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

Abstract

To provide a material for metal patterning that can highly suppress formation of a metal thin film on a film surface, a thin film for metal patterning using the material for metal patterning, an organic electroluminescent element, a method for forming a metal pattern, and an electronic device.SOLUTION: There is provided a material for metal patterning which is represented by a formula (A1).SELECTED DRAWING: None

Description

[Technical field]

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

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

[0003] A known method for patterning a metal electrode is to form a patterned film of a metal patterning material with reduced metal adhesion as an underlayer, and then evaporate a metal from the underlayer. In this method, a metal film is selectively formed in the area where the metal patterning material is not formed, so that a metal electrode patterned in a desired shape can be formed.

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

[0005] [Patent Document 1] International Publication No. 2020 / 225778 Summary of the Invention [Problem to be solved by the invention]

[0006] However, in the method of Patent Document 1, it is difficult to form a pattern while highly suppressing the deposition of the metal in places other than the desired places. Furthermore, it is difficult to pattern metals other than magnesium with the compound described in Patent Document 1.

[0007] Therefore, one aspect of the present disclosure is directed to providing materials for metal patterning that can highly suppress the formation of various metal thin films on a film surface, thin films for metal patterning using these materials, organic electroluminescence elements, methods for forming metal patterns, and electronic devices. [Means for solving the problem]

[0008] According to one aspect of the present disclosure, a material for metal patterning represented by formula (A1) has been found, leading to the completion of the present invention.

[0009] [ka]

[0010] (In the formula, X 1 and X 2 are each independently an optionally substituted monocyclic, linked or fused ring divalent to tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms; an optionally substituted monocyclic, linked or fused di- to tetravalent heteroaromatic group having 3 to 26 carbon atoms; an optionally substituted cyclic divalent to tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, or It represents a cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms which may be substituted. E 1 and E 2 are each independently an optionally substituted monocyclic, linked or fused ring divalent to tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms; an optionally substituted monocyclic, linked or fused di- to tetravalent heteroaromatic group having 3 to 26 carbon atoms; an optionally substituted cyclic divalent to tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, or It represents a cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms which may be substituted. L 1 teeth, an optionally substituted monocyclic, linked or fused ring divalent aromatic hydrocarbon group having 6 to 26 carbon atoms; an optionally substituted monocyclic, linked or fused ring divalent heteroaromatic group having 3 to 26 carbon atoms; a cyclic divalent aliphatic hydrocarbon group having 3 to 18 carbon atoms which may be substituted; an optionally substituted cyclic divalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, or Represents a single bond. a, b, d, and e each independently represent an integer of 1 to 3. c represents an integer from 0 to 2. R 1 and R 2 each independently represents a group represented by the following formula (B1):

[0011] [ka]

[0012] L 2 teeth, 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 It represents a vinylene group which may be substituted with fluorine and which may form a ring. Each f independently represents an integer of 0 to 4. Each g independently represents an integer of 1 to 4. Each Rf independently represents a monovalent or divalent substituent having one or more carbon atoms and containing three or more fluorine atoms. Effect of the Invention

[0013] According to one aspect of the present disclosure, there can be provided a material for metal patterning that suppresses the formation of a metal thin film on a film surface, a thin film for metal patterning that uses the material, an organic electroluminescence element, a method for forming a metal pattern, and an electronic device. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0014] Hereinafter, a metal patterning material and an electronic device according to one embodiment of the present disclosure, as well as a method for forming a thin film for metal patterning, an organic electroluminescence element, and a metal pattern using the same will be described in detail. [First embodiment: material for metal patterning] A material for metal patterning according to one embodiment of the present disclosure is the following material containing a compound represented by formula (A1).

[0015] A material for metal patterning represented by formula (A1):

[0016] [ka]

[0017] (In the formula, X 1 and X 2 are each independently an optionally substituted monocyclic, linked or fused ring divalent to tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms; an optionally substituted monocyclic, linked or fused di- to tetravalent heteroaromatic group having 3 to 26 carbon atoms; an optionally substituted cyclic divalent to tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, or It represents a cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms which may be substituted. E 1 and E 2 are each independently an optionally substituted monocyclic, linked or fused ring divalent to tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms; an optionally substituted monocyclic, linked or fused di- to tetravalent heteroaromatic group having 3 to 26 carbon atoms; an optionally substituted cyclic divalent to tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, or It represents a cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms which may be substituted. L 1teeth, an optionally substituted monocyclic, linked or fused ring divalent aromatic hydrocarbon group having 6 to 26 carbon atoms; an optionally substituted monocyclic, linked or fused ring divalent heteroaromatic group having 3 to 26 carbon atoms; a cyclic divalent aliphatic hydrocarbon group having 3 to 18 carbon atoms which may be substituted; an optionally substituted cyclic divalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, or Represents a single bond. a, b, d, and e each independently represent an integer of 1 to 3. c represents an integer from 0 to 2. R 1 and R 2 each independently represents a group represented by the following formula (B1):

[0018] [ka]

[0019] L 2 teeth, 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 It represents a vinylene group which may be substituted with fluorine and which may form a ring. Each f independently represents an integer of 0 to 4. Each g independently represents an integer of 1 to 4. Each Rf independently represents a monovalent or divalent substituent having one or more carbon atoms and containing three or more fluorine atoms.

[0020] where X 1 , X 2 When is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, each of these groups independently represents 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 group represented by formula (B1), and It is preferable that these groups are substituted with one or more groups selected from the group consisting of a combination of these groups; E 1 , E 2 When is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, each of these groups independently represents 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 group represented by formula (B1), and It is preferable that these groups are substituted with one or more groups selected from the group consisting of a combination of these groups; L 1 When is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, each of these groups independently represents 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 group represented by formula (B1), and It is preferable that these groups are substituted with one or more groups selected from the group consisting of combinations of these groups.

[0021] R 1 and R 2are each independently represented by the following formula (B1):

[0022] [ka]

[0023] L 2 teeth, 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 represents a vinylene group which may be substituted with fluorine and which may form a ring; Each f independently represents an integer from 0 to 4; g each independently represents an integer from 1 to 4; Each Rf independently represents a mono- or divalent substituent having one or more carbon atoms and containing three or more fluorine atoms; Of the carbon atoms forming Rf, the ratio of the number 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.

[0024] The molecular structure represented by Rf is not particularly limited and may be linear, branched, or cyclic. Rf may be an aromatic or aliphatic compound, may contain O or S, or may be a combination of these.

[0025] The Rf preferably contains, as a partial structure with or without a fluorine atom, a linear, branched, or cyclic alkyl group, a linear, branched, or cyclic alkoxy group, a linear, branched, or cyclic alkenyl group, or a linear, branched, or cyclic alkenyloxy group. The cyclic alkyl group, cyclic alkoxy group, cyclic alkenyl group, or cyclic alkenyloxy group also includes those in which a ring carbon atom is substituted with an alkyl group or an alkenyl group, and the number of carbon atoms in the alkyl group or alkenyl group bonded to the ring carbon atom is preferably 1 to 6.

