WO2017170183A1 - 組成物及び新規化合物 - Google Patents

組成物及び新規化合物 Download PDF

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WO2017170183A1
WO2017170183A1 PCT/JP2017/011886 JP2017011886W WO2017170183A1 WO 2017170183 A1 WO2017170183 A1 WO 2017170183A1 JP 2017011886 W JP2017011886 W JP 2017011886W WO 2017170183 A1 WO2017170183 A1 WO 2017170183A1
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group
carbon atoms
substituent
general formula
represented
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PCT/JP2017/011886
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English (en)
French (fr)
Japanese (ja)
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依純 松井
木村　正樹
鈴木　智美
光裕 岡田
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株式会社Adeka
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Priority to JP2018509215A priority Critical patent/JP6875376B2/ja
Priority to CN201780006082.2A priority patent/CN108699183A/zh
Priority to KR1020187016787A priority patent/KR102314688B1/ko
Publication of WO2017170183A1 publication Critical patent/WO2017170183A1/ja

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/005—Stabilisers against oxidation, heat, light, ozone
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/18—Benzotriazoles
    • C07D249/20—Benzotriazoles with aryl radicals directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
    • C07D493/20—Spiro-condensed systems
    • 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
    • C08F16/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical
    • C08F16/12—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal or ketal radical by an ether radical
    • C08F16/32—Monomers containing two or more unsaturated aliphatic radicals
    • 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
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133514—Colour filters
    • 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
    • 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 relates to a composition containing a compound having a specific structure, which is inactive at room temperature, and which is activated by heating to a predetermined temperature and exhibits a function, and a novel compound. Furthermore, the present invention relates to a colored photosensitive composition obtained by adding a colorant to the composition, and a color filter using the colored photosensitive composition.
  • Patent Documents 1 to 4 In order to improve the weather resistance and heat resistance of the photosensitive composition, a method of stabilizing by adding an ultraviolet absorber or an antioxidant is known (Patent Documents 1 to 4).
  • Phenolic antioxidants and UV absorbers have the effect of trapping radicals that greatly affect the deterioration of the polymer, so adding them into the polymerization system generally acts as a so-called polymerization inhibitor and inhibits curing. Therefore, latent additives have been developed (Patent Document 5).
  • a composition using a conventional latent additive has a large amount of outgas, so that there is a problem that the heating device is contaminated or the physical properties of the composition are lowered. There are problems of contamination of equipment and reduction of physical properties.
  • the composition using the conventional latent additive has a problem that the cured product has low solvent resistance, and thus the cured product is eluted, and the luminance of the color filter is lowered, for example.
  • an object of the present invention is to use a compound that is inactive at normal temperature and activated by heating to a predetermined temperature and that exhibits a function as an antioxidant or an ultraviolet absorber, and has a low outgas.
  • the object is to provide a composition having high solvent resistance, particularly a photosensitive composition.
  • Another object of the present invention is to provide a colored composition obtained by adding a colorant to the above composition, particularly a colored photosensitive composition suitable for a color filter.
  • a composition using a compound having a specific protecting group has less outgas, and the cured product has high solvent resistance. It has been found that a coloring composition obtained by adding a colorant to a coloring composition, particularly a colored photosensitive composition, is suitable for a color filter for an image display device such as a liquid crystal display panel without reducing the luminance of an optical filter (particularly a color filter). And the present invention has been reached.
  • the present invention has been made based on the above findings, and provides a composition containing a compound having a substituent represented by the following general formula (I).
  • R 1 and R 2 are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, or an alkyl having 1 to 40 carbon atoms which may have a substituent
  • An aryl group having 6 to 20 carbon atoms which may have a substituent, an arylalkyl group having 7 to 20 carbon atoms which may have a substituent, or a substituent In some cases represents a C2-C20 heterocyclic-containing group or a trialkylsilyl group
  • the methylene group in the alkyl group or arylalkyl group represented by R 1 and R 2 is —O—, —S—, —CO—, —O—CO—, —CO—O—, —O—CO—.
  • R' is a hydrogen atom or a carbon atom Represents an alkyl group of 1 to 8, j represents a number from 1 to 3, * Means that it is bonded to an adjacent group at the * part. )
  • composition of the present invention contains a compound having a substituent represented by the above general formula (I).
  • n represents an integer of 1 to 10
  • X 1 represents an n-valent linking group
  • R 1 , R 2 and j are the same as in the general formula (I).
  • Examples of the halogen atom represented by R 1 and R 2 include fluorine, chlorine, bromine and iodine.
  • Examples of the alkyl group having 1 to 40 carbon atoms represented by R 1 and R 2 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,
  • Examples of the arylalkyl group having 7 to 20 carbon atoms represented by R 1 and R 2 include benzyl, 1-methyl-1-phenylethyl, 1-naphthylmethyl, 9-anthracenylmethyl, 9-fluorenyl, 3 -Phenylpropyl, methyl-2-phenylpropan-2-yl, diphenylmethyl, triphenylmethyl, phenethyl, styryl, cinnamyl and the like,
  • Examples of the heterocyclic group containing 2 to 20 carbon atoms represented by R 1 and R 2 include a pyridine ring, a pyrimidine ring, a pyridazine ring, a piperidine ring, a pyran ring, a pyrazoline ring, a triazine ring, a pyrroline ring, a quinoline ring, Isoquinoline ring, imidazoline ring, benzimi
  • alkyl group having 1 to 8 carbon atoms represented by R ′ examples include those satisfying a predetermined number of carbon atoms among the above alkyl groups represented by R 1 . Containing an alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or a heterocyclic ring having 2 to 20 carbon atoms represented by R 1 and R 2 Substituents for substituting groups include ethylenically unsaturated groups such as vinyl, allyl, acryl and methacryl; halogen atoms such as fluorine, chlorine, bromine and iodine; acetyl, 2-chloroacetyl, propionyl, octanoyl, acryloyl and methacryloyl Acyl groups such as phenylcarbonyl (benzoyl), phthaloyl, 4-trifluoro
  • R 1 and R 2 a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, and an aryl group having 6 to 12 carbon atoms are preferable because of less outgassing. It is more preferable that R 1 is a branched alkyl group having 1 to 8 carbon atoms, particularly a t-butyl group, and R 2 is a hydrogen atom because outgas is particularly small.
