Amine compound, material for metal patterning, thin film for metal patterning, organic electroluminescence device, electronic apparatus, and metal pattern forming method

Abstract

To provide an amine compound, a material for metal patterning that is highly capable of inhibiting metal thin film formation onto the film surface, as well as a thin film for metal patterning, an organic electroluminescence device, a metal pattern forming method and an electronic apparatus, employing the same.SOLUTION: The present invention provides amine compounds represented by formula (1) or the like.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present disclosure relates to an amine compound, a material for metal patterning, a thin film for metal patterning, an organic electroluminescence element, an electronic device, and a method for forming a metal pattern. [Background technology]

[0002] In recent years, organic electronic devices such as organic electroluminescence (EL) elements, organic thin-film solar cells, organic transistors, and organic sensors have been widely developed. In organic electronic devices, metal thin films are used as electrodes, but it is necessary to pattern the metal thin films into desired shapes.

[0003] A known method for patterning a metal electrode is to form a patterned film of a metal patterning material with reduced metal adhesion as an underlayer, and then evaporate a metal from the underlayer. In this method, a metal film is selectively formed in the area where the metal patterning material is not formed, so that a metal electrode patterned in a desired shape can be formed. Patent Document 1 discloses a technique for patterning magnesium metal using an anthracene derivative as a material for metal patterning. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] International Publication No. 2020 / 225778 Summary of the Invention [Problem to be solved by the invention]

[0005] However, in the method of Patent Document 1, it is difficult to form a pattern while highly suppressing the deposition of the metal in places other than the desired places. Furthermore, it is difficult to pattern metals other than magnesium with the compound described in Patent Document 1.

[0006] Thus, one aspect of the present disclosure is directed to providing a novel amine compound, a material for metal patterning capable of highly inhibiting the formation of various metal thin films on a film surface, a thin film for metal patterning using the same, an organic electroluminescence element, a method for forming a metal pattern, and an electronic device. [Means for solving the problem]

[0007] The amine compound according to one embodiment of the present invention is represented by the formulas (1) to (3):

[0008] [ka]

[0009] [ka]

[0010] [ka]

[0011] In formulas (1) to (3), Ar 101 , Ar 201 , Ar 301 are each independently any one of the following formulas (4-1) to (4-7), and * represents a bond:

[0012] [ka]

[0013] In formulas (4-1) to (4-7), R 401 ~R 409 are each independently Hydrogen atoms, Deuterium atom, fluorine atom, Bromine atom, Chlorine atom, a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a fluorine atom; a linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms which may be substituted with a fluorine atom; an optionally substituted monocyclic, linked or fused ring cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms; an optionally substituted monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 25 carbon atoms; an optionally substituted monocyclic, linked or fused heteroaromatic group having 3 to 25 carbon atoms, or Represented by the following formula (5):

[0014] [ka]

[0015] In formula (5), L 501 and L 502 are each independently a linear or branched divalent aliphatic hydrocarbon group having 1 to 4 carbon atoms; Oxygen atom, Sulfur atom, or Represents a single bond; n represents an integer of 3 to 11. In formula (4-1), R 401 and R 402 At least one of the following is expressed by Equation (5): In formulas (4-2) to (4-4), R 403 ~R 405 At least one of the following is expressed by Equation (5): In formulas (4-5) to (4-7), R 406 ~R 409 At least one of the following is expressed by Equation (5): In formulas (1) to (3), R 101 , R 102 , R 201 ~R 203 , R 301 ~R 306 are each independently an optionally substituted monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 25 carbon atoms; an optionally substituted monocyclic, linked or fused heteroaromatic group having 3 to 25 carbon atoms, or represents an optionally substituted linear, branched or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms; L 101 ~L 103 , L 201 ~L 206 , L 301 ~L 309 are each independently an optionally substituted monocyclic, linked or fused ring divalent aromatic hydrocarbon group having 6 to 25 carbon atoms; an optionally substituted monocyclic, linked, or fused divalent heteroaromatic group having 3 to 25 carbon atoms, or Represents a single bond; L 102 and L 103 is a single bond, R 101 and R 102 may be linked together to form a ring; X is an optionally substituted di- to tetravalent aromatic hydrocarbon group having 6 to 25 carbon atoms and being a monocyclic, linked or fused ring; an optionally substituted di- to tetravalent monocyclic, linked or fused ring heteroaromatic group having 3 to 25 carbon atoms; an optionally substituted linear, branched or cyclic divalent to tetravalent aliphatic hydrocarbon group having 1 to 20 carbon atoms; an optionally substituted di- to tetravalent cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms and being a monocyclic, linked or fused ring, or represents an optionally substituted silicon atom; a and b each independently represent an integer of 1 to 3; c and d each independently represent an integer of 1 or 2; e represents an integer of 0 or 1. According to another embodiment of the present disclosure, there is provided a metal patterning material comprising an amine compound represented by the above formula (1), (2) or (3). According to another aspect of the present disclosure, there is provided a thin film for metal patterning, which contains an amine compound represented by the above formula (1), (2) or (3) and is capable of patterning a metal film or a metal laminate film. According to another aspect of the present disclosure, there is provided an organic electroluminescence element including a cathode, the cathode containing one or more metals selected from the group consisting of lithium, ytterbium, silver, aluminum, and magnesium, or an alloy containing one or more of these metals, and patterned with a metal patterning material, the metal patterning material being an amine compound represented by the above formula (1), (2), or (3).

[0016] According to another aspect of the present disclosure, a method for producing a pattern of an organic material including an amine compound represented by the above formula (1), (2) or (3); applying a metal material to a region where the organic material pattern is formed and a region where the organic material pattern is not formed, thereby forming a metal pattern in the region where the organic material pattern is not formed.

[0017] According to another embodiment of the present disclosure, there is provided an electronic device comprising an amine compound represented by the above formula (1), (2) or (3). Effect of the Invention

[0018] According to one aspect of the present disclosure, there can be provided a novel amine compound, a material for metal patterning that suppresses the formation of a metal thin film on a film surface more than ever before, a thin film for metal patterning using the same, an organic electroluminescence element, a method for forming a metal pattern, and an electronic device. The amine compound of the present disclosure has excellent metal patterning properties and excellent adhesion to an underlayer and an adjacent thin film. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0019] Hereinafter, the amine compound, the material for metal patterning, the thin film for metal patterning, the organic electroluminescence element, the electronic device, and the method for forming the metal pattern according to one embodiment of the present disclosure will be described in detail. In this specification, the numerical range indicated by "~" indicates a range including the numerical values ​​described before and after "~" as the minimum and maximum values, respectively. In addition, unless specifically stated otherwise, the units of the numerical values ​​described before and after "~" are the same. In the numerical range described in stages in this specification, the upper limit or lower limit of a certain numerical range may be replaced by the upper limit or lower limit of a numerical range of another stage. In addition, in the numerical range described in this specification, the upper limit or lower limit of the numerical range may be replaced by the value shown in the examples. In addition, the upper limit and lower limit values ​​described individually can be arbitrarily combined. [Amine compounds] The amine compound according to one embodiment of the present disclosure is represented by formula (1), (2) or (3):

[0020] [ka]

[0021] [ka]

[0022] [ka]

[0023] In formulas (1) to (3), Ar 101 , Ar 201 , Ar 301 are each independently Any of the following formulas (4-1) to (4-7), where * represents a bond:

[0024] [ka]

[0025] In formulas (4-1) to (4-7), R 401 ~R 409 are each independently Hydrogen atoms, Deuterium atom, fluorine atom, Bromine atom, Chlorine atom, a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a fluorine atom; a linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms which may be substituted with a fluorine atom; an optionally substituted monocyclic, linked or fused ring cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms; an optionally substituted monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 25 carbon atoms; an optionally substituted monocyclic, linked or fused heteroaromatic group having 3 to 25 carbon atoms, or Represented by the following formula (5):

[0026] [ka]

[0027] In formula (5), L 501 and L 502 are each independently a linear or branched divalent aliphatic hydrocarbon group having 1 to 4 carbon atoms; Oxygen atom, Sulfur atom, or Represents a single bond, * represents a bond; n represents an integer of 3 to 11. In formula (4-1), R 401 and R 402 At least one of the following is expressed by Equation (5): In formulas (4-2) to (4-4), R 403 ~R 405 At least one of the following is expressed by Equation (5): In formulas (4-5) to (4-7), R 406 ~R 409 At least one of the following is expressed by Equation (5): In formulas (1) to (3), R 101 , R 102 , R 201 ~R 203 , R 301 ~R 306 are each independently an optionally substituted monocyclic, linked or fused ring aromatic hydrocarbon group having 6 to 25 carbon atoms; an optionally substituted monocyclic, linked or fused heteroaromatic group having 3 to 25 carbon atoms, or represents an optionally substituted linear, branched or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms; L 101 ~L 103 , L 201 ~L 206 , L 301 ~L 309 are each independently an optionally substituted monocyclic, linked or fused ring divalent aromatic hydrocarbon group having 6 to 25 carbon atoms; an optionally substituted monocyclic, linked, or fused divalent heteroaromatic group having 3 to 25 carbon atoms, or Represents a single bond; L 102 and L 103 is a single bond, R 101 and R 102 may be linked together to form a ring; X is an optionally substituted di- to tetravalent aromatic hydrocarbon group having 6 to 25 carbon atoms and being a monocyclic, linked or fused ring; an optionally substituted di- to tetravalent monocyclic, linked or fused ring heteroaromatic group having 3 to 25 carbon atoms; an optionally substituted linear, branched or cyclic divalent to tetravalent aliphatic hydrocarbon group having 1 to 20 carbon atoms; an optionally substituted di- to tetravalent cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms and being a monocyclic, linked or fused ring, or represents an optionally substituted silicon atom; a and b each independently represent an integer of 1 to 3; c and d each independently represent an integer of 1 or 2; e represents an integer of 0 or 1. Examples of the linear, branched or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a fluorine atom include a methyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a stearyl group, a cyclopentyl group, a cyclohexyl group, an adamantyl group, a diamantane group, a norbornene group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a nonafluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a perfluoroheptyl group, a perfluorooctyl group, and a perfluorocyclohexyl group. Examples of the linear, branched, or cyclic alkoxy group having 1 to 20 carbon atoms which may be substituted with a fluorine atom include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, an n-butoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group, a stearyloxy group, a difluoromethoxy group, a trifluoromethoxy group, a 2,2,2-trifluoroethoxy group, a pentafluoroethoxy group, a heptafluoropropoxy group, a nonafluorobutoxy group, a perfluoropentyloxy group, a perfluorohexyloxy group, a perfluoroheptyloxy group, and a perfluorooctyloxy group. Examples of the aromatic hydrocarbon group having 6 to 25 carbon atoms and being a single ring, a linked ring, or a condensed ring include a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthryl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, an anthryl group, a tetracenyl group, a chrysenyl group, a perylenyl group, and a pentacenyl group, as well as these groups condensed with one or more rings selected from the group consisting of benzene, naphthalene, and phenanthrene. Examples of the divalent aromatic hydrocarbon group having 6 to 25 carbon atoms and being a single ring, a linked ring, or a condensed ring include a phenylene group, a biphenylylene group, a terphenylene group, a naphthylene group, a fluorenylene group, a spirobifluorenediyl group, a benzofluorenediyl group, a dibenzofluorenediyl group, a phenanthrenediyl group, a fluoranthenediyl group, a triphenylenediyl group, an anthracenediyl group, a pyrenediyl group, a tetracenediyl group, a chrysenediyl group, a perylenediyl group, and a pentacenediyl group, as well as groups formed by condensing these groups with one or more rings selected from the group consisting of benzene, naphthalene, and phenanthrene. Examples of the trivalent aromatic hydrocarbon group having 6 to 25 carbon atoms and being a single ring, a linked ring, or a condensed ring include a phenyltriyl group, a biphenyltriyl group, a terphenyltriyl group, a naphthyltriyl group, a fluorenetriyl group, a spirobifluorenetriyl group, a benzofluorenetriyl group, a dibenzofluorenetriyl group, a phenanthrenetriyl group, a fluoranthentriyl group, a triphenylenetriyl group, a pyrenetriyl group, an anthracenetriyl group, a tetracentriyl group, a chrysentrieyl group, a perylenetriyl group, and a pentacentriyl group, as well as groups formed by condensing these groups with one or more rings selected from the group consisting of benzene, naphthalene, and phenanthrene. Examples of the tetravalent aromatic hydrocarbon group having 6 to 25 carbon atoms and being a single ring, a linked ring, or a condensed ring include a phenyltetrayl group, a biphenyltetrayl group, a terphenyltetrayl group, a naphthyltetrayl group, a fluorenetetrayl group, a spirobifluorenetetrayl group, a benzofluorenetetrayl group, a dibenzofluorenetetrayl group, a phenanthrenetetrayl group, a fluoranthenetetrayl group, a triphenylenetetrayl group, a pyrenetetrayl group, an anthracenetetrayl group, a tetracenetetrayl group, a chrysenetetrayl group, a perylenetetrayl group, and a pentacenetetrayl group, as well as groups obtained by condensing these groups with one or more rings selected from the group consisting of benzene, naphthalene, and phenanthrene. Examples of the above-mentioned monocyclic, linked, or condensed heteroaromatic group having 3 to 25 carbon atoms include a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridyl group, a pyrazyl group, a triazyl group, a pyrimidyl group, an indolyl group, a benzothienyl group, a benzofuranyl group, a benzimidazolyl group, an indazolyl group, a benzothiazolyl group, a benzisothiazolyl group, a 2,1,3-benzothiadiazolyl group, a benzyl group, a benzoisothiazolyl group, a benzo ... Examples of such groups include benzoxazolyl group, benzoisoxazolyl group, 2,1,3-benzoxadiazolyl group, quinolyl group, isoquinolyl group, carbazolyl group, dibenzothienyl group, dibenzofuranyl group, phenoxazinyl group, phenothiazinyl group, phenazinyl group, acridyl group, xanthenyl group, dibenzodioxane group, and thianthrenyl group, as well as groups formed by condensing these groups with one or more rings selected from the group consisting of benzene, naphthalene, and phenanthrene. Examples of the divalent heteroaromatic group having 3 to 25 carbon atoms and being a single ring, a linked ring, or a condensed ring include a pyrrolediyl group, a thiophenediyl group, a furandiyl group, an imidazolediyl group, a thiazolediyl group, an isothiazolediyl group, an oxazolediyl group, an isoxazolediyl group, a pyridinediyl group, a pyrazinediyl group, a triazinediyl group, a pyrimidinediyl group, an indolediyl group, a benzothiophenediyl group, a benzofurandiyl group, a benzimidazolediyl group, an indazolediyl group, a benzothiazolediyl group, a benzisothiazolediyl group, a 2,1,3-benzothiazol- Examples of such groups include diazolediyl, benzoxazolediyl, benzisoxazolediyl, 2,1,3-benzoxadiazolediyl, quinolinediyl, isoquinolinediyl, carbazolediyl, dibenzothiophenediyl, dibenzofurandiyl, phenoxazinediyl, phenothiazinediyl, phenazinediyl, acridinediyl, xanthenediyl, dibenzodioxanediyl, and thianthrenediyl groups, as well as groups formed by condensing these groups with one or more rings selected from the group consisting of benzene, naphthalene, and phenanthrene. Examples of the trivalent heteroaromatic group having 3 to 25 carbon atoms and being a monocyclic ring, a linked ring, or a condensed ring include a pyrrole triyl group, a thiophene triyl group, a furan triyl group, an imidazole triyl group, a thiazole triyl group, an isothiazole triyl group, an oxazole triyl group, an isoxazole triyl group, a pyridine triyl group, a pyrazine triyl group, a triazine triyl group, a pyrimidine triyl group, an indole triyl group, a benzothiophene triyl group, a benzofuran triyl group, a benzimidazole triyl group, an indazole triyl group, a benzothiazole triyl group, a benzisothiazole triyl group, a 2,1,3-benzo Examples of such groups include a thiadiazole triyl group, a benzoxazole triyl group, a benzisoxazole triyl group, a 2,1,3-benzoxadiazole triyl group, a quinoline triyl group, an isoquinoline triyl group, a carbazole triyl group, a dibenzothiophene triyl group, a dibenzofuran triyl group, a phenoxazine triyl group, a phenothiazine triyl group, a phenazine triyl group, an acridine triyl group, a xanthene triyl group, a dibenzodioxane triyl group, and a thianthren triyl group, as well as groups formed by condensing these groups with one or more rings selected from the group consisting of benzene, naphthalene, and phenanthrene. Examples of the tetravalent heteroaromatic group having 3 to 25 carbon atoms and being a single ring, a linked ring, or a condensed ring include a pyrroletetrayl group, a thiophenetetrayl group, a furantetrayl group, an imidazoletetrayl group, a thiazoletetrayl group, an isothiazoletetrayl group, an oxazoletetrayl group, an isoxazoletetrayl group, a pyridinetetrayl group, a pyrazinetetrayl group, a pyrimidinetetrayl group, an indoletetrayl group, a benzothiophenetetrayl group, a benzofurantetrayl group, a benzimidazoletetrayl group, an indazoletetrayl group, a benzothiazoletetrayl group, a benzisothiazoletetrayl group, a 2,1,3-benzothiadiazotetrayl group, a Examples of the tetrayl group include aryltetrayl group, benzoxazoletetrayl group, benzisoxazoletetrayl group, 2,1,3-benzoxadiazoletetrayl group, quinolinetetrayl group, isoquinolinetetrayl group, carbazoletetrayl group, dibenzothiophenetetrayl group, dibenzofurantetrayl group, phenoxazinetetrayl group, phenothiazinetetrayl group, phenazinetetrayl group, acridinetetrayl group, xanthenetetrayl group, dibenzodioxanetetrayl group, and thianthrentetrayl group, as well as these groups condensed with one or more rings selected from the group consisting of benzene, naphthalene, and phenanthrene. Examples of the above-mentioned C3-20 monocyclic, linked, or fused heterocyclic aliphatic hydrocarbon group include a morpholyl group, a piperazinyl group, a homopiperazinyl group, a hexahydro-1,3,5-triazinyl group, a 1,4-dioxanyl group, a 1,4-dithianyl group, a 4,4'-bipiperidinyl group, a diazabicyclo[2,2,2]octanyl group, an octahydro-1H-pyrrolo[3,4-b]pyridinyl group, and a 1,4,7,10-tetraazacyclododecanyl group, as well as these groups fused with one or more rings selected from the group consisting of benzene, naphthalene, and phenanthrene. Examples of the divalent cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms and being a single ring, a linked ring, or a fused ring include a morpholinediyl group, a piperazinediyl group, a homopiperazinediyl group, a hexahydro-1,3,5-triazinediyl group, a 1,4-dioxindiyl group, a 1,4-dithianediyl group, a 4,4'-bipiperidinediyl group, a diazabicyclo[2,2,2]octanediyl group, an octahydro-1H-pyrrolo[3,4-b]pyridinediyl group, and a 1,4,7,10-tetraazacyclododecanediyl group, as well as groups fused with one or more rings selected from the group consisting of benzene, naphthalene, and phenanthrene. Examples of the trivalent cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms and being a single ring, a linked ring, or a fused ring include a morpholinetriyl group, a piperazinetriyl group, a homopiperazinetriyl group, a hexahydro-1,3,5-triazinetriyl group, a 1,4-dioxintriyl group, a 1,4-dithianetriyl group, a 4,4'-bipiperidinetriyl group, a diazabicyclo[2,2,2]octanetriyl group, an octahydro-1H-pyrrolo[3,4-b]pyridinetriyl group, and a 1,4,7,10-tetraazacyclododecanetriyl group, as well as groups fused with one or more rings selected from the group consisting of benzene, naphthalene, and phenanthrene. Examples of the above-mentioned tetravalent cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms and being a single ring, a linked ring, or a fused ring include a morpholinetetrayl group, a piperazinetetrayl group, a homopiperazinetetrayl group, a 1,4-dioxinetetrayl group, a 1,4-dithianetetrayl group, a 4,4'-bipiperidinetetrayl group, a diazabicyclo[2,2,2]octanetetrayl group, an octahydro-1H-pyrrolo[3,4-b]pyridinetetrayl group, and a 1,4,7,10-tetraazacyclododecanetetrayl group, as well as groups in which one or more selected from the group consisting of benzene, naphthalene, and phenanthrene are fused to these groups. Furthermore, the following may have a substituent: a monocyclic, linked ring, or fused ring aromatic hydrocarbon group having 6 to 25 carbon atoms; a monocyclic, linked ring, or fused ring heteroaromatic group having 3 to 25 carbon atoms; a divalent to tetravalent aromatic hydrocarbon group having 6 to 25 carbon atoms; a monocyclic, linked ring, or fused ring divalent to tetravalent heteroaromatic group having 3 to 25 carbon atoms; a monocyclic, linked ring, or fused ring cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms; or a divalent to tetravalent cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms, linked ring, or fused ring. When these have a substituent, it is preferable that each of them is independently substituted with one or more groups selected from the group consisting of a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, a linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms which may be substituted with a fluorine atom, an aromatic hydrocarbon group having 6 to 25 carbon atoms which may be substituted with a fluorine atom, a heteroaromatic group having 3 to 25 carbon atoms which may be substituted with a fluorine atom, a cyano group, a fluorine atom and a deuterium atom. In this case, the number of the substituents is not particularly limited.