[0026] The cyclic alkyl group, cyclic alkoxy group, cyclic alkenyl group, or cyclic alkenyloxy group as a partial structure with or without a fluorine atom in Rf may be a monovalent group generated when one hydrogen atom is removed from a ring carbon atom, or may be a monovalent group generated when one hydrogen atom is removed from the above alkyl group or alkenyl group bonded to the ring carbon atom (i.e., a cycloalkylalkyl group, cycloalkylalkenyl group, cycloalkenylalkyl group, or cycloalkenylalkenyl group).

[0027] The linear, branched, or cyclic alkyl group as a partial structure of Rf, whether or not it has a fluorine atom, preferably includes 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, and alkyl groups that are structurally isomeric with these alkyl groups, as well as 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, in terms of excellent metal patterning performance, it is more preferable to include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, and alkyl groups that are structurally isomeric with these alkyl groups, as well as a cyclohexyl group, as a partial structure.

[0028] The alkoxy group as the partial structure of Rf with or without fluorine atom is preferably a linear, branched or cyclic alkyl group as the partial structure of Rf described above that contains an alkoxy group bonded to an oxygen atom. Among these groups, in terms of excellent metal patterning performance, it is more preferable to contain an alkoxy group as the partial structure that contains an alkoxy group bonded to an oxygen atom, which is a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, or an alkyl group that is structurally isomeric with these alkyl groups.

[0029] The linear, branched, or cyclic alkenyl group as a partial structure of Rf, which may or may not have a fluorine atom, preferably includes vinyl, 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, and alkenyl groups that are structurally isomeric with these alkenyl groups, as well as 1-cyclopropenyl, 1-cyclobutenyl, 1-cyclopentenyl, 1-cyclohexenyl, and cycloalkenyl groups that are structurally isomeric with these cycloalkenyl groups, etc. Among these groups, in terms of excellent metal patterning performance, it is more preferable to include vinyl, 1-propenyl, 1-butenyl, 1-pentenyl, 1-hexenyl, and alkenyl groups that are structurally isomeric with these alkenyl groups, as well as 1-cyclopentenyl, and 1-cyclohexenyl as partial structures.

[0030] The alkenyloxy as the partial structure of Rf with or without fluorine atom preferably includes an alkenyloxy group in which the linear, branched, or cyclic alkenyl group as the partial structure of Rf is bonded to an oxygen atom. Among these groups, in terms of excellent metal patterning performance, it is more preferable to include an alkenyloxy group in which a vinyl group, a 1-propenyl group, a 1-butenyl group, a 1-pentenyl group, a 1-hexenyl group, an alkenyl group that is structurally isomeric with these alkenyl groups, a 1-cyclopentenyl group, and a 1-cyclohexyl group are bonded to an oxygen atom as the partial structure.

[0031] Each Rf independently contains three or more fluorine atoms; It is more preferable that the alkyl group contains, as a partial structure, 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 that is structurally isomeric with these alkyl groups, as well as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a 1-methylcyclopentyl group, a cyclopentylmethyl group, a cyclohexyl group, and an adamantyl group.

[0032] The above Rf is preferably a structure represented by the following formula (001).

[0033] [ka]

[0034] During the ceremony, Rf 001 are each independently represents a linear, branched or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms and containing 3 or more fluorine atoms; L 001 are each independently a linear, branched or cyclic divalent aliphatic hydrocarbon group having 1 to 18 carbon atoms which may be substituted with O, S or a fluorine atom, or represents a vinylene group which may be substituted with fluorine and which may form a ring; a001 each independently represents an integer from 0 to 4; a002 each independently represents an integer from 1 to 4; Rf 001 are each independently such that the proportion of carbon atoms directly bonded to fluorine atoms among the carbon atoms forming the structure 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.

[0035] Rf 001 each independently contains three or more fluorine atoms; More preferred are methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, and alkyl groups that are structurally isomeric with these alkyl groups, as well as cyclopropyl, cyclobutyl, cyclopentyl, 1-methylcyclopentyl, cyclopentylmethyl, cyclohexyl, and adamantyl groups.

[0036] L 001 can suppress the formation of a metal film on the film surface, and therefore, O, S, or which may be substituted with a fluorine atom; methylene group, ethylene group, n-propylene group, n-butylene group, n-pentylene group, n-hexylene group, n-heptylene group, n-octylene group, and alkylene groups which are structurally isomeric with these alkylene groups, as well as cyclopropylene group, cyclobutylene group, cyclopentylene group, 1-methylpentylene group, cyclopentylmethyl group, cyclohexylene group, and adamantanediyl group, or A vinylene group which may form a ring is more preferable.

[0037] Each a001 independently is preferably 0 to 3, and more preferably 0 to 2.

[0038] Each a002 independently is preferably 1 to 3, and more preferably 1 or 2.

[0039] The number of carbon atoms in the structure represented by formula (001) is preferably 1 to 36, more preferably 1 to 30, even more preferably 1 to 24, even more preferably 1 to 20, particularly preferably 1 to 16. Especially more preferably 2 to 16. (Specific examples of formula (B1)) The formula (B1) can have, for example, the structures shown in the following (AAA1) to (AAA126).

[0040] In addition, the mark "*" used in the following structures indicates a binding site.

[0041] [ka]

[0042] [ka]

[0043] [ka]

[0044] [ka]

[0045] [ka]

[0046] [ka]

[0047] [ka]

[0048] [X 1 , X 2 ] X 1 and X 2 are each independently an optionally substituted monocyclic, linked or fused ring divalent to tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms; an optionally substituted monocyclic, linked or fused di- to tetravalent heteroaromatic group having 3 to 26 carbon atoms; an optionally substituted cyclic divalent to tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, or It represents a cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms which may be substituted. X 1 , X 2 A structure in which a monocyclic, linked, or condensed divalent to tetravalent aromatic hydrocarbon group represented by the following formula (1) is linked or condensed with phenyl or multiple benzene rings, A monocyclic, linked or condensed divalent to tetravalent heteroaromatic group, the heteroatom of which is N, O or S, and which is a 5-membered ring, a 6-membered ring or a condensed structure thereof; The cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms preferably has a heteroatom of N, O or S and has a 5-membered, 6-membered or 7-membered ring or a structure in which these are condensed. X 1 , X 2 Examples of compounds which provide a monocyclic, linked or fused ring divalent to tetravalent aromatic hydrocarbon group represented by the formula (I) include, independently of one another, 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 compounds which are fused to any of the above groups with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene; Examples of compounds which provide a monocyclic, linked, or fused divalent to tetravalent heteroaromatic group each independently include 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, or benzothiazole, as well as compounds in which any one or more of these groups are fused with a ring structure selected from the group consisting of benzene, naphthalene, and phenanthrene; The compounds which provide a cyclic divalent to tetravalent aliphatic hydrocarbon group are each independently adamantane, diamantane, or cyclohexane, More preferably, the compounds providing the cyclic divalent to tetravalent heteroaliphatic hydrocarbon groups are each 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, or 1,4,7,10-tetraazacyclododecane.

