Material for metal patterning, heterocyclic compound, thin film for metal patterning, organic electroluminescent element, electronic device, and method for forming metal pattern

Abstract

Provided are: a compound which is capable of suppressing, at a high level, the formation of a metal thin film on a film surface; a material for metal patterning, which contains the compound; a thin film for metal patterning, which uses the material for metal patterning; an organic electroluminescent element; a method for forming a metal pattern; and an electronic device.　The material for metal patterning includes, for example, a compound represented by formula (A2). [Chemical formula 1] In formula (A2), R1 and R2 are each independently represented by formula (B1). [Chemical formula 2] In formula (B1), each Rf1 independently represents a monovalent or divalent substituent having three or more fluorine atoms and one or more carbon atoms.

Description

Metal patterning material, heterocyclic compound, metal patterning thin film, organic electroluminescence element, electronic device, and method for forming metal pattern

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

[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 they must be patterned into desired shapes.

[0003] A known method for patterning a metal electrode is to form a patterned film using a metal patterning material that is inhibited from adhering to the metal as a base layer, and then vapor-deposit a metal on top of the base layer. This method selectively forms a metal film in areas where the metal patterning material is not formed, making it possible to form a metal electrode patterned in a desired shape.

[0004] Patent Document 1 discloses a technique for patterning magnesium metal using an anthracene derivative as a material for metal patterning.

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

[0006] International Publication No. 2020 / 225778

[0007] One aspect of the present disclosure is directed to providing a metal patterning material, a heterocyclic compound, a metal patterning thin film, an organic electroluminescence element, a method for forming a metal pattern, and an electronic device, which are expected to be able to suppress the formation of various metal thin films on a film surface with higher precision than conventional methods.

[0008] As a result of extensive research into solving the above problems, the present inventors discovered a specific material for metal patterning, which will be described later, and completed the present invention.

[0009] [1] A material for metal patterning, comprising a compound represented by the following formula (A2): In formula (A2), Z １ , Z ２ each independently represents an optionally substituted di- to tetravalent monocyclic, linked ring, or fused ring aromatic hydrocarbon group having 6 to 26 carbon atoms, an optionally substituted di- to tetravalent monocyclic, linked ring, or fused ring heteroaromatic group having 3 to 11 carbon atoms, an optionally substituted di- to tetravalent cyclic aliphatic hydrocarbon group having 3 to 18 carbon atoms, or an optionally substituted di- to tetravalent cyclic heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms. １ represents an optionally substituted monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group having 6 to 26 carbon atoms, an optionally substituted monocyclic, linked ring, or fused ring divalent heteroaromatic group having 3 to 26 carbon atoms, an optionally substituted cyclic divalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, an optionally substituted cyclic divalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, or a single bond. １ Each of G independently represents an optionally substituted pyridyl group or an optionally substituted pyrimidyl group. ２ each independently represents an optionally substituted pyridyl group, an optionally substituted pyrimidyl group, or an optionally substituted triazyl group. In formula (A2), a, b, d, and e each independently represent an integer of 1 to 3. In formula (A2), c represents an integer of 0 to 2. In formula (A2), R １ and R ２ are each independently represented by the following formula (B1). In formula (B1), L ２represents O, S, a linear, branched or cyclic divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may be substituted with a fluorine atom, or a vinylene group which may be substituted with a fluorine atom and which may form a ring. In formula (B1), each f independently represents an integer of 0 to 4. In formula (B1), each g independently represents an integer of 1 to 4. In formula (B1), Rf １ each independently represents a monovalent or divalent substituent having one or more carbon atoms and containing three or more fluorine atoms.

[0010] [2] Z １ , and Z ２ the material for metal patterning according to the above [1], wherein in the case of an aromatic hydrocarbon group having at least one substituent, a heteroaromatic group having a substituent, an aliphatic hydrocarbon group having a substituent, or a heteroaliphatic hydrocarbon group having a substituent, these substituents are each independently a linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, or a structure represented by formula (B1) (wherein these substituents may be further substituted with one or more substituents selected from the group consisting of these substituents).

[0011] [3] In the case of at least one of the following (a) or (b), (a) G １ (b) G is a substituted pyridyl group or a substituted pyrimidyl group; ２is a substituted pyridyl group, a substituted pyrimidyl group, or a substituted triazyl group, and the substituents of (a) and (b) are each independently a linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, or a structure represented by formula (B1) (wherein these substituents may be further substituted with one or more substituents selected from the group consisting of these substituents).

[0012] [4] Z １ , and Z ２ are each independently a divalent to tetravalent aromatic hydrocarbon group of a monocyclic, linked ring, or fused ring having a structure in which phenyl or a plurality of benzene rings are linked or fused, or a divalent to tetravalent heteroaromatic group of a monocyclic, linked ring, or fused ring having a 5-membered ring, 6-membered ring, or a fused structure thereof, in which the heteroatom is N, O, or S.

[0013] [5] Z １ , and Z ２(a) a monocyclic, linked or fused ring divalent to tetravalent aromatic hydrocarbon group selected from the group consisting of benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, and groups formed by condensing any of these groups with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene; (b) a monocyclic, linked ring, or fused ring divalent to tetravalent heteroaromatic group selected from the group consisting of pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, benzofuran, benzothiophene, benzodioxin, thiazole, thiadiazole, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and benzothiazole; (c) a cyclic divalent to tetravalent aliphatic hydrocarbon group selected from the group consisting of adamantane, diamantane, norbornene, and cyclohexane; or (d) The material for metal patterning according to any one of the above [1] to [4], which is a cyclic divalent to tetravalent heteroaliphatic hydrocarbon group selected from the group consisting of morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane.

[0014] [6] Z １ , and Z ２are each independently a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a thiazolyl group, a benzothiazolyl group, or a structure represented by formula (B1) (wherein these substituents may be further substituted with one or more substituents selected from the group consisting of these substituents).

[0015] [7] L １ is a monocyclic, linked, or fused ring divalent aromatic hydrocarbon group having a structure in which phenyl or a plurality of benzene rings are linked or fused, or a monocyclic, linked, or fused ring divalent heteroaromatic group in which the heteroatom is N, O, or S and has a 5-membered ring, 6-membered ring, or a structure in which these are fused.

[0016] [8] L １(a) a monocyclic, linked ring, or fused ring divalent to tetravalent aromatic hydrocarbon group selected from the group consisting of benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, and dibenzochrysene, and groups formed by condensing any of these groups with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene; (b) a monocyclic, linked, or fused di- to tetravalent heteroaromatic group selected from the group consisting of pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and benzothiazole, as well as groups formed by condensing these groups with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene; (c) a cyclic di- to tetravalent aliphatic hydrocarbon group selected from the group consisting of adamantane, diamantane, norbornene, and cyclohexane; or (d) The material for metal patterning according to any one of the above [1] to [7], which is a cyclic divalent to tetravalent heteroaliphatic hydrocarbon group selected from the group consisting of morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane.

[0017] [9] L １is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a cyclic heteroaliphatic hydrocarbon group, these substituents are each independently a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, or a structure represented by formula (B1) (wherein these substituents may be further substituted with one or more substituents selected from the group consisting of these substituents).

[0018]

[10] A heterocyclic compound represented by the following formula (A3): In formula (A3), Y １ , Y ２ each independently represents an optionally substituted di- to tetravalent monocyclic, linked ring, or fused ring aromatic hydrocarbon group having 6 to 26 carbon atoms, an optionally substituted di- to tetravalent monocyclic, linked ring, or fused ring heteroaromatic group having 3 to 11 carbon atoms, an optionally substituted di- to tetravalent cyclic aliphatic hydrocarbon group having 3 to 18 carbon atoms, or an optionally substituted di- to tetravalent cyclic heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms. ３ represents an optionally substituted monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group having 6 to 26 carbon atoms, an optionally substituted monocyclic, linked ring, or fused ring divalent heteroaromatic group having 3 to 26 carbon atoms, an optionally substituted cyclic divalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, an optionally substituted cyclic divalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, or a single bond. ３ Each of the groups independently represents an optionally substituted pyridyl group or an optionally substituted pyrimidyl group. ４each independently represents an optionally substituted pyridyl group, an optionally substituted pyrimidyl group, or an optionally substituted triazyl group. In formula (A3), h and i each independently represent an integer of 1 to 3. In formula (A3), k and m each independently represent an integer of 2 to 3. In formula (A3), j represents an integer of 0 to 2. In formula (A3), R ３ and R ４ are each independently represented by the following formula (B2). In formula (B2), L ４ represents O, S, a linear, branched or cyclic divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may be substituted with a fluorine atom, or a vinylene group which may be substituted with a fluorine atom and which may form a ring. In formula (B2), each n independently represents an integer of 0 to 4. In formula (B2), each p independently represents an integer of 1 to 4. In formula (B2), Rf ２ each independently represents a monovalent or divalent substituent having one or more carbon atoms and containing three or more fluorine atoms.

[0019]

[11] In formula (A3), Y １ , Y ２ has a substituent, the substituents are each independently a linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, a structure represented by the above formula (B2), or a structure in which these substituents are further substituted with one or more substituents selected from the group consisting of these groups.

[0020]

[12] In formula (A3), G ３ , G ４has a substituent, the substituents are each independently a linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, a structure represented by formula (B2), or a structure in which these substituents are further substituted with one or more substituents selected from the group consisting of these substituents.

[0021]

[13] In formula (A3), L ３ has a substituent, the substituent is each independently a linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, a structure represented by formula (B2), or a structure in which these substituents are further substituted with one or more substituents selected from the group consisting of these substituents.

[0022]

[14] Y １ , Y ２ The monocyclic, linked or condensed divalent to tetravalent aromatic hydrocarbon group represented by the following formula (I) has a structure in which phenyl or a plurality of benzene rings are linked or condensed, and Y １ , Y ２ The heteroatom is N, O or S, and the heteroaromatic group is a 5-membered ring, a 6-membered ring, a 7-membered ring, or a structure in which these are linked or fused together, and Y １ , Y ２ The heterocyclic compound according to any one of the above

[10] to

[13] , wherein the cyclic divalent to tetravalent heteroaliphatic hydrocarbon group represented by the following formula (I) is a 5-membered ring, a 6-membered ring, a 7-membered ring, or a structure in which the heteroatom is N, O, or S and the ring is bonded or condensed thereto.

[0023]

[15] In formula (A3), Y １ , Y ２are each independently benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, or any of these groups fused with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene; and Y １ , Y ２ compounds which provide a monocyclic, linked-ring or fused-ring heteroaromatic group represented by the formula (I) are each independently pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, benzofuran, benzothiophene, benzodioxin, thiazole, thiadiazole, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, or benzothiazole, and Y １ , Y ２ The compounds providing the cyclic divalent to tetravalent aliphatic hydrocarbon groups represented by the formula: are each independently adamantane, diamantane, or cyclohexane, and Y １ , Y ２ The heterocyclic compound according to any one of the above

[10] to

[14] , wherein the compounds providing the cyclic heteroaliphatic hydrocarbon group represented by the formula (I) are each independently morpholine, piperidine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, or 1,4,7,10-tetraazacyclododecane.

[0024]

[16] In formula (A3), L ３ The monocyclic, linked or condensed divalent aromatic hydrocarbon group represented by the formula: ３The monocyclic, linked or fused divalent heteroaromatic group represented by the formula (I) is a 5-membered ring, a 6-membered ring, a 7-membered ring, or a structure in which the heteroatom is N, O or S and the ring is linked or fused thereto, ３ The heterocyclic compound according to any one of the above

[10] to

[15] , wherein the cyclic divalent heteroaliphatic hydrocarbon group represented by the following formula (I) is a 5-membered ring, a 6-membered ring, a 7-membered ring, or a structure in which the heteroatom is N, O, or S and the ring is linked or condensed therewith.

[0025]

[17] In formula (A3), L ３ compounds which provide a monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group represented by the formula (I) are each independently benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, or any of these groups fused with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene; ３ compounds which provide a monocyclic, linked ring, or fused ring divalent heteroaromatic group represented by the formula (I) are each independently pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, or any of these groups fused with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene; ３ The compounds providing the cyclic divalent aliphatic hydrocarbon group represented by the formula (I) are each independently adamantane, diamantane, norbornene, or cyclohexane, and L ３The heterocyclic compound according to any one of the above

[10] to

[16] , wherein the compounds providing the cyclic divalent heteroaliphatic hydrocarbon group represented by the formula (I) are each independently morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiane, 4,4'-bipiperidine, 3,3'-bipiperidine, 2,2'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, or 1,4,7,10-tetraazacyclododecane.

[0026]

[18] A thin film for metal patterning, which contains a metal patterning material and can pattern a metal film or a metal laminate film, wherein the metal patterning material contains the metal patterning material according to any one of [1] to [9] above or the heterocyclic compound according to any one of

[10] to

[17] above, and the metal film or the metal laminate film contains one or more metals selected from the group consisting of lithium, ytterbium, magnesium, silver, and aluminum, or an alloy containing one or more of these metals.

[0027]

[19] The thin film for metal patterning according to the above

[18] , which has a water contact angle of 90° or more.

[0028]

[20] An organic electroluminescence element including a cathode, wherein the cathode contains one or more metals selected from the group consisting of lithium, ytterbium, magnesium, silver, and aluminum, or an alloy containing one or more of these metals, and is patterned with a metal patterning material, wherein the metal patterning material contains the metal patterning material according to any one of [1] to [9] above, or the heterocyclic compound according to any one of

[10] to

[17] above.

[0029]

[21] A method for forming a metal pattern, comprising: forming an organic material pattern containing the metal patterning material according to any one of [1] to [9] above, or the heterocyclic compound according to any one of

[10] to

[17] above; 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.

[0030]

[22] An electronic device comprising the metal patterning material according to any one of [1] to [9] above, or the heterocyclic compound according to any one of

[10] to

[17] above.

[0031] According to one aspect of the present disclosure, it is possible to provide a novel material for metal patterning, which is expected to suppress the formation of a metal thin film on a film surface, a heterocyclic compound, a thin film for metal patterning, an organic electroluminescence element, a method for forming a metal pattern, and an electronic device.

[0032] FIG. 2 is a diagram showing the results of transmittance measurement for Example 4″. FIG. 3 is a diagram showing the results of transmittance measurement for Comparative Example 0″. FIG. 4 is a diagram showing the results of transmittance measurement for Comparative Example 1″. FIG. 5 is a diagram showing the results of transmittance measurement for Reference Example 1″. FIG. 6 is a schematic cross-sectional view showing an example of the configuration of an organic electroluminescence element. FIG. 7 is a schematic cross-sectional view showing an example of the configuration of the cathode patterning layer of FIG. 1. FIG. 8 is a schematic top view showing an example of the configuration of the cathode patterning layer of FIG. 1.

[0033] Hereinafter, a metal patterning material, a metal patterning thin film, an organic electroluminescence element, an electronic device, and a method for forming a metal pattern according to one embodiment of the present disclosure will be described in detail.

[0034] [First Aspect: Metal Patterning Material] A metal patterning material according to one aspect of the present disclosure includes a compound represented by the following formula (A2). In formula (A2), Z １ , Z ２each independently represents an optionally substituted di- to tetravalent monocyclic, linked ring, or fused ring aromatic hydrocarbon group having 6 to 26 carbon atoms, an optionally substituted di- to tetravalent monocyclic, linked ring, or fused ring heteroaromatic group having 3 to 11 carbon atoms, an optionally substituted di- to tetravalent cyclic aliphatic hydrocarbon group having 3 to 18 carbon atoms, or an optionally substituted di- to tetravalent cyclic heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms. １ represents an optionally substituted monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group having 6 to 26 carbon atoms, an optionally substituted monocyclic, linked ring, or fused ring divalent heteroaromatic group having 3 to 26 carbon atoms, an optionally substituted cyclic divalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, an optionally substituted cyclic divalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, or a single bond.

[0035] In formula (A2), G １ Each of G independently represents an optionally substituted pyridyl group or an optionally substituted pyrimidyl group. ２ each independently represents an optionally substituted pyridyl group, an optionally substituted pyrimidyl group, or an optionally substituted triazyl group. In formula (A2), a, b, d, and e each independently represent an integer of 1 to 3. In formula (A2), c represents an integer of 0 to 2.

[0036] In formula (A2), R １ and R ２ are each independently represented by the following formula (B1). In formula (B1), L ２ represents O, S, a linear, branched or cyclic divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may be substituted with a fluorine atom, or a vinylene group which may be substituted with a fluorine atom and which may form a ring. In formula (B1), each f independently represents an integer of 0 to 4. In formula (B1), each g independently represents an integer of 1 to 4. In formula (B1), Rf １ each independently represents a monovalent or divalent substituent having one or more carbon atoms and containing three or more fluorine atoms.

[0037] Preferred embodiment of formula (B1) In the above formula (B1), Rf １ Of the carbon atoms forming the alkylene group, the proportion of carbon atoms directly bonded to fluorine atoms is preferably 30% or more, more preferably 40% or more, even more preferably 50% or more, even more preferably 60% or more, and particularly preferably 70% or more.

[0038] Rf １ The molecular structure represented by Rf is not particularly limited, and may be linear, branched, or cyclic. １ Examples of molecular structures that provide the above formula include linear, branched, or cyclic alkyl groups, and linear, branched, or cyclic alkenyl groups. Cyclic alkyl groups or cyclic alkenyl groups also include those in which a hydrogen atom bonded to a cyclic carbon atom is substituted with an alkyl group or an alkenyl group. The alkyl group or alkenyl group bonded to the cyclic carbon atom preferably has 1 to 6 carbon atoms. Such cyclic alkyl groups or cyclic alkenyl groups may be monovalent groups generated upon removal of one hydrogen atom bonded to a cyclic carbon atom, or may be monovalent groups generated upon removal of one hydrogen atom from the alkyl group or alkenyl group bonded to the cyclic carbon atom (i.e., cycloalkylalkyl group, cycloalkylalkenyl group, cycloalkenylalkyl group, or cycloalkenylalkenyl group).

[0039] Rf １is a fluoroalkyl group, examples of the alkyl group that gives the fluoroalkyl group include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, alkyl groups that are structurally isomeric with these alkyl groups, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 1-methylcyclopentyl group, a cyclopentylmethyl group, a cyclohexyl group, and an adamantyl group. Of these groups, in terms of excellent metal patterning performance, a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, alkyl groups that are structurally isomeric with these alkyl groups, and a cyclohexyl group are preferred. In this specification, the expression "giving (a group)" refers to a structural element that constitutes each substituent (a group), etc., and each element does not necessarily have to be a synthetic raw material for each substituent, etc.

[0040] Rf １ is a fluoroalkoxy group, examples of the alkoxy group that gives the fluoroalkoxy group include alkoxy groups in which the alkyl group that gives the fluoroalkyl group is bonded to the oxygen atom. Among these alkoxy groups, alkoxy groups in which a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, or an alkyl group that is structurally isomerized to these alkyl groups is preferred in terms of excellent metal patterning performance.

