Metal patterning material, pentafluorosulfenyl compound, metal patterning film, organic electroluminescent element, electronic device, and method for forming metal pattern

Abstract

This disclosure provides novel metal patterning materials, pentafluorosulfide-based compounds suitable for use with the materials, thin films for metal patterning using the materials or compounds, organic electroluminescent elements, electronic devices, and methods for forming metal patterns. The metal patterning material comprises a compound represented by the following formula (101). In formula (101), Y... 101 Each of these groups independently represents a monocyclic, cyclic, or fused-ring aromatic hydrocarbon group with 6 to 26 substituted carbon atoms; a monocyclic, cyclic, or fused-ring heteroaromatic hydrocarbon group with 3 to 26 substituted carbon atoms; a cyclic aliphatic hydrocarbon group with 3 to 8 substituted carbon atoms; or a monocyclic, cyclic, or fused-ring heteroaliphatic hydrocarbon group with 3 to 26 substituted carbon atoms. 101 Each can independently represent a cyclic aliphatic hydrocarbon group with 3 to 8 carbon atoms that can be substituted; a heteroaliphatic hydrocarbon group with 3 to 26 carbon atoms that can be substituted, consisting of monocyclic, cyclic, or fused rings; O, OR 101 , S, SR 101 、N(R 101 )2, or Si(R) 101 ) f 101 R 101 Bonded to oxygen, sulfur, or nitrogen atoms, each independently representing a monocyclic, cyclic, or fused-ring aromatic hydrocarbon group with 6 to 26 substituted carbon atoms; a heterocyclic aromatic hydrocarbon group with 3 to 26 substituted carbon atoms; a straight-chain, branched, or cyclic aliphatic hydrocarbon group with 1 to 18 substituted carbon atoms; a heterocyclic aliphatic hydrocarbon group with 3 to 26 substituted carbon atoms; a hydrogen atom; or formula (111), Rs 101 Each of the groups represented independently by the following formula (111) represents a group. 101 Each represents an integer from 1 to 6 independently, b 101 Each can independently represent an integer from 0 to 8, c 101 Each can independently represent an integer from 0 to 8, e 101 Each can independently represent an integer from 1 to 8. 101 Each independently represents an integer from 0 to 3. In the aforementioned equation (111), L 111 Each of these can independently represent a straight-chain, branched, or cyclic aliphatic hydrocarbon group having 1 to 18 carbon atoms that can be substituted; a straight-chain, branched, or cyclic alkenyl group having 1 to 18 carbon atoms that can be substituted; or a straight-chain, branched, or cyclic ethynyl group having 1 to 18 carbon atoms that can be substituted, X 111 Each can be represented independently as O, S, NH, or NR. 101 R 101Bonded to a nitrogen atom, each independently representing a monocyclic, intercyclic, or fused-ring aromatic hydrocarbon group with 6 to 26 substituted carbon atoms; a monocyclic, intercyclic, or fused-ring heteroaromatic hydrocarbon group with 3 to 26 substituted carbon atoms; a straight-chain, branched, or cyclic aliphatic hydrocarbon group with 1 to 18 substituted carbon atoms; a monocyclic, intercyclic, or fused-ring heteroaliphatic hydrocarbon group with 3 to 26 substituted carbon atoms; a hydrogen atom; or as stated in formula (111), indicating the bonding position, a 111 Each represents an integer from 1 to 6 independently, b 111 Each can independently represent an integer from 1 to 18, c 111 Each independently represents an integer from 1 to 2, d 111 Each can independently represent an integer from 0 to 1.

Description

Technical Field

[0001] This disclosure relates to metal patterning materials, pentafluorosulfur-based compounds suitable for use in the materials, thin films for metal patterning using the materials or compounds, organic electroluminescent elements, electronic devices, and methods for forming metal patterns. Background Technology

[0002] In recent years, organic electronic devices such as organic electroluminescent (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 the desired shapes.

[0003] As a method for patterning metal electrodes, one known method is to pattern a metal patterning material that inhibits metal adhesion as a substrate layer, form a film, and then deposit metal from above the substrate layer. In this method, since a metal film is selectively formed in the areas of the metal patterning material where no film has formed, a metal electrode patterned into a desired shape can be formed.

[0004] Patent document 1 discloses a technique for patterning magnesium metal using anthracene derivatives as metal patterning materials.

[0005] Existing technical documents Patent documents Patent Document 1: International Publication No. 2020 / 225778 Summary of the Invention

[0006] The technical problem that the invention aims to solve However, in the method described in Patent Document 1, it is difficult to effectively suppress the adhesion of metal to areas other than the desired location to form a pattern. Furthermore, it is difficult to achieve patterning of metals other than magnesium using the compound described in Document 1.

[0007] Technical solutions for solving technical problems In order to solve the above-mentioned technical problems, the inventors conducted repeated and in-depth research, and as a result, completed this invention.

[0008] That is, this disclosure includes the following implementation methods.

[0009] [1] A metal patterning material comprising a compound represented by the following formula (101).

[0010] [Chemistry 1]

[0011] In the aforementioned formula (101), Y 101Each of these terms independently represents a monocyclic, bicyclic, or fused-ring aromatic hydrocarbon group with 6 to 26 substituted carbon atoms; a monocyclic, bicyclic, or fused-ring heteroaromatic hydrocarbon group with 3 to 26 substituted carbon atoms; a cyclic aliphatic hydrocarbon group with 3 to 8 substituted carbon atoms; or a monocyclic, bicyclic, or fused-ring heteroaliphatic hydrocarbon group with 3 to 26 substituted carbon atoms. X 101 Each can independently represent a cyclic aliphatic hydrocarbon group with 3 to 8 substituted carbon atoms, a monocyclic, combined, or fused-ring heteroaliphatic hydrocarbon group with 3 to 26 substituted carbon atoms, O, OR 101 , S, SR 101 、N(R 101 )2, or Si(R) 101 ) f 101 , R 101 Bonded to oxygen, sulfur, or nitrogen atoms, each independently representing a monocyclic, intercyclic, or fused-ring aromatic hydrocarbon group with 6 to 26 substituted carbon atoms; a heterocyclic aromatic hydrocarbon group with 3 to 26 substituted carbon atoms; a straight-chain, branched, or cyclic aliphatic hydrocarbon group with 1 to 18 substituted carbon atoms; a heterocyclic aliphatic hydrocarbon group with 3 to 26 substituted carbon atoms; a hydrogen atom; or formula (111). Rs 101 Each of them independently represents the group shown in the following formula (111). a 101 Each can independently represent an integer from 1 to 6. b 101 Each can independently represent an integer from 0 to 8. c 101 Each can independently represent an integer from 0 to 8. e 101 Each can independently represent an integer from 1 to 8.

[0012] f 101 Each can independently represent an integer from 0 to 3.

[0013] [Chemistry 2]

[0014] In the aforementioned formula (111), L 111 Each can independently represent a straight-chain, branched, or cyclic aliphatic hydrocarbon group with 1 to 18 carbon atoms that can be substituted; a straight-chain, branched, or cyclic alkenyl group with 1 to 18 carbon atoms that can be substituted; or a straight-chain, branched, or cyclic ethynyl group with 1 to 18 carbon atoms that can be substituted. X111 Each can be independently represented as O, S, NH, or NR. 101 , R 101 Bonded to a nitrogen atom, each independently representing a monocyclic, bicyclic, or fused-ring aromatic hydrocarbon group with 6 to 26 substituted carbon atoms; a heterocyclic aromatic hydrocarbon group with 3 to 26 substituted carbon atoms; a straight-chain, branched, or cyclic aliphatic hydrocarbon group with 1 to 18 substituted carbon atoms; a heterocyclic aliphatic hydrocarbon group with 3 to 26 substituted carbon atoms; a hydrogen atom; or the formula (111) described above. Indicates the bonding location, a 111 Each can independently represent an integer from 1 to 6. b 111 Each can independently represent an integer from 1 to 18. c 111 Each can independently represent an integer from 1 to 2. d 111 Each can independently represent an integer from 0 to 1.

[0015] [2] According to the metal patterned material described in [1], wherein, in formula (101), Y 101 The aromatic hydrocarbon group shown has a phenyl group, or a structure formed by connecting or fused multiple benzene rings. Y 101 The heteroatoms in the heteroaromatic hydrocarbon group shown are N, O, or S, and the heteroaromatic hydrocarbon group has a 5-membered ring, a 6-membered ring, or a structure formed by their fusion. Y 101 The heteroatoms in the cyclic heteroaliphatic hydrocarbon group shown are N, O or S, and the cyclic heteroaliphatic hydrocarbon group has a 5-membered ring, a 6-membered ring, a 7-membered ring, an 8-membered ring, or a structure formed by their fusion.

[0016] [3] According to the metal patterned material described in [1] or [2], wherein, in formula (101), Provide Y 101 The aromatic hydrocarbon compounds shown are, independently, benzene, biphenyl, terphenyl, naphthalene, fluorene, spirodifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzo[a]fluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, β-, perylene, benzo[a]pyrene, triphenylene, dibenzo[a]pyrene, or compounds formed by fused together with one or more of benzene, naphthalene, and phenanthrene. Provide Y 101The heteroaromatic hydrocarbon compounds shown are, independently, pyridine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thiaanthracene, acridine, dihydroacridine, phenoxazine, phenthiazine, dibenzo-1,4-dioxin, 5,6,7,8-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, or compounds formed by fused to these compounds with one or more selected from benzene, naphthalene, and phenanthrene. Provide Y 101 The cyclic aliphatic hydrocarbon compounds shown are each independently adamantane, diadamantane, cyclopentane, cyclohexane, cycloheptane, or cyclooctane. Provide Y 101 The cyclic heteroaliphatic hydrocarbon compounds shown are, independently, morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiaane, 4,4′-bipiperidine, diazabicyclo[2,2,2]octane, and octahydro-1H-pyrrolo[3,4-b]pyridine, or 1,4,7,10-tetraazacyclododecane.

[0017] [4] The metal patterned material according to any one of [1] to [3], wherein, in formula (101), Y 101 The substituents are each independently: Methyl, methoxy, trifluoromethoxy, alkyl with 2-10 carbon atoms, cyano, deuterium, fluorine, chlorine, bromine, iodine, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, indoleyl, carbazoleyl, benzothiopheneyl, dibenzothiopheneyl, benzofuranyl, dibenzofuranyl, thiazolyl, benzothiazolyl, the structure shown in formula (111), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

[0018] [5] The metal patterned material according to any one of [1] to [4], wherein, in formula (101), X 101 The heteroatoms in the cyclic heteroaliphatic hydrocarbon group shown are N, O or S, and the cyclic heteroaliphatic hydrocarbon group has a 5-membered ring, a 6-membered ring, a 7-membered ring, an 8-membered ring or a structure formed by their fusion.

[0019] [6] The metal patterned material according to any one of [1] to [5], wherein, in formula (101), Provide X 101The cyclic aliphatic hydrocarbon compounds shown are each independently adamantane, diadamantane, norbornene, cyclopentane, cyclohexane, cycloheptane, or cyclooctane. Provide X 101 The cyclic heteroaliphatic hydrocarbon compounds shown are, 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.

[0020] [7] The metal patterned material according to any one of [1] to [6], wherein, in formula (101), X 101 The substituents are each independently: Methyl, methoxy, trifluoromethoxy, alkyl with 2-10 carbon atoms, cyano, deuterium, fluorine, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, indoleyl, carbazoleyl, benzothiopheneyl, dibenzothiopheneyl, benzofuranyl, dibenzofuranyl, thiazolyl, benzothiazolyl, the structure shown in formula (111), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

[0021] [8] The metal patterned material according to any one of [1] to [7], wherein, in formula (111), R 101 The aromatic hydrocarbon group shown has a phenyl group, or a structure formed by connecting or fused multiple benzene rings. R 101 The heteroatoms in the heteroaromatic hydrocarbon group shown are N, O, or S, and the heteroaromatic hydrocarbon group has a 5-membered ring, a 6-membered ring, or a structure formed by their fusion. R 101 The heteroatoms in the heteroaliphatic hydrocarbon group shown are N, O or S, and the heteroaliphatic hydrocarbon group has a 5-membered ring, a 6-membered ring, a 7-membered ring, an 8-membered ring, or a structure formed by their fusion.

[0022] [9] The metal patterned material according to any one of [1] to [8], wherein, in formula (111), Provide R 101 The aromatic hydrocarbon compounds shown are, independently, benzene, biphenyl, terphenyl, naphthalene, fluorene, spirodifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzo[a]fluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, β-, perylene, benzo[a]pyrene, triphenylene, dibenzo[a]pyrene, or compounds formed by fused together with one or more of benzene, naphthalene, and phenanthrene. Provide R101 The heteroaromatic hydrocarbon compounds shown are, independently, pyridine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thiaanthracene, acridine, dihydroacridine, phenoxazine, phenthiazine, dibenzo-1,4-dioxin, 5,6,7,8-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, or compounds formed by fused to these compounds with one or more selected from benzene, naphthalene, and phenanthrene. R 101 The aliphatic hydrocarbon groups shown are each independently: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptyl, octadecyl, nonadecanyl, carbazolyl, adamantyl, diadamantyl, cyclohexyl, or structures formed by further substitution of these groups with one or more groups selected from these groups. Provide R 101 The cyclic heteroaliphatic hydrocarbon compounds shown are, 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.

[0023]

[10] The metal patterned material according to any one of [1] to [9], wherein, in formula (111), R 101 The substituents are each independently: Methyl, methoxy, trifluoromethyl, trifluoromethoxy, alkyl with 2-10 carbon atoms, cyano, deuterium, fluorine, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, indoleyl, carbazoleyl, benzothiopheneyl, dibenzothiopheneyl, benzofuranyl, dibenzofuranyl, thiazolyl, benzothiazolyl, the structure shown in formula (111), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

[0024]

[11] The metal patterned material according to any one of [1] to

[10] , wherein, in formula (111), L 111The aliphatic hydrocarbon groups shown are each independently: methyl, ethyl, propane, butane, pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, heptane, octadecane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, or cyclooctane, or groups that have a structural isomeric relationship with these groups. L 111 The alkenyl groups shown are, independently, vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptenyl, octadecenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, or cyclooctenyl, or groups that have a structural isomeric relationship with these groups. L 111 The ethynyl group shown is: ethynyl, propynyl, butynyl, pentynyl, hexynyl, hepynyl, octyynyl, nonynyl, decynyl, undecynyl, dodeynyl, tridecynyl, tetradecynyl, decadecynyl, hexadecynyl, heptadecynyl, heptadecynyl, or octadecynyl, or a group that has a structural isomerism relationship with these groups.

[0025]

[12] The metal patterned material according to any one of [1] to

[11] , wherein, in formula (111), L 111 The substituents are each independently: Methyl, methoxy, trifluoromethoxy, alkyl groups with 2 to 10 carbon atoms, deuterium, chlorine, bromine, iodine, or The structure is formed by further substituting these groups with one or more groups selected from these groups.

[0026]

[13] The compound shown in the following formula (501).

[0027] [Chemistry 3]

[0028] In the above formula (501), Y 501 This refers to an aromatic hydrocarbon group with 6 to 26 substituted carbon atoms, consisting of a monocyclic, intercyclic, or fused ring; a heteroaromatic hydrocarbon group with 3 to 26 substituted carbon atoms; a cyclic aliphatic hydrocarbon group with 3 to 8 substituted carbon atoms; or a heteroaliphatic hydrocarbon group with 3 to 26 substituted carbon atoms. X 501This indicates cyclic aliphatic hydrocarbon groups with 3 to 8 substituted carbon atoms, monocyclic, combined, or fused heteroaliphatic hydrocarbon groups with 3 to 26 substituted carbon atoms, O, OR 501 , S, SR 501 、N(R 501 )2, or Si(R) 501 ) f 501 , R 501 Bonded to an oxygen, sulfur, or nitrogen atom, each independently representing a monocyclic, intercyclic, or fused-ring aromatic hydrocarbon group with 6 to 26 substituted carbon atoms; a heterocyclic aromatic hydrocarbon group with 3 to 26 substituted carbon atoms; a straight-chain, branched, or cyclic aliphatic hydrocarbon group with 1 to 18 substituted carbon atoms; a heterocyclic aliphatic hydrocarbon group with 3 to 26 substituted carbon atoms; a hydrogen atom; or the following formula (555). Rs 501 Each of them independently represents the group shown in the following formula (555). a 501 Each can independently represent an integer from 1 to 6. b 501 Each can independently represent an integer from 0 to 8. c 501 Each can independently represent an integer from 0 to 8. e 501 Each can independently represent an integer from 1 to 8. f 501 Each can independently represent an integer from 0 to 3.

[0029] [Chemistry 4]

[0030] In the aforementioned formula (555), L 555 Each can independently represent a straight-chain, branched, or cyclic aliphatic hydrocarbon group with 1 to 18 carbon atoms that can be substituted; a straight-chain, branched, or cyclic alkenyl group with 1 to 18 carbon atoms that can be substituted; or a straight-chain, branched, or cyclic ethynyl group with 1 to 18 carbon atoms that can be substituted. X 555 Each can be independently represented as O, S, NH, or NR. 501 , R 501Bonded to nitrogen, oxygen, sulfur, or silicon atoms, each independently representing a monocyclic, intercyclic, or fused-ring aromatic hydrocarbon group with 6 to 26 substituted carbon atoms; a heterocyclic aromatic hydrocarbon group with 3 to 26 substituted carbon atoms; a straight-chain, branched, or cyclic aliphatic hydrocarbon group with 1 to 18 substituted carbon atoms; a heterocyclic aliphatic hydrocarbon group with 3 to 26 substituted carbon atoms; a hydrogen atom; or the formula (555) stated above. Indicates the bonding location, a 555 Each can independently represent an integer from 1 to 6. b 555 Each can independently represent an integer from 1 to 18. c 555 Each can independently represent an integer from 1 to 2. d 555 Each can independently represent an integer from 0 to 1.

[0031] The compound represented by formula (501) has two or more structures of formula (555) within the molecule, or has one or more fluorine atoms outside of formula (555) within the molecule.

[0032]

[14] According to the compound described in

[13] , wherein, in formula (501), Y 501 The aromatic hydrocarbon group shown has a phenyl group, or a structure formed by connecting or fused multiple benzene rings. Y 501 The heteroatoms in the heteroaromatic hydrocarbon group shown are N, O, or S, and the heteroaromatic hydrocarbon group has a 5-membered ring, a 6-membered ring, or a structure formed by their fusion. Y 501 The heteroatoms in the heteroaliphatic hydrocarbon group shown are N, O or S, and the heteroaliphatic hydrocarbon group has a 5-membered ring, a 6-membered ring, a 7-membered ring or a structure formed by their fusion.

[0033]

[15] According to the compound described in

[13] or

[14] , wherein, in formula (501), Provide Y 501 The aromatic hydrocarbon compounds shown are, independently, benzene, biphenyl, terphenyl, naphthalene, fluorene, spirodifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzo[a]fluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, β-, perylene, benzo[a]pyrene, triphenylene, dibenzo[a]pyrene, or compounds formed by fused together with one or more of benzene, naphthalene, and phenanthrene. Provide Y 501The heteroaromatic hydrocarbon compounds shown are, independently, pyridine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thiaanthracene, acridine, dihydroacridine, phenoxazine, phenthiazine, dibenzo-1,4-dioxin, 5,6,7,8-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, or compounds formed by fused to these compounds with one or more selected from benzene, naphthalene, and phenanthrene. Provide Y 501 The cyclic aliphatic hydrocarbon compounds shown are each independently adamantane, diadamantane, cyclopentane, cyclohexane, cycloheptane, or cyclooctane. Provide Y 501 The cyclic heteroaliphatic hydrocarbon compounds shown are each independently morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiaane, 4,4′-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, or 1,4,7,10-tetraazacyclododecane.

[0034]

[16] The compound according to any one of

[13] to

[15] , wherein, in formula (501), Y 501 The substituents are each independently: Methyl, methoxy, trifluoromethoxy, alkyl with 2-10 carbon atoms, cyano, deuterium, fluorine, chlorine, bromine, iodine, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazineyl, indoleyl, carbazoleyl, benzothiopheneyl, dibenzothiopheneyl, benzofuranyl, dibenzofuranyl, thiazolyl, benzothiazolyl, structures shown in formula (555), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

[0035]

[17] The compound according to any one of

[13] to

[16] , wherein, in formula (501), X 501 The heteroatoms in the cyclic heteroaliphatic hydrocarbon groups with 3 to 18 carbon atoms shown are N, O, or S, and the cyclic heteroaliphatic hydrocarbon groups have 5-membered rings, 6-membered rings, 7-membered rings, 8-membered rings, or structures formed by their fusion.

[0036]

[18] The compound according to any one of

[13] to

[17] , wherein, in formula (501), Provide X 501The cyclic aliphatic hydrocarbon compounds shown are each independently adamantane, diadamantane, norbornene, cyclopentane, cyclohexane, cycloheptane, or cyclooctane. Provide X 501 The cyclic heteroaliphatic hydrocarbon compounds shown are, 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.

[0037]

[19] The compound according to any one of

[13] to

[18] , wherein, in formula (501), X 501 The substituents are each independently: Methyl, methoxy, trifluoromethoxy, alkyl with 2-10 carbon atoms, cyano, deuterium, fluorine, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, indoleyl, carbazoleyl, benzothiopheneyl, dibenzothiopheneyl, benzofuranyl, dibenzofuranyl, thiazolyl, benzothiazolyl, the structure shown in formula (555), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

[0038]

[20] The compound according to any one of

[13] to

[19] , wherein, in formula (501), R 501 The aromatic hydrocarbon group shown has a phenyl group, or a structure formed by connecting or fused multiple benzene rings. R 501 The heteroatoms in the heteroaromatic hydrocarbon group shown are N, O, or S, and the heteroaromatic hydrocarbon group has a 5-membered ring, a 6-membered ring, or a structure formed by their fusion. R 501 The heteroatoms in the cyclic heteroaliphatic hydrocarbon group shown are N, O or S, and the cyclic heteroaliphatic hydrocarbon group has a 5-membered ring, a 6-membered ring, a 7-membered ring, an 8-membered ring, or a structure formed by their fusion.

[0039]

[21] The compound according to any one of

[13] to

[21] , wherein, in formula (501), Provide R 501 The aromatic hydrocarbon compounds shown are, independently, benzene, biphenyl, terphenyl, naphthalene, fluorene, spirodifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzo[a]fluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, β-, perylene, benzo[a]pyrene, triphenylene, dibenzo[a]pyrene, or compounds formed by fused together with one or more of benzene, naphthalene, and phenanthrene. Provide R501 The heteroaromatic hydrocarbon compounds shown are, independently, pyridine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thiaanthracene, acridine, dihydroacridine, phenoxazine, phenthiazine, dibenzo-1,4-dioxin, 5,6,7,8-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, or compounds formed by fused to these compounds with one or more selected from benzene, naphthalene, and phenanthrene. R 501 The aliphatic hydrocarbon groups shown are each individually: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptyl, octadecyl, nonadecanyl, carbazolyl, adamantyl, diadamantyl, cyclohexyl, or structures formed by further substituting these groups with one or more groups selected from these groups. Provide R 501 The cyclic heteroaliphatic hydrocarbon compounds shown are, 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.

[0040]

[22] The compound according to any one of

[13] to

[21] , wherein, in formula (501), R 501 The substituents are each independently: Methyl, methoxy, trifluoromethyl, trifluoromethoxy, alkyl with 2-10 carbon atoms, cyano, deuterium, fluorine, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, carbazoleyl, benzothiopheneyl, dibenzothiopheneyl, benzofuranyl, dibenzofuranyl, thiazolyl, benzothiazolyl, the structure shown in formula (555), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

[0041]

[23] The compound according to any one of

[13] to

[22] , wherein, in formula (501), L 555The aliphatic hydrocarbon groups shown are: methylene, ethane, propane, butane, pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, heptane, octadecane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, or groups that have structural isomerism with these groups. L 555 The alkenyl groups shown are: vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptenyl, octadecenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, or groups that have structural isomerism with these groups. L 555 The ethynyl group shown is: ethynyl, propynyl, butynyl, pentynyl, hexynyl, hepynyl, octyynyl, nonynyl, decynyl, undecynyl, dodeynyl, tridecynyl, tetradecynyl, pentadecynyl, hexadecynyl, heptadecynyl, octadecynyl, or a group that has a structural isomerism relationship with these groups.

[0042]

[24] The compound according to any one of

[13] to

[23] , wherein the compound represented by formula (501) is the compound represented by formula (511), (531) or (541) below.

[0043] [Chemistry 5]

[0044] In equations (511), (531), or (541), Y 501 X 501 Rs 501 a 501 b 501 c 501 d 501 e 501 Synonymous with the definition recorded in any of

[13] to

[23] , n in the formula (531) 501 Represents integers from 1 to 12.

[0045]

[25] The compound according to any one of

[13] to

[23] , wherein the compound represented by formula (501) is the compound represented by formula (512) below.

[0046] [Chemistry 6]

[0047] In the above formula (512), Rs 501 a501 b 501 c 501 d 501 e 501 Synonymous with the definition recorded in any of

[13] to

[23] , m 501 Each of the integers from 1 to 6 can be represented independently, Y 501 Let A′ represent any one of the following equations (4-1) to (4-8). This represents a bonding bond.

[0048] [Chemistry 7]

[0049] In equations (4-1) to (4-8), R 401 ~R 410 Each is independently represented by a hydrogen atom; a deuterium atom; a fluorine atom; a bromine atom; a chlorine atom; a straight-chain, branched, or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms that can be replaced by a fluorine atom; a straight-chain, branched, or cyclic alkoxy group having 1 to 20 carbon atoms that can be replaced by a fluorine atom; a cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms that can be replaced by a monocyclic, bicyclic, or fused ring; an aromatic hydrocarbon group having 6 to 25 carbon atoms that can be replaced by a monocyclic, bicyclic, or fused ring; or a heteroaromatic group having 3 to 25 carbon atoms that can be replaced by a monocyclic, bicyclic, or fused ring; or the formula (555).