[0049] X 1 , X 2 The compounds which provide a monocyclic, linked or fused ring divalent to tetravalent aromatic hydrocarbon group represented by the formula: benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, or dibenzochrysene, and groups condensed with benzene or naphthalene; The compounds which provide a monocyclic, linked or fused divalent to tetravalent heteroaromatic group 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, or benzothiazole, and those groups condensed with benzene or naphthalene; the cyclic aliphatic hydrocarbon group is adamantane, diamantane, or cyclohexane; The compounds which provide a cyclic divalent to tetravalent heteroaliphatic hydrocarbon group are each independently More preferred are 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. X 1 , X 2 The compounds which provide a monocyclic, linked or fused ring divalent to tetravalent aromatic hydrocarbon group represented by the formula: benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, benzochrysene, or triptycene; The compounds which provide a monocyclic, linked, or fused divalent to tetravalent heteroaromatic group each independently include pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, 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, or benzothiazole, The compounds which provide a cyclic divalent to tetravalent aliphatic hydrocarbon group are each independently adamantane, diamantane, or cyclohexane, The compounds which provide a cyclic divalent to tetravalent heteroaliphatic hydrocarbon group are each independently Most preferred are piperazine, homopiperazine, hexahydro-1,3,5-triazine, 4,4'-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, or 1,4,7,10-tetraazacyclododecane.

[0050] X 1 , X 2 each of the substituents independently represents More preferably, it is one or more groups selected from the group consisting of 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 group represented by formula (B1), and a combination of these groups.

[0051] X 1 , X 2 each of the substituents independently represents More preferably, it is one or more groups selected from the group consisting of 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 group represented by formula (B1), and a combination of these groups.

[0052] X 1 , X 2 each of the substituents independently represents It is even more preferable that the alkyl group is one or more groups selected from the group consisting of 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, a group represented by formula (B1), and combinations of these groups.

[0053] X 1 , X 2 The substituents of each independently are A trifluoromethyl group, a trifluoromethoxy group, a structure represented by formula (B1), or a fluorine atom is most preferred. [E 1 , E 2 ] E 1 and E 2 are each independently an optionally substituted monocyclic, linked or fused ring divalent to tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms; an optionally substituted monocyclic, linked or fused di- to tetravalent heteroaromatic group having 3 to 26 carbon atoms; an optionally substituted cyclic divalent to tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, or It represents a cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms which may be substituted. E 1 , E 2 A structure in which a monocyclic, linked, or condensed divalent to tetravalent aromatic hydrocarbon group represented by the following formula (1) is linked or condensed with phenyl or multiple benzene rings, A monocyclic, linked or condensed divalent to tetravalent heteroaromatic group, the heteroatom of which is N, O or S, and which is a 5-membered ring, a 6-membered ring or a condensed structure thereof; The cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms preferably has a heteroatom of N, O or S and has a 5-membered, 6-membered or 7-membered ring or a structure in which these are condensed.

[0054] E 1 , E 2Examples of compounds which provide a monocyclic, linked or fused ring divalent to tetravalent aromatic hydrocarbon group represented by the formula (I) include, independently of one another, 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 compounds which are fused to any of the above groups with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene; Examples of compounds which provide a monocyclic, linked, or fused divalent to tetravalent heteroaromatic group each independently include 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, or benzothiazole, as well as compounds in which any one or more of these groups are fused with a ring structure selected from the group consisting of benzene, naphthalene, and phenanthrene; The compounds which provide a cyclic divalent to tetravalent aliphatic hydrocarbon group are each independently adamantane, diamantane, or cyclohexane, More preferably, the compounds providing the cyclic divalent to tetravalent heteroaliphatic hydrocarbon groups are each 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.

[0055] E 1 , E 2The compounds which provide a monocyclic, linked or fused ring divalent to tetravalent aromatic hydrocarbon group represented by the formula: benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, or dibenzochrysene, and groups condensed with benzene or naphthalene; The compounds which provide a monocyclic, linked or fused divalent to tetravalent heteroaromatic group 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, or benzothiazole, and those groups condensed with benzene or naphthalene; the cyclic aliphatic hydrocarbon group is adamantane, diamantane, or cyclohexane; The compounds which provide a cyclic divalent to tetravalent heteroaliphatic hydrocarbon group are each independently More preferred are 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. E 1 , E 2 The compounds which provide a monocyclic, linked or fused ring divalent to tetravalent aromatic hydrocarbon group represented by the formula: benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, benzochrysene, or triptycene; The compounds which provide a monocyclic, linked, or fused divalent to tetravalent heteroaromatic group each independently include pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thianthrene, 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, or benzothiazole, The compounds which provide a cyclic divalent to tetravalent aliphatic hydrocarbon group are each independently adamantane, diamantane, and cyclohexane, The compounds which provide a cyclic divalent to tetravalent heteroaliphatic hydrocarbon group are each independently 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.

[0056] E 1 , E 2 each of the substituents independently represents 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 formula (B1), Alternatively, it is more preferable that the group is one or more groups selected from the group consisting of a combination of these groups.

[0057] E 1 , E 2 each of the substituents independently represents 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 formula (B1), Alternatively, it is more preferable that the group is one or more groups selected from the group consisting of a combination of these groups.

[0058] E 1 , E 2 each of the substituents independently represents 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, a structure represented by formula (B1), Or, it is even more preferable that it is one or more groups selected from the group consisting of a combination of these groups.

[0059] E 1 , E 2 The substituents of each independently are A trifluoromethyl group, a trifluoromethoxy group, a structure represented by formula (B1), and a fluorine atom are most preferred. [X 1 , X 2 , E 1 , E 2 Specific examples of X 1 , X 2 , E 1 , E 2 For example, the following structures (AAB1) to (AAB563) can be used for the above. Note that the mark "*" used in the following structures indicates a binding site.

[0060] 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.

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[0083] [L 1 ] L 1 teeth, an optionally substituted monocyclic, linked or fused ring divalent aromatic hydrocarbon group having 6 to 26 carbon atoms; an optionally substituted monocyclic, linked or fused ring divalent heteroaromatic group having 3 to 26 carbon atoms; a cyclic divalent aliphatic hydrocarbon group having 3 to 18 carbon atoms which may be substituted; an optionally substituted cyclic divalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, or Represents a single bond. L 1 The monocyclic, linked, or condensed divalent aromatic hydrocarbon group represented by the formula (I) is a phenyl group or a structure in which multiple benzene rings are linked or condensed, the heteroatom of the monocyclic, linked or condensed divalent heteroaromatic group is N, O or S, and is preferably a 5-membered, 6-membered or 7-membered ring or a structure in which these are condensed; The cyclic divalent heteroaliphatic hydrocarbon group preferably has a heteroatom of N, O or S, and has a 5-membered ring, 6-membered ring or a condensed ring structure thereof.