[0041] Rf １is a fluoroalkenyl group, examples of the alkenyl group that provides the fluoroalkenyl group include a vinyl group, a 1-propenyl group, a 1-butenyl group, a 1-pentynyl group, a 1-hexenyl group, alkenyl groups that are structurally isomeric with these alkenyl groups, a 1-cyclopropenyl group, a 1-cyclobutenyl group, a 1-cyclopentynyl group, a 1-cyclohexyl group, and cycloalkenyl groups that are structurally isomeric with these cycloalkenyl groups. Of these groups, in terms of excellent metal patterning performance, a vinyl group, a 1-propenyl group, a 1-butenyl group, a 1-pentynyl group, a 1-hexenyl group, alkenyl groups that are structurally isomeric with these alkenyl groups, a 1-cyclopentynyl group, and a 1-cyclohexyl group are preferred.

[0042] Rf １ is a fluoroalkenyloxy group, examples of the alkenyloxy group that provides the fluoroalkenyloxy group include alkenyloxy groups in which the alkenyl group that provides the fluoroalkenyl group is bonded to an oxygen atom. Among these alkenyloxy groups, alkenyloxy groups in which a vinyl group, a 1-propenyl group, a 1-butenyl group, a 1-pentynyl group, a 1-hexenyl group, an alkenyl group that is structurally isomerized to these alkenyl groups, a 1-cyclopentynyl group, or a 1-cyclohexyl group is bonded to an oxygen atom are preferred, in terms of excellent metal patterning performance.

[0043] Rf １ More preferred are each independently a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an alkyl group structurally isomeric to these alkyl groups, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 1-methylcyclopentyl group, a cyclopentylmethyl group, a cyclohexyl group, and an adamantyl group, all of which contain three or more fluorine atoms.

[0044] In formula (B1), L ２are each independently a divalent aliphatic hydrocarbon group selected from the group consisting of O, S, methylene, ethylene, n-propylene, n-butylene, n-pentylene, n-hexylene, n-heptylene, n-octylene, alkylene groups structurally isomeric to these alkylene groups, cyclopropylene, cyclobutylene, cyclopentylene, 1-methylpentylene, cyclopentylmethyl, cyclohexylene, and adamantanediyl, which may be substituted with a fluorine atom, because they can suppress the formation of a metal film on the film surface. Each f is independently preferably 0 to 3, more preferably 0 to 2. Each g is independently preferably 1 to 3, more preferably 1 to 2. The number of carbon atoms in the structure represented by formula (B1) is preferably 1 or more and 36 or less, more preferably 1 or more and 30 or less, even more preferably 1 or more and 24 or less, even more preferably 1 or more and 20 or less, particularly preferably 1 or more and 16 or less, and especially more preferably 2 or more and 16 or less.

[0045] Specific examples of formula (B1) Formula (B1) can have, for example, the structures shown in (AAA1) to (AAA126) below. Note that the mark "*" used in the following structures indicates a binding site.

[0046]

[0047]

[0048]

[0049]

[0050]

[0051]

[0052]

[0053]

[0054] Z １ , Z ２In formula (A2), Z １ , Z ２ each independently represents an optionally substituted di- to tetravalent monocyclic, linked ring, or fused ring aromatic hydrocarbon group having 6 to 26 carbon atoms, an optionally substituted di- to tetravalent monocyclic, linked ring, or fused ring heteroaromatic group having 3 to 11 carbon atoms, an optionally substituted di- to tetravalent cyclic aliphatic hydrocarbon group having 3 to 18 carbon atoms, or an optionally substituted di- to tetravalent cyclic heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms.

[0055] Z １ , Z ２ The monocyclic, linked ring, or fused ring divalent to tetravalent aromatic hydrocarbon group represented by the formula (I) is preferably a structure in which phenyl or a plurality of benzene rings are linked or fused. １ , Z ２ The heteroaromatic group having a valence of 2 to 4, which is a single ring, a linked ring or a condensed ring, represented by the formula: １ , Z ２ The cyclic divalent to tetravalent heteroaliphatic hydrocarbon group represented by the formula (I) is preferably a 5-membered ring, a 6-membered ring, a 7-membered ring or a condensed ring thereof, in which the heteroatom is N, O or S. １ , Z ２ Compounds which provide a monocyclic, linked ring, or fused ring divalent to tetravalent aromatic hydrocarbon group represented by the formula (I) are each independently preferably benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, and compounds obtained by condensing these groups with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene.

[0056] Z １ , Z ２As compounds which provide a monocyclic, linked ring, or fused ring divalent to tetravalent heteroaromatic group represented by the formula (I), it is preferable to independently select from the group consisting of pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, benzofuran, benzothiophene, benzodioxin, thiazole, thiadiazole, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and benzothiazole.

[0057] Z １ , Z ２ Compounds which provide the cyclic divalent to tetravalent aliphatic hydrocarbon groups represented by the following formula (1) are each independently preferably adamantane, diamantane, norbornene, and cyclohexane.

[0058] Z １ , Z ２ Compounds that provide the cyclic divalent to tetravalent heteroaliphatic hydrocarbon group represented by the formula (I) are each independently preferably morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxine, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane.

[0059] Z １ , Z ２

[0047] Compounds that provide a monocyclic, linked ring, or fused ring divalent to tetravalent aromatic hydrocarbon group represented by the formula (I) are each independently benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, and any of these groups fused with benzene or naphthalene.

[0060] Z １ , Z ２

[0043] Compounds which provide a monocyclic, linked ring, or fused ring divalent to tetravalent heteroaromatic group represented by the formula (I) are each independently pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, benzofuran, benzothiophene, benzodioxin, thiazole, thiadiazole, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and benzothiazole.

[0061] Z １ , Z ２ More preferred compounds which provide the cyclic divalent to tetravalent aliphatic hydrocarbon group represented by the following formula (1) are each independently adamantane, diamantane, norbornene, and cyclohexane.

[0062] Z １ , Z ２ More preferred compounds that provide the cyclic divalent to tetravalent heteroaliphatic hydrocarbon group represented by the formula (I) are, independently, morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxine, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane.

[0063] Z １ , Z ２

[0047] As compounds which provide a monocyclic, linked ring, or fused ring divalent to tetravalent aromatic hydrocarbon group represented by the formula (I), benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, and dibenzochrysene are even more preferred.

[0064] Z １ , Z ２

[0043] Compounds that provide a monocyclic, linked ring, or fused ring divalent to tetravalent heteroaromatic group represented by the formula (I) are each independently pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, benzofuran, benzothiophene, benzodioxin, thiazole, thiadiazole, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and benzothiazole.

[0065] Z １ , Z ２ As compounds which provide the cyclic divalent to tetravalent aliphatic hydrocarbon group represented by the following formula (1), adamantane, diamantane, norbornene, and cyclohexane are particularly preferred.

[0066] Z １ , Z ２ As compounds which provide the cyclic divalent to tetravalent heteroaliphatic hydrocarbon group represented by the formula (I), morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxine, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane are particularly preferred.

[0067] Z １ , Z ２ As compounds which provide a monocyclic, linked ring, or fused ring divalent to tetravalent aromatic hydrocarbon group represented by the formula (I), benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, benzochrysene, and triptycene are particularly preferred.

[0068] Z １ , Z ２As compounds which provide a monocyclic, linked ring, or fused ring divalent to tetravalent heteroaromatic group represented by the formula (I), pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, benzofuran, benzothiophene, benzodioxin, thiazole, thiadiazole, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and benzothiazole are particularly preferred.

[0069] Z １ , Z ２ As compounds which provide the cyclic divalent to tetravalent aliphatic hydrocarbon groups represented by the following formula (1), adamantane, diamantane, and cyclohexane are most preferred.

[0070] Z １ , Z ２ As compounds which provide the cyclic divalent to tetravalent heteroaliphatic hydrocarbon group represented by the formula (I), piperazine, homopiperazine, hexahydro-1,3,5-triazine, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane are most preferred.

[0071] Z １ , Z ２ The monocyclic, linked ring, or fused ring divalent to tetravalent aromatic hydrocarbon group represented by the formula (I) has 6 to 26 carbon atoms. The number of carbon atoms is preferably 6 to 24, more preferably 6 to 18, even more preferably 6 to 14, and even more preferably 6 to 12.

[0072] Z １ , Z ２ The monocyclic, linked ring, or fused ring divalent to tetravalent heteroaromatic group represented by the formula (I) has 3 to 11 carbon atoms. The number of carbon atoms is preferably 3 to 10, and more preferably 3 to 9.

[0073] Z １ , Z ２ The cyclic divalent to tetravalent aliphatic hydrocarbon group represented by the formula (I) has 3 to 18 carbon atoms. The number of carbon atoms is preferably 3 to 16, more preferably 3 to 14, even more preferably 3 to 12, and even more preferably 3 to 10.

[0074] Z １ , Z ２ The cyclic divalent to tetravalent heteroaliphatic hydrocarbon group represented by the formula (I) has 3 to 18 carbon atoms. The number of carbon atoms is preferably 3 to 14, more preferably 3 to 12, even more preferably 3 to 10, still more preferably 3 to 9, and most preferably 3 to 8.

[0075] Z １ , Z ２ are each independently preferably an optionally substituted monocyclic, linked ring or fused ring di- to tetravalent aromatic hydrocarbon group, an optionally substituted cyclic di- to tetravalent aliphatic hydrocarbon group, or an optionally substituted cyclic di- to tetravalent heteroaliphatic hydrocarbon group, more preferably an optionally substituted monocyclic, linked ring or fused ring di- to tetravalent aromatic hydrocarbon group, or an optionally substituted cyclic di- to tetravalent heteroaliphatic hydrocarbon group, and even more preferably an optionally substituted cyclic di- to tetravalent heteroaliphatic hydrocarbon group. １ , Z ２ are each independently preferably divalent or trivalent, more preferably divalent.

[0076] Z １ , Z ２ In the above formula (A2), Z １ , Z ２ When (at least one of) has a substituent, the substituent (hereinafter referred to as "Z １ , Z ２ As the substituents (B1), it is preferable that each of them is independently a linear, branched (branched chain), or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, a structure represented by the above formula (B1), or a structure in which these groups are further substituted with one or more groups selected from the group consisting of these groups (substituents).

[0077] Said Z １ , Z ２Examples of the substituents on each independently include a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, a structure represented by the above formula (B1), and a structure in which these groups are further substituted with one or more groups selected from the group consisting of these groups.

[0078] Said Z １ , Z ２ The substituents on each of the formula (B1) are preferably each independently a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, a structure represented by the formula (B1) above, or a structure in which these groups are further substituted with one or more groups selected from the group consisting of these groups.

[0079] Said Z １ , Z ２ The substituents are each independently preferably a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, a structure represented by formula (B1), or a structure in which these groups are further substituted with one or more groups selected from the group consisting of these groups.

[0080] Said Z １ , Z ２The substituents are each independently a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, a structure represented by the above formula (B1), or a structure in which these groups are further substituted with one or more groups selected from the group consisting of these groups.

[0081] Z １ , Z ２ Specific examples of the formula (A2) １ , Z ２ Examples of such structures include the structures shown below in (AAB1) to (AAB561). The mark "*" used in the above structures indicates a bonding site. F represents a fluorine atom, Rf represents a structure represented by formula (B1), v represents an integer of 0 to 5, w represents an integer of 0 to 4, x represents an integer of 0 to 3, y represents an integer of 0 to 2, and z represents an integer of 0 to 1.

[0082]

[0083]

[0084]

[0085]

[0086]

[0087]

[0088]

[0089]

[0090]

[0091]

[0092]

[0093]

[0094]

[0095]

[0096]

[0097]

[0098]

[0099]

[0100]

[0101]

[0102]

[0103]

[0104] G １ , G ２ In formula (A2), G １ Each of G independently represents an optionally substituted pyridyl group or an optionally substituted pyrimidyl group. ２ Each of G independently represents an optionally substituted pyridyl group, an optionally substituted pyrimidyl group, or an optionally substituted triazyl group. ２ Preferably, each of G is independently an optionally substituted pyridyl group or an optionally substituted pyrimidyl group. １ When G is an optionally substituted pyridyl group, at least one G ２ is more preferably an optionally substituted pyridyl group (i.e., G １ and G ２ and preferably the same group), and one or more G １ When G is an optionally substituted pyrimidyl group, at least one G ２ More preferably, is an optionally substituted pyrimidyl group.

[0105] G １ , G ２ In the above formula (A2), when at least one of the following (a) or (b) is present, (a) G １ is a substituted pyridyl group or a substituted pyrimidyl group; (b) G ２is a substituted pyridyl group, a substituted pyrimidyl group, or a substituted triazyl group. The substituents of these (a) and (b) are each independently preferably a linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, or a structure represented by the above formula (B1).

[0106] G １ , G ２ The substituents on each of the above are each independently preferably a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, and a structure represented by the above formula (B1), and these substituents may be further substituted with one or more groups selected from the group consisting of these groups.

[0107] G １ , G ２ The substituents on each of the above are each independently a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, and a structure represented by the above formula (B1), and these groups may be further substituted with one or more groups selected from the group consisting of these groups.

[0108] G １ , G ２The substituents on each of the above are each independently preferably a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, a thiazolyl group, and a structure represented by the above formula (B1), and these groups may be further substituted with one or more groups selected from the group consisting of these groups.

[0109] G １ , G ２ As the substituents of the formula (B1), it is most preferable that they are each independently a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 1 to 10 carbon atoms and substituted with one or more fluorine atoms, an alkoxy group having 1 to 10 carbon atoms and substituted with one or more fluorine atoms, a structure represented by formula (B1), and a fluorine atom.

[0110] L １ In formula (A2), L １ represents an optionally substituted monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group having 6 to 26 carbon atoms, an optionally substituted monocyclic, linked ring, or fused ring divalent heteroaromatic group having 3 to 26 carbon atoms, an optionally substituted cyclic divalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, an optionally substituted cyclic divalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, or a single bond.

[0111] L １ The monocyclic, linked ring, or condensed ring divalent aromatic hydrocarbon group represented by the formula (I) is preferably a phenyl group or a structure in which a plurality of benzene rings are linked or condensed.

[0112] L １ The monocyclic, linked ring, or condensed ring divalent heteroaromatic group represented by the formula (I) is preferably a 5-membered ring, a 6-membered ring, or a structure in which a heteroatom is N, O, or S and a plurality of benzene rings are condensed.

[0113] L １ The cyclic divalent heteroaliphatic hydrocarbon group represented by the formula (I) is preferably a 5-, 6-, or 7-membered ring or a condensed ring structure thereof, in which the heteroatom is N, O, or S.

[0114] L１ More preferred compounds that provide a monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group represented by the formula (I) are each independently benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, and dibenzochrysene, as well as these groups fused with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene.

[0115] L １

[0043] Compounds that provide a monocyclic, linked ring, or fused ring divalent heteroaromatic group represented by the formula (I) are each independently pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and benzothiazole, as well as those groups fused with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene, are more preferred.

[0116] L １ As compounds which provide a cyclic divalent aliphatic hydrocarbon group represented by the following formula (1), adamantane, diamantane, norbornene, and cyclohexane are more preferred.

[0117] L １ More preferred compounds that provide the cyclic divalent heteroaliphatic hydrocarbon group represented by the formula (I) are, independently, morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxine, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane.

[0118] L １

[0043] Compounds that provide a monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group represented by the formula (I) are each independently benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, and any of these groups fused with benzene or naphthalene.

[0119] L １ Compounds which provide a monocyclic, linked ring, or fused ring divalent heteroaromatic group represented by the formula (I) are each independently pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and these groups fused with benzene or naphthalene are more preferred.

[0120] L １ More preferred compounds that provide the cyclic divalent aliphatic hydrocarbon group represented by the formula (I) are each independently adamantane, diamantane, norbornene, and cyclohexane.

[0121] L １ More preferred compounds that provide the cyclic divalent heteroaliphatic hydrocarbon group represented by the formula (I) are, independently, morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxine, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane.

[0122] L １ As compounds which provide a monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group represented by the formula (I), benzene, biphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, and triphenylene are even more preferred.

[0123] L １

[0043] Compounds that provide a monocyclic, linked ring, or fused ring divalent heteroaromatic group represented by the formula (I) are each independently pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, acridine, dihydroacridine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and benzothiazole.

[0124] L １ As compounds which provide a cyclic divalent aliphatic hydrocarbon group represented by the following formula (1), adamantane, diamantane, and cyclohexane are even more preferred.

[0125] L １ As compounds which provide a cyclic divalent heteroaliphatic hydrocarbon group represented by the formula (I), piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxine, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane are even more preferred.

[0126] L １ As compounds which provide a monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group represented by the formula (I), benzene, biphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, and phenanthrene are most preferred.

[0127] L １ As compounds which provide a monocyclic, linked ring, or fused ring divalent heteroaromatic group represented by the formula (I), pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, acridine, dihydroacridine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and benzothiazole are most preferred.

[0128] L １ As compounds which provide the cyclic divalent aliphatic hydrocarbon group represented by the formula (I), adamantane, diamantane, and cyclohexane are most preferred.

[0129] L １ As compounds which provide a cyclic divalent heteroaliphatic hydrocarbon group represented by the formula (I), piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxine, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane are most preferred.

[0130] L １ The monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group represented by the formula (I) has 6 to 26 carbon atoms. The number of carbon atoms is preferably 6 to 24, more preferably 6 to 18, even more preferably 6 to 14, and even more preferably 6 to 12.

[0131] L １ The monocyclic, linked ring, or fused ring divalent heteroaromatic group represented by the formula (I) has 3 to 26 carbon atoms. The number of carbon atoms is preferably 6 to 24, more preferably 6 to 18, even more preferably 6 to 14, still more preferably 6 to 12, and most preferably 6 to 10.

[0132] L １The cyclic divalent aliphatic hydrocarbon group represented by the formula (I) has 3 to 18 carbon atoms. The number of carbon atoms is preferably 3 to 16, more preferably 3 to 14, even more preferably 3 to 12, and even more preferably 3 to 10.

[0133] L １ The cyclic divalent heteroaliphatic hydrocarbon group represented by the formula (I) has 3 to 18 carbon atoms. The number of carbon atoms is preferably 3 to 14, more preferably 3 to 12, even more preferably 3 to 10, still more preferably 3 to 9, and most preferably 3 to 8.

[0134] L １ are each independently preferably an optionally substituted monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group, an optionally substituted cyclic divalent aliphatic hydrocarbon group, an optionally substituted cyclic divalent heteroaliphatic hydrocarbon group, or a single bond; more preferably an optionally substituted monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group, an optionally substituted cyclic divalent heteroaliphatic hydrocarbon group, or a single bond; even more preferably an optionally substituted cyclic divalent heteroaliphatic hydrocarbon group, or a single bond; and even more preferably a single bond.

