, potassium methoxide, sodium ethoxide, potassium isopropyl oxide, and potassium tert-butoxide can be mentioned.

[0205] Among them, metal carbonate salts and metal phosphate salts are preferred in terms of good reaction yield, and potassium carbonate or potassium phosphate is more preferred. There is no particular limitation on the amount of the base, but in terms of good reaction yield, the molar ratio of the base to the boron compound is preferably in the range of 1:2 to 10:1, and more preferably in the range of 1:1 to 4:1.

[0206] The above-mentioned coupling reaction and borylation reaction can be carried out in a solvent. Examples of the solvent include ethers such as water, diisopropyl ether, dibutyl ether, cyclopentyl methyl ether (CPME), tetrahydrofuran (THF), 2-methyltetrahydrofuran, 1,4-dioxane, and dimethoxyethane; aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, and tetralin; carbonates such as ethylene carbonate, propylene carbonate, dimethyl carbonate, diethyl carbonate, ethyl methyl carbonate, and 4-fluoroethylene carbonate; esters such as ethyl acetate, butyl acetate, methyl propionate, ethyl propionate, methyl butyrate, and γ-lactone; amides such as N,N-dimethylformamide (DMF), dimethylacetamide (DMAc), and N-methylpyrrolidone (NMP); ureas such as N,N,N’,N’-tetramethylurea (TMU) and N,N’-dimethylpropyleneurea (DMPU); dimethyl sulfoxide (DMSO); and alcohols such as methanol, ethanol, isopropyl alcohol, butanol, octanol, benzyl alcohol, ethylene glycol, propylene glycol, diethylene glycol, triethylene glycol, and 2,2,2-trifluoroethanol. These can be used by mixing them in an arbitrary ratio. There is no particular limitation on the amount of the solvent used. Among these, water, ether, amide, alcohol, or a mixed solvent thereof is preferable in terms of good reaction yield, and a mixed solvent of THF and water is more preferable.

[0207] The above-mentioned coupling reaction and borylation reaction can be carried out at a temperature appropriately selected from 0 °C to 200 °C, and it is preferable to carry out the reaction at a temperature appropriately selected from 40 °C to 150 °C in terms of good reaction yield.

[0208] The above-mentioned coupling reaction and borylation reaction can be obtained by performing ordinary treatment after the completion of the reaction. If necessary, the target product can be obtained by appropriately combining general purification treatments such as recrystallization, column chromatography, sublimation, or preparative HPLC as needed.

[0209] <Electron transport material> The electron transport material according to one aspect of the present invention contains an adamantane compound according to another aspect of the present invention.

[0210] The adamantane compound (1) is useful as an electron transport material. The adamantane compound (1) can be used, for example, as an electron transport material for an organic light-emitting device. The electron transport material containing the adamantane compound (1) exhibits long life and high luminous efficiency characteristics, and can produce an organic light-emitting device that can be used in various applications or various environments.

[0211] The electron transport material has a function of transmitting electrons injected from the cathode to the light-emitting layer. By interposing the electron transport material between the cathode and the light-emitting layer, electrons are injected into the light-emitting layer at a lower electric field. In addition, the electron transport material may have a function as a hole blocking layer. The hole blocking layer is a layer that prevents holes and excitons from entering from the light-emitting layer to the electron transport layer and / or assists electron injection from the electron transport layer to the light-emitting layer.

[0212] Examples of conventionally known electron transporting materials include, but are not particularly limited to, alkali metal complexes, alkaline earth metal complexes, earth metal complexes, rare earth metals, etc. Examples of alkali metal complexes, alkaline earth metal complexes, earth metal complexes, rare earth metals, and organic compounds include lithium 8-hydroxyquinolinate (Liq), zinc bis(8-hydroxyquinolinate), copper bis(8-hydroxyquinolinate), manganese bis(8-hydroxyquinolinate), aluminum tris(8-hydroxyquinolinate), aluminum tris(2-methyl-8-hydroxyquinolinate), gallium tris(8-hydroxyquinolinate), beryllium bis(10-hydroxybenzo[h]quinolinate), zinc bis(10-hydroxybenzo[h]quinolinate), chloro gallium bis(2-methyl-8-quinolinolate), gallium bis(2-methyl-8-quinolinolate)(o-cresolate), aluminum bis(2-methyl-8-quinolinolate)-1-naphtholate, gallium bis(2-methyl-8-quinolinolate)-2-naphtholate, ytterbium, triazine compounds, pyrimidine compounds, pyridine compounds, anthracene compounds, and the like.

[0213] As described above, the electron transporting material preferably contains the adamantane compound (1). The electron transporting material may be used alone as the adamantane compound (1), or may contain one or more selected from conventionally known electron transporting materials in addition to the adamantane compound (1). The electron transporting material preferably contains the adamantane compound (1) and lithium 8-hydroxyquinolinate (Liq), aluminum tris(8-hydroxyquinolinate), or ytterbium. The weight ratio of the adamantane compound (1) to the metal complex and the rare earth metal in the electron transporting material is preferably from 1:10 to 10:1, and more preferably from 3:7 to 7:3 in terms of excellent electron transporting properties. <Organic light-emitting device>

[0214] Hereinafter, an organic light-emitting device having a layer containing the adamantane compound (1) (hereinafter sometimes simply referred to as an organic light-emitting device) will be described.

[0215] An organic light-emitting device according to one aspect of the present invention includes a first electrode, a second electrode provided opposite to the first electrode, and an organic light-emitting device including a plurality of organic layers provided between the first electrode and the second electrode, wherein one or more of the plurality of organic layers contain an adamantane compound according to another aspect of the present invention.

[0216] The configuration of the organic light-emitting device is not particularly limited, and examples thereof include the configurations of (i) to (v) shown below. (i): Anode / Light-emitting layer / Cathode (ii): Anode / Hole transport layer / Light-emitting layer / Cathode (iii): Anode / Light-emitting layer / Electron transport layer / Cathode (iv): Anode / Hole transport layer / Light-emitting layer / Electron transport layer / Cathode (v): Anode / Hole injection layer / Hole transport layer / Light-emitting layer / Electron transport layer / Electron injection layer / Cathode (vi): Anode / Hole injection layer / Hole transport layer / Light-emitting layer / Hole blocking layer / Electron transport layer / Electron injection layer / Cathode

[0217] Here, one of the anode and the cathode corresponds to the first electrode, and the other corresponds to the second electrode. The hole injection layer, the hole transport layer, the light-emitting layer, the electron transport layer, the hole blocking layer, and the electron injection layer provided between the first electrode and the second electrode, as well as other layers provided as necessary, correspond to the organic layers.

[0218] The adamantane compound (1) may be contained in any of the above layers, but is preferably contained in one or more selected from the group consisting of the light-emitting layer and the layer between the light-emitting layer and the cathode in terms of excellent light-emitting characteristics of the organic light-emitting device.

[0219] Therefore, in the case of the configurations shown in (i) to (v) above, it is preferable that the adamantane compound (1) is contained in one or more selected from the group consisting of the light-emitting layer, the electron transport layer, and the electron injection layer.

[0220] Hereinafter, the organic light-emitting device according to one embodiment of the present invention will be described in more detail with reference to FIG. 1 by taking the configuration of the above (vi) as an example.

[0221] Note that the organic light-emitting device shown in FIG. 1 has a so-called bottom emission type element configuration, but the organic light-emitting device according to one embodiment of the present invention is not limited to the bottom emission type element configuration. That is, the organic light-emitting device according to one embodiment of the present invention may have other known element configurations such as a top emission type.

[0222] There is no particular limitation on the method for manufacturing the thin film for an organic light-emitting device composed of the adamantane compound (1), but film formation by a vacuum evaporation method is possible. Film formation by a vacuum evaporation method can be performed by using a general-purpose vacuum evaporation apparatus. Considering the production tact time and production cost of manufacturing an organic light-emitting device, the degree of vacuum in the vacuum chamber when forming a film by a vacuum evaporation method is generally 1×10 -2 ~1×10 -5 ~1×10 -6 Pa or so is preferable, and more preferably 1×10 -3 ~10 -6 Pa. The evaporation rate depends on the thickness of the film to be formed, but is preferably 0.005 to 1.0 nm / second, and more preferably 0.01 to 1 nm / second. Further, since the adamantane compound (1) has high solubility in chloroform, dichloromethane, 1,2-dichloroethane, chlorobenzene, toluene, ethyl acetate, tetrahydrofuran, etc., film formation by a spin coating method, an inkjet method, a casting method, a dipping method, etc. using a general-purpose apparatus is also possible.

[0223] FIG. 1 is a schematic cross-sectional view showing an example of the laminated structure of an organic light-emitting device containing an adamantane compound according to one embodiment of the present invention.

[0224] The organic light-emitting device 100 includes a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, an electron injection layer 7, and a cathode 8 in this order. However, some of these layers may be omitted, and conversely, other layers may be added. For example, a hole blocking layer 9 may be provided between the light-emitting layer 5 and the electron transport layer 6, the hole injection layer 3 may be omitted, and the hole transport layer 4 may be directly provided on the anode 2.

[0225] Further, for example, a single layer having functions of a plurality of layers, such as an electron injection / transport layer having functions of an electron injection layer and an electron transport layer in a single layer, may be provided instead of the plurality of layers. Furthermore, for example, a single-layer hole transport layer 4 and a single-layer electron transport layer 6 may each be composed of a plurality of layers. [[Layer containing adamantane compound (1)]]

[0226] In the configuration example shown in FIG. 1, the organic light-emitting device 100 contains the adamantane compound (1) in at least one layer selected from the group consisting of the light-emitting layer 5, the electron transport layer 6, and the electron injection layer 7. In particular, it is preferable that the electron transport layer 6 contains the adamantane compound (1). The adamantane compound (1) may be contained in a plurality of layers included in the organic light-emitting device.

[0227] Hereinafter, as one of the preferred embodiments, the organic light-emitting device 100 in which the electron transport layer 6 contains the adamantane compound (1) will be described. [Substrate 1]

[0228] The substrate 1 is not particularly limited, and examples thereof include a glass plate, a quartz plate, and a plastic plate.

[0229] 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 light-transmissive plastic film are preferable.

[0230] Examples of the light-transmissive plastic film include films made of 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.

[0231] In the case of a configuration in which light emission is extracted from the substrate 1 side, the substrate 1 is transparent to the wavelength of light. [Anode 2]

[0232] An anode 2 is provided on the substrate 1 (on the hole injection layer 3 side).

[0233] Examples of the anode material include metals, alloys, electrically conductive compounds, and mixtures thereof having a large work function (for example, 4 eV or more). Specific examples of the anode material include metals such as Au; and conductive transparent materials such as CuI, indium tin oxide (ITO), SnO2, and ZnO.