[0084] L 1 The compounds which provide a monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group represented by the formula: benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, or dibenzochrysene, and these groups condensed with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene; The compounds which provide a monocyclic, linked ring, or fused ring divalent heteroaromatic group each independently include 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 / or benzothiazole, and those groups fused with one or more rings selected from the group consisting of benzene, naphthalene, and phenanthrene; The compounds which provide a cyclic divalent aliphatic hydrocarbon group are each independently adamantane, diamantane, norbornene, and cyclohexane; The compounds which provide a cyclic divalent heteroaliphatic hydrocarbon group are each independently More preferred are 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.

[0085] L 1 The compounds which provide a monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group represented by the formula: benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, or dibenzochrysene, and groups condensed with benzene or naphthalene; The compounds which provide a monocyclic, linked ring, or fused ring divalent heteroaromatic group each independently include 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, or benzothiazole, or any of these groups condensed with benzene or naphthalene The compounds which provide a cyclic divalent aliphatic hydrocarbon group are each independently Adamantane, diamantane, norbornene, and cyclohexane The compounds which provide a cyclic divalent heteroaliphatic hydrocarbon group are each independently More preferred are 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. L 1 The compounds which provide a monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group represented by the formula: Benzene, biphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, The compounds which provide a monocyclic, linked ring, or fused ring divalent heteroaromatic group each independently include 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, or benzothiazole, The compounds which provide a cyclic divalent aliphatic hydrocarbon group are each independently adamantane, diamantane, and cyclohexane, The compounds which provide a cyclic divalent heteroaliphatic hydrocarbon group are each independently Even more preferred are 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.

[0086] L 1 The compounds which provide a monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group represented by the formula: benzene, biphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, and phenanthrene; The compounds which provide a monocyclic, linked ring, or fused ring divalent heteroaromatic group each independently include 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, The compounds which provide a cyclic divalent aliphatic hydrocarbon group are each independently adamantane, diamantane, and cyclohexane, The compounds which provide a cyclic divalent heteroaliphatic hydrocarbon group are each independently 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.

[0087] L 1 is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted cyclic heteroaliphatic hydrocarbon group, each of these groups independently represents 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 (B1), and It is preferable that these groups are substituted with one or more groups selected from the group consisting of combinations of these groups.

[0088] L 1 each of the substituents independently represents It is more preferable that the alkyl group is substituted with one or more groups selected from the group consisting of 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 formula (B1), and combinations of these groups.

[0089] L 1 each of the substituents independently represents It is more preferable that the aryl group is substituted with one or more groups selected from the group consisting of 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 formula (B1), and groups formed by combining these groups.

[0090] L 1 each of the substituents independently represents It is even more preferable that the substituted group is one or more groups selected from the group consisting of 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, a structure represented by formula (B1), and groups formed by combining these groups.

[0091] L 1 each of the substituents independently represents A trifluoromethyl group, a trifluoromethoxy group, a structure represented by formula (B1), or a fluorine atom is most preferred.

[0092] Each a independently represents an integer of 1 to 3. Each a independently represents an integer of 1 to 2, preferably 1.

[0093] Each b independently represents an integer of 1 to 3. Each b independently represents an integer of 1 to 2, preferably 1.

[0094] Each d independently represents an integer of 1 to 3. Each d independently represents an integer of 1 to 2, preferably 2.

[0095] Each e independently represents an integer of 1 to 3. Each e independently represents an integer of 1 to 2, preferably 2. [L 1 Specific examples of L 1 For example, the structures shown in (AAB1) to (AAB215) above and the structures shown below can be adopted. [Specific examples of materials for metal patterning] As examples of the metal patterning material according to one embodiment of the present disclosure and the heterocyclic compound according to one embodiment of the present disclosure, compounds (Z1) to (Z45) are shown below, but the present disclosure is not limited to these compounds.

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[0101] [Thin films for metal patterning] A thin film for metal patterning according to one embodiment of the present disclosure includes a material for metal patterning, and is capable of patterning a metal film or a metal laminate film, The metal patterning material is The compound represented by formula (A1) The metal film or metal laminated film contains at least one selected from the group consisting of ytterbium, magnesium, silver, aluminum, and an alloy of magnesium and silver.

[0102] The metal patterning material contained in the thin film for metal patterning is the same as the above-mentioned metal patterning material, which contains the above-mentioned compound.

[0103] It is even more preferable that the water contact angles of the thin film for metal patterning are, in order, 90° or more, 91° or more, 92° or more, 93° or more, 94° or more, 95° or more, 96° or more, 97° or more, 98° or more, 99° or more, and 100° or more. [Organic electroluminescence element] An organic electroluminescence element according to one aspect of the present disclosure is an organic electroluminescence element including a cathode, The cathode is Contains at least one selected from the group consisting of ytterbium, magnesium, silver, aluminum, and an alloy of magnesium and silver, The metal patterning material is patterned, The metal patterning material comprises: The compound includes a compound represented by the formula (A1).

[0104] In the organic electroluminescence element, the metal patterning material used for patterning is the same as the above-mentioned metal patterning material containing the above-mentioned compound. [Metal pattern formation method] A method for forming a metal pattern according to one embodiment of the present disclosure includes the steps of: forming an organic material pattern including the metal patterning material; 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.

[0105] The metal patterning material is used by forming a film in the area where it is desired to suppress adhesion of the metal. Here, the area where it is desired to suppress adhesion of the metal material corresponds to the area where the organic material pattern is formed. Areas other than the area where it is desired to suppress adhesion of the metal material correspond to the area where the organic material pattern is not formed. The area where the organic material pattern is not formed is an area where adhesion of the metal material is promoted, and is the area where it is desired to form the metal pattern.

[0106] The method for forming the organic material pattern (film formation method) is not particularly limited, and known methods such as vacuum deposition, spin coating, casting, dip coating, die coating, bar code, offset, spray coating, inkjet, screen, offset, flexography, gravure, and microcontact can be applied. After film formation, the film may be annealed in a temperature environment higher than room temperature. There is also no particular limit to the film thickness of the organic material pattern.

[0107] 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.

[0108] The base on which the organic material pattern is formed may be either metallic or non-metallic, and examples of the base include organic films, metallic films, oxide films, inorganic films, etc. There are no particular limitations on the material of the substrate, and glass, plastic, metal, ceramic, and any other material can be used.

[0109] When the base on which the organic material pattern is formed is an organic film, for example, 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, phosphine oxide derivatives, etc. can be used. 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, an alkaline earth metal, a transition metal, or a metal of Group 13 of the periodic table, and examples thereof include lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, gold, silver, platinum, copper, iron, palladium, molybdenum, manganese, titanium, cobalt, nickel, tungsten, tin, and chromium, as well as alloys containing one or more of these metals. Examples of alloys include magnesium-silver alloy, magnesium-indium alloy, magnesium-aluminum alloy, indium-silver alloy, lithium-aluminum alloy, lithium-magnesium alloy, lithium-indium alloy, calcium-aluminum alloy, etc.

[0110] The method for forming the metal pattern is not particularly limited, and examples thereof include dry processes such as vacuum deposition and sputtering, and inkjet methods using metal nanoink, etc. Furthermore, there is no particular limit to the film thickness of the metal pattern.