[0135] L １ In the above formula (A2), L １ When is a substituted (substituted) aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a cyclic heteroaliphatic hydrocarbon group, these substituents are preferably each independently a linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, or a structure represented by formula (B1).

[0136] L １The substituents of are each independently a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, and a structure represented by the above formula (B1), and these groups may be further substituted with one or more groups selected from the group consisting of these groups (substituents).

[0137] L １ The substituents on each of the above are each independently a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, and a structure represented by the above formula (B1), and these groups may be further substituted with one or more groups selected from the group consisting of these groups.

[0138] L １ The substituents on each of the above are each independently preferably a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, a thiazolyl group, and a structure represented by the above formula (B1), and these groups may be further substituted with one or more groups selected from the group consisting of these groups.

[0139] L １ As the substituents, each independently, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 1 to 10 carbon atoms and substituted with one or more fluorine atoms, an alkoxy group having 1 to 10 carbon atoms and substituted with one or more fluorine atoms, a structure represented by the above formula (B1), and a fluorine atom are most preferred.

[0140] L １ Specific examples of L １ As examples, the structures shown in (AAB1) to (AAB216) above can be used.

[0141] Preferred embodiments of a, b, c, d, and e In formula (A2), a, b, d, and e each independently represent an integer of 1 to 3. a and b each independently represent preferably 1 or 2, more preferably 1. d and e each independently represent preferably 1 or 2, more preferably 2. In formula (A2), c represents an integer of 0 to 2. c is preferably 0 or 1, more preferably 0.

[0142] The metal patterning material according to one embodiment of the present disclosure is a material capable of forming a thin film and is expected to have the effect of suppressing the formation of a metal thin film on a film surface. Furthermore, the metal patterning material may optionally contain other organic molecular materials, polymers, or the like, as long as the metal patterning material can suppress the formation of a metal film on the film surface.

[0143] The type of metal material to be patterned is not particularly limited, but alkali metals, alkaline earth metals, transition metals, or metals from Group 13 of the periodic table are preferred, including 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, and calcium-aluminum alloys, and examples of salts include lithium fluoride.

[0144] [Second Aspect: Heterocyclic Compound (A3)] A heterocyclic compound according to one aspect of the present disclosure is represented by the following formula (A3). In formula (A3), Y １ , Y ２ each independently represents an optionally substituted di- to tetravalent monocyclic, linked ring, or fused ring aromatic hydrocarbon group having 6 to 26 carbon atoms, an optionally substituted di- to tetravalent monocyclic, linked ring, or fused ring heteroaromatic group having 3 to 11 carbon atoms, an optionally substituted di- to tetravalent cyclic aliphatic hydrocarbon group having 3 to 18 carbon atoms, or an optionally substituted di- to tetravalent cyclic heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms.

[0145] In formula (A3), L ３ represents an optionally substituted monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group having 6 to 26 carbon atoms, an optionally substituted monocyclic, linked ring, or fused ring divalent heteroaromatic group having 3 to 26 carbon atoms, an optionally substituted cyclic divalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, an optionally substituted cyclic divalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, or a single bond. ３ Each of the groups independently represents an optionally substituted pyridyl group or an optionally substituted pyrimidyl group. ４ each independently represents an optionally substituted pyridyl group, an optionally substituted pyrimidyl group, or an optionally substituted triazyl group.

[0146] In formula (A3), h and i each independently represent an integer of 1 to 3. In formula (A3), k and m each independently represent 2 or 3. In formula (A3), j represents an integer of 0 to 2.

[0147] In formula (A3), R ３ and R ４ are each independently represented by the following formula (B2). In formula (B2), L ４represents O, S, a linear, branched or cyclic divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may be substituted with a fluorine atom, or a vinylene group which may be substituted with a fluorine atom and which may form a ring. In formula (B2), each n independently represents an integer of 0 to 4. In formula (B2), each p independently represents an integer of 1 to 4. In formula (B2), Rf ２ each independently represents a monovalent or divalent substituent having one or more carbon atoms and containing three or more fluorine atoms.

[0148] Preferred embodiment of formula (B2) In the above formula (B2), Rf ２ Of the carbon atoms forming the alkylene group, the proportion of carbon atoms directly bonded to fluorine atoms is preferably 30% or more, more preferably 40% or more, even more preferably 50% or more, even more preferably 60% or more, and particularly preferably 70% or more.

[0149] Rf ２ The molecular structure represented by Rf is not particularly limited, and may be linear, branched, or cyclic. ２ Examples of molecular structures that provide the above formula include linear, branched, or cyclic alkyl groups, and linear, branched, or cyclic alkenyl groups. Cyclic alkyl groups or cyclic alkenyl groups also include those in which a hydrogen atom bonded to a cyclic carbon atom is substituted with an alkyl group or an alkenyl group. The alkyl group or alkenyl group bonded to the cyclic carbon atom preferably has 1 to 6 carbon atoms. Such cyclic alkyl groups or cyclic alkenyl groups may be monovalent groups generated upon removal of one hydrogen atom bonded to a cyclic carbon atom, or may be monovalent groups generated upon removal of one hydrogen atom from the alkyl group or alkenyl group bonded to the cyclic carbon atom (i.e., cycloalkylalkyl group, cycloalkylalkenyl group, cycloalkenylalkyl group, or cycloalkenylalkenyl group).

[0150] Rf ２is a fluoroalkyl group, examples of the alkyl group that gives the fluoroalkyl group include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, alkyl groups that are structurally isomeric to these alkyl groups, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 1-methylcyclopentyl group, a cyclopentylmethyl group, a cyclohexyl group, an adamantyl group, etc. Among these groups, the methyl group, the ethyl group, the n-propyl group, the n-butyl group, the n-pentyl group, the n-hexyl group, alkyl groups that are structurally isomeric to these alkyl groups, and the cyclohexyl group are preferred in terms of excellent metal patterning performance.

[0151] Rf ２ is a fluoroalkoxy group, examples of the alkoxy group that gives the fluoroalkoxy group include alkoxy groups in which the alkyl group that gives the fluoroalkyl group is bonded to the oxygen atom. Among these alkoxy groups, alkoxy groups in which a methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, or an alkyl group that is structurally isomerized to these alkyl groups is preferred in terms of excellent metal patterning performance.

[0152] Rf ２ is a fluoroalkenyl group, examples of the alkenyl group that provides the fluoroalkenyl group include a vinyl group, a 1-propenyl group, a 1-butenyl group, a 1-pentynyl group, a 1-hexenyl group, alkenyl groups that are structurally isomeric with these alkenyl groups, a 1-cyclopropenyl group, a 1-cyclobutenyl group, a 1-cyclopentynyl group, a 1-cyclohexyl group, and cycloalkenyl groups that are structurally isomeric with these cycloalkenyl groups. Of these groups, in terms of excellent metal patterning performance, a vinyl group, a 1-propenyl group, a 1-butenyl group, a 1-pentynyl group, a 1-hexenyl group, alkenyl groups that are structurally isomeric with these alkenyl groups, a 1-cyclopentynyl group, and a 1-cyclohexyl group are preferred.

[0153] Rf ２is a fluoroalkenyloxy group, examples of the alkenyloxy group that provides the fluoroalkenyloxy group include alkenyloxy groups in which the alkenyl group that provides the fluoroalkenyl group is bonded to an oxygen atom. Among these alkenyloxy groups, alkenyloxy groups in which a vinyl group, a 1-propenyl group, a 1-butenyl group, a 1-pentynyl group, a 1-hexenyl group, an alkenyl group that is structurally isomerized to these alkenyl groups, a 1-cyclopentynyl group, or a 1-cyclohexyl group is bonded to an oxygen atom are preferred, in terms of excellent metal patterning performance.

[0154] Rf ２ More preferred are each independently a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an alkyl group structurally isomeric to these alkyl groups, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 1-methylcyclopentyl group, a cyclopentylmethyl group, a cyclohexyl group, and an adamantyl group, all of which contain three or more fluorine atoms.

[0155] In formula (B2), L ４ are each independently a divalent aliphatic hydrocarbon group selected from the group consisting of O, S, methylene, ethylene, n-propylene, n-butylene, n-pentylene, n-hexylene, n-heptylene, n-octylene, alkylene groups structurally isomeric to these alkylene groups, cyclopropylene, cyclobutylene, cyclopentylene, 1-methylpentylene, cyclopentylmethyl, cyclohexylene, and adamantanediyl, which may be substituted with a fluorine atom, because they can suppress the formation of a metal film on the film surface. Each n is independently preferably 0 to 3, more preferably 0 to 2. Each p is independently preferably 1 to 3, more preferably 1 to 2.

[0156] The number of carbon atoms in the structure represented by formula (B2) is preferably 1 or more and 36 or less, more preferably 1 or more and 30 or less, even more preferably 1 or more and 24 or less, even more preferably 1 or more and 20 or less, particularly preferably 1 or more and 16 or less, and especially more preferably 2 or more and 16 or less.

[0157] Specific Examples of Formula (B2) Formula (B2) can have, for example, the structures shown in (AAA1) to (AAA126) above.

[0158] Y １ , Y ２ In formula (A2), Y １ , Y ２ each independently represents an optionally substituted di- to tetravalent monocyclic, linked ring, or fused ring aromatic hydrocarbon group having 6 to 26 carbon atoms, an optionally substituted di- to tetravalent monocyclic, linked ring, or fused ring heteroaromatic group having 3 to 11 carbon atoms, an optionally substituted di- to tetravalent cyclic aliphatic hydrocarbon group having 3 to 18 carbon atoms, or an optionally substituted di- to tetravalent cyclic heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms.

[0159] Y １ , Y ２ The monocyclic, linked ring, or condensed ring divalent to tetravalent aromatic hydrocarbon group represented by the formula (I) is preferably a structure in which phenyl or multiple benzene rings are linked or condensed. １ , Y ２ The heteroaromatic group having a valence of 2 to 4, which is a single ring, a linked ring or a condensed ring, represented by the formula (I), preferably has a heteroatom of N, O or S, and has a 5-membered ring, a 6-membered ring or a condensed structure thereof. １ , Y ２ The cyclic divalent to tetravalent heteroaliphatic hydrocarbon group represented by the formula (I) is preferably a 5-, 6-, or 7-membered ring or a condensed ring structure thereof, in which the heteroatom is N, O, or S.

[0160] Y １ , Y ２Compounds which provide a monocyclic, linked ring, or fused ring divalent to tetravalent aromatic hydrocarbon group represented by the formula (I) are each independently preferably benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, and compounds obtained by condensing these groups with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene.

[0161] Y １ , Y ２

[0043] Compounds that provide a monocyclic, linked ring, or fused ring divalent to tetravalent heteroaromatic group represented by the formula (I) are preferably at least one selected from the group consisting of pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, benzofuran, benzothiophene, benzodioxin, thiazole, thiadiazole, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and benzothiazole.

[0162] Y １ , Y ２ Compounds which provide the cyclic divalent to tetravalent aliphatic hydrocarbon groups represented by the following formula (1) are each independently preferably adamantane, diamantane, norbornene, and cyclohexane.

[0163] Y １ , Y ２ Compounds that provide the cyclic divalent to tetravalent heteroaliphatic hydrocarbon group represented by the formula (I) are each independently preferably morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxine, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane.

[0164] Y １ , Y ２

[0047] Compounds that provide a monocyclic, linked ring, or fused ring divalent to tetravalent aromatic hydrocarbon group represented by the formula (I) are each independently benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, and any of these groups fused with benzene or naphthalene.

[0165] Y １ , Y ２ More preferred compounds that provide a monocyclic, linked ring, or fused ring divalent to tetravalent heteroaromatic group represented by the formula (I) are each independently pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, benzofuran, benzothiophene, benzodioxin, thiazole, thiadiazole, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and benzothiazole.

[0166] Y １ , Y ２ More preferred compounds which provide the cyclic divalent to tetravalent aliphatic hydrocarbon group represented by the following formula (1) are each independently adamantane, diamantane, norbornene, and cyclohexane.

[0167] Y １ , Y ２ More preferred compounds that provide the cyclic divalent to tetravalent heteroaliphatic hydrocarbon group represented by the formula (I) are, independently, morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxine, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane.

[0168] Y １ , Y ２

[0047] As compounds which provide a monocyclic, linked ring, or fused ring divalent to tetravalent aromatic hydrocarbon group represented by the formula (I), benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, and dibenzochrysene are even more preferred.

[0169] Y １ , Y ２

[0043] Compounds that provide a monocyclic, linked ring, or fused ring divalent to tetravalent heteroaromatic group represented by the formula (I) are each independently pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, benzofuran, benzothiophene, benzodioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and benzothiazole.

[0170] Y １ , Y ２ As compounds which provide the cyclic divalent to tetravalent aliphatic hydrocarbon group represented by the following formula (1), adamantane, diamantane, norbornene, and cyclohexane are particularly preferred.

[0171] Y １ , Y ２ As compounds which provide the cyclic divalent to tetravalent heteroaliphatic hydrocarbon group represented by the formula (I), morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxine, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane are particularly preferred.

[0172] Y １ , Y ２As compounds which provide a monocyclic, linked ring, or fused ring divalent to tetravalent aromatic hydrocarbon group represented by the formula (I), benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, benzochrysene, and triptycene are particularly preferred.

[0173] Y １ , Y ２ As compounds which provide a monocyclic, linked ring, or fused ring divalent to tetravalent heteroaromatic group represented by the formula (I), pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, benzofuran, benzothiophene, benzodioxin, thiazole, thiadiazole, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and benzothiazole are particularly preferred.

[0174] Y １ , Y ２ As compounds which provide the cyclic divalent to tetravalent aliphatic hydrocarbon groups represented by the following formula (1), adamantane, diamantane, and cyclohexane are most preferred.

[0175] Y １ , Y ２ As compounds which provide the cyclic divalent to tetravalent heteroaliphatic hydrocarbon group represented by the formula (I), piperazine, homopiperazine, hexahydro-1,3,5-triazine, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane are most preferred.

[0176] Y １ , Y ２ The monocyclic, linked ring, or fused ring divalent to tetravalent aromatic hydrocarbon group represented by the formula (I) has 6 to 26 carbon atoms. The number of carbon atoms is preferably 6 to 24, more preferably 6 to 18, even more preferably 6 to 14, and even more preferably 6 to 12.

[0177] Y１ , Y ２ The monocyclic, linked ring, or fused ring divalent to tetravalent heteroaromatic group represented by the formula (I) has 3 to 11 carbon atoms. The number of carbon atoms is preferably 3 to 10, and more preferably 3 to 9.

[0178] Y １ , Y ２ The cyclic divalent to tetravalent aliphatic hydrocarbon group represented by the formula (I) has 3 to 18 carbon atoms. The number of carbon atoms is preferably 3 to 16, more preferably 3 to 14, even more preferably 3 to 12, and even more preferably 3 to 10.

[0179] Y １ , Y ２ The cyclic divalent to tetravalent heteroaliphatic hydrocarbon group represented by the formula (I) has 3 to 18 carbon atoms. The number of carbon atoms is preferably 3 to 14, more preferably 3 to 12, even more preferably 3 to 10, still more preferably 3 to 9, and most preferably 3 to 8.

[0180] Y １ , Y ２ are each independently preferably an optionally substituted monocyclic, linked ring or fused ring di- to tetravalent aromatic hydrocarbon group, an optionally substituted cyclic di- to tetravalent aliphatic hydrocarbon group, or an optionally substituted cyclic di- to tetravalent heteroaliphatic hydrocarbon group, more preferably an optionally substituted monocyclic, linked ring or fused ring di- to tetravalent aromatic hydrocarbon group, or an optionally substituted cyclic di- to tetravalent heteroaliphatic hydrocarbon group, and even more preferably an optionally substituted cyclic di- to tetravalent heteroaliphatic hydrocarbon group. １ , Y ２ are each independently preferably divalent or trivalent, more preferably divalent.

[0181] Y １ , Y ２ In the above formula (A3), Y １ , Y ２ When (at least one of) has a substituent, the substituent (hereinafter referred to as "Y １ , Y ２As the substituents (B1 and B2), it is preferable that each of them is independently a linear, branched (branched chain), or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, a structure represented by the above formula (B2), or a structure in which these groups are further substituted with one or more groups selected from the group consisting of these groups (substituents).

[0182] The Y １ , Y ２ Examples of the substituents in the formula (B2) are each independently a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, a structure represented by the above formula (B2), and a structure in which these groups are further substituted with one or more groups selected from the group consisting of these groups.

[0183] The Y １ , Y ２ The substituents on each of the formula (B1) and (B2) are preferably each independently a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, a structure represented by the above formula (B2), or a structure in which these groups are further substituted with one or more groups selected from the group consisting of these groups.

[0184] The Y １ , Y ２The substituents are each independently preferably a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, a structure represented by formula (B2), or a structure in which these groups are further substituted with one or more groups selected from the group consisting of these groups.

[0185] The Y １ , Y ２ The substituents are each independently a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, a structure represented by the above formula (B2), or a structure in which these groups are further substituted with one or more groups selected from the group consisting of these groups.

[0186] Y １ , Y ２ Specific examples of the formula (A3) １ , Y ２ Examples of such compounds include the structures shown in (AAB1) to (AAB561) above.

[0187] G ３ , G ４ In formula (A3), G ３ Each of the groups independently represents an optionally substituted pyridyl group or an optionally substituted pyrimidyl group. ４ Each of G independently represents an optionally substituted pyridyl group, an optionally substituted pyrimidyl group, or an optionally substituted triazyl group. ４ Preferably, each of G is independently an optionally substituted pyridyl group or an optionally substituted pyrimidyl group. ３ When G is an optionally substituted pyridyl group, at least one G ４ is more preferably an optionally substituted pyridyl group (i.e., G ３ and G ４ and preferably the same group), and one or more G３ When G is an optionally substituted pyrimidyl group, at least one G ４ More preferably, is an optionally substituted pyrimidyl group.

[0188] G ３ , G ４ In the above formula (A3), when at least one of the following (a) or (b) is present, (a) G ３ is a substituted pyridyl group or a substituted pyrimidyl group; (b) G ４ is a substituted pyridyl group, a substituted pyrimidyl group, or a substituted triazyl group. The substituents in (a) and (b) are each independently preferably a linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, or a structure represented by the above formula (B2).

[0189] G ３ , G ４ The substituents on each of the above are each independently preferably a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, and a structure represented by the above formula (B2), and these substituents may be further substituted with one or more groups selected from the group consisting of these groups.

[0190] G ３ , G ４More preferred substituents on each of the above are independently a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, and a structure represented by the above formula (B2), and these groups may be further substituted with one or more groups selected from the group consisting of these groups.