[0050]

[26] The compound according to any one of

[13] to

[23] , wherein the compound represented by formula (501) is the compound represented by formula (532) below.

[0051] [Chemistry 8]

[0052] In the aforementioned formula (532), Y 501 X 501 Rs 501 R 501 a 501 b 501 c 501 e 501 f 501 Synonymous with the definition recorded in any of

[13] to

[23] , m 501 Each of the above can independently represent an integer from 1 to 6, and each of A′ can independently represent any one of the following expressions (4-1) to (4-8). This represents a bonding bond.

[0053] [Chemistry 9]

[0054] In equations (4-1) to (4-8), R 401 ~R 410 Each is independently represented by a hydrogen atom; a deuterium atom; a fluorine atom; a bromine atom; a chlorine atom; a straight-chain, branched, or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms that can be replaced by a fluorine atom; a straight-chain, branched, or cyclic alkoxy group having 1 to 20 carbon atoms that can be replaced by a fluorine atom; a cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms that can be replaced by a monocyclic, bicyclic, or fused ring; an aromatic hydrocarbon group having 6 to 25 carbon atoms that can be replaced by a monocyclic, bicyclic, or fused ring; or a heteroaromatic group having 3 to 25 carbon atoms that can be replaced by a monocyclic, bicyclic, or fused ring; or the formula (555).

[0055]

[27] The compound according to any one of

[13] to

[23] , wherein the compound represented by formula (501) is a compound represented by formula (533), (534), (535) or (536).

[0056] [Chemistry 10]

[0057] In the formula, Y 501 Rs 501 R 501 a 501 b 501 e 501 Synonymous with the definition recorded in any of

[13] to

[23] , m 501 Each of the above can independently represent an integer from 1 to 6, and each of A′ can independently represent any one of the following expressions (4-1) to (4-8). This represents a bonding bond.

[0058] [Chemistry 11]

[0059] In equations (4-1) to (4-8), R 401 ~R 410 Each is independently represented by a hydrogen atom; a deuterium atom; a fluorine atom; a bromine atom; a chlorine atom; a straight-chain, branched, or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms that can be replaced by a fluorine atom; a straight-chain, branched, or cyclic alkoxy group having 1 to 20 carbon atoms that can be replaced by a fluorine atom; a cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms that can be replaced by a monocyclic, bicyclic, or fused ring; an aromatic hydrocarbon group having 6 to 25 carbon atoms that can be replaced by a monocyclic, bicyclic, or fused ring; or a heteroaromatic group having 3 to 25 carbon atoms that can be replaced by a monocyclic, bicyclic, or fused ring; or the formula (555).

[0060]

[28] The compound according to any one of

[13] to

[23] , wherein the compound represented by formula (501) is the compound represented by formula (542) below.

[0061] [Chemistry 12]

[0062] In the formula, Rs 501 R 501 a 501 e 501 f 501 Synonymous with the definition recorded in any of

[13] to

[23] , n 501 m represents integers from 1 to 12. 501 Each of the above can independently represent an integer from 1 to 6, and each of A′ can independently represent any one of the following expressions (4-1) to (4-8). Representing a bond, C′ is composed of O, NH, N (R 501 )f 501 , S, Si(R 501 )f 501 express.

[0063] [Chemistry 13]

[0064] In equations (4-1) to (4-8), R 401 ~R 410 Each is independently represented by a hydrogen atom; a deuterium atom; a fluorine atom; a bromine atom; a chlorine atom; a straight-chain, branched, or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms that can be replaced by a fluorine atom; a straight-chain, branched, or cyclic alkoxy group having 1 to 20 carbon atoms that can be replaced by a fluorine atom; a cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms that can be replaced by a monocyclic, bicyclic, or fused ring; an aromatic hydrocarbon group having 6 to 25 carbon atoms that can be replaced by a monocyclic, bicyclic, or fused ring; or a heteroaromatic group having 3 to 25 carbon atoms that can be replaced by a monocyclic, bicyclic, or fused ring; or the formula (555).

[0065]

[29] The compound according to any one of

[13] to

[23] , wherein the compound represented by formula (501) is the compound represented by formula (543) below.

[0066] [Chemistry 14]

[0067] In the aforementioned equation (543), Rs 501 a 501 e 501 Synonymous with the definition recorded in any of

[13] to

[23] , n501 m represents integers from 1 to 12. 501 Each of the above can independently represent an integer from 1 to 6, and each of A′ can independently represent any one of the following expressions (4-1) to (4-8). Representing a bond, C′ is composed of O, NH, N (R 501 )f 501 , S, Si(R 501 )f 501 express.

[0068] [Chemistry 15]

[0069] In equations (4-1) to (4-8), R 401 ~R 410 Each is independently represented by a hydrogen atom; a deuterium atom; a fluorine atom; a bromine atom; a chlorine atom; a straight-chain, branched, or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms that can be replaced by a fluorine atom; a straight-chain, branched, or cyclic alkoxy group having 1 to 20 carbon atoms that can be replaced by a fluorine atom; a cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms that can be replaced by a monocyclic, bicyclic, or fused ring; an aromatic hydrocarbon group having 6 to 25 carbon atoms that can be replaced by a monocyclic, bicyclic, or fused ring; or a heteroaromatic group having 3 to 25 carbon atoms that can be replaced by a monocyclic, bicyclic, or fused ring; or the formula (555).

[0070]

[30] The compound according to any one of

[25] to

[29] , wherein each of the formulas A′ is independently represented by any one of the following formulas (6-1) to (6-36).

[0071] [Chemistry 16]

[0072] [Chemistry 17]

[0073] [Chemistry 18]

[0074] [Chemistry 19]

[0075] In the formulas (6-1) to (6-36), R 501 ~R 586Each can be represented independently as: hydrogen atom; deuterium atom; fluorine atom; bromine atom; chlorine atom; a straight-chain or branched aliphatic hydrocarbon group with 1 to 4 carbon atoms; a straight-chain or branched alkoxy group with 1 to 4 carbon atoms that can be substituted by a fluorine atom; a cyclic aliphatic hydrocarbon group with 5 to 20 carbon atoms that can be substituted; a cyclic heteroaliphatic hydrocarbon group with 3 to 20 carbon atoms that can be substituted; an aromatic hydrocarbon group with 6 to 20 carbon atoms that can be substituted; or a heteroaromatic group with 3 to 20 carbon atoms that can be substituted. L 601 ~L 660 Each of these elements independently represents a straight-chain or branched divalent aliphatic hydrocarbon group, oxygen atom, sulfur atom, or single bond with 1 to 4 carbon atoms. L 701 ~L 760 Each of these elements independently represents a straight-chain or branched divalent aliphatic hydrocarbon group, oxygen atom, sulfur atom, or single bond with 1 to 4 carbon atoms. p and q each independently represent integers from 0 to 11. This represents a bonding bond.

[0076]

[31] A metal patterning film comprising any one of the metal patterning materials described in [1] to

[12] , or comprising a metal patterning material containing any one of the compounds described in

[13] to

[30] , capable of patterning metal films or metal laminates.

[0077]

[32] According to the metal patterning film described in

[31] , the water contact angle of the metal patterning film is 90° or more.

[0078]

[33] An organic electroluminescent element having a cathode, The cathode contains at least one element selected from ytterbium, magnesium, silver, lithium, aluminum, and alloys of magnesium and silver. The cathode is patterned with any one of the metal patterning materials described in [1] to

[12] , or with a metal patterning material containing any one of the compounds described in

[13] to

[30] .

[0079]

[34] A method for forming a metal pattern, comprising: The process of forming an organic material pattern on a substrate using any one of the metal patterning materials described in [1] to

[12] , or a metal patterning material containing any one of the compounds described in

[13] to

[30] ; and The process of applying a metallic material to the forming area and the non-forming area of ​​the organic material pattern to form a metallic pattern on the non-forming area.

[0080]

[35] An electronic device comprising a metal patterned material as described in any one of [1] to

[12] , or a metal patterned material comprising a compound as described in any one of

[13] to

[30] .

[0081] Invention Effects According to one aspect of the present invention, there are provided metal patterning materials capable of highly suppressing the formation of various metal thin films on the film surface, pentafluorosulfur-based compounds suitable for use in the materials, thin films for metal patterning using the same, organic electroluminescent elements, methods for forming metal patterns, and electronic devices. Attached Figure Description

[0082] Figure 1 This is a graph showing the results of the transmittance measurement in Example 102.

[0083] Figure 2 This is a graph showing the results of the transmittance measurement of comparative example (X1).

[0084] Figure 3 This is a graph showing the results of the transmittance measurement of comparative example (X1).

[0085] Figure 4 This is a graph showing the results of the transmittance measurement for the reference example.

[0086] Figure 5 This is a schematic cross-sectional view showing an example of the structure of an organic electroluminescent element.

[0087] Figure 6 It means Figure 1 A schematic cross-sectional view of an example of the formation of a cathode patterned layer.

[0088] Figure 7 It means Figure 1 A schematic top view of an example of the composition of a cathode patterned layer. Detailed Implementation

[0089] [First method: Metal patterned material (101)] One aspect of this disclosure relates to a metal patterning material comprising a compound represented by the following formula (101).

[0090] [Chemistry 20]

[0091] In the aforementioned formula (101), Y 101Each of these terms independently represents a monocyclic, bicyclic, or fused-ring aromatic hydrocarbon group with 6 to 26 substituted carbon atoms; a monocyclic, bicyclic, or fused-ring heteroaromatic hydrocarbon group with 3 to 26 substituted carbon atoms; a cyclic aliphatic hydrocarbon group with 3 to 8 substituted carbon atoms; or a monocyclic, bicyclic, or fused-ring heteroaliphatic hydrocarbon group with 3 to 26 substituted carbon atoms. X 101 Each can independently represent a cyclic aliphatic hydrocarbon group with 3 to 8 substituted carbon atoms, a monocyclic, combined, or fused-ring heteroaliphatic hydrocarbon group with 3 to 26 substituted carbon atoms, O, OR 101 , S, SR 101 、N(R 101 )2, or Si(R) 101 ) f 101 , R 101 Bonded to oxygen, sulfur, or nitrogen atoms, each independently representing a monocyclic, intercyclic, or fused-ring aromatic hydrocarbon group with 6 to 26 substituted carbon atoms; a heterocyclic aromatic hydrocarbon group with 3 to 26 substituted carbon atoms; a straight-chain, branched, or cyclic aliphatic hydrocarbon group with 1 to 18 substituted carbon atoms; a heterocyclic aliphatic hydrocarbon group with 3 to 26 substituted carbon atoms; a hydrogen atom; or the following formula (111), Rs 101 Each of them independently represents the group shown in the following formula (111). a 101 Each can independently represent an integer from 1 to 6. b 101 Each can independently represent an integer from 0 to 8. c 101 Each can independently represent an integer from 0 to 8. e 101 Each can independently represent an integer from 1 to 8. f 101 Each can independently represent an integer from 0 to 3.

[0092] [Chemistry 21]

[0093] In the aforementioned formula (111), L 111 Each can independently represent a straight-chain, branched, or cyclic aliphatic hydrocarbon group with 1 to 18 carbon atoms that can be substituted; a straight-chain, branched, or cyclic alkenyl group with 1 to 18 carbon atoms that can be substituted; or a straight-chain, branched, or cyclic ethynyl group with 1 to 18 carbon atoms that can be substituted. X 111Each can be independently represented as O, S, NH, or NR. 101 , R 101 Bonded to a nitrogen atom, each independently representing a monocyclic, bicyclic, or fused-ring aromatic hydrocarbon group with 6 to 26 substituted carbon atoms; a heterocyclic aromatic hydrocarbon group with 3 to 26 substituted carbon atoms; a straight-chain, branched, or cyclic aliphatic hydrocarbon group with 1 to 18 substituted carbon atoms; a heterocyclic aliphatic hydrocarbon group with 3 to 26 substituted carbon atoms; a hydrogen atom; or the formula (111) described above. Indicates the bonding location, a 111 Each can independently represent an integer from 1 to 6. b 111 Each can independently represent an integer from 1 to 18. c 111 Each can independently represent an integer from 1 to 2. d 111 Each can independently represent an integer from 0 to 1.

[0094] Wherein, the compound represented by formula (501) has two or more structures of formula (555) within the molecule, or has one or more fluorine atoms in addition to formula (555) within the molecule.

[0095] (Rs 101 (Preferred method) In the above formula (101), Rs 101 Each is independently represented by the aforementioned equation (111).

[0096] In formula (111), SF5 represents pentafluorothioyl, which is a structure with five fluorine atoms bonded to sulfur atoms, as represented by formula (222).

[0097] [Chemistry 22]

[0098] In the above formula (111), L 111 The molecular structure of the shown groups is not particularly limited and can be any of the following: linear, branched, or cyclic.

[0099] As L 111The aliphatic hydrocarbon groups shown are not particularly limited, and can be listed independently as follows: methylene, ethane, propane, butane, pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, heptane, octadecane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, or groups that have structural isomerism with these groups.

[0100] As L 111 The alkenyl groups shown are not particularly limited, and can be individually exemplified by: vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptenyl, octadecenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, or groups that have structural isomerism with these groups.

[0101] As L 111 The ethynyl group shown is not particularly limited, and can be exemplified independently by, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, hepynyl, octyynyl, nonynyl, decynyl, undecynyl, dodeynyl, tridecynyl, tetradecynyl, decaynyl, hexadecynyl, heptadecynyl, octadecynyl, or groups that have structural isomerism with these groups.

[0102] To improve patterning performance As L 111 The aliphatic hydrocarbon groups shown are preferably: methylene, ethane, propane, butane, pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, cyclobutane, cyclopentane, cyclohexane, or groups that have a structural isomeric relationship with these groups. As L 111 The alkenyl groups shown are preferably: vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, or groups that have structural isomerism with these groups. As L 111 The acetylenic group shown is preferably: acetylenic, propynyl, butynyl, pentynyl, hexynyl, hepynyl, octylenyl, nonynyl, decynyl, undecynyl, dodecaynyl, tridecaynyl, tetradecaynyl, decadecynyl, or a group that has a structural isomerism relationship with these groups.

[0103] To further improve patterning performance As L 111The aliphatic hydrocarbon groups shown are more preferably: methylene, ethane, propane, butane, pentane, hexane, heptane, octane, nonane, decane, cyclopentane, cyclohexane, or groups that have a structural isomeric relationship with these groups. As L 111 The alkenyl groups shown are more preferably: vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, or groups that have a structural isomeric relationship with these groups. As L 111 The acetylenic group shown is more preferably: acetylenic, propynyl, butynyl, pentylenic, or a group that has a structural isomer relationship with these groups.

[0104] To further improve patterning performance, As L 111 The aliphatic hydrocarbon groups shown are further preferably: methylene, ethane, propane, butane, pentane, hexane, heptane, cyclopentane, cyclohexane, or groups that have a structural isomeric relationship with these groups. As L 111 The alkenyl group shown is further preferably: vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, hexadecenyl, heptadecanyl, or a group having a structural isomeric relationship with these groups. As L 111 The acetylenic group shown is further preferably acetylenic, propynyl, butynyl, or a group that has a structural isomer relationship with these groups.

[0105] In the aforementioned equation (111), L is used as... 111 The substituents are not particularly limited, and examples can be given independently: Methyl, methoxy, trifluoromethoxy, alkyl groups with 2 to 10 carbon atoms, deuterium, chlorine, bromine, iodine, or The structure is formed by further substituting these groups with one or more groups selected from these groups.

[0106] (Concrete example of formula (111)) As an example of formula (111), the structures shown in (AAA1) to (AAA198) below can be cited. It should be noted that the notation “…” used in the following structures… "Indicates the bonding site.

[0107] [Chemistry 23]

[0108] [Chemistry 24]

[0109] [Chemistry 25]

[0110] [Chemistry 26]

[0111] [Chemistry 27]

[0112] [Chemistry 28]

[0113] [Chemistry 29]

[0114] [Chemistry 30]

[0115] [Chemistry 31]

[0116] [Chemistry 32]

[0117] [Chemistry 33]

[0118] (Y 101 (Preferred method) In the aforementioned formula (101), Y 101 Each can independently represent a monocyclic, bicyclic, or fused-ring aromatic hydrocarbon group with 6 to 26 substituted carbon atoms; a heterocyclic aromatic hydrocarbon group with 3 to 26 substituted carbon atoms; a cyclic aliphatic hydrocarbon group with 3 to 8 substituted carbon atoms; or a heterocyclic aliphatic hydrocarbon group with 3 to 26 substituted carbon atoms.

[0119] As Y 101 The aromatic hydrocarbon group shown has a phenyl group, or a structure formed by connecting or fused multiple benzene rings. As Y 101 The heteroaromatic hydrocarbon group shown has a heteroatom of N, O, or S, and has a 5-membered ring, a 6-membered ring, or a structure formed by their fusion. As Y 101 The cyclic heteroaliphatic hydrocarbon group shown preferably has N, O or S heteroatoms and has a 5-membered ring, 6-membered ring, 7-membered ring, 8-membered ring or a structure formed by their fusion.

[0120] As a provider of Y 101 The compounds shown are monocyclic, bicyclic, or fused-ring aromatic hydrocarbon groups, without particular limitation. Examples include, independently, benzene, biphenyl, terphenyl, naphthalene, fluorene, spirodifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzo[a]fluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, β-, perylene, benzo[a]pyrene, triphenylene, dibenzo[a]pyrene, or compounds formed by fused one or more of benzene, naphthalene, and phenanthrene to these compounds.

[0121] As a provider of Y 101 The compounds of monocyclic, bicyclic, or fused-ring aromatic hydrocarbon groups shown are preferably, independently: benzene, biphenyl, terphenyl, naphthalene, fluorene, spirodifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzo[a]fluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, β, perylene, benzo[a]pyrene, triphenylene, dibenzo[a]pyrene, and compounds formed by fused benzene or naphthalene to these groups.

[0122] As a provider of Y 101 The monocyclic, bicyclic, or fused-ring aromatic hydrocarbon compounds shown are each more preferably: benzene, biphenyl, terphenyl, naphthalene, fluorene, spirodifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzo[a]fluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, β, perylene, benzo[a]pyrene, triphenylene, or dibenzo[a]pyrene.

[0123] As a provider of Y 101 The monocyclic, bicyclic, or fused-ring aromatic hydrocarbon compounds shown are further preferred independently: benzene, biphenyl, terphenyl, naphthalene, fluorene, spirodifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzo[a]fluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, β-phenanthene, benzo[a]phenanthrene, and triphenylene.

[0124] As a provider of Y 101 The monocyclic, bicyclic, or fused-ring aromatic hydrocarbon compounds shown are further preferred individually: benzene, biphenyl, naphthalene, fluorene, spirodifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, phenanthrene, triphenylene, anthracene, pyrene, β-triphenylene, and triphenylene.

[0125] As a provider of Y 101 The compounds shown are monocyclic, cyclic, or fused-ring aromatic hydrocarbon groups, each of which is further preferred independently: benzene, biphenyl, naphthalene, fluorene, spirodifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, anthracene, and pyrene.

[0126] As a provider of Y 101 The compounds shown are of monocyclic, cyclic, or fused-ring aromatic hydrocarbon groups, each of which is particularly preferred independently: benzene, naphthalene, fluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, anthracene, and pyrene.

[0127] As a provider of Y 101The compounds shown are monocyclic, bicyclic, or fused-ring heteroaromatic hydrocarbon groups, without particular limitation. Examples include, independently, pyridine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thiaanthracene, acridine, dihydroacridine, phenoxazine, phenthiazine, dibenzo-1,4-dioxin, 5,6,7,8-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, or compounds formed by fused one or more of benzene, naphthalene, and phenanthrene to these compounds.

[0128] As a provider of Y 101 The compounds shown are monocyclic, bicyclic, or fused-ring heteroaromatic hydrocarbon groups, each preferably independently of: pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thiaanthracene, acridine, dihydroacridine, phenoxazine, phenthiazine, dibenzo-1,4-dioxin, 5,6,7,8-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, or compounds formed by fused benzene or naphthalene to these groups.

[0129] As a provider of Y 101 The monocyclic, bicyclic, or fused-ring heteroaromatic hydrocarbon compounds shown are each more preferably: pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thiaanthracene, acridine, dihydroacridine, phenoxazine, phenthiazine, dibenzo-1,4-dioxin, 5,6,7,8-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole.

[0130] As a provider of Y 101 The monocyclic, bicyclic, or fused-ring heteroaromatic hydrocarbon compounds shown are further preferred independently as follows: pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thiaanthracene, acridine, dihydroacrylidine, dibenzo-1,4-dioxin, 5,6,7,8-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and benzothiazole.

[0131] As a provider of Y 101The monocyclic, bicyclic, or fused-ring heteroaromatic hydrocarbon compounds shown are further preferred individually: pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, benzofuran, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, acridine, dibenzo-1,4-dioxin, 5,6,7,8-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine.

[0132] As a provider of Y 101 The monocyclic, bicyclic, or fused-ring heteroaromatic hydrocarbon compounds shown are each, more preferably, independently: pyridine, pyrimidine, pyrazine, triazine, carbazole, benzodioxin, dibenzofuran, dibenzothiophene, acridine, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine.

[0133] As a provider of Y 101 The monocyclic, cyclic, or fused-ring heteroaromatic hydrocarbon compounds shown are particularly preferred individually: pyridine, pyrimidine, triazine, carbazole, dibenzofuran, and dibenzothiophene.

[0134] As a provider of Y 101 The cyclic aliphatic hydrocarbon compounds shown are not particularly limited, and examples that can be listed independently include: adamantane, diadamantane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, etc.

[0135] As a provider of Y 101 The cyclic aliphatic hydrocarbon compounds shown are each preferably independently: adamantane, diadamantane, norbornene, and cyclohexane.

[0136] As a provider of Y 101 The cyclic aliphatic hydrocarbon compounds shown are each more preferably: adamantane, diadamantane, and cyclohexane.

[0137] As a provider of Y 101 The cyclic heteroaliphatic hydrocarbon compounds shown are not particularly limited, and can be cited independently as examples such as: morpholine, piperazine, high piperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiaane, 4,4′-bipiperidine, diazabicyclo[2,2,2]octane, and octahydro-1H-pyrrolo[3,4-b]pyridine, 1,4,7,10-tetraazacyclododecane, etc.

[0138] As a provider of Y 101The cyclic heteroaliphatic hydrocarbon compounds shown are each preferably: morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiaane, 4,4′-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane.

[0139] As a provider of Y 101 The cyclic heteroaliphatic hydrocarbon compounds shown are each more preferred independently: piperazine, high piperazine, 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.

[0140] As a provider of Y 101 The cyclic heteroaliphatic hydrocarbon compounds shown are further preferred individually: piperazine, high piperazine, 4,4′-bipiperidine, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane.

[0141] As a provider of Y 101 The cyclic heteroaliphatic hydrocarbon compounds shown are further preferred individually: piperazine, high piperazine, and 1,4,7,10-tetraazacyclododecane.

[0142] As a provider of Y 101 The cyclic heteroaliphatic hydrocarbon compounds shown are each, more preferably, piperazine or homopiperazine.

[0143] (Y 101 (Preferred mode of substituents) As the Y 101 The substituents are not particularly limited; for example, each can be listed independently: Methyl, methoxy, trifluoromethoxy, alkyl with 2-10 carbon atoms, cyano, deuterium, fluorine, chlorine, bromine, iodine, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, indoleyl, carbazoleyl, benzothiopheneyl, dibenzothiopheneyl, benzofuranyl, dibenzofuranyl, thiazolyl, benzothiazolyl, the structure shown in formula (111), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

[0144] As Y 101 The substituents are each preferred independently: Methyl, methoxy, trifluoromethyl, trifluoromethoxy, alkyl with 2 to 10 carbon atoms, fluorine atom, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, carbazoleyl, benzothiopheneyl, dibenzothiopheneyl, benzofuranyl, dibenzofuranyl, thiazolyl, benzothiazolyl, the structure shown in formula (111), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

[0145] As Y 101 Each of the substituents is more preferred independently: Methyl, methoxy, trifluoromethyl, trifluoromethoxy, alkyl with 2 to 10 carbon atoms, fluorine atom, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, thiazolyl, the structure shown in formula (111), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

[0146] As Y 101 The substituents are each further optimized independently: Methyl, trifluoromethyl, alkyl with 2 to 10 carbon atoms, fluorine atom, phenyl, biphenyl, pyridyl, pyrimidinyl, pyrazinyl, triazineyl, the structure shown in formula (111), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

[0147] As Y 101 The substituents are each further optimized independently: Methyl, trifluoromethyl, alkyl with 2 to 4 carbon atoms, fluorine atom, phenyl, pyridyl, pyrimidinyl, triazine, the structure shown in formula (111), or a structure formed by further substituting these groups with one or more groups selected from these groups.

[0148] As Y 101 The substituents are each particularly preferred independently: The structure is a methyl group, an alkyl group having 2 to 4 carbon atoms, a fluorine atom, a pyridyl group, a pyrimidinyl group, a triazine group, the structure shown in formula (111), or a structure formed by further substituting these groups with one or more groups selected from these groups.

[0149] (Y 101 specific examples) As the Y 101 For example, the structures shown below (AAB1) to (AAB561) can be cited.

[0150] It should be noted that the markings used in the following structure are " “ represents the bonding site, F represents the fluorine atom, Rs represents the structure shown in formula (555), v represents an integer from 0 to 5, w represents an integer from 0 to 4, x represents an integer from 0 to 3, y represents an integer from 0 to 2, and z represents an integer from 0 to 1.