[0111] By applying a metal material to the region where the organic material pattern is formed and the region where the organic material pattern is not formed, a film containing the metal material is instantaneously formed in both regions. However, since the adhesion of metal is suppressed in the region where the organic material pattern is formed, the metal pattern is naturally formed only in the region where the organic material pattern is not formed.

[0112] More specific examples of the method for forming the metal pattern include the following methods 1) and 2). 1) The above-mentioned metal patterning material is evaporated into a desired pattern using a metal mask or the like. 2) Then, metal is evaporated to form electrodes only on the areas where the metal patterning material is not deposited, i.e., negative metal electrodes are formed with respect to the deposition pattern of the metal patterning material.

[0113] 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.

[0114] A protective film may be provided on the patterned film obtained by patterning the metal. The protective film may be, for example, an organic film, an oxide film, an inorganic film, or the like, and is not particularly limited.

[0115] When the protective film is an organic film, for example, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aniline-based copolymers, conductive polymer oligomers (particularly thiophene oligomers), porphyrin compounds, aromatic tertiary amine compounds, carbazole compounds, styrylamine compounds, triazine derivatives, pyrimidine derivatives, etc. can be used. When the protective film is an inorganic film, for example, silicon nitride, silicon oxide, etc. can be used.

[0116] According to the metal patterning material and the metal pattern forming method according to one embodiment of the present disclosure, it is possible to pattern metal electrodes of solar cells, photosensors, image sensors, organic electroluminescence (EL) elements, organic solar cells, organic sensors, organic transistors, and the like, and to form metal wiring on a circuit board.

[0117] The metal patterning material according to one embodiment of the present disclosure can also be applied to a deposition process.

[0118] Furthermore, the metal patterning material according to one embodiment of the present disclosure has seven or more fluorine atoms in the molecule, which suppresses the formation of a thin metal film on the film surface. [Electronic equipment] The electronic device according to one embodiment of the present disclosure includes the above-mentioned metal patterning material. As described above, when forming the metal pattern, an organic material pattern including the metal patterning material is formed, so that the organic material pattern is formed together with the metal pattern. Therefore, the electronic device according to one embodiment of the present disclosure includes the organic material pattern including the metal patterning material together with the metal pattern.

[0119] 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, if the electronic device includes patterned metal electrodes or metal wiring on a circuit board, the electronic device according to this embodiment can be obtained by using the above-mentioned method for forming a metal pattern. Such electronic devices have a highly accurate metal pattern. [Example] 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.

[0120] The transmittance measurements were carried out using the following equipment. [Transmittance measurement] Measurement equipment: JASCO V-750 Measurement range: 550~800nm

[0121] Example 1 Synthesis of compound (Z16)

[0122] [ka]

[0123] In the reactor cooled to 0°C under a nitrogen atmosphere, sodium hydride (7.5mmol) was suspended in tetrahydrofuran (20ml) and stirred at 0°C. 4-(1,1,2,2,3,3,4,4,4-nonafluorobutyl)phenol (7.0mmol) was added dropwise to the suspension over 20 minutes. After the dropwise addition, perfluorobiphenyl (3.0mmol) dissolved in tetrahydrofuran (20ml) was added dropwise over 10 minutes. After the dropwise addition, the mixture was stirred at 75°C for 5 hours. 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 (Z16) as a white solid (yield 32%). The compounds were identified by FDMS measurement.

[0124] FDMS:918 Example 1' Evaluation of metal adhesion of compound (Z16) The glass substrate was boiled and cleaned (boiled and cleaned with isopropyl alcohol), then further cleaned with ultraviolet light and ozone, and then placed in a vacuum deposition apparatus. -4 The chamber was evacuated using a vacuum pump until the pressure in the chamber was reduced to less than Pa. Compound (Z16) 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. Silver was then deposited at a deposition rate of 0.1 nm / sec to form a 12 nm film. No silver was deposited on the area where compound (Z16) was deposited, and a transparent area of ​​2 mm x 1 mm was formed.

[0125] Example 2 Synthesis of compound (Z20)

[0126] [ka]

[0127] In the reactor cooled to 0°C under a nitrogen atmosphere, sodium hydride (7.5mmol) was suspended in tetrahydrofuran (20ml) and stirred at 0°C. 4-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctyl)phenol (7.0mmol) was added dropwise to the suspension over 20 minutes, and after the dropwise addition, perfluorobenzene (3.0mmol) dissolved in tetrahydrofuran (20ml) was added dropwise over 10 minutes. After the dropwise addition, the mixture was stirred at 75°C for 5 hours. 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 (Z20) as a white solid (yield 21%). The compounds were identified by FDMS measurement. FDMS:1322

[0128] Example 2' Evaluation of metal adhesion of compound (Z20) The glass substrate was boiled and cleaned (boiled and cleaned with isopropyl alcohol), then further cleaned with ultraviolet light and ozone, and then placed in a vacuum deposition apparatus. -4 The chamber was evacuated using a vacuum pump until the pressure was below 1 Pa. A 20 nm film of compound (Z20) 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. Then, 20 nm of silver and magnesium (1 / 9) were deposited at a deposition rate of 0.1 nm / sec. No silver or magnesium was deposited on the area where compound (Z20) was deposited, and a transparent area of ​​2 mm x 1 mm was formed.

[0129] Example 3 Synthesis of intermediate (I1)

[0130] [ka]

[0131] Under a nitrogen atmosphere, cyanuric chloride (5.0 mmol), 2,6-dibromo-4-pyridinol (20.0 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 desired intermediate (I1) as a white solid (yield 26%). The compounds were identified by FDMS measurement. FDM S:828.

[0132] Example 4 Synthesis of compound (Z31)

[0133] [ka]

[0134] Under a nitrogen atmosphere, intermediate I1 (4.0 mmol), tridecafluorohexyl iodide (48.0 mmol), and copper powder (50.0 mmol) were suspended in dimethyl sulfoxide (100 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 (Z31) as a white solid (yield 31%). The compounds were identified by FDMS measurement. FDM S:2268.

[0135] Example 4' Evaluation of metal adhesion of compound (Z31) The glass substrate was boiled and cleaned (boiled and cleaned with isopropyl alcohol), then further cleaned with ultraviolet light and ozone, and then placed in a vacuum deposition apparatus. -4The chamber was evacuated with a vacuum pump until the pressure dropped to below 1 Pa. A 100 nm film of compound (Z31) 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 lithium fluoride (1 / 1) were deposited at a deposition rate of 0.01 nm / sec to a thickness of 2 nm, followed by deposition of silver and magnesium (9 / 1) at a deposition rate of 0.1 nm / sec to a thickness of 12 nm. No films of ytterbium, lithium fluoride, silver, or magnesium were formed in the area where compound (Z31) was deposited, forming a transparent area of ​​2 mm x 1 mm.

[0136] Example 5 Synthesis of intermediate (I2)

[0137] [ka] Under a nitrogen atmosphere, 2,4,6-trichloropyrimidine (12.0 mmol), 1,3-adamantanediol (4.0 mmol), and cesium carbonate (9.0 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 desired intermediate (I2) as a white solid (yield 41%). The compounds were identified by FDMS measurement. FDM S:460.

