WO2017170465A1 - 感光性組成物 - Google Patents

感光性組成物 Download PDF

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Publication number
WO2017170465A1
WO2017170465A1 PCT/JP2017/012505 JP2017012505W WO2017170465A1 WO 2017170465 A1 WO2017170465 A1 WO 2017170465A1 JP 2017012505 W JP2017012505 W JP 2017012505W WO 2017170465 A1 WO2017170465 A1 WO 2017170465A1
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group
carbon atoms
represented
groups
general formula
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PCT/JP2017/012505
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English (en)
French (fr)
Japanese (ja)
Inventor
有希子 金原
友泰 川原
依純 松井
光裕 岡田
直美 佐藤
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株式会社Adeka
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Priority to KR1020187015981A priority Critical patent/KR102369445B1/ko
Priority to CN201780005076.5A priority patent/CN108473611B/zh
Priority to JP2018508022A priority patent/JP6849659B2/ja
Publication of WO2017170465A1 publication Critical patent/WO2017170465A1/ja

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/08—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated side groups
    • C08F290/12—Polymers provided for in subclasses C08C or C08F
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators

Definitions

  • the present invention has a latent additive, an ethylenically unsaturated bond, and a hydrophilic group that are inactive at normal temperature and activated by heating to a predetermined temperature to exhibit a function, and are constant.
  • the present invention relates to a photosensitive composition containing a polymer having a double bond equivalent of: Furthermore, the present invention relates to a colored photosensitive composition that can be polymerized by energy rays using the composition, and a color filter that uses the colored photosensitive composition.
  • Patent Document 1 In order to improve the weather resistance and heat resistance of a resin composition, a method of stabilizing by adding an ultraviolet absorber or an antioxidant is known (Patent Document 1).
  • Patent Document 6 Since phenolic antioxidants trap radicals that greatly affect the deterioration of the polymer, adding antioxidants to the polymerization system generally acts as a so-called polymerization inhibitor, causing inhibition of curing. Therefore, latent additives have been developed (Patent Document 6).
  • an object of the present invention is to have a latent additive, an ethylenically unsaturated bond and a hydrophilic group in one molecule which are inactive at room temperature and are activated by heating to a predetermined temperature to exhibit a function.
  • Another object of the present invention is to provide a photosensitive composition comprising a polymer having a certain double bond equivalent, an acrylic monomer, and a radical photopolymerization initiator.
  • the present invention has been made on the basis of the above findings, and is a latent additive (A) that is inactive at room temperature and is activated by heating to a predetermined temperature to express its function (hereinafter, the latent additive ( A)), a polymer (B) having an ethylenically unsaturated bond and a hydrophilic group in one molecule and having a double bond equivalent of 200 to 1000 (hereinafter also referred to as polymer (B))
  • the photosensitive composition containing an acrylic monomer (C) and a radical photopolymerization initiator (D) is provided.
  • the photosensitive composition of the present invention comprises a latent additive (A), a polymer (B) having an ethylenically unsaturated bond and a hydrophilic group in one molecule and a double bond equivalent of 200 to 1000, Contains an acrylic monomer (C) and a radical photopolymerization initiator (D).
  • a latent additive A
  • B a polymer having an ethylenically unsaturated bond and a hydrophilic group in one molecule and a double bond equivalent of 200 to 1000
  • C acrylic monomer
  • D radical photopolymerization initiator
  • the latent additive (A) used in the photosensitive composition of the present invention is inactive at room temperature or in the pre-baking step, and is heated at 100 to 250 ° C. or 80 to 200 ° C. in the presence of an acid / base catalyst. The protecting group is eliminated and becomes active by heating with.
  • the latent additive (A) is active, it means that it has reactivity with radicals, and when it is inactive, it means that it does not react with radicals or has extremely low reactivity.
  • the latent additive (A) has a skeleton represented by the following general formula (I) because synthesis is easy and heat resistance is high.
  • ring A 1 represents a 5-membered or 6-membered hydrocarbon ring, heterocyclic ring or condensed ring;
  • R 61 each independently has a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, a C 1-40 alkyl group that may have a substituent, or a substituent.
  • R 62 each independently represents an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, carbon Represents a heterocyclic group containing 2 to 20 atoms or a trialkylsilyl group
  • the methylene group in the alkyl group or arylalkyl group represented by R 61 and R 62 is a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —CO—O.
  • a group selected from —, —NH—CO—, —NH—CO—O—, —NR′—, —SS— or —SO 2 — is replaced with a group which is combined under the condition that oxygen atoms are not adjacent to each other.
  • R ′ represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms
  • a plurality of R 61 may be bonded to each other to form a benzene ring or a naphthalene ring
  • d represents an integer of 0 to 4
  • k represents an integer of 1 to 5, but the sum of d and k is less than the number of substituents that ring A 1 can take;
  • * Means that it is bonded to an adjacent group at the * part. )
  • the heterocyclic group having 2 to 20 carbon atoms means a group containing at least one heterocyclic ring and having 2 to 20 carbon atoms in the whole group.
  • the heterocycle-containing group having 2 to 10 carbon atoms described later means a group containing at least one heterocycle and having 2 to 10 carbon atoms as a whole.
  • the heterocycle-containing group having 2 to 35 carbon atoms described later means a group containing at least one heterocycle and having 2 to 35 carbon atoms as a whole.
  • the number of carbon atoms of the whole group may exceed the upper limit of each group.
  • examples of the substituent include those exemplified as the substituent that may substitute a group represented by X 1 described later.
  • Examples of the five-membered hydrocarbon ring represented by A 1 in the general formula (I) include cyclopentadiene, and examples of the five-membered heterocyclic ring include furan, thiophene, pyrrole, pyrrolidine, pyrazolidine, and pyrazole.
  • Imidazole imidazolidine, oxazole, isoxazole, isoxazolidine, thiazole, isothiazole, isothiazolidine, etc., as the six-membered hydrocarbon ring, benzene and the like, and as the six-membered heterocyclic ring, Piperidine, piperazine, morpholine, thiomorpholine, pyridine, pyrazine, pyrimidine, pyridazine, triazine, etc. are mentioned, and these rings may be condensed or substituted with other rings.
  • quinoline isoquinoline, indole, urolidine, ben
  • examples include zoxazole, benzotriazole, azulene, naphthalene, anthracene, fluorene, perylene, and pyrene.
  • halogen atom represented by R 61 in the general formula (I) examples include fluorine, chlorine, bromine and iodine. (In the description below, all the halogen atoms are the same as described above. ).
  • Examples of the alkyl group having 1 to 40 carbon atoms represented by R 61 in the general formula (I) include methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, iso-butyl, amyl , Iso-amyl, tert-amyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, 4-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, iso-heptyl, tert-heptyl, 1-octyl, iso-octyl, tert-octyl, adamantyl and the like,
  • Substituents for substituting the heterocyclic ring-containing groups include ethylenically unsaturated groups such as vinyl, allyl, acrylic and methacryl; halogen atoms such as fluorine, chlorine, bromine and iodine; acetyl, 2-chloroacetyl, propionyl and octanoyl
  • Acyl groups such as acryloyl, methacryloyl, phenylcarbonyl (benzoyl), phthaloyl, 4-trifluoromethylbenzoyl, pivaloyl, salicyloyl, oxaloyl, stearoyl, methoxycarbonyl, ethoxycarbonyl, t-but
  • Examples of the aryl group having 6 to 20 carbon atoms represented by R 61 and R 62 in the general formula (I) include phenyl, naphthyl, anthracenyl, phenanthryl, fluorenyl, indenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 4-vinylphenyl, 3-iso-propylphenyl, 4-iso-propylphenyl, 4-butylphenyl, 4-iso-butylphenyl, 4-tert-butylphenyl, 4-hexylphenyl, 4- Cyclohexylphenyl, 4-octylphenyl, 4- (2-ethylhexyl) phenyl, 4-stearylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-di
  • Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R 61 and R 62 in the general formula (I) include benzyl, 1-methyl-1-phenylethyl, 1-naphthylmethyl, 9-anthracenyl Examples include methyl, 9-fluorenyl, 3-phenylpropyl, methyl-2-phenylpropan-2-yl, diphenylmethyl, triphenylmethyl, phenethyl, styryl, cinnamyl and the like.