[0151] [Chemistry 34]

[0152] [Chemistry 35]

[0153] [Chemistry 36]

[0154] [Chemistry 37]

[0155] [Chemistry 38]

[0156] [Chemistry 39]

[0157] [Chemistry 40]

[0158] [Chemistry 41]

[0159] [Chemistry 42]

[0160] [Chemistry 43]

[0161] [Chemistry 44]

[0162] [Chemistry 45]

[0163] [Chemistry 46]

[0164] [Chemistry 47]

[0165] [Chemistry 48]

[0166] [Chemistry 49]

[0167] [Transformation 50]

[0168] [Chemistry 51]

[0169] [Chemistry 52]

[0170] [Chemistry 53]

[0171] [Chemistry 54]

[0172] [Chemistry 55]

[0173] (X 101 (Preferred method) In the above formula (101), X 101 Each can independently represent a cyclic aliphatic hydrocarbon group with 3 to 8 substituted carbon atoms, a monocyclic, combined, or fused-ring heteroaliphatic hydrocarbon group with 3 to 26 substituted carbon atoms, O, OR 101 , S, SR 101 、N(R 101 ) f 101 or Si(R) 101 ) f 101 .

[0174] As X 101 The cyclic heteroaliphatic hydrocarbon group shown preferably has N, O or S heteroatoms and has a 5-membered ring, 6-membered ring, 7-membered ring, 8-membered ring or a structure formed by their fusion.

[0175] As a provider of X 101 The cyclic aliphatic hydrocarbon compounds shown are not particularly limited, and examples include: adamantane, diadamantane, norbornene, cyclopentane, cyclohexane, cycloheptane, cyclooctane, etc.

[0176] As a provider of X 101 The cyclic aliphatic hydrocarbon compounds shown are each preferably independently: adamantane, diadamantane, norbornene, cyclohexane, cycloheptane, and cyclooctane.

[0177] As a provider of X 101The cyclic aliphatic hydrocarbon compounds shown are each more preferably: adamantane, diadamantane, norbornene, and cyclohexane.

[0178] As a provider of X 101 The cyclic aliphatic hydrocarbon compounds shown are further preferred individually: adamantane, diadamantane, and cyclohexane.

[0179] As a provider of X 101 The cyclic aliphatic hydrocarbon compounds shown are further preferably adamantane or cyclohexane, each independently.

[0180] As a provider of X 101 The cyclic heteroaliphatic hydrocarbon compounds shown are not particularly limited, and can be cited independently as examples such as: morpholine, piperazine, high piperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiaane, 4,4′-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, 1,4,7,10-tetraazacyclododecane, etc.

[0181] As a provider of X 101 The cyclic heteroaliphatic hydrocarbon compounds shown are each preferably: morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiaane, 4,4′-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane.

[0182] As a provider of X 101 The cyclic heteroaliphatic hydrocarbon compounds shown are each more preferred independently: piperazine, high piperazine, 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.

[0183] As a provider of X 101 The cyclic heteroaliphatic hydrocarbon compounds shown are further preferred individually: piperazine, homopiperazine, diazabicyclo[2,2,2]octane, and octahydro-1H-pyrrolo[3,4-b]pyridine.

[0184] As a provider of X 101 The cyclic heteroaliphatic hydrocarbon compounds shown are further preferred individually: piperazine, homopiperazine, and diazabicyclo[2,2,2]octane.

[0185] (X 101 (Preferred mode of substituents) As the X 101The substituents are not particularly limited, and can be individually exemplified by: methyl, methoxy, trifluoromethyl, trifluoromethoxy, alkyl with 2 to 10 carbon atoms, cyano, deuterium, fluorine, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, carbazolyl, benzothiophene, dibenzothiophene, benzofuranyl, dibenzofuranyl, thiazolyl, benzothiazolyl, the structure shown in formula (111), or structures obtained by further substituting these groups with one or more groups selected from these groups.

[0186] As X 101 The substituents are preferably, independently, methyl, methoxy, trifluoromethyl, trifluoromethoxy, alkyl with 2 to 10 carbon atoms, fluorine atom, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, carbazolyl, benzothiophene, dibenzothiophene, benzofuranyl, dibenzofuranyl, thiazolyl, benzothiazolyl, the structure shown in formula (111), or the structure obtained by further substituting these groups with one or more groups selected from these groups.

[0187] As X 101 The substituents are each more preferably: methyl, methoxy, trifluoromethyl, trifluoromethoxy, alkyl with 2 to 10 carbon atoms, fluorine atom, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, thiazolyl, the structure shown in formula (111), or the structure obtained by further substituting these groups with one or more groups selected from these groups.

[0188] As X 101 The substituents are further preferred individually: methyl, methoxy, trifluoromethyl, alkyl with 2 to 10 carbon atoms, fluorine atom, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, thiazolyl, the structure shown in formula (111), or the structure obtained by further substituting these groups with one or more groups selected from these groups.

[0189] As X 101 The substituents are each further preferred independently: methyl, methoxy, trifluoromethyl, alkyl with 2 to 10 carbon atoms, fluorine atom, phenyl, naphthyl, pyridyl, pyrimidinyl, triazine, the structure shown in formula (111), or the structure obtained by further substituting these groups with one or more groups selected from these groups.

[0190] As X 101The substituents are each independently further preferred to be: methyl, trifluoromethyl, alkyl with 2 to 6 carbon atoms, fluorine atom, phenyl, naphthyl, pyridyl, pyrimidinyl, triazine, the structure shown in formula (111), or a structure obtained by further substituting these groups with one or more groups selected from these groups.

[0191] (R 101 (Preferred method) In equations (101) and (111), As R 101 The aromatic hydrocarbon group shown has a phenyl group, or a structure formed by connecting or fused multiple benzene rings. As R 101 The divalent heteroaromatic hydrocarbon group shown has a heteroatom of N, O, or S, and has a 5-membered ring, a 6-membered ring, or a structure formed by their fusion. As R 101 The heteroaliphatic hydrocarbon group shown is preferably N, O or S, and has a structure of 5-membered ring, 6-membered ring, 7-membered ring, 8-membered ring or fused together thereof.

[0192] As a provider of R 101 The aromatic hydrocarbon compounds shown are not particularly limited, and can be individually exemplified as: benzene, biphenyl, terphenyl, naphthalene, fluorene, spirodifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzo[a]fluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, β-, perylene, benzo[a]β, triphenylene, dibenzo[a]β, or compounds formed by fused together with one or more of benzene, naphthalene, and phenanthrene, etc.

[0193] As a provider of R 101 The aromatic hydrocarbon compounds shown are each preferably, independently, benzene, biphenyl, naphthalene, fluorene, 9,9-dimethylfluorene, 9,phenanthrene, anthracene, pyrene, benzo[a]pyrene, dibenzo[a]pyrene, or compounds formed by fused together with one or more of benzene, naphthalene and phenanthrene.

[0194] As a provider of R 101 The aromatic hydrocarbon compounds shown are more preferably, independently, those of benzene, naphthalene, anthracene, benzo[a], dibenzo[a], or compounds formed by fused benzene or naphthalene to these groups.

[0195] As a provider of R 101The compounds with heteroaromatic hydrocarbon groups shown are not particularly limited, and can be individually exemplified as follows: pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thiaanthracene, acridine, dihydroacrylidine, phenoxazine, phenthiazine, dibenzo-1,4-dioxin, 5,6,7,8-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, or compounds formed by fused together with one or more of benzene, naphthalene, and phenanthrene, etc.

[0196] As a provider of R 101 The compounds shown are heteroaromatic hydrocarbon groups, each of which is preferably pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, thiathrone, benzothiazole, or compounds formed by fusion of one or more selected from benzene, naphthalene and phenanthrene on these groups.

[0197] As a provider of R 101 The compounds shown are heteroaromatic hydrocarbon groups, each of which is more preferably: pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, or compounds formed by fusion of benzene or naphthalene with these groups.

[0198] As R 101 The aliphatic hydrocarbon groups shown are not particularly limited, and can be individually exemplified by: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptyl, octadecyl, nonadecanyl, eicosyl, carbazolyl, adamantyl, diadamantyl, cyclohexyl, or structures formed by further substituting these groups with one or more groups selected from these groups.

[0199] As R 101 The aliphatic hydrocarbon groups shown are each preferably: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, or structures formed by further substituting these groups with one or more groups selected from these groups.

[0200] As a provider of R 101 The compounds shown are not particularly limited to heteroaliphatic hydrocarbon groups, and can be listed independently as follows: morpholine, piperazine, high piperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiaane, 4,4′-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, 1,4,7,10-tetraazacyclododecane, etc.

[0201] As R101 The substituents are not particularly limited; for example, each can be listed independently: Methyl, methoxy, trifluoromethyl, trifluoromethoxy, alkyl with 2 to 10 carbon atoms, cyano, deuterium, fluorine, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, indoleyl, carbazoleyl, benzothiopheneyl, dibenzothiopheneyl, benzofuranyl, dibenzofuranyl, thiazolyl, benzothiazolyl, the structure shown in formula (111), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

[0202] As R 101 The substituents are preferably, independently: methyl, methoxy, difluoromethyl, difluoromethoxy, alkyl with 2 to 10 carbon atoms, fluorine atom, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, the structure shown in formula (111), or the structure obtained by further substituting these groups with one or more groups selected from these groups.

[0203] As R 101 The substituents are each more preferably: methyl, methoxy, difluoromethyl, difluoromethoxy, alkyl with 2 to 10 carbon atoms, fluorine atom, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, triazineyl, the structure shown in formula (111), or the structure obtained by further substituting these groups with one or more groups selected from these groups.

[0204] Additionally, R 101 They can bond together, in R 101 = In the case of methyl, through R 101 They bond together and can exhibit ethylene form.

[0205] [Second method: Compound] (Preferred method of formula (501)) The compound involved in one aspect of this disclosure is represented by the following formula (501).

[0206] [Chemistry 56]

[0207] In the aforementioned formula (501), Y 501 This refers to an aromatic hydrocarbon group with 6 to 26 substituted carbon atoms, consisting of a monocyclic, intercyclic, or fused ring; a heteroaromatic hydrocarbon group with 3 to 26 substituted carbon atoms; a cyclic aliphatic hydrocarbon group with 3 to 8 substituted carbon atoms; or a heteroaliphatic hydrocarbon group with 3 to 26 substituted carbon atoms. X 501This indicates a cyclic aliphatic hydrocarbon group with 3 to 8 substituted carbon atoms, or a heteroaliphatic hydrocarbon group with 3 to 26 substituted carbon atoms, including monocyclic, cyclic, or fused-ring groups, O, OR. 501 , S, SR 501 、N(R 501 ) f 501 or Si(R) 501 ) f 501 , R 501 Bonded to an oxygen, sulfur, or nitrogen atom, each independently representing a monocyclic, intercyclic, or fused-ring aromatic hydrocarbon group with 6 to 26 substituted carbon atoms; a heterocyclic aromatic hydrocarbon group with 3 to 26 substituted carbon atoms; a straight-chain, branched, or cyclic aliphatic hydrocarbon group with 1 to 18 substituted carbon atoms; a heterocyclic aliphatic hydrocarbon group with 3 to 26 substituted carbon atoms; a hydrogen atom; or the following formula (555). Rs 501 Each of them independently represents the group shown in the following formula (555). a 501 Each can independently represent an integer from 1 to 6. b 501 Each can independently represent an integer from 0 to 8. c 501 Each can independently represent an integer from 0 to 8. e 501 Each can independently represent an integer from 1 to 8. f 501 Each can independently represent an integer from 0 to 3.

[0208] [Chemistry 57]

[0209] In the aforementioned formula (555), L 555 Each can independently represent a straight-chain, branched, or cyclic aliphatic hydrocarbon group with 1 to 18 carbon atoms that can be substituted; a straight-chain, branched, or cyclic alkenyl group with 1 to 18 carbon atoms that can be substituted; or a straight-chain, branched, or cyclic ethynyl group with 1 to 18 carbon atoms that can be substituted. X 555 Each can be independently represented as O, S, NH, or NR. 501 , R 501Bonded to a nitrogen atom, each independently representing a monocyclic, bicyclic, or fused-ring aromatic hydrocarbon group with 6 to 26 substituted carbon atoms; a heterocyclic aromatic hydrocarbon group with 3 to 26 substituted carbon atoms; a straight-chain, branched, or cyclic aliphatic hydrocarbon group with 1 to 18 substituted carbon atoms; a heterocyclic aliphatic hydrocarbon group with 3 to 26 substituted carbon atoms; a hydrogen atom; or the formula (555) stated above. Indicates the bonding location, a 555 Each can independently represent an integer from 1 to 6. b 555 Each can independently represent an integer from 1 to 18. c 555 Each can independently represent an integer from 1 to 2. d 555 Each can independently represent an integer from 0 to 1.

[0210] The compound represented by formula (501) has two or more structures of formula (555) within the molecule, or has one or more fluorine atoms outside of formula (555) within the molecule.

[0211] (Rs 501 (Preferred method) The Rs 501 Each of the groups represented by formula (555) can be independently represented.

[0212] In formula (555), SF5 represents pentafluorosulfonyl, which is a structure with five fluorine atoms bonded to sulfur atoms, as represented by formula (222).

[0213] In the aforementioned formula (555), L 555 The molecular structure of the shown groups is not particularly limited and can be any of the following: linear, branched, or cyclic.

[0214] (L 555 (Preferred method) As the L 555 The aliphatic hydrocarbon groups shown are not particularly limited, and can be listed independently as follows: methylene, ethane, propane, butane, pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, heptane, octadecane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, or groups that have a structural isomer relationship with these groups.

[0215] As L 555The alkenyl groups shown are not particularly limited, and can be individually exemplified by: vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptenyl, octadecenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, or groups that have structural isomerism with these groups.

[0216] As L 555 The ethynyl group shown is not particularly limited, and examples that can be independently cited include: ethynyl, propynyl, butynyl, pentynyl, hexynyl, hepynyl, octyynyl, nonynyl, decyynyl, undecynyl, dodeynyl, tridecynyl, tetradecynyl, decadecynyl, hexadecynyl, heptynyl, octadecynyl, or groups that have structural isomerism with these groups.

[0217] As L 555 The aliphatic hydrocarbon groups shown are each preferably methylene, ethane, propane, butane, pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, cyclobutane, cyclopentane, cyclohexane, or groups that have a structural isomerism relationship with these groups.

[0218] As L 555 The alkenyl groups shown are each preferably, independently: vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, cyclobutenyl, cyclopentenyl, or groups that have a structural isomerism relationship with these groups.

[0219] As L 555 The acetylenic groups shown are each preferably, independently, acetylenic, propynyl, butynyl, pentynyl, hexynyl, hepynyl, octylenyl, nonynyl, decynyl, undecynyl, dodecaynyl, tridecynyl, tetradecynyl, decadecynyl, hexadecynyl, or groups that have structural isomerism with these groups.

[0220] As L 555 The aliphatic hydrocarbon groups shown are each more preferably, independently, methylene, ethyl, propane, butane, pentane, hexane, heptane, octane, nonane, decane, undecane, cyclopentane, cyclohexane, or groups that have a structural isomerism relationship with these groups.

[0221] As L 555The alkenyl groups shown are more preferably, independently, vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, cyclopentenyl, or groups that have a structural isomerism relationship with these groups.

[0222] As L 555 The acetylenic group shown is more preferably, independently, acetylenic, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octylenyl, nonynyl, decynyl, or groups that have a structural isomerism relationship with these groups.

[0223] As L 555 The aliphatic hydrocarbon groups shown are further preferred individually as follows: methylene, ethane, propane, butane, pentane, hexane, heptane, cyclopentane, cyclohexane, or groups that have a structural isomerism relationship with these groups.

[0224] As L 555 The alkenyl groups shown are further preferred individually: vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, cyclopentenyl, or groups that have a structural isomerism relationship with these groups.

[0225] As L 555 The acetylenic groups shown can be further preferred independently as follows: acetylenic, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octylenyl, or groups that have structural isomerism with these groups.

[0226] As L 555 The aliphatic hydrocarbon groups shown are further preferred individually: methylene, ethane, propane, butane, pentane, cyclohexane, or groups that have a structural isomer relationship with these groups.

[0227] As L 555 The alkenyl groups shown are further preferred individually: vinyl, propenyl, butenyl, pentenyl, cyclopentenyl, or groups that have a structural isomer relationship with these groups.

[0228] As L 555 The acetylenic group shown can be further preferred independently as follows: acetylenic, propynyl, butynyl, pentynyl, hexynyl, or groups that have structural isomerism with these groups.

[0229] As L 555 The aliphatic hydrocarbon groups shown are particularly preferred individually: methylene, ethane, propane, cyclohexane, or groups that have a structural isomer relationship with these groups.

[0230] As L 555The alkenyl groups shown are particularly preferred individually: vinyl, propenyl, cyclopentenyl, or groups that have a structural isomer relationship with these groups.

[0231] As L 555 The acetylenic groups shown are particularly preferred individually: acetylenic, propynyl, butynyl, or groups that have a structural isomer relationship with these groups.

[0232] (X 555 (Preferred method) As the X 555 The indicated groups are each preferably O, S, NH or NR, respectively. 501 .

[0233] As the X 555 The groups shown are each more preferably O, S, or NR, independently. 501 .

[0234] As the X 555 The groups shown are each further preferably selected from O and NR. 501 .

[0235] As the X 555 The groups shown are each particularly preferred to be O.

[0236] (Y 501 (Preferred method) In the aforementioned formula (501), Y 501 Each can independently represent a monocyclic, bicyclic, or fused-ring aromatic hydrocarbon group with 6 to 26 substituted carbon atoms; a heterocyclic aromatic hydrocarbon group with 3 to 26 substituted carbon atoms; a cyclic aliphatic hydrocarbon group with 3 to 8 substituted carbon atoms; or a heterocyclic aliphatic hydrocarbon group with 3 to 26 substituted carbon atoms.

[0237] As Y 501 The aromatic hydrocarbon group shown has a phenyl group, or a structure formed by connecting or fused multiple benzene rings. As Y 501 The heteroaromatic hydrocarbon group shown has a heteroatom of N, O, or S, and has a 5-membered ring, a 6-membered ring, or a structure formed by their fusion. As Y 501 The heteroaliphatic hydrocarbon group shown is preferably N, O or S, and has a 5-membered ring, 6-membered ring, 7-membered ring or a structure formed by their fusion.

[0238] As a provider of Y 501The compounds shown are of monocyclic, bicyclic, cyclic, or fused-ring aromatic hydrocarbon groups, without particular limitation. Examples include, independently, benzene, biphenyl, terphenyl, naphthalene, fluorene, spirodifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzo[a]fluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, β-, perylene, benzo[a]β, triphenylene, dibenzo[a]β, or compounds formed by fused to these compounds with one or more of benzene, naphthalene, and phenanthrene.

[0239] As a provider of Y 501 The compounds shown are monocyclic, bicyclic, or fused-ring aromatic hydrocarbon groups, each preferably independently: benzene, biphenyl, terphenyl, naphthalene, fluorene, spirodifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzo[a]fluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, β-, perylene, benzo[a]β, triphenylene, dibenzo[a]β, or compounds formed by fused benzene or naphthalene to these compounds.

[0240] As a provider of Y 501 The compounds shown are monocyclic, bicyclic, or fused-ring aromatic hydrocarbon groups, each of which is more preferably: benzene, biphenyl, terphenyl, naphthalene, fluorene, spirodifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzo[a]fluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, β, perylene, benzo[a]pyrene, triphenylene, dibenzo[a]pyrene.

[0241] As a provider of Y 501 The monocyclic, bicyclic, or fused-ring aromatic hydrocarbon compounds shown are further preferred independently: benzene, biphenyl, terphenyl, naphthalene, fluorene, spirodifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzo[a]fluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, β-phenanthene, benzo[a]phenanthrene, and triphenylene.

[0242] As a provider of Y 501 The compounds shown are monocyclic, bicyclic, or fused-ring aromatic hydrocarbon groups, each of which is further preferred independently: benzene, biphenyl, terphenyl, naphthalene, fluorene, spirodifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzo[a]fluorene, phenanthrene, fluoranthene, anthracene, pyrene, and β-fluorene.

[0243] As a provider of Y 501 The compounds shown are monocyclic, bicyclic, or fused-ring aromatic hydrocarbon groups, each of which is further preferred independently: benzene, biphenyl, naphthalene, fluorene, spirodifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzo[a]fluorene, phenanthrene, and anthracene.

[0244] As a provider of Y 501 The compounds shown are monocyclic, cyclic, or fused-ring aromatic hydrocarbon groups, each of which is particularly preferred independently: benzene, biphenyl, naphthalene, spirofluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, and anthracene.

[0245] As a provider of Y 501The compounds shown are monocyclic, bicyclic, cyclic, or fused-ring heteroaromatic hydrocarbon groups, without particular limitation. Examples of such compounds include, independently, pyridine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thiaanthracene, acridine, dihydroacridine, phenoxazine, phenthiazine, dibenzo-1,4-dioxin, 5,6,7,8-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, or compounds formed by fused one or more of benzene, naphthalene, and phenanthrene to these compounds.

[0246] As a provider of Y 501 The compounds shown are monocyclic, bicyclic, or fused-ring heteroaromatic hydrocarbon groups, each preferably independently of: pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thiaanthracene, acridine, dihydroacridine, phenoxazine, phenthiazine, dibenzo-1,4-dioxin, 5,6,7,8-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, or compounds formed by fused benzene or naphthalene to these groups.

[0247] As a provider of Y 501 The monocyclic, bicyclic, or fused-ring heteroaromatic hydrocarbon compounds shown are each more preferably: pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thiaanthracene, acridine, dihydroacridine, phenoxazine, phenthiazine, dibenzo-1,4-dioxin, 5,6,7,8-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole.

[0248] As a provider of Y 501 The monocyclic, bicyclic, or fused-ring heteroaromatic hydrocarbon compounds shown are further preferred independently as follows: pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thiaanthracene, acridine, dihydroacrylidine, dibenzo-1,4-dioxin, 5,6,7,8-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and benzothiazole.

[0249] As a provider of Y 501The monocyclic, bicyclic, or fused-ring heteroaromatic hydrocarbon compounds shown are further preferred individually: pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazoline, acridine, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, and benzothiazole.

[0250] As a provider of Y 501 The monocyclic, bicyclic, or fused-ring heteroaromatic hydrocarbon compounds shown are each, independently, further preferred, pyridine, pyrazine, triazine, carbazole, furan, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazoline, acridine, and benzothiazole.

[0251] As a provider of Y 501 The monocyclic, cyclic, or fused-ring heteroaromatic hydrocarbon compounds shown are particularly preferred individually: pyridine, pyrimidine, pyrazine, triazine, carbazole, dibenzofuran, dibenzothiophene, and acridine.

[0252] As a provider of Y 501 The cyclic aliphatic hydrocarbon compounds shown are not particularly limited, and examples that can be cited independently include: adamantane, diadamantane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, etc.

[0253] As a provider of Y 501 The cyclic aliphatic hydrocarbon compounds shown are each preferably independently: adamantane, diadamantane, norbornene, and cyclohexane.

[0254] As a provider of Y 501 The cyclic aliphatic hydrocarbon compounds shown are each more preferred individually: Adamantane, diadamantane, and cyclohexane.

[0255] As a provider of Y 501 The cyclic heteroaliphatic hydrocarbon compounds shown are not particularly limited, and can be cited independently as examples such as: morpholine, piperazine, high piperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiaane, 4,4′-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, 1,4,7,10-tetraazacyclododecane, etc.

[0256] As a provider of Y 501The cyclic heteroaliphatic hydrocarbon compounds shown are each preferably: morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiaane, 4,4′-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane.

[0257] As a provider of Y 501 The cyclic heteroaliphatic hydrocarbon compounds shown are each more preferred independently: piperazine, high piperazine, 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.

[0258] As a provider of Y 501 The cyclic heteroaliphatic hydrocarbon compounds shown are further preferred independently from piperazine, homopiperazine, and 4,4′-bipiperidine.

[0259] As Y 501 The substituents are not particularly limited; for example, each can be listed independently: Methyl, methoxy, trifluoromethoxy, alkyl with 2-10 carbon atoms, cyano, deuterium, fluorine, chlorine, bromine, iodine, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazineyl, indoleyl, carbazoleyl, benzothiopheneyl, dibenzothiopheneyl, benzofuranyl, dibenzofuranyl, thiazolyl, benzothiazolyl, the structure shown in formula (555), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

[0260] As Y 501 The substituents are each preferred independently: Methyl, methoxy, trifluoromethyl, trifluoromethoxy, alkyl with 2 to 10 carbon atoms, fluorine atom, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, carbazoleyl, benzothiopheneyl, dibenzothiopheneyl, benzofuranyl, dibenzofuranyl, thiazolyl, benzothiazolyl, the structure shown in formula (555), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

[0261] As Y 501 Each of the substituents is more preferred independently: Methyl, methoxy, trifluoromethyl, trifluoromethoxy, alkyl with 2 to 10 carbon atoms, fluorine atom, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, thiazolyl, the structure shown in formula (555), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

[0262] As Y 501 The substituents are each further optimized independently: Methyl, methoxy, trifluoromethyl, alkyl with 2 to 6 carbon atoms, fluorine atom, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, the structure shown in formula (555), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

[0263] As Y 501 The substituents are each further optimized independently: Methyl, alkyl with 2 to 6 carbon atoms, fluorine atom, phenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, triazineyl, the structure shown in formula (555), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

[0264] As Y 501 Each of the substituents is further preferred independently: Methyl, alkyl with 2 to 4 carbon atoms, fluorine atom, phenyl, pyridyl, pyrimidinyl, triazine, structure represented by formula (555), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

[0265] As Y 501 The substituents are each particularly preferred independently: methyl, fluorine atom, phenyl, pyridyl, pyrimidinyl, triazine, the structure shown in formula (555), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

[0266] (Y 501 specific examples) As the Y 501 For example, the structures shown in (AAB1) to (AAB561) can be cited.

[0267] It should be noted that the markings used in the structure are " “ represents the bonding site, F represents the fluorine atom, Rs represents the structure shown in formula (555), v represents an integer from 0 to 5, w represents an integer from 0 to 4, x represents an integer from 0 to 3, y represents an integer from 0 to 2, and z represents an integer from 0 to 1.