[0234] In the case of an organic light-emitting element having a configuration in which light emission passes through the anode and is extracted, the anode is formed of a conductive transparent material that passes or substantially passes the light emission. [Hole injection layer 3, hole transport layer 4]

[0235] Between the anode 2 and the light-emitting layer 5, a hole injection layer 3 and a hole transport layer 4 are provided in this order from the anode 2 side.

[0236] The hole injection layer and the hole transport layer have a function of transmitting holes injected from the anode to the light-emitting layer. By interposing the hole injection layer and the hole transport layer between the anode and the light-emitting layer, more holes are injected into the light-emitting layer at a lower electric field.

[0237] In addition, the hole injection layer and the hole transport layer also function as electron blocking layers. 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 suppressed from leaking into the hole injection layer and / or the hole transport layer by the electron barrier existing at the interface between the light-emitting layer and the hole injection layer and / or the hole transport layer. As a result, the electrons are accumulated at the interface within the light-emitting layer, bringing about effects such as improved light-emitting efficiency, and an organic light-emitting device with excellent light-emitting performance can be obtained.

[0238] As materials for the hole injection layer and the hole transport layer, those having at least any one of hole injection property, hole transport property, and electron blocking property are used. The materials for the hole injection layer and the hole transport layer may be either organic substances or inorganic substances.

[0239] Specific examples of the materials for the hole injection layer and the hole transport layer include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline-based copolymers, conductive polymer oligomers (especially thiophene oligomers), porphyrin compounds, aromatic tertiary amine compounds, styrylamine compounds, and the like.

[0240] Among these, porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds are preferable in terms of the good performance of the organic light-emitting device, and aromatic tertiary amine compounds are particularly preferable.

[0241] Specific examples of the aromatic tertiary amine compound and the styrylamine compound 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-tolylaminophenyl)-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)quarterphenyl, 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-diphenylaminostilbene, 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.

[0242] In addition, inorganic compounds such as p-type Si and p-type SiC can also be cited as an example of the material for the hole injection layer and the material for the hole transport layer.

[0243] The hole injection layer and 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 of the same composition or different compositions.

[0244] A charge generation layer may be provided between the hole injection layer and the hole transport layer. The material of the charge generation layer is not particularly limited. For example, dipyrido[2,3-f:2’,3’-h]quinoxaline-2,3,6,7,10,11-hexacarbonitrile (HAT-CN) can be mentioned. The charge generation 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 of the same composition or different compositions. [Light-emitting layer 5]

[0245] A light-emitting layer 5 is provided between the hole transport layer 4 and the electron transport layer 6.

[0246] Examples of the material of the light-emitting layer include phosphorescent materials, fluorescent materials, and thermally activated delayed fluorescent materials. In the light-emitting layer, electron-hole pairs recombine, and as a result, light emission occurs.

[0247] The light-emitting layer may be composed of a single low-molecular material or a single polymer material. More generally, however, it is composed of a host material doped with a guest compound. Light emission mainly occurs from the dopant and can have any color.

[0248] Examples of the host material include compounds having a biphenylyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, and an anthryl group. More specifically, DPVBi (4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl), BCzVBi (4,4'-bis(9-ethyl-3-carbazolvinylene)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, etc. can be mentioned.

[0249] Examples of the fluorescent dopant include anthracene, pyrene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylene pyran compounds, thiopyran compounds, polymethine compounds, pyrylium, thiapyrylium compounds, fluorene derivatives, periflanthene derivatives, indenoperylene derivatives, bis(azinyl)amine boron compounds, bis(azinyl)methane compounds, carbostyryl compounds, boron compounds, cyclic amine compounds, etc. The fluorescent dopant may be a combination of two or more selected from these.

[0250] Examples of the phosphorescent dopant include organometallic complexes of transition metals such as iridium, platinum, palladium, osmium, etc.

[0251] Specific examples of the fluorescent dopant and the phosphorescent dopant 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))), etc.

[0252] Further, the light-emitting material is not limited to being contained only in the light-emitting layer. For example, the light-emitting material may be contained in a layer adjacent to the light-emitting layer (the hole transport layer 4 or the electron transport layer 6). Thereby, the light-emitting efficiency of the organic light-emitting device can be further increased.

[0253] 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 of the same composition or different compositions. [Electron transport layer 6]

[0254] An electron transport layer 6 is provided between the light-emitting layer 5 and the electron injection layer 7.

[0255] The electron transport layer has a function of transmitting electrons injected from the cathode to the light-emitting layer. By interposing the electron transport layer between the cathode and the light-emitting layer, electrons are injected into the light-emitting layer at a lower electric field.

[0256] Although not particularly limited, examples of conventionally known electron transporting materials include alkali metal complexes, alkaline earth metal complexes, earth metal complexes, rare earth metals, etc. Examples of alkali metal complexes, alkaline earth metal complexes, earth metal complexes, rare earth metals, and organic compounds include lithium 8-hydroxyquinolinate (Liq), zinc bis(8-hydroxyquinolinate), copper bis(8-hydroxyquinolinate), manganese bis(8-hydroxyquinolinate), aluminum tris(8-hydroxyquinolinate), aluminum tris(2-methyl-8-hydroxyquinolinate), gallium tris(8-hydroxyquinolinate), beryllium bis(10-hydroxybenzo[h]quinolinate), zinc bis(10-hydroxybenzo[h]quinolinate), chloro gallium bis(2-methyl-8-quinolinolate), gallium bis(2-methyl-8-quinolinolate)(o-cresolate), aluminum bis(2-methyl-8-quinolinolate)-1-naphtholate, gallium bis(2-methyl-8-quinolinolate)-2-naphtholate, ytterbium, triazine compounds, pyrimidine compounds, pyridine compounds, anthracene compounds, and the like.

[0257] The electron transport layer may further contain one or more selected from conventionally known electron transport materials in addition to the adamantane compound (1). The electron transport layer preferably contains the adamantane compound (1) and lithium 8-hydroxyquinolinate (Liq), aluminum tris(8-hydroxyquinolinate), or ytterbium. The weight ratio of the adamantane compound (1) to the metal complex and the rare earth metal in the electron transport layer is preferably from 1:10 to 10:1, and more preferably from 3:7 to 7:3 in terms of excellent electron transport characteristics.

[0258] In addition, when the adamantane compound (1) is not included in the electron transport layer but is included in other layers, one or more selected from conventionally known electron transport materials can be used as the electron transport material constituting the electron transport layer. It is preferable that the electron transport layer contains lithium 8-hydroxyquinolinate (Liq), tris(8-hydroxyquinolinate)aluminum, and ytterbium.

[0259] The electron transport 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 of the same composition or different compositions. [Hole blocking layer 9]

[0260] A hole blocking layer 9 may be provided between the light-emitting layer 5 and the electron transport layer 6. The hole blocking layer is a layer that prevents the intrusion of holes and excitons from the light-emitting layer into the electron transport layer and / or assists the injection of electrons from the electron transport layer into the light-emitting layer. Conventionally known hole blocking materials include, but are not particularly limited to, triazine compounds, pyrimidine compounds, pyridine compounds, carbazole compounds, anthracene compounds, (2-[3’-(2-triphenylenyl)-[1,1’-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine, 2-[3’-(9,9-dimethyl-9H-fluoren-2-yl)[1,1’-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine, 2,4,6-tris(biphenyl-3-yl)-1,3,5-triazine, and the like.

[0261] The hole blocking layer 9 preferably contains the adamantane compound (1). The hole blocking layer is used alone with the adamantane compound (1) or preferably contains lithium 8-hydroxyquinolinate (Liq), tris(8-hydroxyquinolinate)aluminum, and ytterbium. The weight ratio of the adamantane compound (1) to the metal complex and the rare earth metal in the hole blocking layer is preferably from 1:10 to 10:1, and more preferably from 3:7 to 7:3 in terms of excellent electron transport characteristics.

[0262] The hole-blocking layer may contain a known hole-blocking material other than the adamantane compound (1) and an electron transport auxiliary material. The hole-blocking layer may be used alone with a known hole-blocking material or preferably contains lithium 8-hydroxyquinolinate (Liq), tris(8-hydroxyquinolinate)aluminum, or ytterbium.

[0263] In the organic light-emitting device according to one aspect of the present invention, an electron injection layer may be provided for the purpose of improving electron injectability and improving device characteristics (e.g., luminous efficiency, low-voltage driving, or high durability). [Electron injection layer 7]

[0264] An electron injection layer 7 is provided between the electron transport layer 6 and the cathode 8. The electron injection layer has a function of transmitting electrons injected from the cathode to the light-emitting layer. By interposing the electron injection layer between the cathode and the light-emitting layer, electrons are injected into the light-emitting layer at a lower electric field.

[0265] Examples of the material for the electron injection layer include organic compounds such as fluorenone, anthraquinodimethane, diphenoquinone, thiopyrandioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, and anthrone.

[0266] In addition, examples of the material for the electron injection layer also include inorganic compounds such as various oxides, fluorides, nitrides, and oxynitrides such as SiO2, AlO, SiN, SiON, AlON, GeO, LiO, LiON, TiO, TiON, TaO, TaON, TaN, LiF, C, and Yb. [Cathode 8]

[0267] A cathode 8 is provided on the electron injection layer 7. In the case of an organic electroluminescence device configured to extract only the light that has passed through the anode, the cathode can be formed from any conductive material.

[0268] Examples of the cathode material include metals with a small work function (hereinafter also referred to as electron-injecting metals), alloys, electrically conductive compounds, and mixtures thereof. Here, the metal with a small work function is, for example, a metal with a work function of 4 eV or less.

[0269] Specific examples of the cathode material include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al2O3) mixture, indium, lithium / aluminum mixture, rare earth metals, and the like.

[0270] Among these, from the viewpoints of electron injection property and durability against oxidation and the like, a mixture of an electron-injecting metal and a second metal which is a metal having a larger work function value and higher stability than this, for example, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / aluminum oxide (Al2O3) mixture, lithium / aluminum mixture, and the like are preferable. [Method for forming each layer]

[0271] Each layer except the electrodes (anode, cathode) described above can be formed by thinning into a thin film by a known method such as a vacuum evaporation method, a spin coating method, a casting method, an LB (Langmuir-Blodgett method), or the like. The material of each layer may be used alone, or may be used together with a material such as a binder resin and a solvent as necessary.

[0272] There is no particular limitation on the film thickness of each layer formed in this way, and it can be appropriately selected according to the situation, but it is usually in the range of 5 nm to 5 μm.

[0273] The anode and the cathode can be formed by thinning the electrode material into a thin film by methods such as vapor deposition or sputtering. A pattern may be formed through a mask of a desired shape during vapor deposition or sputtering, or after forming a thin film by vapor deposition, sputtering, etc., a pattern of a desired shape may be formed by photolithography.

[0274] The film thickness of the anode and the cathode is preferably 1 μm or less, and more preferably 10 nm or more and 200 nm or less.