  • Examples of the heterocyclic ring-containing group having 2 to 20 carbon atoms represented by R 61 and R 62 in the general formula (I) include a pyridine ring, a pyrimidine ring, a pyridazine ring, a piperidine ring, a pyran ring, a pyrazoline ring, and a triazine ring.
  • Examples of the alkyl group having 1 to 20 carbon atoms represented by R 62 in the general formula (I) include those satisfying a predetermined number of carbon atoms among the alkyl groups represented by R 61 .
  • Examples of the alkenyl group having 2 to 20 carbon atoms represented by R 62 in the general formula (I) include vinyl, 1-methylethen-1-yl, propen-1-yl, propen-2-yl and propene-3. -Yl, buten-1-yl, buten-2-yl, 2-methylpropen-3-yl, 1,1-dimethylethen-2-yl, 1,1-dimethylpropen-3-yl, 3-butenyl, Examples include 1-methyl-3-butenyl, isobutenyl, 3-pentenyl, 4-hexenyl, cyclohexenyl, bicyclohexenyl, heptenyl, octenyl, decenyl, pentadecenyl, eicosenyl, tricoseni and the like.
  • Examples of the trialkylsilyl group represented by R 62 in the general formula (I) include alkyl groups having 1 to 6 carbon atoms such as trimethylsilane, triethylsilane, and ethyldimethylsilane (the three alkyl groups may be the same or different. Silyl group substituted with (good).
  • Examples of the alkyl group having 1 to 8 carbon atoms represented by R ′ in the general formula (I) include those satisfying a predetermined number of carbon atoms among the alkyl groups represented by R 61 .
  • R 61 is preferably a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, or an aryl group having 6 to 12 carbon atoms because synthesis is easy.
  • R 62 is an alkyl group having 1 to 8 carbon atoms in which —CO—O— is bonded to the terminal on the oxygen atom side and functions effectively as a latent additive. Is preferable.
  • X 1 represents an m-valent organic group, specifically, a direct bond, a hydrogen atom, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, the following (Ia ) Or (Ib),>C ⁇ O,> NR 63 , —OR 63 , —SR 63 , —NR 63 R 64 , or the same number as m which may have a substituent.
  • the methylene group is a carbon-carbon double bond, —O—, —S—, —CO—, —O—CO—, —CO—O—, —O—CO—O—, —O—CO—O.
  • X 1 is a nitrogen atom, a phosphorus atom or a group represented by the following (Ia) or (Ib), m is 3, X 1 is an oxygen atom or a sulfur atom, and> C ⁇ O , —NH—CO—, —CO—NH— or> NR 63 , m is 2, and when X 1 is —OR 63 , —SR 63 or —NR 63 R 64 , m is 1. X 1 may form a ring together with A 1 .
  • the latent additive represented by the general formula (IA) has a structure in which m specific groups are bonded to the m-valent specific atom or group represented by X 1 .
  • the m groups are the same as or different from each other.
  • the value of m is 1 to 10, and preferably 2 to 6 from the viewpoint of ease of synthesis.
  • m is monovalent, for example, methyl Ethyl, propyl, isopropyl, cyclopropyl, butyl, sec-butyl, sec-butyl, isobutyl, amyl, isoamyl, tert-amyl, cyclopentyl, hexyl, 2-hexyl, 3-hexyl, cyclohexyl, bicyclohexyl, 1-methyl Alkyl groups such as cyclohexyl, heptyl, 2-heptyl, 3-heptyl, isoheptyl, tertiary heptyl, n-octyl, isooctyl, tertiary octyl, 2-ethylhexyl, nonyl, isononyl,
  • the aliphatic hydrocarbon group having 1 to 120 carbon atoms having the same valence as m represented by X 1 is methylene, ethylene where m is divalent.
  • Alkylene such as propylene, butylene, butyldiyl, etc .; in which the methylene chain of the alkylene is replaced by —O—, —S—, —CO—O—, —O—CO—; ethanediol, propanediol, butanediol, Residues of diols such as pentanediol and hexanediol; residues of dithiols such as ethanedithiol, propanedithiol, butanedithiol, pentanedithiol and hexanedithiol, and groups in which these groups are substituted by substituents described later, etc. .
  • Examples of the aliphatic hydrocarbon group having 1 to 120 carbon atoms and having the same valence as m represented by X 1 in the general formula (IA) are those in which m is trivalent. Examples thereof include alkylidine such as pyridine and 1,1,3-butyridine, and groups in which these groups are substituted with a substituent described later.
  • M is monovalent, arylalkyl groups such as benzyl, phenethyl, diphenylmethyl, triphenylmethyl, styryl and cinnamyl; aryl groups such as phenyl and naphthyl; aryloxy groups such as phenoxy and naphthyloxy; phenylthio and naphthylthio And arylthio groups such as these, and groups in which these groups are substituted with a substituent described later.
  • m is divalent, arylene groups such as phenylene and naphthylene; residues of bifunctional phenols such as catechol and bisphenol; 2,4,8,10-tetraoxaspiro [5,5] undecane and the like and these groups Is a group substituted by a substituent described later.
  • m being trivalent include phenyl-1,3,5-trimethylene and groups in which these groups are substituted with a substituent described later.
  • m is As monovalent ones, pyridyl, pyrimidyl, pyrariayl, piperidyl, pyranyl, pyrazolyl, triazyl, pyrrolyl, quinolyl, isoquinolyl, imidazolyl, benzoimidazolyl, triazolyl, furyl, furanyl, benzofuranyl, thienyl, thiophenyl, benzothiophenyl, thiadiazolyl, thiazolyl, Benzothiazolyl, oxazolyl, benzoxazolyl, isothiazolyl, isoxazolyl, indolyl, 2-pyrrolidinon-1-yl, 2-piperidone-1-yl, 2,4-dioxyimidazolidin-3-yl
  • m is examples of the divalent group include a group having a pyridine ring, a pyrimidine ring, a piperidine ring, a piperazine ring, a triazine ring, a furan ring, a thiophene ring, an indole ring, or the like, and a group in which these groups are substituted with a substituent described later. .
  • m is
  • the trivalent group include a group having an isocyanuric ring, a group having a triazine ring, and a group in which these groups are substituted with a substituent described later.
  • Examples of the aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent represented by R 63 and R 64 include an aliphatic hydrocarbon group having 1 to 120 carbon atoms represented by the above X 1 Among the combinations of an aromatic hydrocarbon group or the aliphatic hydrocarbon group and a substituent described later, those satisfying a predetermined number of carbon atoms can be mentioned.
  • an aliphatic hydrocarbon group having 1 to 120 carbon atoms, an aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, and a heterocyclic ring-containing group having 2 to 35 carbon atoms represented by X 1 may be substituted.