  • X 1 represents an n-valent linking group. Specifically, for example, a direct bond, a hydrogen atom, a nitrogen atom, an oxygen atom, a sulfur atom, a phosphorus atom, the following (I -a) or (I-b), a group represented by, -CO -, - NH-CO -, - CO-NH -, - NR 3 -, - oR 3, -SR 3, -NR 3 R 4, Or an aliphatic hydrocarbon group having 1 to 120 carbon atoms which may have a substituent having the same valence as n, and 6 to 35 carbon atoms which may have a substituent.
  • R 3 and R 4 have a hydrogen atom or a substituent.
  • An aromatic ring-containing hydrocarbon group or a heterocyclic ring-containing group having 2 to 35 carbon atoms which may have a substituent, an aliphatic hydrocarbon group, an aromatic ring-containing hydrocarbon group and a heterocyclic ring-containing group, —O—, —S—, —CO—, —O—CO—, —CO—O—, —O—CO—O—, —S—CO—, —CO—S—, —S—CO—O.
  • -, -O-CO-S-, -CO-NH-, -NH-CO-, -NH-CO-O-, -O-CO-NH-, -NR'-, -SS-,- It may be replaced by a group selected from SO 2 — or a nitrogen atom.
  • n is 3
  • X 1 is an oxygen atom or a sulfur atom, —CO— , —NH—CO—, —CO—NH— or —NR 3 —
  • n is 2
  • X 1 is a hydrogen atom, —OR 3 , —SR 3 or —NR 3 R 4 , n is 1 and X 1 may form a ring together with the benzene ring.
  • the n groups are the same or different from each other.
  • the value of n is 1 to 10, and preferably 2 to 6 from the viewpoint of ease of synthesis.
  • the aliphatic hydrocarbon group having 1 to 120 carbon atoms which may have a substituent, which is represented by X 1 and has the same valence as n includes n Are monovalent, for example, methyl, ethyl, propyl, isopropyl, cyclopropyl, butyl, sec-butyl, tert-butyl, isobutyl, amyl, isoamyl, tert-amyl, cyclopentyl, hexyl, 2-hexyl, 3- Alkyl such as hexyl, cyclohexyl, bicyclohexyl, 1-methylcyclohexyl, heptyl, 2-heptyl, 3-heptyl, isoheptyl, tertiary heptyl, n-octyl, isooctyl, tertiary octyl, 2-ethylhe
  • Examples of the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms, which may have a substituent having the same valence as n are those in which n is monovalent, such as benzyl, phenethyl, diphenylmethyl, Arylalkyl groups such as triphenylmethyl, styryl and cinnamyl; aryl groups such as phenyl and naphthyl; aryloxy groups such as phenoxy and naphthyloxy; arylthio groups such as phenylthio and naphthylthio; and these groups are substituted by substituents described later Group, etc.
  • n 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; A group in which the group is substituted by a substituent described later,
  • trivalent n include phenyl-1,3,5-trimethylene and the like, and groups in which these groups are substituted with a substituent described later.
  • the heterocycle-containing group having 2 to 35 carbon atoms that may have a substituent having the same number of valences as n includes those in which n is monovalent, pyridyl, pyrimidyl, pyridazyl, piperidyl, pyranyl , Pyrazolyl, triazyl, pyrrolyl, quinolyl, isoquinolyl, imidazolyl, benzimidazolyl, 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, 2,4-dioxyo
  • Examples of the aliphatic hydrocarbon group having 1 to 35 carbon atoms which may have a substituent represented by R 3 and R 4 include the aliphatic hydrocarbon group represented by X 1 and the aliphatic hydrocarbon group. Among combinations of group hydrocarbon groups and substituents described later, those satisfying a predetermined number of carbon atoms are mentioned,
  • Examples of the heterocyclic ring-containing group include 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 the above X 1 and these groups and substituents described later.
  • substituents include ethylenically unsaturated groups such as vinyl, allyl, acryl and methacryl; halogen atoms such as fluorine, chlorine, bromine and iodine; acetyl, 2-chloroacetyl, propionyl, octanoyl, acryloyl, methacryloyl and phenylcarbonyl ( Benzoyl), phthaloyl, 4-trifluoromethylbenzoyl, pivaloyl, salicyloyl, oxaloyl, stearoyl, methoxycarbonyl, ethoxycarbonyl, t-butoxycarbonyl, n-octadecyloxycarbonyl, carbamoyl, etc .; acetyloxy, benzoyloxy, etc.
  • X 1 when n is 2 to 6, X 1 can also be represented by the following general formulas (1) to (5), respectively.
  • Y 1 represents a single bond, —CR 5 R 6 —, —NR 7 —, a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, or 6 to 35 carbon atoms.
  • the aliphatic hydrocarbon group has —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO—, or an oxygen atom.
  • Z 1 and Z 2 are each independently a direct bond, —O—, —S—, —CO—, —CO—O—, —O—CO—, —SO 2 —, —SS—, —SO—.
  • -NR 6 -or -PR 6- R 5 , R 6 and R 7 may each independently have a hydrogen atom, a substituent, or an aliphatic hydrocarbon group having 1 to 35 carbon atoms or a substituent. Represents an aromatic hydrocarbon group having 6 to 35 carbon atoms or a heterocyclic group having 2 to 35 carbon atoms which may have a substituent, * Means that it is bonded to an adjacent group at the * part. )
  • R 8 represents a hydrogen atom, a phenyl group which may have a substituent, or a cycloalkyl group having 3 to 10 carbon atoms
  • R 9 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 are substituents.
  • May have f is an integer from 0 to 5, * Means that it is bonded to an adjacent group at the * part.