[0275] In addition, when forming the layer containing the adamantane compound (1), it may be used in combination with the above-mentioned conventionally known electron transporting material. Therefore, for example, the adamantane compound (1) and the conventionally known electron transporting material may be co-evaporated, or a layer of the conventionally known electron transporting material may be laminated on the layer of the adamantane compound (1).

[0276] The organic light-emitting element may be used as a kind of lamp such as for lighting or an exposure light source, or as a projection device of a type that projects an image onto a screen or the like, or a display device (display) of a type that directly visually recognizes a still image or a moving image.

[0277] When using the organic light-emitting element as a display device for video playback, the driving method may be a simple matrix (passive matrix) method or an active matrix method. Further, by using two or more organic light-emitting elements having different emission colors, a full-color display device can be manufactured.

[0278] When the adamantane compound (1) is used as an electron transport layer, an organic light-emitting element having significantly excellent luminous efficiency and lifetime characteristics compared to conventionally known adamantane compounds can be provided. Further, the adamantane compound (1) has high amorphousness due to its bulky three-dimensional skeleton and has high film quality stability.

Examples

[0279] Hereinafter, the present invention will be described in more detail based on examples, but the present invention should not be construed as being limited in any way by these examples.

[0280] 1 1H-NMR measurement] 1 For the measurement of 1H-NMR, AVANCE III HD 400 (400 MHz; manufactured by BRUKER) and AVANCE III 400 (400 MHz; manufactured by BRUKER) were used. 1 1H-NMR was measured using deuterated chloroform (CDCl3) as the measurement solvent and tetramethylsilane (TMS) as the internal standard substance. Commercially available products were used for the reagents.

[0281] [DSC measurement (glass transition temperature, crystallization temperature, melting point)] The measurements of the glass transition temperature, crystallization temperature, and melting point were performed using DSC7020 (manufactured by Hitachi High-Tech Sciences Corporation, product name).

[0282] The measurement conditions for DSC are as follows. The measurement was carried out under a nitrogen atmosphere (flow rate: 50 mL / min). It was performed in the order of first cooling and second heating, and the glass transition temperature, crystallization temperature, and melting point during the second heating were taken as the glass transition temperature, crystallization temperature, and melting point of the sample, respectively. Sample amount: 5 - 10 mg Measurement conditions: <First heating> Heating rate: 15 °C / min Measurement temperature range: 30 °C - 360 °C <First cooling> Quenching with dry ice <Second heating> Heating rate: 5 °C / min Measurement temperature range: 30 °C - 360 °C

[0283] Synthesis Example - 1 (Compound - 1 - 1)

[0284]

Chemical formula

[0285] Under an argon atmosphere, 2,4-diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine (946 mg, 2.14 mmol), 3-(4-biphenylyl)-1-(4-trifluoromethanesulfonyloxyphenyl)adamantane (1.23 g, 2.39 mmol), palladium acetate (14.6 mg, 0.0650 mmol), and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (62.2 mg, 0.130 mmol) were suspended in THF (22 mL). To this suspension, 2.0 M aqueous potassium phosphate solution (3.26 mL, 6.52 mmol) was added, and the mixture was heated under reflux at 80 °C for 24 hours. After allowing to cool to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was dissolved in chloroform, activated carbon was added, and the mixture was stirred at 70 °C for 30 minutes, then allowed to cool and filtered through celite. The low-boiling components were distilled off under reduced pressure from the filtrate, and the obtained solid was purified by column chromatography (hexane / chloroform) to obtain the target 4,6-diphenyl-2-[4′-{3-(4-biphenylyl)adamantan-1-yl}biphenyl-3-yl]-1,3,5-triazine as a white solid (yield 1.06 g, yield 74%). 1 1H-NMR (400 MHz, CDCl3) δ (ppm): 9.01 (t, J = 1.6 Hz, 1H), 8.78 - 8.82 (m, 4H), 8.75 (dt, J = 7.8, 1.4 Hz, 1H), 7.84 (ddd, J = 7.7, 1.8, 1.3 Hz, 1H), 7.71 - 7.76 (m, 2H), 7.56 - 7.67 (m, 13H), 7.51 (dt, J = 8.5, 2.3 Hz, 2H), 7.40 - 7.46 (m, 2H), 7.33 (tt, J = 7.3, 1.8 Hz, 1H), 2.40 (brs, 2H), 2.18 (s, 2H), 2.06 (dd, J = 8.2, 2.5 Hz, 8H), 1.86 (brs, 2H).

[0286] Synthesis Example - 2 (Compound - 1 - 22)

[0287] [Chem.]

[0288] Under an argon atmosphere, 2,4-diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-1,3,5-triazine (578 mg, 1.33 mmol), 4-(3-(4-[6-phenylpyridin-3-yl]phenyl)adamantan-1-yl)phenyl trifluoromethanesulfonate (860 mg, 1.46 mmol), palladium acetate (8.9 mg, 40 μmol), and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (38.0 mg, 79.6 μmol) were suspended in THF (15 mL). To this suspension, 2.0 M aqueous potassium phosphate solution (1.99 mL, 3.98 mmol) was added, and the mixture was heated under reflux at 80 °C for 24 hours. After allowing to cool to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was dissolved in chloroform, activated carbon was added, and the mixture was stirred at 70 °C for 30 minutes, then allowed to cool and filtered through celite. The low-boiling components were distilled off under reduced pressure from the filtrate, and the obtained solid was purified by recrystallization (toluene) to give the target 2-(4′-(3-(4-[6-phenylpyridin-3-yl]phenyl)adamantan-1-yl)-[1,1′-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine as a white solid (yield 847 mg, 77% yield). 11H-NMR (400 MHz, CDCl3) δ (ppm): 9.01 (t, J = 1.7 Hz, 1H), 8.95 (dd, J = 2.3, 0.6 Hz, 1H), 8.77 - 8.82 (m, 4H), 8.75 (dt, J = 7.8, 1.4 Hz, 1H), 8.02 - 8.07 (m, 2H), 7.97 (dd, J = 8.2, 2.4 Hz, 1H), 7.84 (ddd, J = 7.6, 1.8, 1.2 Hz, 1H), 7.81 (dd, J = 8.2, 0.6 Hz, 1H), 7.71 - 7.76 (m, 2H), 7.55 - 7.67 (m, 13H), 7.47 - 7.53 (m, 2H), 7.81 (tt, J = 7.2, 2.2 Hz, 1H), 2.41 (brs, 2H), 2.18 (s, 2H), 2.07 (dd, J = 8.5, 2.4 Hz, 8H), 1.87 (brs, 2H).

[0289] Synthesis Example - 3 (Compound - 1 - 94)

[0290] [Chemical Structure]

[0291] Under an argon atmosphere, 2,4-diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-1,3,5-triazine (258 mg, 0.592 mmol), 4-(3-(4'-cyano-[1,1'-biphenyl]-4-yl)adamantan-1-yl)phenyl trifluoromethanesulfonate (350 mg, 0.651 mmol), palladium acetate (4.0 mg, 18 μmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (16.9 mg, 35.5 μmol) were suspended in THF (6.0 mL). To this suspension was added an aqueous solution of 2.0 M potassium phosphate (0.898 mL, 1.78 mmol), and the mixture was heated under reflux at 80 °C for 24 hours. After allowing to cool to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was dissolved in chloroform, activated carbon was added, and the mixture was stirred at 70 °C for 30 minutes, then allowed to cool and filtered through celite. The low-boiling components were distilled off under reduced pressure from the filtrate, and the obtained solid was purified by recrystallization (toluene) to obtain the target 2-(4'-(3-(4'-cyano-[1,1'-biphenyl]-4-yl)adamantan-1-yl)-[1,1'-biphenyl]-3-yl)-4,6-diphenyl-1,3,5-triazine as a white solid (yield 309 mg, yield 75%). 1 1H-NMR (400 MHz, CDCl3) δ (ppm): 9.00 (brs, 1H), 8.78 - 8.82 (m, 4H), 8.75 (d, J = 7.8 Hz, 1H), 7.84 (d, J = 7.8 Hz, 1H), 7.51 - 7.76 (m, 19H), 2.41 (brs, 2H), 2.16 (brs, 2H), 2.03 - 2.10 (m, 8H), 1.87 (brs, 2H).

[0292] Synthesis Example - 4 (Compound - 1 - 49)

[0293]

Chemical Structure

[0294] Under an argon atmosphere, 4,6-diphenyl-2-[4’-{3-(4-trifluoromethanesulfonyloxyphenyl)adamantan-1-yl}-biphenyl-3-yl]-1,3,5-triazine (100 mg, 0.134 mmol), diphenyl[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)phosphine oxide (65.1 mg, 0.161 mmol), palladium acetate (1.5 mg, 6.7 μmol) and 2-dicyclohexylphosphino-2’,4’,6’-triisopropylbiphenyl (6.3 mg, 0.013 mmol) were suspended in THF (1.3 mL). To this suspension was added an aqueous solution of 2.0 M potassium carbonate (0.201 mL, 0.402 mmol), and the mixture was heated under reflux at 80 °C for 14 hours. After allowing to cool to room temperature, water was added to the reaction mixture, and the mixture was extracted with chloroform and dried over sodium sulfate. The solvent was distilled off, and the resulting solid was dissolved in chloroform. Activated carbon was added and the mixture was stirred for 30 minutes, followed by filtration through celite. The low-boiling components were distilled off under reduced pressure from the filtrate, and the resulting solid was purified by column chromatography (hexane / chloroform) to obtain the desired 4,6-diphenyl-2-[4’-{3-(4’-(diphenylphosphine oxide)-1,1’-biphenyl-4-yl)adamantan-1-yl}-biphenyl-3-yl]-1,3,5-triazine as a white solid (yield 79.0 mg, yield 68%). 1 1H-NMR (400 MHz, CDCl3) δ (ppm): 9.00 (t, J = 1.7 Hz, 1H), 8.78 - 8.81 (m, 4H), 8.75 (dt, J = 7.8, 1.3 Hz, 1H), 7.84 (dt, J = 7.5, 1.5 Hz, 1H), 7.67 - 7.75 (m, 10H), 7.54 - 7.66 (m, 14H), 7.46 - 7.52 (m, 5H), 2.40 (brs, 2H), 2.16 (s, 2H), 2.06 (dd, J = 11.7, 1.7 Hz, 8H), 1.86 (brs, 2H).