[0191] G ３ , G ４ The substituents on each of the above are each independently preferably a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, a thiazolyl group, and a structure represented by the above formula (B2), and these groups may be further substituted with one or more groups selected from the group consisting of these groups.

[0192] G ３ , G ４ As the substituents of the formula (B1), it is most preferable that the substituents are each independently a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 1 to 10 carbon atoms and substituted with one or more fluorine atoms, an alkoxy group having 1 to 10 carbon atoms and substituted with one or more fluorine atoms, a structure represented by formula (B2), and a fluorine atom.

[0193] L ３ A preferred embodiment of L ３ The monocyclic, linked ring, or condensed ring divalent aromatic hydrocarbon group represented by the formula (I) is preferably a phenyl group or a structure in which a plurality of benzene rings are linked or condensed. ３ The monocyclic, linked ring, or condensed ring divalent heteroaromatic group represented by the formula (I) preferably has a heteroatom of N, O, or S, and a five-membered ring, a six-membered ring, or a structure in which a plurality of benzene rings are condensed. ３The cyclic divalent heteroaliphatic hydrocarbon group represented by the formula (I) is preferably a 5-, 6-, or 7-membered ring or a condensed ring structure thereof, in which the heteroatom is N, O, or S.

[0194] L ３ More preferred compounds which provide a monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group represented by the formula (I) are each independently benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, and any of these groups fused with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene.

[0195] L ３

[0043] Compounds that provide a monocyclic, linked ring, or fused ring divalent heteroaromatic group represented by the formula (I) are each independently pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and compounds in which one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene are fused to these groups are more preferred.

[0196] L ３ As compounds which provide a cyclic divalent aliphatic hydrocarbon group represented by the following formula (1), adamantane, diamantane, norbornene, and cyclohexane are more preferred.

[0197] L ３More preferred compounds that provide the cyclic divalent heteroaliphatic hydrocarbon group represented by the formula (I) are, independently, morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxine, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane.

[0198] L ３

[0043] Compounds that provide a monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group represented by the formula (I) are each independently benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, and dibenzochrysene, as well as any of these groups fused with benzene or naphthalene.

[0199] L ３

[0043] Compounds that provide a monocyclic, linked ring, or fused ring divalent heteroaromatic group represented by the formula (I) are each independently pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and benzothiazole, as well as those groups fused with benzene or naphthalene, are more preferred.

[0200] L ３ More preferred compounds that provide the cyclic divalent aliphatic hydrocarbon group represented by the formula (I) are each independently adamantane, diamantane, norbornene, and cyclohexane.

[0201] L ３More preferred compounds that provide the cyclic divalent heteroaliphatic hydrocarbon group represented by the formula (I) are, independently, morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxine, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane.

[0202] L ３ As compounds which provide a monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group represented by the formula (I), benzene, biphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, and triphenylene are even more preferred.

[0203] L ３

[0043] Compounds that provide a monocyclic, linked ring, or fused ring divalent heteroaromatic group represented by the formula (I) are each independently pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, acridine, dihydroacridine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and benzothiazole.

[0204] L ３ As compounds which provide a cyclic divalent aliphatic hydrocarbon group represented by the following formula (1), adamantane, diamantane, and cyclohexane are even more preferred.

[0205] L ３As compounds which provide a cyclic divalent heteroaliphatic hydrocarbon group represented by the formula (I), piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxine, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane are even more preferred.

[0206] L ３ As compounds which provide a monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group represented by the formula (I), benzene, biphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, and phenanthrene are most preferred.

[0207] L ３ As compounds which provide a monocyclic, linked ring, or fused ring divalent heteroaromatic group represented by the formula (I), pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, acridine, dihydroacridine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and benzothiazole are most preferred.

[0208] L ３ As compounds which provide the cyclic divalent aliphatic hydrocarbon group represented by the formula (I), adamantane, diamantane, and cyclohexane are most preferred.

[0209] L ３ As compounds which provide a cyclic divalent heteroaliphatic hydrocarbon group represented by the formula (I), piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxine, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane are most preferred.

[0210] L ３ The monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group represented by the formula (I) has 6 to 26 carbon atoms. The number of carbon atoms is preferably 6 to 24, more preferably 6 to 18, even more preferably 6 to 14, and even more preferably 6 to 12.

[0211] L ３ The monocyclic, linked ring, or fused ring divalent heteroaromatic group represented by the formula (I) has 3 to 26 carbon atoms. The number of carbon atoms is preferably 6 to 24, more preferably 6 to 18, even more preferably 6 to 14, still more preferably 6 to 12, and most preferably 6 to 10.

[0212] L ３ The cyclic divalent aliphatic hydrocarbon group represented by the formula (I) has 3 to 18 carbon atoms. The number of carbon atoms is preferably 3 to 16, more preferably 3 to 14, even more preferably 3 to 12, and even more preferably 3 to 10.

[0213] L ３ The cyclic divalent heteroaliphatic hydrocarbon group represented by the formula (I) has 3 to 18 carbon atoms. The number of carbon atoms is preferably 3 to 14, more preferably 3 to 12, even more preferably 3 to 10, still more preferably 3 to 10, and most preferably 3 to 8.

[0214] L ３ are each independently preferably an optionally substituted monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group, an optionally substituted cyclic divalent aliphatic hydrocarbon group, an optionally substituted cyclic divalent heteroaliphatic hydrocarbon group, or a single bond; more preferably an optionally substituted monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group, an optionally substituted cyclic divalent heteroaliphatic hydrocarbon group, or a single bond; even more preferably an optionally substituted cyclic divalent heteroaliphatic hydrocarbon group, or a single bond; and even more preferably a single bond.

[0215] L ３ In the above formula (A3), L ３When is a substituted (substituted) aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a cyclic heteroaliphatic hydrocarbon group, these substituents are preferably each independently a linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, or a structure represented by formula (B2).

[0216] L ３ The substituents of are each independently a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, and a structure represented by the above formula (B2), and these groups may be further substituted with one or more groups selected from the group consisting of these groups (substituents).

[0217] L ３ The substituents are each independently preferably a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, and a structure represented by the above formula (B2), and these groups may be further substituted with one or more groups selected from the group consisting of these groups.

[0218] L ３The substituents on each of the above are each independently preferably a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, a thiazolyl group, and a structure represented by the above formula (B2), and these groups may be further substituted with one or more groups selected from the group consisting of these groups.

[0219] L ３ As the substituents, each independently, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 1 to 10 carbon atoms and substituted with one or more fluorine atoms, an alkoxy group having 1 to 10 carbon atoms and substituted with one or more fluorine atoms, a structure represented by the above formula (B2), and a fluorine atom are most preferred.

[0220] L ３ Specific examples of L ３ As examples, the structures shown in (AAB1) to (AAB216) above can be used.

[0221] Preferred embodiments of h, i, j, k, and m In formula (A3), h and i each independently represent an integer of 1 to 3. h and i each independently represent preferably 1 or 2, more preferably 1. In formula (A3), k and m each independently represent an integer of 2 to 3. k and m each independently represent more preferably 2. In formula (A3), j represents an integer of 0 to 2. j is preferably 0 or 1, more preferably 0.

[0222] Specific examples of the compound represented by (A3) above: Examples of the material for metal patterning represented by (A2) above and the compound represented by (A3) according to one embodiment of the present disclosure include compounds of the following formulae (Z1) to (Z173), but the present disclosure is not limited to these compounds.

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233]

[0234]

[0235] [Thin Film for Metal Patterning] A thin film for metal patterning according to one aspect of the present disclosure includes the material for metal patterning and is capable of patterning a metal film or a metal laminate film.

[0236] The metal patterning material contains a compound represented by formula (A2), and the metal film or metal laminate film contains one or more metals selected from the group consisting of lithium, ytterbium, magnesium, silver, and aluminum, or an alloy containing one or more of these metals. The metal patterning material contained in the metal patterning thin film is the same as the metal patterning material containing the compound described above. The alloy contained in the metal film or metal laminate film is preferably a magnesium alloy or a silver alloy.

[0237] In one aspect of the present disclosure, the water contact angles of the metal patterning thin film are more preferably 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, in that order.

[0238] [Organic Electroluminescence Element] An organic electroluminescence element according to one aspect of the present disclosure is an organic electroluminescence element including a cathode, wherein the cathode contains one or more metals selected from the group consisting of lithium, ytterbium, magnesium, silver, and aluminum, or an alloy containing one or more of these metals, and the cathode is patterned with a metal patterning material, wherein the metal patterning material contains the compound represented by formula (A2). The organic electroluminescence element uses the same metal patterning material used for patterning as the above-described metal patterning material, which contains the compound represented by formula (A2).

[0239] [Metal Pattern Forming Method] A metal pattern forming method according to one embodiment of the present disclosure includes: forming an organic material pattern containing the above-described metal patterning material; and applying a metal material to a region where the organic material pattern is to be formed and a region where the organic material pattern is not formed, thereby forming a metal pattern in the region where the metal pattern is not formed. The metal patterning material is used by forming a film in a region where it is desired to suppress adhesion of the metal material. The region where it is desired to suppress adhesion of the metal material corresponds to a region where the organic material pattern is to be formed. Regions other than the region where it is desired to suppress adhesion of the metal material correspond to a region where the organic material pattern is not formed. The region where the organic material pattern is not formed is a region where adhesion of the metal material is promoted, and is a region where it is desired to form a metal pattern.

[0240] 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 deposition, offset deposition, spray coating, inkjet deposition, screen deposition, offset deposition, flexography, gravure deposition, and microcontact deposition can be used. After film formation, the film may be annealed in a temperature environment higher than room temperature. The film thickness of the organic material pattern is also not particularly limited.

[0241] 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. The base on which the organic material pattern is formed may be metallic or non-metallic, and examples thereof include organic films, metal films, oxide films, inorganic films, etc., and are not particularly limited. The material of the substrate is also not particularly limited, and glass, plastic, metal, ceramic, and any other material can be used.

[0242] 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. The type of metal material used to form a metal pattern using a metal patterning material is not particularly limited, but is preferably an alkali metal, alkaline earth metal, transition metal, or metal of Group 13 of the periodic table, and more preferably 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, or an alloy containing one or more selected from the group consisting of these metals. Examples of such alloys include a magnesium-silver alloy, a magnesium-indium alloy, a magnesium-aluminum alloy, an indium-silver alloy, a lithium-aluminum alloy, a lithium-magnesium alloy, a lithium-indium alloy, and a calcium-aluminum alloy.

[0243] 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. Furthermore, the film thickness of the metal pattern is also not particularly limited. 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 instantly formed in both regions. However, since the adhesion of the metal to the region where the organic material pattern is formed is suppressed, the metal pattern is naturally formed only in the region where the organic material pattern is not formed.

[0244] More specific methods for forming metal patterns include, for example, the following methods 1) and 2). 1) The above-described metal patterning material is vapor-deposited into a desired pattern using a metal mask or the like. 2) Thereafter, metal is vapor-deposited to form electrodes only in areas where the metal patterning material has not been deposited. In other words, a negative metal electrode is formed with respect to the deposition pattern of the metal patterning material.

[0245] 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.

[0246] A protective film may be provided on the patterned metal film. Examples of the protective film include organic films, oxide films, and inorganic films, and are not particularly limited. When the protective film is an organic film, examples of the organic film 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 copolymers, conductive polymer oligomers (especially thiophene oligomers), porphyrin compounds, aromatic tertiary amine compounds, carbazole compounds, styrylamine compounds, triazine derivatives, and pyrimidine derivatives. When the protective film is an inorganic film, examples of the inorganic film include silicon nitride and silicon oxide.

[0247] According to the metal patterning material and the metal pattern forming method according to one aspect 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 circuit boards.

[0248] The metal patterning material according to one embodiment of the present disclosure can also be applied to a vapor deposition process.

[0249] (Organic Electroluminescence Device) The configuration of the organic electroluminescence device is not particularly limited, and examples thereof include the following configurations (i) to (v): (i): anode / light-emitting layer / patterning layer / metal electrode (ii): anode / hole-transport layer / light-emitting layer / patterning layer / metal electrode (iii): anode / light-emitting layer / electron-transport layer / patterning layer / metal electrode (iv): anode / hole-transport layer / light-emitting layer / electron-transport layer / patterning layer / metal electrode (v): anode / hole-injection layer / hole-transport layer / light-emitting layer / electron-transport layer / patterning layer / metal electrode Note that although the organic electroluminescence device shown in FIG. 5 has a so-called top-emission device configuration, the organic electroluminescence device according to one embodiment of the present disclosure is not limited to a top-emission device configuration. In other words, the organic electroluminescence device according to one embodiment of the present disclosure may have another known device configuration, such as a bottom-emission type.

[0250] 5 is a schematic cross-sectional view showing an example of a layered structure of an organic electroluminescent device according to one embodiment of the present disclosure. The organic electroluminescent device 100 includes, in this order, a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, an emitting layer 5, an electron transport layer 6, a cathode patterning layer 50, and a protective layer 9. However, some of these layers, except for the cathode patterning layer 50, may be omitted, or other layers may be added. For example, a hole blocking layer may be provided between the emitting layer 5 and the electron transport layer 6, or the hole injection layer 3 may be omitted and the hole transport layer 4 may be provided directly on the anode 2. Furthermore, for example, the electron transport layer 6 may be omitted and the cathode patterning layer 50 may be provided directly on the emitting layer 5. Furthermore, for example, the single-layer hole transport layer 4 and the single-layer electron transport layer 6 may each be composed of multiple layers.

[0251] [Substrate 1] The substrate 1 is not particularly limited and may be, for example, a glass plate, a quartz plate, a plastic plate, a plastic film, etc. Among these, a glass plate, a quartz plate, or a light-transmitting plastic film is preferred.

[0252] Examples of light-transmitting plastic films include films made of polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC), cellulose triacetate (TAC), cellulose acetate propionate (CAP), etc. In a configuration in which light is extracted from the substrate 1 side, the substrate 1 is transparent to the wavelength of light.

[0253] [Anode 2] An anode 2 is provided on the substrate 1 (on the side of the hole injection layer 3). Materials for the anode include metals, alloys, electrically conductive compounds, and mixtures thereof, each having a large work function (for example, 4 eV or more). Specific examples of anode materials include metals such as Au; CuI; indium tin oxide (ITO); and SnO. ２In the case of an organic electroluminescent device configured so that light is extracted through the anode, the anode is formed of a conductive transparent material that is transparent or substantially transparent to the emitted light.

[0254] [Hole Injection Layer 3, Hole Transport Layer 4] Between the anode 2 and the light-emitting layer 5 described later, a hole injection layer 3 and a hole transport layer 4 are provided in this order from the anode 2 side. The hole injection layer and the hole transport layer have the function of transporting holes injected from the anode to the light-emitting layer. By interposing these hole injection layer and hole transport layer between the anode and the light-emitting layer, more holes are injected into the light-emitting layer at a lower electric field. The hole injection layer and the hole transport layer also function as electron barrier layers. That is, electrons injected from the cathode and transported from the electron injection layer and / or the electron transport layer to the light-emitting layer are prevented from leaking to the hole injection layer and / or the hole transport layer due to the electron barrier present at the interface between the light-emitting layer and the hole injection layer and / or the hole transport layer. As a result, the electrons accumulate at the interface within the light-emitting layer, resulting in effects such as improved light-emitting efficiency, and an organic electroluminescent device with excellent light-emitting performance is obtained.

[0255] Materials for the hole injection layer and hole transport layer have at least one of hole injection properties, hole transport properties, and electron barrier properties. The materials for the hole injection layer and hole transport layer may be either organic or inorganic. Specific examples of materials for the hole injection layer and hole transport layer include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers (particularly thiophene oligomers), porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds. Among these, porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds are preferred, with aromatic tertiary amine compounds being particularly preferred, due to their excellent performance in organic electroluminescent devices.

[0256] Specific examples of the aromatic tertiary amine compound and the styrylamine compound include N,N,N',N'-tetraphenyl-4,4'-diaminophenyl, N,N'-diphenyl-N,N'-bis(m-tolyl)-[1,1'-biphenyl]-4,4'-diamine (TPD), 2,2-bis(4-di-p-tolylaminophenyl)propane, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N,N',N'-tetra-p-tolyl-4,4'-diaminobiphenyl, 1,1-bis(4-di-p-tolylaminophenyl)-4-phenylcyclohexane, bis(4-dimethylamino-2-methylphenyl)phenylmethane, bis(4-di-p-tolylaminophenyl)phenylmethane, N,N'-diphenyl-N,N'- Examples thereof include di(4-methoxyphenyl)-4,4'-diaminobiphenyl, N,N,N',N'-tetraphenyl-4,4'-diaminodiphenyl ether, 4,4'-bis(diphenylamino)quadriphenyl, N,N,N-tri(p-tolyl)amine, 4-(di-p-tolylamino)-4'-[4-(di-p-tolylamino)styryl]stilbene, 4-N,N-diphenylamino-(2-diphenylvinyl)benzene, 3-methoxy-4'-N,N-diphenylaminostilbenzene, N-phenylcarbazole, 4,4'-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPD), and 4,4',4''-tris[N-(m-tolyl)-N-phenylamino]triphenylamine (MTDATA).

[0257] Further, examples of materials for the hole injection layer and the hole transport layer include inorganic compounds such as p-type Si and p-type SiC. The hole injection layer and the hole transport layer may have a single structure made of one or more materials, or may have a laminate structure made of multiple layers of the same composition or different compositions.

[0258] [Light-emitting layer 5] The light-emitting layer 5 is provided between the hole-transporting layer 4 and the electron-transporting layer 6 described below. Materials for the light-emitting layer include phosphorescent materials, fluorescent materials, and thermally activated delayed fluorescent materials. In the light-emitting layer, electron-hole pairs recombine, resulting in light emission. The light-emitting layer may be composed of a single low-molecular-weight material or a single polymer material, but more commonly is composed of a host material doped with a guest compound. Light emission is primarily generated by the dopant and can exhibit any color.

[0259] Examples of the host material include compounds having a biphenylyl group, a fluorenyl group, a triphenylsilyl group, a carbazole group, a pyrenyl group, and an anthryl group. More specific examples include DPVBi (4,4'-bis(2,2-diphenylvinyl)-1,1'-biphenyl), BCzVBi (4,4'-bis(9-ethyl-3-carbazovinylene)1,1'-biphenyl), TBADN (2-tertiarybutyl-9,10-di(2-naphthyl)anthracene), ADN (9,10-di(2-naphthyl)anthracene), CBP (4,4'-bis(carbazol-9-yl)biphenyl), CDBP (4,4'-bis(carbazol-9-yl)-2,2'-dimethylbiphenyl), 2-(9-phenylcarbazol-3-yl)-9-[4-(4-phenylphenylquinazolin-2-yl)carbazole, 9,10-bis(biphenyl)anthracene, 3-(10-phenyl-9-anthryl)-dibenzofuran, and the like.