  • R 10 and R 11 are each independently an alkyl group having 1 to 10 carbon atoms which may have a substituent, or a carbon atom having 6 substituents 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 10 may form a ring with adjacent R 10 , p
  • Y 11 represents a trivalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, an alicyclic hydrocarbon group having 3 to 35 carbon atoms, or 6 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—
  • R 12 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 aliphatic hydrocarbon group is adjacent to —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO—, or an oxygen atom. May be replaced with a combination of these without any * Means that it is bonded to an adjacent group at the * part. )
  • Y 12 represents a carbon atom, a tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic hydrocarbon group having 6 to 35 carbon atoms, or 2 carbon atoms. Represents ⁇ 35 heterocycle-containing groups,
  • the aliphatic hydrocarbon group has —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO—, or an oxygen atom.
  • 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), * Means that it is bonded to an adjacent group at the * part. )
  • Y 13 represents a pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a complex having 2 to 20 carbon atoms. Represents a ring-containing group, The aliphatic hydrocarbon group has —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO—, or an oxygen atom.
  • Z 1 to Z 5 are each independently a group in the same range as the group represented by Z 1 to Z 3 in the general formula (2), * Means that it is bonded to an adjacent group at the * part. )
  • Y 14 represents a hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an aromatic hydrocarbon group having 6 to 35 carbon atoms, or a complex having 2 to 35 carbon atoms. Represents a ring-containing group, The aliphatic hydrocarbon group has —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO—, or an oxygen atom.
  • 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), * Means that it is bonded to an adjacent group at the * part. )
  • the aliphatic hydrocarbon group having 1 to 35 carbon atoms, which may have a substituent, represented by R 5 , R 6 and R 7 includes the above general formula ( The monovalent aliphatic hydrocarbon group exemplified as the n-valent linking group represented by X 1 in IA), and the n valence represented by X 1 in the general formula (IA).
  • Examples of the aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms which may have a substituent represented by R 5 , R 6 and R 7 include X 1 in the above general formula (IA).
  • groups substituted by those exemplified as the substituents in the above those satisfying a predetermined number of carbon atoms, etc.
  • the heterocyclic group having 2 to 35 carbon atoms which may have a substituent represented by R 5 , R 6 and R 7 is represented by X 1 in the above general formula (IA).
  • monovalent heterocycle-containing groups exemplified as the n-valent linking group, and these groups are exemplified as substituents of the group representing the n-valent bond represented by X 1 in the general formula (IA).
  • those substituted by the above those satisfying a predetermined number of carbon atoms can be mentioned.
  • the divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by Y 1 in the general formula (1) is an n represented by X 1 in the general formula (IA).
  • Examples of the divalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 1 include the divalent groups exemplified as the n-valent linking group represented by X 1 in the general formula (IA).
  • Examples of the divalent heterocyclic group having 2 to 35 carbon atoms represented by Y 1 include the divalent aromatic compounds exemplified as the n-valent linking group represented by X 1 in the general formula (IA). Of the ring-containing hydrocarbon groups and groups substituted by those exemplified as the substituents of the group representing the n-valent linking group represented by X 1 in the general formula (IA) And the like satisfying the number of carbon atoms.
  • examples of the cycloalkyl group having 3 to 10 carbon atoms represented by R 8 include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl and the like.
  • the alkyl group having 1 to 10 carbon atoms represented by R 9 satisfies the predetermined number of carbon atoms among the groups exemplified as the alkyl group having 1 to 40 carbon atoms represented by R 1 and R 2. Groups, etc.
  • Examples of the alkoxy group having 1 to 10 carbon atoms represented by R 9 include methyloxy, ethyloxy, propyloxy, isopropyloxy, butyloxy, sec-butyloxy, tert-butyloxy, isobutyloxy, amyloxy, isoamyloxy, tert-amyloxy Hexyloxy, cyclohexyloxy, heptyloxy, isoheptyloxy, tertiary heptyloxy, n-octyloxy, isooctyloxy, tertiary octyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy, etc.
  • the substituents of the phenyl group, cycloalkyl group, alkyl group, alkoxy group and alkenyl group are the same as those exemplified as the substituent of the n-valent linking group represented by X 1 in the general formula (IA). is there.
  • the alkyl group having 1 to 10 carbon atoms, which may have a substituent, represented by R 10 and R 11 includes R 1 and R 2 Among the groups exemplified as the alkyl group having 1 to 40 carbon atoms represented by the following: Examples of the aryl group having 6 to 20 carbon atoms which may have a substituent represented by R 10 and R 11 include an aryl group having 6 to 20 carbon atoms represented by R 1 and R 2 And the groups exemplified as Examples of the aryloxy group having 6 to 20 carbon atoms which may have a substituent represented by R 10 and R 11 include phenyloxy, naphthyloxy, 2-methylphenyloxy, 3-methylphenyloxy 4-methylphenyloxy, 4-vinylphenyldioxy, 3-iso-propylphenyloxy, 4-iso-propylphenyloxy, 4-butylphenyloxy, 4-tert-butylphenyloxy, 4-hex
  • arylthio group having 6 to 20 carbon atoms which may have a substituent represented by R 10 and R 11 is an arylthio group having 6 to 20 carbon atoms which may have the above-mentioned substituent.
  • the arylalkenyl group having 8 to 20 carbon atoms which may have a substituent, represented by R 10 and R 11 , may have 6 to 20 carbon atoms which may have the above-mentioned substituent.
  • Examples of the trivalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by Y 11 in the general formula (2) include an n-valent bond represented by X 1 in the general formula (IA).
  • 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.
  • Examples of the trivalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 11 include the trivalent groups exemplified as the n-valent linking group represented by X 1 in the general formula (IA). Of the aromatic ring-containing hydrocarbon group and a group in which these groups are substituted by those exemplified as the substituent of the n-valent linking group represented by X 1 in the general formula (IA). And those that satisfy the number of atoms.