[0295] Synthesis Example - 5 (Compound - 1 - 3)

[0296]

Chemical Structure

[0297] Under an argon atmosphere, 4,6-diphenyl-2-[4’-{3-(4-trifluoromethanesulfonyloxyphenyl)adamantan-1-yl}-biphenyl-3-yl]-1,3,5-triazine (100 mg, 0.134 mmol), 9-phenanthreneboronic acid (35.8 mg, 0.161 mmol), palladium acetate (1.5 mg, 6.7 μmol) and 2-dicyclohexylphosphino-2’,4’,6’-triisopropylbiphenyl (6.3 mg, 0.013 mmol) were suspended in THF (1.3 mL). To this suspension, 2.0 M aqueous potassium carbonate solution (0.201 mL, 0.402 mmol) was added, and the mixture was heated to reflux at 80 °C for 14 hours. After cooling to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was dissolved in chloroform, activated carbon was added, and the mixture was stirred for 30 minutes, followed by filtration through celite. The low-boiling components were distilled off under reduced pressure from the filtrate, and the obtained solid was purified by recrystallization (toluene) to obtain the target 4,6-diphenyl-2-[4’-{3-(4-(phenanthren-9-yl)phenyl)adamantan-1-yl}-biphenyl-3-yl]-1,3,5-triazine as a white solid (yield 30.0 mg, yield 29%). 1 1H-NMR (400 MHz, CDCl3) δ (ppm): 9.02 (t, J = 1.7 Hz, 1H), 8.74 - 8.82 (m, 6H), 8.72 (d, J = 8.2 Hz, 1H), 7.99 (dd, J = 8.2, 1.0 Hz, 1H), 7.89 (dd, J = 7.7, 1.3 Hz, 1H), 7.84 - 7.87 (m, 1H), 7.75 (d, J = 8.3 Hz, 2H), 7.53 - 7.70 (m, 18H), 2.44 (brs, 2H), 2.24 (s, 2H), 2.12 (dd, J = 5.9, 2.2 Hz, 8H), 1.90 (brs, 2H).

[0298] Synthesis Example - 6 (Compound - 1 - 41)

[0299]

Chemical Structure

[0300] Under an argon atmosphere, 2,4-diphenyl-6-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl]-1,3,5-triazine (122 mg, 0.269 mmol), 3-[4-(dibenzofuran-4-yl)phenyl]-1-(4-trifluoromethanesulfonyloxyphenyl)-adamantane (147 mg, 0.244 mmol), palladium acetate (2.69 mg, 0.0122 mmol) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (11.2 mg, 0.0244 mmol) were suspended in THF (2.7 mL). To this suspension was added an aqueous solution of 2.0 M potassium carbonate (0.404 mL, 0.807 mmol), and the mixture was heated under reflux at 80 °C for 15 h. After allowing to cool to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was dissolved in chloroform, activated carbon was added, and the mixture was stirred for 30 min, followed by filtration through celite. The low-boiling components were distilled off under reduced pressure from the filtrate, and the obtained solid was purified by column chromatography (hexane / chloroform) to obtain the target 4,6-diphenyl-2-[4′-{3-(4-(dibenzofuran-4-yl)-phenyl)adamantan-1-yl}-biphenyl-3-yl]-1,3,5-triazine as a white solid (yield 101 mg, 49% yield). 1 1H-NMR (400 MHz, CDCl3) δ (ppm): 9.02 (t, J = 1.6 Hz, 1H), 8.79 - 8.82 (m, 4H), 8.76 (dt, J = 7.8, 1.3 Hz), 8.00 (d, J = 7.7 Hz, 1H), 7.92 - 7.94 (m, 3H), 7.85 (dt, J = 7.8, 1.4 Hz, 1H), 7.75 (d, J = 8.5 Hz, 2H), 7.66 (d, J = 7.7 Hz, 1H), 7.57 - 7.63 (m, 12H), 7.41 - 7.49 (m, 2H), 7.36 (dt, J = 7.4, 0.8 Hz, 1H), 2.42 (brs, 2H), 2.23 (s, 2H), 2.10 (brs, 8H), 1.89 (brs, 2H).

[0301] Synthesis Example - 7 (Compound - 1 - 5)

[0302]

Chem.

[0303] Under an argon atmosphere, 4,6-diphenyl-2-[4’-{3-(4-trifluoromethanesulfonyloxyphenyl)adamantan-1-yl}-biphenyl-3-yl]-1,3,5-triazine (100 mg, 0.134 mmol), 1,1’:4’,1’’-terphenyl-4-ylboronic acid (44.1 mg, 0.160 mmol), palladium acetate (1.5 mg, 6.7 μmol), and 2-dicyclohexylphosphino-2’,4’,6’-triisopropylbiphenyl (6.3 mg, 0.013 mmol) were suspended in THF (1.3 mL). To this suspension was added 2.0 M aqueous potassium carbonate solution (0.201 mL, 0.402 mmol), and the mixture was heated to reflux at 80 °C for 14 h. After allowing to cool to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was dissolved in chloroform, activated carbon was added, and the mixture was stirred for 30 min, followed by filtration through celite. The low-boiling components were distilled off under reduced pressure from the filtrate, and the obtained solid was purified by recrystallization (toluene) to give the target 4,6-diphenyl-2-[4’-{3-(4-(1,1’:4’,1’’:4’’,1’’’-quaterphenyl)adamantan-1-yl)-biphenyl-3-yl]-1,3,5-triazine as a white solid (yield 74.0 mg, yield 67%). 1 1H-NMR (400 MHz, CDCl3) δ (ppm): 9.01 (t, J = 1.7 Hz, 1H), 8.78 - 8.81 (m, 4H), 8.75 (dt, J = 7.8, 1.3 Hz, 1H), 7.83 - 7.86 (m, 1H), 7.66 - 7.75 (m, 10H), 7.57 - 7.67 (m, 13H), 7.54 (d, J = 8.5 Hz, 2H), 7.47 (t, J = 7.5 Hz, 2H), 7.37 (tt, J = 6.7, 1.3 Hz, 1H), 2.41 (brs, 2H), 2.19 (s, 2H), 2.08 (dd, J = 5.8, 2.3 Hz, 8H), 1.87 (brs, 2H).

[0304] Synthesis Example - 8 (Compound - 1 - 14)

[0305]

Chemical Structure

[0306] Under an argon atmosphere, 4,6 - diphenyl - 2 - [4’ - {3 - (4 - trifluoromethanesulfonyloxyphenyl)adamantan - 1 - yl}-biphenyl - 3 - yl]-1,3,5 - triazine (100 mg, 0.134 mmol), 4-(4 - pentylcyclohexyl)phenylboronic acid (44.1 mg, 0.161 mmol), palladium acetate (1.5 mg, 6.7 μmol), and 2 - dicyclohexylphosphino - 2’,4’,6’ - triisopropylbiphenyl (6.3 mg, 0.013 mmol) were suspended in THF (1.3 mL). To this suspension, an aqueous solution of 2.0 M potassium carbonate (0.201 mL, 0.402 mmol) was added, and the mixture was heated to reflux at 80 °C for 14 hours. After allowing to cool to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was dissolved in chloroform, activated carbon was added, and the mixture was stirred for 30 minutes, followed by filtration through Celite. The low - boiling components were distilled off under reduced pressure from the filtrate, and the obtained solid was purified by recrystallization (toluene) to obtain the target 4,6 - diphenyl - 2 - [4’ - {3 - (4’-(4 - pentylcyclohexyl)-1,1’ - biphenyl - 4 - yl)adamantan - 1 - yl}-biphenyl - 3 - yl]-1,3,5 - triazine as a white solid (yield 30.0 mg, yield 27%). 11H-NMR (400 MHz, CDCl3) δ (ppm): 9.01 (t, J = 1.7 Hz, 1H), 8.79 - 8.81 (m, 4H), 8.75 (dt, J = 7.8, 1.4 Hz, 1H), 7.83 - 7.85 (m, 1H), 7.73 (d, J = 8.5 Hz, 2H), 7.48 - 7.66 (m, 16H), 7.28 (s, 1H), 2.50 (tt, J = 12.0, 3.3 Hz, 1H), 2.39 (brs, 2H), 2.17 (s, 2H), 2.06 (dd, J = 8.9, 2.3 Hz, 8H), 1.95 (d, J = 3.2 Hz, 1H), 1.91 (brs, 2H), 1.86 (d, J = 2.0 Hz, 3H), 1.49 (dd, J = 12.5, 2.8 Hz, 2H), 1.20 - 1.37 (m, 10H), 1.01 - 1.11 (m, 2H), 0.90 (t, J = 7.0 Hz, 3H).

[0307] Synthesis Example - 9 (Compound - 1 - 6)

[0308] [Chemical Structure]

[0309] Under an argon atmosphere, 4,6-diphenyl-2-[4’-{3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-phenyl)adamantan-1-yl}-biphenyl-3-yl]-1,3,5-triazine (100 mg, 0.139 mmol), 2,4,6-triphenylbromobenzene (76.9 mg, 0.167 mmol), palladium acetate (1.8 mg, 7.0 μmol), and 2-dicyclohexylphosphino-2’,4’,6’-triisopropylbiphenyl (6.50 mg, 0.0139 mmol) were suspended in THF (1.5 mL). To this suspension was added an aqueous 2.0 M potassium carbonate solution (0.209 mL, 0.417 mmol), and the mixture was heated to reflux at 80 °C for 15 hours. After allowing to cool to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was dissolved in chloroform, activated carbon was added, and the mixture was stirred for 30 minutes, followed by filtration through celite. The low-boiling components were distilled off under reduced pressure from the filtrate, and the obtained solid was purified by recrystallization (toluene) to obtain the target 4,6-diphenyl-2-[4’-{3-(4’,6’-diphenyl-1,1’:2’:1’’-terphenyl-4-yl)-adamantan-1-yl}-biphenyl-3-yl]-1,3,5-triazine as a white solid (yield 24.0 mg, yield 19%). 1 1H-NMR (400 MHz, CDCl3) δ (ppm): 9.00 (t, J = 1.7 Hz, 1H), 8.71 - 8.79 (m, 4H), 8.75 (dt, J = 7.8, 1.4 Hz, 1H), 7.82 - 7.85 (m, 1H), 7.70 - 7.73 (m, 4H), 7.68 (s, 2H), 7.57 - 7.66 (m, 7H), 7.54 (d, J = 8.5 Hz, 2H), 7.46 (t, J = 7.4 Hz, 2H), 7.37 (tt, J = 6.6, 1.2 Hz, 1H), 7.12 - 7.18 (m, 10H), 7.03 (d, J = 8.5 Hz, 2H), 6.80 (d, J = 8.4 Hz, 2H), 2.31 (brs, 2H), 2.00 (brs, 6H), 1.86 (d, J = 2.4 Hz, 4H), 1.78 (brs, 2H).

[0310] Synthesis Example - 10 (Compound - 1 - 12)

[0311] [Chem.]