[0138] Example 6 Synthesis of compound (Z53)

[0139] [ka]

[0140] Under a nitrogen atmosphere, intermediate I2 (4.0 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 (Z53) as a white solid (yield 54%). The compounds were identified by FDMS measurement. FDM S:2044.

[0141] Example 6' Evaluation of metal adhesion of compound (Z53) The glass substrate was boiled and cleaned (boiled and cleaned with isopropyl alcohol), then further cleaned with ultraviolet light and ozone, and then placed in a vacuum deposition apparatus. -4 The vacuum pump was used to evacuate the gas until the pressure in the chamber reached 10 Pa or less. A 30 nm film of compound (Z53) 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 had been placed. The metal mask was then removed, and 2 nm of ytterbium was deposited at a deposition rate of 0.01 nm / sec, followed by deposition of 15 nm of silver and magnesium (1 / 1) at a deposition rate of 0.1 nm / sec. No films of ytterbium, silver, or magnesium were formed in the area where compound (Z53) had been deposited, forming a transparent area of ​​2 mm x 1 mm.

[0142] Example 7 Synthesis of intermediate (I3)

[0143] [ka]

[0144] Under a nitrogen atmosphere, 2,4,6-tetrachloropyrimidine (16.0 mmol), 1H,1H,11H-eicosafluoro-1-undecanol (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 desired intermediate (I3) as a white solid (yield 54%). The compounds were identified by FDMS measurement. FDM S:1134.

[0145] Example 8 Synthesis of compound (Z26)

[0146] [ka]

[0147] Under a nitrogen atmosphere, intermediate I3 (6.0 mmol), 2,6-dihydroxynaphthalene (2.0 mmol), and cesium carbonate (5.0 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 (Z26) as a white solid (yield 38%). The compounds were identified by FDMS measurement. FDM S:2418.

[0148] Example 8' Evaluation of metal adhesion of compound (Z26) The glass substrate was boiled and cleaned (boiled and cleaned with isopropyl alcohol), then further cleaned with ultraviolet light and ozone, and then placed in a vacuum deposition apparatus. -4The chamber was evacuated using a vacuum pump until the pressure in the chamber was reduced to below 1 Pa. Compound (Z26) was deposited at a deposition rate of 0.2 nm / sec to form a 100 nm film on a glass substrate on which a metal mask with an opening of 2 mm x 1 mm was placed. 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 on which compound (Z26) was deposited, and a transparent area of ​​2 mm x 1 mm was formed.

[0149] Example 9 Synthesis of intermediate (I4)

[0150] [ka]

[0151] Under a nitrogen atmosphere, cyanuric chloride (24.0 mmol), 1,4-cyclohexanediol (10.0 mmol), and cesium carbonate (25.0 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 desired intermediate (I4) as a white solid (yield 64%). The compounds were identified by FDMS measurement. FDM S:410.

[0152] Example 10 Synthesis of compound (Z61)

[0153] [ka]

[0154] Under a nitrogen atmosphere, intermediate I4 (4.0 mmol), 1H,1H-tridecafluoro-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 (Z61) as a white solid (yield 59%). The compounds were identified by FDMS measurement. FDM S:1666.

[0155] Example 10' Evaluation of metal adhesion of compound (Z61) The glass substrate was boiled and cleaned (boiled and cleaned with isopropyl alcohol), then further cleaned with ultraviolet light and ozone, and then placed in a vacuum deposition apparatus. -4 The chamber was evacuated with a vacuum pump until the pressure in the chamber was reduced to below 1 Pa. A 30 nm film of compound (Z61) 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 had been placed. The metal mask was then removed, and lithium fluoride 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 10 nm. No lithium fluoride, silver, or magnesium was deposited on the area on which compound (Z61) had been deposited, forming a transparent area of ​​2 mm x 1 mm.

[0156] Example 11 Synthesis of compound (Z57)

[0157] [ka]

[0158] Under a nitrogen atmosphere, intermediate I3 (6.0 mmol), 1,4-anhydroerythritol (2.0 mmol), and cesium carbonate (5.0 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 (Z57) as a white solid (yield 38%). The compounds were identified by FDMS measurement. FDM S:2380.

[0159] Example 11' Evaluation of metal adhesion of compound (Z57) The glass substrate was boiled and cleaned (boiled and cleaned with isopropyl alcohol), then further cleaned with ultraviolet light and ozone, and then placed in a vacuum deposition apparatus. -4 The chamber was evacuated using a vacuum pump until the pressure in the chamber was reduced to below 1 Pa. Compound (Z57) was deposited at a deposition rate of 0.2 nm / sec to form a 100 nm film on a glass substrate with a metal mask having an opening of 2 mm x 1 mm. The metal mask was then removed, and silver was deposited at a deposition rate of 0.1 nm / sec to form a 30 nm film. No silver was deposited on the area where compound (Z57) was deposited, and a transparent area of ​​2 mm x 1 mm was formed.

[0160] Example 12 Synthesis of compound (Z65)

[0161] [ka]

[0162] Under a nitrogen atmosphere, intermediate I3 (6.0 mmol), 4,4'-bicyclohexanol (2.0 mmol), and cesium carbonate (5.0 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 (Z65) as a white solid (yield 29%). The compounds were identified by FDMS measurement.

[0163] FDM S:2474. Example 12' Evaluation of metal adhesion of compound (Z65) The glass substrate was boiled and cleaned (boiled and cleaned with isopropyl alcohol), then further cleaned with ultraviolet light and ozone, and then placed in a vacuum deposition apparatus. -4 The chamber was evacuated using a vacuum pump until the pressure in the chamber was reduced to below 1 Pa. A 100 nm film of compound (Z65) 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 had been placed. The metal mask was then removed, and aluminum was deposited at a deposition rate of 0.1 nm / sec to form an 8 nm film. No aluminum was deposited on the area on which compound (Z65) had been deposited, and a transparent area of ​​2 mm x 1 mm was formed.

[0164] Example 13 Synthesis of intermediate (I5)

[0165] [ka] Under a nitrogen atmosphere, 3,6-dihydroxybenzonorbornane (6.0 mmol), 2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (15.0 mmol), copper iodide (1.2 mmol), dimethylglycine (1.6 mmol), and tripotassium phosphate (15.0 mmol) were suspended in dimethyl sulfide (50 mL) and stirred at 50°C for 24 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 intermediate (I5) as a white solid (yield 29%).

[0166] Example 14 Synthesis of compound (Z66)

[0167] [ka]

[0168] Under a nitrogen atmosphere, intermediate I5 (4.0 mmol), heptadecafluorooctyl iodide (16.0 mmol), and copper powder (20.0 mmol) were suspended in dimethyl sulfoxide (100 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 (Z66) as a white solid (yield 34%). The compounds were identified by FDMS measurement. FDM S:1396.