  • Examples of the trivalent heterocyclic group having 2 to 35 carbon atoms represented by Y 11 include the trivalent complex exemplified as the n-valent linking group represented by X 1 in the general formula (IA).
  • the tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms represented by Y 12 in the general formula (3) is an n-valent aliphatic hydrocarbon group represented by X 1 in the general formula (IA).
  • X 1 n-valent aliphatic hydrocarbon group represented by X 1 in the general formula (IA).
  • Examples of the tetravalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 12 include the monovalent groups exemplified as the n-valent linking group represented by X 1 in the general formula (IA). To a trivalent aromatic ring-containing hydrocarbon group and a group in which these groups are substituted by those exemplified as the substituent of the n-valent linking group represented by X 1 in the general formula (IA).
  • Examples of the tetravalent heterocyclic group having 2 to 35 carbon atoms represented by Y 12 include monovalent to 3 exemplified as the n-valent linking group represented by X 1 in the general formula (IA).
  • a valent heterocyclic ring-containing group and a tetravalent group derived from these groups substituted by those exemplified as the substituent of the n-valent linking group represented by X 1 in the general formula (IA).
  • those satisfying a predetermined number of carbon atoms can be mentioned.
  • the pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms represented by Y 13 in the general formula (4) is an n-valent bond represented by X 1 in the general formula (IA).
  • the monovalent to trivalent aliphatic hydrocarbon groups exemplified as the groups and these groups are substituted by those exemplified as the substituents of the n-valent linking group represented by X 1 in the general formula (IA).
  • the pentavalent groups derived from these groups those satisfying a predetermined number of carbon atoms, etc.
  • the pentavalent aromatic group-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 14 is a monovalent group exemplified as the n-valent linking group represented by X 1 in the general formula (IA).
  • Examples of the pentavalent heterocyclic group having 2 to 35 carbon atoms represented by Y 14 include monovalent to 3 exemplified as the n-valent linking group represented by X 1 in the general formula (IA).
  • a valent heterocyclic ring-containing group and a pentavalent group derived from these groups substituted by those exemplified as the substituent of the n-valent linking group represented by X 1 in the general formula (IA).
  • the groups those satisfying a predetermined number of carbon atoms can be mentioned.
  • the hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms represented by Y 14 in the general formula (5) is an n-valent bond represented by X 1 in the general formula (IA).
  • the monovalent to trivalent aliphatic hydrocarbon groups exemplified as the groups and these groups are substituted by those exemplified as the substituents of the n-valent linking group represented by X 1 in the general formula (IA).
  • the hexavalent groups derived from these groups those satisfying a predetermined number of carbon atoms, etc.
  • the hexavalent aromatic ring-containing hydrocarbon group having 6 to 35 carbon atoms represented by Y 14 is a monovalent group exemplified as the n-valent linking group represented by X 1 in the general formula (IA).
  • X 1 n-valent linking group represented by X 1 in the general formula (IA)
  • Examples of the hexavalent heterocyclic group having 2 to 35 carbon atoms represented by Y 14 include monovalent to 3 exemplified as the n-valent linking group represented by X 1 in the general formula (IA).
  • the groups those satisfying a predetermined number of carbon atoms can be mentioned.
  • each of R 82 , R 83 and R 84 independently has a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, or a substituent, which may have 1 carbon atom.
  • R 92 and R 93 are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, or an alkyl group having 1 to 40 carbon atoms, which may have a substituent, Represents an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms or a heterocyclic ring-containing group having 2 to 20 carbon atoms, wherein R 1 and R 2 are the same as those in the above general formula (I) .)
  • R 201 , R 202 , R 203 , R 204 , R 205 , R 206 , R 207 , R 208 are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group,
  • Y 1 , Z 1 and Z 2 are the same as those in the general formula (1).
  • the halogen atom represented by R 82 , R 83 and R 84 an alkyl group having 1 to 40 carbon atoms which may have a substituent, 6 to 20 carbon atoms
  • the aryl group, the arylalkyl group having 7 to 20 carbon atoms, and the heterocycle-containing group having 2 to 20 carbon atoms those exemplified in the description of R 1 and R 2 in the general formula (I) can be given. .
  • Examples of the arylalkyl group having 7 to 20 carbon atoms and the heterocyclic ring-containing group having 2 to 20 carbon atoms include those exemplified in the description of R 1 and R 2 in the general formula (I).
  • Examples of the alkyl group having 1 to 40 atoms, the aryl group having 6 to 20 carbon atoms, the arylalkyl group having 7 to 20 carbon atoms, and the heterocyclic-containing group having 2 to 20 carbon atoms include those represented by the general formula (I). And those exemplified in the description of R 1 and R 2 in FIG.
  • R 1 is a branched alkyl group having 1 to 8 carbon atoms, particularly a t-butyl group, and R 2 is a hydrogen atom;
  • R 82 , R 83 and R 84 are each independently a hydrogen atom,
  • An alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an arylalkyl group having 7 to 12 carbon atoms, a heterocyclic-containing group having 1 to 10 carbon atoms, particularly R 82 , R 83 and R 84 are preferably an alkyl group having 1 to 4 carbon atoms or a heterocyclic ring-containing group having 1 to 10 carbon atoms.
  • R 1 is a branched alkyl group having 1 to 8 carbon atoms, particularly a t-butyl group, and R 2 is a hydrogen atom;
  • R 92 and R 93 are each independently a hydrogen atom or carbon atom number
  • An alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an arylalkyl group having 7 to 12 carbon atoms, a heterocyclic-containing group having 1 to 10 carbon atoms, particularly R 92 or R 93 Is preferably an alkyl group having 1 to 4 carbon atoms or a heterocyclic-containing group having 1 to 10 carbon atoms.
  • Y 1 is a sulfur atom, an alkylene group having 1 to 20 carbon atoms, a divalent aromatic ring-containing hydrocarbon group having 6 to 25 carbon atoms, or the number of carbon atoms.