  • substituents that may be substituted for the heterocyclic ring-containing groups include ethylenically unsaturated groups such as vinyl, allyl, acrylic, and methacryl; halogen atoms such as fluorine, chlorine, bromine, and iodine; acetyl, 2-chloroacetyl, propionyl , Octanoyl, acryloyl, methacryloyl, phenylcarbonyl (benzoyl), phthaloyl, 4-trifluoromethylbenzoyl, pivaloyl, salicyloyl, oxaloyl, stearo Acyl groups such as acetyloxy, benzoyloxy, etc .; amino, ethylamino
  • Examples of the alkyl group having 1 to 8 carbon atoms represented by R ′ in the general formula (IA) include those having the predetermined number of carbon atoms among the alkyl groups represented by R 61 described above. Can be mentioned.
  • X 1 when m is 2, X 1 can also be represented by the following general formula (1).
  • Y 10 represents a single bond, —CR 65 R 66 —, —NR 67 —, a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, or 6 to 35 carbon atoms.
  • the terminal carbon atom of the aliphatic hydrocarbon group may be replaced with —O—, —S—, —CO—, —COO—, —OCO— or —NH—
  • the aliphatic hydrocarbon group may be substituted with a hydroxyl group, a halogen atom, a cyano group, a nitro group, a carboxyl group or an alkoxy group
  • Z 1 and Z 2 are each independently a direct bond, —O—, —S—,> CO, —CO—O—, —O—CO—, —SO 2 —, —SS—, —SO—,
  • Represents> NR 67 or> PR 67 , R 65 , R 66 and R 67 each independently have a hydrogen atom, a hydroxyl group or a substituent, or may have an aliphatic hydrocarbon group having 1 to 35 carbon atoms or a substituent.
  • R 71 represents a hydrogen atom, a phenyl group which may have a substituent, or a cycloalkyl group having 3 to 10 carbon atoms
  • R 72 represents an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, or a halogen atom
  • the alkyl group, alkoxy group and alkenyl group may have a substituent
  • f is an integer of 0 to 5
  • * means that it is bonded to an adjacent group at the * portion.
  • R 73 and R 74 are each independently an alkyl group having 1 to 10 carbon atoms which may have a substituent, or 6 carbon atoms which may have a substituent.
  • the methylene group in the alkyl group and arylalkyl group may be replaced with an unsaturated bond, —O— or —S—, R 73 may form a ring with adjacent R 73 , p represents
  • X 1 can also be represented by the following general formula (2).
  • Y 11 represents a single bond, a trivalent aliphatic hydrocarbon group having 3 to 35 carbon atoms, a trivalent alicyclic hydrocarbon group having 3 to 35 carbon atoms, 3 A valent aromatic hydrocarbon group having 6 to 35 carbon atoms or a trivalent heterocyclic group having 2 to 35 carbon atoms, Z 1 , Z 2 and Z 3 are each independently a direct bond, —O—, —S—,> CO, —CO—O—, —O—CO—, —SO 2 —, —SS—, — SO-,> NR 68 or> PR 68 , R 68 is a hydrogen atom, an aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent, or an aromatic carbon group having 6 to 35 carbon atoms which may have a substituent.
  • the adjacent carbon atom of the aliphatic hydrocarbon group is interrupted by a carbon-carbon double bond, —O—, —CO—, —O—CO—, —CO—O— or —SO 2 —.
  • the terminal carbon atom of the aliphatic hydrocarbon group may be replaced with a carbon-carbon double bond, —O—, —CO—, —O—CO—, —CO—O— or —SO 2 —. is there. )
  • X 1 when m is 4, X 1 can also be represented by the following general formula (3).
  • Y 12 represents a single bond, a carbon atom, or a tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms and a tetravalent aromatic carbon group having 6 to 35 carbon atoms.
  • the adjacent carbon atom of the aliphatic hydrocarbon group may be interrupted by —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—
  • the terminal carbon atom of the aliphatic hydrocarbon group may be replaced with —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—
  • Z 1 to Z 4 are each independently a group in the same range as the group represented by Z 1 to Z 3 in the general formula (2).
  • Y 13 represents a single bond, a 5-valent aliphatic hydrocarbon group having 2 to 35 carbon atoms, a 5-valent aromatic hydrocarbon group having 6 to 20 carbon atoms, or a pentavalent group.
  • the adjacent carbon atom of the aliphatic hydrocarbon group may be interrupted by —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—
  • the terminal carbon atom of the aliphatic hydrocarbon group may be replaced with —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—
  • Z 1 to Z 5 are each independently a group within the same range as the group represented by Z 1 to Z 3 in the general formula (2).
  • Y 14 is a single bond, a hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, a hexavalent aromatic hydrocarbon group having 6 to 35 carbon atoms, or a hexavalent group.
  • the adjacent carbon atom of the aliphatic hydrocarbon group may be interrupted by —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—
  • the terminal carbon atom of the aliphatic hydrocarbon group may be replaced with —COO—, —O—, —OCO—, —NHCO—, —NH— or —CONH—
  • Z 1 to Z 6 are each independently a group in the same range as the group represented by Z 1 to Z 3 in the general formula (2).
  • the aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent represented by R 65 , R 66 and R 67 includes the general formula (I- A monovalent aliphatic hydrocarbon group having 1 to 120 carbon atoms exemplified as the m-valent organic group represented by X 1 in A) and these groups are represented by X 1 in the general formula (IA).
  • Examples include groups substituted by those exemplified as the substituent of the group representing the organic group, and these groups or 2 exemplified as the m-valent organic group represented by X 1 in the general formula (IA).
  • the heterocyclic group containing 2 to 35 carbon atoms which may have a substituent represented by R 65 , R 66 and R 67 is represented by X 1 in the above general formula (IA).
  • the monovalent heterocyclic group having 2 to 35 carbon atoms exemplified as the m-valent organic group and these groups represent the m-valent organic group represented by X 1 in the general formula (IA).
  • Examples of the divalent group in which the aromatic ring-containing hydrocarbon group having 2 to 35 is substituted with Z 1 and Z 2 include the divalent heterocyclic group having 2 to 35 carbon atoms represented by Y 10. .
  • examples of the cycloalkyl group having 3 to 10 carbon atoms represented by R 71 include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and the like.
  • the alkyl group having 1 to 10 carbon atoms represented by R 72 is exemplified as the alkyl group having 1 to 40 carbon atoms represented by R 61 .
  • the groups satisfying a predetermined number of carbon atoms can be mentioned.
  • examples of the alkoxy group having 1 to 10 carbon atoms represented by R 72 include methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, sec-butyloxy, Tributyloxy, isobutyloxy, amyloxy, isoamyloxy, tertiary amyloxy, hexyloxy, cyclohexyloxy, heptyloxy, isoheptyloxy, tertiary heptyloxy, n-octyloxy, isooctyloxy, tertiary octyloxy, 2-ethylhexyl Examples include oxy, nonyloxy, decyloxy and the like.
  • the substituent of the phenyl group, alkyl group, alkoxy group and alkenyl group is an m-valent organic compound represented by X 1 in the general formula (IA). The same as those exemplified as the substituent of the group representing the group.
  • the alkyl group having 1 to 10 carbon atoms which may have a substituent represented by R 73 and R 74 is represented by R 61.
  • R 61 groups satisfying a predetermined number of carbon atoms are exemplified.
  • the aryl group having 6 to 20 carbon atoms, which may have a substituent represented by R 73 and R 74 includes R 61 and R 62 Examples thereof include the groups exemplified as the aryl group having 6 to 20 carbon atoms.