[0028] Specific examples of the optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 25 carbon atoms include a phenyl group, a 4-methylphenyl group, a 3-methylphenyl group, a 2-methylphenyl group, a 2,4-dimethylphenyl group, a 2,5-dimethylphenyl group, a 3,4-dimethylphenyl group, a 3,5-dimethylphenyl group, a 2,6-dimethylphenyl group, a 2,3,5-trimethylphenyl group, a 2,3,6-trimethylphenyl group, a 3,4,5-trimethylphenyl group, a 4-biphenyl group, a 3-biphenyl group, a 2-biphenyl group, a 2-methyl-1,1'-biphenyl-4-yl group, a 3-methyl-1,1'-biphenyl-4-yl group, a 2'-methyl-1,1 '-biphenyl-4-yl group, 3'-methyl-1,1'-biphenyl-4-yl group, 4'-methyl-1,1'-biphenyl-4-yl group, 2,6-dimethyl-1,1'-biphenyl-4-yl group, 2,2'-dimethyl-1,1'-biphenyl-4-yl group, 2,3'-dimethyl-1,1'-biphenyl-4-yl group, 2,4'-dimethyl-1,1'-biphenyl-4-yl group, 3,2'-dimethyl-1,1'-biphenyl-4-yl group, 2',3'-dimethyl-1,1'-biphenyl-4-yl group, 2',4'-dimethyl-1,1'-biphenyl-4-yl group, 2',5'-dimethyl-1,1'-biphenyl-4-yl group, 2',6'-dimethyl-1,1'-biphenyl-4-yl group, p-terphenyl-2-yl group, p-terphenyl-3-yl group, p-terphenyl-4-yl group, p-terphenyl-2'-yl group, m-terphenyl-2-yl group, m-terphenyl-3-yl group, m-terphenyl-4-yl group, m-terphenyl-2'-yl group, m-terphenyl-4'-yl group, m-terphenyl-5'-yl group, o-terphenyl-2-yl group, o-terphenyl-3-yl group, o-terphenyl-4-yl group, o-terphenyl-3'-yl group, o-terphenyl-4'-yl group, 1- Naphthyl group, 2-naphthyl group, 2-methylnaphthalen-1-yl group, 4-methylnaphthalen-1-yl group, 6-methylnaphthalen-2-yl group, 4-(1-naphthyl)phenyl group, 4-(2-naphthyl)phenyl group, 3-(1-naphthyl)phenyl group, 3-(2-naphthyl)phenyl group, 3-methyl-4-(1-naphthyl)phenyl group, 3-methyl-4-(2-naphthyl)phenyl group, 4-(1-naphthyl)biphenyl group, 4-(2-naphthyl)biphenyl group, 3-(1-naphthyl)biphenyl group, 3-(2-naphthyl)biphenyl group, 4-(2-methyl 3-(2-methylnaphthalen-1-yl)phenyl group, 4-phenylnaphthalen-1-yl group, 4-(2-methylphenyl)naphthalen-1-yl group, 4-(3-methylphenyl)naphthalen-1-yl group, 4-(4-methylphenyl)naphthalen-1-yl group, 6-phenylnaphthalen-2-yl group, 4-(2-methylphenyl)naphthalen-2-yl group, 4-(3-methylphenyl)naphthalen-2-yl group, 4-(4-methylphenyl)naphthalen-2-yl group, tetraphenylsilan-4-yl group, tetraphenylsilan-4-yl group, laphenylsilan-3-yl group, 2-fluorenyl group, 9,9-dimethyl-2-fluorenyl group, 9,9-diphenyl-2-fluorenyl group, 9,9-diphenyl-4-fluorenyl group, 9,9'-spirobifluoren-2-yl group, 9,9'-spirobifluoren-4-yl group, 4-(9,9'-spirobifluoren-4-yl)phenyl group, 3-(9,9'-spirobifluoren-4-yl)phenyl group, 4-(9,9'-spirobifluoren-4-yl)biphenyl group, 3-(9,9'-spirobifluoren-4-yl)biphenyl group, 4-(9,9'-diphenylfluoren-4-yl)phenyl group, 3-(9,9'-diphenylfluoren-4-yl)phenyl group, 4-(9,9'-diphenylfluoren-4-yl)biphenyl group, 3-(9,9'-diphenylfluoren-4-yl)biphenyl group, 3-(1-triphenylenyl)biphenyl group, 9-phenanthryl group, 2-phenanthryl group, 4-(9-phenanthryl)phenyl group, 3-(9-phenanthryl)phenyl group, 4-(9-phenanthryl)biphenyl group, 3-(1-naphthyl)biphenyl group, 3-(9-phenanthryl)biphenyl group, 1-triphenylenyl group, 2-triphenylenyl group, 3-triphenylenyl group, 4-triphenylenyl group, 4-(1-triphenylenyl)phenyl group, 3-(1-triphenylenyl)phenyl group, 4-(1-triphenylenyl)biphenyl group, 3-(1-triphenylenyl)biphenyl group, 3-(1-triphenylenyl)biphenyl group, 11,11'-dimethylbenzo[a]fluoren-9-yl group, 11,11'-dimethylbenzo[a]fluoren-3-yl group, 11,11'-dimethylbenzo[b]fluoren-9-yl group, 11,11'-dimethylbenzo[b]fluoren-3-yl group, 11,11'-dimethylbenzo[c]fluoren-9-yl group, 11,11'-dimethylbenzo[c]fluoren-2-yl group, 3-fluoranthenyl group, 8-fluoranthenyl group, monofluorophenyl group, difluorophenyl group, trifluorophenyl group, tetrafluorophenyl group, pentafluorophenyl group, monofluorobiphenylyl group, difluorobiphenylyl group, trifluorobiphenylyl group, tetrafluorobiphenylyl group, pentafluorobiphenylyl group, hexafluorobiphenylyl group, heptafluorobiphenylyl group, octafluorobiphenylyl group, nonafluorobiphenylyl group, monofluoroterphenylyl group, difluoroterphenylyl group, trifluoroterphenylyl group, tetrafluoroterphenylyl group, pentafluoroterphenylyl group, hexafluoro Examples of the alkyl group include a monofluoronaphthyl group, a heptafluoroterphenylyl group, an octafluoroterphenylyl group, a nonafluoroterphenylyl group, a decafluoroterphenylyl group, an undecafluoroterphenylyl group, a dodecafluoroterphenylyl group, a tridecafluoroterphenylyl group, a monofluoronaphthyl group, a difluoronaphthyl group, a trifluoronaphthyl group, a tetrafluoronaphthyl group, a pentatafluoronaphthyl group, a hexafluoronaphthyl group, a heptafluoronaphthyl group, a monofluorofluorenyl group, a difluorofluorenyl group, a trifluorofluorenyl group, a tetrafluorofluorenyl group, a pentafluorofluorenyl group, a hexafluorofluorenyl group, and a heptafluorofluorenyl group. Examples of the optionally substituted monocyclic, linked or fused heteroaromatic group having 3 to 25 carbon atoms include a 1-imidazolyl group, a 2-phenyl-1-imidazolyl group, a 2-phenyl-3,4-dimethyl-1-imidazolyl group, a 2,3,4-triphenyl-1-imidazolyl group, a 2-(2-naphthyl)-3,4-dimethyl-1-imidazolyl group, a 2-(2-naphthyl)-3,4-diphenyl-1-imidazolyl group, a 1-methyl-2-imidazolyl group, a 1-ethyl-2-imidazolyl group, a 1-phenyl ...2-imidazolyl group, a 1-phenyl-2-imidazolyl group, a 1-phenyl-2-imidazolyl group, a 1-phenyl-2-imidazolyl group, a 1-phenyl-2-imidazolyl group, a 1-phenyl-2-imidazolyl group, a 1-phenyl-2-imidazolyl group, a 1-phenyl-2-imidazolyl group, a 1-phenyl-2-imidazolyl group, a 1-phenyl- 1-methyl-4-phenyl-2-imidazolyl group, 1-methyl-4,5-dimethyl-2-imidazolyl group, 1-methyl-4,5-diphenyl-2-imidazolyl group, 1-phenyl-4,5-dimethyl-2-imidazolyl group, 1-phenyl-4,5-diphenyl-2-imidazolyl group, 1-phenyl-4,5-dibiphenylyl-2-imidazolyl group, 1-methyl-3-pyrazolyl group, 1-phenyl-3-pyrazolyl group, 1-methyl-4-pyrazolyl group, 1-phenyl-4-pyrazolyl group, 1- Methyl-5-pyrazolyl, 1-phenyl-5-pyrazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 2-pyridyl, 3-methyl-2-pyridyl, 4-methyl-2-pyridyl, 5-methyl-2-pyridyl, 6-methyl-2-pyridyl, 3-pyridyl group, 4-methyl-3-pyridyl group, 4-pyridyl group, monofluoropyridyl group, difluoropyridyl group, trifluoropyridyl group, tetrafluoropyridyl group, 2-pyrimidyl group, 2,2'-bipyridin-3-yl group, 2,2'-bipyridin-4-yl group, 2,2'-bipyridin-5-yl group, 2,3'-bipyridin-3-yl group, 2,3'-bipyridin-4-yl group, 2,3'-bipyridin-5-yl group, 5-pyrimidyl group, pyrazyl group, 1,3,5-triazyl group, 4,6-diphenyl-1,3,5-triazin-2-yl group, 1-benzimidazolyl group, 2-methyl-1-benzimidazolyl group, 2-phenyl-1-benzimidazolyl group, 1-methyl-2-benzimidazolyl group, 1-phenyl-2-benzimidazolyl group, 1-methyl-5-benzimidazolyl group, 1,2-dimethyl-5-benzimidazolyl group, 1-methyl-2-phenyl-5-benzimidazolyl group, 1-phenyl-5-benzimidazolyl group, 1,2-diphenyl-5-benzimidazolyl group 1-methyl-6-benzimidazolyl group, 1,2-dimethyl-6-benzimidazolyl group, 1-methyl-2-phenyl-6-benzimidazolyl group, 1-phenyl-6-benzimidazolyl group, 1,2-diphenyl-6-benzimidazolyl group, 1-methyl-3-indazolyl group, 1-phenyl-3-indazolyl group, 2-benzothiazolyl group, 4-benzothiazolyl group, 5-benzothiazolyl group, 6-benzothiazolyl group, 7-benzothiazolyl group benzothiazolyl group, 3-benzoisothiazolyl group, 4-benzoisothiazolyl group, 5-benzoisothiazolyl group, 6-benzoisothiazolyl group, 7-benzoisothiazolyl group, 2,1,3-benzothiadiazol-4-yl group, 2,1,3-benzothiadiazol-5-yl group, 2-benzoxazolyl group, 4-benzoxazolyl group, 5-benzoxazolyl group, 6-benzoxazolyl group, 7-benzoxazolyl group, 3-benzoisoxazolyl group, 4-benzo Isoxazolyl group, 5-benzoisoxazolyl group, 6-benzoisoxazolyl group, 7-benzoisoxazolyl group, 2,1,3-benzoxadiazolyl-4-yl group, 2,1,3-benzoxadiazolyl-5-yl group, 2-quinolyl group, 3-quinolyl group, 5-quinolyl group, 6-quinolyl group, 1-isoquinolyl group, 4-isoquinolyl group, 5-isoquinolyl group, 2-acridinyl group, 9-acridinyl group, 1,10-phenanthroline-3-yl group, 1,10-Phenanthroline-5-yl group, 2-thienyl group, 3-thienyl group, 2-benzothienyl group, 3-benzothienyl group, 2-dibenzothienyl group, 4-dibenzothienyl group, 2-furanyl group, 3-furanyl group, 2-benzofuranyl group, 3-benzofuranyl group, 2-dibenzofuranyl group, 4-dibenzofuranyl group, carbazol-9-yl group, 9-methylcarbazol-2-yl group, 9-methylcarbazol-3-yl group, 9-methylcarbazol-4-yl group, 9-phenylcarbazol-2-yl group, 9-phenylcarbazol-3-yl group , 9-phenylcarbazol-4-yl group, 9-perfluorophenylcarbazol-2-yl group, 9-perfluorophenylcarbazol-3-yl group, 9-perfluorophenylcarbazol-4-yl group, 9-perfluorotolylcarbazol-2-yl group, 9-perfluorotolylcarbazol-3-yl group, 9-perfluorotolylcarbazol-4-yl group, 9-biphenylcarbazol-2-yl group, 9-biphenylcarbazol-3-yl group, 9-biphenylcarbazol-4-yl group, 2-(9-carbazolyl)phenyl group, 3- (9-carbazolyl)phenyl group, 4-(9-carbazolyl)phenyl group, 2-(9-carbazolyl)biphenyl group, 3-(9-carbazolyl)biphenyl group, 4-(9-carbazolyl)biphenyl group, 2-(9-phenylcarbazol-3-yl)phenyl group, 3-(9-phenylcarbazol-3-yl)phenyl group, 4-(9-phenylcarbazol-3-yl)phenyl group, 2-thianthryl group, 10-phenylphenothiazin-3-yl group, 10-phenylphenothiazin-2-yl group, 10-phenylphenoxazin-3-yl group, 1 0-Phenylphenoxazin-2-yl group, 1-methylindol-2-yl group, 1-phenylindol-2-yl group, 1-methylindol-2-yl group, 1-phenylindol-2-yl group, 4-(2-pyridyl)phenyl group, 4-(3-pyridyl)phenyl group, 4-(4-pyridyl)phenyl group, 3-(2-pyridyl)phenyl group, 3-(3-pyridyl)phenyl group, 3-(4-pyridyl)phenyl group, 4-(2-phenylimidazol-1-yl)phenyl group, 4-(1-phenylimidazol-2-yl)phenyl group, 4-(2,3,4-triphenylimidazol-1-yl)phenyl group, 4-(1-methyl-4,5-diphenylimidazol-2-yl)phenyl group, 4-(2-methylbenzimidazol-1-yl)phenyl group, 4-(2-phenylbenzimidazol-1-yl)phenyl group, 4-(1-methylbenzimidazol-2-yl)phenyl group, 4-(2-phenylbenzimidazol-1-yl)phenyl group, 3-(2-methylbenzimidazol-1-yl)phenyl group, 3-(2-phenylbenzimidazol-1-yl)phenyl group, 3-(1-methylbenzimidazol-2-yl)phenyl group, 3-(2-phenylbenzimidazol-1-yl)phenyl group, 4-(3,5-diphenyltriazin-1-yl)phenyl group, 4-(2-thienyl)phenyl group, 4-(2-furanyl)phenyl group, 5-phenylthiophen-2-yl group, 5-phenylfuran-2-yl group, 4-(5-phenylthiophen-2-yl)phenyl group, 4-(5-phenylfuran-2-yl)phenyl group, 3-(5-phenylthiophen-2-yl)phenyl group, 3-(5-phenylfuran-2-yl)phenyl group, 4-(2-benzothienyl)phenyl group, 4-(3-benzothienyl)phenyl group, 3-(2-benzothienyl)phenyl group, 3-(3-benzothienyl)phenyl group, 4-(2-dibenzothienyl)phenyl group, 4-(4-dibenzothienyl)phenyl group, 3-(2-dibenzothienyl)phenyl group, 3-(4-dibenzothienyl)phenyl group, 4-(2-dibenzofuranyl)phenyl group, 4 Examples of such groups include a -(4-dibenzofuranyl)phenyl group, a 3-(2-dibenzofuranyl)phenyl group, a 3-(4-dibenzofuranyl)phenyl group, a 4-(2-benzothienyl)phenyl group, a 4-(3-benzothienyl)phenyl group, a 3-(2-benzothienyl)biphenyl group, a 3-(3-benzothienyl)biphenyl group, a 4-(2-dibenzothienyl)biphenyl group, a 4-(4-dibenzothienyl)biphenyl group, a 3-(2-dibenzothienyl)biphenyl group, a 3-(4-dibenzothienyl)biphenyl group, a 4-(2-dibenzofuranyl)biphenyl group, a 4-(4-dibenzofuranyl)biphenyl group, a 3-(2-dibenzofuranyl)biphenyl group, a 3-(4-dibenzofuranyl)biphenyl group, a 5-phenylpyridin-2-yl group, a 4-phenylpyridin-2-yl group, and a 5-phenylpyridin-3-yl group. , Specific examples of the optionally substituted di- to tetravalent aromatic hydrocarbon group having 6 to 25 carbon atoms and being a monocyclic, linked ring, or fused ring include a 1,4-phenylene group, a 1,3-phenylene group, a 1,2-phenylene group, a monofluoro-1,4-phenylene group, a difluoro-1,4-phenylene group, a trifluoro-1,4-phenylene group, a tetrafluoro-1,4-phenylene group, a monofluoro-1,3-phenylene group, a difluoro-1,3-phenylene group, a trifluoro-1,3-phenylene group, a tetrafluoro-1,3-phenylene group, a monofluoro-1,2-phenylene group, a difluoro Fluoro-1,2-phenylene group, trifluoro-1,2-phenylene group, tetrafluoro-1,2-phenylene group, 4,4'-biphenylylene group, 4,3'-biphenylylene group, 4,2'-biphenylylene group, 3,3'-biphenylylene group, 3,2'-biphenylylene group, 2,2'-biphenylylene group, monofluoro-4,4'-biphenylylene group, difluoro-4,4'-biphenylylene group, trifluoro-4,4'-biphenylylene group, tetrafluoro-4,4'-biphenylylene group, pentafluoro-4,4'-biphenylylene group, hexafluoro b-4,4'-biphenylylene group, heptafluoro-4,4'-biphenylylene group, octafluoro-4,4'-biphenylylene group, monofluoro-4,3'-biphenylylene group, difluoro-4,3'-biphenylylene group, trifluoro-4,3'-biphenylylene group, tetrafluoro-4,3'-biphenylylene group, pentafluoro-4,3'-biphenylylene group, hexafluoro-4,3'-biphenylylene group, heptafluoro-4,3'-biphenylylene group, octafluoro-4,3'-biphenylylene group, monofluoro-4,2'-biphenylylene a difluoro-4,2'-biphenylylene group, a trifluoro-4,2'-biphenylylene group, a tetrafluoro-4,2'-biphenylylene group, a pentafluoro-4,2'-biphenylylene group, a hexafluoro-4,2'-biphenylylene group, a heptafluoro-4,2'-biphenylylene group, an octafluoro-4,2'-biphenylylene group, a monofluoro-3,3'-biphenylylene group, a difluoro-3,3'-biphenylylene group, a trifluoro-3,3'-biphenylylene group, a tetrafluoro-3,3'-biphenylylene group, a pentafluoro-3,3'-biphenylylene group, hexafluoro-3,3'-biphenylylene group, heptafluoro-3,3'-biphenylylene group, octafluoro-3,3'-biphenylylene group, monofluoro-3,2'-biphenylylene group, difluoro-3,2'-biphenylylene group, trifluoro-3,2'-biphenylylene group, tetrafluoro-3,2'-biphenylylene group, pentafluoro-3,2'-biphenylylene group, hexafluoro-3,2'-biphenylylene group, heptafluoro-3,2'-biphenylylene group, octafluoro-3,2'-biphenylylene group, monofluoro-2,2'-biphenylylene group, difluoro-2,2'-biphenylylene group, trifluoro-2,2'-biphenylylene group, tetrafluoro-2,2'-biphenylylene group, pentafluoro-2,2'-biphenylylene group, hexafluoro-2,2'-biphenylylene group, heptafluoro-2,2'-biphenylylene group, octafluoro-2,2'-biphenylylene group, 2,2'-dimethyl-4,4'-biphenylylene group, 2,2'-di(trifluoromethyl)-4,4'-biphenylylene group, 4,4''-p-terphenylene group, perfluoro Fluoro-4,4''-p-terphenylene group, 4,3''-p-terphenylene group, perfluoro-4,3''-p-terphenylene group, 4,2''-p-terphenylene group, perfluoro-4,2''-p-terphenylene group, 3,3''-p-terphenylene group, perfluoro-3,3''-p-terphenylene group, 3,2''-p-terphenylene group, perfluoro-3,2''-p-terphenylene group, 2,2''-p-terphenylene group, perfluoro-2,2''-p-terphenylene group, 4,2'-p-terphenylene group, perfluoro b-4,2'-p-terphenylene group, 4,3'-p-terphenylene group, perfluoro-4,3'-p-terphenylene group, 3,2'-p-terphenylene group, perfluoro-3,2'-p-terphenylene group, 3,3'-p-terphenylene group, perfluoro-3,3'-p-terphenylene group, 2,3'-p-terphenylene group, perfluoro-2,3'-p-terphenylene group, 2,2'-p-terphenylene group, perfluoro-2,2'-p-terphenylene group, 4,4''-m-terphenylene group, 4,3''-m-terphenylene group, 4,2''-m-terphenylene group, 3,3''-m-terphenylene group, 3,2''-m-terphenylene group, 2,2''-m-terphenylene group, 4,2'-m-terphenylene group, 4,4'-m-terphenylene group, 4,5'-m-terphenylene group, 4,6'-m-terphenylene group, 3,2'-m-terphenylene group, 3,4'-m-terphenylene group, 3,5'-m-terphenylene group, 3,6'-m-terphenylene group, 2,2'-m-terphenylene group, 2,4'-m-terphenylene group, 2,5'-m-terphenylene group, 2,6 '-m-terphenylene group, perfluoro-4,4''-m-terphenylene group, perfluoro-4,3''-m-terphenylene group, perfluoro-4,2''-m-terphenylene group, perfluoro-3,3''-m-terphenylene group, perfluoro-3,2''-m-terphenylene group, perfluoro-2,2''-m-terphenylene group, perfluoro-4,2'-m-terphenylene group, perfluoro-4,4'-m-terphenylene group, perfluoro-4,5'-m-terphenylene group, perfluoro-4,6'-m-terphenylene perfluoro-3,2'-m-terphenylene group, perfluoro-3,4'-m-terphenylene group, perfluoro-3,5'-m-terphenylene group, perfluoro-3,6'-m-terphenylene group, perfluoro-2,2'-m-terphenylene group, perfluoro-2,4'-m-terphenylene group, perfluoro-2,5'-m-terphenylene group, perfluoro-2,6'-m-terphenylene group, 4,4''-o-terphenylene group, 4,3''-o-terphenylene group, 4,2''-o-terphenylene group, 3,3''- o-terphenylene group, 3,2''-o-terphenylene group, 2,2''-o-terphenylene group, 4,3'-o-terphenylene group, 4,4'-o-terphenylene group, 4,5'-o-terphenylene group, 4,6'-o-terphenylene group, 3,3'-o-terphenylene group, 3,4'-o-terphenylene group, 3,5'-o-terphenylene group, 3,6'-o-terphenylene group, 2,3'-o-terphenylene group, 2,4'-o-terphenylene group, 2,5'-o-terphenylene group, 2,6'-o-terphenylene group, perfluoro-4,4''-o-terphenylene group, perfluoro-4,3''-o-terphenylene group, perfluoro-4,2''-o-terphenylene group, perfluoro-3,3''-o-terphenylene group, perfluoro-3,2''-o-terphenylene group, perfluoro-2,2''-o-terphenylene group, perfluoro-4,3'-o-terphenylene group, perfluoro-4,4'-o-terphenylene group, perfluoro-4,5'-o-terphenylene group, perfluoro-4,6'-o-terphenylene group, perfluoro-3,3'-o-terf perfluoro-3,4'-o-terphenylene group, perfluoro-3,5'-o-terphenylene group, perfluoro-3,6'-o-terphenylene group, perfluoro-2,3'-o-terphenylene group, perfluoro-2,4'-o-terphenylene group, perfluoro-2,5'-o-terphenylene group, perfluoro-2,6'-o-terphenylene group, 1,2-naphthylene group, 1,3-naphthylene group, 1,4-naphthylene group, monofluoro-1,4-naphthylene group, difluoro-1,4-naphthylene group, trifluoro-1,4 -naphthylene group, tetrafluoro-1,4-naphthylene group, hexafluoro-1,4-naphthylene group, 1,5-naphthylene group, 1,6-naphthylene group, 1,7-naphthylene group, 1,8-naphthylene group, 2,3-naphthylene group, 2,4-naphthylene group, 2,5-naphthylene group, 2,6-naphthylene group, monofluoro-2,6-naphthylene group, difluoro-2,6-naphthylene group, trifluoro-2,6-naphthylene group, tetrafluoro-2,6-naphthylene group, pentafluoro-2,6-naphthylene group, hexafluoro-2,6-naphthylene group, 2,7-naphthylene group, 2,8-naphthylene group, 9,9-dimethyl-fluorene-2,7-diyl group, 9,9-di(trifluoromethyl)-fluorene-2,7-diyl group, 9,9-di(pentafluoroethyl)-fluorene-2,7-diyl group, 9,9-di(heptafluoropropyl)-fluorene-2,7-diyl group, 9,9-di(nonafluorobutyl)-fluorene-2,7-diyl group, 9,9-di(perfluoropentyl)-fluorene-2,7-diyl group, 9,9-di(perfluorohexyl)-fluorene-2,7-diyl group, 9,9-Di(perfluoroheptyl)-fluorene-2,7-diyl group, 9,9-di(perfluorooctyl)-fluorene-2,7-diyl group, 9,9-dimethyl-fluorene-2,8-diyl group, 9,9-dimethyl-fluorene-2,4-diyl group, 9,9-dimethyl-fluorene-2,5-diyl group, 9,9-dimethyl-fluorene-2,6-diyl group, 9,9-dimethyl-fluorene-3,6-diyl group, 9,9-diphenyl-fluorene-2,7-diyl group, 9,9-di(pentafluorophenyl)-fluorene-2,7-diyl group, 9,9-diphenyl 9,9-diphenyl-fluorene-2,8-diyl group, 9,9-diphenyl-fluorene-2,4-diyl group, 9,9-diphenyl-fluorene-2,5-diyl group, 9,9-diphenyl-fluorene-2,6-diyl group, 9,9-diphenyl-fluorene-3,6-diyl group, spirobifluorene-2,7-diyl group, perfluorospirobifluorene-2,7-diyl group, spirobifluorene-2,8-diyl group, spirobifluorene-2,4-diyl group, spirobifluorene-2,5-diyl group, spirobifluorene-2,6-diyl group, spirobifluorene-3,6-diyl group, ,6-diyl group, phenanthrene-9,10-diyl group, phenanthrene-2,9-diyl group, phenanthrene-2,10-diyl group, phenanthrene-2,8-diyl group, phenanthrene-2,7-diyl group, phenanthrene-2,6-diyl group, phenanthrene-2,5-diyl group, phenanthrene-2,14-diyl group, phenanthrene-2,3-diyl group, phenanthrene-9,10-diyl group, phenanthrene-3,10-diyl group, phenanthrene-3,9-diyl group, phenanthrene-3,8-diyl group, phenanthrene-3,7-diyl group , phenanthrene-3,6-diyl group, phenanthrene-3,5-diyl group, phenanthrene-4,10-diyl group, phenanthrene-4,9-diyl group, phenanthrene-4,8-diyl group, phenanthrene-4,7-diyl group, phenanthrene-4,6-diyl group, triphenylene-1,3-diyl group, triphenylene-1,4-diyl group, triphenylene-1,5-diyl group, triphenylene-1,6-diyl group, triphenylene-1,7-diyl group, triphenylene-1,8-diyl group, triphenylene-2,3-diyl group, triphenylene-2,4-diyl group, triphenylene-2,5-diyl group, triphenylene-2,6-diyl group, triphenylene-2,7-diyl group, triphenylene-3,5-diyl group, triphenylene-3,6-diyl group, triphenylene-4,6-diyl group, pyrene-1,3-diyl group, pyrene-1,6-diyl group, pyrene-1,8-diyl group, pyrene-2,7-diyl group, anthracene-2,6-diyl, anthracene-9,10-diyl group, perfluoroanthracene-9,10-diyl group, 9,10-diphenylanthracenediyl group, phenyl-1,2,3-triyl group, monofluoro-phenyl-1,2,3-triyl group, difluoro-phenyl-1,2,3-triyl group, trifluoro-phenyl-1,2,3-triyl group, phenyl-1,2,4-triyl group, monofluorophenyl-1,2,4-triyl group, difluorophenyl-1,2,4-triyl group, trifluorophenyl-1,2,4-triyl group, phenyl-1,3,5-triyl group, biphenyl-2,3,4-triyl group, monofluoro-biphenyl-2,3,4-triyl group, difluoro-biphenyl-2,3,4-triyl group, trifluoro-biphenyl-2,3,4-triyl group, tetrafluoro-biphenyl-2,3,4-triyl group, pentafluoro-biphenyl-2,3,4-triyl group, hexafluoro-biphenyl-2,3,4-triyl group, heptafluoro fluoro-biphenyl-2,3,4-triyl group, monofluoro-biphenyl-2,3,5-triyl group, difluoro-biphenyl-2,3,5-triyl group, trifluoro-biphenyl-2,3,5-triyl group, tetrafluoro-biphenyl-2,3,5-triyl group, pentafluoro-biphenyl-2,3,5-triyl group, hexafluoro-biphenyl-2,3,5-triyl group, heptafluoro-biphenyl-2,3,5-triyl group, monofluoro-biphenyl-2,3,6-triyl group, difluoro-biphenyl-2,3,6-triyl group, trifluoro-biphenyl-2,3,5-triyl group, Fluoro-biphenyl-2,3,6-triyl group, tetrafluoro-biphenyl-2,3,6-triyl group, pentafluoro-biphenyl-2,3,6-triyl group, hexafluoro-biphenyl-2,3,6-triyl group, heptafluoro-biphenyl-2,3,6-triyl group, monofluoro-biphenyl-2,3,2'-triyl group, difluoro-biphenyl-2,3,2'-triyl group, trifluoro-biphenyl-2,3,2'-triyl group, tetrafluoro-biphenyl-2,3,2'-triyl group, pentafluoro-biphenyl-2,3,2'-triyl group, hexafluoro-biphenyl-2,3,2'-triyl group, heptafluoro-biphenyl-2,3,2'-triyl group, monofluoro-biphenyl-2,3,3'-triyl group, difluoro-biphenyl-2,3,3'-triyl group, trifluoro-biphenyl-2,3,3'-triyl group, tetrafluoro-biphenyl-2,3,3'-triyl group, pentafluoro-biphenyl-2,3,3'-triyl group, hexafluoro-biphenyl-2,3,3'-triyl group, heptafluoro-biphenyl-2,3,3'-triyl group , monofluoro-biphenyl-2,3,4'-triyl group, difluoro-biphenyl-2,3,4'-triyl group, trifluoro-biphenyl-2,3,4'-triyl group, tetrafluoro-biphenyl-2,3,4'-triyl group, pentafluoro-biphenyl-2,3,4'-triyl group, hexafluoro-biphenyl-2,3,4'-triyl group, heptafluoro-biphenyl-2,3,4'-triyl group, monofluoro-biphenyl-2,3,5-triyl group, difluoro-biphenyl-2,3,5-triyl group, trifluoro-biphenyl- 2,3,5-triyl group, tetrafluoro-biphenyl-2,3,5-triyl group, pentafluoro-biphenyl-2,3,5-triyl group, hexafluoro-biphenyl-2,3,5-triyl group, heptafluoro-biphenyl-2,3,5-triyl group, monofluoro-biphenyl-2,3,6-triyl group, difluoro-biphenyl-2,3,6-triyl group, trifluoro-biphenyl-2,3,6-triyl group, tetrafluoro-biphenyl-2,3,6-triyl group, pentafluoro-biphenyl-2,3,6-triyl group, hexafluoro fluoro-biphenyl-2,3,6-triyl group, heptafluoro-biphenyl-2,3,6-triyl group, monofluoro-biphenyl-2,3,2'-triyl group, difluoro-biphenyl-2,3,2'-triyl group, trifluoro-biphenyl-2,3,2'-triyl group, tetrafluoro-biphenyl-2,3,2'-triyl group, pentafluoro-biphenyl-2,3,2'-triyl group, hexafluoro-biphenyl-2,3,2'-triyl group, heptafluoro-biphenyl-2,3,2'-triyl group, monofluoro-biphenyl-2,3,3'-triyl group, difluoro-biphenyl-2,3,3'-triyl group, trifluoro-biphenyl-2,3,3'-triyl group, tetrafluoro-biphenyl-2,3,3'-triyl group, pentafluoro-biphenyl-2,3,3'-triyl group, hexafluoro-biphenyl-2,3,3'-triyl group, heptafluoro-biphenyl-2,3,3'-triyl group, monofluoro-biphenyl-2,3,4'-triyl group, difluoro-biphenyl-2,3,4'-triyl group, trifluoro-biphenyl-2,3,4'-triyl group, tetrafluoro Oro-biphenyl-2,3,4'-triyl group, pentafluoro-biphenyl-2,3,4'-triyl group, hexafluoro-biphenyl-2,3,4'-triyl group, heptafluoro-biphenyl-2,3,4'-triyl group, monofluoro-biphenyl-2,5,2'-triyl group, difluoro-biphenyl-2,5,2'-triyl group, trifluoro-biphenyl-2,5,2'-triyl group, tetrafluoro-biphenyl-2,5,2'-triyl group, pentafluoro-biphenyl-2,5,2'-triyl group, hexafluoro-biphenyl-2, 5,2'-triyl group, heptafluoro-biphenyl-2,5,2'-triyl group, monofluoro-biphenyl-2,5,3'-triyl group, difluoro-biphenyl-2,5,3'-triyl group, trifluoro-biphenyl-2,5,3'-triyl group, tetrafluoro-biphenyl-2,5,3'-triyl group, pentafluoro-biphenyl-2,5,3'-triyl group, hexafluoro-biphenyl-2,5,3'-triyl group, heptafluoro-biphenyl-2,5,3'-triyl group, monofluoro-biphenyl-2,5,4'-triyl group, di Fluoro-biphenyl-2,5,4'-triyl group, trifluoro-biphenyl-2,5,4'-triyl group, tetrafluoro-biphenyl-2,5,4'-triyl group, pentafluoro-biphenyl-2,5,4'-triyl group, hexafluoro-biphenyl-2,5,4'-triyl group, heptafluoro-biphenyl-2,5,4'-triyl group, monofluoro-biphenyl-2,6,2'-triyl group, difluoro-biphenyl-2,6,2'-triyl group, trifluoro-biphenyl-2,6,2'-triyl group, tetrafluoro-biphenyl-2,6,2'-triyl group, pentafluoro-biphenyl-2,6,2'-triyl group, hexafluoro-biphenyl-2,6,2'-triyl group, heptafluoro-biphenyl-2,6,2'-triyl group, monofluoro-biphenyl-2,6,3'-triyl group, difluoro-biphenyl-2,6,3'-triyl group, trifluoro-biphenyl-2,6,3'-triyl group, tetrafluoro-biphenyl-2,6,3'-triyl group, pentafluoro-biphenyl-2,6,3'-triyl group, hexafluoro-biphenyl-2,6,3'-triyl group, Heptafluoro-biphenyl-2,6,3'-triyl group, monofluoro-biphenyl-2,6,4'-triyl group, difluoro-biphenyl-2,6,4'-triyl group, trifluoro-biphenyl-2,6,4'-triyl group, tetrafluoro-biphenyl-2,6,4'-triyl group, pentafluoro-biphenyl-2,6,4'-triyl group, hexafluoro-biphenyl-2,6,4'-triyl group, heptafluoro-biphenyl-2,6,4'-triyl group, monofluoro-biphenyl-3,4,5-triyl group, difluoro-biphenyl-3 ,4,5-triyl group, trifluoro-biphenyl-3,4,5-triyl group, tetrafluoro-biphenyl-3,4,5-triyl group, pentafluoro-biphenyl-3,4,5-triyl group, hexafluoro-biphenyl-3,4,5-triyl group, heptafluoro-biphenyl-3,4,5-triyl group, monofluoro-biphenyl-3,4,2'-triyl group, difluoro-biphenyl-3,4,2'-triyl group, trifluoro-biphenyl-3,4,2'-triyl group, tetrafluoro-biphenyl-3,4,2'-triyl group, pentafluoro fluoro-biphenyl-3,4,2'-triyl group, hexafluoro-biphenyl-3,4,2'-triyl group, heptafluoro-biphenyl-3,4,2'-triyl group, monofluoro-biphenyl-3,4,3'-triyl group, difluoro-biphenyl-3,4,3'-triyl group, trifluoro-biphenyl-3,4,3'-triyl group, tetrafluoro-biphenyl-3,4,3'-triyl group, pentafluoro-biphenyl-3,4,3'-triyl group, hexafluoro-biphenyl-3,4,3'-triyl group, heptafluoro-biphenyl-3,4,3'-triyl group, monofluoro-biphenyl-3,4,4'-triyl group, difluoro-biphenyl-3,4,4'-triyl group, trifluoro-biphenyl-3,4,4'-triyl group, tetrafluoro-biphenyl-3,4,4'-triyl group, pentafluoro-biphenyl-3,4,4'-triyl group, hexafluoro-biphenyl-3,4,4'-triyl group, heptafluoro-biphenyl-3,4, 4'-triyl group, monofluoro-biphenyl-3,5,2'-triyl group, difluoro-biphenyl-3,5,2'-triyl group, trifluoro-biphenyl-3,5,2'-triyl group, tetrafluoro-biphenyl-3,5,2'-triyl group, pentafluoro-biphenyl-3,5,2'-triyl group, hexafluoro-biphenyl-3,5,2'-triyl group, heptafluoro-biphenyl-3,5, 2'-triyl group, monofluoro-biphenyl-3,5,3'-triyl group, difluoro-biphenyl-3,5,3'-triyl group, trifluoro-biphenyl-3,5,3'-triyl group, tetrafluoro-biphenyl-3,5,3'-triyl group, pentafluoro-biphenyl-3,5,3'-triyl group, hexafluoro-biphenyl-3,5,3'-triyl group, heptafluoro-biphenyl-3,5, 3'-triyl group, monofluoro-biphenyl-3,5,4'-triyl group, difluoro-biphenyl-3,5,4'-triyl group, trifluoro-biphenyl-3,5,4'-triyl group, tetrafluoro-biphenyl-3,5,4'-triyl group, pentafluoro-biphenyl-3,5,4'-triyl group, hexafluoro-biphenyl-3,5,4'-triyl group, heptafluoro-biphenyl-3,5,4'-triyl group, o-terphenyltriyl group, monofluoro-o-terphenyltriyl group, difluoro-o-terphenyltriyl group, trifluoro-o-terphenyltriyl group, tetrafluoro-o-terphenyltriyl group, pentafluoro-o-terphenyltriyl group, hexafluoro-o-terphenyltriyl group, heptafluoro-o-terphenyltriyl group, octafluoro-o-terphenyltriyl group, nonafluoro-o-terphenyltriyl group, decafluoro-o-terphenyltriyl group, perfluoro-o-terphenyltriyl group, m-terphenyltriyl group, monofluoro-m-terphenyltriyl group, difluoro-m-terphenyltriyl group, trifluoro-m-terphenyltriyl group, tetrafluoro-m-terphenyltriyl group, pentafluoro-m-terphenyltriyl group, hexafluoro-m-terphenyltriyl group, heptafluoro, fluoro-m-terphenyltriyl group, octafluoro-m-terphenyltriyl group, nonafluoro-m-terphenyltriyl group, decafluoro-m-terphenyltriyl group, perfluoro-m-terphenyltriyl group, p-terphenyltriyl group, monofluoro-p-terphenyltriyl group, difluoro-p-terphenyltriyl group, trifluoro-p-terphenyltriyl group, tetrafluoro-p-terphenyltriyl group, pentafluoro-p-terphenyltriyl group, hexafluoro-p-terphenyltriyl group, butafluoro-p-terphenyltriyl group, octafluoro-p-terphenyltriyl group, nonafluoro-p-terphenyltriyl group, decafluoro-p-terphenyltriyl group, perfluoro-p-terphenyltriyl group, naphthalene-1,2,8-triyl group, monofluoro-naphthalene-1,2,8-triyl group, difluoro-naphthalene-1,2,8-triyl group, trifluoro-naphthalene-1,2,8-triyl group, tetrafluoro-naphthalene-1,2,8-triyl group, pentafluoro-naphthalene-1,2,8-triyl group naphthalene-1,3,8-triyl group, monofluoro-naphthalene-1,3,8-triyl group, difluoro-naphthalene-1,3,8-triyl group, trifluoro-naphthalene-1,3,8-triyl group, tetrafluoro-naphthalene-1,3,8-triyl group, pentafluoro-naphthalene-1,3,8-triyl group, naphthalene-1,4,8-triyl group, monofluoro-naphthalene-1,4,8-triyl group, difluoro-naphthalene-1,4,8-triyl group, trifluoro-naphthalene-1,4,8-triyl group, tetrafluoro- Naphthalene-1,4,8-triyl group, pentafluoro-naphthalene-1,4,8-triyl group, naphthalene-1,2,3-triyl group, monofluoro-naphthalene-1,2,3-triyl group, difluoro-naphthalene-1,2,3-triyl group, trifluoro-naphthalene-1,2,3-triyl group, tetrafluoro-naphthalene-1,2,3-triyl group, pentafluoro-naphthalene-1,2,3-triyl group, naphthalene-1,2,4-triyl group, monofluoro-naphthalene-1,2,4-triyl group, difluoro-naphthalene-1,2,4-triyl group, trifluoro-naphthalene-1,2,4-triyl group, tetrafluoro-naphthalene-1,2,4-triyl group, pentafluoro-naphthalene-1,2,4-triyl group, naphthalene-1,2,5-triyl group, monofluoro-naphthalene-1,2,5-triyl group, difluoro-naphthalene-1,2,5-triyl group, trifluoro-naphthalene-1,2,5-triyl group, tetrafluoro-naphthalene-1,2,5-triyl group, pentafluoro-naphthalene-1,2,5-triyl group, naphthalene-1,2,6-triyl group , monofluoro-naphthalene-1,2,6-triyl group, difluoro-naphthalene-1,2,6-triyl group, trifluoro-naphthalene-1,2,6-triyl group, tetrafluoro-naphthalene-1,2,6-triyl group, pentafluoro-naphthalene-1,2,6-triyl group, naphthalene-1,2,7-triyl group, monofluoro-naphthalene-1,2,7-triyl group, difluoro-naphthalene-1,2,7-triyl group, trifluoro-naphthalene-1,2,7-triyl group, tetrafluoro-naphthalene-1,2,7 ... pentafluoro-naphthalene-1,2,7-triyl group, naphthalene-2,3,6-triyl group, monofluoro-naphthalene-2,3,6-triyl group, difluoro-naphthalene-2,3,6-triyl group, trifluoro-naphthalene-2,3,6-triyl group, tetrafluoro-naphthalene-2,3,6-triyl group, pentafluoro-naphthalene-2,3,6-triyl group, naphthalene-2,3,5-triyl group, monofluoro-naphthalene-2,3,5-triyl group, difluoro-naphthalene-2,3,5-triyl group, trifluoro-naphthalene naphthalene-2,3,5-triyl group, tetrafluoro-naphthalene-2,3,5-triyl group, pentafluoro-naphthalene-2,3,5-triyl group, naphthalene-1,3,5-triyl group, monofluoro-naphthalene-1,3,5-triyl group, difluoro-naphthalene-1,3,5-triyl group, trifluoro-naphthalene-1,3,5-triyl group, tetrafluoro-naphthalene-1,3,5-triyl group, pentafluoro-naphthalene-1,3,5-triyl group, naphthalene-1,3,6-triyl group, monofluoro-naphthalene-1,3,6-triyl group, difluoro-naphthalene-1,3,6-triyl group, trifluoro-naphthalene-1,3,6-triyl group, tetrafluoro-naphthalene-1,3,6-triyl group, pentafluoro-naphthalene-1,3,6-triyl group, naphthalene-1,4,6-triyl group, monofluoro-naphthalene-1,4,6-triyl group, difluoro-naphthalene-1,4,6-triyl group, trifluoro-naphthalene-1,4,6-triyl group, tetrafluoro-naphthalene-1,4,6-triyl group, pentafluoro-naphthalene-1,4,6- triyl group, 9,9-dimethyl-fluorene-triyl group, 9,9-di(trifluoromethyl)-fluorene-triyl group, 9,9-di(pentafluoroethyl)-fluorene-triyl group, 9,9-di(heptafluoropropyl)-fluorene-triyl group, 9,9-di(nonafluorobutyl)-fluorene-triyl group, 9,9-di(perfluoropentyl)-fluorene-triyl group, 9,9-di(perfluorohexyl)-fluorene-triyl group, 9,9-di(perfluoroheptyl)-fluorene-triyl group, 9,9-di(perfluoro 9,9-di(pentafluorophenyl)-fluorene-triyl group, 9,9-diphenyl-fluorene-triyl group, 9,9-di(pentafluorophenyl)-fluorene-triyl group, spirobifluorene-triyl group, perfluorospirobifluorene-triyl group, spirobifluorene-triyl group, phenanthrene-triyl group, monofluoro-phenanthrene-triyl group, difluoro-phenanthrene-triyl group, trifluoro-phenanthrene-triyl group, tetrafluoro-phenanthrene-triyl group, pentafluoro-phenanthrene-triyl group, heptafen-triyl group, xanthfluoro-phenanthrene-triyl group, triphenylene-triyl group, anthracene-triyl group, perfluoroanthracene-triyl group, 9,10-diphenylanthracene-triyl group, phenyl-1,2,3,4-tetrayl group, monofluoro-phenyl-1,2,3,4-tetrayl group, difluoro-phenyl-1,2,3,4-tetrayl group, phenyl-1,2,3,5-tetrayl group, monofluoro-phenyl-1,2,3,5-tetrayl group, difluoro-phenyl-1,2,3,5-tetrayl group, phenyl-1,2,4,5-tetrayl group, monofluoro-phenyl-1,2,4,5-tetrayl group, difluoro-phenyl-1,2,4,5-tetrayl group, 5-trifluoromethyl-phenyl-1,2,3,4-tetrayl group, 5-trifluoromethyl-6-fluoro-phenyl-1,2,3,4-tetrayl group, 5,6-bis(trifluoromethyl)phenyl-1,2,3,4-tetrayl group, 4-trifluoromethyl-phenyl-1,2,3,5-tetrayl group, 4-trifluoromethyl-6-fluoro-phenyl-1,2,3,5-tetrayl group, 4,6-bis( trifluoromethyl)phenyl-1,2,3,5-tetrayl group, 3-trifluoromethyl-phenyl-1,2,4,5-tetrayl group, 3-trifluoromethyl-6-fluoro-phenyl-1,2,4,5-tetrayl group, 3,6-bis(trifluoromethyl)phenyl-1,2,4,5-tetrayl group, biphenyl-2,3,4,3'-tetrayl group, monofluoro-biphenyl-2,3,4,3'-tetrayl group, difluoro-biphenyl-2,3,4,3'-tetrayl group, trifluoro-biphenyl-2,3,4,3'-tetrayl group, tetrafluoro trifluorobiphenyl-2,3,4,3'-tetrayl group, pentafluorobiphenyl-2,3,4,3'-tetrayl group, hexafluorobiphenyl-2,3,4,3'-tetrayl group, biphenyl-2,3,5,3'-tetrayl group, monofluorobiphenyl-2,3,5,3'-tetrayl group, difluorobiphenyl-2,3,5,3'-tetrayl group, trifluorobiphenyl-2,3,5,3'-tetrayl group, tetrafluorobiphenyl-2,3,5,3'-tetrayl group, pentafluorobiphenyl-2,3,5,3' -tetrayl group, hexafluoro-biphenyl-2,3,5,3'-tetrayl group, biphenyl-2,4,5,3'-tetrayl group, monofluoro-biphenyl-2,4,5,3'-tetrayl group, difluoro-biphenyl-2,4,5,3'-tetrayl group, trifluoro-biphenyl-2,4,5,3'-tetrayl group, tetrafluoro-biphenyl-2,4,5,3'-tetrayl group, pentafluoro-biphenyl-2,4,5,3'-tetrayl group, hexafluoro-biphenyl-2,4,5,3'-tetrayl group, biphenyl-3,4,5,3'-tetrayl group, monofluoro-biphenyl-3,4,5,3'-tetrayl group, difluoro-biphenyl-3,4,5,3'-tetrayl group, trifluoro-biphenyl-3,4,5,3'-tetrayl group, tetrafluoro-biphenyl-3,4,5,3'-tetrayl group, pentafluoro-biphenyl-3,4,5,3'-tetrayl group, hexafluoro-biphenyl-3,4,5,3'-tetrayl group, biphenyl-2,3,4,5-tetrayl group, monofluoro-biphenyl-2,3,4,5-tetrayl group, difluoro-biphenyl-2,3 ,4,5-tetrayl group, trifluoro-biphenyl-2,3,4,5-tetrayl group, tetrafluoro-biphenyl-2,3,4,5-tetrayl group, pentafluoro-biphenyl-2,3,4,5-tetrayl group, hexafluoro-biphenyl-2,3,4,5-tetrayl group, biphenyl-2,3,6,3'-tetrayl group, monofluoro-biphenyl-2,3,6,3'-tetrayl group, difluoro-biphenyl-2,3,6,3'-tetrayl group, trifluoro-biphenyl-2,3,6,3'-tetrayl group, tetrafluoro-biphenyl-2 ,3,6,3'-tetrayl group, pentafluoro-biphenyl-2,3,6,3'-tetrayl group, hexafluoro-biphenyl-2,3,6,3'-tetrayl group, biphenyl-2,4,6,3'-tetrayl group, monofluoro-biphenyl-2,4,6,3'-tetrayl group, difluoro-biphenyl-2,4,6,3'-tetrayl group, trifluoro-biphenyl-2,4,6,3'-tetrayl group, tetrafluoro-biphenyl-2,4,6,3'-tetrayl group, pentafluoro-biphenyl-2,4,6,3'-tetrayl group, hexafluoro -biphenyl-2,4,6,3'-tetrayl group, biphenyl-2,3,4,6-tetrayl group, monofluoro-biphenyl-2,3,4,6-tetrayl group, difluoro-biphenyl-2,3,4,6-tetrayl group, trifluoro-biphenyl-2,3,4,6-tetrayl group, tetrafluoro-biphenyl-2,3,4,6-tetrayl group, pentafluoro-biphenyl-2,3,4,6-tetrayl group, hexafluoro-biphenyl-2,3,4,6-tetrayl group, biphenyl-2,3,5,6-tetrayl group, monofluoro-biphenyl-2,3,5,6-tetrayl group, difluoro-biphenyl-2,3,5,6-tetrayl group, trifluoro-biphenyl-2,3,5,6-tetrayl group, tetrafluoro-biphenyl-2,3,5,6-tetrayl group, pentafluoro-biphenyl-2,3,5,6-tetrayl group, hexafluoro-biphenyl-2,3,5,6-tetrayl group, biphenyl-2,5,2',3', -tetrayl group, monofluoro-biphenyl-2,5,2',3'-tetrayl group, difluoro-biphenyl-2,5,2',3'-tetrayl group, trifluoro-biphenyl-2,5,2',3'-tetrayl group, tetrafluoro-biphenyl-2,5,2',3'-tetrayl group, pentafluoro-biphenyl-2,5,2',3'-tetrayl group, hexafluoro-biphenyl-2,5,2',3'-tetrayl group, biphenyl-2,4,2',5'-tetrayl group, monofluoro-biphenyl-2,4,2',5'-tetrayl group, difluoro -biphenyl-2,4,2',5'-tetrayl group, trifluoro-biphenyl-2,4,2',5'-tetrayl group, tetrafluoro-biphenyl-2,4,2',5'-tetrayl group, pentafluoro-biphenyl-2,4,2',5'-tetrayl group, hexafluoro-biphenyl-2,4,2',5'-tetrayl group, biphenyl-2,5,3',4'-tetrayl group, monofluoro-biphenyl-2,5,3',4'-tetrayl group, difluoro-biphenyl-2,5,3',4'-tetrayl group, trifluoro-biphenyl-2,5,3' ,4'-tetrayl group, tetrafluoro-biphenyl-2,5,3',4'-tetrayl group, pentafluoro-biphenyl-2,5,3',4'-tetrayl group, hexafluoro-biphenyl-2,5,3',4'-tetrayl group, biphenyl-2,3,4,2'-tetrayl group, monofluoro-biphenyl-2,3,4,2'-tetrayl group, difluoro-biphenyl-2,3,4,2'-tetrayl group, trifluoro-biphenyl-2,3,4,2'-tetrayl group, tetrafluoro-biphenyl-2,3,4,2'-tetrayl group, pentafluoro biphenyl-2,3,4,2'-tetrayl group, hexafluoro-biphenyl-2,3,4,2'-tetrayl group, biphenyl-2,5,2',5'-tetrayl group, monofluoro-biphenyl-2,5,2',5'-tetrayl group, difluoro-biphenyl-2,5,2',5'-tetrayl group, trifluoro-biphenyl-2,5,2',5'-tetrayl group, tetrafluoro-biphenyl-2,5,2',5'-tetrayl group, pentafluoro-biphenyl-2,5,2',5'-tetrayl group, hexafluoro-biphenyl-2,5,2',5'-tetrayl group, biphenyl-2,5,3',5'-tetrayl group, monofluoro-biphenyl-2,5,3',5'-tetrayl group, difluoro-biphenyl-2,5,3',5'-tetrayl group, trifluoro-biphenyl-2,5,3',5'-tetrayl group, tetrafluoro-biphenyl-2,5,3',5'-tetrayl group, pentafluoro-biphenyl-2,5,3',5'-tetrayl group, hexafluoro-biphenyl-2,5,3',5'-tetrayl group, biphenyl-2,3,5,2'-tetrayl group, monofluoro-biphenyl- 2,3,5,2'-tetrayl group, difluoro-biphenyl-2,3,5,2'-tetrayl group, trifluoro-biphenyl-2,3,5,2'-tetrayl group, tetrafluoro-biphenyl-2,3,5,2'-tetrayl group, pentafluoro-biphenyl-2,3,5,2''-tetrayl group, hexafluoro-biphenyl-2,3,5,2'-tetrayl group, biphenyl-2,4,5,2'-tetrayl group, monofluoro-biphenyl-2,4,5,2'-tetrayl group, difluoro-biphenyl-2,4,5,2'-tetrayl group, trifluoro- biphenyl-2,4,5,2'-tetrayl group, tetrafluoro-biphenyl-2,4,5,2'-tetrayl group, pentafluoro-biphenyl-2,4,5,2'-tetrayl group, hexafluoro-biphenyl-2,4,5,2'-tetrayl group, biphenyl-3,4,5,2'-tetrayl group, monofluoro-biphenyl-3,4,5,2'-tetrayl group, difluoro-biphenyl-3,4,5,2'-tetrayl group, trifluoro-biphenyl-3,4,5,2'-tetrayl group, tetrafluoro-biphenyl-3,4,5,2'-tetrayl group, Pentafluoro-biphenyl-3,4,5,2'-tetrayl group, hexafluoro-biphenyl-3,4,5,2'-tetrayl group, biphenyl-2,5,2',6'-tetrayl group, monofluoro-biphenyl-2,5,2',6'-tetrayl group, difluoro-biphenyl-2,5,2',6'-tetrayl group, trifluoro-biphenyl-2,5,2',6'-tetrayl group, tetrafluoro-biphenyl-2,5,2',6'-tetrayl group, pentafluoro-biphenyl-2,5,2',6'-tetrayl group, hexafluoro-biphenyl-2,5,2',6'-tetrayl group, biphenyl-2,3,6,2'-tetrayl group, monofluoro-biphenyl-2,3,6,2'-tetrayl group, difluoro-biphenyl-2,3,6,2'-tetrayl group, trifluoro-biphenyl-2,3,6,2'-tetrayl group, tetrafluoro-biphenyl-2,3,6,2'-tetrayl group, pentafluoro-biphenyl-2,3,6,2'-tetrayl group, hexafluoro-biphenyl-2,3,6,2'-tetrayl group, biphenyl-2,4,6,2'-tetrayl group, monofluoro-biphenyl biphenyl-2,4,6,2'-tetrayl group, difluoro-biphenyl-2,4,6,2'-tetrayl group, trifluoro-biphenyl-2,4,6,2'-tetrayl group, tetrafluoro-biphenyl-2,4,6,2'-tetrayl group, pentafluoro-biphenyl-2,4,6,2'-tetrayl group, hexafluoro-biphenyl-2,4,6,2'-tetrayl group, biphenyl-2,3,3',4'-tetrayl group, monofluoro-biphenyl-2,3,3',4'-tetrayl group, difluoro-biphenyl-2,3,3',4'-tetrayl group , trifluoro-biphenyl-2,3,3',4'-tetrayl group, tetrafluoro-biphenyl-2,3,3',4'-tetrayl group, pentafluoro-biphenyl-2,3,3',4'-tetrayl group, hexafluoro-biphenyl-2,3,3',4'-tetrayl group, biphenyl-2,4,3',4'-tetrayl group, monofluoro-biphenyl-2,4,3',4'-tetrayl group, difluoro-biphenyl-2,4,3',4'-tetrayl group, trifluoro-biphenyl-2,4,3',4'-tetrayl group, tetrafluoro-biphenyl biphenyl-2,4,3',4'-tetrayl group, pentafluoro-biphenyl-2,4,3',4'-tetrayl group, hexafluoro-biphenyl-2,4,3',4'-tetrayl group, biphenyl-3,4,3',4'-tetrayl group, monofluoro-biphenyl-3,4,3',4'-tetrayl group, difluoro-biphenyl-3,4,3',4'-tetrayl group, trifluoro-biphenyl-3,4,3',4'-tetrayl group, tetrafluoro-biphenyl-3,4,3',4'-tetrayl group, pentafluoro-biphenyl-3,4,3',4'-tetrayl group, hexafluoro-biphenyl-3,4,3',4'-tetrayl group, biphenyl-2,3,4,4'-tetrayl group, monofluoro-biphenyl-2,3,4,4'-tetrayl group, difluoro-biphenyl-2,3,4,4'-tetrayl group, trifluoro-biphenyl-2,3,4,4'-tetrayl group, tetrafluoro-biphenyl-2,3,4,4'-tetrayl group, pentafluoro-biphenyl-2,3,4,4'-tetrayl group, hexafluoro-biphenyl-2,3,4,4'-tetrayl group, biphenyl-3,4, 3',5'-tetrayl group, monofluoro-biphenyl-3,4,3',5'-tetrayl group, difluoro-biphenyl-3,4,3',5'-tetrayl group, trifluoro-biphenyl-3,4,3',5'-tetrayl group, tetrafluoro-biphenyl-3,4,3',5'-tetrayl group, pentafluoro-biphenyl-3,4,3',5'-tetrayl group, hexafluoro-biphenyl-3,4,3',5'-tetrayl group, biphenyl-2,3,5,4'-tetrayl group, monofluoro-biphenyl-2,3,5,4'-tetrayl group, difluoro biphenyl-2,3,5,4'-tetrayl group, trifluorobiphenyl-2,3,5,4'-tetrayl group, tetrafluorobiphenyl-2,3,5,4'-tetrayl group, pentafluorobiphenyl-2,3,5,4'-tetrayl group, hexafluorobiphenyl-2,3,5,4'-tetrayl group, biphenyl-2,4,5,4'-tetrayl group, monofluorobiphenyl-2,4,5,4'-tetrayl group, difluorobiphenyl-2,4,5,4'-tetrayl group, trifluorobiphenyl-2,4,5,4'-tetrayl group group, tetrafluoro-biphenyl-2,4,5,4'-tetrayl group, pentafluoro-biphenyl-2,4,5,4'-tetrayl group, hexafluoro-biphenyl-2,4,5,4'-tetrayl group, biphenyl-3,4,5,4'-tetrayl group, monofluoro-biphenyl-3,4,5,4'-tetrayl group, difluoro-biphenyl-3,4,5,4'-tetrayl group, trifluoro-biphenyl-3,4,5,4'-tetrayl group, tetrafluoro-biphenyl-3,4,5,4'-tetrayl group, pentafluoro-biphenyl-3,4,5,4'-tetrayl group, hexafluoro-biphenyl-3,4,5,4'-tetrayl group, biphenyl-2,6,3',4'-tetrayl group, monofluoro-biphenyl-2,6,3',4'-tetrayl group, difluoro-biphenyl-2,6,3',4'-tetrayl group, trifluoro-biphenyl-2,6,3',4'-tetrayl group, tetrafluoro-biphenyl-2,6,3',4'-tetrayl group, pentafluoro-biphenyl-2,6,3',4'-tetrayl group, hexafluoro-biphenyl-2,6,3',4'-tetrayl group, biphenyl biphenyl-2,3,6,4'-tetrayl group, monofluoro-biphenyl-2,3,6,4-tetrayl group, difluoro-biphenyl-2,3,6,4-tetrayl group, trifluoro-biphenyl-2,3,6,4-tetrayl group, tetrafluoro-biphenyl-2,3,6,4-tetrayl group, pentafluoro-biphenyl-2,3,6,4-tetrayl group, hexafluoro-biphenyl-2,3,6,4-tetrayl group, biphenyl-2,4,6,4'-tetrayl group, monofluoro-biphenyl-2,4,6,4-tetrayl group, difluoro-biphenyl- 2,4,6,4-tetrayl group, trifluoro-biphenyl-2,4,6,4-tetrayl group, tetrafluoro-biphenyl-2,4,6,4-tetrayl group, pentafluoro-biphenyl-2,4,6,4-tetrayl group, hexafluoro-biphenyl-2,4,6,4-tetrayl group, biphenyl-2,3,2',4'-tetrayl group, monofluoro-biphenyl-2,3,2',4'-tetrayl group, difluoro-biphenyl-2,3,2',4'-tetrayl group, trifluoro-biphenyl-2,3,2',4'-tetrayl group, tetrafluoro -biphenyl-2,3,2',4'-tetrayl group, pentafluoro-biphenyl-2,3,2',4'-tetrayl group, hexafluoro-biphenyl-2,3,2',4'-tetrayl group, biphenyl-2,4,2',4'-tetrayl group, monofluoro-biphenyl-2,4,2',4'-tetrayl group, difluoro-biphenyl-2,4,2',4'-tetrayl group, trifluoro-biphenyl-2,4,2',4'-tetrayl group, tetrafluoro-biphenyl-2,4,2',4'-tetrayl group, pentafluoro-biphenyl-2,4,2',4'-tetrayl group, hexafluoro-biphenyl-2,4,2',4'-tetrayl group, biphenyl-3,5,2',4'-tetrayl group, monofluoro-biphenyl-3,5,2',4'-tetrayl group, difluoro-biphenyl-3,5,2',4'-tetrayl group, trifluoro-biphenyl-3,5,2',4'-tetrayl group, tolyl group, tetrafluoro-biphenyl-3,5,2',4'-tetrayl group, pentafluoro-biphenyl-3,5,2',4'-tetrayl group, hexafluoro-biphenyl-3,5,2',4'-tetrayl group, biphenyl-2,4,2',6'-tetrayl group, monofluoro-biphenyl-2,4,2',6-tetrayl group, difluoro-biphenyl-2,4,2',6-tetrayl group, trifluoro-biphenyl-2,4,2',6-tetrayl group, tetrafluoro-biphenyl-2,4,2',6-tetrayl group, pentafluoro- Biphenyl-2,4,2',6-tetrayl group, hexafluoro-biphenyl-2,4,2',6-tetrayl group, biphenyl-2,3,2',3'-tetrayl group, monofluoro-biphenyl-2,3,2',3'-tetrayl group, difluoro-biphenyl-2,3,2',3'-tetrayl group, trifluoro-biphenyl-2,3,2',3'-tetrayl group, tetrafluoro-biphenyl-2,3,2',3'-tetrayl group, pentafluoro-biphenyl-2,3,2',3'-tetrayl group, hexafluoro-biphenyl-2,3,2' ,3'-tetrayl group, biphenyl-2,3,3',5'-tetrayl group, monofluoro-biphenyl-2,3,3',5'-tetrayl group, difluoro-biphenyl-2,3,3',5'-tetrayl group, trifluoro-biphenyl-2,3,3',5'-tetrayl group, tetrafluoro-biphenyl-2,3,3',5'-tetrayl group, pentafluoro-biphenyl-2,3,3',5'-tetrayl group, hexafluoro-biphenyl-2,3,3',5'-tetrayl group, biphenyl-2,3,2',6'-tetrayl group, monofluoro- Biphenyl-2,3,2',6'-tetrayl group, difluoro-biphenyl-2,3,2',6'-tetrayl group, trifluoro-biphenyl-2,3,2',6'-tetrayl group, tetrafluoro-biphenyl-2,3,2',6'-tetrayl group, pentafluoro-biphenyl-2,3,2',6'-tetrayl group, hexafluoro-biphenyl-2,3,2',6'-tetrayl group, biphenyl-3,5,2',6'-tetrayl group, monofluoro-biphenyl-3,5,2',6'-tetrayl group, difluoro-biphenyl-3,5,2',6'-tetrayl group, trifluoro-biphenyl-3,5,2',6'-tetrayl group, tetrafluoro-biphenyl-3,5,2',6'-tetrayl group, pentafluoro-biphenyl-3,5,2',6'-tetrayl group, hexafluoro-biphenyl-3,5,2',6'-tetrayl group, biphenyl-2,6,2',6'-tetrayl group, monofluoro-biphenyl-2,6,2',6'-tetrayl group, difluoro-biphenyl-2,6,2',6'-tetrayl group, trifluoro-biphenyl-2,6,2',6'-tetrayl group, tetrafluoro-biphenyl-2,6,2', 6'-tetrayl group, pentafluoro-biphenyl-2,6,2',6'-tetrayl group, hexafluoro-biphenyl-2,6,2',6'-tetrayl group, biphenyl-3,5,3',5'-tetrayl group, monofluoro-biphenyl-3,5,3',5'-tetrayl group, difluoro-biphenyl-3,5,3',5'-tetrayl group, trifluoro-biphenyl-3,5,3',5'-tetrayl group, tetrafluoro-biphenyl-3,5,3',5'-tetrayl group, pentafluoro-biphenyl-3,5,3',5'-tetrayl group, hexafluoro-biphenyl-3,5,3',5'-tetrayl group, o-terphenyltetrayl group, monofluoro-o-terphenyltetrayl group, difluoro-o-terphenyltetrayl group, trifluoro-o-terphenyltetrayl group, tetrafluoro-o-terphenyltetrayl group, pentafluoro-o-terphenyltetrayl group, hexafluoro-o-terphenyltetrayl group, heptafluoro-o-terphenyltetrayl group, octafluoro-o-terphenyltetrayl group, nonafluoro-o-terphenyltetrayl group, decafluoro-o-terphenyltetrayl group, m-terphenyltetrayl group, monofluoro-m-terphenyltetrayl group, difluoro-m-terphenyltetrayl group, trifluoro-m-terphenyltetrayl group, tetrafluoro-m-terphenyltetrayl group, pentafluoro-m-terphenyltetrayl group, hexafluoro-m-terphenyltetrayl group, heptafluoro-m-terphenyltetrayl group, octafluoro-m-terphenyltetrayl group, nonafluoro-m-terphenyltetrayl group, decafluoro-m-terphenyltetrayl group, perfluoro-m-terphenyltetrayl group, phenyltetrayl group, p-terphenyltetrayl group, monofluoro-p-terphenyltetrayl group, difluoro-p-terphenyltetrayl group, trifluoro-p-terphenyltetrayl group, tetrafluoro-p-terphenyltetrayl group, pentafluoro-p-terphenyltetrayl group, hexafluoro-p-terphenyltetrayl group, heptafluoro-p-terphenyltetrayl group, octafluoro-p-terphenyltetrayl group, nonafluoro-p-terphenyltetrayl group, decafluoro-p-terphenyltetrayl group, Perfluoro-p-terphenyltetrayl group, naphthalene-1,4,5,8-tetrayl group, monofluoro-naphthalene-1,4,5,8-tetrayl group, difluoro-naphthalene-1,4,5,8-tetrayl group, trifluoro-naphthalene-1,4,5,8-tetrayl group, tetrafluoro-1,4,5,8-naphthalene-tetrayl group, naphthalene-2,3,6,7-tetrayl group, monofluoro-naphthalene-2,3,6,7-tetrayl group, difluoro-naphthalene-2,3,6,7-tetrayl group, trifluoro-naphthalene-2,3,6,7-tetrayl group, tetrafluoro-2,3,6,7-naphthalene-tetrayl group, 9,9-dimethyl-fluorene-tetrayl group, 9,9-di(trifluoromethyl)-fluorene-tetrayl group, 9,9-di(pentafluoroethyl)-fluorene-tetrayl group, 9,9-di(heptafluoropropyl)-fluorene-tetrayl group, 9,9-di(nonafluorobutyl)-fluorene-tetrayl group, 9,9-di(perfluoropentyl)-fluorene-tetrayl group, 9,9-di(perfluorohexyl)-fluorene-tetrayl group, 9,9-di(perfluoroheptyl)-fluorene-tetrayl group, 9,9-di(perfluorooctyl)-fluorene-tetrayl group, 9,9-diphenyl Examples of the fluorene-tetrayl group include a fluorene-tetrayl group, a 9,9-di(pentafluorophenyl)-fluorene-tetrayl group, a spirobifluorene-tetrayl group, a perfluorospirobifluorene-tetrayl group, a spirobifluorene-tetrayl group, a phenanthrene-tetrayl group, a monofluoro-phenanthrene-tetrayl group, a difluoro-phenanthrene-tetrayl group, a trifluoro-phenanthrene-tetrayl group, a tetrafluoro-phenanthrene-tetrayl group, a pentafluoro-phenanthrene-tetrayl group, a triphenylene-tetrayl group, an anthracene-tetrayl group, a perfluoroanthracene-tetrayl group, and a 9,10-diphenylanthracene-tetrayl group. Specific examples of the optionally substituted di- to tetravalent heteroaromatic group having 3 to 25 carbon atoms and being a monocyclic, linked or fused ring include a thiophene-diyl group, a furan-diyl group, a pyridine-2,3-diyl group, a pyridine-2,4-diyl group, a pyridine-2,5-diyl group, a pyridine-2,6-diyl group, a pyridine-3,4-diyl group, a pyridine-3,5-diyl group, a perfluoropyridine-2,3-diyl group, a perfluoropyridine-2,4-diyl group, a perfluoropyridine-2,5-diyl group, a perfluoropyridine-2,6-diyl group, Perfluoropyridine-3,4-diyl group, perfluoropyridine-3,5-diyl group, dibenzofuran-2,7-diyl group, dibenzofuran-1,4-diyl group, dibenzofuran-3,6-diyl group, dibenzofuran-4,5-diyl group, dibenzothiophene-2,7-diyl group, dibenzothiophene-4,5-diyl group, dibenzothiophene-1,4-diyl group, dibenzothiophene-3,6-diyl group, 9-phenylcarbazole-2,7-diyl group, 9-perfluorophenylcarbazole-2,7-diyl group, 9- Perfluorotolylcarbazole-2,7-diyl group, 9-perfluoropyridylcarbazole-2,7-diyl group, 9-phenylcarbazole-3,6-diyl group, 9-perfluorophenylcarbazole-3,6-diyl group, 9-perfluorotolylcarbazole-3,6-diyl group, 9-perfluoropyridylcarbazole-3,6-diyl group, pyrimidine-2,4-diyl group, pyrimidine-2,5-diyl group, pyrimidine-4,6-diyl group, pyrimidine-4,5-diyl group, triazine-2,4-diyl group, pyridinyl Fluorine-2,3,4-triyl group, monofluoropyridine-2,3,4-triyl group, difluoropyridine-2,3,4-triyl group, pyridine-2,3,5-triyl group, monofluoropyridine-2,3,5-triyl group, difluoropyridine-2,3,5-triyl group, pyridine-2,3,6-triyl group, monofluoropyridine-2,3,6-triyl group, difluoropyridine-2,3,6-triyl group, pyridine-3,4,5-triyl group, monofluoropyridine-3,4,5-triyl group, difluoropyridine-3,4,Examples of the aryl group include 5-triyl group, dibenzofuran-triyl group, dibenzothiophene-triyl group, 9-phenylcarbazole-triyl group, pyrimidine-2,4,6-triyl group, pyrimidine-4,5,6-triyl group, pyrimidine-2,4,5-triyl group, triazine-2,4,6-triyl group, pyridine-2,3,4,5-tetrayl group, monofluoropyridine-2,3,4,5-tetrayl group, pyridine-2,3,4,6-tetrayl group, monofluoropyridine-2,3,4,6-tetrayl group, pyridine-2,3,5,6-tetrayl group, monofluoropyridine-2,3,5,6-tetrayl group, pyrimidine-2,4,5,6-triyl group, dibenzofuran-tetrayl group, dibenzothiophene-tetrayl group, and 9-phenylcarbazole-tetrayl group. In formulas (1) to (3), R 101 ~R 102 , R 201 ~R 203 , R 301 ~R 306 are preferably each independently a group represented by the following (i) or (ii) since they can suppress the formation of a metal film on the film surface and have excellent adhesion to the organic film.