[0268] (X 501(Preferred method) In the aforementioned formula (501), X 501 This indicates cyclic aliphatic hydrocarbon groups with 1 to 8 substituted carbon atoms, monocyclic, combined, or fused heteroaliphatic hydrocarbon groups with 3 to 26 substituted carbon atoms, and O, OR. 501 , S, SR 501 、N(R 501 ) f 501 or Si(R) 501 ) f 501 .

[0269] As X 501 The cyclic heteroaliphatic hydrocarbon group shown preferably has N, O or S heteroatoms and has a 5-membered ring, 6-membered ring, 7-membered ring, 8-membered ring or a structure formed by their fusion.

[0270] As a provider of X 501 The cyclic aliphatic hydrocarbon compounds shown are not particularly limited, and examples that can be listed independently include: adamantane, diadamantane, norbornene, cyclopentane, cyclohexane, cycloheptane, cyclooctane, etc.

[0271] As a provider of X 501 The cyclic aliphatic hydrocarbon compounds shown are each preferably independently: adamantane, diadamantane, norbornene, cyclohexane, cycloheptane, and cyclooctane.

[0272] As a provider of X 501 The cyclic aliphatic hydrocarbon compounds shown are each more preferably: adamantane, diadamantane, norbornene, and cyclohexane.

[0273] As a provider of X 501 The cyclic aliphatic hydrocarbon compounds shown are further preferred individually: adamantane, diadamantane, and cyclohexane.

[0274] As a provider of X 501 The cyclic heteroaliphatic hydrocarbon compounds shown are not particularly limited, and can be cited independently as examples such as: morpholine, piperazine, high piperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiaane, 4,4′-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, 1,4,7,10-tetraazacyclododecane, etc.

[0275] As a provider of X 501The cyclic heteroaliphatic hydrocarbon compounds shown are each preferably: morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiaane, 4,4′-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, and 1,4,7,10-tetraazacyclododecane.

[0276] As a provider of X 501 The cyclic heteroaliphatic hydrocarbon compounds shown are each more preferred 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, and 1,4,7,10-tetraazacyclododecane.

[0277] As a provider of X 501 The cyclic heteroaliphatic hydrocarbon compounds shown are further preferred individually: piperazine, high piperazine, 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.

[0278] As a provider of X 501 The cyclic heteroaliphatic hydrocarbon compounds shown are further preferred individually: piperazine, homopiperazine, hexahydro-1,3,5-triazine, and 4,4′-bipiperidine.

[0279] As X 501 The substituents can be independently categorized as follows: methyl, methoxy, trifluoromethyl, trifluoromethoxy, alkyl with 2 to 10 carbon atoms, cyano, deuterium, fluorine, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, carbazolyl, benzothiophene, dibenzothiophene, benzofuranyl, dibenzofuranyl, thiazolyl, benzothiazolyl, the structure shown in formula (555), or the structure obtained by further substituting these groups with one or more groups selected from these groups.

[0280] As X 501 The substituents are preferably, independently, methyl, methoxy, trifluoromethyl, trifluoromethoxy, alkyl with 2 to 10 carbon atoms, fluorine atom, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, carbazolyl, benzothiophene, dibenzothiophene, benzofuranyl, dibenzofuranyl, thiazolyl, benzothiazolyl, the structure shown in formula (555), or the structure obtained by further substituting these groups with one or more groups selected from these groups.

[0281] As X 501 The substituents, each independently preferred, are: methyl, methoxy, trifluoromethyl, trifluoromethoxy, alkyl with 2 to 10 carbon atoms, fluorine atom, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, thiazolyl, the structure shown in formula (555), or the structure obtained by further substituting these groups with one or more groups selected from these groups.

[0282] As X 501 The substituents are further preferred independently as follows: methyl, methoxy, alkyl with 2 to 10 carbon atoms, fluorine, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, triazineyl, the structure shown in formula (555), or the structure obtained by further substituting these groups with one or more groups selected from these groups.

[0283] As X 501 The substituents are further preferred individually: methyl, alkyl with 2 to 6 carbon atoms, fluorine atom, phenyl, biphenyl, naphthyl, pyridyl, pyrimidinyl, triazine, the structure shown in formula (555), or the structure obtained by further substituting these groups with one or more groups selected from these groups.

[0284] As X 501 The substituents are each independently and more preferably: methyl, alkyl with 2 to 4 carbon atoms, fluorine atom, phenyl, pyridyl, pyrimidinyl, triazine, the structure shown in formula (555), or a structure obtained by further substituting these groups with one or more groups selected from these groups.

[0285] (R 501 (Preferred method) In equations (501) and (555), As R 501 The aromatic hydrocarbon groups shown are monocyclic, combined, or fused rings, preferably having a phenyl group or a structure formed by connecting or fused multiple benzene rings. As R 501 The heteroaromatic hydrocarbon groups shown are monocyclic, cyclic, or fused rings, preferably with heteroatoms of N, O, or S, and have a 5-membered ring, a 6-membered ring, or a structure formed by their fusion. As R 501 The cyclic heteroaliphatic hydrocarbon group shown preferably has N, O or S heteroatoms and has a 5-membered ring, 6-membered ring, 7-membered ring, 8-membered ring or a structure formed by their fusion.

[0286] As a provider of R 501The aromatic hydrocarbon compounds shown are not particularly limited, and can be individually exemplified as: benzene, biphenyl, terphenyl, naphthalene, fluorene, spirodifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzo[a]fluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, β-, perylene, benzo[a]β, triphenylene, dibenzo[a]β, or compounds formed by fused together with one or more of benzene, naphthalene, and phenanthrene, etc.

[0287] As a provider of R 501 The aromatic hydrocarbon compounds shown are each preferably, independently, benzene, biphenyl, naphthalene, fluorene, 9,9-dimethylfluorene, 9,phenanthrene, anthracene, pyrene, benzo[a]pyrene, dibenzo[a]pyrene, or compounds formed by fused to these groups with one or more selected from benzene, naphthalene and phenanthrene.

[0288] As a provider of R 501 The aromatic hydrocarbon compounds shown are further preferred independently: benzene, naphthalene, anthracene, benzo[a], dibenzo[a], or compounds formed by fused benzene or naphthalene to these groups.

[0289] As a provider of R 501 The compounds shown are heteroaromatic hydrocarbons and are not particularly limited. Examples of such compounds include, independently, pyridine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thiaanthracene, acridine, dihydroacridine, phenoxazine, phenthiazine, dibenzo-1,4-dioxin, 5,6,7,8-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, or compounds formed by fused together with one or more of benzene, naphthalene, and phenanthrene.

[0290] As a provider of R 501 The compounds shown are heteroaromatic hydrocarbon groups, each of which is preferably: pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, thiathrone, benzothiazole, or compounds formed by fusion of one or more selected from benzene, naphthalene and phenanthrene on these groups.

[0291] As a provider of R 501 The compounds shown are heteroaromatic hydrocarbon groups, each independently and more preferably: pyridine, pyrimidine, pyrazine, triazine, carbazole, furan, thiophene, or compounds formed by fusion of benzene or naphthalene on these groups.

[0292] As R 501The aliphatic hydrocarbon groups shown are not particularly limited, and examples that can be independently exemplified include: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptyl, octadecyl, nonadecanyl, carbazolyl, adamantyl, diadamantyl, cyclohexyl, or structures formed by further substituting these groups with one or more groups selected from these groups.

[0293] As R 501 The aliphatic hydrocarbon groups shown are each preferably methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, diadamantyl, or structures formed by further substituting these groups with one or more groups selected from these groups.

[0294] As a provider of R 501 The aliphatic hydrocarbon compounds shown are more preferably, independently, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantane, or structures formed by further substituting these groups with one or more groups selected from these groups.

[0295] As a provider of R 501 The aliphatic hydrocarbon compounds shown are further preferred individually: methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, cyclopentyl, cyclohexyl, adamantane, or structures obtained by further substituting these groups with one or more groups selected from these groups.

[0296] As a provider of R 501 The aliphatic hydrocarbon compounds shown are further preferred individually: methyl, ethyl, propyl, butyl, pentyl, cyclohexyl, adamantane, or structures formed by further substituting these groups with one or more groups selected from these groups.

[0297] As R 501 The substituents are not particularly limited, and can be individually exemplified by: methyl, methoxy, trifluoromethyl, trifluoromethoxy, alkyl with 2 to 10 carbon atoms, cyano, deuterium, fluorine, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, carbazolyl, benzothiophene, dibenzothiophene, benzofuranyl, dibenzofuranyl, thiazolyl, benzothiazolyl, the structure shown in formula (555), or structures obtained by further substituting these groups with one or more groups selected from these groups.

[0298] As R 501The substituents are preferably, independently: methyl, methoxy, difluoromethyl, difluoromethoxy, alkyl with 2 to 10 carbon atoms, fluorine atom, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazineyl, the structure shown in formula (555), or the structure obtained by further substituting these groups with one or more groups selected from these groups.

[0299] As R 501 The substituents are each more preferably: methyl, methoxy, difluoromethyl, difluoromethoxy, alkyl with 2 to 10 carbon atoms, fluorine atom, naphthyl, pyridyl, pyrimidinyl, pyrazinyl, triazineyl, the structure shown in the formula (555), or the structure obtained by further substituting these groups with one or more groups selected from these groups.

[0300] (X 501 With R 501 R at that time 501 (structure) As the X 501 With R 501 R at that time 501 The structure is not particularly restricted; for example, if R is... 501 If the bonded group is set to D, the following bonding methods can be cited.

[0301] [Chem.58]

[0302] In one aspect of the invention, the compound represented by formula (501) preferably has two or more structures of formula (555) within the molecule, more preferably three or more, and even more preferably four or more.

[0303] (Concrete example of formula (555)) As an example of the aforementioned formula (555), the structures shown in (AAA1) to (AAA198) above can be cited.

[0304] (Preferred methods of equations (511), (531), and (541)) Examples of compounds represented by formula (501) include those represented by formulas (511), (531) or (541).

[0305] [Chemistry 59]

[0306] In the formula, Y 501 X 501 Rs 501 a 501 b 501 c 501 d501 e 501 It is synonymous with the definition recorded in equation (501).

[0307] (equation (531) n) 501 (Preferred method) n in equation (531) 501 Preferably, it is an integer from 1 to 12, more preferably an integer from 1 to 10, even more preferably an integer from 1 to 8, and particularly preferably an integer from 1 to 6.

[0308] (Preferred method of equation (512)) In addition to the compounds described above, other compounds, such as those shown in formula (512), may be cited as examples of compounds represented by the formula (501).

[0309] [Transformation 60]

[0310] In the above equation (512), Rs 501 a 501 b 501 c 501 d 501 e 501 Synonymous with the definition stated in equation (501), m 501 Each of the integers from 1 to 6 can be represented independently, Y 501 Let A′ represent any one of the following equations (4-1) to (4-8). This represents a bonding bond.

[0311] [Chemistry 61]

[0312] In equations (4-1) to (4-8) above, R 401 ~R 410 Each is independently represented by a hydrogen atom; a deuterium atom; a fluorine atom; a bromine atom; a chlorine atom; a straight-chain, branched, or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms that can be replaced by a fluorine atom; a straight-chain, branched, or cyclic alkoxy group having 1 to 20 carbon atoms that can be replaced by a fluorine atom; a cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms that can be replaced by a monocyclic, bicyclic, or fused ring; an aromatic hydrocarbon group having 6 to 25 carbon atoms that can be replaced by a monocyclic, bicyclic, or fused ring; or a heteroaromatic group having 3 to 25 carbon atoms that can be replaced by a monocyclic, bicyclic, or fused ring; or the formula (555).

[0313] (Preferred method of equation (532)) In addition to the compounds described above, other compounds, such as those shown in formula (532), may be cited as examples of compounds represented by the formula (501).

[0314] [Chemistry 62]

[0315] In the aforementioned formula (532), Y 501 X 501 Rs 501 R 501 a 501 b 501 c 501 e 501 , f 501 It is synonymous with the definition recorded in equation (501).

[0316] In the above formula (532), A′ and m 501 It is synonymous with the definition recorded in equation (511).

[0317] (Preferred methods of equations (533), (534), (535) and (536)) In addition to the compounds described above, other compounds represented by formula (501) may include, for example, compounds represented by formulas (533), (534), (535) or (536).

[0318] [Chemistry 63]

[0319] Y in equations (533), (534), (535) or (536) 501 Rs 501 R 501 a 501 b 501 e 501 It is synonymous with the definition recorded in equation (501).

[0320] In equations (533), (534), (535), or (536), A′, m 501 It is synonymous with the definition recorded in equation (511).

[0321] (Preferred method of equation (542)) In addition to the compounds described above, compounds represented by the following formula (542) can be cited as compounds represented by the formula (501).

[0322] [Chemistry 64]

[0323] In the aforementioned equation (542), Rs 501 R 501 a501 e 501 f 501 It is synonymous with the definition recorded in equation (501).

[0324] In the above equation (542), n 501 It is synonymous with the definition recorded in equation (511).

[0325] In the above formula (542), A′ and m 501 It is synonymous with the definition recorded in equation (511).

[0326] In the aforementioned formula (542), C′ is composed of O, NH, N(R) 501 )f 501 , S, Si(R 501 )f 501 express.

[0327] The alkyl moiety in the formula is represented by R, which is a chain-like aliphatic hydrocarbon. 501 It is represented by bonding.

[0328] For example, in R 501 When both components are methyl, it forms an ethylene; when both components are ethyl, it forms a butylene. Additionally, when both are methyl and ethyl, it can represent a propylene group.

[0329] [Chemistry 65]

[0330] The compound represented by formula (501) is particularly preferred as the compound represented by formula (543).

[0331] [Chemistry 66]

[0332] In the aforementioned equation (543), Rs 501 a 501 e 501 Synonymous with the definition recorded in equation (501), n 501 Synonymous with the definitions recorded in equation (511), A′, m 501 It is synonymous with the definition recorded in equation (511).

[0333] (Preferred method for A′) Each of A′ independently represents any one of the following equations (4-1) to (4-8). This represents a bonding bond.

[0334] [Chemistry 67]

[0335] In equations (4-1) to (4-8), R 401 ~R 410 Each is independently represented by a hydrogen atom; a deuterium atom; a fluorine atom; a bromine atom; a chlorine atom; a straight-chain, branched, or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms that can be replaced by a fluorine atom; a straight-chain, branched, or cyclic alkoxy group having 1 to 20 carbon atoms that can be replaced by a fluorine atom; a cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms that can be replaced by a monocyclic, bicyclic, or fused ring; an aromatic hydrocarbon group having 6 to 25 carbon atoms that can be replaced by a monocyclic, bicyclic, or fused ring; or a heteroaromatic group having 3 to 25 carbon atoms that can be replaced by a monocyclic, bicyclic, or fused ring; or the formula (555).

[0336] In formula (512), from the perspective of suppressing the formation of metal films on the film surface and achieving excellent adhesion with organic films, A′ is preferably any one of the following formulas (6-1) to (6-36). It should be noted that... This represents a bonding bond.

[0337] [Chemistry 68]

[0338] [Chemistry 69]

[0339] [Chemistry 70]

[0340] [Chemistry 71]

[0341] (R 501 ~R 586 (Preferred method) In equations (6-1) to (6-36), R 501 ~R 586 Each can be represented independently as: hydrogen atom, deuterium atom, fluorine atom, bromine atom, chlorine atom, a straight-chain or branched aliphatic hydrocarbon group with 1 to 4 carbon atoms, a straight-chain or branched alkoxy group with 1 to 4 carbon atoms that can be replaced by a fluorine atom, a cyclic aliphatic hydrocarbon group with 5 to 20 carbon atoms that can be replaced, a cyclic heteroaliphatic hydrocarbon group with 3 to 20 carbon atoms that can be replaced, an aromatic hydrocarbon group with 6 to 20 carbon atoms that can be replaced, or a heteroaromatic group with 3 to 20 carbon atoms that can be replaced.

[0342] As the R 501 ~R 586 Each of these atoms is preferably a hydrogen atom, a fluorine atom, a chlorine atom, a methyl group, a trifluoromethyl group, a methoxy group, a phenyl group, or a naphthyl group.

[0343] The R 501 ~R 586 Each of these atoms is more preferably a hydrogen atom, a fluorine atom, a chlorine atom, a methyl atom, a methoxy atom, or a phenyl atom.

[0344] The R 501 ~R 586 Each atom is further preferably hydrogen, fluorine, chlorine, or methyl.

[0345] The R 501 ~R 586 Each of these can be further preferred independently, consisting of hydrogen atoms, fluorine atoms, or methyl groups.

[0346] (L 601 ~L 660 (Preferred method) In equations (6-1) to (6-36), L 601 ~L 660 Each of these elements independently represents a straight-chain or branched divalent aliphatic hydrocarbon group, oxygen atom, sulfur atom, or single bond with 1 to 4 carbon atoms.

[0347] The L 601 ~L 660 Each atom is preferably an oxygen atom or a single bond.

[0348] (L 701 ~L 760 (Preferred method) In equations (6-1) to (6-36), L 701 ~L 760 Each of these elements independently represents a straight-chain or branched divalent aliphatic hydrocarbon group, oxygen atom, sulfur atom, or single bond with 1 to 4 carbon atoms.

[0349] L 701 ~L 760 Each component is preferably methylene, ethylene, propylene, butylene, or a single bond.

[0350] (Optimal selection of p and q) In equations (6-1) to (6-36), p and q each independently represent integers from 0 to 11. Preferably, p and q are integers from 0 to 9.

[0351] (Specific examples of patterned metallic materials) As one aspect of this disclosure, the metal patterning material may include, for example, a material comprising any of the compounds shown in formulas (Z1) to (Z381) below, but this disclosure is not limited to these compounds.

[0352] [Chemistry 72]

[0353] [Chemistry 73]

[0354] [Chemistry 74]

[0355] [Chemistry 75]

[0356] [Chemistry 76]

[0357] [Chemistry 77]

[0358] [Chemistry 78]

[0359] [Chemistry 79]

[0360] [Chemistry 80]

[0361] [Chemistry 81]

[0362] [Chemistry 82]

[0363] [Chemistry 83]

[0364] [Chemistry 84]

[0365] [Chemistry 85]

[0366] [Chemistry 86]

[0367] [Chemistry 87]

[0368] [Chemistry 88]

[0369] [Chemistry 89]

[0370] [Chemistry 90]

[0371] [Chemistry 91]

[0372] [Chemistry 92]

[0373] [Chemistry 93]

[0374] [Chemistry 94]

[0375] [Chem. 95]

[0376] [Thin Film for Metal Patterning] One aspect of this disclosure relates to a metal patterning film comprising the aforementioned metal patterning material or a metal patterning material containing the aforementioned compound, capable of patterning metal films or metal laminates.

[0377] In the metal patterning film, the metal patterning material preferably includes the compound shown in formula (101).

[0378] The metal film or metal laminate preferably contains one or more metals selected from lithium, ytterbium, magnesium, silver, and aluminum, or contains an alloy containing one or more of these metals. Magnesium alloys or silver alloys are preferred as alloys included in the metal film or metal laminate.

[0379] The water contact angle of the metal patterning film is more preferably 90° or higher, 91° or higher, 92° or higher, 93° or higher, 94° or higher, 95° or higher, 96° or higher, 97° or higher, 98° or higher, 99° or higher, and 100° or higher.

[0380] [Organic electroluminescent element] One aspect of this disclosure relates to an organic electroluminescent element having a cathode. The cathode contains at least one element selected from ytterbium, magnesium, silver, lithium, aluminum, and alloys of magnesium and silver. The cathode has been patterned with the metal patterning material or a metal patterning material containing the compound.

[0381] In the organic electroluminescent element, the metal patterning material used for patterning preferably contains the compound shown in the above formula (101).

[0382] (Preferred method for organic electroluminescent elements) There is no particular limitation on the configuration of the organic electroluminescent device, but examples of configurations shown below (i) to (v) are given.

[0383] (i) Anode / Light-emitting layer / Patterned layer / Metal electrode (ii) Anode / hole transport layer / light-emitting layer / patterning layer / metal electrode (iii) Anode / Light-emitting layer / Electron transport layer / Patterning layer / Metal electrode (iv) Anode / hole transport layer / light-emitting layer / electron transport layer / patterning layer / metal electrode (v) Anode / Hole Injection Layer / Hole Transport Layer / Light Emitting Layer / Electron Transport Layer / Patterned Layer / Metal Electron Figure 5 This is a schematic cross-sectional view illustrating an example of a stacked configuration of an organic electroluminescent element according to one aspect of this disclosure.

[0384] It should be explained that Figure 5 The organic electroluminescent element shown has a so-called top-emission type element configuration, but the organic electroluminescent element involved in one aspect of the present invention is not limited to a top-emission type element configuration. That is, the organic electroluminescent element involved in one aspect of the present disclosure can be other known element configurations such as bottom-emission type.

[0385] exist Figure 5 In this embodiment, the organic electroluminescent element 100 sequentially comprises a substrate 1, an anode 2, a hole injection layer 3, a hole transport layer 4, a light-emitting layer 5, an electron transport layer 6, a cathode patterning layer 50, and a protective layer 9. However, some layers except the cathode patterning layer 50 can be omitted; conversely, other layers can be added. For example, a hole blocking layer can be provided between the light-emitting layer 5 and the electron transport layer 6; the hole injection layer 3 can be omitted, and the hole transport layer 4 can be directly provided on the anode 2. Similarly, the electron transport layer 6 can be omitted, and the cathode patterning layer 50 can be directly provided on the light-emitting layer 5. Furthermore, for example, a single-layer hole transport layer 4 and a single-layer electron transport layer 6 can each comprise multiple layers.

[0386] (Preferred embodiment of substrate 1) The substrate 1 is not particularly limited, and examples include glass plates, quartz plates, plastic plates, and plastic films. Among these, glass plates, quartz plates, and light-transmitting plastic films are preferred.

[0387] Examples of such transparent plastic films include those comprising polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyethersulfone (PES), polyetherimide, polyetheretherketone, polyphenylene sulfide, polyarylate, polyimide, polycarbonate (PC), cellulose triacetate (TAC), cellulose acetate propionate (CAP), etc.

[0388] It should be noted that, in order to enable the extraction of light emission from the substrate 1 side, the substrate 1 is transparent to the wavelength of light.

[0389] (Preferred method for anode 2) An anode 2 is disposed on the substrate 1 (on the side of the hole injection layer 3).

[0390] Materials that can be used as the anode include metals, alloys, conductive compounds, and mixtures thereof with a high work function (e.g., above 4 eV). Specific examples of anode materials include metals such as Au; conductive and transparent materials such as CuI, indium tin oxide (ITO), SnO2, and ZnO.

[0391] In the case of an organic electroluminescent element that can extract light through the anode, the anode is formed of a conductive transparent material that allows the light to pass through or substantially pass through.

[0392] (Preferred method for hole injection layer 3 and hole transport layer 4) Between the anode 2 and the light-emitting layer 5 (described later), a hole injection layer 3 and a hole transport layer 4 are sequentially disposed from the anode 2 side.

[0393] The hole injection layer and hole transport layer have the function of transferring holes injected from the anode to the light-emitting layer. By placing the hole injection layer and hole transport layer between the anode and the light-emitting layer, more holes can be injected into the light-emitting layer with a lower electric field.

[0394] Furthermore, the hole injection layer and hole transport layer also function as electron barrier layers. That is, by creating an electron barrier at the interface between the light-emitting layer and the hole injection layer and / or hole transport layer, leakage of electrons injected from the cathode and transported from the electron injection layer and / or electron transport layer to the light-emitting layer into the hole injection layer and / or hole transport layer can be suppressed. As a result, these electrons accumulate at the interface within the light-emitting layer, leading to improved luminous efficiency and other effects, thus enabling the production of organic electroluminescent devices with excellent luminous performance.

[0395] The materials used as the hole injection layer and hole transport layer possess at least one of the properties of hole injection, hole transport, and electron barrier. The materials used as the hole injection layer and hole transport layer can be any of organic or inorganic materials.

[0396] Examples of materials used as the hole injection layer and hole transport layer include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyaryl alkane derivatives, pyrazoline derivatives, pyrazolineone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrene-anthracene derivatives, fluorenone derivatives, hydrazone derivatives, styrene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers (especially thiophene oligomers), porphyrin compounds, aromatic tertiary amine compounds, and styrene amine compounds. Among these, porphyrin compounds, aromatic tertiary amine compounds, and styrene amine compounds are preferred from the perspective of good performance of organic electroluminescent elements, with aromatic tertiary amine compounds being particularly preferred.

[0397] Specific examples of the aromatic tertiary amine compounds and styrene amine compounds include: N,N,N′,N′-tetraphenyl-4,4′-diaminophenyl, N,N′-diphenyl-N,N′-bis(m-tolyl)-[1,1′-biphenyl]-4,4′-diamine (TPD), 2,2-bis(4-di-p-tolylaminophenyl)propane, 1,1-bis(4-di-p-tolylaminophenyl)cyclohexane, N,N,N′,N′-tetra-p-tolyl-4,4′-diaminobiphenyl, 1,1-bis(4-di-p-tolylaminophenyl)-4-phenylcyclohexane, bis(4-dimethylamino-2-methylphenyl)phenylmethane, bis(4-di-p-tolylaminophenyl)phenylmethane, N,N′-diphenyl Examples of biphenyls include N,N′-di(4-methoxyphenyl)-4,4′-diaminobiphenyl, N,N,N′,N′-tetraphenyl-4,4′-diaminodiphenyl ether, 4,4′-bis(diphenylamino)tetraphenyl, N,N,N-tris(p-tolyl)amine, 4-(dip-tolylamino)-4′-[4-(dip-tolylamino)styryl] zirconia, 4-N,N-diphenylamino-(2-diphenylvinyl)benzene, 3-methoxy-4′-N,N-diphenylaminozirconia, N-phenylcarbazole, 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPD), and 4,4′,4′′-tris[N-(m-tolyl)-N-phenylamino]triphenylamine (MTDATA), etc.

[0398] In addition, inorganic compounds such as p-type-Si and p-type-SiC can also be cited as examples of materials for hole injection layers and hole transport layers.