[0312] Under an argon atmosphere, 4,6-diphenyl-2-[4’-{3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl-phenyl)adamantan-1-yl}-biphenyl-3-yl]-1,3,5-triazine (67.6 mg, 0.0937 mmol), 3-chloro-9-phenyl-10-(1,1’-biphenyl-4-yl)phenanthrene (45.4 mg, 0.103 mmol), palladium acetate (1.0 mg, 4.7 μmol), and 2-dicyclohexylphosphino-2’,4’,6’-triisopropylbiphenyl (4.35 mg, 9.30 μmol) were suspended in THF (1.00 mL). To this suspension was added 5.0 M aqueous sodium hydroxide solution (0.056 mL, 0.28 mmol), and the mixture was heated to reflux at 80 °C for 15 hours. After allowing to cool to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was dissolved in chloroform, activated carbon was added, and the mixture was stirred for 30 minutes, followed by filtration through celite. The low-boiling components were distilled off under reduced pressure from the filtrate, and the obtained solid was purified by recrystallization (toluene) to give the desired 4,6-diphenyl-2-[4’-{3-(9-phenyl-10-(1,1’-biphenyl-4-yl)phenanthren-3-yl)-adamantan-1-yl}-biphenyl-3-yl]-1,3,5-triazine as a white solid (yield 33.0 mg, yield 35%). 11H-NMR (400 MHz, CDCl3) δ (ppm): 9.03 (d, J = 1.6 Hz, 1H), 9.02 (t, J = 1.7 Hz, 1H), 8.90 (d, J = 3.1 Hz, 1H), 8.79 - 8.81 (m, 4H), 8.76 (dt, J = 8.7, 1.6 Hz, 1H), 7.84 - 7.86 (m, 1H), 7.80 (d, J = 8.6 Hz, 2H), 7.67 - 7.79 (m, 5H), 7.57 - 7.65 (m, 14H), 7.44 (t, J = 7.5 Hz, 2H), 7.34 (tt, J = 6.7, 1.3 Hz, 1H), 7.25 (d, J = 1.2 Hz, 2H), 7.14 - 7.22 (m, 5H), 2.43 (brs, 2H), 2.22 (s, 2H), 2.10 (d, J = 2.3 Hz, 8H), 1.89 (brs, 2H).

[0313] Synthesis Example - 11 (Compound - 1 - 85)

[0314]

Chemical Structure

[0315] Under an argon atmosphere, 2,4-bis(1,1'-biphenyl-4-yl)-6-chloro-1,3,5-triazine (0.977 g, 2.33 mmol), 3-(4-biphenylyl)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-adamantane (1.37 g, 2.79 mmol), and tetrakis(triphenylphosphine)palladium (80.8 mg, 0.0699 mmol) were suspended in THF (25 mL). To this suspension, an aqueous solution of 2.0 M potassium carbonate (3.50 mL, 6.99 mmol) was added, and the mixture was heated under reflux at 80 °C for 17 hours. After allowing to cool to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was dissolved in chloroform, activated carbon was added, and the mixture was stirred for 30 minutes, followed by filtration through celite. The low-boiling components were distilled off under reduced pressure from the filtrate, and the obtained solid was purified by recrystallization (toluene) to obtain the target 4,6-bis(1,1'-biphenyl-4-yl)-2-[4-{3-(4-biphenylyl)adamantan-1-yl}-phenyl-1-yl]-1,3,5-triazine as a white solid (yield 1.23 g, yield 70%). 1 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.86 (d, J = 8.3 Hz, 4H), 7.85 (d, J = 8.6 Hz, 2H), 7.82 (d, J = 8.5 Hz, 4H), 7.71 - 7.74 (m, 4H), 7.64 (d, J = 8.6 Hz, 2H), 7.60 - 7.62 (m, 3H), 7.59 (t, J = 2.0 Hz, 1H), 7.51 (t, J = 7.6 Hz, 6H), 7.43 (q, J = 7.2 Hz, 4H), 7.33 (tt, J = 6.8, 1.3 Hz, 1H), 2.41 (brs, 2H), 2.19 (s, 2H), 2.07 (dd, J = 6.9, 2.7 Hz, 8H), 1.87 (brs, 2H).

[0316] Synthesis Example - 12 (Compound - 1 - 249)

[0317]

Chemical Structure

[0318] Under an argon atmosphere, 2-chloro-4,6-diphenylpyrimidine (27.2 mg, 0.102 mmol), 3-[4-(4-pyridinyl)phenyl]-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-adamantane (60.0 mg, 0.122 mmol), palladium acetate (2.3 mg, 5.1 μmol) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (4.90 mg, 0.0102 mmol) were suspended in THF (1.2 mL). To this suspension, an aqueous solution of 2.0 M potassium carbonate (0.153 mL, 0.306 mmol) was added, and the mixture was heated to reflux at 80 °C for 16 hours. After allowing to cool to room temperature, water was added to the reaction mixture, and the mixture was extracted with chloroform and dried over sodium sulfate. The solvent was distilled off, and the resulting solid was dissolved in chloroform. Activated carbon was added and the mixture was stirred for 30 minutes, followed by filtration through celite. The low-boiling components were distilled off under reduced pressure from the filtrate, and the resulting solid was purified by column chromatography (hexane / chloroform) to obtain the desired 4,6-diphenyl-2-[4′-{3-(4-(4-pyridinyl)phenyl)adamantan-1-yl}-biphenyl-4-yl]pyrimidine as a white solid (yield 33.0 mg, yield 35%). 1 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.67 (d, J = 8.7 Hz, 2H), 8.65 (d, J = 5.2 Hz, 2H), 8.28 - 8.31 (m, 4H), 8.01 (s, 1H), 7.64 (d, J = 8.5 Hz, 2H), 7.54 - 7.59 (m, 10H), 7.53 (dd, J = 4.5, 1.6 Hz, 2H), 2.40 (brs, 2H), 2.16 (s, 2H), 2.06 (dd, J = 11.0, 2.3 Hz, 8H), 1.86 (brs, 2H).

[0319] Synthesis Example - 13 (Compound - 1 - 29)

[0320]

Chemical Structure

[0321] Under an argon atmosphere, 4,6-diphenyl-2-[4’-{3-(4-trifluoromethanesulfonyloxyphenyl)adamantan-1-yl}-biphenyl-3-yl]-1,3,5-triazine (100 mg, 2.14 μmol), quinoline-4-boronic acid (34.9 mg, 202 μmol), palladium acetate (1.51 mg, 6.72 μmol), and 2-dicyclohexylphosphino-2’,4’,6’-triisopropylbiphenyl (6.29 mg, 13.4 μmol) were suspended in THF (1.0 mL). To this suspension was added 2.0 M aqueous potassium phosphate solution (0.202 mL, 0.403 μmol), and the mixture was heated to reflux at 80 °C for 18 hours. Then, a solution prepared by suspending palladium acetate (1.51 mg, 6.72 μmol) and 2-dicyclohexylphosphino-2’,4’,6’-triisopropylbiphenyl (6.29 mg, 13.4 μmol) in THF (1.0 mL) was added, and the mixture was heated to reflux again at 80 °C for 18 hours. After cooling to room temperature, the low-boiling components were distilled off under reduced pressure, water was added, and the mixture was extracted with chloroform and then dried over sodium sulfate and magnesium sulfate. The solid was filtered off, and the low-boiling components were distilled off under reduced pressure from the obtained filtrate. The obtained solid was purified by column chromatography (hexane / chloroform and toluene / ethyl acetate) to obtain the target 4,6-diphenyl-2-[4’-{3-(4-(4-quinolyl)phenyl)adamantan-1-yl}-biphenyl-3-yl]-1,3,5-triazine as a white solid (yield 52.6 mg, yield 54%). 1 1H-NMR (400 MHz, CDCl3) δ (ppm): 9.01 (t, J = 1.6 Hz, 1H), 8.94 (d, J = 4.4 Hz, 1H), 8.78 - 8.82 (m, 4H), 8.76 (dt, J = 7.9, 1.4 Hz, 1H) 8.18 (d, J = 8.2 Hz, 1H), 8.00 (d, J = 8.5 Hz, 1H), 7.85 (ddd, J = 7.5, 1.7, 1.1 Hz, 1H), 7.70 - 7.77 (m, 3H), 7.56 - 7.68 (m, 11H), 7.48 - 7.54 (m, 3H), 7.36 (d, J = 4,4 Hz, 1H), 2.43 (brs, 2H), 2.22 (s, 2H), 2.10 (d, J = 2.2 Hz, 8H), 1.89 (brs, 2H).

[0322] Synthesis Example - 14 (Compound - 1 - 38)

[0323] [Chemical Formula]

[0324] Under an argon atmosphere, 4,6 - diphenyl - 2 - [4’ - {3 - (4,4,5,5 - tetramethyl - 1,3,2 - dioxaborolan - 2 - yl - phenyl)adamantan - 1 - yl}-biphenyl - 3 - yl]-1,3,5 - triazine (21.1 mg, 75.5 μmol), 4 - chloro - 9 - phenyl - pyrido[2,3 - b]indole (60.0 mg, 83.1 μmol), palladium acetate (0.59 mg, 2.3 μmol), and 2 - dicyclohexylphosphino - 2’,4’,6’ - triisopropylbiphenyl (2.16 mg, 4.53 μmol) were suspended in THF (0.76 mL). To this suspension, an aqueous solution of 2.0 M potassium carbonate (0.113 mL, 0.227 mmol) was added, and the mixture was heated under reflux at 80 °C for 18 hours. After allowing to cool to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The low - boiling components were distilled off under reduced pressure from the filtrate, and the resulting solid was purified by column chromatography (hexane / ethyl acetate) to obtain the target 4,6 - diphenyl - 2 - [4’-(3 - (9 - phenylpyrido[2,3 - b]indol - 4 - yl)adamantan - 1 - yl)-biphenyl - 3 - yl]-1,3,5 - triazine as a white solid (yield 54.2 mg, yield 86%). 1H-NMR (400 MHz, CDCl3) δ (ppm): 9.02 (t, J = 1.6 Hz, 1H), 8.78 - 8.82 (m, 4H), 8.76 (dt, J = 7.9, 1.4 Hz, 1H), 8.49 (d, J = 5.0 Hz, 1H), 7.85 (ddd, J = 7.7, 1.8, 1.2 Hz, 1H), 7.74 - 7.81 (m, 3H), 7.69 - 7.73 (m, 2H), 7.56 - 7.68 (m, 17H), 7.38 - 7.52 (m, 3H), 7.15 (d, J = 5.0 Hz, 1H), 7.13 (ddd, J = 8.1, 6.9, 1.4 Hz, 1H), 2.46 (brs, 2H), 2.27 (s, 2H), 2.07 - 2.20 (m, 8H), 1.91 (brs, 2H).