[0169] Example 14' Evaluation of metal adhesion of compound (Z66) The glass substrate was boiled and cleaned (boiled and cleaned with isopropyl alcohol), then further cleaned with ultraviolet light and ozone, and then placed in a vacuum deposition apparatus. -4The chamber was evacuated with a vacuum pump until the pressure in the chamber was reduced to less than 1 Pa. A 100 nm film of compound (Z66) 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 had been placed. The metal mask was then removed, and 1 nm of ytterbium was deposited at a deposition rate of 0.01 nm / sec, followed by deposition of 10 nm of magnesium at a deposition rate of 0.1 nm / sec. No films of ytterbium or magnesium were formed in the area on which compound (Z66) had been deposited, forming a transparent area of ​​2 mm x 1 mm.

[0170] Example 15 Synthesis of intermediate (I6)

[0171] [ka]

[0172] Under a nitrogen atmosphere, 2,4,6-tetrachloropyrimidine (8.0 mmol), 8-bromo-2-dibenzofuranol (30.0 mmol), and cesium carbonate (30.0 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 desired intermediate (I6) as a white solid (yield 42%). The compounds were identified by FDMS measurement. FDM S:860.

[0173] Example 16 Synthesis of compound (Z40)

[0174] [ka]

[0175] Under a nitrogen atmosphere, intermediate I6 (4.0 mmol), heptadecafluorooctyl iodide (20.0 mmol), and copper powder (30.0 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 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 (Z40) as a white solid (yield 26%). The compounds were identified by FDMS measurement. FDM S:1880.

[0176] Example 16' Evaluation of metal adhesion of compound (Z40) The glass substrate was boiled and cleaned (boiled and cleaned with isopropyl alcohol), then further cleaned with ultraviolet light and ozone, and then placed in a vacuum deposition apparatus. -4 The chamber was evacuated using a vacuum pump until the pressure in the chamber was reduced to less than 1 Pa. A 100 nm film of compound (Z40) 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 had been placed. 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 silver being deposited at a deposition rate of 0.1 nm / sec to a thickness of 10 nm. No ytterbium or silver was deposited on the area on which compound (Z40) had been deposited, forming a transparent area of ​​2 mm x 1 mm.

[0177] Example 17 Synthesis of intermediate (I7)

[0178] [ka]

[0179] Under a nitrogen atmosphere, 2,4-dichloro-6-phenyl-1,3,5-triazine (8.0 mmol), 1,3-adamantanediol (25.0 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 desired intermediate (I7) as a white solid (yield 42%). The compounds were identified by FDMS measurement. FDM S:489.

[0180] Example 18 Synthesis of compound (Z50)

[0181] [ka]

[0182] Under a nitrogen atmosphere, intermediate I7 ​​(15.0 mmol), 3,3,4,4,5,5,6,6,9,9,10,10,11,11,12,12,12-heptadecafluoro-7-dodecene iodide (100.0 mmol), and tripotassium phosphate (100.0 mmol) were suspended in acetonitrile (50 mL) and stirred at 80 ° 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 (Z50) as a white solid (yield 28%). The compounds were identified by FDMS measurement. FDMS:1433

[0183] Example 18' Evaluation of metal adhesion of compound (Z50) The glass substrate was boiled and cleaned (boiled and cleaned with isopropyl alcohol), then further cleaned with ultraviolet light and ozone, and then placed in a vacuum deposition apparatus. -4The chamber was evacuated with a vacuum pump until the pressure was below 1 Pa. A 15 nm film of compound (Z50) 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 magnesium fluoride 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 10 nm. No films of magnesium fluoride, silver, or magnesium were formed on the part on which compound (Z50) was deposited, and a transparent area of ​​2 mm x 1 mm was formed.

[0184] Example 19 Synthesis of intermediate (I8)

[0185] [ka]

[0186] Under a nitrogen atmosphere, 2-(4-biphenylyl)4,6-dichloro-1,3,5-triazine (8.0 mmol), 1,4-anhydroerythritol (25.0 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 desired intermediate (I8) as a white solid (yield 34%).

[0187] Example 20 Synthesis of compound (Z46)

[0188] [ka]

[0189] Under a nitrogen atmosphere, intermediate I8 (15.0 mmol), 9H,9H,10H,10H-heptadecafluoro-10-iododecane (100.0 mmol), and tripotassium phosphate (100.0 mmol) were suspended in acetonitrile (50 mL) and stirred at 80°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 (Z46) as a white solid (yield 34%). The compounds were identified by FDMS measurement. FDMS:1329

[0190] Example 20' Evaluation of metal adhesion of compound (Z46) The glass substrate was boiled and cleaned (boiled and cleaned with isopropyl alcohol), then further cleaned with ultraviolet light and ozone, and then placed in a vacuum deposition apparatus. -4 The chamber was evacuated using a vacuum pump until the pressure in the chamber was reduced to below 1 Pa. Compound (Z46) was deposited at a deposition rate of 0.2 nm / sec to form a 100 nm film on a glass substrate on which a metal mask with an opening of 2 mm x 1 mm was placed. 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 on which compound (Z46) was deposited, and a transparent area of ​​2 mm x 1 mm was formed.

[0191] Comparative Example 1' (Evaluation of Metal Adhesion of Compound (X1)) The following compound (X1) was used as a material for metal patterning, and metal adhesion was evaluated.

[0192] [ka]

[0193] The adhesion of metal to compound (X1) was evaluated in the same manner as in Example 1'. A silver film was formed on the film of compound (X1), and no transparent region was formed.

[0194] Comparative Example 2 (Evaluation of Metal Adhesion of Compound (X2))

[0195] [ka]

[0196] The adhesion of metal to compound (X2) was evaluated in the same manner as in Example 1'. A silver film was formed on the film of compound (X2), and no transparent region was formed. Comparative Example 3' (Evaluation of Metal Adhesion of Compound (X3))

[0197] [ka]

[0198] The adhesion of metal to compound (X3) was evaluated in the same manner as in Example 1'. A silver film was formed on the film of compound (X3), and no transparent region was formed.

[0199] 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.

Claims

1. A material for metal patterning represented by formula (A1): 【Chemistry 1】 (In the formula, X １ and X ２ are each independently an optionally substituted monocyclic, linked or fused ring divalent to tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms; an optionally substituted di- to tetravalent monocyclic, linked or fused ring heteroaromatic group having 3 to 26 carbon atoms; an optionally substituted cyclic divalent to tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, or It represents a cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms which may be substituted. E １ and E ２ are each independently an optionally substituted monocyclic, linked or fused ring divalent to tetravalent aromatic hydrocarbon group having 6 to 26 carbon atoms; an optionally substituted di- to tetravalent monocyclic, linked or fused ring heteroaromatic group having 3 to 26 carbon atoms; an optionally substituted cyclic divalent to tetravalent aliphatic hydrocarbon group having 3 to 18 carbon atoms, or It represents a cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms which may be substituted. L １ teeth, an optionally substituted monocyclic, linked or fused ring divalent aromatic hydrocarbon group having 6 to 26 carbon atoms; an optionally substituted monocyclic, linked or fused ring divalent heteroaromatic group having 3 to 26 carbon atoms; a cyclic divalent aliphatic hydrocarbon group having 3 to 18 carbon atoms which may be substituted, an optionally substituted cyclic divalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms, or Represents a single bond. a, b, d, and e each independently represent an integer of 1 to 3. c represents an integer of 0 to 2. R １ and R ２ each independently represents a group represented by the following formula (B1). 【Chemistry 2】 L ２ teeth, 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 It represents a vinylene group which may be substituted with fluorine and which may form a ring. Each f independently represents an integer of 0 to 4. Each g independently represents an integer of 1 to 4. Each Rf independently represents a monovalent or divalent substituent having one or more carbon atoms and containing three or more fluorine atoms.