  • divalent heterocyclic ring-containing groups divalent groups derived from 2,4,8,10-tetraoxaspiro [5,5] undecane, particularly alkylene groups having 1 to 15 carbon atoms
  • a divalent aromatic ring-containing hydrocarbon group having 6 to 15 carbon atoms and a divalent group derived from 2,4,8,10-tetraoxaspiro [5,5] undecane are preferred
  • Z 1 and Z 2 are a direct bond, —CO—O—, —O—CO—, an optionally substituted aliphatic hydrocarbon group having 1 to 20 carbon atoms, or 6 to 10 carbon atoms.
  • an aromatic hydrocarbon group particularly an aliphatic hydrocarbon group having 1 to 8 carbon atoms which may have a substituent
  • Y 11 is an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an arylalkyl group having 7 to 12 carbon atoms, or a carbon atom
  • Z 1 , Z 2 and Z 3 are preferably the same as Z 1 and Z 2
  • Y 12 is preferably a tetravalent group corresponding to the group listed above as preferred Y 11 , Z 1 to Z 4 are preferably
  • Preferred examples of the compound represented by the general formula (I) include compounds shown in the following [Chemical Formula 14] to [Chemical Formula 15], but are not limited to these compounds.
  • the production method of the compound having a substituent represented by the above general formula (I) is not particularly limited.
  • JP-A-57-111375, JP-A-3-173843, JP-A-6-128195, JP-A-6-128195 No. 7-206871, JP-A-7-252191, JP-A 2004-501128, and a phenol compound produced by the method described above and 1-chloro-3-methyl-2-butene are reacted. Obtainable.
  • the compound having a substituent represented by the general formula (I) can be used as a latent additive in various compositions.
  • the latent additive is inactive in a pre-bake process at room temperature or 150 ° C. or less, for example 150 ° C. or less, and is heated at 100 to 250 ° C. or at 80 to 200 ° C. in the presence of an acid / base catalyst. By heating, the protecting group is eliminated and becomes active.
  • the compound having a substituent represented by the above general formula (I) is a photosensitive composition, a photocurable composition, a thermosetting composition or a polymerizable composition as a latent antioxidant or a latent ultraviolet absorber. It can also be used for a heat sensitive material as a latent developer.
  • the composition of the present invention is the same as the conventional photosensitive composition, photocurable composition, thermosetting composition, and polymerization except that it contains a compound having a substituent represented by the above general formula (I). Composition.
  • the content of the compound having a substituent represented by the general formula (I) as a latent additive is 0.001 to 20% by mass in the solid content of the composition of the present invention. Is preferable, and 0.005 to 5 mass% is more preferable.
  • the composition of the present invention includes a compound having a substituent represented by the above general formula (I) as a latent antioxidant, a polymerizable compound having an ethylenically unsaturated bond having an acid value, and a photoradical It can be set as the photosensitive composition (henceforth the photosensitive composition of this invention) containing a polymerization initiator.
  • the polymerizable compound having an ethylenically unsaturated bond having an acid value include (meth) acrylic acid, ⁇ -chloroacrylic acid, itaconic acid, maleic acid, citraconic acid, fumaric acid, hymic acid, crotonic acid, and isocrotonic acid.
  • 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.
  • polymerizable compounds having an ethylenically unsaturated bond having an acid value can be used alone or in admixture of two or more, and are polymerizable having an ethylenically unsaturated bond having no acid value. It can be used in combination with a compound. When two or more kinds are mixed and used, they may be copolymerized in advance and used as a copolymer.
  • the content of the polymerizable compound having an ethylenically unsaturated bond having an acid value is preferably 20 to 80% by mass in the solid content of the composition of the present invention. More preferred is 30 to 70% by mass.
  • Examples of the polymerizable compound having an ethylenically unsaturated bond having no acid value include, for example, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, glycidyl (meth) acrylate, The following compound No. A1-No.
  • A4 methyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate, tert-butyl (meth) acrylate, cyclohexyl (meth) acrylate, n-octyl (meth) acrylate, ( Isooctyl (meth) acrylate, isononyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, methoxyethyl (meth) acrylate, dimethylaminomethyl (meth) acrylate, dimethyl (meth) acrylate Aminoethyl, aminopropyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, ethoxyethyl (meth) acrylate, poly (ethoxy) ethyl (meth) acrylate, butoxyethoxyethyl (
  • a monofunctional or polyfunctional epoxy compound can be used together with the polymerizable compound having an ethylenically unsaturated bond having the acid value.
  • the polymerizable compound having an ethylenically unsaturated bond having an acid value preferably has a solid content acid value of 5 to 120 mgKOH / g, and the amount of the monofunctional or polyfunctional epoxy compound used is It is preferable to select so as to satisfy the value.
  • Examples of the monofunctional epoxy compound include glycidyl methacrylate, methyl glycidyl ether, ethyl glycidyl ether, propyl glycidyl ether, isopropyl glycidyl ether, butyl glycidyl ether, isobutyl glycidyl ether, t-butyl glycidyl ether, pentyl glycidyl ether, hexyl glycidyl ether, heptyl Glycidyl ether, octyl glycidyl ether, nonyl glycidyl ether, decyl glycidyl ether, undecyl glycidyl ether, dodecyl glycidyl ether, tridecyl glycidyl ether, tetradecyl glycidyl ether, pentadecy
  • the polyfunctional epoxy compound it is preferable to use one or more selected from the group consisting of bisphenol-type epoxy compounds and glycidyl ethers because a photosensitive composition with better characteristics can be obtained.
  • the bisphenol type epoxy compound an epoxy compound represented by the above general formula (III) can be used, and for example, a bisphenol type epoxy compound such as a hydrogenated bisphenol type epoxy compound can also be used.