[0029] (i) a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a phenanthryl group, a fluoranthenyl group, a triphenylenyl group, an anthryl group, a pyrenyl group, a pyridyl group, an indolyl group, a carbazolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, an adamantyl group, or a group represented by any of the formulas (4-1) to (4-7); (ii) The group represented by (i) is substituted with one or more groups selected from the group consisting of a methyl group, an ethyl group, a methoxy group, an ethoxy group, a trifluoromethyl group, a trifluoromethoxy group, a perfluoroalkyl group having 2 to 10 carbon atoms, a perfluoroalkoxy group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group which may be substituted with a fluorine atom, a tolyl group which may be substituted with a fluorine atom, a biphenylyl group which may be substituted with a fluorine atom, a naphthyl group which may be substituted with a fluorine atom, a phenanthryl group which may be substituted with a fluorine atom, a pyridyl group which may be substituted with a fluorine atom, a carbazolyl group which may be substituted with a fluorine atom, a dibenzothienyl group which may be substituted with a fluorine atom, and a dibenzofuranyl group which may be substituted with a fluorine atom. In formulas (1) to (3), R 101 ~R 102 , R 201 ~R 203 , R 301 ~R 306 are more preferably each independently a group represented by the following (i') or (ii') since they can suppress the formation of a metal film on the film surface and have excellent adhesion to the organic film.