[0260] Examples of fluorescent dopants include anthracene, pyrene, tetracene, xanthene, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyran compounds, thiopyran compounds, polymethine compounds, pyrylium, thiapyrylium compounds, fluorene derivatives, periflanthene derivatives, indenoperylene derivatives, bis(azinyl)amine boron compounds, bis(azinyl)methane compounds, carbostyril compounds, boron compounds, and cyclic amine compounds. The fluorescent dopant may be a combination of two or more selected from these. Examples of phosphorescent dopants include organometallic complexes of transition metals such as iridium, platinum, palladium, and osmium.

[0261] Specific examples of fluorescent dopants and phosphorescent dopants include Alq3 (tris(8-hydroxyquinoline)aluminum), DPAVBi (4,4'-bis[4-(di-p-tolylamino)styryl]biphenyl), perylene, 2,7-bis[N,N-di-(4-tert-butylphenyl)]amino-bisbenzofurano-9,9'-spirofluorene, bis[2-(4-n-hexylphenyl)quinoline](aluminum), and the like. Examples of such an emissive material include Ir(PPy)3 (tris(2-phenylpyridine)iridium(III)), Ir(PPy)3 (tris(2-phenylpyridine)iridium(III)), and FIrPic (bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(III)), 5,9-diphenyl-5,9-dihydro-5,9-diaza-13b-boranaphtho[3,2,1-de]anthracene). The emissive material is not limited to being contained only in the emissive layer. For example, the emissive material may be contained in a layer adjacent to the emissive layer (hole transport layer 4 or electron transport layer 6). This may further enhance the luminous efficiency of the organic electroluminescent device. The emissive layer may have a single-layer structure made of one or more materials, or a laminate structure made of multiple layers of the same or different compositions.

[0262] [Electron Transport Layer 6] The electron transport layer 6 is provided between the light-emitting layer 5 and a cathode patterning layer 50 described later. The electron transport layer has a function of transporting electrons injected from the cathode to the light-emitting layer. By interposing the electron transport layer between the cathode and the light-emitting layer, electrons are injected into the light-emitting layer at a lower electric field.

[0263] Specific examples of materials for the electron transport layer include tris(8-quinolinolato)aluminum derivatives, imidazole derivatives, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoline derivatives, quinoxaline derivatives, oxadiazole derivatives, phosphole derivatives, silole derivatives, and phosphine oxide derivatives. Among these, triazine derivatives and pyrimidine derivatives are preferred in terms of the good performance of the organic electroluminescent device. Furthermore, the electron transport layer may further contain one or more types selected from conventionally known electron transport materials in addition to the materials listed above.

[0264] [Cathode Patterning Layer 50] A cathode patterning layer 50 is provided between the electron transport layer 6 and a protective layer 9 described later. The cathode patterning layer 50 is provided on the electron transport layer 6 and includes a patterning layer 7 and an electrode metal 8 patterned by this patterning layer 7.

[0265] In the direction from the anode 2 toward the protective layer 9 in Fig. 6 , the region where the patterning layer 7 exists is a transparent region 51, and the region where the patterning layer 7 does not exist (i.e., electrode region 8) is an electrode region 52. Note that the direction from the anode 2 toward the protective layer 9 is the vertical upward direction with respect to the substrate 1 in Fig. 11 . In the transparent region 51 in Fig. 6 , the electron transport layer 6 and the pattern layer 7 are stacked in this order in the direction from the anode 2 toward the protective layer 9. The electron transport layer 6 and the pattern layer 7 are stacked in direct contact with each other.

[0266] 6 , the electrode region 52 includes an electron transport layer 6 and an electrode metal 8 stacked in this order in the direction from the anode 2 toward the protective layer 9. The electron transport layer 6 and the electrode metal 8 are stacked in direct contact with each other. Note that, although the patterning layer 7 and the electrode metal 8 are shown to have the same thickness in FIG. 6 , the present disclosure is not limited to this, and the patterning layer 7 may be thicker, or the electrode 8 may be thicker.

[0267] 7 is a schematic top view showing an example of the configuration of the cathode patterning layer 50 in FIG. 5. The electrode metal 8 is patterned by the patterning layer 7. The electrode metal 8 is preferably finely patterned. Here, finely patterned patterning includes patterning having a patterning interval similar to that of a cathode in a general organic electroluminescence element. The patterned shape of the electrode metal 8 is arbitrary, and the patterning layer 7 may be formed so that the shape of the electrode metal 8 is the desired shape.

[0268] [Patterning Layer 7] As the material for the patterning layer, the compounds represented by the formula (A2) or (A3) can be used.

[0269] [Electrode Metal 8] The electrode metal may have a single layer structure made of one or more materials, or may have a laminate structure made of multiple layers of the same or different compositions. For example, the electrode metal is preferably formed of two layers: a cathode having high conductivity and an electron injection layer having a function of transferring electrons injected from the cathode to the light-emitting layer.

[0270] [Electron Injection Layer] An electron injection layer is provided on the electron transport layer 6. The electron injection layer functions to transport electrons injected from the cathode to the light-emitting layer. By interposing the electron injection layer between the cathode and the light-emitting layer, electrons are injected into the light-emitting layer at a lower electric field. Examples of materials for the electron injection layer include organic compounds such as fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylene tetracarboxylic acid, fluorenylidenemethane, anthraquinodimethane, and anthrone. Examples of materials for the electron injection layer also include inorganic compounds such as various oxides, fluorides, nitrides, and oxynitrides of SiO2, AlO, SiN, SiON, AlON, GeO, LiO, LiON, TiO, TiON, TaO, TaON, TaN, LiF, C, and Yb.

[0271] [Cathode] A cathode is provided on the electron injection layer. In the case of an organic electroluminescent device configured to extract only light that has passed through the anode, the cathode can be formed from any conductive material. Examples of materials for the cathode include metals with a low work function (hereinafter also referred to as electron injection metals), alloys, electrically conductive compounds, and mixtures thereof. Here, a metal with a low work function is, for example, a metal with a work function of 4 eV or less.

[0272] Specific examples of the material for the cathode include sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, and aluminum / aluminum oxide (Al ２ O ３ Among these, in view of electron injection property and durability against oxidation, etc., mixtures of an electron injection metal and a second metal which is a metal having a larger work function value and is more stable than the electron injection metal, such as magnesium / silver mixtures, magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / aluminum oxide (Al ２ O ３ ) mixtures, lithium / aluminum mixtures, etc. are preferred.

[0273] [Protective Layer 9] A protective layer 9 is provided on the cathode patterning layer 50. From the viewpoint of improving light extraction efficiency, the protective layer preferably has a laminated structure made up of multiple layers with different refractive indices. When the protective layer has a laminated structure, the types of layers to be laminated are not particularly limited, but are preferably 2 to 6, 2 to 5, 2 to 4, or 2 to 3, and more preferably made up of two types of layers. When the protective layer has a laminated structure, it is preferable that at least one layer constituting the laminated structure is a low refractive index layer and at least one layer is a high refractive index layer.

[0274] The laminate structure of the capping layer is not particularly limited, but examples thereof include the following structures (1) to (4): (1) high refractive index layer / low refractive index layer (2) low refractive index layer / high refractive index layer (3) low refractive index layer / high refractive index layer / low refractive index layer (4) high refractive index layer / medium refractive index layer / low refractive index layer (5) high refractive index layer / low refractive index layer / high refractive index layer / low refractive index layer

[0275] (Low Refractive Index Layer) The low refractive index layer contains a low refractive index material. The low refractive index material is not particularly limited, and organic compounds, inorganic compounds, polymer compounds, and the like can be used. A mixture of organic compounds, inorganic compounds, and polymer compounds may also be used. The low refractive index layer preferably has a light transmittance of 90% or more in the range of 450 nm to 900 nm and a refractive index of 1.65 or less in the range of 450 nm to 900 nm. More preferably, the refractive index in the range of 450 nm to 900 nm is 1.64 or less, 1.62 or less, 1.60 or less, 1.58 or less, 1.56 or less, 1.54 or less, 1.52 or less, or 1.50 or less.

[0276] The low refractive index layer may be made of, for example, lithium fluoride, 8-hydroxyquinolinolato-lithium, or a fluorinated compound. The thickness of the low refractive index layer is not particularly limited, but is preferably 20 nm to 200 nm, 20 nm to 160 nm, 20 nm to 140 nm, or 30 nm to 120 nm.

[0277] (High Refractive Index Layer) The high refractive index layer preferably has a light transmittance of 90% or more in the range of 450 nm to 900 nm and a refractive index of 1.70 or more in the range of 450 nm to 900 nm. More preferably, the refractive index in the range of 450 nm to 900 nm is 1.71 or more, 1.72 or more, 1.73 or more, 1.74 or more, 1.75 or more, 1.76 or more, 1.77 or more, 1.78 or more, 1.79 or more, or 1.80 or more. The thickness of the high refractive index layer is not particularly limited, but is preferably 20 nm to 200 nm, 20 nm to 160 nm, 20 nm to 140 nm, or 30 nm to 120 nm.

[0278] (High refractive index material) The high refractive index layer contains a high refractive index material. The high refractive index material is not particularly limited, and an organic compound, an inorganic compound, a polymer compound, or the like can be used. A mixture of an organic compound, an inorganic compound, and a polymer compound may also be used. The high refractive index material preferably contains an organic compound, from the viewpoints of facilitating film thickness control by vacuum deposition and enabling a lower deposition temperature.

[0279] In particular, due to their excellent thin film stability and durability, high refractive index materials 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 copolymers, conductive polymer oligomers (particularly thiophene oligomers), porphyrin compounds, aromatic tertiary amine compounds, carbazole compounds, styrylamine compounds, triazine derivatives, and pyrimidine derivatives. Among these, carbazole compounds, porphyrin compounds, aromatic tertiary amine compounds, and styrylamine compounds are preferred due to their excellent durability, and carbazole compounds and aromatic tertiary amine compounds are particularly preferred.

[0280] (Medium Refractive Index Layer) The medium refractive index layer has a light transmittance of 90% or more in the range of 450 nm to 900 nm, and a refractive index of 1.60 or more in the range of 450 nm to 900 nm.

[0281] In the range of 450 nm to 900 nm, the refractive index is preferably 1.61 or more, and more preferably 1.61 or more, 1.62 or more, 1.63 or more, 1.64 or more, 1.65 or more, 1.66 or more, 1.67 or more, 1.68 or more, or 1.69 or more. The film thickness of the medium refractive index layer is not particularly limited, but is preferably 20 nm to 200 nm, 20 nm to 160 nm, 20 nm to 140 nm, or 30 nm to 120 nm.

[0282] (Medium Refractive Index Material) The medium refractive index layer contains a medium refractive index material. The medium refractive index material is not particularly limited, and organic compounds, inorganic compounds, polymer compounds, etc. can be used. A mixture of organic compounds, inorganic compounds, and polymer compounds may also be used. The medium refractive index material preferably contains an organic compound, as this facilitates film thickness control by vacuum deposition and allows for lower deposition temperatures. The relationship between the refractive indices of the low refractive index layer, medium refractive index layer, and high refractive index layer in the range of 450 nm to 900 nm is: low refractive index layer≦medium refractive index layer≦high refractive index layer.

[0283] [Electronic Device] An electronic device according to one embodiment of the present disclosure includes the above-described metal patterning material. As described above, when forming a metal pattern, an organic material pattern including the metal patterning material is formed, and therefore 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 including the metal patterning material together with the metal pattern.

[0284] 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 or metal wiring on a circuit board. In other words, any electronic device that includes patterned metal electrodes or metal wiring on a circuit board can be obtained using the above-described method for forming a metal pattern according to this embodiment. Such electronic devices have a highly accurate metal pattern.

[0285] 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.

[0286] [Transmittance measurement] Measurement device: V-750 manufactured by JASCO Corporation. Measurement range: 550 to 800 nm

[0287] Example 1 Synthesis of Compound (Z1) Under a nitrogen atmosphere, 1,4-bis(4-bromophenyl)benzene (4.0 mmol), heptadecafluorooctyl iodide (12 mmol), and copper powder (20 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 140°C for 24 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z1) as a white solid (yield: 48%). The compound was identified by FDMS measurement. FDMS: 1068.

[0288] Example 1' Evaluation of Metal Adhesion of Compound (Z1) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４ The atmosphere was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z1) was deposited at a deposition rate of 0.2 nm / sec to form a 50 nm film on a glass substrate equipped with a metal mask having an opening of 2 mm x 1 mm. The metal mask was then removed, and silver and magnesium (1 / 9) were deposited at a deposition rate of 0.2 nm / sec to form a 10 nm film. No silver or magnesium was deposited on the area where compound (Z1) was deposited, forming a transparent area of ​​2 mm x 1 mm.

[0289] Example 2 Synthesis of compound (Z71) Under a nitrogen atmosphere, 4,4",6,6"-dibromo-2,2';6',2"-terpyridine (4.0 mmol), heptadecafluorooctyl iodide (24 mmol), and copper powder (40 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 140°C for 24 hours. After allowing to cool to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and then purified by silica gel column chromatography to obtain the target compound (Z71) as a white solid (yield: 58%). The compound was identified by FDMS measurement. FDMS: 1905.

[0290] Example 2' Evaluation of Metal Adhesion of Compound (Z71) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４ The atmosphere was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z71) was deposited to a thickness of 20 nm at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 2 mm × 1 mm was placed. The metal mask was then removed, and magnesium was deposited to a thickness of 10 nm at a deposition rate of 0.2 nm / sec. No magnesium film was formed in the area where compound (Z71) had been deposited, forming a transparent area of ​​2 mm × 1 mm.

[0291] Example 3 Synthesis of intermediate (I1) Under a nitrogen atmosphere, tripotassium phosphate (5.0 mmol), tetrakis(triphenylphosphine)palladium (0.1 mmol), 2,6-naphthalenediboronic acid bis(pinacol) (1.0 mmol), and 2,4,6-trichloropyrimidine (3.0 mmol) were dissolved in THF (50 ml) and water (50 ml), and the solution was stirred at 70°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I1) as a white solid (yield: 48%). The compound was identified by FDMS analysis. FDMS: 420.

[0292] Example 4 Synthesis of compound (Z25) Under a nitrogen atmosphere, intermediate I1 (5.0 mmol), 1H,1H,9H-hexadecafluoro-1-nonanol (24.0 mmol), and cesium carbonate (30.0 mmol) were suspended in tetrahydrofuran (100 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z25) as a white solid (yield 25%). The compound was identified by FDMS measurement. FDMS: 2004.

[0293] Example 4' Evaluation of Metal Adhesion of Compound (Z25) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４ The chamber was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z25) was deposited at a deposition rate of 0.2 nm / sec to form a 10 nm film on a glass substrate with a metal mask having an opening of 2 mm x 1 mm. The metal mask was then removed, and ytterbium and lithium fluoride (1 / 1) were deposited at a deposition rate of 0.01 nm / sec to form a 2 nm film, followed by silver and magnesium (1 / 1) at a deposition rate of 0.1 nm / sec to form a 20 nm film. No films of ytterbium, lithium fluoride, silver, or magnesium were formed in the area where compound (Z25) was deposited, forming a transparent area of ​​2 mm x 1 mm.

[0294] Example 5 Synthesis of Intermediate (I2) Under a nitrogen atmosphere, tripotassium phosphate (5.0 mmol), tetrakis(triphenylphosphine)palladium (0.1 mmol), 3-(6-chloropyridin-2-yl)phenylboronic acid pinacol (2.0 mmol), and 2,4,6-trichloropyrimidine (3.0 mmol) were dissolved in THF (50 ml) and water (50 ml) and stirred at 70°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I2) as a white solid (yield 48%). The compound was identified by FDMS analysis. FDMS: 335.

[0295] Example 6 Synthesis of compound (Z61) Under a nitrogen atmosphere, intermediate I2 (2.0 mmol), tridecafluorohexyl iodide (12 mmol), and copper powder (24 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 140°C for 24 hours. After cooling to room temperature, the mixture was separated into pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z61) as a white solid (yield 31%). The compound was identified by FDMS analysis. FDMS: 1187.

[0296] Example 6' Evaluation of Metal Adhesion of Compound (Z61) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４ The atmosphere was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z61) was deposited at a deposition rate of 0.2 nm / sec to form a 20 nm film on a glass substrate equipped with a metal mask having an opening of 2 mm x 1 mm. The metal mask was then removed, and silver was deposited at a deposition rate of 0.2 nm / sec to form a 15 nm film. No silver was deposited on the area where compound (Z61) had been deposited, forming a transparent area of ​​2 mm x 1 mm.

[0297] Example 7 Synthesis of Intermediate (I3) Under a nitrogen atmosphere, tripotassium phosphate (10.0 mmol), tetrakis(triphenylphosphine)palladium (0.1 mmol), [1-(3-chloropyridin-2-yl)naphthalen-2-yl]boronic acid pinacol (4.0 mmol), and 2,4,6-trichloropyrimidine (6.0 mmol) were dissolved in THF (50 ml) and water (50 ml) and stirred at 70°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I3) as a white solid (yield 19%). The compound was identified by FDMS analysis. FDMS: 386.

[0298] Example 8 Synthesis of Intermediate (I4) Under a nitrogen atmosphere, intermediate I3 (5.0 mmol), 1H,1H-nonafluoro-1-pentanol (12.0 mmol), and cesium carbonate (15.0 mmol) were suspended in tetrahydrofuran (100 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I4) as a white solid (yield: 59%). The compound was identified by FDMS measurement. FDMS: 814.

[0299] Example 9 Synthesis of compound (Z66) Under a nitrogen atmosphere, intermediate I4 (4.0 mmol), heptadecafluorooctyl iodide (8.0 mmol), and copper powder (16 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 140°C for 24 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z66) as a white solid (yield 48%). The compound was identified by FDMS analysis. FDMS: 1198.

[0300] Example 9' Evaluation of Metal Adhesion of Compound (Z66) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４ The atmosphere was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z66) was deposited at a deposition rate of 0.2 nm / sec to form a 25 nm film on a glass substrate equipped with a metal mask having an opening of 2 mm x 1 mm. The metal mask was then removed, and silver was deposited at a deposition rate of 1.0 nm / sec to form a 20 nm film. No silver was deposited on the area where compound (Z66) had been deposited, forming a transparent area of ​​2 mm x 1 mm.

[0301] Example 10 Synthesis of Intermediate (I5) Under a nitrogen atmosphere, tripotassium phosphate (6.0 mmol), tetrakis(triphenylphosphine)palladium (0.1 mmol), 9,9-dimethylfluorene-2,7-diboronic acid bis(pinacol) (2.0 mmol), and 2,4,6-trichloropyrimidine (6.0 mmol) were dissolved in THF (50 ml) and water (50 ml) and stirred at 70°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I5) as a white solid (yield 35%). The compound was identified by FDMS analysis. FDMS: 486.