  • the aryloxy group having 6 to 20 carbon atoms which may have a substituent represented by R 73 and R 74 includes phenyloxy, naphthyloxy 2-methylphenyloxy, 3-methylphenyloxy, 4-methylphenyloxy, 4-vinylphenyldioxy, 3-iso-propylphenyloxy, 4-iso-propylphenyloxy, 4-butylphenyloxy, 4- tert-butylphenyloxy, 4-hexylphenyloxy, 4-cyclohexylphenyloxy, 4-octylphenyloxy, 4- (2-ethylhexyl) phenyloxy, 2,3-dimethylphenyloxy, 2,4-dimethylphenyloxy 2,5-dimethylphenyloxy, 2.6-dimethylphenyloxy 3,4-dimethylphenyloxy, 3.5-dimethylphenyloxy, 2,4-di-tert-
  • the arylthio group having 6 to 20 carbon atoms which may have a substituent represented by R 73 and R 74 has the above substituent.
  • a group in which the oxygen atom of the aryloxy group having 6 to 20 carbon atoms is substituted with a sulfur atom is used.
  • the arylalkenyl group having 6 to 20 carbon atoms, which may have a substituent represented by R 73 and R 74 has the above substituent.
  • the oxygen atom of the aryloxy group having 6 to 20 carbon atoms may be vinyl, allyl, 1-propenyl, isopropenyl, 2-butenyl, 1,3-butadienyl, 2-pentenyl, 2-octenyl, etc. And a group substituted with an alkenyl group.
  • the arylalkyl group having 7 to 20 carbon atoms represented by R 73 and R 74 includes 7 to 20 carbon atoms represented by R 61 and R 62.
  • the groups exemplified as the arylalkyl group are examples of the arylalkyl group.
  • the heterocyclic group containing 2 to 20 carbon atoms which may have a substituent represented by R 73 and R 74 includes R 61 and R And the groups exemplified as the heterocyclic-containing group having 2 to 20 carbon atoms represented by 62 .
  • the trivalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by Y 11 in the general formula (2) is an m-valent organic compound represented by X 1 in the general formula (IA).
  • Examples of the group substituted by 1 include those having a predetermined number of carbon atoms, such as trivalent groups substituted with Z 1 , Z 2 and Z 3 .
  • Examples of the trivalent alicyclic hydrocarbon group having 3 to 35 carbon atoms represented by Y 11 in the general formula (2) include cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecanyl, 1-adamantyl, 2- Adamantyl, noradamantyl, 2-methyladamantyl, norbornyl, isonorbornyl, perhydronaphthyl, perhydroanthracenyl, bicyclo [1.1.0] butyl, bicyclo [1.1.1] pentyl, bicyclo [2.1.
  • the trivalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 11 in the general formula (2) is an m-valent represented by X 1 in the general formula (IA).
  • Examples of monovalent to trivalent aromatic ring-containing hydrocarbon groups exemplified as the organic group and substituents of the groups in which these groups represent the m-valent organic group represented by X 1 in the general formula (IA) And a trivalent group in which a group substituted by the above is substituted with Z 1 , Z 2 and Z 3 .
  • Examples of the trivalent heterocyclic group having 2 to 35 carbon atoms represented by Y 11 in the general formula (2) include an m-valent organic group represented by X 1 in the general formula (IA).
  • the aromatic hydrocarbon group having 6 to 35 and the heterocyclic group having 2 to 35 carbon atoms which may have a substituent include R 65 and R 66 in the general formula (1), respectively.
  • Examples include the aliphatic hydrocarbon group, aromatic ring-containing hydrocarbon group, and heterocyclic ring-containing group exemplified in the description.
  • the tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by Y 12 in the general formula (3) is an m-valent organic compound represented by X 1 in the general formula (IA).
  • Examples of the group substituted by 1 include those having a predetermined number of carbon atoms, such as tetravalent groups substituted with Z 1 , Z 2 , Z 3 and Z 4 .
  • the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 12 in the general formula (3) is an m-valent organic group represented by X 1 in the general formula (IA).
  • X 1 in the general formula (IA) By the exemplified monovalent to trivalent aromatic ring-containing hydrocarbon groups and those exemplified as substituents for the group representing the m-valent organic group represented by X 1 in the general formula (IA). Examples thereof include a tetravalent group in which a substituted group or the like is substituted with Z 1 , Z 2 , Z 3, or Z 4 .
  • the tetravalent heterocyclic containing group having a carbon number of 2 to 35 represented by Y 12 in general formula (3), m-valent organic group represented by X 1 in the above formula (I-A) The monovalent to trivalent heterocyclic-containing groups exemplified as above and these groups substituted by those exemplified as the substituents of the group representing the m-valent organic group represented by X 1 in the general formula (IA) And tetravalent groups in which the group and the like are substituted with Z 1 , Z 2 , Z 3 and Z 4 .
  • the pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms represented by Y 13 in the general formula (4) is an m-valent organic compound represented by X 1 in the general formula (IA).
  • Examples of monovalent to trivalent aliphatic hydrocarbon groups exemplified as the groups and substituents of the groups in which these groups represent the m-valent organic group represented by X 1 in the general formula (IA) Among the groups substituted by the above, there are pentavalent groups in which those satisfying the predetermined number of carbon atoms are substituted with Z 1 , Z 2 , Z 3 , Z 4 and Z 5 .
  • the pentavalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 14 in the general formula (4) is an m-valent represented by X 1 in the general formula (IA).
  • Examples of monovalent to trivalent aromatic ring-containing hydrocarbon groups exemplified as organic groups and substituents of groups in which these groups represent an n-valent organic group represented by X 1 in the above general formula (IA)
  • a pentavalent group in which a group substituted by the above-described one is substituted with Z 1 , Z 2 , Z 3 , Z 4 and Z 5 .
  • the pentavalent C2-C35 heterocycle-containing group represented by Y 14 in the general formula (4) is X in the m valence represented by X 1 in the general formula (IA).
  • X 1 in the general formula (IA) Of the monovalent to trivalent heterocyclic group exemplified as the represented n-valent organic group and the group in which these groups represent the m-valent organic group represented by X 1 in the general formula (IA). Examples thereof include pentavalent groups in which groups substituted by those exemplified as the substituent are substituted with Z 1 , Z 2 , Z 3 , Z 4 and Z 5 .
  • the hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms represented by Y 14 in the general formula (5) is an m-valent organic compound represented by X 1 in the general formula (IA).
  • Examples of the group substituted by the above group include those having a predetermined number of carbon atoms and the like, and hexavalent groups substituted with Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 .
  • the hexavalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 14 in the general formula (5) is an m-valent represented by X 1 in the general formula (IA).
  • Examples of monovalent to trivalent aromatic ring-containing hydrocarbon groups exemplified as the organic group and substituents of the groups in which these groups represent the m-valent organic group represented by X 1 in the general formula (IA)
  • a hexavalent group in which a group substituted by the above-described one is substituted with Z 1 , Z 2 , Z 3 , Z 4 , Z 5 and Z 6 .
  • the hexavalent heterocyclic group having 2 to 35 carbon atoms represented by Y 14 in the general formula (5) is an m-valent organic group represented by X 1 in the general formula (IA).
  • hexavalent to groups substituted by those exemplified as the substituents exemplified monovalent to trivalent heterocyclic containing groups is substituted with Z 1, Z 2, Z 3 , Z 4, Z 5 and Z 6 as And the like.
  • the sum of d and k is less than the number of substituents that can be taken by the ring A 1 .
  • the possible substituents of the ring A 1 are 6, and d + k ⁇ 5.
  • the possible substituents of the ring A 1 are 4, and d + k ⁇ 3.
  • ring A 2 is a six-membered alicyclic ring, aromatic ring or heterocyclic ring, and R 81 , R 82 , R 83 , R 84 and R 85 are a hydrogen atom, a halogen atom, a cyano group, or a hydroxyl group.