[0030] (i') a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a phenanthryl group, a triphenylenyl group, a pyridyl group, a carbazolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, an adamantyl group, or a group represented by any of the formulas (4-1) to (4-7); (ii') The group represented by (i') is substituted with one or more groups selected from the group consisting of a methyl group, a trifluoromethyl group, a perfluoroalkyl group having 2 to 10 carbon atoms, a perfluoroalkoxy group having 2 to 10 carbon atoms, a fluorine atom, a perfluorophenyl group, a perfluorotolyl group, and a perfluoropyridyl group. In formulas (1) to (3), R 101 ~R 102 , R 201 ~R 203 , R 301~R 306 can suppress the formation of a metal film on the film surface and has excellent adhesion to an organic film, and therefore, More preferably, the alkyl group is a phenyl group, a methylphenyl group, a dimethylphenyl group, a monofluorophenyl group, a difluorophenyl group, a trifluorophenyl group, a tetrafluorophenyl group, a perfluorophenyl group, a trifluoromethylphenyl group, a bis(trifluoromethyl)phenyl group, a biphenylyl group, a perfluorobiphenyl group, a terphenylyl group, a naphthyl group, a perfluoronaphthyl group, a 9,9-dimethylfluorenyl group, a spirobifluorenyl group, a phenanthryl group, a triphenylenyl group, a pyridyl group, a monofluoropyridyl group, a difluoropyridyl group, a trifluoropyridyl group, a perfluoropyridyl group, a 9-phenylcarbazolyl group, a 9-perfluorophenylcarbazolyl group, a 9-perfluorotolylcarbazolyl group, a 9-perfluoropyridylcarbazolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, an adamantyl group, or a group represented by any of the formulae (4-1) to (4-7). In formulas (1) to (3), L 101 ~L 103 , L 201 ~L 206 , L 301 ~L 309 are preferably each independently a group represented by any one of the following (iii) to (v), since they can suppress the formation of a metal film on the film surface and have excellent adhesion to the organic film.