  • glycidyl ethers examples include ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1,4-butanediol diglycidyl ether, 1,6-hexanediol diglycidyl ether, 1,8-octanediol diglycidyl ether, 1 , 10-decanediol diglycidyl ether, 2,2-dimethyl-1,3-propanediol diglycidyl ether, diethylene glycol diglycidyl ether, triethylene glycol diglycidyl ether, tetraethylene glycol diglycidyl ether, hexaethylene glycol diglycidyl ether 1,4-cyclohexanedimethanol diglycidyl ether, 1,1,1-tri (glycidyloxymethyl) propane, 1,1,1-tri (g Glycidyl oxymethyl) ethane, 1,1,1-tri (g
  • novolac epoxy compounds such as phenol novolac epoxy compounds, biphenyl novolac epoxy compounds, cresol novolac epoxy compounds, bisphenol A novolac epoxy compounds, dicyclopentadiene novolac epoxy compounds; 3,4-epoxy-6-methyl Cycloaliphatic epoxy such as cyclohexylmethyl-3,4-epoxy-6-methylcyclohexanecarboxylate, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 1-epoxyethyl-3,4-epoxycyclohexane Compound: Glycidyl esters such as diglycidyl phthalate, diglycidyl tetrahydrophthalate, glycidyl dimer, tetraglycidyl diamino Glycidylamines such as phenylmethane, triglycidyl-p-aminophenol and N, N-diglycidylaniline; hetero
  • the photo radical polymerization initiator may be any compound that can initiate radical polymerization upon receiving light irradiation.
  • ketones such as acetophenone compounds, benzyl compounds, benzophenone compounds, thioxanthone compounds, etc.
  • preferred compounds include oxime 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 (IV) or (V) 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 combine with each other to form a ring, R 55 , R 56 , R 57 , R 58 , R 59 , R 60 , R 61 , R 62
  • alkyl groups 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 3 represents an oxygen atom, a sulfur atom, a selenium atom, CR 75 R 76 , CO, NR 77 or PR 78
  • X 4 represents a single bond or CO
  • R 75 to R 78 represent an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms, and methylene in the alkyl group or arylalkyl group
  • the group may be substituted with a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group or a heterocyclic group, or may be
  • 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 or halogen atom may be substituted, R 104 , R 105 , R 106 and R 107 are each independently R
  • radical photopolymerization initiators include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, bis (cyclopentadienyl) -bis [2,6-difluoro-3- (pyr-1-yl)] titanium Etc.
  • photo radical polymerization initiators can be used alone or in combination of two or more according to the desired performance.
  • the content of the radical photopolymerization initiator as described above is preferably 0.1 to 30% by mass, particularly preferably 0.5 to 10% by mass, based on the solid content of the photosensitive composition of the present invention.
  • the content of the photo radical polymerization initiator is less than 0.1% by mass, curing by exposure may be insufficient, and when it is greater than 30% by mass, the initiator is precipitated in the photosensitive composition. There is.
  • the photosensitive composition of the present invention can be made into a colored photosensitive composition by further adding a colorant.
  • the cured product of the colored photosensitive composition is suitably used as a color filter.
  • the content of the colorant is preferably 0.01 to 50% by mass, more preferably 0.1 to 30% by mass in the solid content of the colored photosensitive composition of the present invention. .
  • the content of the colorant is less than 0.01% by mass, desired chromaticity may not be obtained.
  • the colorant may be precipitated in the colored 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.
  • a solvent can be further added to the photosensitive composition and the colored photosensitive composition of the present invention.
  • 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.
  • a solvent it is preferable from the viewpoint of handling and the like that the solid content of the photosensitive composition or colored photosensitive composition of the present invention is 25 to 35% by mass.
  • the photosensitive composition and the colored photosensitive composition of the present invention 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.
  • the dispersant is not particularly limited as long as it can disperse and stabilize colorants and inorganic compounds, and commercially available dispersants such as BYK series manufactured by BYK Chemie can be used and have a basic functional group.
  • Polymer dispersant comprising polyester, 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 Are preferably used.
  • the photosensitive composition and the colored photosensitive composition of the present invention include, if necessary, thermal polymerization inhibitors such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, and phenothiazine; plasticizers; Agents; fillers; antifoaming agents; leveling agents; surface conditioning agents; antioxidants such as phenolic antioxidants, phosphite antioxidants, thioether antioxidants; UV absorbers; dispersion aids; Conventional additives such as an agent, a catalyst, an effect promoter, a cross-linking agent, and a thickener can be added.
  • thermal polymerization inhibitors such as p-anisole, hydroquinone, pyrocatechol, t-butylcatechol, and phenothiazine
  • plasticizers Agents
  • Fillers such as phenolic antioxidants, phosphite antioxidants, thioether antioxidants
  • UV absorbers such as phenolic antioxidants, phos
  • the characteristics of the cured product of the photosensitive composition of the present invention and the colored photosensitive composition are improved by using another organic polymer together with the polymerizable compound having an ethylenically unsaturated bond having the acid value.
  • 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, a melamine compound, and the like can be further used in combination.
  • 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 or different.
  • methylol groups that are not alkyl etherified may be self-condensed within one molecule or 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 colored photosensitive composition of the present invention are prepared by known means such as spin coater, roll coater, bar coater, die coater, curtain coater, various printing, dipping, soda glass, quartz glass, and semiconductor substrate. It can be applied on a supporting substrate such as metal, paper, and plastic. Moreover, after once applying on support bases, such as a film, it can also transfer on another support base
  • the active light source used for curing the photosensitive composition and the colored photosensitive composition of the present invention those capable of emitting 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 method of curing the photosensitive composition or colored photosensitive composition of the present invention is a known method such as spin coater, roll coater, bar coater, die coater, curtain coater, various printing, dipping, soda glass, It includes a step of forming a coating film on a supporting substrate such as quartz glass, semiconductor substrate, metal, paper, plastic, and the like, and a step of exposing the coating film to exposure and curing the active light.
  • the photosensitive composition and the colored photosensitive composition (or cured product thereof) of the present invention are a photocurable paint or varnish, an adhesive such as a photocurable adhesive, a printed circuit board, a color television, a PC monitor, or portable information.