  • Nitro group carboxyl group, alkyl group having 1 to 40 carbon atoms, aryl group having 6 to 20 carbon atoms, arylalkyl group having 7 to 20 carbon atoms, carbon atom Represents a heterocyclic group containing 2 to 20 or —O—R 62 , wherein at least one of R 81 , R 82 , R 83 , R 84 and R 85 is not a hydrogen atom, and R 62 represents the above general formula Same as (I).)
  • X 2 is a group represented by the above general formula (1), and R 86 , R 87 , R 88 and R 89 are a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group.
  • R 86 , R 87 , R 88 and R 89 are a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group.
  • R 86 , R 87 , R 88 and R 89 is not a hydrogen atom
  • R 62 is the same as in the above general formula (I)
  • ring A 2 is (It is the same as general formula (II).)
  • R 91 , R 92 , R 93 and R 94 may have a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group or a substituent.
  • Examples of the six-membered alicyclic, aromatic or heterocyclic ring represented by the ring A 2 in the general formula (II) include those exemplified in the description of A 1 in the general formula (I).
  • the halogen atom represented by R 81 , R 82 , R 83 , R 84 and R 85 in the general formula (II) an alkyl group having 1 to 40 carbon atoms which may have a substituent, a carbon atom
  • Examples of the aryl group having 6 to 20 carbon atoms, the arylalkyl group having 7 to 20 carbon atoms, and the heterocyclic ring-containing group having 2 to 20 carbon atoms are exemplified in the description of R 61 or R 62 in the general formula (I).
  • the halogen atom represented by R 86 , R 87 , R 88 and R 89 an alkyl group having 1 to 40 carbon atoms which may have a substituent, and 6 to 6 carbon atoms
  • Examples of the 20 aryl group, the arylalkyl group having 7 to 20 carbon atoms, and the heterocycle-containing group having 2 to 20 carbon atoms include those exemplified in the description of R 61 or R 62 in the general formula (I). It is done.
  • Examples of the 20 aryl group, the arylalkyl group having 7 to 20 carbon atoms, and the heterocycle-containing group having 2 to 20 carbon atoms include those exemplified in the description of R 61 or R 62 in the general formula (I). It is done.
  • Ring A 2 is preferably benzene or naphthalene
  • the groups other than hydrogen atoms include alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 10 carbon atoms, and 7 to 7 carbon atoms. 12 arylalkyl groups and heterocycle-containing groups having 2 to 10 carbon atoms are preferred.
  • any one of R 81 to R 85 is an alkyl group having 1 to 4 carbon atoms or a heterocycle having 2 to 10 carbon atoms.
  • R 62 preferably has the following substituents via —CO—O—.
  • -Alkyl groups having 1 to 8 carbon atoms (particularly methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, iso-butyl, amyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl) 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl) ⁇
  • Arylalkyl groups having 7 to 10 carbon atoms especially benzyl groups
  • Alkenyl groups having 2 to 6 carbon atoms (particularly propen-1-yl groups)
  • Ring A 2 is preferably benzene or naphthalene
  • groups other than hydrogen atoms include alkyl groups having 1 to 20 carbon atoms, aryl groups having 6 to 10 carbon atoms, and aryls having 7 to 12 carbon atoms.
  • R 62 preferably has the following substituents via —CO—O—.
  • Y 10 is preferably a sulfur atom, an aromatic ring-containing hydrocarbon group having 6 to 25 carbon atoms, or a heterocyclic ring-containing group having 2 to 21 carbon atoms, Z 1 and Z 2 may be a direct bond, —CO—O—, —O—
  • groups other than hydrogen atoms include aryl groups having 6 to 10 carbon atoms, arylalkyl groups having 7 to 12 carbon atoms, and those having 2 to 10 carbon atoms.
  • Heterocycle-containing groups particularly those in which any one of R 91 to R 94 is an alkyl group having 1 to 4 carbon atoms or a heterocycle-containing group having 2 to 10 carbon atoms are preferred.
  • R 62 preferably has the following substituents via —CO—O—.
  • -Alkyl groups having 1 to 8 carbon atoms (particularly methyl, ethyl, propyl, iso-propyl, butyl, sec-butyl, tert-butyl, iso-butyl, amyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl) 1-ethylpropyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl).
  • Arylalkyl group having 7 to 10 carbon atoms (particularly benzyl group). 2 to 6 carbon atoms Alkenyl group (especially propen-1-yl group)
  • Y 10 is a sulfur atom, a divalent alkyl group having 1 to 20 carbon atoms.
  • Divalent aromatic ring-containing hydrocarbon group having 6 to 25 carbon atoms, divalent heterocyclic group containing 2 to 21 carbon atoms, 2,4,8,10-tetraoxaspiro [5,5] undecane In particular, a divalent alkyl group having 1 to 15 carbon atoms, a divalent aromatic ring-containing hydrocarbon group having 6 to 15 carbon atoms, 2,4,8,10-tetraoxaspiro [5,5] undecane
  • Z 1 and Z 2 may have a direct bond, —CO—O—, —O—CO— or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
  • Y 11 is a trivalent alkyl group having 1 to 20 carbon atoms, trivalent An aryl group having 6 to 10 carbon atoms, a trivalent arylalkyl group having 7 to 12 carbon atoms, a trivalent heterocyclic group having 2 to 10 carbon atoms, particularly a trivalent carbon atom having 1 to 8 carbon atoms.
  • An alkyl group, a trivalent aryl group having 6 to 9 carbon atoms, and a trivalent heterocyclic group having 1 to 6 carbon atoms, Z 1 , Z 2 and Z 3 are each a direct bond, —CO—O—, —O—CO— or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
  • a divalent aromatic hydrocarbon group having 6 to 10 carbon atoms, particularly a divalent aliphatic hydrocarbon group having 1 to 8 carbon atoms which may have a substituent is preferable.
  • Y 12 represents a tetravalent alkyl group having 1 to 20 carbon atoms, a tetravalent group.
  • An alkyl group, a tetravalent aryl group having 6 to 9 carbon atoms, and a tetravalent hetero ring-containing group having 1 to 6 carbon atoms, Z 1 to Z 4 are a direct bond, —CO—O—, —O—CO— or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
  • Y 13 is a pentavalent alkyl group having 1 to 20 carbon atoms, pentavalent An aryl group having 6 to 10 carbon atoms, an arylalkyl group having 5 to 7 carbon atoms, a 5-valent heterocyclic group having 2 to 10 carbon atoms, particularly a pentavalent carbon atom having 1 to 8 carbon atoms.
  • An alkyl group, a pentavalent aryl group having 6 to 9 carbon atoms, and a pentavalent hetero ring-containing group having 1 to 6 carbon atoms, Z 1 to Z 5 are each a direct bond, —CO—O—, —O—CO— or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
  • Y 14 is a hexavalent alkyl group having 1 to 20 carbon atoms, hexavalent Aryl groups having 6 to 10 carbon atoms, arylalkyl groups having 6 to 7 carbon atoms, heterocyclic groups having 6 to 6 carbon atoms, particularly hexavalent carbon atoms having 1 to 8 carbon atoms.
  • Z 1 to Z 6 are a direct bond, —CO—O—, —O—CO— or a divalent aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
  • heterocyclic group having 2 to 10 carbon atoms described above examples include the heterocyclic group having 1 to 10 carbon atoms in the compounds exemplified as the heterocyclic group having 2 to 35 carbon atoms described above. It is done.
  • the content of the latent additive (A) is preferably 0.001 to 20% by mass, and more preferably 0.005 to 5% by mass.