[0399] The hole injection layer and hole transport layer can be a single structure containing one or more materials, or a multi-layered structure containing the same or different compositions.

[0400] (Preferred configuration of light-emitting layer 5) A light-emitting layer 5 is disposed between the hole transport layer 4 and the electron transport layer 6, which will be described later.

[0401] Examples of materials that can be used for the luminescent layer include phosphorescent materials, fluorescent materials, and thermally activated delayed fluorescence materials. In the luminescent layer, electron-hole pairs recombine, resulting in luminescence.

[0402] The luminescent layer may comprise a single low-molecular-weight material or a single polymeric material, or more conventionally, a host material doped with guest compounds. Emission is primarily generated by the dopant and can produce any color.

[0403] Examples of the main materials include compounds having the following properties: biphenyl, fluorenyl, triphenylsilyl, carbazole, pyrene, and anthracene. More specifically, examples include: DPVBi (4,4′-bis(2,2-diphenylvinyl)-1,1′-biphenyl), BCzVBi (4,4′-bis(9-ethyl-3-carbazolevinyl)1,1′-biphenyl), TBADN (2-tert-butyl-9,10-bis(2-naphthyl)anthracene), ADN (9,10-bis(2-naphthyl)anthracene), CBP (4,4′-bis(carbazole-9-yl)biphenyl), CDBP (4,4′-bis(carbazole-9-yl)-2,2′-dimethylbiphenyl), 2-(9-phenylcarbazole-3-yl)-9-[4-(4-phenylphenylquinazoline-2-yl)carbazole, 9,10-bis(biphenyl)anthracene, 3-(10-phenyl-9-anthrayl)-dibenzofuran, etc.

[0404] Examples of dopants include fluorescent dopants and phosphorescent dopants.

[0405] Examples of fluorescent dopants include: anthracene, pyrene, tetraphenylene, xanthones, perylene, rubrene, coumarin, rhodamine, quinacridone, dicyanomethylenepyran compounds, thiaran compounds, polyacetylenes, pyrylium, thiaran compounds, fluorene derivatives, periflanthene derivatives, indo[a]perylene derivatives, bis(acrazinyl)amineboron compounds, bis(acrazinyl)methane compounds, quinolone compounds, boron compounds, cyclic amine compounds, etc. Fluorescent dopants may also be composed of combinations of two or more of these.

[0406] Examples of phosphorescent dopants include organometallic complexes of transition metals such as iridium, platinum, palladium, and osmium.

[0407] Specific examples of the fluorescent dopant and phosphorescent dopant include: Alq3 (tris(8-hydroxyquinoline)aluminum), DPAVBi (4,4′-bis[4-(di-p-tolylamino)styryl]biphenyl), perylene, 2,7-bis[N,N-di-(4-tert-butylphenyl)]amino-bisbenzofuran-9,9′-spirofluorene, bis[2-(4-n-hexylphenyl)quinoline](acetylacetone)iridium(III), Ir(PPy)3 (tris(2-phenylpyridine)iridium(III)) and FIrPic (bis(3,5-difluoro-2-(2-pyridyl)phenyl-(2-carboxypyridyl)iridium(III))), 5,9-diphenyl-5,9-dihydro-5,9-diaza-13b-boronaphtho[3,2,1-de]anthracene, etc.

[0408] Furthermore, the luminescent material is not limited to being contained only in the luminescent layer. For example, the layers adjacent to the luminescent layer (hole transport layer 4 or electron transport layer 6) may also contain the luminescent material. This can sometimes further improve the luminous efficiency of organic electroluminescent devices.

[0409] The light-emitting layer can be a single-layer structure containing one or more materials, or a multi-layered structure containing the same or different compositions.

[0410] (Preferred configuration of electron transport layer 6) An electron transport layer 6 is disposed between the light-emitting layer 5 and the cathode patterning layer 50, which will be described later.

[0411] The electron transport layer has the function of transferring electrons injected from the cathode to the light-emitting layer. By placing the electron transport layer between the cathode and the light-emitting layer, electrons can be injected into the light-emitting layer with a lower electric field.

[0412] Examples of materials that can be used as the electron transport layer include: tris(8-hydroxyquinoline)aluminum derivatives, imidazole derivatives, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoline derivatives, quinoxaline derivatives, oxadiazole derivatives, phosphole derivatives, thiophene derivatives, and phosphine oxide derivatives. Among these, triazine derivatives and pyrimidine derivatives are preferred from the perspective of good performance of organic electroluminescent elements.

[0413] In addition to the materials described above, the electron transport layer may also include one or more electron transport materials selected from those previously known.

[0414] (Preferred configuration of the cathode patterning layer 50) A cathode patterning layer 50 is provided between the electron transport layer 6 and the protective layer 9, which will be described later.

[0415] A cathode patterning layer 50 is disposed on an electron transport layer 6, and includes a patterning layer 7 and an electrode metal 8 patterned using the patterning layer 7.

[0416] Figure 6 It means Figure 1 A schematic cross-sectional view of an example of the formation of a cathode patterned layer.

[0417] exist Figure 6 In the direction from the anode 2 toward the protective layer 9, the area where the patterned layer 7 is present is the transparent area 51, and the area where the patterned layer 7 is not present (i.e., the electrode area 8) is the electrode area 52. It should be noted that the direction from the anode 2 toward the protective layer 9 in FIG. 11 is the upward direction perpendicular to the substrate 1.

[0418] Figure 6 In the transparent region 51, an electron transport layer 6 and a pattern layer 7 are sequentially stacked in the direction from the anode 2 toward the protective layer 9. The electron transport layer 6 and the pattern layer 7 are in direct contact and stacked.

[0419] Figure 6 In the electrode region 52, an electron transport layer 6 and an electrode metal 8 are sequentially stacked in the direction from the anode 2 toward the protective layer 9. The electron transport layer 6 is in direct contact with and stacked with the electrode metal 8.

[0420] It should be noted that, Figure 6 In this disclosure, the thickness of the patterned layer 7 and the thickness of the electrode metal 8 are expressed as the same thickness, but this disclosure is not limited to this. The patterned layer 7 may be thicker, or the electrode 8 may be thicker.

[0421] Figure 7 It means Figure 5 A schematic top view of an example of the configuration of the cathode patterned layer 50.

[0422] The electrode metal 8 is patterned by the patterning layer 7. The electrode metal 8 is preferably finely patterned. Here, finely patterned patterning includes patterning the patterned spacing of the cathode, which has the characteristics of a common organic electroluminescent element.

[0423] It should be noted that the patterned shape of the electrode metal 8 is arbitrary, and the patterned layer 7 can be formed in such a way that the shape of the electrode metal 8 becomes the desired shape.

[0424] The compounds shown in formulas (101) and (501) can be used as the material for the patterned layer.

[0425] (Preferred method for electrode metal 8) The electrode metal can be a single-layer structure containing one or more materials, or a multi-layer stacked structure containing the same or different compositions.

[0426] For example, the electrode metal is preferably formed of two layers: a cathode with high conductivity and an electron injection layer that has the function of transferring electrons injected from the cathode to the light-emitting layer.

[0427] (Preferred method for electron injection layer) An electron injection layer is provided on the electron transport layer 6.

[0428] The electron injection layer has the function of transferring electrons injected from the cathode to the light-emitting layer. By placing the electron injection layer between the cathode and the light-emitting layer, electrons can be injected into the light-emitting layer with a lower electric field.

[0429] Examples of materials that can be used as the electron injection layer include organic compounds such as fluorenone, anthraquinone dimethyl ether, biphenylquinone, thiaran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, methylene fluorene, anthraquinone dimethyl ether, and anthrone. In addition, inorganic compounds such as various oxides, fluorides, nitrides, and nitride oxides, such as SiO2, AlO, SiN, SiON, AlON, GeO, LiO, LiON, TiO, TiON, TaO, TaON, TaN, LiF, C, and Yb, can also be used as materials for the electron injection layer.

[0430] (Preferred cathode configuration) A cathode is disposed on the electron injection layer.

[0431] In the case of an organic electroluminescent element that only extracts light emitted through the anode, the cathode can be formed of any conductive material.

[0432] Materials that can be used as the cathode include, for example, metals with low work functions (hereinafter also referred to as electron-injecting metals), alloys, conductive compounds, and mixtures thereof. Here, metals with low work functions are, for example, metals with a work function of 4 eV or less.

[0433] Specific examples of cathode materials include: sodium, sodium-potassium alloy, magnesium, lithium, magnesium / copper mixture, magnesium / silver mixture, magnesium / aluminum mixture, magnesium / indium mixture, aluminum / alumina (Al2O3) mixture, indium, lithium / aluminum mixture, rare earth metals, etc.

[0434] From the viewpoint of electron injection properties and durability against oxidation, a mixture of an electron-injectable metal and a metal with a larger and more stable work function than the electron-injectable metal, i.e., a second metal, is preferred. Examples include magnesium / silver mixtures, magnesium / aluminum mixtures, magnesium / indium mixtures, aluminum / alumina (Al2O3) mixtures, lithium / aluminum mixtures, etc.

[0435] (Preferred method for protective layer 9) A protective layer 9 is provided on the cathode patterning layer 50.

[0436] From the perspective of improving light extraction efficiency, the protective layer is preferably a stacked structure comprising multiple layers with different refractive indices.

[0437] When the protective layer is composed of a laminated structure, the types of laminated layers are not particularly limited, but are preferably composed of 2 or more and 6 or less, 2 or more and 5 or less, 2 or more and 4 or less, 2 or more and 3 or less, and more preferably composed of 2 types of layers.

[0438] When the protective layer is formed by a laminated structure, it is preferable that at least one layer forming the laminated structure is a low refractive index layer and at least one layer is a high refractive index layer.

[0439] Methods for forming metallic patterns One aspect of this disclosure relates to a method for forming a metal pattern, which includes the following steps: The process of forming an organic material pattern on a substrate using the aforementioned metal patterning material, or a metal patterning material containing the aforementioned compound; and The process of applying a metallic material to the forming area and the non-forming area of ​​the organic material pattern to form a metallic pattern on the non-forming area.

[0440] Here, a metal patterning material is used to form a film on the substrate at the location where metal adhesion is to be suppressed. The location where metal adhesion is to be suppressed corresponds to the area where the organic material pattern is formed. The area other than the location where metal adhesion is to be suppressed corresponds to the non-formation area of ​​the organic material pattern. The non-formation area of ​​the organic material pattern is the area where metal adhesion is promoted, and is the location where the metal pattern is to be formed.

[0441] There are no particular limitations on the method for forming the organic material pattern (film formation method), and known methods such as vacuum deposition, spin coating, casting, dip coating, die coating, bar code coating, offset printing, spray coating, inkjet printing, screen printing, flexographic printing, gravure printing, and microcontact printing can be used. Furthermore, the film can be annealed at a temperature above room temperature after formation. There are also no particular limitations on the film thickness of the organic material pattern.

[0442] In metal patterned materials, other organic molecular materials, polymers, etc. can be added arbitrarily within the range that can suppress the formation of metal films on the film surface.

[0443] The substrate (base) for forming the organic material pattern can be either metallic or non-metallic, such as organic films, metal films, oxide films, inorganic films, etc., without particular limitations. Furthermore, the material of the substrate is also not particularly limited; glass, plastic, metal, ceramics, and all other materials can be used.

[0444] When the substrate for forming the organic material pattern is an organic film, the organic film can be, for example, tris(8-hydroxyquinoline)aluminum derivatives, imidazole derivatives, benzimidazole derivatives, triazine derivatives, pyrimidine derivatives, pyridine derivatives, pyrazine derivatives, quinoline derivatives, quinoxaline derivatives, oxadiazole derivatives, phosphacyclopentadiene derivatives, thiophene derivatives, phosphine oxide derivatives, etc.

[0445] There are no particular restrictions on the type of metal material used to create metal patterns when employing metal patterning materials. Alkali metals, alkaline earth metals, transition metals, and metals from Group 13 of the periodic table are preferred. More preferably lithium, sodium, potassium, rubidium, cesium, beryllium, magnesium, calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, gold, silver, platinum, copper, iron, palladium, molybdenum, manganese, titanium, cobalt, nickel, tungsten, tin, chromium, and alloys containing one or more of these metals.

[0446] Examples of such alloys include: magnesium-silver alloys, magnesium-indium alloys, magnesium-aluminum alloys, indium-silver alloys, lithium-aluminum alloys, lithium-magnesium alloys, lithium-indium alloys, calcium-aluminum alloys, etc.

[0447] By applying a metallic material to both the areas where the organic material pattern is formed and the areas where the organic material pattern is not formed, a film containing the metallic material is immediately formed on both areas. However, since the areas where the organic material pattern is formed inhibit the adhesion of the metallic material, the metallic pattern can be automatically formed only in the areas where the organic material pattern is not formed.

[0448] Specifically, as a method for forming the metal pattern, the methods shown in 1) to 2) below can be cited as examples.

[0449] 1) The metal patterned material is deposited into a film according to the desired pattern using a metal mask or the like.

[0450] 2) Next, by vapor deposition of metal, electrodes are formed only on the portions of the metal patterned material where no film has been formed. That is, a negative metal electrode is formed relative to the film pattern of the metal patterned material.

[0451] The area and linewidth of the patterned metal electrode can be arbitrarily adjusted according to the patterned shape of the metal patterning material.

[0452] In one aspect of this disclosure, a protective film can be formed on a patterned film made by patterning metal. Examples of protective films include organic films, oxide films, and inorganic films, and there are no particular limitations.

[0453] When the protective film is an organic film, the following can be used as examples of organic films: triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyaryl alkane derivatives, pyrazoline derivatives, pyrazolineone derivatives, phenylene diamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, styrene-anthracene derivatives, fluorenone derivatives, hydrazone derivatives, styrene derivatives, silazane derivatives, aniline copolymers, conductive polymer oligomers (especially thiophene oligomers), porphyrin compounds, aromatic tertiary amine compounds, carbazole compounds, styrene-amine compounds, triazine derivatives, pyrimidine derivatives, etc.

[0454] When the protective film is an inorganic film, silicon nitride, silicon oxide, etc. can be used as such an inorganic film.

[0455] According to one aspect of the present disclosure, a patterned metal material and a method for forming metal patterns can be used to form patterned structures of metal electrodes for solar cells, light sensors, image sensors, organic electroluminescent elements, organic solar cells, organic sensors, organic transistors, etc., or to form metal wiring on a circuit board.

[0456] The metal patterning material disclosed herein can also be applied to vapor deposition processes.

[0457] [Electronic Devices] One aspect of this disclosure relates to an electronic device that includes the metal patterning material or the compound.

[0458] In the electronic device, the metal patterning material preferably comprises the compound shown in formula (101).

[0459] As described above, in order to form an organic material pattern containing a metal patterning material, an organic material pattern can be formed together with the metal pattern. Therefore, an electronic device according to one aspect of this disclosure has an organic material pattern containing a metal pattern along with a metal pattern.

[0460] Examples of such electronic devices include solar cells, light sensors, image sensors, organic light-emitting diodes (OLEDs), organic solar cells, organic sensors, and organic transistors. These electronic devices possess patterned structures of metal electrodes or metal wiring on a circuit board. In other words, any electronic device possessing a patterned structure of metal electrodes or metal wiring on a circuit board can be used to obtain the electronic device described in this invention using the aforementioned metal pattern forming method. The aforementioned electronic device has a high-precision metal pattern.

[0461] Example The following describes some aspects of this disclosure in further detail based on embodiments, but the invention is not limited to any of these embodiments.

[0462] The compounds were identified by FDMS determination. The molecular weight results are shown in Table 1.

[0463] The transmittance was measured using the following apparatus.

[0464] [Transmittance Measurement] Measurement apparatus: V-750 manufactured by Japan Spectrophotometry Co., Ltd. Measurement range: 550~800nm.

[0465] Example 1 Synthesis of compound (Z8) [Chemistry 96]

[0466] Phloroglucinol (5.0 mmol), potassium carbonate (30 mmol), and 2-pentafluorothiobromoethane (20.0 mmol) were added to THF and stirred at 70 °C. After 4 hours, citric acid solution was added for neutralization, followed by extraction three times with ethyl acetate. The organic phase was dehydrated with sodium sulfate, filtered, and concentrated to obtain a crude product. The crude product was purified by column chromatography (hexane:ethyl acetate) to obtain Z8 (yield 30%) as the target product.

[0467] Example 2 Synthesis of compound (Z9) [Chemistry 97]

[0468] In THF, Z9 (yield 12%) was obtained as the target product by the same synthesis method as in Example 1, using phloroglucinol (5.0 mmol), potassium carbonate (30 mmol) and 3-pentafluorothiobromopropane (20.0 mmol).

[0469] Example 3 Synthesis of compound (Z14) [Chem. 98]

[0470] In THF, using 1,3,5-benzenetrithiophenol (5.0 mmol), potassium carbonate (30 mmol), and 2-pentafluorothiobromoethane (20.0 mmol), Z14 (yield 49%) was obtained as the target product by the same synthesis method as in Example 1.

[0471] Example 4 Synthesis of compound (Z15) [Chemistry 99]

[0472] In THF, using 1,3,5-benzenetrithiophenol (5.0 mmol), potassium carbonate (30 mmol), and 3-pentafluorothiobromopropane (20.0 mmol), Z9 (yield 41%) was obtained as the target product by the same synthesis method as in Example 1.

[0473] Example 5 Synthesis of compound (Z19) [Chemistry 100]

[0474] In THF, using 1,3,5-phenyltriamine (5.0 mmol), potassium carbonate (30 mmol), and 2-pentafluorothiobromoethane (50.0 mmol), Z19 (yield 19%) was obtained as the target product by the same synthesis method as in Example 1.

[0475] Example 6 Synthesis of compound (Z20) [Chemistry 101]

[0476] In THF, using 1,3,5-phenyltriamine (5.0 mmol), potassium carbonate (30 mmol), and 3-pentafluorothiobromopropane (50.0 mmol), Z20 (yield 34%) was obtained as the target product by the same synthesis method as in Example 1.

[0477] Example 7 Synthesis of compound (Z22) [Chemistry 102]

[0478] In THF, using 1,3,5-tris(hexylamine)benzene (5.0 mmol), potassium carbonate (30 mmol), and 2-pentafluorothiobromoethane (20.0 mmol), Z22 (yield 23%) was obtained as the target product by the same synthesis method as in Example 1.

[0479] Example 8 Synthesis of compound (Z23) [Chemistry 103]

[0480] In THF, using 3,5-bis(dimethylamine)aniline (5.0 mmol), potassium carbonate (30 mmol), and 3-pentafluorothiobromopropane (20.0 mmol), Z23 (yield 47%) was obtained as the target product by the same synthesis method as in Example 1.

[0481] Example 9 Synthesis of compound (Z24) [Chemistry 104]

[0482] In THF, using 1,3,5-tris(phenylamine)amine (5.0 mmol), potassium carbonate (30 mmol), and 3-pentafluorothiobromopropane (20.0 mmol), Z24 (67% yield) was obtained as the target product by the same synthesis method as in Example 1.

[0483] Example 10 Synthesis of compound (Z27) [Chemistry 105]

[0484] In THF, using 2,6-dihydroxyanthracene (5.0 mmol), potassium carbonate (30 mmol), and 3-pentafluorothiobromopropane (20.0 mmol), Z27 (yield 41%) was obtained as the target product by the same synthesis method as in Example 1.

[0485] Example 11 Synthesis of compound (Z38) [Chemistry 106]

[0486] Under a nitrogen atmosphere, 100 mL of THF was added to magnesium powder (1.0 mmol), followed by 10 mL of THF in 2-pentafluorothiobromoethane (9.0 mmol) at room temperature. After stirring for 1 hour, a THF solution of 2,4,6-trichloropyrimidine (3.0 mmol) was slowly added, and the mixture was stirred for another 3 hours. After the reaction was complete, 100 mL of water was added, and the mixture was stirred for 1 hour. The mixture was then extracted three times with ethyl acetate. The organic phase was dehydrated with sodium sulfate, filtered, and concentrated to obtain a crude product. The crude product was purified by column chromatography (hexane:ethyl acetate) to obtain Z38 (yield 10%) as the target product.

[0487] Example 12 Synthesis of compound (Z40) [Chemistry 107]

[0488] Z40 (yield 20%), the target product, was obtained by the same synthesis method as in Example 11 using 3-pentafluorothiobromopropane (9.0 mmol) and 2,4,6-trichloropyrimidine (3.0 mmol).

[0489] Example 13 Synthesis of compound (Z44) [Chemistry 108]

[0490] 2,4,6-Trichloropyrimidine (5.0 mmol), potassium carbonate (30 mmol), and 2-pentafluorothioethanol (20.0 mmol) were added to THF and stirred at 70 °C. After 4 hours, citric acid solution was added for neutralization, followed by extraction three times with ethyl acetate. The organic phase was dehydrated with sodium sulfate, filtered, and concentrated to obtain a crude product. The crude product was purified by column chromatography (hexane:ethyl acetate) to obtain Z44 (yield 41%) as the target product.

[0491] Example 14 Synthesis of compound (Z45) [Chemistry 109]

[0492] In THF, using 2,4,6-trichloropyrimidine (5.0 mmol), potassium carbonate (30 mmol), and 3-pentafluorothiopropanol (20.0 mmol), Z45 (yield 34%) was obtained as the target product by the same synthetic method as in Example 36.

[0493] Example 15 Synthesis of compound (Z48) [Chemical 110]

[0494] In THF, using 2,4-dichloroquinazoline (5.0 mmol), potassium carbonate (30 mmol), and 2-pentafluorothioethanol (20.0 mmol), Z48 (65% yield) was obtained as the target product by the same synthesis method as in Example 36.

[0495] Synthesis Example 1: Synthesis of Intermediate 1 [Chemistry 111]

[0496] Under a nitrogen atmosphere, 2-pentafluorothiobromoethane (9.0 mmol) and potassium thioacetate were added to acetonitrile (100 mL) at room temperature. After stirring at 80 °C for 6 hours, water (100 mL) was added, and the mixture was stirred for 1 hour. The mixture was extracted three times with ethyl acetate. The organic phase was dehydrated with sodium sulfate, filtered, and concentrated to obtain a crude product. Pyrrolidine (12 mmol) was further added to the crude product, and after stirring for 30 minutes, the mixture was concentrated and purified by vacuum distillation to obtain intermediate 1 (80% yield) as the target product.

[0497] Example 16 Synthesis of compound (Z49) [Chemistry 112]

[0498] Under a nitrogen atmosphere in THF, using 2,4,6-trichloropyrimidine (5.0 mmol), potassium carbonate (30 mmol), and intermediate 1 (20.0 mmol), Z49 (yield 44%) was obtained as the target product by the same synthesis method as in Example 36.

[0499] Synthesis Example 2: Synthesis of Intermediate 2 [Chemistry 113]

[0500] Under a nitrogen atmosphere, 2-pentafluorothiobromopropane (9.0 mmol) and potassium thioacetate were added to acetonitrile (100 mL) at room temperature. After stirring at 80 °C for 6 hours, water (100 mL) was added, and the mixture was stirred for 1 hour. The mixture was extracted three times with ethyl acetate. The organic phase was dehydrated with sodium sulfate, filtered, and concentrated to obtain a crude product. Pyrrolidine (12 mmol) was further added to the crude product, and after stirring for 30 minutes, the mixture was concentrated and purified by vacuum distillation to obtain intermediate 2 (yield 87%), which was the target product.

[0501] Example 17 Synthesis of compound (Z50) [Chemistry 114]

[0502] In THF, using 2,4,6-trichloropyrimidine (5.0 mmol), potassium carbonate (30 mmol), and intermediate 2 (20.0 mmol), Z50 (yield 46%) was obtained as the target product by the same synthesis method as in Example 36.

[0503] Example 18 Synthesis of compound (Z51) [Chemistry 115]

[0504] In THF, using 2,4-dichloroquinazoline (5.0 mmol), potassium carbonate (30 mmol), and intermediate 1 (20.0 mmol), Z51 (69% yield) was obtained as the target product by the same synthesis method as in Example 36.

[0505] Example 19 Synthesis of compound (Z53) [Chemistry 116]

[0506] In THF, using 2,4-dichloro-6-phenylpyrimidine (5.0 mmol), potassium carbonate (30 mmol), and intermediate 2 (12.0 mmol), Z53 (61% yield) was obtained as the target product by the same synthesis method as in Example 36.

[0507] Synthesis Example 3: Synthesis of Intermediate 3 [Chemistry 117]

[0508] In THF (100 mL), 2-naphthylamine and potassium carbonate were added to 2,4,6-trichloropyrimidine (5.0 mmol) (9.0 mmol) at room temperature. After stirring at 80 °C for 6 hours, water (100 mL) was added, and the mixture was stirred for 1 hour. The mixture was extracted three times with ethyl acetate. The organic phase was dehydrated with sodium sulfate, filtered, and concentrated to obtain the crude product. The crude product was purified by column chromatography (ethyl acetate) to obtain intermediate 3 (yield 8%), which was the target product.

[0509] Example 20 Synthesis of compound (Z56) [Chemistry 118]

[0510] In THF, using intermediate 3 (5.0 mmol), potassium carbonate (30 mmol), and 3-pentafluorothiobromoethane (20.0 mmol), Z56 (yield 20%) was obtained as the target product via the same synthetic method as in Example 1. Example 21 Synthesis of compound (Z58) [Chemistry 119]

[0511] In THF, using 2,4-quinazolindiamine (5.0 mmol), tripotassium phosphate (30 mmol), and 2-pentafluorothiobromoethane (20.0 mmol), Z58 (yield 41%) was obtained as the target product via the same synthesis method as in Example 1.

[0512] Example 22 Synthesis of compound (Z59) [Chemistry 120]

[0513] Under a nitrogen atmosphere and in THF, using 2,4-quinazolindiamine (5.0 mmol), tripotassium phosphate (30 mmol), and 3-pentafluorothiobromopropane (20.0 mmol), Z59 (51% yield) was obtained as the target product by the same synthesis method as in Example 1.