[0302] Example 11 Synthesis of compound (Z34) Under a nitrogen atmosphere, intermediate I5 (5.0 mmol), 1H,1H-nonafluoro-1-pentanol (24.0 mmol), and cesium carbonate (30.0 mmol) were suspended in tetrahydrofuran (100 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z34) as a white solid (yield 61%). The compound was identified by FDMS measurement. FDMS: 1342.

[0303] Example 11' Evaluation of Metal Adhesion of Compound (Z34) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４ The atmosphere was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z34) was deposited at a deposition rate of 0.2 nm / sec to form a 50 nm film on a glass substrate equipped with a metal mask having an opening of 2 mm x 1 mm. The metal mask was then removed, and silver and magnesium (1 / 1) were deposited at a deposition rate of 0.1 nm / sec to form a 20 nm film. No silver or magnesium was deposited on the area where compound (Z34) was deposited, forming a transparent area of ​​2 mm x 1 mm.

[0304] Example 12 Synthesis of Intermediate (I6) Under a nitrogen atmosphere, tripotassium phosphate (20.0 mmol), tetrakis(triphenylphosphine)palladium (0.2 mmol), (9,9'-spirobi[9H-fluorene]-2,7,2',7'-diyl)tetra(pinacol borate) (2.0 mmol), and 2,5-dibromopyridine (12.0 mmol) were dissolved in THF (50 ml) and water (50 ml) and stirred at 70°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I6) as a white solid (yield 35%). The compound was identified by FDMS analysis. FDMS: 936.

[0305] Example 13 Synthesis of compound (Z13) Under a nitrogen atmosphere, intermediate I6 (2.0 mmol), tridecafluorohexyl iodide (12 mmol), and copper powder (24 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 140°C for 24 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z13) as a white solid (yield 52%). The compound was identified by FDMS analysis. FDMS: 1896.

[0306] Example 13' Evaluation of Metal Adhesion of Compound (Z13) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４ The atmosphere was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z13) was deposited at a deposition rate of 0.2 nm / sec to form a 50 nm film on a glass substrate equipped with a metal mask having an opening of 2 mm × 1 mm. The metal mask was then removed, and magnesium was deposited at a deposition rate of 0.1 nm / sec to form a 30 nm film. No magnesium was deposited on the area where compound (Z13) had been deposited, forming a transparent area of ​​2 mm × 1 mm.

[0307] Example 14 Synthesis of intermediate (I7) Under a nitrogen atmosphere, tripotassium phosphate (10.0 mmol), tetrakis(triphenylphosphine)palladium (0.1 mmol), adamantane, 1,3-bis[4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenyl] (2.0 mmol), and 2,4,6-trichloropyrimidine (6.0 mmol) were dissolved in THF (50 ml) and water (50 ml) and stirred at 70°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I7) as a white solid (yield: 48%). The compound was identified by FDMS analysis. FDMS: 580.

[0308] Example 15 Synthesis of compound (Z115) Under a nitrogen atmosphere, intermediate I7 ​​(5.0 mmol), 1H,1H,7H-dodecafluoro-1-heptanol (24.0 mmol), and cesium carbonate (30.0 mmol) were suspended in tetrahydrofuran (100 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z115) as a white solid (yield 66%). The compound was identified by FDMS measurement. FDMS: 1764.

[0309] Example 15' Evaluation of Metal Adhesion of Compound (Z115) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４ The atmosphere was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. A 30 nm film of compound (Z115) was formed at a deposition rate of 0.2 nm / sec on a glass substrate with a metal mask having an opening of 2 mm x 1 mm. The metal mask was then removed, and lithium fluoride was deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver and magnesium (1 / 1) at a deposition rate of 0.1 nm / sec to a thickness of 10 nm. Lithium fluoride, silver, and magnesium were not deposited on the area where compound (Z115) was deposited, forming a transparent area of ​​2 mm x 1 mm.

[0310] Example 16 Synthesis of intermediate (I8) Under a nitrogen atmosphere, one drop of 1,2-dibromoethane was added to a solution of magnesium (7.5 mmol) suspended in tetrahydrofuran (20 ml), and 1-bromo-3-(4-chlorophenyl)adamantane (7.0 mmol) dissolved in tetrahydrofuran (20 ml) was added dropwise over 20 minutes. After the dropwise addition, the mixture was stirred at 60°C for 3 hours. The mixture was then returned to room temperature, and 1,3,5-trichloropyrimidine (8.0 mmol) dissolved in tetrahydrofuran (20 ml) was added dropwise over 20 minutes. After the dropwise addition, the mixture was stirred at 60°C for 3 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I8) as a white solid (yield 15%). The compound was identified by FDMS analysis. FDMS: 392

[0311] Example 17 Synthesis of Intermediate (I9) Under a nitrogen atmosphere, intermediate I8 (5.0 mmol), 1H,1H-nonafluoro-1-pentanol (12.0 mmol), and cesium carbonate (15.0 mmol) were suspended in tetrahydrofuran (100 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I9) as a white solid (yield 64%). The compound was identified by FDMS measurement. FDMS: 820.

[0312] Example 18 Synthesis of compound (Z119) Under a nitrogen atmosphere, tripotassium phosphate (12.0 mmol), palladium acetate (0.1 mmol), dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (0.2 mmol), 2-pentafluoroethylpyridine-5-boronic acid pinacol (8.0 mmol), and intermediate I9 (4.0 mmol) were dissolved in THF (50 ml) and water (50 ml) and stirred at 70°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z119) as a white solid (yield 19%). The compound was identified by FDMS analysis. FDMS: 981.

[0313] Example 18' Evaluation of Metal Adhesion of Compound (Z119) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４ The atmosphere was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z119) was deposited at a deposition rate of 0.2 nm / sec to a thickness of 10 nm on a glass substrate equipped with a metal mask having an opening of 2 mm x 1 mm. The metal mask was then removed, and silver and magnesium (1 / 1) were deposited at a deposition rate of 0.01 nm / sec to a thickness of 12 nm. No silver or magnesium was deposited on the area where compound (Z119) was deposited, forming a transparent area of ​​2 mm x 1 mm.

[0314] Example 19 Synthesis of Intermediate (I10) Under a nitrogen atmosphere, tripotassium phosphate (15.0 mmol), tetrakis(triphenylphosphine)palladium (0.1 mmol), quinoline, 6-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)-2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenyl]- (5.0 mmol), and 2,4,6-trichloropyrimidine (12.0 mmol) were dissolved in THF (50 ml) and water (50 ml) and stirred at 70°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I10) as a white solid (yield: 43%). The compound was identified by FDMS analysis. FDMS: 497.

[0315] Example 20 Synthesis of compound (Z92) Under a nitrogen atmosphere, intermediate I10 (5.0 mmol), 1H,1H-nonafluoro-1-pentanol (24.0 mmol), and cesium carbonate (30.0 mmol) were suspended in tetrahydrofuran (100 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z92) as a white solid (yield 61%). The compound was identified by FDMS measurement. FDMS: 1353.

[0316] Example 20' Evaluation of Metal Adhesion of Compound (Z92) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４The atmosphere was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z92) was deposited at a deposition rate of 0.2 nm / sec to form a 50 nm film on a glass substrate equipped with a metal mask having an opening of 2 mm x 1 mm. The metal mask was then removed, and copper was deposited at a deposition rate of 0.1 nm / sec to form a 5 nm film. No copper was deposited on the area where compound (Z92) had been deposited, forming a transparent area of ​​2 mm x 1 mm.

[0317] Example 21 Synthesis of intermediate (I11) Under a nitrogen atmosphere, tripotassium phosphate (20.0 mmol), tetrakis(triphenylphosphine)palladium (0.1 mmol), phenanthrene-2,7-diboronic acid bis(pinacol) (5.0 mmol), and 6,6'-dibromo-3,3'-bipyridine (20.0 mmol) were dissolved in THF (50 ml) and water (50 ml), and the solution was stirred at 70°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I11) as a white solid (yield 68%). The compound was identified by FDMS analysis. FDMS: 642.

[0318] Example 22 Synthesis of compound (Z78) Under a nitrogen atmosphere, intermediate I11 (4.0 mmol), heptadecafluorooctyl iodide (12 mmol), and copper powder (20 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 140°C for 24 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z78) as a white solid (yield 45%). The compound was identified by FDMS analysis. FDMS: 1322.

[0319] Example 22' Evaluation of Metal Adhesion of Compound (Z78) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４The atmosphere was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z78) was deposited at a deposition rate of 0.2 nm / sec to a thickness of 25 nm on a glass substrate equipped with a metal mask having an opening of 2 mm x 1 mm. The metal mask was then removed, and silver was deposited at a deposition rate of 0.2 nm / sec to a thickness of 8 nm. No silver was deposited on the area where compound (Z78) had been deposited, forming a transparent area of ​​2 mm x 1 mm.

[0320] Example 23 Synthesis of intermediate (I12) Under a nitrogen atmosphere, tripotassium phosphate (30.0 mmol), tetrakis(triphenylphosphine)palladium (0.2 mmol), benzene, 1,2-bis[3-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenyl]- (10.0 mmol), 2,4,6-trichloropyrimidine (24.0 mmol), and 2,4,6-trichlorotriazine (12.0 mmol) were dissolved in THF (50 ml) and water (50 ml) and stirred at 70°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I12) as a white solid (yield 18%). The compound was identified by FDMS analysis. FDMS: 523.

[0321] Example 24 Synthesis of compound (Z65) Under a nitrogen atmosphere, intermediate I12 (5.0 mmol), 1H,1H-nonafluoro-1-pentanol (24.0 mmol), and cesium carbonate (30.0 mmol) were suspended in tetrahydrofuran (100 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z65) as a white solid (yield 61%). The compound was identified by FDMS measurement. FDMS: 1353.

[0322] Example 24' Evaluation of Metal Adhesion of Compound (Z65) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４ The atmosphere was evacuated using a vacuum pump until the pressure reached 10 Pa or less. Compound (Z65) was deposited at a deposition rate of 0.2 nm / sec onto a glass substrate on which a metal mask with an opening of 2 mm x 1 mm was placed. The metal mask was then removed, and silver was deposited at a deposition rate of 0.2 nm / sec to a thickness of 20 nm. No silver was deposited on the area where compound (Z65) had been deposited, and a transparent area of ​​2 mm x 1 mm was formed.

[0323] Example 25 Synthesis of intermediate (I13) Under a nitrogen atmosphere, 4,6-dichloro-2-(4-chlorophenyl)pyrimidine (5.0 mmol), 1H,1H-nonafluoro-1-pentanol (12.0 mmol), and cesium carbonate (15.0 mmol) were suspended in tetrahydrofuran (100 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (I13) as a white solid (yield 69%). The compound was identified by FDMS analysis. FDMS: 686.

[0324] Example 26 Synthesis of intermediate (I14) Under a nitrogen atmosphere, potassium acetate (4.0 mmol), palladium acetate (0.1 mmol), dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (0.20 mmol), intermediate I13 (2.0 mmol), and bis(pinacolato)diboron (3.0 mmol) were dissolved in THF (50 ml) and stirred at 70°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I14) as a white solid (yield 43%). The compound was identified by FDMS analysis. FDMS: 778.

[0325] Example 27 Synthesis of compound (Z88) Under a nitrogen atmosphere, tripotassium phosphate (24.0 mmol), tetrakis(triphenylphosphine)palladium (0.1 mmol), intermediate I14 (12.0 mmol), and 2,5-dibromofuran (5.0 mmol) were dissolved in THF (50 ml) and water (50 ml), and the solution was stirred at 70°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target product (Z88) as a white solid (yield: 51%). The compound was identified by FDMS analysis. FDMS: 1368.

[0326] Example 27' Evaluation of Metal Adhesion of Compound (Z88) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４The chamber was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z88) was deposited at a deposition rate of 0.2 nm / sec to a thickness of 100 nm on a glass substrate equipped with a metal mask having an opening of 2 mm x 1 mm. The metal mask was then removed, and ytterbium was deposited at a deposition rate of 0.01 nm / sec to a thickness of 1 nm, followed by deposition of silver and magnesium (1 / 1) at a deposition rate of 0.1 nm / sec to a thickness of 14 nm. No ytterbium, silver, or magnesium was deposited on the portion where compound (Z88) was deposited, forming a transparent region of 2 mm x 1 mm.

[0327] Example 28 Synthesis of intermediate (I15) Under a nitrogen atmosphere, tripotassium phosphate (24.0 mmol), tetrakis(triphenylphosphine)palladium (0.1 mmol), intermediate I14 (12.0 mmol), and 2-bromo,5-chlorobenzothiophene (12.0 mmol) were dissolved in THF (50 ml) and water (50 ml) and stirred at 70°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I15) as a white solid (yield: 59%). The compound was identified by FDMS analysis. FDMS: 818.

[0328] Example 29 Synthesis of intermediate (I16) Under a nitrogen atmosphere, potassium acetate (4.0 mmol), palladium acetate (0.10 mmol), dicyclohexyl(2',4',6'-triisopropyl-[1,1'-biphenyl]-2-yl)phosphine (0.20 mmol), intermediate I15 (2.0 mmol), and bis(pinacolato)diboron (3.0 mmol) were dissolved in THF (50 ml) and stirred at 70°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I16) as a white solid (yield 48%). The compound was identified by FDMS analysis. FDMS: 910.

[0329] Example 30 Synthesis of intermediate (I17) Under a nitrogen atmosphere, tripotassium phosphate (24.0 mmol), tetrakis(triphenylphosphine)palladium (0.1 mmol), intermediate I16 (12.0 mmol), and 2,5-dibromopyridine (24.0 mmol) were dissolved in THF (50 ml) and water (50 ml), and the solution was stirred at 70°C for 6 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I17) as a white solid (yield 64%). The compound was identified by FDMS analysis. FDMS: 818.

[0330] Example 31 Synthesis of compound (Z105) Under a nitrogen atmosphere, intermediate I17 (4.0 mmol), heptadecafluorooctyl iodide (8.0 mmol), and copper powder (16.0 mmol) were suspended in dimethyl sulfoxide (50 mL) and stirred at 140°C for 24 hours. After cooling to room temperature, the mixture was separated using pure water and chloroform, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z105) as a white solid (yield 45%). The compound was identified by FDMS analysis. FDMS: 1279.

[0331] Example 31' Evaluation of Metal Adhesion of Compound (Z105) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４ The atmosphere was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z105) was deposited at a deposition rate of 0.2 nm / sec to form a 20 nm film on a glass substrate with a metal mask having an opening of 2 mm × 1 mm. The metal mask was then removed, and zinc was deposited at a deposition rate of 0.2 nm / sec to form a 5 nm film. No zinc was deposited on the area where compound (Z105) had been deposited, forming a transparent area of ​​2 mm × 1 mm.

[0332] Example 32 Synthesis of intermediate (I18) Under a nitrogen atmosphere, 2,4,6-tetrachloropyrimidine (16.0 mmol), 1H,1H,9H-hexadecafluoro-1-nonanol (35.0 mmol), and cesium carbonate (35.0 mmol) were suspended in tetrahydrofuran (100 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I18) as a white solid (yield 73%). The compound was identified by FDMS measurement. FDMS: 974.

[0333] Example 33 Synthesis of compound (Z149) Under a nitrogen atmosphere, intermediate I18 (8.8 mmol), homopiperazine (4.0 mmol), and cesium carbonate (10.0 mmol) were suspended in tetrahydrofuran (50 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z149) as a white solid (yield 58%). The compound was identified by FDMS analysis. FDMS: 1976.

[0334] Example 33' Evaluation of Metal Adhesion of Compound (Z149) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４ The chamber was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z149) was deposited at a deposition rate of 0.2 nm / sec to form a 15 nm film on a glass substrate with a metal mask having an opening of 2 mm x 1 mm. The metal mask was then removed, and ytterbium and lithium fluoride (1 / 1) were deposited at a deposition rate of 0.01 nm / sec to form a 3 nm film, followed by silver and magnesium (9 / 1) at a deposition rate of 0.1 nm / sec to form a 12 nm film. Lithium fluoride, ytterbium, silver, and magnesium were not deposited on the area where compound (Z149) was deposited, forming a transparent area of ​​2 mm x 1 mm.

[0335] Example 34 Synthesis of compound (Z141) Under a nitrogen atmosphere, intermediate I18 (8.8 mmol), piperazine (4.0 mmol), and cesium carbonate (10.0 mmol) were suspended in tetrahydrofuran (50 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z141) as a white solid (yield 56%). The compound was identified by FDMS analysis. FDMS: 1962.

[0336] Example 34' Evaluation of Metal Adhesion of Compound (Z141) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４ The chamber was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z141) was deposited at a deposition rate of 0.2 nm / sec to form a 10 nm film on a glass substrate with a metal mask having an opening of 2 mm x 1 mm. The metal mask was then removed, and ytterbium and lithium fluoride (1 / 1) were deposited at a deposition rate of 0.01 nm / sec to form a 2 nm film, followed by silver and magnesium (9 / 1) at a deposition rate of 0.1 nm / sec to form a 20 nm film. Ytterbium, lithium fluoride, silver, and magnesium were not deposited on the area where compound (Z141) was deposited, forming a transparent area of ​​2 mm x 1 mm.

[0337] Example 35 Synthesis of intermediate (I19) Under a nitrogen atmosphere, 2,4,6-tetrachloropyrimidine (16.0 mmol), 1H,1H-nonafluoro-1-pentanol (35.0 mmol), and cesium carbonate (35.0 mmol) were suspended in tetrahydrofuran (100 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I19) as a white solid (yield 69%). The compound was identified by FDMS measurement. FDMS: 610.

[0338] Example 36 Synthesis of compound (Z144) Under a nitrogen atmosphere, intermediate I19 (8.8 mmol), 3,3'-bipiperazine (4.0 mmol), and cesium carbonate (10.0 mmol) were suspended in tetrahydrofuran (50 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z144) as a white solid (yield 48%). The compound was identified by FDMS measurement. FDMS: 1316.

[0339] Example 36' Evaluation of Metal Adhesion of Compound (Z144) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４ The atmosphere was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z144) was deposited to a thickness of 25 nm at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 2 mm x 1 mm was placed. The metal mask was then removed, and ytterbium was deposited to a thickness of 5 nm at a deposition rate of 0.01 nm / sec, followed by deposition of silver and magnesium (1 / 1) to a thickness of 20 nm at a deposition rate of 0.1 nm / sec. No films of ytterbium, magnesium, or silver were deposited on the area on which compound (Z144) was deposited, forming a transparent area of ​​2 mm x 1 mm.

[0340] Example 37 Synthesis of intermediate (I20) Under a nitrogen atmosphere, 2,4,6-tetrachloropyrimidine (16.0 mmol), 3,3,4,4,5,5,6,6,9,9,10,10,11,11,12,12,12-heptadecafluoro-7-dodecen-1-ol (35.0 mmol), and cesium carbonate (35.0 mmol) were suspended in tetrahydrofuran (100 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using purified water and ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I20) as a white solid (yield 21%). The compound was identified by FDMS analysis. FDMS: 1090.