  • Color filters for color display liquid crystal display panels such as terminals and digital cameras, color filters for CCD image sensors, photo spacers, black column spacers, electrode materials for plasma display panels, touch panels, touch sensors, powder coatings, printing inks, printing To produce plates, dental compositions, stereolithography resins, gel coats, photoresists for electronics, electroplating resists, etching resists, both liquid and dry films, solder resists, and color filters for various display applications Or plasma display panel, electroluminescent display, and LC Resist for forming structures in the manufacturing process, composition for encapsulating electrical and electronic components, solder resist, magnetic recording materials, micromechanical components, waveguide, optical switch, plating mask, etching mask, color test Systems, glass fiber cable coatings, stencils
  • the photosensitive composition of the present invention can be used as a transparent structure by curing.
  • transparent structures include columnars called photo spacers (PS) and column spacers (CS); fine patterns of (nano) imprints; production of large advertising signs, color filters for liquid crystal displays, and alignment films
  • PS photo spacers
  • CS column spacers
  • fine patterns of (nano) imprints production of large advertising signs, color filters for liquid crystal displays, and alignment films
  • Examples thereof include an ink jet receiving layer used for manufacturing electronic devices such as printing.
  • the transparent structure of the present invention is suitably used for display devices.
  • the photosensitive composition of the present invention can be used for a transparent conductive film, a reflective film, a polarizing plate, a protective film, and the like. Each desired layer is sequentially applied to a transparent base material, and a mask having a predetermined pattern shape is used. It can be used as a transparent laminate obtained by irradiating active light, developing the exposed film with a developer, and heating the developed film.
  • a transparent laminated body the thing etc. with which the transparent thin film layer and metal thin film layer which consist of a complex oxide of an indium oxide and a cerium oxide are alternated on the transparent base material are mentioned, for example.
  • the photosensitive composition of the present invention containing a compound having a substituent represented by the general formula (I) as a latent additive may be used for each of the above-described layers, and the photosensitive composition may be used for any of the layers.
  • a composition may be used.
  • the transparent laminate is suitably used for a display device.
  • the colored photosensitive composition of the present invention 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. is there.
  • the color filter for a display device includes (1) a step of forming a coating film of the colored photosensitive composition of the present invention on a substrate, and (2) active light through a mask having a predetermined pattern shape on the coating film.
  • the step of irradiating, (3) the step of developing the film after exposure with a developer, and (4) the step of heating the film after development are preferably formed.
  • the colored photosensitive composition of the present invention is also useful as an inkjet-type colored photosensitive composition without a development step.
  • a multi-tone mask such as a halftone mask or a gray scale mask can be used.
  • thermosetting composition as an example of the composition of the present invention will be described.
  • the thermosetting composition is cured by heating and may be any of a thermal cation curable composition, a thermal anion curable composition, or a thermal radical curable composition. Since a radical is trapped when the compound which has a substituent represented with general formula (I) as a latent antioxidant is heated and activated, it is preferable.
  • the thermal radical curable composition contains a compound having a substituent represented by the general formula (I) as a latent antioxidant, and also contains a radical polymerizable organic substance and a thermal radical polymerization initiator as essential components.
  • the radical polymerizable organic substance is a polymerizable compound having an ethylenically unsaturated bond, and specifically includes the compounds described in the above [0046] and [0049]. It is done.
  • the thermal radical polymerization initiator include 2,2′-azobisisobutyronitrile, 2,2′-azobis (methylisobutylate), 2,2′-azobis-2,4-dimethylvaleronitrile, Azo initiators such as 1′-azobis (1-acetoxy-1-phenylethane); benzoyl peroxide, di-t-butylbenzoyl peroxide, t-butylperoxypivalate, di (4-t-butylcyclohexyl) )
  • Peroxide initiators such as peroxydicarbonate, and persulfates such as ammonium persulfate, sodium persulfate, and potassium persulfate. These can be used alone or in combination of two or more.
  • thermosetting composition is dissolved or dispersed in an organic solvent as necessary, and the obtained coating liquid is a known spin coater, roll coater, bar coater, die coater, curtain coater, various printing, dipping, etc. By means, it can be applied on a support substrate such as soda glass, quartz glass, semiconductor substrate, metal, paper, plastic, etc., and cured by heating.
  • a support substrate such as soda glass, quartz glass, semiconductor substrate, metal, paper, plastic, etc.
  • the organic solvent is not particularly limited and known and commonly used ones can be used.
  • ketones, ethers, amides, alcohols and the like can be preferably used. Specific examples include acetone, methyl ethyl ketone, methyl- n-butyl ketone, methyl isobutyl ketone, ethyl isobutyl ketone, diethyl ether, tetrahydrofuran, dioxane, dimethylformamide, diethylformamide, dimethylacetamide, diethylacetamide, N-methylpyrrolidone, methanol, ethanol, isopropanol, ethylene glycol, propylene glycol, 2- Known solvents such as methoxy-2-propanol and tetraglyme can be used.
  • the above-mentioned heat curing is usually carried out at a temperature of about 60 ° C. or higher, preferably about 100 to 300 ° C. for about 10 seconds to 3 hours.
  • the novel compound of the present invention is represented by the following general formula (V), (VI) or (VII).
  • the following general formulas (V), (VI) and (VII) correspond to the general formulas (II-1), (II-2) and (II-3), respectively.
  • (VI) and (VII) the explanation of the corresponding variable groups in the general formulas (II-1), (II-2) and (II-3) and (I) is applied as appropriate. The same applies to points that are not particularly described.
  • R 31 , R 32 and R 33 are each independently a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, or a carbon atom which may have a substituent.