[0514] Example 23 Synthesis of compound (Z73) [Chemistry 121]

[0515] Under a nitrogen atmosphere, using 2-pentafluorothiobromoethane (9.0 mmol) and cyanuric chloride (3.0 mmol), Z73 (67% yield) was obtained as the target product by the same synthesis method as in Example 11.

[0516] Example 24 Synthesis of compound (Z74) [Chemistry 122]

[0517] Under a nitrogen atmosphere, Z74 (yield 41%) was obtained as the target product by the same synthesis method as in Example 11 using 3-pentafluorothiobromopropane (9.0 mmol) and cyanuric chloride (3.0 mmol).

[0518] Example 25 Synthesis of compound (Z77) [Chemistry 123]

[0519] Under a nitrogen atmosphere, Z77 (yield 32%) was obtained as the target product by the same synthesis method as in Example 11 using 3-pentafluorothiobromopropane (8.0 mmol) and 9-(4,6-dichloro-1,3,5-triazin-2-yl)-9H-carbazole (3.0 mmol).

[0520] Example 26 Synthesis of compound (Z78) [Chemistry 124]

[0521] Under a nitrogen atmosphere, Z78 (yield 29%) was obtained as the target product by the same synthesis method as in Example 11 using 3-pentafluorothiobromopropane (8.0 mmol) and 9-(4,6-dichloro-1,3,5-triazin-2-yl)-1H-indole (3.0 mmol).

[0522] Example 27 Synthesis of compound (Z79) [Chemistry 125]

[0523] In THF, using cyanuric chloride (5.0 mmol), lithium carbonate (30 mmol), and 3-pentafluorothioethanol (20.0 mmol), Z79 (yield 28%) was obtained as the target product by the same synthesis method as in Example 36.

[0524] Example 27 Synthesis of compound (Z80) [Chemistry 126]

[0525] In THF, using cyanuric chloride (5.0 mmol), potassium carbonate (30 mmol), and 3-pentafluorothiopropanol (20.0 mmol), Z80 (yield 36%) was obtained as the target product by the same synthesis method as in Example 36.

[0526] Synthesis Example 4: Synthesis of Intermediate 4 [Chemistry 127]

[0527] Under a nitrogen atmosphere, cyanuric chloride (5.0 mmol), 4-methoxyphenol (20.0 mmol), and potassium carbonate were added to 100 mL of THF at room temperature. After stirring at 80 °C for 6 hours, water (100 mL) was added, and the mixture was stirred for 1 hour. The mixture was extracted three times with ethyl acetate. The organic phase was dehydrated with sodium sulfate, filtered, and concentrated to obtain a crude product. The crude product was purified by column chromatography (ethyl acetate) to obtain intermediate 4 (yield 40%), which was the target product.

[0528] Synthesis Example 5: Synthesis of Intermediate 5 [Chemistry 128]

[0529] Under a nitrogen atmosphere, intermediate 4 (5.0 mmol) was added to an aqueous solution of hydrogen bromide (500 ml), and stirred at 100 °C for 24 hours. Water (100 ml) was then added, and the mixture was stirred for 1 hour. The mixture was extracted three times with toluene. The organic phase was dehydrated with sodium sulfate, filtered, and concentrated to obtain a crude product. This crude product was purified by column chromatography (ethyl acetate) to obtain intermediate 5 (80% yield), which was the target product.

[0530] Example 29 Synthesis of compound (Z81) [Chemistry 129]

[0531] Under a nitrogen atmosphere, Z81 (yield 41%) was obtained as the target product by the same synthesis method as in Example 1 using intermediate 5 (5.0 mmol), tripotassium phosphate (30 mmol), and 2-pentafluorothiobromoethane (20.0 mmol) in THF.

[0532] Synthesis Example 6: Synthesis of Intermediate 6 [Chemistry 130]

[0533] Under a nitrogen atmosphere, cyanuric chloride (5.0 mmol), 3,5-dimethoxyphenol (20.0 mmol), and potassium carbonate were added to 100 mL of THF at room temperature. After stirring at 80 °C for 6 hours, water (100 mL) was added, and the mixture was stirred for 1 hour. The mixture was extracted three times with ethyl acetate. The organic phase was dehydrated with sodium sulfate, filtered, and concentrated to obtain a crude product. The crude product was purified by column chromatography (ethyl acetate) to obtain intermediate 6 (70% yield) as the target product.

[0534] Synthesis Example 7: Synthesis of Intermediate 7 [Chemistry 131]

[0535] Under a nitrogen atmosphere, intermediate 6 (5.0 mmol) was added to an aqueous solution of hydrogen bromide (500 ml), and stirred at 100 °C for 24 hours. Then, water (100 ml) was added, and the mixture was stirred for 1 hour. The mixture was extracted three times with toluene. The organic phase was dehydrated with sodium sulfate, filtered, and concentrated to obtain a crude product. This crude product was purified by column chromatography (ethyl acetate) to obtain intermediate 7 (40% yield), which was the target product.

[0536] Example 30 Synthesis of compound (Z82) [Chemistry 132]

[0537] Under a nitrogen atmosphere, Z82 (yield 12%) was obtained as the target product by the same synthesis method as in Example 1, using intermediate 5 (5.0 mmol), tripotassium phosphate (30 mmol), and 3-pentafluorothiobromopropane (20.0 mmol) in THF.

[0538] Example 31 Synthesis of compound (Z85) [Chemistry 133]

[0539] In THF, using cyanuric chloride (5.0 mmol), tripotassium phosphate (30 mmol), and intermediate 1 (20.0 mmol), Z85 (yield 19%) was obtained as the target product by the same synthesis method as in Example 36.

[0540] Example 32 Synthesis of compound (Z86) [Chemistry 134]

[0541] In THF, using cyanuric chloride (5.0 mmol), potassium carbonate (30 mmol), and intermediate 2 (20.0 mmol), Z86 (yield 21%) was obtained as the target product by the same synthesis method as in Example 36.

[0542] Example 33 Synthesis of compound (Z91) [Chemistry 135]

[0543] In THF, using 1,3,5-triazine-2,4,6-tri(methylamine) (5.0 mmol), tripotassium phosphate (30 mmol), and 2-pentafluorothiobromoethane (20.0 mmol), Z91 (yield 21%) was obtained as the target product by the same synthesis method as in Example 1.

[0544] Example 34 Synthesis of compound (Z92) [Chemistry 136]

[0545] Under a nitrogen atmosphere, Z92 (yield 19%) was obtained as the target product by the same synthesis method as in Example 1 using 1,3,5-triazine-2,4,6-tri(methylamine) (5.0 mmol), tripotassium phosphate (30 mmol) and 3-pentafluorothiobromopropane (20.0 mmol) in THF.

[0546] Example 35 Synthesis of compound (Z93) [Chemistry 137]

[0547] Under a nitrogen atmosphere, Z93 (yield 41%) was obtained as the target product by the same synthesis method as in Example 1 using 1,3,5-triazine-4,6-bis(dimethylamine)-2-amine (5.0 mmol), tripotassium phosphate (30 mmol), and 2-pentafluorothiobromoethane (20.0 mmol) in THF.

[0548] Example 36 Synthesis of compound (Z94) [Chemistry 138]

[0549] Under a nitrogen atmosphere, Z94 (yield 41%) was obtained as the target product by the same synthesis method as in Example 1 using 1,3,5-triazine-2,4,6-tris(phenylamine) (5.0 mmol), tripotassium phosphate (30 mmol), and 3-pentafluorothiobromopropane (20.0 mmol) in THF.

[0550] Synthesis Example 8: Synthesis of Intermediate 8 [Chemistry 139]

[0551] Under a nitrogen atmosphere, 15.0 mmol of 2,4,6-trimethylpyridine and 15.0 mmol of 2-pentafluorothioethanol were added to 100 mL of THF at room temperature. A solution of cyanuric chloride in THF (50 mL) was added dropwise over 6 hours at 80 °C, followed by stirring for 1 hour. Then, 100 mL of water was added, and the mixture was stirred for 1 hour. The mixture was extracted three times with ethyl acetate, and the organic phase was washed four times with citric acid solution. The organic layer was dehydrated with sodium sulfate, filtered, and concentrated to give intermediate 8 (95% yield).

[0552] Synthesis Example 9: Synthesis of Intermediate 9 [Chemistry 140]

[0553] Under a nitrogen atmosphere, 15.0 mmol of 2,4,6-trimethylpyridine and 15.0 mmol of 3-pentafluorothiopropanol were added to 100 mL of THF at room temperature. A solution of cyanuric chloride in THF (50 mL) was added dropwise over 6 hours at 80 °C, followed by stirring for 1 hour. Then, 100 mL of water was added, and the mixture was stirred for 1 hour. The mixture was extracted three times with ethyl acetate, and the organic phase was washed four times with citric acid solution. The organic layer was dehydrated with sodium sulfate, filtered, and concentrated to give intermediate 9 (95% yield).

[0554] Example 37 Synthesis of compound (Z101) [Chemistry 141]

[0555] Under a nitrogen atmosphere, 1,4-dihydroxycyclohexane (5.0 mmol), tripotassium phosphate (30 mmol), and intermediate 8 (12.0 mmol) were added to THF and stirred at 70 °C. After 24 hours, citric acid solution was added for neutralization, followed by extraction three times with ethyl acetate. The organic phase was dehydrated with sodium sulfate, filtered, and concentrated to obtain a crude product. The crude product was purified by column chromatography (hexane:ethyl acetate) to obtain the target product Z101 (yield 74%).

[0556] Example 38 Synthesis of compound (Z102) [Chemistry 142]

[0557] Under a nitrogen atmosphere, Z102 (67% yield) was obtained as the target product by the same synthesis method as in Example 37 using 1,3-dihydroxyadamantane (5.0 mmol), tripotassium phosphate (30 mmol) and intermediate 9 (12.0 mmol) in THF.

[0558] Synthesis Example 10: Synthesis of Intermediate 10 [Chemistry 143]

[0559] Under a nitrogen atmosphere, 5-bromoresorcinol (5.0 mmol), tripotassium phosphate (30 mmol), and 2-pentafluorothiobromoethane (12.0 mmol) were added to 100 mL of THF and stirred at room temperature for 2 hours. The mixture was then further heated to 80 °C and stirred for 12 hours. Water (100 mL) was added, and the mixture was stirred for 1 hour. The mixture was extracted three times with ethyl acetate. The organic layer was dehydrated with sodium sulfate, filtered, concentrated, and purified by column chromatography (hexane:ethyl acetate) to give intermediate 10 (68% yield).

[0560] Example 39 Synthesis of compound (Z114) [Chemistry 144]

[0561] Under a nitrogen atmosphere, bis(pinacol) 1,4-phenylenediborate (5.0 mmol), tripotassium phosphate aqueous solution (30 mmol), intermediate 10 (12.0 mmol), palladium acetate (0.05 mmol), and triphenylphosphine (0.05 mmol) were added to THF and stirred at 70 °C. After 24 hours, citric acid solution was added for neutralization, followed by extraction three times with ethyl acetate. The organic phase was dehydrated with sodium sulfate, filtered, and concentrated to obtain a crude product. The crude product was purified by column chromatography (hexane:ethyl acetate) to obtain the target product Z114 (yield 72%).

[0562] Synthesis Example 11: Synthesis of Intermediate 11 [Chemistry 145]

[0563] Under a nitrogen atmosphere, intermediate 11 (70% yield) was obtained by the same synthetic method as in Example 1 using 4-bromophenol (5.0 mmol) and 2-pentafluorothiobromoethane (6.0 mmol).

[0564] Synthesis Example 12: Synthesis of Intermediate 12 [Chemistry 146]

[0565] Under a nitrogen atmosphere, intermediate 11 (5.0 mmol), potassium acetate (30 mmol), palladium acetate (0.05 mmol), triphenylphosphine (0.05 mmol), and bis(pinacol)diboron (6.0 mmol) were added to 100 mL of THF and stirred at 70 °C for 2 hours. Then, water (100 mL) was added, and the mixture was stirred for 1 hour, followed by extraction three times with ethyl acetate. The organic layer was dehydrated with sodium sulfate, filtered, and concentrated to obtain intermediate 12 (90% yield).

[0566] Synthesis Example 13: Synthesis of Intermediate 13 [Chemistry 147]

[0567] Under a nitrogen atmosphere, intermediate 13 (62% yield) was obtained by the same synthesis method as in Example 1 using 3,5-dibromophenol (5.0 mmol) and 2-pentafluorothiobromoethane (12.0 mmol).

[0568] Example 40 Synthesis of compound (Z115) [Chemistry 148]

[0569] Under a nitrogen atmosphere in THF, using intermediates 12 (10.0 mmol) and 13 (5.0 mmol), Z115 (50% yield) was obtained as the target product by the same synthesis method as in Example 39.

[0570] Example 41 Synthesis of compound (Z116) [Chemistry 149]

[0571] Under a nitrogen atmosphere, Z116 (60% yield) was obtained as the target product by the same synthesis method as in Example 39 using 1,2-phenyldiboronic acid bis(pinacol) ester (5.0 mmol) and intermediate 10 (12.0 mmol) in THF.

[0572] Example 42 Synthesis of compound (Z117) [Chemistry 150]

[0573] Under a nitrogen atmosphere, using 1,4-naphthalenediboronic acid bis(pinacol) ester (5.0 mmol) and intermediate 10 (12.0 mmol), Z117 (71% yield) was obtained as the target product by the same synthesis method as in Example 39.

[0574] Example 43 Synthesis of compound (Z118) [Chemistry 151]

[0575] Under a nitrogen atmosphere, using intermediate 11 (5.0 mmol) and 2,6-dibromonaphthalene (2.0 mmol), Z118 (yield 41%) was obtained as the target product by the same synthesis method as in Example 39.

[0576] Synthesis Example 14: Synthesis of Intermediate 14 [Chemistry 152]

[0577] Under a nitrogen atmosphere, intermediate 14 (73% yield) was obtained by the same synthetic method as in Example 1 using 5-methoxyresorcinol (5.0 mmol) and 2-pentafluorothiobromoethane (12.0 mmol).

[0578] Synthesis Example 15: Synthesis of Intermediate 15 [Chemistry 153]

[0579] Intermediate 14 (5.0 mmol) was stirred at 100 °C for 24 hours in an aqueous hydrogen bromide solution (100 mL) under a nitrogen atmosphere. Then, water (100 mL) was added, and the mixture was stirred at below 10 °C for 1 hour. After filtration, the mixture was purified by column chromatography (hexane:ethyl acetate) to obtain intermediate 15 (yield 80%).

[0580] Example 44 Synthesis of compound (Z121) [Chemistry 154]

[0581] Under a nitrogen atmosphere, in xylene, using intermediates 15 (5.0 mmol) and 10 (5.0 mmol), Z121 (yield 11%), the target product, was obtained by the same synthesis method as in Example 44.

[0582] Synthesis Example 16: Synthesis of Intermediate 16 [Chemistry 155]

[0583] Under a nitrogen atmosphere, intermediate 16 was obtained by the same synthetic method as in Example 1 using 5-bromoresorcinol (5.0 mmol) and 3-pentafluorothiobromopropane (12.0 mmol).

[0584] Synthesis Example 17: Synthesis of Intermediate 17 [Chemistry 156]

[0585] Under a nitrogen atmosphere, intermediate 17 (yield 81%) was obtained by the same synthetic method as in Example 1 using 3,5-dihydroxy-1-methylthiobenzene (5.0 mmol) and 3-pentafluorothiobromopropane (12.0 mmol).

[0586] Synthesis Example 18: Synthesis of Intermediate 18 [Chemistry 157]

[0587] Intermediate 16 (5.0 mmol) was stirred at 100 °C for 24 hours in an aqueous hydrogen bromide solution (100 mL) under a nitrogen atmosphere. Then, water (100 mL) was added, and the mixture was stirred at below 10 °C for 1 hour. After filtration, the mixture was purified by column chromatography (hexane:ethyl acetate) to obtain intermediate 18 (yield 30%).

[0588] Example 45 Synthesis of compound (Z122) [Chemistry 158]

[0589] Under a nitrogen atmosphere and in xylene, using intermediates 16 (5.0 mmol) and 18 (5.0 mmol), Z122 (yield 21%), the target product, was obtained by the same synthesis method as in Example 44.

[0590] Example 46 Synthesis of compound (Z125) [Chemistry 159]

[0591] Under a nitrogen atmosphere and in xylene, using intermediate 16 (5.0 mmol) and aniline (2.0 mmol), Z125 (yield 27%) was obtained as the target product by the same synthesis method as in Example 44.

[0592] Example 47 Synthesis of compound (Z126) [Chemistry 160]

[0593] Under a nitrogen atmosphere, using 5,5′-iminobis[1,3-phenylene glycol] (5.0 mmol) and 3-pentafluorothiobromopropane (20.0 mmol), Z126 (65% yield) was obtained as the target product by the same synthesis method as in Example 1.

[0594] Synthesis Example 19: Synthesis of Intermediate 19 [Chemistry 161]

[0595] Under a nitrogen atmosphere, intermediate 19 (yield 80%), the target product, was obtained by the same synthetic method as in Example 13 using 2,4,6-trichloropyrimidine (5.0 mmol) and 2-pentafluorothioethanol (20.0 mmol).

[0596] Example 48 Synthesis of compound (Z131) [Chemistry 162]

[0597] Under a nitrogen atmosphere, using bis(pinacol) 1,4-phenylenediborate (5.0 mmol) and intermediate 19, Z131 (yield 32%) was obtained as the target product via the same synthetic method as in Example 39. Synthesis Example 20: Synthesis of Intermediate 20 [Chemistry 163]

[0598] Under a nitrogen atmosphere, 2,4,6-trichloropyrimidine (5.0 mmol), tripotassium phosphate (30 mmol), and 2-pentafluorothioethanol (10.0 mmol) were added to THF and stirred at 70 °C. After 24 hours, citric acid solution was added for neutralization, followed by extraction three times with ethyl acetate. The organic phase was dehydrated with sodium sulfate, filtered, and concentrated to obtain intermediate 20 (90% yield) as the target product.

[0599] Example 49 Synthesis of compound (Z132) [Chemistry 164]

[0600] Under a nitrogen atmosphere, using 1,4-phenyldiboronic acid bis(pinacol) ester (5.0 mmol) and intermediate 20 (12.0 mmol), Z132 (yield 41%), the target product, was obtained by the same synthesis method as in Example 39.

[0601] Example 50 Synthesis of compound (Z133) [Chemistry 165]

[0602] Under a nitrogen atmosphere, using 1,4-phenyldiboronic acid bis(pinacol) ester (5.0 mmol) and intermediate 8 (12.0 mmol), Z133 (yield 36%), the target product, was obtained by the same synthesis method as in Example 39.

[0603] Example 51 Synthesis of compound (Z134) [Chemistry 166]

[0604] Under a nitrogen atmosphere, using 1,4-naphthalenediboronic acid bis(pinacol) ester (5.0 mmol) and intermediate 20 (12.0 mmol), Z134 (yield 41%), the target product, was obtained by the same synthesis method as in Example 39.

[0605] Example 52 Synthesis of compound (Z135) [Chemistry 167]

[0606] Under a nitrogen atmosphere, using 1,4-naphthalenediboronic acid bis(pinacol) ester (5.0 mmol) and intermediate 20 (12.0 mmol), Z135 (yield 33%), the target product, was obtained by the same synthesis method as in Example 39.

[0607] Example 53 Synthesis of compound (Z136) [Chemistry 168]

[0608] Under a nitrogen atmosphere, using 1,4-naphthalenediboronic acid bis(pinacol) ester (5.0 mmol) and intermediate 8 (12.0 mmol), Z136 (yield 25%), the target product, was obtained by the same synthesis method as in Example 39.

[0609] Example 54 Synthesis of compound (Z141) [Chemistry 169]

[0610] Under a nitrogen atmosphere, using 1,4-cyclohexanediboronate bis(pinacol) ester (5.0 mmol) and intermediate 21 (12.0 mmol), Z141 (yield 9%), the target product, was obtained by the same synthesis method as in Example 39.

[0611] Example 55 Synthesis of compound (Z142) [Chemistry 170]

[0612] Under a nitrogen atmosphere, using 1,4-cyclohexanediboronate bis(pinacol) ester (5.0 mmol) and intermediate 8 (12.0 mmol), Z142 (7% yield) was obtained as the target product by the same synthesis method as in Example 39.

[0613] Synthesis Example 21: Synthesis of Intermediate 21 [Chemistry 171]

[0614] Under a nitrogen atmosphere, 2,4,6-trifluoropyridine (5.0 mmol), piperazine (12.0 mmol), and tripotassium phosphate (30 mmol) were added, and the mixture was stirred at 70 °C. After 24 hours, citric acid solution was added for neutralization, followed by extraction three times with ethyl acetate. The organic phase was dehydrated with sodium sulfate, filtered, and concentrated to obtain a crude product. The crude product was purified by column chromatography (hexane:ethyl acetate) to obtain intermediate 21 (50% yield) as the target product.

[0615] Example 56 Synthesis of compound (Z143) [Chemistry 172]

[0616] Under a nitrogen atmosphere, intermediate 22 (5.0 mmol), tripotassium phosphate (30 mmol), and 2-pentafluorothioethanol (40.0 mmol) were added to THF and stirred at 70 °C. After 24 hours, citric acid solution was added for neutralization, followed by extraction three times with ethyl acetate. The organic phase was dehydrated with sodium sulfate, filtered, and concentrated to obtain a crude product. The crude product was purified by column chromatography (hexane:ethyl acetate) to obtain compound Z143 (yield 45%) as the target product.

[0617] Synthesis Example 22: Synthesis of Intermediate 22 [Chemistry 173]

[0618] Under a nitrogen atmosphere, using perfluoropyridine (5.0 mmol) and piperazine (12.0 mmol) in THF, intermediate 22 (60% yield) was obtained as the target product through the same synthesis method as in Synthesis Example 21.

[0619] Example 57 Synthesis of compound (Z144) [Chemistry 174]

[0620] Under a nitrogen atmosphere, using intermediate 23 (5.0 mmol) and 2-pentafluorothioethanol (40.0 mmol) in THF, the compound Z144 (yield 40%), as the target product, was obtained by the same synthesis method as in Example 56.

[0621] Example 58 Synthesis of compound (Z145) [Chemistry 175]

[0622] Under a nitrogen atmosphere in THF, using intermediate 21 (10.0 mmol) and piperazine (4.0 mmol), the compound Z145 (60% yield) was obtained as the target product by the same synthetic method as in Synthetic Example 21.

[0623] Example 59 Synthesis of compound (Z146) [Chemistry 176]

[0624] Under a nitrogen atmosphere in THF, using intermediate 19 (10.0 mmol) and piperazine (4.0 mmol), the compound Z146 as the target product was obtained by the same synthesis method as in Synthesis Example 21.

[0625] Example 60 Synthesis of compound (Z147) [Chemistry 177]

[0626] Under a nitrogen atmosphere in THF, using intermediate 8 (10.0 mmol) and piperazine (4.0 mmol), the compound Z147 (yield 43%), the target product, was obtained by the same synthetic method as in Synthetic Example 21.

[0627] Example 61 Synthesis of compound (Z148) [Chemistry 178]

[0628] Under a nitrogen atmosphere and in THF, using intermediate 21 (10.0 mmol) and piperazine (4.0 mmol), the compound Z148 (62% yield) was obtained as the target product by the same synthetic method as in Synthetic Example 21.

[0629] Example 62 Synthesis of compound (Z149) [Chemistry 179]

[0630] Under a nitrogen atmosphere and in THF, using intermediate 20 (10.0 mmol) and piperazine (4.0 mmol), the compound Z146 (yield 52%), as the target product, was obtained by the same synthesis method as in Synthesis Example 21.

[0631] Example 63 Synthesis of compound (Z150) [Chemistry 180]

[0632] Under a nitrogen atmosphere and in THF, using intermediate 8 (10.0 mmol) and piperazine (4.0 mmol), the compound Z150 as the target product was obtained by the same synthesis method as in Synthesis Example 21.

[0633] Example 64 Synthesis of compound (Z151) [Chemistry 181]

[0634] Under a nitrogen atmosphere and in THF, using intermediate 21 (10.0 mmol) and 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine (4.0 mmol), the compound Z151 as the target product was obtained by the same synthetic method as in Synthetic Example 21.

[0635] Example 65 Synthesis of compound (Z152) [Chemistry 182]

[0636] Under a nitrogen atmosphere and in THF, using intermediate 20 (10.0 mmol) and 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine (4.0 mmol), the compound Z152, the target product, was obtained by the same synthesis method as in Synthesis Example 21.

[0637] Example 66 Synthesis of compound (Z153) [Chemistry 183]

[0638] Under a nitrogen atmosphere and in THF, using intermediate 8 (10.0 mmol) and 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine (4.0 mmol), the compound Z153 (yield 32%), as the target product, was obtained by the same synthetic method as in Synthetic Example 21.

[0639] Example 67 Synthesis of compound (Z154) [Chemistry 184]

[0640] Under a nitrogen atmosphere and in THF, using intermediate 21 (10.0 mmol) and 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine (4.0 mmol), the compound Z154 (yield 42%), as the target product, was obtained by the same synthetic method as in Synthetic Example 21.

[0641] Example 68 Synthesis of compound (Z155) [Chemistry 185]

[0642] Under a nitrogen atmosphere and in THF, using intermediate 20 (10.0 mmol) and 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine (4.0 mmol), the compound Z155 (yield 49%), as the target product, was obtained by the same synthetic method as in Synthetic Example 21.

[0643] Example 69 Synthesis of compound (Z156) [Chemistry 186]

[0644] Under a nitrogen atmosphere and in THF, using intermediate 8 (10.0 mmol) and 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine (4.0 mmol), the compound Z156 as the target product was obtained by the same synthesis method as in Synthesis Example 21.