[0341] Example 38 Synthesis of compound (Z95) Under a nitrogen atmosphere, intermediate I20 (8.8 mmol), 1,2,3,4-tetrahydroquinoxaline (4.0 mmol), and cesium carbonate (10.0 mmol) were suspended in tetrahydrofuran (50 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z95) as a white solid (yield 48%). The compound was identified by FDMS measurement. FDMS: 2242.

[0342] Example 38' Evaluation of Metal Adhesion of Compound (Z95) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４ The atmosphere was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z95) was deposited at a deposition rate of 0.2 nm / sec to a thickness of 15 nm on a glass substrate on which a metal mask with an opening of 2 mm × 1 mm was placed. The metal mask was then removed, and indium was deposited at a deposition rate of 0.1 nm / sec to a thickness of 5 nm. No indium was deposited on the area where compound (Z95) had been deposited, and a transparent area of ​​2 mm × 1 mm was formed.

[0343] Example 39 Synthesis of intermediate (I21) Under a nitrogen atmosphere, 2,4,6-tetrachloropyrimidine (8.8 mmol), piperazine (4.0 mmol), and cesium carbonate (10.0 mmol) were suspended in tetrahydrofuran (50 mL) and stirred at 70°C for 10 hours. After allowing to cool to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I21) as a white solid (yield 48%). The compound was identified by FDMS measurement. FDMS: 378.

[0344] Example 40 Synthesis of compound (Z157) Under a nitrogen atmosphere, intermediate I21 (5.0 mmol), 1H,1H,7H-dodecafluoro-1-heptanol (24.0 mmol), and cesium carbonate (24.0 mmol) were suspended in tetrahydrofuran (100 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z157) as a white solid (yield 68%). The compound was identified by FDMS measurement. FDMS: 1562.

[0345] Example 40' Evaluation of Metal Adhesion of Compound (Z157) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol), and then cleaned by ultraviolet ozone. After that, the substrate was placed in a vacuum deposition apparatus and 1.0 x 10 －４ The chamber was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z157) was deposited at a deposition rate of 0.2 nm / sec to form a 10 nm film on a glass substrate equipped with a metal mask having an opening of 2 mm x 1 mm. The metal mask was then removed, and lithium fluoride 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. Neither lithium fluoride nor silver was deposited on the area where compound (Z157) was deposited, forming a transparent area of ​​2 mm x 1 mm.

[0346] Example 41 Synthesis of compound (Z158) Under a nitrogen atmosphere, intermediate I21 (5.0 mmol), 1H,1H-nonafluoro-1-pentanol (24.0 mmol), and cesium carbonate (30.0 mmol) were suspended in tetrahydrofuran (100 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z158) as a white solid (yield 71%). The compound was identified by FDMS measurement. FDMS: 1234.

[0347] Example 41' Evaluation of Metal Adhesion of Compound (Z158) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４ The chamber was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. A 20 nm film of compound (Z158) was formed at a deposition rate of 0.2 nm / sec on a glass substrate with a metal mask having an opening of 2 mm x 1 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 silver deposition at a deposition rate of 0.1 nm / sec to a thickness of 10 nm. No ytterbium or silver was deposited on the area where compound (Z158) was deposited, forming a transparent area of ​​2 mm x 1 mm.

[0348] Example 42 Synthesis of intermediate (I22) Under a nitrogen atmosphere, 2,4,6-tetrachloropyrimidine (16.0 mmol), 1H,1H,7H-dodecafluoro-1-heptanol (35 mmol), and cesium carbonate (35 mmol) were suspended in tetrahydrofuran (100 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I22) as a white solid (yield 78%). The compound was identified by FDMS measurement. FDMS: 774.

[0349] Example 43 Synthesis of compound (Z146) Under a nitrogen atmosphere, intermediate (I22) (8.8 mmol), piperazine (4.0 mmol), and cesium carbonate (10.0 mmol) were suspended in tetrahydrofuran (50 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z146) as a white solid (yield 43%). The compound was identified by FDMS analysis. FDMS: 1562.

[0350] Example 43' Evaluation of Metal Adhesion of Compound (Z146) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４ The atmosphere was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z146) was deposited to a thickness of 20 nm at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 2 mm x 1 mm was placed. The metal mask was then removed, and copper was deposited to a thickness of 5 nm at a deposition rate of 0.01 nm / sec. No copper was deposited on the area where compound (Z146) had been deposited, forming a transparent area of ​​2 mm x 1 mm.

[0351] Example 44 Synthesis of intermediate (I23) Under a nitrogen atmosphere, 2,4,6-tetrachloropyrimidine (8.8 mmol), homopiperazine (4.0 mmol), and cesium carbonate (10.0 mmol) were suspended in tetrahydrofuran (50 mL) and stirred at 70°C for 10 hours. After allowing to cool to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I23) as a white solid (yield 51%). The compound was identified by FDMS measurement. FDMS: 392.

[0352] Example 45 Synthesis of compound (Z160) Under a nitrogen atmosphere, intermediate I23 (5.0 mmol), 1H,1H,7H-dodecafluoro-1-heptanol (24.0 mmol), and cesium carbonate (30.0 mmol) were suspended in tetrahydrofuran (100 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z160) as a white solid (yield 71%). The compound was identified by FDMS measurement. FDMS: 1576.

[0353] Example 45' Evaluation of Metal Adhesion of Compound (Z160) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４ The atmosphere was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z160) was deposited at a deposition rate of 0.2 nm / sec to a thickness of 10 nm on a glass substrate equipped with a metal mask having an opening of 2 mm x 1 mm. The metal mask was then removed, and silver was deposited at a deposition rate of 0.2 nm / sec to a thickness of 50 nm. No silver was deposited on the area where compound (Z160) had been deposited, forming a transparent area of ​​2 mm x 1 mm.

[0354] Example 46 Synthesis of compound (Z161) Under a nitrogen atmosphere, intermediate I23 (5.0 mmol), 1H,1H-nonafluoro-1-pentanol (24.0 mmol), and cesium carbonate (30.0 mmol) were suspended in tetrahydrofuran (100 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z161) as a white solid (yield 71%). The compound was identified by FDMS measurement. FDMS: 1248.

[0355] Example 46' Evaluation of Metal Adhesion of Compound (Z161) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４ The atmosphere was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z161) was deposited to a thickness of 30 nm at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 2 mm x 1 mm was placed. The metal mask was then removed, and magnesium was deposited to a thickness of 80 nm at a deposition rate of 0.2 nm / sec. No magnesium was deposited on the area where compound (Z161) had been deposited, forming a transparent area of ​​2 mm x 1 mm.

[0356] Example 47 Synthesis of compound (Z154) Under a nitrogen atmosphere, intermediate I22 (8.8 mmol), 2,5-dimethylpiperazine (4.0 mmol), and cesium carbonate (10 mmol) were suspended in tetrahydrofuran (50 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z154) as a white solid (yield 62%). The compound was identified by FDMS measurement. FDMS: 1590.

[0357] Example 47' Evaluation of Metal Adhesion of Compound (Z154) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４ The chamber was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z154) was deposited at a deposition rate of 0.2 nm / sec to a thickness of 10 nm on a glass substrate equipped with a metal mask having an opening of 2 mm x 1 mm. The metal mask was then removed, and gold was deposited at a deposition rate of 0.1 nm / sec to a thickness of 5 nm. No gold was deposited on the area where compound (Z154) had been deposited, forming a transparent area of ​​2 mm x 1 mm.

[0358] Example 48 Synthesis of compound (Z99) Under a nitrogen atmosphere, intermediate I20 (8.8 mmol), 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine (4.0 mmol), and cesium carbonate (10 mmol) were suspended in tetrahydrofuran (50 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z99) as a white solid (yield 28%). The compound was identified by FDMS measurement. FDMS: 2256.

[0359] Example 48' Evaluation of Metal Adhesion of Compound (Z99) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４ The atmosphere was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. A 50 nm film of compound (Z99) was formed at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 2 mm × 1 mm was placed. The metal mask was then removed, and 8 nm of chromium was deposited at a deposition rate of 0.1 nm / sec. No chromium was deposited on the area where compound (Z99) was deposited, forming a transparent area of ​​2 mm × 1 mm.

[0360] Example 49 Synthesis of compound (Z132) Under a nitrogen atmosphere, piperazine, 1,4-bis(2,3,5,6-trifluoro-4-pyridyl)- (5.0 mmol), 1H,1H,7H-dodecafluoro-1-heptanol (24.0 mmol), and cesium carbonate (30.0 mmol) were suspended in tetrahydrofuran (100 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z132) as a white solid (yield 68%). The compound was identified by FDMS measurement. FDMS: 1632.

[0361] Example 49' Evaluation of Metal Adhesion of Compound (Z132) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４ The atmosphere was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z132) was deposited at a deposition rate of 0.2 nm / sec to form a 15 nm film on a glass substrate with a metal mask having an opening of 2 mm x 1 mm. The metal mask was then removed, and ytterbium and lithium fluoride (1 / 1) were 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. Ytterbium, lithium fluoride, and silver were not deposited on the area where compound (Z132) was deposited, forming a transparent area of ​​2 mm x 1 mm.

[0362] Example 50 Synthesis of compound (Z135) Under a nitrogen atmosphere, piperazine, 1,4-bis(2,3,5,6-trifluoro-4-pyridyl)- (5.0 mmol), 1H,1H,9H-hexadecafluoro-1-nonanol (24.0 mmol), and cesium carbonate (30.0 mmol) were suspended in tetrahydrofuran (100 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z135) as a white solid (yield 67%). The compound was identified by FDMS measurement. FDMS: 2032.

[0363] Example 50' Evaluation of Metal Adhesion of Compound (Z135) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４The atmosphere was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. A 12 nm film of compound (Z135) was formed at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 2 mm x 1 mm was placed. The metal mask was then removed, and lead was deposited at a deposition rate of 0.2 nm / sec to a thickness of 10 nm. No lead was deposited on the area where compound (Z135) had been deposited, and a transparent area of ​​2 mm x 1 mm was formed.

[0364] Example 51 Synthesis of intermediate (I24) Under a nitrogen atmosphere, pentafluoropyridine (8.8 mmol), homopiperazine, 1,4-bis(2,3,5,6-trifluoro-4-pyridyl)- (4.0 mmol), and cesium carbonate (10.0 mmol) were suspended in tetrahydrofuran (50 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I24) as a white solid (yield: 54%). The compound was identified by FDMS measurement. FDMS: 398.

[0365] Example 52 Synthesis of compound (Z136) Under a nitrogen atmosphere, intermediate I24 (5.0 mmol), 1H,1H,9H-hexadecafluoro-1-nonanol (24.0 mmol), and cesium carbonate (30.0 mmol) were suspended in tetrahydrofuran (100 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z136) as a white solid (yield 67%). The compound was identified by FDMS measurement. FDMS: 2046.

[0366] Example 52' Evaluation of Metal Adhesion of Compound (Z136) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus. －４The atmosphere was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z136) was deposited to a thickness of 20 nm at a deposition rate of 0.2 nm / sec on a glass substrate on which a metal mask with an opening of 2 mm x 1 mm was placed. The metal mask was then removed, and ytterbium was deposited to a thickness of 1 nm at a deposition rate of 0.01 nm / sec, followed by deposition of silver and magnesium (1 / 1) to a thickness of 30 nm at a deposition rate of 0.1 nm / sec. No films of ytterbium, silver, or magnesium were deposited in the area where compound (Z136) was deposited, forming a transparent area of ​​2 mm x 1 mm.

[0367] Example 53 Synthesis of intermediate (I25) Under a nitrogen atmosphere, pentafluoropyridine (16.0 mmol), 1H,1H,9H-hexadecafluoro-1-nonanol (35.0 mmol), and cesium carbonate (35.0 mmol) were suspended in tetrahydrofuran (100 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target intermediate (I25) as a white solid (yield 54%). The compound was identified by FDMS measurement. FDMS: 993.

[0368] Example 54 Synthesis of compound (Z139) Under a nitrogen atmosphere, intermediate I25 (8.8 mmol), piperazine (4.0 mmol), and cesium carbonate (10.0 mmol) were suspended in tetrahydrofuran (50 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z139) as a white solid (yield 68%). The compound was identified by FDMS analysis. FDMS: 2032.

[0369] Example 54' Evaluation of Metal Adhesion of Compound (Z139) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol) and then cleaned by ultraviolet ozone, and then placed in a vacuum deposition apparatus.－４ The chamber was evacuated using a vacuum pump until the pressure reached 0.2 Pa or less. Compound (Z139) was deposited at a deposition rate of 0.2 nm / sec to form a 15 nm film on a glass substrate equipped with a metal mask having an opening of 2 mm x 1 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. Silver and magnesium (1 / 9) were then deposited at a deposition rate of 0.1 nm / sec to form a 20 nm film, and silver was then deposited at a deposition rate of 0.1 nm / sec to form a 20 nm film. No ytterbium, silver, or magnesium was deposited on the portion where compound (Z139) was deposited, forming a transparent region of 2 mm x 1 mm.

[0370] Example 55 Synthesis of compound (Z170) Under a nitrogen atmosphere, intermediate I25 (4.4 mmol), intermediate I18 (4.4 mmol), piperazine (4.0 mmol), and cesium carbonate (10.0 mmol) were suspended in tetrahydrofuran (50 mL) and stirred at 70°C for 10 hours. After cooling to room temperature, the mixture was separated using pure water and ethyl acetate, and the organic layer was washed with saturated aqueous sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and purified by silica gel column chromatography to obtain the target compound (Z170) as a white solid (yield 11%). The compound was identified by FDMS analysis. FDMS: 1997.

[0371] Example 55' Evaluation of Metal Adhesion of Compound (Z170) A glass substrate was cleaned by boiling (boiling with isopropyl alcohol), and then cleaned by ultraviolet ozone. After that, the substrate was placed in a vacuum deposition apparatus and 1.0 × 10 －４The atmosphere was evacuated using a vacuum pump until the pressure was reduced to 0.2 Pa or less. A 10 nm film of compound (Z170) was formed at a deposition rate of 0.2 nm / sec on a glass substrate with a metal mask having an opening of 2 mm x 1 mm. The metal mask was then removed, and ytterbium and magnesium fluoride (1 / 1) were deposited at a deposition rate of 0.01 nm / sec to a thickness of 1 nm, followed by silver and magnesium (1 / 1) at a deposition rate of 0.1 nm / sec to a thickness of 20 nm, and then silver was deposited at a deposition rate of 0.05 nm / sec to a thickness of 10 nm. In the area where compound (Z170) was deposited, no films of ytterbium, magnesium fluoride, silver, or magnesium were formed, forming a transparent area of ​​2 mm x 1 mm.

[0372] Comparative Example 1' Evaluation of Metal Adhesion of Compound (X1) The following compound (X1) was used as a material for metal patterning, and its metal adhesion was evaluated. The adhesion of metals to compound (X1) was evaluated in the same manner as in Example 4'. Films of ytterbium, lithium fluoride, silver, and magnesium were also formed on the film of compound (X1), and no transparent region was formed.

[0373] Comparative Example 2' Evaluation of Metal Adhesion of Compound (X2) The adhesion of metals to compound (X2) was evaluated in the same manner as in Example 4'. Films of ytterbium, lithium fluoride, silver, and magnesium were also formed on the film of compound (X2), and no transparent region was formed.

[0374] Comparative Example 3' Evaluation of Metal Adhesion of Compound (X3) The adhesion of metals to compound (X3) was evaluated in the same manner as in Example 4'. Films of ytterbium, lithium fluoride, silver, and magnesium were also formed on the film of compound (X3), and no transparent region was formed.

[0375] Comparative Example 4' Evaluation of Metal Adhesion of Compound (X4) The adhesion of metals to compound (X4) was evaluated in the same manner as in Example 4'. Films of ytterbium, lithium fluoride, silver, and magnesium were also formed on the film of compound (X4), and no transparent region was formed.

[0376] Comparative Example 5' Evaluation of Metal Adhesion of Compound (X5) The adhesion of metals to compound (X5) was evaluated in the same manner as in Example 5'. Films of ytterbium, lithium fluoride, silver, and magnesium were also formed on the film of compound (X5), and no transparent region was formed.

[0377] (Transmittance Measurement) Metal adhesion can be evaluated by measuring transmittance, and transmittance decreases as metal adheres. In addition, the transmittance also decreases in correlation with the amount of adhesion.

[0378] Example 4" Measurement of transmittance of compound (Z25) A glass substrate was boiling cleaned (boiling cleaned with isopropyl alcohol), and then further cleaned with ultraviolet ozone. After that, it was placed in a vacuum deposition apparatus and －４ The chamber was evacuated using a vacuum pump until the pressure reached 0.1 Pa or less. First, a 15 nm film of 2,4,6-tri([1,1'-biphenyl]-4-yl)-1,3,5-triazine was deposited on a glass substrate as an underlayer at a deposition rate of 0.1 nm / sec. Next, a metal mask with an opening of 2 mm x 1 mm was placed, and a 15 nm film of compound (Z25) was deposited as a metal patterning layer at a deposition rate of 0.1 nm / sec. Thereafter, the metal mask was removed, and a mixture of ytterbium and lithium fluoride (1 / 1) was deposited on the substrate at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by a mixture of silver and magnesium (1 / 1) deposited on the substrate at a deposition rate of 0.1 nm / sec to a thickness of 20 nm. Finally, a protective layer of [1,1'-biphenyl]-4,4'-diamine, N4,N4'-biphenyl-N4,N4'-bis(9-phenyl-9H-carbazol-3-yl)- was deposited at a deposition rate of 0.1 nm / sec to a thickness of 100 nm to prepare a patterned test element. The transmittance measurement results for a 2 mm x 1 mm area on which the compound (Z25) film was formed are shown in Figure 1. The transmittance was "≧90%," indicating that the formation of a metal film was suppressed.

[0379] Comparative Example 0" Transmittance Measurement of an Element in Which a Metal Pattern Layer Was Not Formed A patterned test element was produced in the same manner as in Example 4" above, except that a metal patterning layer was not used (no film was formed). The results of the transmittance measurement are shown in Figure 2. The transmittance was "≧20%", indicating that a metal film had been formed.

[0380] Comparative Example 1" Measurement of Transmittance of Compound (X1) A patterned test element was produced using compound (X1) in the metal patterning layer in the same manner as in Example 4". The results of measuring the transmittance of a 2 mm x 1 mm area on which compound (X1) was formed are shown in Figure 3. The transmittance was "≧20%", and the formation of a metal film could not be suppressed.

[0381] Reference Example 1" Measurement of transmittance of compound (Y1) A patterned test element was produced using compound (Y1) in the metal patterning layer in the same manner as in Example 4". The results of measuring the transmittance of a 2 mm × 1 mm area on which compound (Y1) was formed are shown in Figure 4. The transmittance was "≧60%".