2. X １ , X ２ When is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, each of these groups independently represents 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 group represented by formula (B1), and 2. The metal patterning material according to claim 1, which is substituted with one or more groups selected from the group consisting of combinations of these groups.

3. E １ , E ２ When is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, each of these groups independently represents 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 group represented by formula (B1), and 2. The metal patterning material according to claim 1, which is substituted with one or more groups selected from the group consisting of combinations of these groups.

4. L １ When is a substituted aromatic hydrocarbon group, a substituted heteroaromatic group, a substituted aliphatic hydrocarbon group, or a substituted heteroaliphatic hydrocarbon group, each of these groups independently represents 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 group represented by formula (B1), and 2. The metal patterning material according to claim 1, which is substituted with one or more groups selected from the group consisting of combinations of these groups.

5. X １ , X ２ Represented by 2. The material for metal patterning according to claim 1, wherein the monocyclic, linked, or fused ring di- to tetra-valent aromatic hydrocarbon group has a structure in which phenyl or a plurality of benzene rings are linked or fused; the monocyclic, linked, or fused ring di- to tetra-valent heteroaromatic group has a heteroatom of N, O, or S and a 5-membered ring, 6-membered ring, or a condensed structure thereof; or the C3 to C18 cyclic di- to tetra-valent heteroaliphatic hydrocarbon group has a heteroatom of N, O, or S and a 5-membered ring, 6-membered ring, 7-membered ring, or a condensed structure thereof.

6. X １ , X ２ each of the compounds giving a monocyclic, linked or condensed divalent to tetravalent 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, or dibenzochrysene, and these groups are condensed with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene; the compounds providing a monocyclic, linked, or fused divalent to tetravalent heteroaromatic group 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, or benzothiazole, and these groups are fused with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene; The compounds providing a cyclic divalent to tetravalent aliphatic hydrocarbon group are each independently adamantane, diamantane, or cyclohexane, The material for metal patterning according to claim 1, wherein the compounds providing the cyclic divalent to tetravalent heteroaliphatic hydrocarbon group are each independently 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, or 1,4,7,10-tetraazacyclododecane.

7. X １ , X ２ each of the substituents independently represents 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 formula (B1), 2. The material for metal patterning according to claim 1, which is one or more groups selected from the group consisting of combinations of these groups.

8. E １ , E ２ a structure in which a monocyclic, linked or condensed divalent to tetravalent aromatic hydrocarbon group represented by the following formula (1) is linked or condensed with phenyl or a plurality of benzene rings; A monocyclic, linked or condensed divalent to tetravalent heteroaromatic group, the heteroatom being N, O or S, and having a 5-membered ring, 6-membered ring or a structure in which these are condensed; 2. The material for metal patterning according to claim 1, wherein the cyclic divalent to tetravalent heteroaliphatic hydrocarbon group having 3 to 18 carbon atoms has a heteroatom of N, O or S and has a structure of a 5-membered ring, a 6-membered ring, a 7-membered ring or a condensed ring thereof.

9. E １ , E ２ each of the compounds giving a monocyclic, linked or condensed divalent to tetravalent 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, or dibenzochrysene, and these groups are condensed with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene; the compounds providing a monocyclic, linked, or fused divalent to tetravalent heteroaromatic group 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, or benzothiazole, and these groups are fused with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene; The compounds providing a cyclic divalent to tetravalent aliphatic hydrocarbon group are each independently adamantane, diamantane, or cyclohexane, The material for metal patterning according to claim 1, wherein the compounds providing the cyclic divalent to tetravalent heteroaliphatic hydrocarbon group are each independently 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, or 1,4,7,10-tetraazacyclododecane.

10. E １ , E ２ each of the substituents independently represents 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 formula (B1), 2. The material for metal patterning according to claim 1, which is one or more groups selected from the group consisting of combinations of these groups.

11. L １ The monocyclic, linked, or condensed divalent aromatic hydrocarbon group represented by the formula (I) is a phenyl group or a structure in which multiple benzene rings are linked or condensed, The monocyclic, linked or condensed divalent heteroaromatic group has a heteroatom of N, O or S, and is a 5-, 6- or 7-membered ring or a condensed structure thereof, 2. The metal patterning material according to claim 1, wherein the cyclic divalent heteroaliphatic hydrocarbon group has a heteroatom selected from the group consisting of N, O and S, and has a structure of a 5-membered ring, a 6-membered ring or a condensed ring thereof.

12. L １ The compounds which provide a monocyclic, linked ring, or fused ring divalent aromatic hydrocarbon group represented by the formula: benzene, biphenyl, terphenyl, naphthalene, fluorene, spirobifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzofluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, chrysene, perylene, benzochrysene, triptycene, or dibenzochrysene, and these groups condensed with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene; The compounds which provide a monocyclic, linked ring, or fused ring divalent heteroaromatic group each independently include 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 / or benzothiazole, as well as those groups condensed with one or more members selected from the group consisting of benzene, naphthalene, and phenanthrene; The compounds which provide a cyclic divalent aliphatic hydrocarbon group are each independently adamantane, diamantane, norbornene, and cyclohexane; The compounds which provide a cyclic divalent heteroaliphatic hydrocarbon group are each independently 2. The material for metal patterning according to claim 1, which is 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, or 1,4,7,10-tetraazacyclododecane.

13. L １ each of the substituents independently represents 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 formula (B1), 2. The material for metal patterning according to claim 1, which is one or more groups selected from the group consisting of combinations of these groups.

14. A thin film for metal patterning, which contains a material for metal patterning and can pattern a metal film or a metal laminate film, The metal patterning material comprises a compound represented by formula (A1) of claim 1, The metal film or metal laminate film contains at least one selected from the group consisting of ytterbium, magnesium, silver, aluminum, and an alloy of magnesium and silver.

15. A thin film for metal patterning comprising the material for metal patterning according to claim 1 , which has a water contact angle of 90° or more.

16. An organic electroluminescence element comprising a cathode, The cathode is Contains at least one selected from the group consisting of ytterbium, magnesium, silver, aluminum, and an alloy of magnesium and silver, The metal patterning material is patterned, 2. An organic electroluminescence device, wherein the metal patterning material comprises a compound represented by formula (A1) according to claim 1.

17. Forming an organic material pattern comprising the metal patterning material according to any one of claims 1 to 13; 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.

18. An electronic device comprising the metal patterning material according to claim 1 .

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