[0645] Example 70 Synthesis of compound (Z164) [Chemistry 187]

[0646] Under a nitrogen atmosphere, in xylene, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine (2.0 mmol), intermediate 10 (5.0 mmol), sodium tert-butoxy (20 mmol), palladium acetate (0.05 mmol), and tributylphosphine (0.05 mmol) were added and stirred at 140 °C. After 24 hours, citric acid solution was added for neutralization, followed by extraction three times with ethyl acetate. The organic phase was dehydrated with sodium sulfate, filtered, and concentrated to obtain a crude product. The crude product was purified by column chromatography (hexane:ethyl acetate) to obtain the target product Z164 (yield 5%).

[0647] Example 71 Synthesis of compound (Z166) [Chem.188]

[0648] Under a nitrogen atmosphere and in xylene, using 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine (2.0 mmol) and intermediate 10 (5.0 mmol), Z166 (35% yield) was obtained as the target product by the same synthesis method as in Example 70.

[0649] Example 72 Synthesis of compound (Z168) [Chemistry 189]

[0650] Z168 (6% yield) as the target product was obtained by using piperazine and intermediate 10 (5.0 mmol) in xylene under a nitrogen atmosphere, via the same synthesis method as in Example 70.

[0651] Example 73 Synthesis of compound (Z169) [Chemistry 190]

[0652] Under a nitrogen atmosphere and in xylene, using 1,2,3,4-tetrahydroquinoxaline and intermediate 10 (5.0 mmol), Z169 (yield 8%) was obtained as the target product by the same synthetic method as in Example 70.

[0653] Example 74 Synthesis of compound (Z170) [Chemistry 191]

[0654] Under a nitrogen atmosphere and in xylene, using 5,10-dihydrophenazine and intermediate 10 (5.0 mmol), Z170 (yield 3%) was obtained as the target product by the same synthesis method as in Example 70.

[0655] Example 75 Synthesis of compound (Z171) [Chemistry 192]

[0656] Under a nitrogen atmosphere and in THF, using 2,2′-(2,5-furandiyl)bis[4,4,5,5-tetramethyl-1,3,2-dioxaborane] (5.0 mmol) and intermediate 10 (12.0 mmol), Z171 (yield 34%), the target product, was obtained by the same synthesis method as in Example 39.

[0657] Example 76 Synthesis of compound (Z172) [Chemistry 193]

[0658] Under a nitrogen atmosphere and in THF, using 2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)-1H-pyrrole (5.0 mmol) and intermediate 20 (12.0 mmol), Z172 (yield 23%), the target product, was obtained by the same synthesis method as in Example 39.

[0659] Example 77 Synthesis of compound (Z173) [Chemistry 194]

[0660] Under a nitrogen atmosphere and in THF, using 2,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)-N-methylpyrrole (5.0 mmol) and intermediate 20 (12.0 mmol), Z173 (yield 35%), the target product, was obtained by the same synthesis method as in Example 39.

[0661] Example 78 Synthesis of compound (Z174) [Chemistry 195]

[0662] Under a nitrogen atmosphere and in THF, using 2,2′-(2,5-thiophenediyl)bis[4,4,5,5-tetramethyl-1,3,2-dioxaborane] (5.0 mmol) and intermediate 20 (12.0 mmol), Z174 (yield 21%), the target product, was obtained by the same synthesis method as in Example 39.

[0663] Synthesis Example 23: Synthesis of Intermediate 23 [Chemistry 196]

[0664] Under a nitrogen atmosphere and in THF, using 2-pentafluorothiobromoethane (6.0 mmol) and 6-bromo-9H-carbazole-3-ol (2.0.0 mmol), intermediate 23, the target product, was obtained by the same synthetic method as in Example 1.

[0665] Example 79 Synthesis of compound (Z200) [Chemistry 197]

[0666] Under a nitrogen atmosphere and in THF, using 1,4-phenyldiboronic acid bis(pinacol) ester (5.0 mmol) and intermediate 23, Z200 (yield 32%), the target product, was obtained by the same synthesis method as in Example 39.

[0667] Synthesis Example 24: Synthesis of Intermediate 24 [Chemistry 198]

[0668] Under a nitrogen atmosphere and in THF, using 2-pentafluorothiobromoethane (4.0 mmol) and 9H-carbazole-3,6-diol (2.00 mmol), intermediate 24 (yield 40%), which is the target product, was obtained by the same synthesis method as in Example 1.

[0669] Example 80 Synthesis of compound (Z202) [Chemistry 199]

[0670] Z202 (yield 12%), the target product, was obtained by the same synthesis method as in Example 70, using 1,4-dibromobenzene (1.0 mmol) and intermediate 24 (5.0 mmol) in xylene under a nitrogen atmosphere.

[0671] Example 81 Synthesis of compound (Z203) [Chemistry 200]

[0672] Under a nitrogen atmosphere and in xylene, using 4,4′-dibromobenzene (1.0 mmol) and intermediate 24 (5.0 mmol), Z203 (yield 20%), the target product, was obtained by the same synthesis method as in Example 70.

[0673] Example 82 Synthesis of compound (Z204) [Chemical Engineering 201]

[0674] Under a nitrogen atmosphere and in DMF, perfluorobiphenyl (1.0 mmol), intermediate 24 (3.0 mmol), and tripotassium phosphate (20 mmol) were added and stirred at 140 °C. After 24 hours, citric acid solution was added for neutralization, followed by extraction three times with ethyl acetate. The organic phase was dehydrated with sodium sulfate, filtered, and concentrated to obtain a crude product. The crude product was purified by column chromatography (hexane:ethyl acetate) to obtain the target product Z204 (yield 50%).

[0675] Example 83 Synthesis of compound (Z214) [Chemical Engineering 202]

[0676] Under a nitrogen atmosphere and in THF, using 2,2′-(2,7-phenanthrenediyl)bis[4,4,5,5-tetramethyl-1,3,2-dioxaborane] (5.0 mmol) and intermediate 8 (12.0 mmol), Z214 (yield 36%) was obtained as the target product by the same synthesis method as in Example 39.

[0677] Example 84 Synthesis of compound (Z215) [Chemical Engineering 203]

[0678] Under a nitrogen atmosphere and in THF, using 2,2′-(2,7-pyrenediyl)bis[4,4,5,5-tetramethyl-1,3,2-dioxaborane] (5.0 mmol) and intermediate 8 (12.0 mmol), Z215 (yield 42%), the target product, was obtained by the same synthesis method as in Example 39.

[0679] Example 85 Synthesis of compound (Z240) [Chemical 204]

[0680] Under a nitrogen atmosphere, 100 mL of THF was added to magnesium powder (1.0 mmol), followed by 10 mL of THF in bis(4-bromophenyl) ether (3.0 mmol) at room temperature. After stirring for 1 hour, a THF solution of intermediate 19 (8.0 mmol) was slowly added, and the mixture was stirred for another 3 hours. After the reaction was complete, 100 mL of water was added, and the mixture was stirred for 1 hour. The mixture was then extracted three times with ethyl acetate. The organic phase was dehydrated with sodium sulfate, filtered, and concentrated to obtain the crude product. The crude product was purified by column chromatography (hexane:ethyl acetate) to obtain Z240 (yield 21%) as the target product.

[0681] Example 86 Synthesis of compound (Z243) [Chemical Engineering 205]

[0682] Under a nitrogen atmosphere, using bis(4-bromophenyl) ether and intermediate 9 (8.0 mmol), Z243 (yield 18%) was obtained as the target product by the same synthesis method as in Example 85.

[0683] Example 87 Synthesis of compound (Z244) [Chemical Engineering 206]

[0684] Z244 (yield 26%), the target product, was obtained by the same synthesis method as in Example 37 using 1,3,5-cyclohexanetriol (3.0 mmol) and intermediate 9 (8.0 mmol).

[0685] Example 88 Synthesis of compound (Z251) [Chemical 207]

[0686] Under a nitrogen atmosphere, Z251 (yield 41%) was obtained as the target product using 1,4-bis(4-chlorophenyl)piperazine (3.0 mmol) and intermediate 9 (8.0 mmol) via the same synthesis method as in Example 85.

[0687] Example 89 Synthesis of compound (Z252) [Chemical Engineering 208]

[0688] Under a nitrogen atmosphere, Z252 (yield 36%) was obtained as the target product by the same synthesis method as in Example 39 using 1,3,5-tris(4,4,5,5-tetramethyl-1,3,2-dioxaborane-2-yl)benzene (3.0 mmol) and intermediate 9 (8.0 mmol).

[0689] Synthesis Example 25: Synthesis of Intermediate 25 [Chemical Engineering 209]

[0690] Z252 (90% yield) was obtained as the target product using the same synthesis method as in Example 22, with bis(4-bromophenyl)amine (3.0 mmol) and perfluoropyridine (8.0 mmol).

[0691] Example 90 Synthesis of compound (Z253) [Chemical 210]

[0692] Under a nitrogen atmosphere, using intermediates 25 (3.0 mmol) and 9 (8.0 mmol), Z253 (yield 22%) was obtained as the target product by the same synthesis method as in Example 85.

[0693] Example 91 Synthesis of compound (Z255) [Chemistry 211]

[0694] Under a nitrogen atmosphere, 1,3-bis(4-bromophenyl)tricyclic [3.3.1.1] was used. 3，7 ] Decane (3.0 mmol) and intermediate 9 (8.0 mmol) were synthesized using the same method as in Example 85 to obtain Z255 as the target product (yield 20%).

[0695] Example 92 Synthesis of compound (Z266) [Chemistry 212]

[0696] Under a nitrogen atmosphere, Z251 (yield 41%) was obtained as the target product by the same synthesis method as in Example 85 using 1,1′-thiobis[3-bromobenzene] (3.0 mmol) and intermediate 9 (8.0 mmol).

[0697] Example 93 Synthesis of compound (Z269) [Chemistry 213]

[0698] Under a nitrogen atmosphere, using B,B′-(oxydi-4,1-phenylene)bis[boronic acid] (3.0 mmol) and intermediate 16 (8.0 mmol), Z269 (yield 31%), the target product, was obtained by the same synthesis method as in Example 39.

[0699] Synthesis Example 26: Synthesis of Intermediate 26 [Chemistry 214]

[0700] Under a nitrogen atmosphere, using 4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaboran-2-yl)phenyl]aniline (3.0 mmol) and intermediate 16 (8.0 mmol), intermediate 26, as the target product, was obtained by the same synthetic method as in Example 39 (yield 33%).

[0701] Example 94 Synthesis of compound (Z272) [Chemical 215]

[0702] Z272 (yield 10%), the target product, was obtained by using 2-pentafluorothiobromoethane and intermediate 26 via the same synthesis method as in Example 1.

[0703] Example 95 Synthesis of compound (Z273) [Chemistry 216]

[0704] Under a nitrogen atmosphere, using bis(4-bromophenyl)-N-methylamine (3.0 mmol) and intermediate 20 (8.0 mmol), Z273 (50% yield) was obtained as the target product by the same synthesis method as in Example 11.

[0705] Synthesis Example 27: Synthesis of Intermediate 27 [Chemistry 217]

[0706] Under a nitrogen atmosphere, intermediate 9 (3.0 mmol) and methylamine (9.0 mmol) were stirred in acetonitrile for 2 hours, concentrated, and washed with water to obtain intermediate 27 of the target product (yield 90%).

[0707] Example 96 Synthesis of compound (Z274) [Chemistry 218]

[0708] Under a nitrogen atmosphere and in THF, intermediates 27 (8.0 mmol), 8.0 mmol, and potassium carbonate (8.0 mmol) were stirred at 70 °C for 5 hours. Citric acid solution was added for neutralization, followed by extraction three times with ethyl acetate. The organic phase was dehydrated with sodium sulfate, filtered, and concentrated to obtain the crude product. The crude product was purified by column chromatography (hexane:ethyl acetate) to obtain the target product Z274 (yield 40%).

[0709] Example 97 Synthesis of compound (Z275) [Chemistry 219]

[0710] Under a nitrogen atmosphere and in THF, using intermediates 27 (8.0 mmol) and 19 (8.0 mmol), Z275 (yield 41%) was obtained as the target product by the same synthesis method as in Example 96.

[0711] Example 97 Synthesis of compound (Z276) [Chem.220]

[0712] Under a nitrogen atmosphere, Z276 (yield 28%) was obtained as the target product using the same synthetic method as in Example 37, with 1,1′-(1,4-phenylene)bis[piperazine] (3.0 mmol) and intermediate 19 (8.0 mmol).

[0713] Example 98 Synthesis of compound (Z277) [Chemistry 221]

[0714] Under a nitrogen atmosphere, using bis(4-bromophenyl)-N-methylamine (3.0 mmol) and intermediate 8 (8.0 mmol), Z277 (35% yield) was obtained as the target product by the same synthesis method as in Example 11.

[0715] Example 99 Synthesis of compound (Z278) [Chemistry 222]

[0716] Under a nitrogen atmosphere, using bis(4-bromophenyl) sulfide (3.0 mmol) and intermediate 8 (8.0 mmol), Z278 (yield 34%) was obtained as the target product by the same synthesis method as in Example 11.

[0717] Example 100 Synthesis of compound (Z279) [Chemistry 223]

[0718] Under a nitrogen atmosphere, Z279 (yield 34%) was obtained as the target product by the same synthesis method as in Example 11 using 1,1′,1′′,1′′′-silyltetra[4-bromobenzene] (3.0 mmol) and intermediate 8 (8.0 mmol).

[0719] Example 101 Synthesis of compound (Z281) [Chemistry 224]

[0720] Under a nitrogen atmosphere, using 6-bromo-N-(6-bromo-2-pyridyl)-N-methyl-2-pyridylamine (3.0 mmol) and intermediate 20 (8.0 mmol), Z281 (yield 34%), the target product, was obtained by the same synthesis method as in Example 11.

[0721] Example 102 Synthesis of compound (Z287) [Chemistry 225]

[0722] Under a nitrogen atmosphere, using lithium amino (1.0 mmol) and intermediate 16 (8.0 mmol), Z287 (yield 3%) was obtained as the target product by the same synthesis method as in Example 70.

[0723] Example 103 Synthesis of compound (Z289) [Chemistry 226]

[0724] Under a nitrogen atmosphere, using 1,3-bis(methylamino)propane (1.0 mmol) and intermediate 20 (4.0 mmol), Z289 (yield 15%) was obtained as the target product by the same synthesis method as in Synthesis Example 21.

[0725] Example 104 Synthesis of compound (Z304) [Chemistry 227]

[0726] Under a nitrogen atmosphere, Z304 (yield 21%) was obtained as the target product by the same synthesis method as in Example 37, using 1,2-ethylenedithiol (1.0 mmol) and intermediate 9 (3.0 mmol).

[0727] Example 105 Synthesis of compound (Z307) [Chemistry 228]

[0728] Under a nitrogen atmosphere, using 1,2-bis(phenylamino)ethane (3.0 mmol) and intermediate 9 (7.0 mmol), Z304 (yield 21%) was obtained as the target product by the same synthesis method as in Synthesis Example 21.

[0729] Example 106 Synthesis of Z345 [Chemistry 229]

[0730] Under a nitrogen atmosphere, 1,2-ethylenediamine (5.0 mmol), perfluoropyridine (21.0 mmol), and potassium carbonate were heated in THF for 4 hours. Then, Z345 (yield 12%) was obtained by purification with 2-pentafluorothioethanol (50.0 mmol) using the same method as in Example 1.

[0731] Example 107 Synthesis of Z347 [Chemistry 230]

[0732] Under a nitrogen atmosphere, 1,2-ethylenediamine (5.0 mmol), perfluoropyridine (21.0 mmol), and potassium carbonate were heated in THF for 4 hours. Then, Z347 (8% yield) was obtained by purification using the same method as in Example 1, with 3-pentafluorothioethanol (50.0 mmol).

[0733] (Evaluation of the metal adhesion of the compounds described in the examples) The glass substrate was subjected to boiling cleaning with isopropanol, followed by further ultraviolet ozone cleaning, and then placed in a vacuum evaporation apparatus. The vacuum pump was used to exhaust the gas until a pressure of 1.0 × 10⁻⁶ was reached. -4 Pa or less. On a glass substrate with a metal mask having an opening of 20 mm × 10 mm, the compounds described in Tables 1 to 3 were deposited to a film of 100 nm at a deposition rate of 0.2 nm / s. Then, the metal mask was removed, and ytterbium was deposited to a film of 2 nm at a deposition rate of 0.01 nm / s, followed by silver to a film of 20 nm at a deposition rate of 0.1 nm / s. The presence or absence of the 20 mm × 10 mm transparent region is shown in Tables 1 to 3.

[0734] (Transmittance Measurement) Metal adhesion can be evaluated by measuring light transmittance; if metal adheres, light transmittance decreases. Furthermore, if the amount of metal adhered increases, light transmittance also decreases accordingly.

[0735] (Transmittance determination of the compounds described in the examples) The glass substrate was subjected to boiling cleaning (using isopropanol), followed by ultraviolet ozone cleaning, and then placed in a vacuum evaporation apparatus. The vacuum pump was used to exhaust the gas to 1.0 × 10⁻⁶. -4 Below Pa. First, on a glass substrate, a 15 nm layer of 2,4,6-tris([1,1′-biphenyl]-4-yl)-1,3,5-triazine was deposited at a vapor deposition rate of 0.1 nm / s as a base layer. Next, a metal mask with an opening of 2 mm × 1 mm was configured, and the compound described in the table was deposited at a vapor deposition rate of 0.1 nm / s as a metal patterning layer for 15 nm. Then, the metal mask was removed, and ytterbium and lithium fluoride (1 / 1) were deposited at a vapor deposition rate of 0.01 nm / s for 2 nm, and then silver and magnesium (1 / 1) were deposited at a vapor deposition rate of 0.1 nm / s for 20 nm. Finally, [1,1′-biphenyl]-4,4′-diamine and N4,N4′-biphenyl-N4,N4′-bis(9-phenyl-9H-carbazole-3-yl)- were deposited as a 100 nm cover layer at a deposition rate of 0.1 nm / s to fabricate patterned test elements. These are shown in Tables 1 to 3. For example, the results of Example 102, with a transmittance of 90% or higher, are shown below. Figure 1 .

[0736] (Evaluation of the adhesion between the compounds described in the examples and the CVD membrane) The glass substrate was subjected to boiling cleaning with isopropanol, followed by further ultraviolet ozone cleaning, and then placed in a vacuum evaporation apparatus. The vacuum pump was used to exhaust the gas until a pressure of 1.0 × 10⁻⁶ was reached. -4 Pa below. On a glass substrate with a metal mask having an opening of 20 mm × 10 mm, the compounds listed in Tables 1 to 3 were deposited to a film of 100 nm at a deposition rate of 0.2 nm / s. Then, the metal mask was removed, and ytterbium was deposited to a film of 2 nm at a deposition rate of 0.01 nm / s, followed by silver to a film of 20 nm at a deposition rate of 0.1 nm / s. CVD deposition (SiN) was then performed at 11 Ω / sec, and after 1 day, it was confirmed whether there was any peeling on the areas where the compounds were deposited. The results are shown in Tables 1 to 3.

[0737] [Table 1]

[0738] [Table 2]

[0739] [Table 3]

[0740] (Refer to Example 1: Evaluation of metal adhesion and measurement of light transmittance when no metal patterning material is used) Reference Example 1: Transmittance Measurement of Components with Unfilmed Metal Patterned Layers Without using a metal patterning layer (unfilmed), the patterned test element was fabricated using the same method as in the embodiments described above. The results of the transmittance measurement are shown below. Figure 2 The light transmittance is "≥20%", forming a metallic film.

[0741] Evaluation of metal adhesion and transmittance determination of comparative compound The following compounds (X1), (X2), (X3), (X4), (X5), and (X6) were used as metal patterning materials to evaluate metal adhesion and measure light transmittance.

[0742] Comparative compound (X1) [Chemistry 231]

[0743] Evaluation of metal adhesion and determination of transmittance of comparative compound (X1) Patterned test elements were fabricated in the metal patterned layer using compound (X1) through the same method as in the examples. The transmittance of a 2 mm × 1 mm portion of the compound (X1) film is shown below. Figure 3A light transmittance of "≥20%" cannot suppress the formation of a metal film.

[0744] Comparative compound (X2) [Chemistry 232]

[0745] Patterned test elements were fabricated in the metal patterned layer using compound (X2) via the same method as in the examples. The transmittance of a 2 mm × 1 mm portion of the compound (X2) film is shown below. Figure 4 A light transmittance of "≥60%" cannot suppress the formation of a metal film.

[0746] The following (X3), (X4), and (X5) were also measured using the same procedure to evaluate metal adhesion and transmittance. The results are shown in Table 4.

[0747] Comparative compound (X3) [Chemistry 233]

[0748] Comparative compound (X4) [Chemistry 234]

[0749] Comparative compound (X5) [Chemistry 235]

[0750] Comparative compound (X6) [Chemistry 236]

[0751] (Evaluation of metal adhesion of comparative example compounds) The glass substrate was subjected to boiling cleaning with isopropanol, followed by further ultraviolet ozone cleaning, and then placed in a vacuum evaporation apparatus. The vacuum pump was used to exhaust the gas until a pressure of 1.0 × 10⁻⁶ was reached. -4 Pa or less. On a glass substrate with a metal mask having an opening of 20 mm × 10 mm, the compounds described in Table 4 were deposited to a film of 100 nm at a deposition rate of 0.2 nm / s. Then, the metal mask was removed, and ytterbium was deposited to a film of 2 nm at a deposition rate of 0.01 nm / s, followed by silver to a film of 20 nm at a deposition rate of 0.1 nm / s. The presence or absence of the 20 mm × 10 mm transparent region is shown in Table 4.

[0752] (Evaluation of the adhesion between the comparative example compounds and the CVD membrane) The glass substrate was subjected to boiling cleaning with isopropanol, followed by further ultraviolet ozone cleaning, and then placed in a vacuum evaporation apparatus. The vacuum pump was used to exhaust the gas until a pressure of 1.0 × 10⁻⁶ was reached. -4 Pa below. On a glass substrate with a metal mask having an opening of 20 mm × 10 mm, the compound described in Table 4 was deposited to a film of 100 nm at a deposition rate of 0.2 nm / s. Then, the metal mask was removed, and ytterbium was deposited to a film of 2 nm at a deposition rate of 0.01 nm / s, followed by silver to a film of 20 nm at a deposition rate of 0.1 nm / s. CVD deposition (SiN) was then performed at 11 Ω / sec, and after 1 day, it was confirmed whether there was any peeling on the areas where the compound was deposited. The results are shown in Table 4.

[0753] [Table 4]

[0754] Although this disclosure 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.

[0755] It should be noted that the entire contents of the specification, claims, drawings and abstract of Japanese Patent Application No. 2023-192953, filed on November 13, 2023, are incorporated herein as a disclosure of the specification of this invention.

Claims

1. A patterned metallic material, characterized in that, It includes compounds represented by the following formula (101), In the aforementioned formula (101), Y 101 Each of these groups independently represents an aromatic hydrocarbon group with 6 to 26 monocyclic, intercyclic, or fused carbon atoms, whether substituted or unsubstituted; a heteroaromatic hydrocarbon group with 3 to 26 monocyclic, intercyclic, or fused carbon atoms, whether substituted or unsubstituted; a cyclic aliphatic hydrocarbon group with 3 to 8 carbon atoms, whether substituted or unsubstituted; or a heteroaliphatic hydrocarbon group with 3 to 26 monocyclic, intercyclic, or fused carbon atoms, whether substituted or unsubstituted. X 101 Each independently represents a cyclic aliphatic hydrocarbon group with 3 to 8 carbon atoms, either substituted or unsubstituted; a heteroaliphatic hydrocarbon group with 3 to 26 carbon atoms, whether monocyclic, cyclic, or fused; O; OR 101 ;S;SR 101 ;N(R 101 )2; or Si(R) 101 ) f 101 , R 101 Aromatic hydrocarbon groups of 6–26 monocyclic, bicyclic, or fused rings, bonded to oxygen, sulfur, or nitrogen atoms, each independently representing a monocyclic, bicyclic, or fused ring aromatic hydrocarbon group of 3–26 monocyclic, bicyclic, or fused rings; a straight-chain, branched, or cyclic aliphatic hydrocarbon group of 1–18 monocyclic, bicyclic, or cyclic rings; a monocyclic, bicyclic, or fused ring aliphatic hydrocarbon group of 3–26 monocyclic, bicyclic, or fused rings; a hydrogen atom; or formula (111). Rs 101 Each of them independently represents the group shown in the following formula (111). a 101 Each can independently represent an integer from 1 to 6. b 101 Each can independently represent an integer from 0 to 8. c 101 Each can independently represent an integer from 0 to 8. e 101 Each can independently represent an integer from 1 to 8. f 101 Each can independently represent an integer from 0 to 3. In the aforementioned formula (111), L 111 Each of these groups independently represents a straight-chain, branched, or cyclic aliphatic hydrocarbon group with 1 to 18 carbon atoms, whether substituted or unsubstituted; a straight-chain, branched, or cyclic alkenyl group with 1 to 18 carbon atoms, whether substituted or unsubstituted; or a straight-chain, branched, or cyclic ethynyl group with 1 to 18 carbon atoms, whether substituted or unsubstituted. X 111 Each can be independently represented as O, S, NH, or NR. 101 , R 101 Bonded to a nitrogen atom, each independently representing a monocyclic, bicyclic, or fused-ring aromatic hydrocarbon group with 6 to 26 carbon atoms, whether substituted or unsubstituted; a monocyclic, bicyclic, or fused-ring heteroaromatic hydrocarbon group with 3 to 26 carbon atoms, whether substituted or unsubstituted; a straight-chain, branched, or cyclic aliphatic hydrocarbon group with 1 to 18 carbon atoms, whether substituted or unsubstituted; a monocyclic, bicyclic, or fused-ring heteroaliphatic hydrocarbon group with 3 to 26 carbon atoms, whether substituted or unsubstituted; a hydrogen atom; or the formula (111) stated above. Indicates the bonding location, a 111 Each can independently represent an integer from 1 to 6. b 111 Each can independently represent an integer from 1 to 18. c 111 Each can independently represent an integer from 1 to 2. d 111 Each can independently represent an integer from 0 to 1.