[0382] Example 2″ to Comparative Example 5″ The transmittance of compounds Z71 (Example 2″), Z105 (Example 31″), Z149 (Example 33″), Z132 (Example 2″), X3 (Comparative Example 3″), and X5 (Comparative Example 5″) was measured in the same manner as in Example 4″ and Comparative Example 1″. The results are also shown in Table 1.

[0383]

[0384] Example 4''' (Preparation of organic EL element having a light-transmitting portion using compound (Z25) in a metal patterning layer) (Evaluation of patterning element) A glass substrate with a reflective ITO electrode was prepared as substrate 1 having an anode 2 on its surface. Two linear reflective ITO electrodes with an electrode width of 10 mm were formed on the substrate. The two electrodes were arranged parallel to each other, with a distance between the electrodes of 10 mm (patterning evaluation substrate). After forming a predetermined organic film on the glass substrate, a patterning layer was formed only in region A using a metal mask so as to cover one of the ITO electrodes. The metal mask was then removed, and a metal electrode with a width of 10 mm was formed so as to be perpendicular to the ITO stripe electrode, thereby preparing a patterning evaluation element.

[0385] (Observation Conditions) Light emission observation and transmittance measurement were carried out for each of two pixels (area A and area B) of the patterning evaluation element.

[0386] (Preparation for Vacuum Deposition) The patterning evaluation substrate was subjected to ultrasonic cleaning using ultrapure water. Surface treatment was then performed using ozone ultraviolet cleaning. After cleaning and surface treatment, each layer was vacuum-deposited by vacuum deposition using a vacuum deposition method, and each layer was laminated. First, the glass substrate was placed in a vacuum deposition chamber, and 1.0 × 10 －４ The pressure was reduced to Pa. Then, each layer was formed according to the film formation conditions in the following order. Each organic material was formed into a film by resistance heating.

[0387] (Fabrication of Hole Injection Layer 3) Sublimation-purified N-[1,1'-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine and 1,2,3-tris[(4-cyano-2,3,5,6-tetrafluorophenyl)methylene]cyclopropane were mixed in a mass ratio of 99:1 to form a 10 nm film, thereby fabricating Hole Injection Layer 3. The film formation rate was 0.1 nm / sec.

[0388] (Preparation of First Hole Transport Layer) Sublimation-purified N-[1,1′-biphenyl]-4-yl-9,9-dimethyl-N-[4-(9-phenyl-9H-carbazol-3-yl)phenyl]-9H-fluoren-2-amine was formed into a film having a thickness of 85 nm at a rate of 0.2 nm / sec to prepare a first hole transport layer.

[0389] (Preparation of Second Hole Transport Layer) Sublimation-purified N-phenyl-N-(9,9-diphenylfluoren-2-yl)-N-(1,1'-biphenyl-4-yl)amine was formed into a film having a thickness of 5 nm at a rate of 0.15 nm / sec to prepare a second hole transport layer.

[0390] (Fabrication of Light-Emitting Layer 5) Sublimation-purified 3-(10-phenyl-9-anthryl)-dibenzofuran and 2,7-bis[N,N-di-(4-tertbutylphenyl)]amino-bisbenzofurano-9,9′-spirofluorene were mixed in a mass ratio of 95:5 to form a 30 nm film, thereby forming the light-emitting layer 5. The film formation rate was 0.1 nm / sec.

[0391] (Preparation of Hole Blocking Layer) Sublimation-purified 2-[3'-(9,9-dimethyl-9H-fluoren-2-yl)[1,1'-biphenyl]-3-yl]-4,6-diphenyl-1,3,5-triazine was deposited at a rate of 0.05 nm / sec to form a 6 nm thick film to prepare a hole blocking layer.

[0392] (Preparation of Electron Transport Layer 6) A 25 nm thick film of 6-[4′-(2-phenyl-6-quinolyl)biphenyl-4-yl]-2,4-diphenyl-1,3,5-triazine and 8-hydroxyquinolinolatolithium (hereinafter referred to as Liq) was formed in a mass ratio of 50:50 to prepare an electron transport layer 6. The film formation rate was 0.15 nm / sec.

[0393] (Fabrication of Cathode Patterning Layer 50) The cathode patterning layer 50 was fabricated by carrying out the following 1. Fabrication of Patterning Layer 7 and 2. Fabrication of Metal Electrode 8.

[0394] (1. Preparation of Patterned Layer 7) A patterned layer was formed using a metal mask with an opening of 10 mm × 10 mm. The metal mask was positioned so that the opening of the metal mask overlapped with region A. Subsequently, compound (Z25) was deposited to a thickness of 15 nm, and patterned layer 7 was prepared only in region A. The deposition rate was 0.1 nm / sec.

[0395] (2. Preparation of Metal Electrode 8) A 2 nm film of ytterbium and lithium fluoride (1 / 1) was formed at a deposition rate of 0.01 nm / sec, and then a 20 nm film of silver / magnesium (mass ratio 1 / 1) was formed. The deposition rate of the silver / magnesium film was 0.1 nm / sec.

[0396] (Preparation of Protective Layer 9) Sublimation-purified N4',N4'-diphenyl-N4',N4'-bis(9-phenyl-9H-carbazol-3-yl)-[1,1'-biphenyl]-4,4'-diamine was formed into a film of 50 nm at a rate of 0.05 nm / sec to prepare the protective layer 9. As a result, a 10 mm luminescence area was obtained as shown in FIG. ２ The organic electroluminescent device 100 was fabricated. The thickness of each film was measured using a stylus film thickness measuring instrument (DEKTAK, manufactured by Bruker).

[0397] (Luminescence observation) In region A where compound (Z25) was formed as a patterning layer, the formation of the metal electrode 8 was suppressed and no light was emitted. In region B where no patterning layer was formed, the metal electrode 8 was formed and light was emitted. It was confirmed that the electrode region 52 was formed.

[0398] (Transmittance Measurement) In region A where compound (Z25) was formed as a patterning layer, the formation of the metal electrode 8 was suppressed, and the transmittance was "≧90%". Region A was transparent, and it was confirmed that a transparent region 51 was formed. In region B where no patterning layer was formed, the metal electrode 8 was formed, and the transmittance was "≧20%".

[0399] 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.

[0400] REFERENCE SIGNS LIST 1 substrate 2 anode 3 hole injection layer 4 hole transport layer 5 light emitting layer 61 hole blocking layer 6 electron transport layer 7 patterning layer 8 metal electrode 81 electron injection layer 82 cathode 9 protective layer 50 cathode patterning layer 51 transparent region 52 electrode region 100 organic electroluminescent element

Claims

1. A material for metal patterning comprising a compound represented by the following formula (A2): In formula (A2), Z １ , Z ２ each independently represents an optionally substituted di- to tetravalent monocyclic, linked ring or fused ring di- to tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms, an optionally substituted di- to tetravalent monocyclic, linked ring or fused ring di- to tetravalent heteroaromatic group having 3 to 11 carbon atoms, an optionally substituted cyclic di- to tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, or an optionally substituted cyclic di- to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms. １ represents an optionally substituted monocyclic, linked ring or fused ring divalent aromatic hydrocarbon group having 6 to 26 carbon atoms, an optionally substituted monocyclic, linked ring or fused ring divalent heteroaromatic group having 3 to 26 carbon atoms, an optionally substituted cyclic divalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, an optionally substituted cyclic divalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, or a single bond. １ Each of G independently represents an optionally substituted pyridyl group or an optionally substituted pyrimidyl group. ２ each independently represents an optionally substituted pyridyl group, an optionally substituted pyrimidyl group, or an optionally substituted triazyl group. In formula (A2), a, b, d, and e each independently represent an integer of 1 to 3. In formula (A2), c represents an integer of 0 to 2. In formula (A2), R １ and R ２ are each independently represented by the following formula (B1). In formula (B1), L ２ represents O, S, a linear, branched or cyclic divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may be substituted with a fluorine atom, or a vinylene group which may be substituted with a fluorine atom and which may form a ring. In formula (B1), each f independently represents an integer of 0 to 4. In formula (B1), each g independently represents an integer of 1 to 4. In formula (B1), Rf １ each independently represents a mono- or divalent substituent having one or more carbon atoms and containing three or more fluorine atoms.

2. Z １ , Z ２ is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, each of these substituents independently is a linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, or a structure represented by formula (B1) (wherein these substituents may be further substituted with one or more substituents selected from the group consisting of these substituents).

3. If at least one of the following (a) or (b) is true: (a) G １ is a substituted pyridyl group or a substituted pyrimidyl group; ２ is a substituted pyridyl group, a substituted pyrimidyl group, or a substituted triazyl group, and the substituents of (a) and (b) are each independently a linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, or a structure represented by formula (B1) (wherein these substituents may be further substituted with one or more substituents selected from the group consisting of these substituents).

4. Z １ , Z ２ wherein each of the groups independently represents a di- to tetravalent aromatic hydrocarbon group having a structure in which phenyl or a plurality of benzene rings are linked or condensed, or a di- to tetravalent heteroaromatic group having a 5-membered ring, 6-membered ring, or a condensed structure thereof and a heteroatom is N, O, or S, and the heteroatom is a di- to tetravalent heteroaromatic group having a 5-membered ring, 6-membered ring, or a condensed structure thereof.

5. Z １ , Z ２ (a) a monocyclic, linked or fused ring divalent to tetravalent aromatic hydrocarbon group selected from the group consisting of benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, and groups formed by condensing any of these groups with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene; (b) a monocyclic, linked or fused ring divalent to tetravalent heteroaromatic group selected from the group consisting of pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, benzofuran, benzothiophene, benzodioxin, thiazole, thiadiazole, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and benzothiazole; (c) a cyclic divalent to tetravalent aliphatic hydrocarbon group selected from the group consisting of adamantane, diamantane, norbornene, and cyclohexane; or The material for metal patterning according to claim 1, wherein (d) is a cyclic divalent to tetravalent heteroaliphatic hydrocarbon group selected from the group consisting of morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane.

6. Z １ , Z ２ are each independently a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, each of which is independently a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a cyano group, a deuterium atom, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, or a structure represented by formula (B1) (wherein these substituents may be further substituted with one or more substituents selected from the group consisting of these substituents).

7. L １ is a monocyclic, linked or fused divalent aromatic hydrocarbon group having a structure in which phenyl or a plurality of benzene rings are linked or fused, or a monocyclic, linked or fused diheteroaromatic group in which the heteroatom is N, O or S and has a 5-membered ring, 6-membered ring or a structure in which these are fused.

8. L １ (a) a monocyclic, linked or fused divalent aromatic hydrocarbon group selected from the group consisting of benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, and groups formed by condensing any of these groups with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene; (b) a monocyclic, linked or condensed divalent heteroaromatic group selected from the group consisting of pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, and groups formed by condensing these groups with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene; (c) a cyclic divalent aliphatic hydrocarbon group selected from the group consisting of adamantane, diamantane, norbornene, and cyclohexane; or (d) a cyclic divalent heteroaliphatic hydrocarbon group selected from the group consisting of morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane.

9. L １ is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a cyclic heteroaliphatic hydrocarbon group, each of these substituents independently is a methyl group, a methoxy group, a trifluoromethyl group, a trifluoromethoxy group, an alkyl group having 2 to 10 carbon atoms, a fluorine atom, a phenyl group, a biphenylyl group, a naphthyl group, a phenanthryl group, a pyridyl group, a pyrimidyl group, a pyrazyl group, a triazyl group, an indolyl group, a carbazolyl group, a benzothienyl group, a dibenzothienyl group, a benzofuranyl group, a dibenzofuranyl group, a thiazolyl group, a benzothiazolyl group, or a structure represented by formula (B1) (wherein these substituents may be further substituted with one or more substituents selected from the group consisting of these substituents).

10. A heterocyclic compound represented by the following formula (A3): In formula (A3), Y １ , Y ２ each independently represents an optionally substituted di- to tetravalent monocyclic, linked ring or fused ring di- to tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms, an optionally substituted di- to tetravalent monocyclic, linked ring or fused ring di- to tetravalent heteroaromatic group having 3 to 11 carbon atoms, an optionally substituted cyclic di- to tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, or an optionally substituted cyclic di- to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms. ３ represents an optionally substituted monocyclic, linked ring or fused ring divalent aromatic hydrocarbon group having 6 to 26 carbon atoms, an optionally substituted monocyclic, linked ring or fused ring divalent heteroaromatic group having 3 to 26 carbon atoms, an optionally substituted cyclic divalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, an optionally substituted cyclic divalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, or a single bond. ３ Each of G independently represents an optionally substituted pyridyl group or an optionally substituted pyrimidyl group. ４ each independently represents an optionally substituted pyridyl group, an optionally substituted pyrimidyl group, or an optionally substituted triazyl group; In formula (A3), h and i each independently represent an integer of 1 to 3. In formula (A3), k and m each independently represent an integer of 2 to 3. In formula (A3), j represents an integer of 0 to 2. In formula (A3), R ３ and R ４ are each independently represented by the following formula (B2). In formula (B2), L ４ represents O, S, a linear, branched or cyclic divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may be substituted with a fluorine atom, or a vinylene group which may be substituted with a fluorine atom and which may form a ring. In formula (B2), each n is independently an integer of 0 to 4. In formula (B2), each p is independently an integer of 1 to 4. In formula (B2), Rf ２ each independently represents a mono- or divalent substituent having one or more carbon atoms and containing three or more fluorine atoms.

11. In formula (A3), Y １ , Y ２ The heterocyclic compound according to claim 10, wherein, when the substituents are each independently a linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, a structure represented by the above formula (B2), or a structure in which these substituents are further substituted with one or more substituents selected from the group consisting of these substituents.

12. In formula (A3), G ３ , G ４ The heterocyclic compound according to claim 10, wherein, when the substituents are each independently a linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, a structure represented by formula (B2), or a structure in which these substituents are further substituted with one or more substituents selected from the group consisting of these substituents.

13. In formula (A3), L ３ The heterocyclic compound according to claim 10, wherein, when the substituents are each independently a linear, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms, a linear, branched, or cyclic alkoxy group having 1 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, a heteroaromatic group having 3 to 20 carbon atoms, a cyano group, a fluorine atom, a deuterium atom, a structure represented by formula (B2), or a structure in which these substituents are further substituted with one or more substituents selected from the group consisting of these substituents.

14. Y １ , Y ２ The monocyclic, linked or condensed divalent to tetravalent aromatic hydrocarbon group represented by the following formula (1) is a structure in which phenyl or a plurality of benzene rings are linked or condensed, １ , Y ２ The heteroaromatic group having a monocyclic ring, a linked ring or a condensed ring, represented by the formula: １ , Y ２ The heterocyclic compound according to claim 10, wherein the cyclic divalent to tetravalent heteroaliphatic hydrocarbon group represented by the following formula (1) is a 5-membered ring, a 6-membered ring, a 7-membered ring, or a structure in which these are linked or condensed, and a heteroatom is N, O, or S.

15. In formula (A3), Y １ , Y ２ each of the compounds which provide a monocyclic, linked or condensed aromatic hydrocarbon group represented by the formula (I) is independently benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, or any of these groups condensed with one or more selected from the group consisting of benzene, naphthalene, and phenanthrene; １ , Y ２ each of the compounds which provide a monocyclic, linked or condensed heteroaromatic group represented by the formula (I) is independently pyridine, pyrimidine, pyrazine, triazine, furan, thiophene, benzofuran, benzothiophene, benzodioxin, thiazole, thiadiazole, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, or benzothiazole; １ , Y ２ each of the compounds which provide a cyclic divalent to tetravalent aliphatic hydrocarbon group represented by the formula: １ , Y ２ The heterocyclic compound according to claim 10, wherein each of the compounds providing the cyclic heteroaliphatic hydrocarbon group represented by the formula (I) is independently morpholine, piperidine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxine, 1,4-dithiane, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, or 1,4,7,10-tetraazacyclododecane.

16. In formula (A3), L ３ The monocyclic, linked or condensed divalent aromatic hydrocarbon group represented by the formula (I) is a phenyl group or a structure in which a plurality of benzene rings are linked or condensed, ３ The monocyclic, linked or condensed divalent heteroaromatic group represented by the formula (I) is a 5-, 6- or 7-membered ring, or a structure in which the heteroatom is N, O or S and the ring is linked or condensed thereto, ３ The heterocyclic compound according to claim 10, wherein the cyclic divalent heteroaliphatic hydrocarbon group represented by the following formula (1) is a 5-membered ring, a 6-membered ring, a 7-membered ring, or a structure in which the heteroatom is N, O, or S and the rings are linked or condensed.

17. In formula (A3), L ３ each of the compounds which provide a monocyclic, linked or condensed divalent aromatic hydrocarbon group represented by the formula (I) is independently benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, dibenzochrysene, or one or more of the above groups condensed with benzene, naphthalene, and phenanthrene; ３ each of the compounds which provide a monocyclic, linked or condensed divalent heteroaromatic group represented by the formula (I) is independently pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, acridine, dihydroacridine, phenoxazine, phenothiazine, dibenzo-1,4-dioxin, 1,2,3,4-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, or one or more of the above groups condensed with benzene, naphthalene, and phenanthrene; ３ Each of the compounds which provide a cyclic divalent aliphatic hydrocarbon group represented by the formula: ３ The heterocyclic compound according to claim 10, wherein each of the compounds providing a cyclic divalent heteroaliphatic hydrocarbon group represented by the formula (I) is independently morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxine, 1,4-dithiane, 4,4'-bipiperidine, 3,3'-bipiperidine, 2,2'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, or 1,4,7,10-tetraazacyclododecane.

18. A thin film for metal patterning comprising a material for metal patterning and capable of patterning a metal film or a metal laminate film, wherein the material for metal patterning comprises a material for metal patterning as defined in any one of claims 1 to 9, or a heterocyclic compound as defined in any one of claims 10 to 17, and the metal film or the metal laminate film contains one or more metals selected from the group consisting of lithium, ytterbium, magnesium, silver, and aluminum, or an alloy containing one or more of these metals.

19. The thin film for metal patterning according to claim 18, which has a water contact angle of 90° or more.

20. An organic electroluminescence element comprising a cathode, the cathode containing one or more metals selected from the group consisting of lithium, ytterbium, magnesium, silver, and aluminum, or an alloy containing one or more of these metals, and patterned with a metal patterning material, the metal patterning material containing a metal patterning material according to any one of claims 1 to 9, or a heterocyclic compound according to any one of claims 10 to 17.

21. A method for forming a metal pattern, comprising: a step of forming an organic material pattern containing a metal patterning material according to any one of claims 1 to 9, or a heterocyclic compound according to any one of claims 10 to 17; and a step of 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.

22. An electronic device comprising a metal patterning material according to any one of claims 1 to 9, or a heterocyclic compound according to any one of claims 10 to 17.

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