[0325] Synthesis Example - 15 (Compound - 1 - 107)

[0326]

Chemical Structure

[0327] Under an argon atmosphere, 2-(4-bromophenyl)-4,6-di(1-naphthalenyl)-1,3,5-triazine (49.8 mg, 0.102 mmol), 3-[4-(4-pyridinyl)phenyl]-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-adamantane (60.0 mg, 0.122 mmol), palladium acetate (1.1 mg, 5.1 μmol) and 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (4.9 mg, 10 μmol) were suspended in THF (1.2 mL). To this suspension, an aqueous solution of 2.0 M potassium carbonate (0.153 mL, 0.306 mmol) was added, and the mixture was heated to reflux at 80 °C for 11 hours. After allowing to cool to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was dissolved in chloroform, activated carbon was added, and the mixture was stirred at room temperature for 30 minutes, followed by filtration through celite. The low-boiling components were distilled off under reduced pressure from the filtrate, and the obtained solid was purified by recrystallization (toluene) to obtain the target 4,6-di(1-naphthalenyl)-2-[4′-(3-(4-(4-pyridinyl)phenyl)adamantan-1-yl)-biphenyl-4-yl]-1,3,5-triazine as a white solid (yield 32.0 mg, yield 34%). 1 1H-NMR (CDCl3) δ (ppm): 9.22 (d, J = 8.6 Hz, 2H), 8.85 (d, J = 8.6 Hz, 2H), 8.63 - 8.66 (m, 2H), 8.58 (dd, J = 7.2, 1.2 Hz, 2H), 8.10 (d, J = 8.2 Hz, 2H), 7.99 (d, J = 8.0 Hz, 2H), 7.83 (d, J = 8.6 Hz, 2H), 7.46 - 7.72 (m, 16H), 2.40 (brs, 2H), 2.11 - 2.14 (m, 2H), 2.03 - 2.05 (m, 8H), 1.85 (brs, 2H).

[0328] Synthesis Example - 16 (Compound - 1 - 109)

[0329]

Chemical Structure

[0330] Under an argon atmosphere, 2-(4’-bromo-[1,1-biphenyl]-4-yl)-4,6-bis[4-(1,1-dimethylethyl)phenyl]-1,3,5-triazine (58.8 mg, 0.102 mmol), 3-[4-(4-pyridinyl)phenyl]-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenyl)-adamantane (60.0 mg, 0.122 mmol), palladium acetate (1.1 mg, 5.1 μmol) and 2-dicyclohexylphosphino-2’,4’,6’-triisopropylbiphenyl (4.9 mg, 10 μmol) were suspended in THF (1.2 mL). To this suspension, an aqueous solution of 2.0 M potassium carbonate (0.153 mL, 0.306 mmol) was added and the mixture was heated to reflux at 80 °C for 11 h. After allowing to cool to room temperature, water and methanol were added to the reaction mixture and the precipitated solid was collected by filtration. The obtained solid was dissolved in chloroform, activated carbon was added and the mixture was stirred at room temperature for 30 min, followed by filtration through celite. The low-boiling components were distilled off under reduced pressure from the filtrate, and the obtained solid was purified by recrystallization (toluene) to obtain the target 4,6-bis[4-(1,1-dimethylethyl)phenyl]-2-[4’’-(3-(4-(4-pyridinyl)phenyl)adamantan-1-yl)-1,1’:4’,1’’-terphenyl-4-yl]-1,3,5-triazine as a white solid (yield 42.0 mg, yield 40%). 1 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.86 (d, J = 8.5 Hz, 2H), 8.71 (d, J = 8.6 Hz, 4H), 8.65 (dd, J = 4.6, 1.6 Hz, 2H), 7.85 (d, J = 8.4 Hz, 2H), 7.80 (d, J = 8.4 Hz, 2H), 7.73 (d, J = 8.4 Hz, 2H), 7.60 - 7.67 (m, 8H), 7.51 - 7.56 (m, 6H), 2.40 (brs, 2H), 2.15 (s, 2H), 2.05 (dd, J = 7.4, 2.5 Hz, 8H). 1.86 (brs, 2H), 1.42 (s, 18H).

[0331] Synthesis Example - 18 (Compound - 1 - 114)

[0332]

Chemical Structure

[0333] Under an argon atmosphere, 2,4-diphenyl-6-[4'-(2-pyridinyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,1'-biphenyl-3-yl]-1,3,5-triazine (50 mg, 0.0850 mmol), 3-[4-(4-pyridinyl)phenyl]-1-(4-trifluoromethanesulfonyloxyphenyl)-phenyl)-adamantane (51 mg, 0.0985 mmol), palladium acetate (1.0 mg, 4.25 μmol), and 2-dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (4.2 mg, 8.5 μmol) were suspended in THF (1.0 mL). To this suspension, an aqueous solution of 2.0 M potassium carbonate (0.140 mL, 0.280 mmol) was added, and the mixture was heated to reflux at 80 °C for 15 h. After allowing to cool to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was dissolved in chloroform, activated carbon was added, and the mixture was stirred at room temperature for 30 min, followed by filtration through celite. The low-boiling components were distilled off under reduced pressure from the filtrate, and the obtained solid was purified by recrystallization (toluene) to obtain the target 2,4-diphenyl-6-[4-(2-pyridinyl)-4''-{3-(4-(4-pyridinyl)phenyl)-adamantan-1-yl}-1,1':3',1''-terphenyl-3-yl]-1,3,5-triazine as a white solid (yield 24.0 mg, yield 33%). 1 1H-NMR (400 MHz, CDCl3) δ (ppm): 9.01 (tt, J = 9.8, 1.5 Hz, 2H), 8.80 - 8.83 (m, 4H), 8.74 - 8.76 (m, 1H), 8.65 (dd, J = 4.5, 1.6 Hz, 2H), 8.19 (d, J = 8.4 Hz, 2H), 8.09 (t, J = 1.7 Hz, 1H), 7.92 (d, J = 8.9 Hz, 2H), 7.79 - 7.85 (m, 4H), 7.55 - 7.66 (m, 12H), 7.52 (dd, J = 4.6, 1.6 Hz, 2H), 7.27 - 7.29 (m, 1H), 2.41 (brs, 2H), 2.18 (s, 2H), 2.07 (dd, J = 15.5, 2.7 Hz, 8H), 1.87 (brs, 2H).

[0334] Synthesis Example - 19 (Compound - 1 - 117)

[0335]

Chemical Structure

[0336] Under an argon atmosphere, 4,6 - diphenyl - 2 - (9 - bromo - 10 - phenylphenanthren - 2 - yl) - 1,3,5 - triazine (57.6 mg, 0.102 mmol), 3 - [4 - (4 - pyridinyl)phenyl] - 1 - (4,4,5,5 - tetramethyl - 1,3,2 - dioxaborolan - 2 - yl)phenyl - adamantane (60 mg, 0.122 mmol), palladium(II) acetate (1.1 mg, 5.09 μmol) and 2 - dicyclohexylphosphino - 2′,4′,6′ - triisopropylbiphenyl (4.9 mg, 10 μmol) were suspended in THF (1.2 mL). To this suspension, 2.0 M aqueous potassium carbonate solution (0.153 mL, 0.306 mmol) was added and the mixture was heated to reflux at 80 °C for 11 h. After allowing to cool to room temperature, water and methanol were added to the reaction mixture and the precipitated solid was collected by filtration. The obtained solid was dissolved in chloroform, activated carbon was added and the mixture was stirred at room temperature for 30 min, followed by filtration through celite. The low - boiling components were distilled off under reduced pressure from the filtrate, and the obtained solid was purified by recrystallization (toluene) to give the desired 4,6 - diphenyl - 2 - [9 - {4 - (3 - (4 - (4 - pyridinyl)phenyl)adamantan - 1 - yl)phenyl - 10 - phenylphenanthren - 2 - yl] - 1,3,5 - triazine as a white solid (yield 77.0 mg, yield 75%). 1 1H - NMR (400 MHz, CDCl3) δ (ppm): 8.64 (dd, J = 4.6, 1.6 Hz, 2H), 7.63 (d, J = 8.6 Hz, 2H), 7.52 - 7.58 (m, 4H), 7.51 (dd, J = 4.7, 1.6 Hz, 2H), 7.47 (d, J = 8.6 Hz, 2H), 2.37 (brs, 2H), 2.12 (s, 2H), 2.02 (brs, 8H), 1.84 (brs, 2H).

[0337] Synthesis Example - 20 (Compound - 1 - 248)

[0338] [Chemical Formula]

[0339] Under an argon atmosphere, 4’-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-2,2’:6’2’’-terpyridine (100 mg, 0.230 mmol), 3-[4-(4-pyridinyl)phenyl]-1-(4-trifluoromethanesulfonyloxyphenyl)-adamantane (142 mg, 0.276 mmol), palladium acetate (2.6 mg, 0.012 mmol) and 2-dicyclohexylphosphino-2’,4’,6’-triisopropylbiphenyl (10.8 mg, 0.0230 mmol) were suspended in THF (2.3 mL). To this suspension, an aqueous solution of 2.0 M potassium carbonate (0.345 mL, 0.690 mmol) was added and the mixture was heated to reflux at 80 °C for 14 hours. After allowing to cool to room temperature, water was added to the reaction mixture, and the mixture was extracted with chloroform and dried over sodium sulfate. The solvent was distilled off, and the resulting solid was dissolved in chloroform. Activated carbon was added and the mixture was stirred for 30 minutes, followed by filtration through celite. The low-boiling components were distilled off under reduced pressure from the filtrate, and the resulting solid was purified by column chromatography (hexane / chloroform) to obtain the desired 4’-[4’-{3-(4-(4-pyridinyl)phenyl)adamantan-1-yl}-biphenyl-3-yl]-2,2’:6’2’’-terpyridine as a white solid (yield 78.0 mg, yield 50%). 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.79 (s, 2H), 8.72 - 8.74 (m, 2H), 8.69 (dt, J = 8.0, 1.0 Hz, 2H), 8.64 (dd, J = 4.5, 1.6 Hz, 2H), 8.09 (t, J = 1.7 Hz, 1H), 7.85 - 7.91 (m, 3H), 7.66 - 7.69 (m, 3H), 7.63 (d, J = 8.6 Hz, 2H), 7.51 - 7.59 (m, 7H), 7.37 (dd, J = 4.8, 1.2 Hz, 1H), 7.35 (dd, J = 4.7, 1.2 Hz, 1H), 2.39 (brs, 2H), 2.14 (s, 2H), 2.04 (dd, J = 8.5, 2.5 Hz, 8H), 1.85 (brs, 2H).