[0031] (iii) a phenylene group, a biphenylylene group, a terphenylene group, a naphthylene group, a pyridylene group, or a fluorenylene group, (iv) the group represented by (iii) is a group substituted with one or more groups selected from the group consisting of a methyl group, an ethyl group, a methoxy group, an ethoxy group, a trifluoromethyl group, a trifluoromethoxy group, a perfluoroalkyl group having 2 to 10 carbon atoms, a perfluoroalkoxy group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group which may be substituted with a fluorine atom, a tolyl group which may be substituted with a fluorine atom, a biphenylyl group which may be substituted with a fluorine atom, a naphthyl group which may be substituted with a fluorine atom, a phenanthryl group which may be substituted with a fluorine atom, a pyridyl group which may be substituted with a fluorine atom, a carbazolyl group which may be substituted with a fluorine atom, a dibenzothienyl group which may be substituted with a fluorine atom, and a dibenzofuranyl group which may be substituted with a fluorine atom, or (v) A single bond. In formulas (1) to (3), L 101 ~L 103 , L 201 ~L 206 , L 301 ~L 309 are more preferably each independently a group represented by any one of the following (iii') to (v') because they can suppress the formation of a metal film on the film surface and have excellent adhesion to the organic film.

[0032] (iii') a phenylene group, a naphthylene group, or a pyridylene group, (iv') the group represented by (iii') is substituted with one or more groups selected from the group consisting of a methyl group, a trifluoromethyl group, a trifluoromethoxy group, a perfluoroalkyl group having 2 to 10 carbon atoms, a perfluoroalkoxy group having 2 to 10 carbon atoms, and a fluorine atom, or (v') Single bond. In formulas (1) to (3), L 101 ~L 103 , L 201 ~L 206 , L 301 ~L 309 can suppress the formation of a metal film on the film surface and has excellent adhesion to an organic film, and therefore, More preferably, it is a phenylene group, a monofluorophenylene group, a difluorophenylene group, a trifluorophenylene group, a perfluorophenylene group, a trifluoromethylphenylene group, a naphthylene group, a perfluoronaphthylene group, a pyridylene group, a monofluoropyridylene group, a difluoropyridylene group, a perfluoropyridylene group, or a single bond. In the formulas (1) to (3), X is preferably each independently a group represented by the following (vi) or (vii) because this can suppress the formation of a metal film on the film surface and provides excellent adhesion to an organic film.

[0033] (vi) A phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a fluorenylene group, a spirobifluorenylene group, a benzofluorenylene group, a phenanthrene group, a fluoranthenylene group, a triphenylenylene group, an anthracenediyl group, a pyridylene group, a pyrimidinediyl group, a triazinediyl group, a carbazolediyl group, a benzofurandiyl group, a benzothiophenediyl group, a dibenzofurandiyl group, an adamantanediyl group, a phenyl group, a methylene group, a silanediyl group, a cyclohexylene group, a phenyltriyl group, a biphenyltriyl group, a terphenyltriyl group, a naphthyltriyl group, a fluorenetriyl group, a spirobifluorenetriyl group, a benzofluorenetriyl group, a phenanthrenetriyl group, a fluoranthentriyl group, a triphenylenetriyl group, an anthracenetriyl group, a pyrenetriyl group, a pyridinetriyl group, a pyrimidinetriyl group, a triphenylene ... an azinetriyl group, a carbazoletriyl group, a benzofurantriyl group, a benzothiophenetriyl group, a dibenzofurantriyl group, an adamantanetriyl group, a methanetriyl group, a silanetriyl group, a cyclohexanetriyl group, a phenyltetrayl group, a biphenyltetrayl group, a terphenyltetrayl group, a naphthyltetrayl group, a fluorenetetrayl group, a spirobifluorenetetrayl group, a benzofluorenetetrayl group, a phenanthrenetetrayl group, a fluoranthenetetrayl group, a triphenylenetetrayl group, an anthracenetetrayl group, a pyrenetetrayl group, a pyridinetetrayl group, a pyrimidinetetrayl group, a carbazoletetrayl group, a benzofurantetrayl group, a benzothiophenetetrayl group, a dibenzofurantetrayl group, an adamantanetetrayl group, a methanetetrayl group, a silanetetrayl group, or a cyclohexanetetrayl group; (vii) The group represented by (vi) is substituted with one or more groups selected from the group consisting of a methyl group, an ethyl group, a methoxy group, an ethoxy group, a trifluoromethyl group, a trifluoromethoxy group, a perfluoroalkyl group having 2 to 10 carbon atoms, a perfluoroalkoxy group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group which may be substituted with a fluorine atom, a tolyl group which may be substituted with a fluorine atom, a biphenylyl group which may be substituted with a fluorine atom, a naphthyl group which may be substituted with a fluorine atom, a phenanthryl group which may be substituted with a fluorine atom, a pyridyl group which may be substituted with a fluorine atom, a carbazolyl group which may be substituted with a fluorine atom, a dibenzothienyl group which may be substituted with a fluorine atom, and a dibenzofuranyl group which may be substituted with a fluorine atom. In the formulas (1) to (3), X is more preferably each independently a group represented by the following (vi') or (vii') because this can suppress the formation of a metal film on the film surface and has excellent adhesion to the organic film.

[0034] (vi') a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a fluorenylene group, a spirobifluorenylene group, a phenanthrene group, a triphenylenylene group, a pyridylene group, a pyrimidinediyl group, a triazinediyl group, a carbazolediyl group, a dibenzofurandiyl group, an adamantanediyl group, a methylene group, a silanediyl group, a cyclohexylene group, a phenyltriyl group, a biphenyltriyl group, a naphthyltriyl group, a spiro bifluorenetriyl group, pyridinetriyl group, pyrimidinetriyl group, triazinetriyl group, adamantanetriyl group, methanetriyl group, silanetriyl group, cyclohexanetriyl group, phenyltetrayl group, biphenyltetrayl group, naphthyltetrayl group, spirobifluorenetetrayl group, pyridinetetrayl group, pyrimidinetetrayl group, methanetetrayl group, silanetetrayl group, or cyclohexanetetrayl group; (vii') The group represented by (vi') is substituted with one or more groups selected from the group consisting of a methyl group, a trifluoromethyl group, a perfluoroalkyl group having 2 to 10 carbon atoms, a perfluoroalkoxy group having 2 to 10 carbon atoms, a fluorine atom, a perfluorophenyl group, a perfluorotolyl group, and a perfluoropyridyl group. In the formulas (1) to (3), X can suppress the formation of a metal film on the film surface and has excellent adhesion to an organic film, and therefore each X is independently Phenylene group, methylphenylene group, dimethylphenylene group, monofluorophenylene group, difluorophenylene group, trifluorophenylene group, perfluorophenylene group, trifluoromethylphenylene group, bis(trifluoromethyl)phenylene group, naphthylene group, perfluoronaphthylene group, biphenylene group, methylbiphenylene group, dimethylbiphenylene group, trifluoromethylbiphenylene group, bis(trifluoromethyl)biphenylene group, fluorobiphenylene group, difluorobiphenylene group, trifluoromethylbiphenylene group, Fluorobiphenylene group, tetrafluorobiphenylene group, perfluorobiphenylene group, terphenylylene group, 9,9-dimethylfluorenylene group, spirobifluorenylene group, phenanthrene group, triphenylenylene group, pyridylene group, monofluoropyridylene group, difluoropyridylene group, perfluoropyridylene group, pyrimidinediyl group, 9-phenylcarbazolediyl group, 9-perfluorophenylcarbazolediyl group, 9-perfluorotolylcarbazolediyl group, 9-perfluoropyridylcarbazolediyl group, bazolediyl group, dibenzofurandiyl group, adamantanediyl group, methylene group, diphenylsilanediyl group, cyclohexylene group, benzenetriyl group, methylphenyltriyl group, dimethylphenyltriyl group, trimethylphenyltriyl group, fluorophenyltriyl group, difluorophenyltriyl group, trifluorophenyltriyl group, trifluoromethylphenyltriyl group, bis(trifluoromethyl)phenyltriyl group, tristrifluoromethylphenyltriyl group, biphenyltriyl group, a naphthyltriyl group, a spirobifluorenetriyl group, a pyridinetriyl group, a pyrimidinetriyl group, a triazinetriyl group, an adamantanetriyl group, a methanetriyl group, a phenylsilanetriyl group, a cyclohexanetriyl group, a benzenetetrayl group, a biphenyltetrayl group, a naphthyltetrayl group, a spirobifluorenetetrayl group, a pyridinetetrayl group, a pyrimidinetetrayl group, a methanetetrayl group, a silanetetrayl group, or a cyclohexanetetrayl group is more preferred. In the formulas (1) to (3), it is preferable that the molecule has two or more substituents represented by formula (5), since this can suppress the formation of a metal film on the film surface and provides excellent adhesion to an organic film. In formulas (1) to (3), Ar 101 , Ar 201 , Ar 301 The following formulae (6-1) to (6-22) are each independently preferred since they can suppress the formation of a metal film on the film surface and have excellent adhesion to an organic film.

[0035] [ka]

[0036] [ka]

[0037] [ka]

[0038] In formulas (6-1) to (6-22), R 501 ~R 549 are each independently Hydrogen atom, deuterium atom, fluorine atom, bromine atom, chlorine atom, a linear or branched aliphatic hydrocarbon group having 1 to 4 carbon atoms which may be substituted with a fluorine atom; a linear or branched alkoxy group having 1 to 4 carbon atoms which may be substituted with a fluorine atom; an optionally substituted cyclic aliphatic hydrocarbon group having 5 to 20 carbon atoms; an optionally substituted cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms; an aromatic hydrocarbon group having 6 to 20 carbon atoms which may be substituted, or It represents an optionally substituted heteroaromatic group having 3 to 20 carbon atoms.

[0039] R 501 ~R 546are each independently It is preferably a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, a trifluoromethyl group, a methoxy group, a phenyl group, or a naphthyl group. In formulas (6-1) to (6-22), L 601 ~L 630 are each independently It represents a straight-chain or branched divalent aliphatic hydrocarbon group having 1 to 4 carbon atoms, an oxygen atom, a sulfur atom, or a single bond.

[0040] L 601 ~L 630 are preferably each independently an oxygen atom or a single bond.

[0041] L 701 ~L 730 are each independently It represents a straight-chain or branched divalent aliphatic hydrocarbon group having 1 to 4 carbon atoms, an oxygen atom, a sulfur atom, or a single bond.

[0042] L 701 ~L 730 are preferably each independently a methylene group, an ethylene group, a propylene group, or a single bond.

[0043] In formulas (6-1) to (6-22), p and q each independently represent an integer of 0 to 11.

[0044] It is preferable that p and q each independently represent an integer of 0 to 9.

[0045] * represents a bond Examples of the amine compound according to one embodiment of the present disclosure include compounds (A1) to (A110) below, but the present disclosure is not limited to these compounds.

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[0066] [Metal patterning materials] The metal patterning material according to one embodiment of the present disclosure is a material that contains an amine compound represented by the formula (1), (2) or (3) and can form a thin film, and has the effect of suppressing the formation of a thin metal film on the film surface. In addition, the metal patterning material may contain any other organic molecular material, polymer, etc., within a range that can suppress the formation of a metal film on the film surface. The type of metal material to be patterned is not particularly limited, but is preferably an alkali metal, an alkaline earth metal, a transition metal, or a metal of Group 13 of the periodic table, and examples thereof include lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, gold, silver, platinum, copper, iron, palladium, molybdenum, manganese, titanium, cobalt, nickel, tungsten, tin, and chromium, as well as alloys and salts containing one or more of these metals. Examples of alloys include magnesium-silver alloys, magnesium-indium alloys, magnesium-aluminum alloys, indium-silver alloys, lithium-aluminum alloys, lithium-magnesium alloys, lithium-indium alloys, calcium-aluminum alloys, and the like, and an example of a salt is lithium fluoride. [Thin films for metal patterning] A thin film for metal patterning according to one embodiment of the present disclosure contains an amine compound represented by formula (1), (2) or (3) and is capable of patterning a metal film or a metal laminate film.

[0067] The metal film or metal laminate film contains one or more metals selected from the group consisting of lithium, ytterbium, silver, aluminum, copper, titanium, chromium, and magnesium, or an alloy containing one or more of these metals. The alloy contained in the metal film or metal laminate film is preferably a magnesium alloy or a silver alloy, and more preferably an alloy of magnesium and silver.

[0068] In one embodiment of the present disclosure, it is more preferable that the water contact angles of the thin film for metal patterning are, in order, 90° or more, 91° or more, 92° or more, 93° or more, 94° or more, 95° or more, 96° or more, 97° or more, 98° or more, 99° or more, and 100° or more. [Organic electroluminescence element] An organic electroluminescence element according to one aspect of the present disclosure is an organic electroluminescence element including a cathode, The cathode contains one or more metals selected from the group consisting of lithium, ytterbium, silver, aluminum, and magnesium, or an alloy containing one or more of these metals, and is patterned with a metal patterning material, which contains an amine compound represented by formula (1), (2), or (3). The alloy contained in the cathode is preferably a magnesium alloy or a silver alloy, and more preferably an alloy of magnesium and silver.

[0069] For the organic electroluminescence element, the metal patterning material used for patterning is the same as the above-mentioned metal patterning material, which contains the amine compound represented by the formula (1), (2) or (3). [Metal pattern formation method] A method for forming a metal pattern according to one embodiment of the present disclosure includes forming an organic material pattern containing an amine compound (metal patterning material) represented by formula (1), (2) or (3); and applying a metal material to a region where the organic material pattern is formed and a region where the organic material pattern is not formed, thereby forming a metal pattern in the region where the organic material pattern is not formed.

[0070] The metal patterning material is used by forming a film in the area where it is desired to suppress adhesion of the metal material. The area where it is desired to suppress adhesion of the metal material corresponds to the area where the organic material pattern is formed. Areas other than the area where it is desired to suppress adhesion of the metal material correspond to the area where the organic material pattern is not formed. The area where the organic material pattern is not formed is the area where adhesion of the metal material is promoted and is the area where it is desired to form the metal pattern.

[0071] The method for forming the organic material pattern (film formation method) is not particularly limited, and known methods such as vacuum deposition, spin coating, casting, dip coating, die coating, bar code, offset, spray coating, inkjet, screen, offset, flexography, gravure, and microcontact can be applied. After film formation, the film may be annealed in a temperature environment higher than room temperature. There is also no particular limit to the film thickness of the organic material pattern.

[0072] Furthermore, other organic molecular materials, polymers, etc. may be added to the metal patterning material as long as the formation of a metal film on the film surface can be suppressed.

[0073] The base on which the organic material pattern is formed may be either metallic or non-metallic, and examples of the base include organic films, metallic films, oxide films, inorganic films, etc. There are no particular limitations on the material of the substrate, and glass, plastic, metal, ceramic, and any other material can be used.

[0074] When the base on which the organic material pattern is formed is an organic film, the organic film may be, for example, a tris(8-quinolinolato)aluminum derivative, an imidazole derivative, a benzimidazole derivative, a triazine derivative, a pyrimidine derivative, a pyridine derivative, a pyrazine derivative, a quinoline derivative, a quinoxaline derivative, an oxadiazole derivative, a phosphole derivative, a silole derivative, or a phosphine oxide derivative.

[0075] The type of metal material used to form a metal pattern using a metal patterning material is not particularly limited, but may be any of the following: Alkali metals, alkaline earth metals, transition metals, and metals of Group 13 of the Periodic Table are preferred; More preferred are lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, gold, silver, platinum, copper, iron, palladium, molybdenum, manganese, titanium, cobalt, nickel, tungsten, tin, chromium, and alloys containing one or more selected from the group consisting of these metals.

[0076] Examples of such alloys include magnesium-silver alloys, magnesium-indium alloys, magnesium-aluminum alloys, indium-silver alloys, lithium-aluminum alloys, lithium-magnesium alloys, lithium-indium alloys, and calcium-aluminum alloys.

[0077] The method for forming the metal pattern is not particularly limited, and examples thereof include dry processes such as vacuum deposition and sputtering, and inkjet methods using metal nanoink, etc. Furthermore, there is no particular limit to the film thickness of the metal pattern.

[0078] By applying a metal material to the region where the organic material pattern is formed and the region where the organic material pattern is not formed, a film containing the metal material is instantaneously formed in both regions. However, since the adhesion of metal is suppressed in the region where the organic material pattern is formed, the metal pattern is naturally formed only in the region where the organic material pattern is not formed.

[0079] More specific examples of the method for forming the metal pattern include the following methods 1) and 2). 1) The above-mentioned metal patterning material is evaporated into a desired pattern using a metal mask or the like. 2) Then, metal is evaporated to form electrodes only on the areas where the metal patterning material is not deposited, i.e., negative metal electrodes are formed with respect to the deposition pattern of the metal patterning material.

[0080] The area and line width of the patterned metal electrode can be adjusted as desired by changing the patterning shape of the metal patterning material.

[0081] A protective film may be provided on the patterned film obtained by patterning the metal. The protective film may be, for example, an organic film, an oxide film, an inorganic film, or the like, and is not particularly limited.

[0082] When the protective film is an organic film, examples of the organic film that can be used 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 (particularly thiophene oligomers), porphyrin compounds, aromatic tertiary amine compounds, carbazole compounds, styrylamine compounds, triazine derivatives, and pyrimidine derivatives.

[0083] When the protective film is an inorganic film, the inorganic film may be, for example, silicon nitride, silicon oxide, or the like.