  • the polymer (B) used in the photosensitive composition of the present invention is a polymer having an ethylenically unsaturated bond and a hydrophilic group in one molecule and having a double bond equivalent of 200 to 1,000.
  • the hydrophilic group possessed by the polymer (B) include a hydroxyl group, a thiol group, a carboxyl group, a sulfo group, an amino group, an amide group, or a salt thereof. This is preferable because of its high solubility in water.
  • the preferred functional group equivalent of the hydrophilic group in the polymer (B) (the mass of the polymer containing 1 equivalent of hydrophilic group) is 50 to 10,000.
  • a preferred mass average molecular weight of the polymer (B) is 3000 to 50000.
  • Examples of the polymer (B) include (meth) acrylic acid, ⁇ -chloroacrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, hymic acid, crotonic acid, isocrotonic acid, vinyl acetic acid, allyl acetic acid, and cinnamic acid. Sorbic acid, mesaconic acid, succinic acid mono [2- (meth) acryloyloxyethyl], phthalic acid mono [2- (meth) acryloyloxyethyl], ⁇ -carboxypolycaprolactone mono (meth) acrylate, etc.
  • Hydroxyl-containing polyfunctional amine Rate and succinic anhydride phthalic acid anhydride, a polyfunctional acrylate having an acid value which is a reaction product of a dibasic acid anhydride such as tetrahydrophthalic anhydride.
  • X 41 is a direct bond, an alkylene group having 1 to 4 carbon atoms which may have a substituent, or an alicyclic group having 3 to 20 carbon atoms which may have a substituent.
  • Hydrocarbon group, —O—, —S—, —SO 2 —, —SS—, —SO—, —CO—, —OCO— or a substitution represented by the above (1-1) to (1-3) Represents a group, R 41 , R 42 , R 43 and R 44 each independently have a hydrogen atom, a substituent or a C 1-5 alkyl group or a substituent.
  • those having at least one selected from units represented by the following general formula (VI-4) are preferred because of their high developability and heat resistance.
  • Y 1 represents a hydrogen atom or a methyl group
  • X 4 represents a divalent linking group
  • R 1 represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms
  • arylalkyl group having 7 to 30 carbon atoms
  • the hydrogen atom of the alkyl group, aryl group and arylalkyl group may be substituted with a halogen atom, a hydroxyl group, a nitro group or an epoxy group
  • methylene groups in arylalkyl groups may be replaced by linking groups of —O—, —S—, —CO—, —COO—, —OCO— or —NH—, or combinations thereof.
  • R 2 , R 3 and R 4 are each independently a hydrogen atom or a methyl group.
  • the divalent linking group represented by X 4 in the general formula (VI-2) is not particularly limited, but preferred examples include the structure represented by the general formula (1).
  • R 1 is preferably an alkyl group having 1 to 8 carbon atoms and an arylalkyl group having 7 to 30 carbon atoms, and more preferably an alkyl group having 1 to 4 carbon atoms.
  • X 4 is a structure in which a divalent linking group is represented by the following general formula (1), Y 10 is preferably an alkylene group having 1 to 15 carbon atoms, and has 7 carbon atoms having a cycloalkylene group. Those having a substituent having ⁇ 15 alkylene groups or carboxyl groups are more preferred.
  • the hydrogen atom in these alkylene groups may be substituted with a halogen atom, a hydroxyl group or a nitro atom, and the methylene group in the chain alkylene portion in the alkylene group is —O—, —S—, —CO. It may be replaced by a —, —COO—, —OCO— or —NH— group.
  • Z 1 and Z 2 are preferably direct bonds.
  • the polymer (B) has an acid value of preferably 10 to 200 mg / KOH, more preferably 30 to 150 mg / KOH. If the acid value is less than 10 mg / KOH, sufficient alkali developability may not be obtained, and if it is greater than 200 mg / KOH, the production of the polymer (B) may be difficult.
  • the acid value is based on JIS K 0050 and JIS K 0211.
  • the polymer (B) must have a double bond equivalent of 200 to 1000, preferably 300 to 500. If the double bond equivalent in the polymer (B) is less than 200, production is difficult, and if it is greater than 1000, sufficient durability cannot be obtained.
  • the content of the polymer (B) is preferably 1 to 20% by mass, particularly preferably 5 to 15% by mass in the photosensitive composition of the present invention.
  • the content of the polymer (B) is less than 1% by mass, resolution and durability may not be sufficiently obtained.
  • the content is more than 20% by mass, alkali developability and curability may not be sufficiently obtained. There is.
  • the acrylic monomer (C) used in the photosensitive composition of the present invention is not particularly limited and known ones can be used.
  • the content of the acrylic monomer (C) is preferably 1 to 20% by mass, particularly preferably 5 to 15% by mass in the photosensitive composition of the present invention.
  • the content of the acrylic monomer (C) is less than 1% by mass, sufficient curability and alkali developability may not be obtained.
  • the content is more than 20% by mass, sufficient resolution and durability may not be obtained. There is.
  • the radical photopolymerization initiator (D) used in the photosensitive composition of the present invention may be any compound that can initiate radical polymerization upon receiving light irradiation, such as an acetophenone compound or a benzyl compound.
  • Preferred examples include compounds, ketone compounds such as benzophenone compounds and thioxanthone compounds, and oxime compounds.
  • acetophenone compounds include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 4′-isopropyl-2-hydroxy-2-methylpropiophenone, and 2-hydroxymethyl-2.
  • benzylic compound examples include benzyl and anisyl.
  • benzophenone compounds include benzophenone, methyl o-benzoylbenzoate, Michler's ketone, 4,4′-bisdiethylaminobenzophenone, 4,4′-dichlorobenzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, and the like.
  • thioxanthone compound examples include thioxanthone, 2-methylthioxanthone, 2-ethylthioxanthone, 2-chlorothioxanthone, 2-isopropylthioxanthone, and 2,4-diethylthioxanthone.
  • oxime compound a compound represented by the following general formula (VII) or (VIII) is particularly preferable from the viewpoint of sensitivity and heat resistance.
  • R 51 and R 52 each independently have a hydrogen atom, a cyano group, a substituent, or an alkyl group having 1 to 20 carbon atoms or a substituent.
  • a certain aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms which may have a substituent or a complex having 2 to 20 carbon atoms which may have a substituent Represents a ring-containing group
  • R 53 and R 54 are each independently a halogen atom, nitro group, cyano group, hydroxyl group, carboxyl group, R 55 , OR 56 , SR 57 , NR 58 R 59 , COR 60 , SOR 61 , SO 2 R 62 or CONR 63 R 64 , R 53 and R 54 may be bonded to each other to form a ring, R 55 , R 56 , R 57 , R 58 , R 59 , R 60 , R 61 , R RI
  • aryl groups having 6 to 30 carbon atoms which may have substituents arylalkyl groups having 7 to 30 carbon atoms which may have substituents or substituents
  • X 5 represents an oxygen atom, a sulfur atom, a selenium atom, CR 75 R 76 , CO, NR 77 or PR 78
  • X 6 represents a single bond or CO
  • carbon atoms Represents a 6-30 aryl group or an arylalkyl group having 7-30 carbon atoms, and the methylene group in the alkyl group or arylalkyl group contains a halogen atom, a nitro
  • R 101 and R 102 each independently represent R 111 , OR 111 , COR 111 , SR 111 , CONR 112 R 113 or CN;
  • R 111 , R 112 and R 113 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or a carbon atom.