2. The patterned metal material according to claim 1, wherein, In the aforementioned formula (101), Y 101 The aromatic hydrocarbon group shown has a phenyl group, or a structure formed by connecting or fused multiple benzene rings. Y 101 The heteroatoms in the heteroaromatic hydrocarbon group shown are N, O, or S, and the heteroaromatic hydrocarbon group has a 5-membered ring, a 6-membered ring, or a structure formed by their fusion. Y 101 The heteroatoms in the cyclic heteroaliphatic hydrocarbon group shown are N, O or S, and the cyclic heteroaliphatic hydrocarbon group has a 5-membered ring, a 6-membered ring, a 7-membered ring, an 8-membered ring, or a structure formed by their fusion.

3. The patterned metal material according to claim 1, wherein, In the aforementioned formula (101), Provide Y 101 The aromatic hydrocarbon compounds shown are, independently, benzene, biphenyl, terphenyl, naphthalene, fluorene, spirodifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzo[a]fluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, β-, perylene, benzo[a]pyrene, triphenylene, dibenzo[a]pyrene, or compounds formed by fused together with one or more of benzene, naphthalene, and phenanthrene. Provide Y 101 The heteroaromatic hydrocarbon compounds shown are, independently, pyridine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thiaanthracene, acridine, dihydroacridine, phenoxazine, phenthiazine, dibenzo-1,4-dioxin, 5,6,7,8-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, or compounds formed by fused to these compounds with one or more selected from benzene, naphthalene, and phenanthrene. Provide Y 101 The cyclic aliphatic hydrocarbon compounds shown are each independently adamantane, diadamantane, cyclopentane, cyclohexane, cycloheptane, or cyclooctane. Provide Y 101 The cyclic heteroaliphatic hydrocarbon compounds shown are each independently morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiaane, 4,4′-bipiperidine, diazabicyclo[2,2,2]octane, and octahydro-1H-pyrrolo[3,4-b]pyridine, or 1,4,7,10-tetraazacyclododecane.

4. The patterned metal material according to claim 1, wherein, In the aforementioned formula (101), Y 101 The substituents are each independently: Methyl, methoxy, trifluoromethoxy, alkyl with 2-10 carbon atoms, cyano, deuterium, fluorine, chlorine, bromine, iodine, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, indoleyl, carbazoleyl, benzothiopheneyl, dibenzothiopheneyl, benzofuranyl, dibenzofuranyl, thiazolyl, benzothiazolyl, the structure shown in formula (111), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

5. The patterned metal material according to claim 1, wherein, In the above formula (101), X 101 The heteroatoms in the cyclic heteroaliphatic hydrocarbon group shown are N, O or S, and the cyclic heteroaliphatic hydrocarbon group has a 5-membered ring, a 6-membered ring, a 7-membered ring, an 8-membered ring or a structure formed by their fusion.

6. The patterned metal material according to claim 1, wherein, In the aforementioned formula (101), Provide X 101 The cyclic aliphatic hydrocarbon compounds shown are each independently adamantane, diadamantane, norbornene, cyclopentane, cyclohexane, cycloheptane, or cyclooctane. Provide X 101 The cyclic heteroaliphatic hydrocarbon compounds shown are each independently morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiaane, 4,4′-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, or 1,4,7,10-tetraazacyclododecane.

7. The patterned metal material according to claim 1, wherein, In the above formula (101), X 101 The substituents are each independently: Methyl, methoxy, trifluoromethoxy, alkyl with 2-10 carbon atoms, cyano, deuterium, fluorine, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, indoleyl, carbazoleyl, benzothiopheneyl, dibenzothiopheneyl, benzofuranyl, dibenzofuranyl, thiazolyl, benzothiazolyl, the structure shown in formula (111), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

8. The patterned metal material according to claim 1, wherein, In the aforementioned formula (111), R 101 The aromatic hydrocarbon group shown has a phenyl group, or a structure formed by connecting or fused multiple benzene rings. R 101 The heteroatoms in the heteroaromatic hydrocarbon group shown are N, O, or S, and the heteroaromatic hydrocarbon group has a 5-membered ring, a 6-membered ring, or a structure formed by their fusion. R 101 The heteroatoms in the heteroaliphatic hydrocarbon group shown are N, O or S, and the heteroaliphatic hydrocarbon group has a 5-membered ring, a 6-membered ring, a 7-membered ring, an 8-membered ring, or a structure formed by their fusion.

9. The patterned metal material according to claim 1, wherein, In the aforementioned formula (111), Provide R 101 The aromatic hydrocarbon compounds shown are, independently, benzene, biphenyl, terphenyl, naphthalene, fluorene, spirodifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzo[a]fluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, β-, perylene, benzo[a]pyrene, triphenylene, dibenzo[a]pyrene, or compounds formed by fused together with one or more of benzene, naphthalene, and phenanthrene. Provide R 101 The heteroaromatic hydrocarbon compounds shown are, independently, pyridine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thiaanthracene, acridine, dihydroacridine, phenoxazine, phenthiazine, dibenzo-1,4-dioxin, 5,6,7,8-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, or compounds formed by fused to these compounds with one or more selected from benzene, naphthalene, and phenanthrene. R 101 The aliphatic hydrocarbon groups shown are each independently: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptyl, octadecyl, nonadecanyl, carbazolyl, adamantyl, diadamantyl, cyclohexyl, or structures formed by further substitution of these groups with one or more groups selected from these groups. Provide R 101 The cyclic heteroaliphatic hydrocarbon compounds shown are each independently morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiaane, 4,4′-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, or 1,4,7,10-tetraazacyclododecane.

10. The patterned metal material according to claim 1, wherein, In the aforementioned equation (111), R 101 The substituents are each independently: Methyl, methoxy, trifluoromethyl, trifluoromethoxy, alkyl with 2-10 carbon atoms, cyano, deuterium, fluorine, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, indoleyl, carbazoleyl, benzothiopheneyl, dibenzothiopheneyl, benzofuranyl, dibenzofuranyl, thiazolyl, benzothiazolyl, the structure shown in formula (111), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

11. The patterned metal material according to claim 1, wherein, In the aforementioned formula (111), L 111 The aliphatic hydrocarbon groups shown are each independently: methyl, ethyl, propane, butane, pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, heptane, octadecane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, or cyclooctane, or groups that have a structural isomeric relationship with these groups. L 111 The alkenyl groups shown are each independently vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptenyl, octadecenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, or cyclooctenyl, or groups that have structural isomerism with these groups. L 111 The acetylenyl group shown is acetylenyl, propynyl, butynyl, pentynyl, hexynyl, hepynyl, octylenyl, nonynyl, decynyl, undecynyl, dodeynyl, tridecynyl, tetradecynyl, decadecynyl, hexadecynyl, heptadecynyl, or octadecynyl, or a group that has a structural isomerism relationship with these groups.

12. The patterned metal material according to claim 1, wherein, In the above formula (111), L 111 The substituents are each independently: Methyl, methoxy, trifluoromethoxy, alkyl groups with 2 to 10 carbon atoms, deuterium, chlorine, bromine, iodine, or The structure is formed by further substituting these groups with one or more groups selected from these groups.

13. The compound represented by the following formula (501), In the aforementioned formula (501), Y 501 This refers to an aromatic hydrocarbon group with 6 to 26 monocyclic, intercyclic, or fused carbon atoms, whether substituted or not; a heteroaromatic hydrocarbon group with 3 to 26 monocyclic, intercyclic, or fused carbon atoms, whether substituted or not; a cyclic aliphatic hydrocarbon group with 3 to 8 carbon atoms, whether substituted or not; or a heteroaliphatic hydrocarbon group with 3 to 26 monocyclic, intercyclic, or fused carbon atoms, whether substituted or not. X 501 Represents a cyclic aliphatic hydrocarbon group with 3 to 8 carbon atoms, whether substituted or not; a heteroaliphatic hydrocarbon group with 3 to 26 carbon atoms, whether monocyclic, cyclic, or fused; O; OR 501 ;S;SR 501 ;N(R 501 )2; or Si(R) 501 ) f 501 , R 501 Aromatic hydrocarbon groups of 6 to 26 carbon atoms, either monocyclic, cyclic, or fused, bonded to oxygen, sulfur, or nitrogen atoms, each independently representing a monocyclic, cyclic, or fused-ring aromatic hydrocarbon group of 3 to 26 carbon atoms, either monocyclic, cyclic, or fused-ring; a straight-chain, branched, or cyclic aliphatic hydrocarbon group of 1 to 18 carbon atoms, either monocyclic, cyclic, or fused-ring; a hydrogen atom; or the following formula (555). Rs 501 Each of the groups represented independently by formula (555) a 501 Each can independently represent an integer from 1 to 6. b 501 Each can independently represent an integer from 0 to 8. c 501 Each can independently represent an integer from 0 to 8. e 501 Each can independently represent an integer from 1 to 8. f 501 Each can independently represent an integer from 0 to 3. In the aforementioned formula (555), L 555 Each of these groups independently represents a straight-chain, branched, or cyclic aliphatic hydrocarbon group with 1 to 18 carbon atoms, whether substituted or unsubstituted; a straight-chain, branched, or cyclic alkenyl group with 1 to 18 carbon atoms, whether substituted or unsubstituted; or a straight-chain, branched, or cyclic ethynyl group with 1 to 18 carbon atoms, whether substituted or unsubstituted. X 555 Each can be independently represented as O, S, NH, or NR. 501 , R 501 Aromatic hydrocarbon groups of 6 to 26 carbon atoms, bonded to nitrogen, oxygen, sulfur, or silicon atoms, each independently representing a monocyclic, intercyclic, or fused ring aromatic hydrocarbon group of 3 to 26 carbon atoms, with or without substitution; a straight-chain, branched, or cyclic aliphatic hydrocarbon group of 1 to 18 carbon atoms, with or without substitution; a monocyclic, intercyclic, or fused ring aliphatic hydrocarbon group of 3 to 26 carbon atoms, with or without substitution; a hydrogen atom; or the formula (555) stated above. Indicates the bonding location, a 555 Each can independently represent an integer from 1 to 6. b 555 Each can independently represent an integer from 1 to 18. c 555 Each can independently represent an integer from 1 to 2. d 555 Each can independently represent an integer from 0 to 1. in, The compound represented by formula (501) has two or more structures of formula (555) within the molecule, or has one or more fluorine atoms in addition to formula (555) within the molecule.

14. The compound according to claim 13, wherein, In the aforementioned formula (501), Y 501 The aromatic hydrocarbon group shown has a phenyl group, or a structure formed by connecting or fused multiple benzene rings. Y 501 The heteroatoms in the heteroaromatic hydrocarbon group shown are N, O, or S, and the heteroaromatic hydrocarbon group has a 5-membered ring, a 6-membered ring, or a structure formed by their fusion. Y 501 The heteroatoms in the heteroaliphatic hydrocarbon group shown are N, O or S, and the heteroaliphatic hydrocarbon group has a 5-membered ring, a 6-membered ring, a 7-membered ring or a structure formed by their fusion.

15. The compound according to claim 13, wherein, In the aforementioned formula (501), Provide Y 501 The aromatic hydrocarbon compounds shown are, independently, benzene, biphenyl, terphenyl, naphthalene, fluorene, spirodifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzo[a]fluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, β-, perylene, benzo[a]pyrene, triphenylene, dibenzo[a]pyrene, or compounds formed by fused together with one or more of benzene, naphthalene, and phenanthrene. Provide Y 501 The heteroaromatic hydrocarbon compounds shown are, independently, pyridine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thiaanthracene, acridine, dihydroacridine, phenoxazine, phenthiazine, dibenzo-1,4-dioxin, 5,6,7,8-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, or compounds formed by fused to these compounds with one or more selected from benzene, naphthalene, and phenanthrene. Provide Y 501 The cyclic aliphatic hydrocarbon compounds shown are each independently adamantane, diadamantane, cyclopentane, cyclohexane, cycloheptane, or cyclooctane. Provide Y 501 The cyclic heteroaliphatic hydrocarbon compounds shown are each independently morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiaane, 4,4′-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, or 1,4,7,10-tetraazacyclododecane.

16. The compound according to claim 13, wherein, In the aforementioned formula (501), Y 501 The substituents are each independently: Methyl, methoxy, trifluoromethoxy, alkyl with 2-10 carbon atoms, cyano, deuterium, fluorine, chlorine, bromine, iodine, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazineyl, indoleyl, carbazoleyl, benzothiopheneyl, dibenzothiopheneyl, benzofuranyl, dibenzofuranyl, thiazolyl, benzothiazolyl, structures shown in formula (555), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

17. The compound according to claim 13, wherein, In the aforementioned formula (501), X 501 The heteroatoms in the cyclic heteroaliphatic hydrocarbon groups with 3 to 18 carbon atoms shown are N, O, or S, and the cyclic heteroaliphatic hydrocarbon groups have 5-membered rings, 6-membered rings, 7-membered rings, 8-membered rings, or structures formed by their fusion.

18. The compound according to claim 13, wherein, In the aforementioned formula (501), Provide X 501 The cyclic aliphatic hydrocarbon compounds shown are each independently adamantane, diadamantane, norbornene, cyclopentane, cyclohexane, cycloheptane, or cyclooctane. Provide X 501 The cyclic heteroaliphatic hydrocarbon compounds shown are each independently morpholine, piperazine, homopiperazine, hexahydro-1,3,5-triazine, 1,4-dioxin, 1,4-dithiaane, 4,4′-bipiperidine, diazabicyclo[2,2,2]octane, octahydro-1H-pyrrolo[3,4-b]pyridine, or 1,4,7,10-tetraazacyclododecane.

19. The compound according to claim 13, wherein, In the aforementioned formula (501), X 501 The substituents are each independently: Methyl, methoxy, trifluoromethoxy, alkyl with 2-10 carbon atoms, cyano, deuterium, fluorine, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, indoleyl, carbazoleyl, benzothiopheneyl, dibenzothiopheneyl, benzofuranyl, dibenzofuranyl, thiazolyl, benzothiazolyl, the structure shown in formula (555), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

20. The compound according to claim 13, wherein, In the aforementioned formula (501), R 501 The aromatic hydrocarbon group shown has a phenyl group, or a structure formed by connecting or fused multiple benzene rings. R 501 The heteroatoms in the heteroaromatic hydrocarbon group shown are N, O, or S, and the heteroaromatic hydrocarbon group has a 5-membered ring, a 6-membered ring, or a structure formed by their fusion. R 501 The heteroatoms in the cyclic heteroaliphatic hydrocarbon group shown are N, O or S, and the cyclic heteroaliphatic hydrocarbon group has a 5-membered ring, a 6-membered ring, a 7-membered ring, an 8-membered ring, or a structure formed by their fusion.

21. The compound according to claim 13, wherein, In the aforementioned formula (501), Provide R 501 The aromatic hydrocarbon compounds shown are, independently, benzene, biphenyl, terphenyl, naphthalene, fluorene, spirodifluorene, 9,9-dimethylfluorene, 9,9-diphenylfluorene, benzo[a]fluorene, phenanthrene, fluoranthene, triphenylene, anthracene, pyrene, β-, perylene, benzo[a]pyrene, triphenylene, dibenzo[a]pyrene, or compounds formed by fused together with one or more of benzene, naphthalene, and phenanthrene. Provide R 501 The heteroaromatic hydrocarbon compounds shown are, independently, pyridine, pyrazine, triazine, carbazole, furan, thiophene, benzofuran, benzothiophene, benzodioxin, dibenzofuran, dibenzothiophene, thiazole, thiadiazole, thiaanthracene, acridine, dihydroacridine, phenoxazine, phenthiazine, dibenzo-1,4-dioxin, 5,6,7,8-tetrahydroquinoxaline, 2,3,4,5-tetrahydro-1H-1,4-benzodiazepine, 2,3,4,5-tetrahydro-1H-1,5-benzodiazepine, benzothiazole, or compounds formed by fused to these compounds with one or more selected from benzene, naphthalene, and phenanthrene. R 501 The aliphatic hydrocarbon groups shown are each individually: methyl, ethyl, propyl, isopropyl, butyl, isobutyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptyl, octadecyl, nonadecanyl, carbazolyl, adamantyl, diadamantyl, cyclohexyl, or structures formed by further substituting these groups with one or more groups selected from these groups. Provide R 501 The cyclic heteroaliphatic hydrocarbon compounds shown are, 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.

22. The compound according to claim 13, wherein, In the aforementioned formula (501), R 501 The substituents are each independently: Methyl, methoxy, trifluoromethyl, trifluoromethoxy, alkyl with 2-10 carbon atoms, cyano, deuterium, fluorine, phenyl, biphenyl, naphthyl, phenanthryl, pyridyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, carbazoleyl, benzothiopheneyl, dibenzothiopheneyl, benzofuranyl, dibenzofuranyl, thiazolyl, benzothiazolyl, the structure shown in formula (555), or The structure is formed by further substituting these groups with one or more groups selected from these groups.

23. The compound according to claim 13, wherein, In the aforementioned formula (501), L 555 The aliphatic hydrocarbon groups shown are: methylene, ethane, propane, butane, pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, heptane, octadecane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, or groups that have structural isomerism with these groups. L 555 The alkenyl groups shown are vinyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptenyl, octadecenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, or groups that have structural isomerism with these groups. L 555 The acetylenyl group shown is acetylenyl, propynyl, butynyl, pentynyl, hexynyl, hepynyl, octylenyl, nonynyl, decynyl, undecynyl, dodeynyl, tridecynyl, tetradecynyl, pentadecynyl, hexadecynyl, heptadecynyl, octadecynyl, or a group that has a structural isomerism relationship with these groups.

24. The compound according to claim 13, wherein, The compound represented by formula (501) is a compound represented by formula (511), (531) or (541) below. In equations (511), (531), or (541), Y 501 X 501 Rs 501 a 501 b 501 c 501 d 501 e 501 Synonymous with the definition described in claim 13, n in formula (531) 501 Represents integers from 1 to 12.

25. The compound according to claim 13, wherein, The compound represented by formula (501) is the compound represented by formula (512) below. In the above formula (512), Rs 501 a 501 b 501 c 501 d 501 e 501 Synonymous with the definition set forth in claim 13, m 501 Each of the integers from 1 to 6 can be represented independently, Y 501 Let A′ represent each of the following equations (4-1) to (4-8) independently. Indicates a bonding bond. In equations (4-1) to (4-8), R 401 ~R 410 Each is independently represented by the following groups: hydrogen atom; deuterium atom; fluorine atom; bromine atom; chlorine atom; a straight-chain, branched, or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms, substituted or not substituted with fluorine atom; a straight-chain, branched, or cyclic alkoxy group having 1 to 20 carbon atoms, substituted or not substituted with fluorine atom; a cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms, monocyclic, bicyclic, or fused rings; an aromatic hydrocarbon group having 6 to 25 carbon atoms, monocyclic, bicyclic, or fused rings; a heteroaromatic group having 3 to 25 carbon atoms, monocyclic, bicyclic, or fused rings; or the formula (555).

26. The compound according to claim 13, wherein, The compound represented by formula (501) is the compound represented by formula (532) below. In the aforementioned formula (532), Y 501 X 501 Rs 501 R 501 a 501 b 501 c 501 e 501 f 501 Synonymous with the definition described in claim 13, m 501 Each of the integers 1 to 6 can be represented independently, and each of A′ can be represented independently as any one of the equations (4-1) to (4-8). Indicates a bonding bond. In equations (4-1) to (4-8), R 401 ~R 410 Each is independently represented by the following groups: hydrogen atom; deuterium atom; fluorine atom; bromine atom; chlorine atom; a straight-chain, branched, or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms, substituted or not substituted with fluorine atom; a straight-chain, branched, or cyclic alkoxy group having 1 to 20 carbon atoms, substituted or not substituted with fluorine atom; a cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms, monocyclic, bicyclic, or fused rings; an aromatic hydrocarbon group having 6 to 25 carbon atoms, monocyclic, bicyclic, or fused rings; a heteroaromatic group having 3 to 25 carbon atoms, monocyclic, bicyclic, or fused rings; or the formula (555).

27. The compound according to claim 13, wherein, The compound represented by formula (501) is a compound represented by formula (533), (534), (535) or (536) below. In the formula, Y 501 Rs 501 R 501 a 501 b 501 e 501 Synonymous with the definition set forth in claim 13, m 501 Each of the integers 1 to 6 can be represented independently, and each of A′ can be represented independently as any one of the equations (4-1) to (4-8). Indicates a bonding bond. In equations (4-1) to (4-8), R 401 ~R 410 Each is independently represented by the following groups: hydrogen atom; deuterium atom; fluorine atom; bromine atom; chlorine atom; a straight-chain, branched, or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms, substituted or not substituted with fluorine atom; a straight-chain, branched, or cyclic alkoxy group having 1 to 20 carbon atoms, substituted or not substituted with fluorine atom; a cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms, monocyclic, bicyclic, or fused rings; an aromatic hydrocarbon group having 6 to 25 carbon atoms, monocyclic, bicyclic, or fused rings; a heteroaromatic group having 3 to 25 carbon atoms, monocyclic, bicyclic, or fused rings; or the formula (555).

28. The compound according to claim 13, wherein, The compound represented by formula (501) is the compound represented by formula (542) below. In the formula, Rs 501 R 501 a 501 e 501 f 501 Synonymous with the definition set forth in claim 13, n 501 m represents integers from 1 to 12. 501 Each of the integers 1 to 6 can be represented independently, and each of A′ can be represented independently as any one of the equations (4-1) to (4-8). Representing a bond, C′ is composed of O, NH, N (R 501 )f 501 , S, Si(R 501 )f 501 express, In equations (4-1) to (4-8), R 401 ~R 410 Each is independently represented by the following groups: hydrogen atom; deuterium atom; fluorine atom; bromine atom; chlorine atom; a straight-chain, branched, or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms, substituted or not substituted with fluorine atom; a straight-chain, branched, or cyclic alkoxy group having 1 to 20 carbon atoms, substituted or not substituted with fluorine atom; a cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms, monocyclic, bicyclic, or fused rings; an aromatic hydrocarbon group having 6 to 25 carbon atoms, monocyclic, bicyclic, or fused rings; a heteroaromatic group having 3 to 25 carbon atoms, monocyclic, bicyclic, or fused rings; or the formula (555).

29. The compound according to claim 13, wherein, The compound represented by formula (501) is the compound represented by formula (543) below. In the aforementioned equation (543), Rs 501 a 501 e 501 Synonymous with the definition set forth in claim 13, n 501 m represents integers from 1 to 12. 501 Each of the integers 1 to 6 can be represented independently, and each of A′ can be represented independently as any one of the equations (4-1) to (4-8). Representing a bond, C′ is composed of O, NH, N (R 501 )f 501 , S, Si(R 501 )f 501 express, In equations (4-1) to (4-8), R 401 ~R 410 Each is independently represented by the following groups: hydrogen atom; deuterium atom; fluorine atom; bromine atom; chlorine atom; a straight-chain, branched, or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms, substituted or not substituted with fluorine atom; a straight-chain, branched, or cyclic alkoxy group having 1 to 20 carbon atoms, substituted or not substituted with fluorine atom; a cyclic heteroaliphatic hydrocarbon group having 3 to 20 carbon atoms, monocyclic, bicyclic, or fused rings; an aromatic hydrocarbon group having 6 to 25 carbon atoms, monocyclic, bicyclic, or fused rings; a heteroaromatic group having 3 to 25 carbon atoms, monocyclic, bicyclic, or fused rings; or the formula (555).

30. The compound according to any one of claims 25 to 28, wherein, Each of the given expressions A′ is independently represented by any one of the following expressions (6-1) to (6-36). In the formulas (6-1) to (6-36), R 501 ~R 586 Each can be represented independently as: hydrogen atom; deuterium atom; fluorine atom; bromine atom; chlorine atom; a straight-chain or branched aliphatic hydrocarbon group with 1 to 4 carbon atoms; a straight-chain or branched alkoxy group with 1 to 4 carbon atoms, substituted or unsubstituted; a cyclic aliphatic hydrocarbon group with 5 to 20 carbon atoms, substituted or unsubstituted; a cyclic heteroaliphatic hydrocarbon group with 3 to 20 carbon atoms, substituted or unsubstituted; an aromatic hydrocarbon group with 6 to 20 carbon atoms, substituted or unsubstituted; or a heteroaromatic group with 3 to 20 carbon atoms, substituted or unsubstituted. L 601 ~L 660 Each of these elements independently represents a straight-chain or branched divalent aliphatic hydrocarbon group, oxygen atom, sulfur atom, or single bond with 1 to 4 carbon atoms. L 701 ~L 760 Each of these elements independently represents a straight-chain or branched divalent aliphatic hydrocarbon group, oxygen atom, sulfur atom, or single bond with 1 to 4 carbon atoms. p and q each independently represent integers from 0 to 11. This represents a bonding bond.

31. A thin film for patterning metals, characterized in that, The metal patterning film comprises any one of claims 1 to 12, or comprises a metal patterning material containing any one of claims 13 to 30, wherein the metal patterning film is capable of patterning a metal film or a metal laminate.

32. The thin film for metal patterning according to claim 31, wherein, The water contact angle of the metal patterning film is 90° or higher.

33. An organic electroluminescent element, characterized in that, Equipped with a cathode, The cathode contains at least one element selected from ytterbium, magnesium, silver, lithium, aluminum, and alloys of magnesium and silver. The cathode is patterned using the metal patterning material according to any one of claims 1 to 12, or a metal patterning material containing the compound according to any one of claims 13 to 30.

34. A method for forming a metallic pattern, characterized in that, include: The process of forming an organic material pattern on a substrate using any one of the metal patterning materials according to claims 1 to 12, or a metal patterning material containing any one of the compounds according to claims 13 to 30; as well as The process of applying a metallic material to the forming area and the non-forming area of ​​the organic material pattern to form a metallic pattern on the non-forming area.

35. An electronic device, characterized in that, It comprises the metal patterned material according to any one of claims 1 to 12, or the compound according to any one of claims 13 to 30.

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