[0084] According to the metal patterning material and the metal pattern forming method according to one embodiment of the present disclosure, it is possible to pattern metal electrodes of solar cells, photosensors, image sensors, organic electroluminescence (EL) elements, organic solar cells, organic sensors, organic transistors, and the like, and to form metal wiring on a circuit board. [Electronic equipment] The electronic device according to one embodiment of the present disclosure includes an amine compound (metal patterning material) represented by the above-mentioned formula (1), (2) or (3). As described above, when forming a metal pattern, an organic material pattern containing the metal patterning material is formed, so that the organic material pattern is formed together with the metal pattern. Therefore, the electronic device according to one embodiment of the present disclosure includes an organic material pattern containing the metal patterning material together with the metal pattern.

[0085] Examples of electronic devices include solar cells, photosensors, image sensors, organic EL elements, organic solar cells, organic sensors, and organic transistors. These electronic devices include patterned metal electrodes, metal wiring on a circuit board, and the like. In other words, if the electronic device includes patterned metal electrodes or metal wiring on a circuit board, the electronic device according to this embodiment can be obtained by using the above-mentioned method for forming a metal pattern. Such electronic devices have a highly accurate metal pattern. EXAMPLES

[0086] The present invention will be described in more detail below based on examples, but the present invention should not be construed as being limited to these examples in any way.

[0087] NMR measurements were carried out using the following equipment. [NMR measurement] Measuring device: JEOL JNM-ECZ400S [Transmittance measurement] Metal adhesion can be evaluated by measuring the transmittance, and the transmittance decreases as metal adheres to the surface. Also, the transmittance decreases in correlation with the amount of metal adhered to the surface.

[0088] The transmittance measurements were carried out using the following equipment.

[0089] Measurement equipment: JASCO V-750 Measurement range: 550~800nm [Synthesis of compound (A1) and evaluation of metal adhesion] Example 1-1 Synthesis of intermediate (AA-101)

[0090] [ka]

[0091] Under a nitrogen atmosphere, a solution of phenyl-1-naphthylamine (3.0 mmol) in sodium hydroxide (100 ml) was added to a solution of cyanuric chloride (3.0 mmol) in THF, and the mixture was stirred at 0°C for 4 hours. After the reaction was completed, water (300 mL) was added and the mixture was stirred at room temperature for 30 minutes. The precipitated solid was filtered and washed with acetone. After drying at 50°C, the desired intermediate (AA-101) was obtained (yield 92%).

[0092] The compounds were identified by FDMS measurement.

[0093] FDMS:366.04 Example 1-2 Synthesis of A1

[0094] [ka]

[0095] Under a nitrogen atmosphere, the intermediate (AA-101) (3.0 mmol) was dissolved in THF (100 ml), and 2,2,3,3,4,4,5,5-octafluoro-1-pentanol and tripotassium phosphate (7.0 mmol) were added, followed by stirring at 80°C for 5 hours. Water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethanol. The precipitated solid was filtered to obtain the target compound A1 (yield 70%). The compound was identified by FDMS measurement.

[0096] FDMS:758.12 Example 1-2' (Evaluation of metal adhesion of compound (A1)) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 1 Pa or less. Compound (A1) was deposited at a deposition rate of 0.2 nm / sec to form a 100 nm film on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to form a 2 nm film, followed by silver deposition at a deposition rate of 0.1 nm / sec to form a 20 nm film. No ytterbium or silver was deposited on the area on which compound (A1) was deposited, forming a 20 mm x 10 mm transparent area.

[0097] Example 1-2″ (Evaluation of adhesion of compound (A1) to CVD film) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to less than 1 Pa. Compound (A1) was deposited at a deposition rate of 0.2 nm / sec to form a 100 nm film on a glass substrate with a metal mask having an opening of 20 mm x 10 mm. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to form a 2 nm film, followed by silver deposition at a deposition rate of 0.1 nm / sec to form a 20 nm film. Further, CVD deposition (SiN) was performed at 11 Ω / sec, and after one day, it was visually confirmed that there was no peeling in the area where compound (A1) was deposited. [Synthesis of compound (A11) and evaluation of metal adhesion] Example 2-1 Synthesis of intermediate (AA-201)

[0098] [ka]

[0099] Under a nitrogen atmosphere, 2,4,6-trichloropyrimidine (3.0 mmol) was mixed with 1H,1H,7H-decafluoro-1-heptanol (9.0 mmol), THF (100 ml), and triethylamine, and the mixture was stirred at 80°C for 16 hours. Water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was purified by column chromatography (silica gel, hexane:ethyl acetate = 5:1) to obtain AA-201 (yield 70%). The compound was identified by FDMS measurement. FDMS: 773.98 Example 2-2 Synthesis of A11

[0100] [ka]

[0101] Under a nitrogen atmosphere, the intermediate (AA-201) (3.0 mmol) was dissolved in THF (100 ml), 2-adamantanamine, and potassium hydroxide, and stirred at 80°C for 12 hours. Water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethyl acetate and ethanol. The precipitated solid was filtered to obtain the target product A11 (yield 70%). The compounds were identified by FDMS measurement.

[0102] FDMS:1627.15 Example 2-2' (Evaluation of Metal Adhesion of Compound (A11)) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 1 Pa or less. Compound (A11) was deposited at a deposition rate of 0.2 nm / sec to form a 100 nm film on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to form a 2 nm film, and then silver was deposited at a deposition rate of 0.1 nm / sec to form a 20 nm film. No ytterbium or silver was deposited on the area on which compound (A11) was deposited, and a 20 mm x 10 mm transparent area was formed.

[0103] Example 2-2″ (Evaluation of Adhesion of Compound (A11) to CVD Film) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 0.02 Pa or less. Compound (A11) was deposited at a deposition rate of 0.2 nm / sec to a thickness of 100 nm on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. Further CVD deposition was performed, and after one day, it was visually confirmed that there was no peeling in the area on which compound (A11) was deposited. [Synthesis of compound (A18) and evaluation of metal adhesion] Example 3-1 Synthesis of intermediate (AA-301)

[0104] [ka]

[0105] Under a nitrogen atmosphere, a sodium hydroxide solution (100 ml) of N-(4-(dibenzo[b,d]furan-4-yl)phenyl)pyridin-3-amine (3.0 mmol) was added to a THF solution of 2,4,6-trichloropyrimidine (3.0 mmol) and stirred at 0°C for 4 hours. After the reaction was completed, water (300 mL) was added and stirred at room temperature for 30 minutes. The precipitated solid was filtered and washed with acetone. After drying at 50°C, the desired intermediate (AA-301) was obtained (yield 89%).

[0106] The compounds were identified by FDMS measurement.

[0107] FDMS: 482.07 Example 3-2 Synthesis of A18

[0108] [ka]

[0109] Under a nitrogen atmosphere, the intermediate (AA-301) (3.0 mmol) was dissolved in THF (100 ml), and 1H,1H,11H-eicosafluoro-1-undecanol and tripotassium phosphate (7.0 mmol) were added, followed by stirring at 80°C for 5 hours. Water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethanol. The precipitated solid was filtered to obtain the target compound A18 (yield 70%). The compound was identified by FDMS measurement.

[0110] FDMS:1474.11 Example 3-2' (Evaluation of metal adhesion of compound (A18)) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 1 Pa or less. Compound (A18) was deposited at a deposition rate of 0.2 nm / sec to form a 100 nm film on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to form a 2 nm film, followed by silver deposition at a deposition rate of 0.1 nm / sec to form a 20 nm film. No ytterbium or silver was deposited on the area on which compound (A18) was deposited, forming a 20 mm x 10 mm transparent area.

[0111] Example 3-2″ (Evaluation of adhesion of compound (A18) to CVD film) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The chamber was evacuated with a vacuum pump until the pressure in the chamber was reduced to less than 1 Pa. Compound (A18) was deposited at a deposition rate of 0.2 nm / sec to a thickness of 100 nm on a glass substrate with a metal mask having an opening of 20 mm x 10 mm. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. Further, CVD deposition (SiN) was performed at 11 Ω / sec, and after one day, it was visually confirmed that there was no peeling in the area where compound (A18) was deposited. [Synthesis of compound (A19) and evaluation of metal adhesion] Example 4-1 Synthesis of intermediate (AA-401)

[0112] [ka]

[0113] Under a nitrogen atmosphere, a sodium hydroxide solution (100 ml) of N-(4-(dibenzo[b,d]furan-4-yl)phenyl)pyridin-3-amine (3.0 mmol) was added to a THF solution of 2,4,6-trichloro-5-(trifluoromethyl)pyrimidine (3.0 mmol) and stirred at 0°C for 4 hours. After the reaction was completed, water (300 mL) was added and stirred at room temperature for 30 minutes. The precipitated solid was filtered and washed with acetone. After drying at 50°C, the target intermediate (AA-401) was obtained (yield 78%).

[0114] The compounds were identified by FDMS measurement.

[0115] FDMS:724.01 Example 4-2 Synthesis of A19

[0116] [ka]

[0117] Under a nitrogen atmosphere, the intermediate (AA-401) (3.0 mmol) was dissolved in THF (100 ml), and 1H,1H,11H-eicosafluoro-1-undecanol and tripotassium phosphate (7.0 mmol) were added, followed by stirring at 80°C for 5 hours. Water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethanol. The precipitated solid was filtered to obtain the target compound A19 (yield 73%). The compound was identified by FDMS measurement.

[0118] FDMS:1648.06 Example 4-2' (Evaluation of metal adhesion of compound (A19)) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 1 Pa or less. Compound (A19) was deposited at a deposition rate of 0.2 nm / sec to form a 100 nm film on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to form a 2 nm film, followed by silver deposition at a deposition rate of 0.1 nm / sec to form a 20 nm film. No ytterbium or silver was deposited on the area on which compound (A19) was deposited, forming a 20 mm x 10 mm transparent area.

[0119] Example 4-2″ (Evaluation of adhesion of compound (A19) to CVD film) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4The chamber was evacuated with a vacuum pump until the pressure in the chamber was reduced to less than 1 Pa. Compound (A19) was deposited at a deposition rate of 0.2 nm / sec to a thickness of 100 nm on a glass substrate with a metal mask having an opening of 20 mm x 10 mm. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. Further, CVD deposition (SiN) was performed at 11 Ω / sec, and after one day, it was visually confirmed that there was no peeling in the area where compound (A19) was deposited. [Synthesis of compound (A23) and evaluation of metal adhesion] Example 5-1 Synthesis of intermediate (AA-501)

[0120] [ka]

[0121] Under a nitrogen atmosphere, (3s,5s,7s)-adamantan-1-amine (3.0 mmol) was dissolved in THF (50 ml), sodium hydride (7.0 mmol) was added, and the mixture was stirred for 30 minutes. The mixture was then heated to 70°C, and 2,4,6-trichloropyrimidine (7.0 mmol) was added. After the reaction was completed, water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethyl acetate. The precipitated crystals were filtered to obtain the target product AA-501 (yield 62%). The compounds were identified by FDMS measurement.

[0122] FDMS:443.02 Example 5-2 Synthesis of A23

[0123] [ka]

[0124] Under a nitrogen atmosphere, the intermediate (AA-501) (3.0 mmol) was dissolved in THF (50 ml), and tripotassium phosphate (7.0 mmol) and 1H,1H,7H-dodecafluoro-1-heptanol (7.0 mmol) were added and stirred for 30 minutes. The temperature was then raised to 70°C and the mixture was stirred for 6 hours. After the reaction was completed, water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethanol and ethyl acetate. The precipitated crystals were filtered to obtain the target product A23 (yield 72%). The compounds were identified by FDMS measurement.

[0125] FDMS:1627.15 Example 5-3' (Evaluation of metal adhesion of compound (A23)) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The vacuum pump was used to evacuate the chamber until the pressure reached 1 Pa or less. Compound (A23) was deposited at a deposition rate of 0.2 nm / sec to form a 100 nm film on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to form a 2 nm film, and then silver was deposited at a deposition rate of 0.1 nm / sec to form a 20 nm film. No ytterbium or silver was deposited on the area on which compound (A23) was deposited, and a 20 mm x 10 mm transparent area was formed.

[0126] Example 5-3″ (Evaluation of adhesion of compound (A23) to CVD film) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 0.02 Pa or less. Compound (A23) was deposited at a deposition rate of 0.2 nm / sec to a thickness of 100 nm on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. Further CVD deposition was performed, and after one day, it was visually confirmed that there was no peeling in the area on which compound (A23) was deposited. [Synthesis of compound (A50) and evaluation of metal adhesion] Example 6-1 Synthesis of intermediate (AA-601)

[0127] [ka]

[0128] Under a nitrogen atmosphere, 9H-carbazole (3.0 mmol) was dissolved in THF (50 ml), sodium hydride (7.0 mmol) was added, and the mixture was stirred for 30 minutes. The mixture was then heated to 70°C and perfluoropyridine (7.0 mmol) was added. After the reaction was completed, water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethyl acetate. The precipitated crystals were filtered to obtain the target product AA-601 (yield 68%). The compounds were identified by FDMS measurement.

[0129] FDMS: 348.00 Example 6-2 Synthesis of A50

[0130] [ka]

[0131] Under a nitrogen atmosphere, the intermediate (AA-601) (3.0 mmol) was dissolved in THF (50 ml), sodium hydride (7.0 mmol) and 1H,1H,9H-hexadecafluoro-1-nonanol (7.0 mmol) were added, and the mixture was stirred for 30 minutes. The temperature was then raised to 70°C and the mixture was stirred for 6 hours. After the reaction was completed, water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethanol and ethyl acetate. The precipitated crystals were filtered to obtain the target product A50 (yield 72%). The compounds were identified by FDMS measurement.

[0132] FDMS:1627.15 Example 6-3' (Evaluation of metal adhesion of compound (A50)) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 1 Pa or less. Compound (A50) was deposited at a deposition rate of 0.2 nm / sec to form a 100 nm film on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to form a 2 nm film, and then silver was deposited at a deposition rate of 0.1 nm / sec to form a 20 nm film. No ytterbium or silver was deposited on the area on which compound (A50) was deposited, and a 20 mm x 10 mm transparent area was formed.

[0133] Example 6-3″ (Evaluation of adhesion of compound (A50) to CVD film) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 0.02 Pa or less. Compound (A50) was deposited at a deposition rate of 0.2 nm / sec to a thickness of 100 nm on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. Further CVD deposition was performed, and after one day, it was visually confirmed that there was no peeling in the area on which compound (A50) was deposited. [Synthesis of compound (A51) and evaluation of metal adhesion] Example 7-1 Synthesis of intermediate (AA-701)

[0134] [ka]

[0135] Under a nitrogen atmosphere, perfluorotoluene (9.0 mmol), DMSO (100 ml), and tripotassium phosphate (10 mmol) were added to 1,4-Phenylenediamine (3.0 mmol) and stirred at 100°C for 20 hours. After cooling to room temperature, water (300 mL) was added and stirred at room temperature for 30 minutes. The precipitated solid was filtered and washed with methanol. After drying at 50°C, the desired intermediate (AA-701) was obtained (yield 86%).

[0136] The compounds were identified by FDMS measurement.

[0137] FDMS:540.03 Example 7-2 Synthesis of intermediate (AA-702)

[0138] [ka]

[0139] Under a nitrogen atmosphere, the intermediate (AA-701) (3.0 mmol) was dissolved in THF (50 ml), sodium hydride (7.0 mmol) was added, and the mixture was stirred for 30 minutes. The mixture was then heated to 70°C, and cyanuric chloride (7.0 mmol) was added. After the reaction was completed, water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethyl acetate. The precipitated crystals were filtered to obtain the target product, AA-702 (yield 60%). The compounds were identified by FDMS measurement.

[0140] FDMS:833.91 Example 7-3 Synthesis of A51

[0141] [ka]

[0142] Under a nitrogen atmosphere, the intermediate (AA-702) (3.0 mmol) was dissolved in THF (50 ml), and tripotassium phosphate (7.0 mmol) and 1H,1H,7H-decafluoro-1-heptanol (7.0 mmol) were added, stirred for 30 minutes, and then heated to 70°C and stirred for 6 hours. After the reaction was completed, water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethanol and ethyl acetate. The precipitated crystals were filtered to obtain the target product A51 (yield 70%). The compounds were identified by FDMS measurement.

[0143] FDMS:2018.03 Example 7-3' (Evaluation of metal adhesion of compound (A51)) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 1 Pa or less. Compound (A51) was deposited at a deposition rate of 0.2 nm / sec to form a 100 nm film on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to form a 2 nm film, and then silver was deposited at a deposition rate of 0.1 nm / sec to form a 20 nm film. No ytterbium or silver was deposited on the area on which compound (A51) was deposited, and a 20 mm x 10 mm transparent area was formed.

[0144] Example 7-3″ (Evaluation of adhesion of compound (A51) to CVD film) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 0.02 Pa or less. Compound (A51) was deposited at a deposition rate of 0.2 nm / sec to a thickness of 100 nm on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. Further CVD deposition was performed, and after one day, it was visually confirmed that there was no peeling in the area on which compound (A51) was deposited. [Synthesis of compound (A53) and evaluation of metal adhesion] Example 8-1 Synthesis of intermediate (AA-801)

[0145] [ka]

[0146] Under a nitrogen atmosphere, perfluoronaphthalene (9.0 mmol), DMSO (100 ml), and tripotassium phosphate (10 mmol) were added to 1,4-Phenylenediamine (3.0 mmol) and stirred at 100°C for 20 hours. After cooling to room temperature, water (300 mL) was added and stirred at room temperature for 30 minutes. The precipitated solid was filtered and washed with methanol. After drying at 50°C, the desired intermediate (AA-801) was obtained (yield 90%).

[0147] The compounds were identified by FDMS measurement.

[0148] FDMS:736.02 Example 8-2 Synthesis of A53

[0149] [ka]

[0150] Under a nitrogen atmosphere, the intermediate (AA-801) (3.0 mmol) was dissolved in THF (50 ml), AA-801 and potassium carbonate were added, and the mixture was stirred at 70°C for 20 hours. Water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethyl acetate and ethanol. The precipitated solid was filtered to obtain the target product A53 (yield 60%). The compounds were identified by FDMS measurement.

[0151] FDMS:2212.03 Example 8-2' (Evaluation of metal adhesion of compound (A53)) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 1 Pa or less. Compound (A53) was deposited at a deposition rate of 0.2 nm / sec to form a 100 nm film on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to form a 2 nm film, and then silver was deposited at a deposition rate of 0.1 nm / sec to form a 20 nm film. No ytterbium or silver was deposited on the area on which compound (A53) was deposited, and a 20 mm x 10 mm transparent area was formed.

[0152] Example 8-2″ (Evaluation of adhesion of compound (A53) to CVD film) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 0.02 Pa or less. Compound (A53) was deposited at a deposition rate of 0.2 nm / sec to a thickness of 100 nm on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. Further CVD deposition was performed, and after one day, it was visually confirmed that there was no peeling in the area on which compound (A53) was deposited. [Synthesis of compound (A54) and evaluation of metal adhesion] Example 9-1 Synthesis of intermediate (AA-901)

[0153] [ka]

[0154] Under a nitrogen atmosphere, 2,3,5,6-tetrafluoro-1,4-phenylenediamine (3.0 mmol) was mixed with pentafluoropyridine (9.0 mmol), DMSO (100 ml), and tripotassium phosphate (10 mmol) and stirred at 100°C for 20 hours. After cooling to room temperature, water (300 mL) was added and stirred at room temperature for 30 minutes. The precipitated solid was filtered and washed with methanol. After drying at 50°C, the target intermediate (AA-901) was obtained (yield 72%).

[0155] The compounds were identified by FDMS measurement.

[0156] FDMS:406.05 Example 9-2 Synthesis of intermediate (AA-902)

[0157] [ka]

[0158] Under a nitrogen atmosphere, the intermediate (AA-901) (3.0 mmol) was dissolved in THF (50 ml), sodium hydride (7.0 mmol) was added, and the mixture was stirred for 30 minutes. The mixture was then heated to 70°C, and 2,4,6-trifluoropyridine (7.0 mmol) was added. After the reaction was completed, water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethyl acetate. The precipitated crystals were filtered to obtain the target product AA-902 (yield 63%). The compounds were identified by FDMS measurement.

[0159] FDM S: 695.94 Example 9-3 Synthesis of A54

[0160] [ka]

[0161] Under a nitrogen atmosphere, the intermediate (AA-902) (3.0 mmol) was dissolved in THF (50 ml), and tripotassium phosphate (7.0 mmol) and 2,2,3,3,4,4,5,5-octafluoro-1-pentanol (7.0 mmol) were added and stirred for 30 minutes. The temperature was then raised to 70°C and the mixture was stirred for 6 hours. After the reaction was completed, water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethanol and ethyl acetate. The precipitated crystals were filtered to obtain the target product A54 (yield 70%). The compounds were identified by FDMS measurement.

[0162] FDMS:1552.05 Example 9-3' (Evaluation of metal adhesion of compound (A54)) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 1 Pa or less. Compound (A54) was deposited at a deposition rate of 0.2 nm / sec to form a 100 nm film on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to form a 2 nm film, and then silver was deposited at a deposition rate of 0.1 nm / sec to form a 20 nm film. No ytterbium or silver was deposited on the area on which compound (A54) was deposited, and a 20 mm x 10 mm transparent area was formed.

[0163] Example 9-3″ (Evaluation of adhesion of compound (A54) to CVD film) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 0.02 Pa or less. Compound (A54) was deposited at a deposition rate of 0.2 nm / sec to a thickness of 100 nm on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. Further CVD deposition was performed, and after one day, it was visually confirmed that there was no peeling in the area on which compound (A54) was deposited. [Synthesis of compound (A61) and evaluation of metal adhesion] Example 10-1 Synthesis of intermediate (AA-1001)

[0164] [ka]

[0165] Under a nitrogen atmosphere, perfluorotoluene (9.0 mmol), DMSO (100 ml), and tripotassium phosphate (10 mmol) were added to 4,4'-diaminooctafluorobiphenyl (3.0 mmol), and the mixture was stirred at 100°C for 20 hours. After cooling to room temperature, water (300 mL) was added and the mixture was stirred at room temperature for 30 minutes. The precipitated solid was filtered and washed with methanol. After drying at 50°C, the target intermediate (AA-1001) was obtained (yield 83%).

[0166] The compounds were identified by FDMS measurement.

[0167] FDMS:759.99 Example 10-2 Synthesis of intermediate (AA-1002)

[0168] [ka]

[0169] Under a nitrogen atmosphere, the intermediate (AA-1001) (3.0 mmol) was dissolved in THF (50 ml), sodium hydride (7.0 mmol) was added, and the mixture was stirred for 30 minutes. The mixture was then heated to 70°C, and cyanuric chloride (7.0 mmol) was added. After the reaction was completed, water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethyl acetate. The precipitated crystals were filtered to obtain the target product, AA-1002 (yield 64%). The compounds were identified by FDMS measurement.

[0170] FDMS: 1053.86 Example 10-3 Synthesis of A61

[0171] [ka]

[0172] Under a nitrogen atmosphere, the intermediate (AA-1002) (3.0 mmol) was dissolved in THF (50 ml), and tripotassium phosphate (7.0 mmol) and 2,2,3,3,4,4,5,5-octafluoro-1-pentanol (7.0 mmol) were added, stirred for 30 minutes, and then heated to 70°C and stirred for 6 hours. After the reaction was completed, water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethanol and ethyl acetate. The precipitated crystals were filtered to obtain the target product A61 (yield 68%). The compounds were identified by FDMS measurement.