[0340] Synthesis Example - 21 (Compound - 1 - 250)

[0341]

Chemical Structure

[0342] Under an argon atmosphere, 4,6 - diphenyl - 2 - [4’ - {3 - (4,4,5,5 - tetramethyl - 1,3,2 - dioxaborolan - 2 - yl - phenyl)adamantan - 1 - yl}-biphenyl - 3 - yl]-1,3,5 - triazine (50.0 mg, 69.3 μmol), 9 - chloroacridine (22 mg, 104 μmol) and tetrakis triphenylphosphine palladium (4.0 mg, 3.46 μmol) were suspended in 1,4 - dioxane (0.70 mL). To this suspension, 2.0 M aqueous potassium carbonate solution (104 μL, 208 μmol) was added, and the mixture was heated under reflux at 110 °C for 10 hours. After cooling to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was dissolved in chloroform, activated carbon was added, and the mixture was stirred at 60 °C for 30 minutes, followed by filtration through celite. The low - boiling components were distilled off under reduced pressure from the filtrate, and the obtained solid was purified by column chromatography (hexane / ethyl acetate) to obtain the target 4,6 - diphenyl - 2 - [4’ - {3 - (4 - acridinyl)phenyl)adamantan - 1 - yl}biphenyl - 3 - yl]-1,3,5 - triazine as a white solid (yield 27.2 mg, yield 51%). 1 1H-NMR (400 MHz, CDCl3) δ (ppm): 9.02 (t, J = 1.6 Hz, 1H), 8.78 - 8.83 (m, 4H), 8.76 (dt, J = 7.9, 1.4 Hz, 1H), 8.25 - 8.30 (m, 2H), 7.85 (ddd, J = 7.7, 1.8, 1.2 Hz, 1H), 7.74 - 7.80 (m, 6H), 7.56 - 7.69 (m, 11H), 7.41 - 7.46 (m, 4H), 2.47 (brs, 2H), 2.27 (s, 2H), 2.17 (brs, 4H), 2.13 (brs, 4H), 1.92 (brs, 2H).

[0343] Synthesis Example - 23 (Compound - 1 - 122)

[0344] [Chemical Structure]

[0345] Under an argon atmosphere, 2,4 - diphenyl - 6 - [4 - (4,4,5,5 - tetramethyl - 1,3,2 - dioxaborolan - 2 - yl)phenyl] - 1,3,5 - triazine (1.16 g, 2.67 mmol), 3,5 - (4 - biphenylyl) - 1 - (4 - trifluoromethanesulfonyloxyphenyl)adamantane (1.48 g, 2.67 mmol), and tetrakis(triphenylphosphine)palladium (128 mg, 0.111 mmol) were suspended in THF (23 mL). To this suspension, an aqueous 2.0 M potassium phosphate solution (3.3 mL, 6.6 mmol) was added, and the mixture was heated under reflux at 80 °C for 24 hours. After allowing to cool to room temperature, water and methanol were added to the reaction mixture, and the precipitated solid was collected by filtration. The obtained solid was dissolved in chloroform, activated carbon was added, and the mixture was stirred at 70 °C for 30 minutes, then allowed to cool and filtered through celite. The low - boiling components were distilled off under reduced pressure from the filtrate, and the obtained solid was purified by column chromatography (hexane / chloroform) to obtain the target 4,6 - diphenyl - 2 - [1’ - {3,5 - bis(4 - biphenylyl)adamantan - 1 - yl}biphenyl - 4 - yl] - 1,3,5 - triazine as a white solid (yield 947 mg, yield 52%). 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.85 (t, J = 8.5 Hz, 2H), 8.80 (dd, J = 7.7, 1.5 Hz, 4H), 7.82 (dt, J = 8.6, 2.0 Hz, 2H), 7.72 (d, J = 7.7 Hz, 2H), 7.58 - 7.63 (m, 15H), 7.57 (brs, 3H), 7.55 (brs, 2H), 7.44 (t, J = 7.6 Hz, 4H), 7.34 (tt, J = 7.3, 1.3 Hz, 2H), 2.63 (brs, 1H), 2.24 (s, 6H), 2.11 (dd, J = 8.2, 2.5 Hz, 6H).

[0346] Reference Example - 1

[0347] [Chemical formula]

[0348] Under an argon atmosphere, (adamantane-1,3-diyl)bis(4,1-phenylene)bis(trifluoromethanesulfonic acid) (4.38 g, 7.50 mmol), 5,5-dimethyl-2-phenyl-1,3,2-dioxaborolane (1.28 g, 6.75 mmol), and tetrakis(triphenylphosphine)palladium (260 mg, 0.225 mmol) were suspended in THF (75 mL). To this suspension, 2.0 M aqueous potassium carbonate solution (11.3 mL, 22.5 mmol) was added, and the mixture was heated under reflux at 80 °C for 24 hours. After allowing to cool to room temperature, water was added to the reaction mixture, and the mixture was extracted with chloroform and dried over sodium sulfate and magnesium sulfate. After filtering off the solid, the low-boiling components were distilled off under reduced pressure from the filtrate, and the resulting solid was purified by column chromatography (hexane / chloroform) to obtain the target 4-(3-([1,1'-biphenyl]-4-yl)adamantan-1-yl)phenyl trifluoromethanesulfonic acid as a white solid (yield 1.08 g, yield 31%). 1H-NMR (400 MHz, CDCl3) δ (ppm): 7.54 - 7.61 (m, 4H), 7.40 - 7.50 (m, 6H), 7.33 (tt, J = 7.3, 1.9 Hz, 1H), 7.19 - 7.24 (m, 2H), 2.33 - 2.40 (brm, 2H), 1.94 - 2.08 (m, 10H), 1.82 (d, J = 2.8 Hz, 2H).

[0349] Reference Example - 2

[0350]

Chem.

[0351] It was obtained by the same method as in Reference Example - 1 except that 5,5 - dimethyl - 2 - phenyl - 1,3,2 - dioxaborolane was changed to 2 - phenyl - 5 - (4,4,5,5 - tetramethyl - 1,3,2 - dioxaborolan - 2 - yl) pyridine (yield 860 mg, yield 42%). 1 H-NMR (400 MHz, CDCl3) δ (ppm): 8.94 (d, J = 2.0 Hz, 1H), 8.04 (d, J = 7.4 Hz, 2H), 7.95 (dd, J = 8.2, 2.2 Hz, 1H), 7.80 (d, J = 8.1 Hz, 1H), 7.62 (d, J = 8.4 Hz, 2H), 7.39 - 7.55 (m, 7H), 7.22 (d, J = 8.9 Hz, 2H), 2.39 (brs, 2H), 2.06 (brs, 2H), 2.00 (dd, J = 8.2, 2.2 Hz, 1H), 1.95 - 2.04 (m, 8H), 1.83 (brs, 2H).

[0352] Reference Example - 3

[0353]

Chem.

[0354] The target product was obtained using the same method as in Reference Example - 1 except that 5,5 - dimethyl - 2 - phenyl - 1,3,2 - dioxaborolane was changed to 4 - cyanophenylboronic acid (yield 367 g, yield 40%). 1 1H-NMR (400 MHz, CDCl3) δ (ppm): 7.65 - 7.74 (m, 4H), 7.22 (dt, J = 8.5, 2.0 Hz, 2H), 7.48 - 7.52 (m, 2H), 7.47 (dt, J = 9.0, 2.1 Hz, 2H), 7.22 (dt, J = 8.9, 2.1 Hz, 2H), 2.37 (brs, 2H), 2.04 (brs, 2H), 1.94 - 2.03 (m, 8H), 1.83 (brs, 2H), 1.82 (brs, 2H).

[0355] Reference Example - 4

[0356]

Chem.

[0357] The target product was obtained in the same manner as in Reference Example - 1, except that 5,5 - dimethyl - 2 - phenyl - 1,3,2 - dioxaborolane was changed to 4 - pyridylboronic acid (yield 1.71 g, yield 40%). 1 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.64 (dd, J = 4.5, 1.6 Hz, 2H), 7.26 (d, J = 8.4 Hz, 2H), 7.49 - 7.52 (m, 4H), 7.47 (d, J = 8.9 Hz, 2H), 7.22 (d, J = 8.9 Hz, 2H), 2.37 (brs, 2H), 2.05 (s, 2H), 1.99 (dd, J = 15.1, 2.5 Hz, 8H), 1.82 (brs, 2H).

[0358] Reference Example - 5

[0359]

Chem.

[0360] The target product was obtained in the same manner as in Reference Example-1, except that ((1s,3s,5r,7r)-adamantane-1,3-diyl)bis(4,1-phenylene)bis(trifluoromethanesulfonic acid) was changed to ((1s,3s,5s)-adamantane-1,3,5-triyl)tris(benzene-4,1-diyl)tris(trifluoromethanesulfonic acid), and 5,5-dimethyl-2-phenyl-1,3,2-dioxaborolane was changed to phenylboronic acid (yield 1.48 g, yield 49%). 1 1H-NMR (400 MHz, CDCl3) δ (ppm): 7.57 - 7.63 (m, 5H), 7.50 - 7.55 (m, 4H), 7.44 (t, J = 7.0 Hz, 4H), 7.34 (t, J = 7.3 Hz, 2H), 7.25 (d, J = 8.3 Hz, 4H), 7.18 (d, J = 7.3 Hz, 3H), 2.61 (brs, 1H), 2.00 - 2.22 (m, 12H).

[0361] Device Example-1 (see Figure 1) (Preparation of Substrate 1 and Anode 2) As the substrate 1 provided with the anode 2 on its surface, a glass substrate with an indium tin oxide (ITO) transparent electrode (ITO film width: 2 mm, film thickness: 110 nm) patterned in a stripe shape was prepared. Then, this substrate was washed with isopropyl alcohol and then surface-treated by ozone ultraviolet cleaning.

[0362] (Preparation for Vacuum Deposition) On the substrate subjected to surface treatment after cleaning, each layer was formed by vacuum deposition in a vacuum deposition method, and each layer was laminated. First, the glass substrate was introduced into the vacuum deposition chamber, and the pressure was reduced to 1.0×10−4 Pa. Then, each layer was fabricated according to the film formation conditions of each layer in the following order. Each organic material was formed by a resistance heating method.

[0363] (Fabrication of Hole Injection Layer 3) The sublimation-purified N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluorene-2-amine and 1,2,3-tris[(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane were formed into a film with a thickness of 10 nm at a ratio of 99:1 (mass ratio) to fabricate the hole injection layer 3. The film formation rate was 0.1 nm / second.

[0364] (Fabrication of the first hole transport layer 41; Fabrication of the hole transport layer 4) The sublimation-purified N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluorene-2-amine was formed into a film with a thickness of 85 nm at a rate of 0.2 nm / second to fabricate the first hole transport layer 41.

[0365] (Fabrication of the second hole transport layer 42; Fabrication of the hole transport layer 4) The sublimation-purified N-phenyl-N-(9,9-diphenylfluorene-2-yl)-N-(1,1'-biphenyl-4-yl)amine was formed into a film with a thickness of 5 nm at a rate of 0.15 nm / second to fabricate the second hole transport layer 42.

[0366] (Fabrication of the light-emitting layer 5) The sublimation-purified 3-(10-phenyl-9-anthryl)-dibenzofuran and 2,7-bis[N,N-di-(4-tert-butylphenyl)]amino-bisbenzofurano-9,9'-spirofluorene were formed into a film with a thickness of 20 nm at a ratio of 95:5 (mass ratio) to fabricate the light-emitting layer 5. The film formation rate was 0.1 nm / second.