  • R 111 , R 112 and R 113 Represents a heterocyclic-containing group of formula 2 to 20,
  • the hydrogen atoms of the groups represented by R 111 , R 112 and R 113 are further R 121 , OR 121 , COR 121 , SR 121 , NR 122 R 123 , CONR 122 R 123 , —NR 122 —OR 123 , —NCOR 122.
  • R 121 , R 122 and R 123 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms or a carbon atom Represents a heterocyclic-containing group of formula 2 to 20,
  • the hydrogen atom of the group represented by R 121 , R 122 and R 123 may be further substituted with a hydroxyl group, a nitro group, CN, a halogen atom, a hydroxyl group or a carboxyl group,
  • the alkyl part of the group represented by R 111 , R 112 , R 113 , R 121 , R 122 , R 123 and R 124 may have a branched side chain or a cyclic alkyl.
  • R 103 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, or a heterocyclic ring-containing group having 2 to 20 carbon atoms.
  • the alkyl part of the group represented by R 103 may have a branched side chain or may be a cyclic alkyl, and R 103 and R 107 , R 103 and R 108 , R 104 and R 105 , R 105 and R 106 and R 106 and R 107 may be combined to form a ring, Hydrogen atoms in the group represented by R 103 may further R 121, OR 121, COR 121 , SR 121, NR 122 R 123, CONR 122 R 123, -NR 122 -OR 123, -NCOR 122 -OCOR 123, NR 122 COR 121 , OCOR 121 , COOR 121 , SCOR 121 , OCSR 121 , COSR 121 , CSOR 121 , hydroxyl group, nitro group, CN, halogen atom, or COOR 121 may be substituted, R 104 , R 105 , R 106 and R
  • photoradical polymerization initiators (D) include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (cyclopentadienyl) -bis [2,6-difluoro-3- (py-1-yl) )] Titanium and the like.
  • photo radical polymerization initiators (D) can be used alone or in combination of two or more according to the desired performance.
  • the radical photopolymerization initiator (D) as described above is preferably 0.01 to 10% by mass, particularly preferably 0.1 to 1% by mass in the photosensitive composition of the present invention.
  • the content of the photo radical polymerization initiator is less than 0.01% by mass, curing by exposure may be insufficient.
  • the photo radical polymerization initiator is contained in the photosensitive composition. It may precipitate.
  • a coloring agent may be further added to the photosensitive composition to obtain a colored photosensitive composition.
  • the cured product of the colored photosensitive composition is suitably used as a color filter.
  • the addition amount of the colorant is preferably 0.01 to 50% by mass, and more preferably 0.1 to 30% by mass. When the addition amount of the colorant is less than 0.01% by mass, the color is insufficient, and when it is greater than 50% by mass, the colorant may precipitate in the photosensitive composition.
  • the colorant examples include dyes and pigments.
  • the dye is not particularly limited as long as it is a compound having absorption at 380 to 1200 nm.
  • inorganic pigments or organic pigments can be used.
  • inorganic pigment or organic pigment commercially available pigments can also be used.
  • the water resistance and heat resistance can be improved by adding a crosslinking agent to the photosensitive composition of the present invention and reacting with the hydrophilic group of the polymer.
  • the crosslinking agent include polyoxazoline compounds, carbodiimide compounds, epoxy compounds, polyamines, polyols, dicyandiamide derivatives, hydrazine compounds, polyhydrazide compounds (dihydrazide, trihydrazide), aldehydes, methylol compounds, activated vinyl compounds, poly Isocyanate compounds, alkylene carbonate compounds of phenol compounds, polyvalent metal salts, silane coupling agents, organic titanium, etc.
  • polyoxazoline compounds and carbodiimide compounds react at a heat drying temperature of 100 to 120 ° C. preferable.
  • cross-linking agent Commercially available products may be used as the cross-linking agent.
  • Epocros WS-300, WS-500, WS-700 manufactured by Nippon Shokubai Co., Ltd.
  • Carbodilite V-02, V-02-L2, SV-02, And V-04, V-10, SW-12G, E-02, E-03A, E-05 manufactured by Nisshinbo.
  • a solvent can be added to the photosensitive composition and the colored photosensitive composition.
  • the solvent is usually a solvent that can dissolve or disperse each of the above components as necessary, for example, methyl ethyl ketone, methyl amyl ketone, diethyl ketone, acetone, methyl isopropyl ketone, methyl isobutyl ketone, cyclohexanone, 2-heptanone, etc.
  • Ketones such as ethyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane, dipropylene glycol dimethyl ether; methyl acetate, ethyl acetate, acetic acid-n-propyl, isopropyl acetate Ester solvents such as n-butyl acetate, cyclohexyl acetate, ethyl lactate, dimethyl succinate, and texanol; cellosolv solvents such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; methanol Alcohol solvents such as ethanol, iso- or n-propanol, iso- or n-butanol, amyl alcohol, diacetone alcohol; ethylene glycol monomethyl acetate, ethylene glycol monoethyl acetate, propylene glycol-1-monomethyl ether-2-a
  • ketones, ether ester solvents, etc. particularly propylene glycol-1-monomethyl ether-2-acetate, cyclohexanone, and the like are preferable because the compatibility of the resist and the radical photopolymerization initiator is good in the photosensitive composition.
  • the above-mentioned colored photosensitive composition can further contain an inorganic compound.
  • the inorganic compound include metal oxides such as nickel oxide, iron oxide, iridium oxide, titanium oxide, zinc oxide, magnesium oxide, calcium oxide, potassium oxide, silica, and alumina; lamellar clay mineral, miloli blue, calcium carbonate, Magnesium carbonate, cobalt, manganese, glass powder, mica, talc, kaolin, ferrocyanide, various metal sulfates, sulfides, selenides, aluminum silicate, calcium silicate, aluminum hydroxide, platinum, gold, silver, copper Etc.
  • a dispersant can be added.
  • any colorant or inorganic compound can be used as long as it can disperse and stabilize, and commercially available dispersants such as BYK series manufactured by BYK Chemie can be used, and polyester having a basic functional group, Polymer dispersant made of polyether, polyurethane, having a nitrogen atom as a basic functional group, the functional group having a nitrogen atom is an amine and / or a quaternary salt thereof, and an amine value of 1 to 100 mgKOH / g Those are preferably used.
  • the colored photosensitive composition includes, if necessary, thermal polymerization inhibitors such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine; plasticizer; adhesion promoter; filler; Agents; leveling agents; surface conditioning agents; antioxidants such as phenolic antioxidants, phosphite antioxidants, thioether antioxidants; UV absorbers; dispersion aids; aggregation inhibitors; catalysts; Conventional additives such as thickeners can be added.
  • thermal polymerization inhibitors such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, phenothiazine
  • plasticizer adhesion promoter
  • filler Agents; leveling agents; surface conditioning agents; antioxidants such as phenolic antioxidants, phosphite antioxidants, thioether antioxidants; UV absorbers; dispersion aids; aggregation inhibitors; catalysts; Conventional additives such as
  • the properties of the cured product of the colored photosensitive composition of the present invention can be improved.
  • the organic polymer include polystyrene, polymethyl methacrylate, methyl methacrylate-ethyl acrylate copolymer, poly (meth) acrylic acid, styrene- (meth) acrylic acid copolymer, (meth) acrylic acid-methyl methacrylate.
  • Copolymer ethylene-vinyl chloride copolymer, ethylene-vinyl copolymer, polyvinyl chloride resin, ABS resin, nylon 6, nylon 66, nylon 12, urethane resin, polycarbonate polyvinyl butyral, cellulose ester, polyacrylamide, saturated Polyester, phenolic resin, phenoxy resin, polyamideimide resin, polyamic acid resin, epoxy resin, and the like.