[0173] FDMS:1838.01 Example 10-3' (Evaluation of metal adhesion of compound (A61)) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 1 Pa or less. Compound (A61) was deposited at a deposition rate of 0.2 nm / sec to form a 100 nm film on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to form a 2 nm film, followed by silver deposition at a deposition rate of 0.1 nm / sec to form a 20 nm film. No ytterbium or silver was deposited on the area on which compound (A61) was deposited, forming a 20 mm x 10 mm transparent area.

[0174] Example 10-3″ (Evaluation of adhesion of compound (A61) to CVD film) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 0.02 Pa or less. Compound (A61) was deposited at a deposition rate of 0.2 nm / sec to a thickness of 100 nm on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. Further CVD deposition was performed, and after one day, it was visually confirmed that there was no peeling in the area on which compound (A61) was deposited. [Synthesis of compound (A78) and evaluation of metal adhesion and adhesion] Example 11-1 Synthesis of intermediate (AA-1101)

[0175] [ka]

[0176] Under a nitrogen atmosphere, perfluorobenzene (9.0 mmol), DMSO (100 ml), and tripotassium phosphate (10 mmol) were added to 2,7-diamino-9,9-dimethylfluorene (3.0 mmol), and the mixture was stirred at 100°C for 20 hours. After cooling to room temperature, water (300 mL) was added and the mixture was stirred at room temperature for 30 minutes. The precipitated solid was filtered and washed with methanol. After drying at 50°C, the desired intermediate (AA-1101) was obtained (yield 80%).

[0177] The compounds were identified by FDMS measurement.

[0178] FDMS:556.10 Example 11-2 Synthesis of A78

[0179] [ka]

[0180] Under a nitrogen atmosphere, the intermediate (AA-1101) (3.0 mmol) was dissolved in THF (50 ml), AA-1101 and potassium carbonate were added, and the mixture was stirred at 70°C for 20 hours. Water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethyl acetate and ethanol. The precipitated solid was filtered to obtain the target product A78 (yield 60%). The compounds were identified by FDMS measurement.

[0181] FDMS:2032.11 Example 11-2' (Evaluation of metal adhesion of compound (A78)) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 1 Pa or less. Compound (A78) was deposited at a deposition rate of 0.2 nm / sec to form a 100 nm film on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to form a 2 nm film, followed by silver deposition at a deposition rate of 0.1 nm / sec to form a 20 nm film. No ytterbium or silver was deposited on the area on which compound (A78) was deposited, forming a 20 mm x 10 mm transparent area.

[0182] Example 11-2″ (Evaluation of adhesion of compound (A78) to CVD film) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 0.02 Pa or less. Compound (A78) was deposited at a deposition rate of 0.2 nm / sec to a thickness of 100 nm on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. Further CVD deposition was performed, and after one day, it was visually confirmed that there was no peeling in the area on which compound (A78) was deposited. [Synthesis of compound (A110) and evaluation of metal adhesion] Example 12-1 Synthesis of intermediate (AA-1201)

[0183] [ka]

[0184] Under a nitrogen atmosphere, 12H-benzo[4,5]thieno[3,2-a]carbazole (3.0mmol) was dissolved in THF (50ml), sodium hydride (7.0mmol) was added, and the mixture was stirred for 30 minutes. The mixture was then heated to 70°C, and 2,4,6-trichloropyrimidine (7.0mmol) was added. After the reaction was completed, water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethyl acetate. The precipitated crystals were filtered to obtain the target product AA-1201 (yield 58%). The compounds were identified by FDMS measurement.

[0185] FDMS:419.01 Example 12-2 Synthesis of A110

[0186] [ka]

[0187] Under a nitrogen atmosphere, the intermediate (AA-1201) (3.0 mmol) was dissolved in THF (50 ml), and tripotassium phosphate (7.0 mmol) and 1H,1H,9H-hexadecafluoro-1-nonanol (7.0 mmol) were added, stirred for 30 minutes, and then heated to 70°C and stirred for 6 hours. After the reaction was completed, water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethanol and ethyl acetate. The precipitated crystals were filtered to obtain the target product A110 (yield 63%). The compounds were identified by FDMS measurement.

[0188] FDMS:1211.05 Example 12-3' (Evaluation of metal adhesion of compound (A110)) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 1 Pa or less. A 100 nm film of compound (A110) was formed at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. No ytterbium or silver was deposited on the area on which compound (A110) was deposited, forming a 20 mm x 10 mm transparent area.

[0189] Example 12-3″ (Evaluation of adhesion of compound (A110) to CVD film) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 0.02 Pa or less. A 100 nm film of compound (A110) was formed at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. Further CVD film formation was performed, and after one day had passed, it was visually confirmed that there was no peeling in the area on which compound (A110) was deposited. [Synthesis of compound (A113) and evaluation of metal adhesion] Example 13-1 Synthesis of intermediate (AA-1301)

[0190] [ka]

[0191] Under a nitrogen atmosphere, hexafluorobenzene (9.0 mmol), DMSO (100 ml), and tripotassium phosphate (10 mmol) were added to 4-fluoro-1,2-phenylenediamine (3.0 mmol) and stirred at 100°C for 20 hours. After cooling to room temperature, water (300 mL) was added and stirred at room temperature for 30 minutes. The precipitated solid was filtered and washed with methanol. After drying at 50°C, the target intermediate (AA-1301) was obtained (yield 82%).

[0192] The compounds were identified by FDMS measurement.

[0193] FDMS:458.03 Example 13-2 Synthesis of intermediate (AA-1302)

[0194] [ka]

[0195] Under a nitrogen atmosphere, the intermediate (AA-1301) (3.0 mmol) was dissolved in THF (50 ml), sodium hydride (7.0 mmol) was added, and the mixture was stirred for 30 minutes. The mixture was then heated to 70°C, and 2,4,6-trichloropyrimidine (7.0 mmol) was added. After the reaction was completed, water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethyl acetate. The precipitated crystals were filtered to obtain the target product, AA-1302 (yield 58%). The compounds were identified by FDMS measurement.

[0196] FDMS: 731.92 Example 13-3 Synthesis of A113

[0197] [ka]

[0198] Under a nitrogen atmosphere, the intermediate (AA-1302) (3.0 mmol) was dissolved in THF (50 ml), and tripotassium phosphate (7.0 mmol) and 2,2,3,3,4,4,5,5-octafluoro-1-pentanol (7.0 mmol) were added, stirred for 30 minutes, and then heated to 70°C and stirred for 6 hours. After the reaction was completed, water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethanol and ethyl acetate. The precipitated crystals were filtered to obtain the target product A113 (yield 66%). The compounds were identified by FDMS measurement.

[0199] FDMS:1516.07 Example 13-3' (Evaluation of metal adhesion of compound (A113)) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 1 Pa or less. A 100 nm film of compound (A113) was formed at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. No ytterbium or silver was deposited on the area on which compound (A113) was deposited, forming a 20 mm x 10 mm transparent area.

[0200] Example 13-3″ (Evaluation of adhesion of compound (A113) to CVD film) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 0.02 Pa or less. A 100 nm film of compound (A113) was formed at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. Further CVD film formation was performed, and after one day had passed, it was visually confirmed that there was no peeling in the area on which compound (A113) was deposited. [Synthesis of compound (A116) and evaluation of metal adhesion] Example 14-1 Synthesis of intermediate (AA-1401)

[0201] [ka]

[0202] Under a nitrogen atmosphere, 2,3,5,6-tetrafluoro-1,4-phenylenediamine (3.0 mmol) was mixed with perfluorotoluene (9.0 mmol), DMSO (100 ml), and tripotassium phosphate (10 mmol) and stirred at 100°C for 20 hours. After cooling to room temperature, water (300 mL) was added and stirred at room temperature for 30 minutes. The precipitated solid was filtered and washed with methanol. After drying at 50°C, the target intermediate (AA-1401) was obtained (yield 84%).

[0203] The compounds were identified by FDMS measurement.

[0204] FDMS:611.99 Example 14-2 Synthesis of intermediate (AA-1402)

[0205] [ka]

[0206] Under a nitrogen atmosphere, the intermediate (AA-1401) (3.0 mmol) was dissolved in THF (50 ml), sodium hydride (7.0 mmol) was added, and the mixture was stirred for 30 minutes. The mixture was then heated to 70°C, and cyanuric chloride (7.0 mmol) was added. After the reaction was completed, water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethyl acetate. The precipitated crystals were filtered to obtain the target product, AA-1402 (yield 60%). The compounds were identified by FDMS measurement.

[0207] FDMS:833.91 Example 14-3 Synthesis of A116

[0208] [ka]

[0209] Under a nitrogen atmosphere, the intermediate (AA-1402) (3.0 mmol) was dissolved in THF (50 ml), tripotassium phosphate (7.0 mmol) and 2,2,3,3,4,4,5,5-octafluoro-1-pentanol (7.0 mmol) were added, and the mixture was stirred for 30 minutes. The mixture was then heated to 70°C and stirred for 6 hours. After the reaction was completed, water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethanol and ethyl acetate. The precipitated crystals were filtered to obtain the target product A116 (yield 68%). The compounds were identified by FDMS measurement.

[0210] FDMS:1690.02 Example 14-3' (Evaluation of metal adhesion of compound (A116)) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 1 Pa or less. A 100 nm film of compound (A116) was formed at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. No ytterbium or silver was deposited on the area on which compound (A116) was deposited, and a 20 mm x 10 mm transparent area was formed.

[0211] Example 14-3″ (Evaluation of adhesion of compound (A116) to CVD film) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4The chamber was evacuated with a vacuum pump until the pressure in the chamber was reduced to less than 1 Pa. A 100 nm film of compound (A116) was formed at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. Further CVD film formation was performed, and after one day had passed, it was visually confirmed that there was no peeling in the area on which compound (A116) was deposited. [Synthesis of compound (A128) and evaluation of metal adhesion] Example 15-1 Synthesis of intermediate (AA-1501)

[0212] [ka]

[0213] Under a nitrogen atmosphere, 9,9-dimethyl-9H-fluorene-2,7-diamine (3.0 mmol) was mixed with 4-fluorobenzotrifluoride (9.0 mmol), DMSO (100 ml), and tripotassium phosphate (10 mmol) and stirred at 100°C for 20 hours. After cooling to room temperature, water (300 mL) was added and stirred at room temperature for 30 minutes. The precipitated solid was filtered and washed with methanol. After drying at 50°C, the target intermediate (AA-1501) was obtained (yield 84%).

[0214] The compounds were identified by FDMS measurement.

[0215] FDMS:512.17 Example 15-2 Synthesis of intermediate (AA-1502)

[0216] [ka]

[0217] Under a nitrogen atmosphere, the intermediate (AA-1501) (3.0 mmol) was dissolved in THF (50 ml), sodium hydride (7.0 mmol) was added, and the mixture was stirred for 30 minutes. The mixture was then heated to 70°C, and 2,4,6-trifluoropyridine (7.0 mmol) was added. After the reaction was completed, water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethyl acetate. The precipitated crystals were filtered to obtain the target product, AA-1502 (yield 64%). The compounds were identified by FDMS measurement.

[0218] FDMS:802.07 Example 15-3 Synthesis of A128

[0219] [ka]

[0220] Under a nitrogen atmosphere, the intermediate (AA-1502) (3.0 mmol) was dissolved in THF (50 ml), sodium hydride (7.0 mmol) and 2,2,3,3,4,4,5,5-octafluoro-1-pentanol (7.0 mmol) were added, and the mixture was stirred for 30 minutes. The mixture was then heated to 70°C and stirred for 6 hours. After the reaction was completed, water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethanol and ethyl acetate. The precipitated crystals were filtered to obtain the target product A116 (yield 68%). The compounds were identified by FDMS measurement.

[0221] FDMS:1586.21 Example 15-3' (Evaluation of metal adhesion of compound (A128)) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 0.1 Pa or less. A 100 nm film of compound (A128) was formed at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. No ytterbium or silver was deposited on the area on which compound (A128) was deposited, forming a 20 mm x 10 mm transparent area.

[0222] Example 15-3″ (Evaluation of adhesion of compound (A128) to CVD film) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 0.02 Pa or less. A 100 nm film of compound (A128) was formed at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. Further CVD film formation was performed, and after one day had passed, it was visually confirmed that there was no peeling in the area on which compound (A128) was deposited. [Synthesis of compound (A150) and evaluation of metal adhesion] Example 16-1 Synthesis of intermediate (AA-1601)

[0223] [ka]

[0224] Under a nitrogen atmosphere, N-(anthracen-2-yl)anthracen-1-amine (3.0 mmol) was dissolved in THF (50 ml), sodium hydride (7.0 mmol) was added, and the mixture was stirred for 30 minutes. The mixture was then heated to 70°C, and 2,4,6-trichloro-1,3,5-triazine (7.0 mmol) was added. After the reaction was completed, water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethyl acetate. The precipitated crystals were filtered to obtain the target product AA-1601 (yield 66%). The compounds were identified by FDMS measurement.

[0225] FDMS:516.09 Example 16-3 Synthesis of A150

[0226] [ka]

[0227] Under a nitrogen atmosphere, the intermediate (AA-1601) (3.0 mmol) was dissolved in THF (50 ml), and tripotassium phosphate (7.0 mmol) and 1H,1H,7H-dodecafluoro-1-heptanol (7.0 mmol) were added, stirred for 30 minutes, and then heated to 70°C and stirred for 6 hours. After the reaction was completed, water and ethyl acetate were added, and the organic layer was taken out and dehydrated with sodium sulfate. After filtering off the sodium sulfate, the mixture was concentrated with an evaporator, and the residue was recrystallized from ethanol and ethyl acetate. The precipitated crystals were filtered to obtain the target product A150 (yield 72%). The compounds were identified by FDMS measurement.

[0228] FDMS:908.16 Example 16-3' (Evaluation of metal adhesion of compound (A150)) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4The vacuum pump was used to evacuate the chamber until the pressure reached 1 Pa or less. A 100 nm film of compound (A150) was formed at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. No ytterbium or silver was deposited on the area on which compound (A150) was deposited, forming a 20 mm x 10 mm transparent area.

[0229] Example 16-3″ (Evaluation of adhesion of compound (A150) to CVD film) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The vacuum pump was used to evacuate the chamber until the pressure in the chamber was reduced to 0.02 Pa or less. A 100 nm film of compound (A150) was formed at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. Further CVD film formation was performed, and after one day had passed, it was visually confirmed that there was no peeling in the area on which compound (A150) was deposited. Comparative Example 1-1 (Evaluation of metal adhesion of comparative compound (X0001))

[0230] [ka]

[0231] Comparative Example 1-2 (Evaluation of metal adhesion of compound (X0001)) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4The chamber was evacuated using a vacuum pump until the pressure in the chamber was reduced to 1 Pa or less. A 100 nm film of compound (X0001) was formed at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by silver being deposited at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. No ytterbium or silver was deposited on the area on which compound (X0001) was deposited, forming a 20 mm x 10 mm transparent area.

[0232] Comparative Example 1-2' (Evaluation of adhesion of compound (X0001) to CVD film) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The chamber was evacuated with a vacuum pump until the pressure in the chamber was reduced to less than 1 Pa. A 100 nm film of compound (X0001) was formed at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by silver deposition at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. Further CVD deposition was performed, and after one day, it was visually confirmed that peeling had occurred in the area where compound (X0001) had been deposited. Comparative Example 2-1' (Evaluation of metal adhesion of comparative compound (X0002))

[0233] [ka]

[0234] The adhesion of metal to compound (X0002) was evaluated in the same manner as in Comparative Example 1-2. A transparent area was formed on the film of compound (X0002). Comparative Example 2-2' (Evaluation of adhesion of compound (X0002) to CVD film) The adhesion of compound (X0002) to the CVD film was evaluated in the same manner as in Comparative Example 1-2'. It was visually confirmed that the compound (X0002) had peeled off in the vapor-deposited area. Comparative Example 3-1 (Evaluation of metal adhesion of comparative compound (X0003))

[0235] [ka]

[0236] Comparative Example 3-2 (Evaluation of metal adhesion of compound (X0003)) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The chamber was evacuated using a vacuum pump until the pressure in the chamber was reduced to 1 Pa or less. A 100 nm film of compound (X0003) was formed at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by silver being deposited at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. No ytterbium or silver was deposited on the area on which compound (X0003) was deposited, forming a 20 mm x 10 mm transparent area.

[0237] Comparative Example 3-2' (Evaluation of adhesion of compound (X0003) to CVD film) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The chamber was evacuated with a vacuum pump until the pressure in the chamber was reduced to less than 1 Pa. A 100 nm film of compound (X0003) was formed at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by silver deposition at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. Further CVD deposition was performed, and after one day, it was visually confirmed that the area on which compound (X0003) had been deposited had peeled off. Comparative Example 4-1' (Evaluation of metal adhesion of comparative compound (X0004))

[0238] [ka]

[0239] The adhesion of metal to compound (X0004) was evaluated in the same manner as in Comparative Example 1-2. A transparent region was formed on the film of compound (X0004). Comparative Example 4-2' (Evaluation of adhesion of compound (X0004) to CVD film) The adhesion of compound (X0004) to the CVD film was evaluated in the same manner as in Comparative Example 1-2'. It was visually confirmed that the compound (X0004) had peeled off in the vapor-deposited area. Comparative Example 5-1 (Evaluation of metal adhesion of comparative compound (X0005))

[0240] [ka]

[0241] Comparative Example 5-2 (Evaluation of metal adhesion of compound (X0005)) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4 The chamber was evacuated with a vacuum pump until the pressure in the chamber was reduced to 1 Pa or less. A 100 nm film of compound (X0005) was formed at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and 2 nm of ytterbium was deposited at a deposition rate of 0.01 nm / sec, followed by 20 nm of silver at a deposition rate of 0.1 nm / sec. No ytterbium or silver was deposited on the area on which compound (X0005) was deposited, forming a 20 mm x 10 mm transparent area.

[0242] Comparative Example 5-2' (Evaluation of adhesion of compound (X0005) to CVD film) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4The chamber was evacuated with a vacuum pump until the pressure in the chamber was reduced to less than 1 Pa. A 100 nm film of compound (X0005) was formed at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 20 mm x 10 mm was placed. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. Further CVD deposition was performed, and after one day, it was visually confirmed that peeling had occurred in the area where compound (X0005) had been deposited. Comparative Example 6-1' (Evaluation of metal adhesion of comparative compound (X0006))

[0243] [ka]

[0244] The adhesion of metal to compound (X0006) was evaluated in the same manner as in Comparative Example 1-2. A transparent region was formed on the film of compound (X0006). Comparative Example 6-2' (Evaluation of adhesion of compound (X0006) to CVD film) The adhesion of compound (X0006) to the CVD film was evaluated in the same manner as in Comparative Example 1-2'. It was visually confirmed that the compound (X0006) had peeled off in the vapor-deposited area. ≪Transmittance measurement≫ Metal adhesion can be evaluated by measuring the transmittance, and the transmittance decreases as metal adheres to the surface. Also, the transmittance decreases in correlation with the amount of metal adhered to the surface. 1-1. Compound-containing metal patterning materials Example 1-3: Measurement of transmittance of compound (A1) The glass substrate was washed by boiling with isopropyl alcohol, and then washed with ultraviolet light and ozone. After that, it was placed in a vacuum deposition apparatus and 1.0X10 -4The chamber was evacuated using a vacuum pump until the pressure in the chamber was reduced to below 1 Pa. A 20 nm film of compound (A1), a metal patterning material, was formed on a glass substrate at a deposition rate of 0.1 nm / sec. Furthermore, 10 nm of silver and magnesium (1:1) was deposited on the thin film of compound (A0009) at a deposition rate of 0.1 nm / sec. Transmittance measurements showed that the transmittance in the 550-800 nm range after metal deposition was "≧80%," indicating that the formation of a metal film had been suppressed. Example 2-3: Measurement of transmittance of compound (A11) The transmittance of the compound (A11) was measured in the same manner as in Example 1-3. The transmittance in the range of 550 to 800 nm after metal deposition was "≧90%", indicating that the formation of a metal film was suppressed. Example 3-3: Measurement of transmittance of compound (A18) The transmittance of the compound (A18) was measured in the same manner as in Example 1-3. The transmittance at 550 to 800 nm after metal deposition was "≧90%", indicating that the formation of a metal film was suppressed. Example 4-3: Measurement of transmittance of compound (A19) The transmittance of the compound (A19) was measured in the same manner as in Example 1-3. The transmittance in the range of 550 to 800 nm after metal deposition was "≧80%", indicating that the formation of a metal film was suppressed. Example 5-4: Measurement of transmittance of compound (A23) The transmittance of the compound (A23) was measured in the same manner as in Example 1-3. The transmittance at 550 to 800 nm after metal deposition was "≧80%", indicating that the formation of a metal film was suppressed. Example 6-4 Measurement of transmittance of compound (A50) The transmittance of the compound (A50) was measured in the same manner as in Example 1-3. The transmittance at 550 to 800 nm after metal deposition was "≧90%", indicating that the formation of a metal film was suppressed. Example 7-4: Measurement of transmittance of compound (A51) The transmittance of the compound (A51) was measured in the same manner as in Example 1-3. The transmittance in the range of 550 to 800 nm after metal deposition was "≧90%", indicating that the formation of a metal film was suppressed. Example 8-3: Measurement of transmittance of compound (A53) The transmittance of the compound (A53) was measured in the same manner as in Example 1-3. The transmittance in the range of 550 to 800 nm after metal deposition was "≧80%", indicating that the formation of a metal film was suppressed. Example 9-4: Measurement of transmittance of compound (A54) The transmittance of the compound (A54) was measured in the same manner as in Example 1-3. The transmittance in the range of 550 to 800 nm after metal deposition was "≧90%", indicating that the formation of a metal film was suppressed. Example 10-4: Measurement of transmittance of compound (A61) The transmittance of the compound (A61) was measured in the same manner as in Example 1-3. The transmittance in the range of 550 to 800 nm after metal deposition was "≧90%", indicating that the formation of a metal film was suppressed. Example 11-3: Transmittance measurement of compound (A78) The transmittance of the compound (A78) was measured in the same manner as in Example 1-3. The transmittance in the range of 550 to 800 nm after metal deposition was "≧80%", indicating that the formation of a metal film was suppressed. Example 12-4: Measurement of transmittance of compound (A110) The transmittance of the compound (A110) was measured in the same manner as in Example 1-3. The transmittance in the range of 550 to 800 nm after metal deposition was "≧90%", indicating that the formation of a metal film was suppressed. Example 13-4: Measurement of transmittance of compound (A113) The transmittance of the compound (A113) was measured in the same manner as in Example 1-3. The transmittance at 550 to 800 nm after metal deposition was "≧80%", indicating that the formation of a metal film was suppressed. Example 14-4 Transmittance measurement of compound (A116) The transmittance of the compound (A116) was measured in the same manner as in Example 1-3. The transmittance at 550 to 800 nm after metal deposition was "≧90%", indicating that the formation of a metal film was suppressed. Example 15-4: Measurement of transmittance of compound (A128) The transmittance of the compound (A128) was measured in the same manner as in Example 1-3. The transmittance in the range of 550 to 800 nm after metal deposition was "≧90%", indicating that the formation of a metal film was suppressed. Example 16-4: Measurement of transmittance of compound (A150) The transmittance of the compound (A150) was measured in the same manner as in Example 1-3. The transmittance at 550 to 800 nm after metal deposition was "≧80%", indicating that the formation of a metal film was suppressed. Comparative Example 1-2: Transmittance measurement of compound (X0001) The transmittance of the compound (X0001) was measured in the same manner as in Example 1-3. The transmittance at 550 to 800 nm after metal deposition was "≧40%", and the formation of a metal film could not be suppressed. Comparative Example 2-2" Transmittance measurement of compound (X0002) The transmittance of the compound (X0002) was measured in the same manner as in Example 1-3. The transmittance at 550 to 800 nm after metal deposition was "≧30%", and the formation of a metal film could not be suppressed. Comparative Example 3-2: Transmittance measurement of compound (X0003) The transmittance of the compound (X0003) was measured in the same manner as in Example 1-3. The transmittance at 550 to 800 nm after metal deposition was "≧40%", and the formation of a metal film could not be suppressed. Comparative Example 4-2: Transmittance measurement of compound (X0004) The transmittance of the compound (X0004) was measured in the same manner as in Example 1-3. The transmittance at 550 to 800 nm after metal deposition was "≧40%", and the formation of a metal film could not be suppressed. Comparative Example 5-2: Transmittance measurement of compound (X0005) The transmittance of the compound (X0005) was measured in the same manner as in Example 1-3. The transmittance at 550 to 800 nm after metal deposition was "≧30%", and the formation of a metal film could not be suppressed. Comparative Example 6-2: Measurement of transmittance of compound (X0006) The transmittance of the compound (X0006) was measured in the same manner as in Example 1-3. The transmittance at 550 to 800 nm after metal deposition was "≧40%", and the formation of a metal film could not be suppressed. Figure 1 shows the results for the formation of a transparent region, peeling during CVD film formation, and transmittance for each compound. Figure 1. Formation of transparent areas, peeling of CVD film, and transmittance TIFF2025022838000078.tif110127