[0367] (Fabrication of the hole blocking layer (electron transport auxiliary layer) 9) 4,6-diphenyl-2-[4'-(3-(4-biphenylyl)adamantan-1-yl)-biphenyl-3-yl]-1,3,5-triazine (Compound 1-1) synthesized in Synthesis Example 1 was formed into a film with a thickness of 6 nm at a rate of 0.05 nm / second to fabricate the hole blocking layer (electron transport auxiliary layer) 9.

[0368] (Fabrication of the electron transport layer 6) The sublimated 4,6-diphenyl-2-(4-{4-[4'-cyano-(1,1'-biphenyl)-4-yl]naphthalen-1-yl}phenyl)-1,3,5-triazine (ETL-1) and lithium 8-hydroxyquinolinate (hereinafter, Liq) were formed into a film with a thickness of 25 nm at a ratio of 50:50 (mass ratio) to fabricate an electron transport layer 6. The film formation rate was 0.15 nm / second.

[0369] (Fabrication of electron injection layer 7) Liq was formed into a film with a thickness of 1 nm at a rate of 0.02 nm / second to fabricate an electron injection layer 7.

[0370] (Fabrication of cathode 8) Finally, a metal mask was arranged so as to be orthogonal to the ITO stripe (anode 2) on the substrate 1, and the cathode 8 was formed into a film. The cathode was formed into a film with a thickness of 80 nm and 20 nm in this order with silver / magnesium (mass ratio 1 / 10) and silver, respectively, to form a two-layer structure. The film formation rate of silver / magnesium was 0.5 nm / second, and the film formation rate of silver was 0.2 nm / second.

[0371] As described above, a light-emitting area of 4 mm as shown in FIG. 2 2 An organic light-emitting device 100 was fabricated. The film thickness of each was measured with a stylus type film thickness gauge (DEKTAK, manufactured by Bruker).

[0372] Furthermore, the organic light-emitting device 100 fabricated in this manner was sealed in a nitrogen atmosphere glove box with an oxygen and moisture concentration of 1 ppm or less. The sealing was performed using a glass sealing cap and a film-forming substrate (element) with bisphenol F type epoxy resin (manufactured by Nagase ChemteX).

[0373] Device Example - 2 An organic light-emitting device was fabricated in the same manner as in Device Example - 1, except that the compound 1-69 synthesized in Synthesis Example - 22 was used instead of the compound 1-1 used as the material for the hole blocking layer 9 in Device Example - 1.

[0374] Device Example - 3 Instead of Compound 1-1, 2-[3’-(9,9-dimethyl-9H-fluoren-2-yl)[1,1’-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine (ETL-2) described in JP-T-2018-507174 was used, and an organic light-emitting device was fabricated in the same manner as in Device Example-1, except that Compound 1-91 synthesized in Synthesis Example-11 was used instead of ETL-1.

[0375] Device Example-4 An organic light-emitting device was fabricated in the same manner as in Device Example-1, except that ETL-2 was used instead of Compound 1-1 and Compound 1-24 synthesized in Synthesis Example-2 was used instead of ETL-1.

[0376] Device Example-5 An organic light-emitting device was fabricated in the same manner as in Device Example-1, except that ETL-2 was used instead of Compound 1-1 and Compound 1-100 synthesized in Synthesis Example-3 was used instead of ETL-1.

[0377] Device Reference Example-1 An organic light-emitting device was fabricated in the same manner as in Device Example-1, except that the following Compound XX was used instead of Compound 1-1.

[0378]

Chemical Formula

[0379] Device Reference Example-2 An organic light-emitting device was fabricated in the same manner as in Device Example-1, except that ETL-2 was used instead of Compound 1-1 and Compound X described in Patent Document 3 was used instead of ETL-1. <Measurement Method of Current Efficiency and Device Lifetime>

[0380] A direct current was applied to the organic electroluminescent device fabricated as described above, and the light-emitting characteristics were evaluated using a luminance meter (product name: BM-9, manufactured by Topcon Technohouse Co., Ltd.). As the light-emitting characteristics, a current density of 10 mA / cm 2The current efficiency (cd / A) when current was passed through was measured, and the element lifetime (h) during continuous lighting was measured. Note that the element lifetime (h) in Table 3 is the luminance decay time during continuous lighting when the fabricated element was driven at an initial luminance of 1000 cd / m 2 and the time required until the luminance (cd / m 2 ) decreased by 5% was measured. Note that the current efficiency and the element lifetime are relative values with the results in Element Reference Example 1 and Element Reference Example 2 as the reference value (100). The obtained measurement results are shown in Tables 1 and 2.

[0381]

Table 1

[0382]

Table 2

[0383] The adamantane compound according to one aspect of the present invention can provide an organic light-emitting element excellent in element lifetime characteristics and high-efficiency characteristics by using the compound.

Explanation of Signs

[0384] 100 Organic light-emitting element 1 Substrate 2 Anode 3 Hole injection layer 4 Hole transport layer 5 Light-emitting layer 6 Electron transport layer 7 Electron injection layer 8 Cathode

Claims

1. An adamantane compound represented by formula (1a). 【Chemical 1】 (In formula (1a), A is, independently of each other, Composed of only an azine ring; or composed of only an azine ring and a six-membered ring which may be linked and / or fused to the azine ring; an unsubstituted heteroaryl group having 2 to 30 carbon atoms, The unsubstituted heteroaryl group is An alkyl group having 1 to 30 carbon atoms, A cyano group, A fluorine atom, An alkoxy group having 1 to 10 carbon atoms, An aryl group having 6 to 30 carbon atoms composed of only an aromatic ring which may be linked and / or fused, and A substituted heteroaryl group having 2 to 30 carbon atoms substituted with one or more groups selected from the group consisting of an alkyl group having 1 to 30 carbon atoms, a cyano group, a fluorine atom, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms composed of only an aromatic ring which may be linked and / or fused, and a heteroaryl group having 2 to 30 carbon atoms composed of only an aromatic ring which may be linked and / or fused, or A group represented by formula (3). 【Chemical 2】 (In formula (3), X １ and X ２ are each independently A nitrogen atom, or R １ which may be replaced by a carbon atom, X ２ One of them is a carbon atom bonded to L, X ２ At least one of them is a nitrogen atom. R １ is each independently an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms. Two adjacent Rs １ may be bonded to each other to form a condensed ring. Y is R ２ a nitrogen atom to which it is attached, An oxygen atom, A sulfur atom, or One or more R ２ which may be replaced by a carbon atom, R ２ is each independently an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, or a heteroaryl group having 2 to 30 carbon atoms. Two adjacent Rs ２ may be bonded to each other to form a condensed ring. R １ and R ２ are each independently An alkyl group having 1 to 30 carbon atoms, A cyano group, A fluorine atom, An alkoxy group having 1 to 10 carbon atoms, An aryl group having 6 to 30 carbon atoms composed of only an aromatic ring which may be linked and / or fused, and May be substituted with one or more groups selected from the group consisting of an alkyl group having 1 to 30 carbon atoms, a cyano group, a fluorine atom, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms composed of only an aromatic ring which may be linked and / or fused, and a heteroaryl group having 2 to 30 carbon atoms composed of only an aromatic ring which may be linked and / or fused. L is, independently of each other, a 1,2-phenylene group, a 1,3-phenylene group, a 1,4-phenylene group, a 2,9-phenanthrylene group, or a heteroarylene group having 2 to 30 carbon atoms. Z is, independently of each other, a group represented by formula (4). 【Chemical Formula 3】 (In formula (4), m １ each independently represents an integer from 0 to 4. m ２ each independently represents an integer from 1 to 4. L １ are each independently An arylene group having 6 to 30 carbon atoms, or A heteroarylene group having 2 to 30 carbon atoms containing an azine ring, Ar １ is a phenyl group. p represents 1. L, and L １ are each independently An alkyl group having 1 to 30 carbon atoms, A cyano group, A fluorine atom, An alkoxy group having 1 to 10 carbon atoms, An aryl group having 6 to 30 carbon atoms composed of only an aromatic ring which may be linked and / or fused, and May be substituted with one or more groups selected from the group consisting of an alkyl group having 1 to 30 carbon atoms, a cyano group, a fluorine atom, an alkoxy group having 1 to 10 carbon atoms, an aryl group having 6 to 30 carbon atoms composed of only an aromatic ring which may be linked and / or fused, and a heteroaryl group having 2 to 30 carbon atoms composed of only an aromatic ring which may be linked and / or fused. However, the compound represented by formula (1a) has At least one group represented by formula (T) in the molecule, and Does not have two or more triazine rings. [Chemical Formula 4] (In formula (T), X ３ is a nitrogen atom. R ４ is each independently an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 2 to 20 carbon atoms. R ４ is An alkyl group having 1 to 10 carbon atoms, A cyano group, A fluorine atom, An alkoxy group having 1 to 10 carbon atoms An aryl group having 6 to 20 carbon atoms composed of only an aromatic ring which may be linked and / or fused, and It may be substituted with one or more groups selected from the group consisting of heteroaryl groups having 2 to 20 carbon atoms composed only of aromatic rings which may be linked and / or condensed. However, in the compound represented by the general formula (1a), the following group (E) has 【Chemical Formula 5】 a group represented by -Z and has a different composition formula.)

2. The adamantane compound according to claim 1, wherein each of A is independently an unsubstituted heteroaryl group having 2 to 30 carbon atoms or a substituted heteroaryl group having 2 to 30 carbon atoms.

3. The aforementioned L １ is each independently a phenylene group, naphthylene group, fluorenylene group, anthrylene group, phenanthrylene group, benzofluorenylene group, pyrenylene group, perylenylene group, fluoranthenylene group, triphenylenylene group, chrysenylene group, acenaphthylene group, dibenzochrysenylene, benzofuranylene group, benzothienylene group, dibenzofuranylene group, dibenzothienylene group, xanthenylenylene group, or thioxanthenylenylene group, which may each independently have a substituent; Said L and L １ The adamantane compound according to claim 1 or 2, wherein the substituent(s) possessed by １ is / are one or more substituents selected from the group consisting of a phenyl group, a tolyl group, a pyridyl group, a methylpyridyl group, a dimethylpyridyl group, a fluorine atom, a cyano group, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, and a ring formed by bonding these substituents.

4. The above L １ The adamantane compound according to any one of claims 1 to 3, wherein each of them is independently a phenylene group, a naphthylene group, a fluorenylene group, an anthrylene group, or a phenanthrylene group.

5. A first electrode, a second electrode provided opposite to the first electrode, and an organic light-emitting device including a plurality of organic layers provided between the first electrode and the second electrode, wherein at least one of the plurality of organic layers contains the adamantane compound according to any one of claims 1 to 4.

6. An electron transport material containing the adamantane compound according to any one of claims 1 to 4.

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