  • polystyrene, (meth) acrylic acid-methyl methacrylate copolymer, and epoxy resin are included. Masui.
  • a chain transfer agent a sensitizer, a surfactant, a silane coupling agent, melamine and the like can be used in combination with the colored photosensitive composition.
  • a sulfur atom-containing compound is generally used.
  • Alkyl compounds trimethylolpropane tris (3-mercaptoisobutyrate), butanediol bis (3-mercaptoisobutyrate), hexanedithiol, decanedithiol, 1,4- Methyl mercaptobenzene, butanediol bisthiopropionate, butanediol bisthioglycolate, ethylene glycol bisthioglycolate, trimethylolpropane tristhioglycolate, butanediol bisthiopropionate, trimethylolpropane tristhiopropionate , Trimethylolpropane tristhioglycolate, pentaerythritol tetrakisthiopropionate, pentaerythritol tetrakisthioglycolate, trishydroxyethyl tristhiopropionate, the following compound no. C1, aliphatic polyfunctional thiol
  • the surfactant examples include fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates, anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates, and higher amines. Cationic surfactants such as halogenates and quaternary ammonium salts, nonionic surfactants such as polyethylene glycol alkyl ethers, polyethylene glycol fatty acid esters, sorbitan fatty acid esters and fatty acid monoglycerides, amphoteric surfactants, silicone surfactants Surfactants such as agents can be used, and these may be used in combination.
  • fluorine surfactants such as perfluoroalkyl phosphates and perfluoroalkyl carboxylates
  • anionic surfactants such as higher fatty acid alkali salts, alkyl sulfonates, and alkyl sulfates,
  • silane coupling agent for example, a silane coupling agent manufactured by Shin-Etsu Chemical Co., Ltd. can be used. Among them, KBE-9007, KBM-502, KBE-403 and the like, silane cups having an isocyanate group, a methacryloyl group, and an epoxy group. A ring agent is preferably used.
  • Examples of the melamine compound include all or part of active methylol groups (CH 2 OH groups) in nitrogen compounds such as (poly) methylol melamine, (poly) methylol glycoluril, (poly) methylol benzoguanamine, and (poly) methylol urea. Mention may be made of compounds in which (at least two) are alkyl etherified.
  • examples of the alkyl group constituting the alkyl ether include a methyl group, an ethyl group, and a butyl group, which may be the same as or different from each other.
  • methylol groups that are not alkyletherified may be self-condensed within one molecule, and may be condensed between two molecules, resulting in the formation of an oligomer component.
  • hexamethoxymethyl melamine, hexabutoxymethyl melamine, tetramethoxymethyl glycoluril, tetrabutoxymethyl glycoluril and the like can be used.
  • alkyl etherified melamines such as hexamethoxymethyl melamine and hexabutoxymethyl melamine are preferable.
  • the photosensitive composition and the colored photosensitive composition are prepared by known means such as spin coater, roll coater, bar coater, die coater, curtain coater, various printing, dipping, soda glass, quartz glass, semiconductor substrate, metal. It can be applied on a supporting substrate such as paper or plastic. Moreover, after once applying on support bases, such as a film, it can also transfer on another support base
  • the active energy ray light source used for curing the photosensitive composition and the colored photosensitive composition those that emit light having a wavelength of 300 to 450 nm can be used.
  • Mercury vapor arc, carbon arc, xenon arc, etc. can be used.
  • the laser direct drawing method that directly forms an image from digital information such as a computer without using a mask improves not only productivity but also resolution and positional accuracy.
  • the laser beam light having a wavelength of 340 to 430 nm is preferably used, but an argon ion laser, a helium neon laser, a YAG laser, a semiconductor laser, etc. are visible to infrared region. Those that emit light are also used. When these lasers are used, a sensitizing dye that absorbs the region from visible to infrared is added.
  • the photosensitive composition and the colored photosensitive composition of the present invention can also be patterned through a double patterning process in which patterning is performed twice using two photosensitive compositions or colored photosensitive compositions.
  • the photosensitive composition and the colored photosensitive composition of the present invention can be temporarily cured by irradiating the active energy ray and further cured by heating.
  • the pattern can be formed by heating after irradiating the active energy ray, developing, and heating.
  • the photosensitive composition and the colored photosensitive composition are photocurable paints or varnishes, photocurable adhesives, printed boards, color televisions, PC monitors, portable information terminals, digital cameras, etc.
  • the photosensitive composition of the present invention can be used for a transparent conductive film, a reflective film, a polarizing plate, a protective film, etc., and is applied through a mask having a predetermined pattern shape by sequentially applying each of the above-described layers to a transparent substrate. It can be used as a transparent laminate obtained by irradiating light, developing the exposed film with a developer, and heating the developed film.
  • a transparent base material in which transparent thin film layers and metal thin film layers made of a composite oxide of indium oxide and cerium oxide are alternately arranged can be used.
  • a photosensitive composition containing the compound of the present invention as a latent additive may be used for each of the aforementioned layers, or the photosensitive composition may be used for any one or more layers.
  • the transparent laminate is suitably used for a display device.
  • the colored photosensitive composition is used for the purpose of forming pixels of a color filter, and is particularly useful as a photosensitive composition for forming a color filter for a display device for an image display device such as a liquid crystal display panel.
  • the color filter for a display device includes (1) a step of forming a coating film of the colored photosensitive composition on a substrate, and (2) irradiating the coating film with active light through a mask having a predetermined pattern shape. It is preferably formed by a step, (3) a step of developing the film after exposure with a developer, and (4) a step of heating the film after development.
  • the colored photosensitive composition of the present invention is also useful as an inkjet colored photosensitive composition having no development step.
  • a multi-tone mask such as a halftone mask or a gray scale mask can be used.
  • reaction solution was cooled to room temperature, 160 g of PGMEA, 59 g of biphthalic anhydride and 0.24 g of tetra-n-butylammonium bromide were added, and the mixture was stirred at 120 ° C. for 4 hours. Further, 20 g of tetrahydrophthalic anhydride was added, and after stirring at 120 ° C. for 4 hours, at 100 ° C. for 3 hours, at 80 ° C. for 4 hours, at 60 ° C. for 6 hours, and at 40 ° C.
  • Photosensitive composition No. 1-No. 11 and comparative photosensitive composition no. 1-No. Preparation of photosensitive composition No. 2 in accordance with the formulation of [Table 1] and [Table 2].
  • 1-No. 11 and comparative photosensitive composition no. 1-No. 2 was prepared. The numerical values in [Table 1] and [Table 2] are parts by mass.
  • A-1 to A-4 in [Table 1] and [Table 2] represent the following latent additives.
  • B-1 to B-4, B'-1, C-1 to C-2, D-1 to D-3, E-1 and F-1 in [Table 1] and [Table 2] are respectively The following compounds are represented.
  • B-1 SPC-1000 (Acrylic resin from Showa Denko; weight average molecular weight 31980, double bond equivalent 900)
  • B-2 SPC-3000 (Acrylic resin from Showa Denko; weight average molecular weight 7610, double bond equivalent 340)
  • B-3 Obtained in Production Example 1 (weight average molecular weight 22000, double bond equivalent 330)
  • B-4 Obtained in Production Example 2 (weight average molecular weight 5600, double bond equivalent 434)
  • B′-1 SPC-2000 Showa Denko acryl resin; weight average molecular weight 17500, double bond equivalent 0)
  • C-1 Aronix M450 (Toagosei Co., Ltd.
  • the photosensitive composition of the present invention is maintained with high transparency after firing, that is, it has high heat resistance and excellent solvent resistance.
  • the photosensitive composition which gives the hardened

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