[0245] Although the present invention has been described in detail and with reference to specific embodiments, it will be apparent to those skilled in the art that various changes and modifications can be made without departing from the spirit and scope of the invention. The present disclosure includes the following embodiments. [1] An amine compound represented by formula (1), (2) or (3):

[0246] [ka]

[0247] [ka]

[0248] [ka]

[0249] In formulas (1) to (3), Ar 101 , Ar 201 , Ar 301 are each independently any one of the following formulas (4-1) to (4-7), and * represents a bond:

[0250] [ka]

[0251] In formulas (4-1) to (4-7), R 401 ~R 409 are each independently Hydrogen atom, Deuterium atom, fluorine atom, Bromine atom, Chlorine atom, a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a fluorine atom; a linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms which may be substituted with a fluorine atom; an optionally substituted monocyclic, linked or fused ring cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms; an optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 25 carbon atoms; an optionally substituted monocyclic, linked or fused heteroaromatic group having 3 to 25 carbon atoms, or Represented by the following formula (5):

[0252] [ka]

[0253] In formula (5), L 501 and L 502 are each independently a linear or branched divalent aliphatic hydrocarbon group having 1 to 4 carbon atoms; Oxygen atom, Sulfur atom, or Represents a single bond; n represents an integer from 0 to 11; * represents a bond. In formula (4-1), R 401 and R 402 At least one of the following is expressed by Equation (5): In formulas (4-2) to (4-4), R 403 ~R 405At least one of the following is expressed by Equation (5): In formulas (4-5) to (4-7), R 406 ~R 409 At least one of the following is expressed by Equation (5): In formulas (1) to (3), R 101 , R 102 , R 201 ~R 203 , R 301 ~R 306 are each independently an optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 25 carbon atoms; an optionally substituted monocyclic, linked or fused heteroaromatic group having 3 to 25 carbon atoms, or represents an optionally substituted linear, branched or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms; L 101 ~L 103 , L 201 ~L 206 , L 301 ~L 309 are each independently an optionally substituted monocyclic, linked or fused ring divalent aromatic hydrocarbon group having 6 to 25 carbon atoms; an optionally substituted monocyclic, linked, or fused divalent heteroaromatic group having 3 to 25 carbon atoms, or Represents a single bond; L 102 and L 103 is a single bond, R 101 and R 102 may be linked together to form a ring; X is an optionally substituted di- to tetravalent aromatic hydrocarbon group having 6 to 25 carbon atoms and being a monocyclic, linked or fused ring; an optionally substituted di- to tetravalent monocyclic, linked or fused ring heteroaromatic group having 3 to 25 carbon atoms; an optionally substituted linear, branched or cyclic divalent to tetravalent aliphatic hydrocarbon group having 1 to 20 carbon atoms; an optionally substituted di- to tetravalent cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms and being a monocyclic, linked or fused ring, or represents an optionally substituted silicon atom; a and b each independently represent an integer of 1 to 3; c and d each independently represent an integer of 1 or 2; e represents an integer of 0 or 1. [2] Ar in formulas (1) to (3) 101 , Ar 201 , Ar 301 each independently represents one of the following formulas (6-1) to (6-22):

[0254] [ka]

[0255] [ka]

[0256] [ka]

[0257] In formulas (6-1) to (6-22), R 501 ~R 549 are each independently Hydrogen atom, deuterium atom, fluorine atom, bromine atom, chlorine atom, a linear or branched aliphatic hydrocarbon group having 1 to 4 carbon atoms which may be substituted with a fluorine atom; a linear or branched alkoxy group having 1 to 4 carbon atoms which may be substituted with a fluorine atom, or a cyclic aliphatic hydrocarbon group having 5 to 20 carbon atoms which may be substituted; an optionally substituted cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms; an aromatic hydrocarbon group having 6 to 20 carbon atoms which may be substituted, or represents an optionally substituted heteroaromatic group having 3 to 20 carbon atoms; L 601 ~L 630 are each independently represents a linear or branched divalent aliphatic hydrocarbon group having 1 to 4 carbon atoms, an oxygen atom, a sulfur atom, or a single bond; L 701 ~L 730 are each independently Straight chain with 1 to 4 carbon atoms, or represents a branched divalent aliphatic hydrocarbon group, an oxygen atom, a sulfur atom, or a single bond; p and q each independently represent an integer of 0 to 11; * represents a bond; [3] R 101 ~R 102 , R 201 ~R 203 , R 301 ~R 306 wherein each of the above is independently represented by either (i) or (ii) below:

[0258] (i) a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a phenanthryl group, a fluoranthenyl group, a triphenylenyl group, an anthryl group, a pyrenyl group, a pyridyl group, an indolyl group, a carbazolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, an adamantyl group, or a group represented by any of the formulas (4-1) to (4-7); (ii) The group represented by (i) is substituted with one or more groups selected from the group consisting of a methyl group, an ethyl group, a methoxy group, an ethoxy group, a trifluoromethyl group, a trifluoromethoxy group, a perfluoroalkyl group having 2 to 10 carbon atoms, a perfluoroalkoxy group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group which may be substituted with a fluorine atom, a tolyl group which may be substituted with a fluorine atom, a biphenylyl group which may be substituted with a fluorine atom, a naphthyl group which may be substituted with a fluorine atom, a phenanthryl group which may be substituted with a fluorine atom, a pyridyl group which may be substituted with a fluorine atom, a carbazolyl group which may be substituted with a fluorine atom, a dibenzothienyl group which may be substituted with a fluorine atom, and a dibenzofuranyl group which may be substituted with a fluorine atom. [4] L 101 ~L 103 , L 201 ~L 206 , L 301 ~L 309 each independently represents any one of the following (iii) to (v):

[0259] (iii) a phenylene group, a biphenylylene group, a terphenylene group, a naphthylene group, a pyridylene group, or a fluorenylene group; (iv) the group represented by (iii) is substituted with one or more groups selected from the group consisting of a methyl group, an ethyl group, a methoxy group, an ethoxy group, a trifluoromethyl group, a trifluoromethoxy group, a perfluoroalkyl group having 2 to 10 carbon atoms, a perfluoroalkoxy group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group which may be substituted with a fluorine atom, a tolyl group which may be substituted with a fluorine atom, a biphenylyl group which may be substituted with a fluorine atom, a naphthyl group which may be substituted with a fluorine atom, a phenanthryl group which may be substituted with a fluorine atom, a pyridyl group which may be substituted with a fluorine atom, a carbazolyl group which may be substituted with a fluorine atom, a dibenzothienyl group which may be substituted with a fluorine atom, and a dibenzofuranyl group which may be substituted with a fluorine atom; (v) A single bond. [5] The amine compound according to any one of [1] to [4], wherein X is represented by any one of the following (vi) to (vii):

[0260] (vi) A phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a fluorenylene group, a spirobifluorenylene group, a benzofluorenylene group, a phenanthrene group, a fluoranthenylene group, a triphenylenylene group, an anthracenediyl group, a pyridylene group, a pyrimidinediyl group, a triazinediyl group, a carbazolediyl group, a benzofurandiyl group, a benzothiophenediyl group, a dibenzofurandiyl group, an adamantanediyl group, a phenyl group, a methylene group, a silanediyl group, a cyclohexylene group, a phenyltriyl group, a biphenyltriyl group, a terphenyltriyl group, a naphthyltriyl group, a fluorenetriyl group, a spirobifluorenetriyl group, a benzofluorenetriyl group, a phenanthrenetriyl group, a fluoranthentriyl group, a triphenylenetriyl group, an anthracenetriyl group, a pyrenetriyl group, a pyridinetriyl group, a pyrimidinetriyl group, a triphenylene ... an azinetriyl group, a carbazoletriyl group, a benzofurantriyl group, a benzothiophenetriyl group, a dibenzofurantriyl group, an adamantanetriyl group, a methanetriyl group, a silanetriyl group, a cyclohexanetriyl group, a phenyltetrayl group, a biphenyltetrayl group, a terphenyltetrayl group, a naphthyltetrayl group, a fluorenetetrayl group, a spirobifluorenetetrayl group, a benzofluorenetetrayl group, a phenanthrenetetrayl group, a fluoranthenetetrayl group, a triphenylenetetrayl group, an anthracenetetrayl group, a pyrenetetrayl group, a pyridinetetrayl group, a pyrimidinetetrayl group, a carbazoletetrayl group, a benzofurantetrayl group, a benzothiophenetetrayl group, a dibenzofurantetrayl group, an adamantanetetrayl group, a methanetetrayl group, a silanetetrayl group, or a cyclohexanetetrayl group; (vii) The group represented by (vi) is substituted with one or more groups selected from the group consisting of a methyl group, an ethyl group, a methoxy group, an ethoxy group, a trifluoromethyl group, a trifluoromethoxy group, a perfluoroalkyl group having 2 to 10 carbon atoms, a perfluoroalkoxy group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group which may be substituted with a fluorine atom, a tolyl group which may be substituted with a fluorine atom, a biphenylyl group which may be substituted with a fluorine atom, a naphthyl group which may be substituted with a fluorine atom, a phenanthryl group which may be substituted with a fluorine atom, a pyridyl group which may be substituted with a fluorine atom, a carbazolyl group which may be substituted with a fluorine atom, a dibenzothienyl group which may be substituted with a fluorine atom, and a dibenzofuranyl group which may be substituted with a fluorine atom. [6] The amine compound according to any one of [1] to [5], having two or more substituents represented by the formula (5) in the molecule. [7] The metal patterning material according to any one of [1] to [6]. [8] A thin film for metal patterning, which contains the amine compound according to any one of [1] to [6] and can pattern a metal film or a metal laminate film, wherein the metal film or the metal laminate film contains one or more metals selected from the group consisting of lithium, ytterbium, silver, aluminum, and magnesium, or an alloy containing one or more of these metals. [9] A method for forming a metal pattern, comprising: forming an organic material pattern containing the amine compound according to any one of [1] to [6]; and applying a metal material to a formation region of the organic material pattern and an unformed region of the organic material pattern, thereby forming a metal pattern in the unformed region.

[10] An organic electroluminescence element including a cathode, the cathode containing one or more metals selected from the group consisting of lithium, ytterbium, silver, aluminum, and magnesium, or an alloy containing one or more of these metals, and the cathode being patterned with the amine compound according to any one of items [1] to [6].

[11] An electronic device comprising the amine compound according to any one of [1] to [6].

Claims

1. An amine compound represented by formula (1), (2) or (3): 【Chemistry 1】 【Chemistry 2】 【Chemistry 3】 In formulas (1) to (3), Ar １０１ , Ar ２０１ , Ar ３０１ are each independently any one of the following formulas (4-1) to (4-7), and * represents a bond: 【Chemistry 4】 In formulas (4-1) to (4-7), R ４０１ ~R ４０９ are each independently Hydrogen atoms, Deuterium atom, fluorine atom, Bromine atom, Chlorine atom, a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms which may be substituted with a fluorine atom; a linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms which may be substituted with a fluorine atom; an optionally substituted monocyclic, linked or condensed heterocyclic aliphatic hydrocarbon group having 3 to 20 carbon atoms; an optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 25 carbon atoms; an optionally substituted monocyclic, linked, or condensed heteroaromatic group having 3 to 25 carbon atoms, or Represented by the following formula (5): 【Chemistry 5】 In formula (5), L ５０１ and L ５０２ are each independently a linear or branched divalent aliphatic hydrocarbon group having 1 to 4 carbon atoms, Oxygen atom, Sulfur atom, or Represents a single bond; n represents an integer from 0 to 11; * represents a bond. In formula (4-1), R ４０１ and R ４０２ At least one of the above is represented by formula (5); In formulas (4-2) to (4-4), R ４０３ ~R ４０５ At least one of the above is represented by formula (5); In formulas (4-5) to (4-7), R ４０６ ~R ４０９ At least one of the above is represented by formula (5); In formulas (1) to (3), R １０１ , R １０２ , R ２０１ ~R ２０３ , R ３０１ ~R ３０６ are each independently an optionally substituted monocyclic, linked or condensed aromatic hydrocarbon group having 6 to 25 carbon atoms; an optionally substituted monocyclic, linked, or condensed heteroaromatic group having 3 to 25 carbon atoms, or represents an optionally substituted linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms; L １０１ ~L １０３ , L ２０１ ~L ２０６ , L ３０１ ~L ３０９ are each independently an optionally substituted monocyclic, linked or condensed ring divalent aromatic hydrocarbon group having 6 to 25 carbon atoms, an optionally substituted monocyclic, linked, or fused divalent heteroaromatic group having 3 to 25 carbon atoms, or Represents a single bond; L １０２ and L １０３ is a single bond, R １０１ and R １０２ may be bonded to each other to form a ring; X is, an optionally substituted di-, tri- or tetravalent aromatic hydrocarbon group having 6 to 25 carbon atoms and being a monocyclic, linked or condensed ring; an optionally substituted di-, tri- or tetravalent monocyclic, linked or fused ring heteroaromatic group having 3 to 25 carbon atoms; an optionally substituted linear, branched or cyclic di- to tetravalent aliphatic hydrocarbon group having 1 to 20 carbon atoms; an optionally substituted, monocyclic, linked, or fused, di- to tetravalent cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms, or represents an optionally substituted silicon atom; a and b each independently represent an integer of 1 to 3; c and d each independently represent an integer of 1 or 2; e represents an integer of 0 or 1.

2. Ar in formulas (1) to (3) １０１ , Ar ２０１ , Ar ３０１ are each independently represented by the following formulas (6-1) to (6-22): 【Chemistry 6】 【Chemistry 7】 【Chemistry 8】 In formulas (6-1) to (6-22), R ５０１ ~R ５４９ are each independently Hydrogen atom, deuterium atom, fluorine atom, bromine atom, chlorine atom, a linear or branched aliphatic hydrocarbon group having 1 to 4 carbon atoms which may be substituted with a fluorine atom; a linear or branched alkoxy group having 1 to 4 carbon atoms which may be substituted with a fluorine atom, or a cyclic aliphatic hydrocarbon group having 5 to 20 carbon atoms which may be substituted, a cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms which may be substituted; an aromatic hydrocarbon group having 6 to 20 carbon atoms which may be substituted, or represents an optionally substituted heteroaromatic group having 3 to 20 carbon atoms; L ６０１ ~L ６３０ are each independently represents a linear or branched divalent aliphatic hydrocarbon group having 1 to 4 carbon atoms, an oxygen atom, a sulfur atom, or a single bond; L ７０１ ~L ７３０ are each independently Straight chain with 1 to 4 carbon atoms, or represents a branched divalent aliphatic hydrocarbon group, an oxygen atom, a sulfur atom, or a single bond; p and q each independently represent an integer of 0 to 11; * represents a bond;

3. R １０１ ~R １０２ , R ２０１ ~R ２０３ , R ３０１ ~R ３０６ The amine compound according to claim 1 , wherein each of the above is independently represented by any one of the following (i) and (ii): (i) a phenyl group, a biphenylyl group, a terphenylyl group, a naphthyl group, a fluorenyl group, a spirobifluorenyl group, a benzofluorenyl group, a phenanthryl group, a fluoranthenyl group, a triphenylenyl group, an anthryl group, a pyrenyl group, a pyridyl group, an indolyl group, a carbazolyl group, a benzofuranyl group, a benzothienyl group, a dibenzofuranyl group, a dibenzothienyl group, an adamantyl group, or a group represented by any of the formulas (4-1) to (4-7); (ii) The group represented by (i) is substituted with one or more groups selected from the group consisting of a methyl group, an ethyl group, a methoxy group, an ethoxy group, a trifluoromethyl group, a trifluoromethoxy group, a perfluoroalkyl group having 2 to 10 carbon atoms, a perfluoroalkoxy group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group which may be substituted with a fluorine atom, a tolyl group which may be substituted with a fluorine atom, a biphenylyl group which may be substituted with a fluorine atom, a naphthyl group which may be substituted with a fluorine atom, a phenanthryl group which may be substituted with a fluorine atom, a pyridyl group which may be substituted with a fluorine atom, a carbazolyl group which may be substituted with a fluorine atom, a dibenzothienyl group which may be substituted with a fluorine atom, and a dibenzofuranyl group which may be substituted with a fluorine atom.

4. L １０１ ~L １０３ , L ２０１ ~L ２０６ , L ３０１ ~L ３０９ are each independently represented by any one of the following (iii) to (v): (iii) a phenylene group, a biphenylylene group, a terphenylene group, a naphthylene group, a pyridylene group, or a fluorenylene group; (iv) the group represented by (iii) is substituted with one or more groups selected from the group consisting of a methyl group, an ethyl group, a methoxy group, an ethoxy group, a trifluoromethyl group, a trifluoromethoxy group, a perfluoroalkyl group having 2 to 10 carbon atoms, a perfluoroalkoxy group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group which may be substituted with a fluorine atom, a tolyl group which may be substituted with a fluorine atom, a biphenylyl group which may be substituted with a fluorine atom, a naphthyl group which may be substituted with a fluorine atom, a phenanthryl group which may be substituted with a fluorine atom, a pyridyl group which may be substituted with a fluorine atom, a carbazolyl group which may be substituted with a fluorine atom, a dibenzothienyl group which may be substituted with a fluorine atom, and a dibenzofuranyl group which may be substituted with a fluorine atom; (v) a single bond.

5. The amine compound according to claim 1, wherein X is represented by any one of the following (vi) to (vii): (vi) a phenylene group, a biphenylene group, a terphenylene group, a naphthylene group, a fluorenylene group, a spirobifluorenylene group, a benzofluorenylene group, a phenanthrene group, a fluoranthenylene group, a triphenylenylene group, an anthracenediyl group, a pyridylene group, a pyrimidinediyl group, a triazinediyl group, a carbazolediyl group, a benzofurandiyl group, a benzothiophenediyl group, a dibenzofurandiyl group, an adamantanediyl group, a phenyl group, a methylene group, a silanediyl group, a cyclohexylene group, a phenyltriyl group, a biphenyltriyl group, a terphenyltriyl group, a naphthyltriyl group, a fluorenetriyl group, a spirobifluorenetriyl group, a benzofluorenetriyl group, a phenanthrenetriyl group, a fluoranthentriyl group, a triphenylenetriyl group, an anthracenetriyl group, a pyrenetriyl group, a pyridinetriyl group, a pyrimidinetriyl group, a triphenylene ... an azinetriyl group, a carbazoletriyl group, a benzofurantriyl group, a benzothiophenetriyl group, a dibenzofurantriyl group, an adamantanetriyl group, a methanetriyl group, a silanetriyl group, a cyclohexanetriyl group, a phenyltetrayl group, a biphenyltetrayl group, a terphenyltetrayl group, a naphthyltetrayl group, a fluorenetetrayl group, a spirobifluorenetetrayl group, a benzofluorenetetrayl group, a phenanthrenetetrayl group, a fluoranthenetetrayl group, a triphenylenetetrayl group, an anthracenetetrayl group, a pyrenetetrayl group, a pyridinetetrayl group, a pyrimidinetetrayl group, a carbazoletetrayl group, a benzofurantetrayl group, a benzothiophenetetrayl group, a dibenzofurantetrayl group, an adamantanetetrayl group, a methanetetrayl group, a silanetetrayl group, or a cyclohexanetetrayl group; (vii) The group represented by (vi) is substituted with one or more groups selected from the group consisting of a methyl group, an ethyl group, a methoxy group, an ethoxy group, a trifluoromethyl group, a trifluoromethoxy group, a perfluoroalkyl group having 2 to 10 carbon atoms, a perfluoroalkoxy group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group which may be substituted with a fluorine atom, a tolyl group which may be substituted with a fluorine atom, a biphenylyl group which may be substituted with a fluorine atom, a naphthyl group which may be substituted with a fluorine atom, a phenanthryl group which may be substituted with a fluorine atom, a pyridyl group which may be substituted with a fluorine atom, a carbazolyl group which may be substituted with a fluorine atom, a dibenzothienyl group which may be substituted with a fluorine atom, and a dibenzofuranyl group which may be substituted with a fluorine atom.

6. The amine compound according to claim 1, having two or more substituents represented by the formula (5) in the molecule.

7. The metal patterning material according to any one of claims 1 to 6.

8. 7. A thin film for metal patterning, comprising the amine compound according to claim 1, capable of patterning a metal film or a metal laminate film, the metal film or the metal laminate film containing one or more metals selected from the group consisting of lithium, ytterbium, silver, aluminum, and magnesium, or an alloy containing one or more of these metals.

9. 7. A method for forming a metal pattern, comprising: forming an organic material pattern containing the amine compound according to claim 1; and applying a metal material to a formation region of the organic material pattern and an unformed region of the organic material pattern, thereby forming a metal pattern in the unformed region.

10. 7. An organic electroluminescence element comprising a cathode, the cathode containing one or more metals selected from the group consisting of lithium, ytterbium, silver, aluminum, and magnesium, or an alloy containing one or more of these metals, and the cathode being patterned with the amine compound according to any one of claims 1 to 6.

11. An electronic device comprising the amine compound according to any one of claims 1 to 6.

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