  • R 30 represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, a heterocyclic group having 2 to 20 carbon atoms, or Represents a trialkylsilyl group
  • the methylene group in the alkyl group or arylalkyl group represented by R 30 is —O—, —S—, —CO—, —O—CO—, —CO—O—, —O—CO—O—, -S-CO-, -CO-S-, -S-CO-O-, -O-CO-S-, -CO-NH-, -NH-CO-, -NH
  • R 33 and R 34 each independently represents a hydrogen atom, a halogen atom, a cyano group, a hydroxyl group, a nitro group, a carboxyl group, or an alkyl group having 1 to 40 carbon atoms, which may have a substituent
  • R 6 represents an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or a heterocyclic-containing group having 2 to 20 carbon atoms
  • R 30 is the same as in the general formula (V).
  • Y 20 represents a single bond, —CR 35 R 36 —, —NR 37 —, a divalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, or 6 to 35 carbon atoms.
  • the aliphatic hydrocarbon group has —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO—, or an oxygen atom.
  • Z 11 and Z 12 are each independently a direct bond, —O—, —S—, —CO—, —CO—O—, —O—CO—, —SO 2 —, —SS—, —SO—.
  • -NR 37 - or -PR 37 - represents, R 35 , R 36 and R 37 each independently have a hydrogen atom or a substituent, and may have a C 1-35 aliphatic hydrocarbon group or a substituent. Represents an aromatic hydrocarbon group having 6 to 35 carbon atoms or a heterocyclic group having 2 to 35 carbon atoms which may have a substituent, * Means that it is bonded to an adjacent group at the * part. )
  • R 117 represents a hydrogen atom, a phenyl group which may have a substituent, or a cycloalkyl group having 3 to 10 carbon atoms
  • R 118 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 are substituents.
  • May have j is an integer from 0 to 5, * Means that it is bonded to an adjacent group at the * part.
  • R 119 and R 120 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 119 may form a ring with adjacent R 119 , s represents
  • Y 21 represents a trivalent aliphatic hydrocarbon group having 3 to 35 carbon atoms, an alicyclic hydrocarbon group having 3 to 35 carbon atoms, or 6 to 35 carbon atoms.
  • Z 11 , Z 12 and Z 13 are each independently a direct bond, —O—, —S—, —CO—, —CO—O—, —O—CO—, —SO 2 —, —SS—,
  • R 111 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 aliphatic hydrocarbon group is adjacent to —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO—, or an oxygen atom. May be replaced with a combination of these without any * Means that it is bonded to an adjacent group at the * part. )
  • Y 22 represents a carbon atom, a tetravalent aliphatic hydrocarbon group having 1 to 35 carbon atoms, an aromatic hydrocarbon group having 6 to 35 carbon atoms, or 2 carbon atoms. Represents ⁇ 35 heterocycle-containing groups,
  • the aliphatic hydrocarbon group has —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO—, or an oxygen atom.
  • Z 11 to Z 14 are each independently a group within the same range as the group represented by Z 11 to Z 13 in the general formula (12), * Means that it is bonded to an adjacent group at the * part. )
  • Y 23 represents a pentavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a complex having 2 to 20 carbon atoms. Represents a ring-containing group, The aliphatic hydrocarbon group has —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO—, or an oxygen atom.
  • Z 11 to Z 15 are each independently a group in the same range as the group represented by Z 11 to Z 13 in the general formula (12), * Means that it is bonded to an adjacent group at the * part. )
  • Y 24 represents a hexavalent aliphatic hydrocarbon group having 2 to 35 carbon atoms, an aromatic hydrocarbon group having 6 to 35 carbon atoms, or a complex having 2 to 35 carbon atoms. Represents a ring-containing group, The aliphatic hydrocarbon group has —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO—, or an oxygen atom.
  • Z 11 to Z 16 are each independently a group within the same range as the group represented by Z 11 to Z 13 in the general formula (12), and * is a * moiety and is bonded to an adjacent group. Means. )
  • R 61 , R 62 , R 63 , R 64 , R 65 , R 66 , R 67 , R 68 are each independently a hydrogen atom, halogen atom, cyano group, hydroxyl group, nitro group, carboxyl group, An alkyl group having 1 to 40 carbon atoms, an aryl group having 6 to 20 carbon atoms, an arylalkyl group having 7 to 20 carbon atoms, or a heterocyclic ring having 2 to 20 carbon atoms, which may have a substituent Represents a containing group, and Y 20 , Z 11 and Z 12 are the same as those in the general formula (11).
  • novel compounds of the present invention represented by the general formulas (V) and (VI), those in which R 1 is a branched alkyl group having 1 to 8 carbon atoms, particularly a t-butyl group, It is more preferable because it is less.
  • the production method of the novel compound of the present invention is not particularly limited. And a phenolic compound produced by the method described in each publication of JP-A-2004-501128 and 1-chloro-3-methyl-2-butene.
  • novel compound of the present invention can be used as a latent antioxidant, a latent ultraviolet absorber, a dissolution regulator and the like.
  • Example 1-1 Compound No. Synthesis of 2 to 6
  • the following compound No. instead of the phenol compound of 1 ′, the following compound No.
  • the target compound No. 2 was prepared in the same manner as in Example 1-1, except that 2 ′ to 6 ′ phenolic compounds were used. 2-6 were synthesized. It was confirmed by 1 H-NMR and IR that the obtained solid was the desired product. The results are shown in [Table 1] to [Table 2].
  • Photosensitive composition No. 1 and comparative photosensitive composition No. 1 1-No. Preparation of 3 SPC-1000 (manufactured by Showa Denko KK, PGMEA solution with a solid content of 29%) 50.0 g, Aronix M-450 (manufactured by Toagosei), 11.6 g, NCI-930 (manufactured by ADEKA) 0.3 g, 34.7 g of PGMEA, 2.9 g of FZ2122 (manufactured by Toray Dow Corning Co., Ltd., PGMEA solution with a solid content of 1%) and 0.81 g of the compound described in [Table 3] are mixed, and stirred until insoluble matter is eliminated, and photosensitive composition Item No. 1 and comparative photosensitive composition No. 1 1-No. 3 was obtained.
  • Example 2-1 and Comparative Evaluation Examples 2-1 and 2-2 Solvent Resistance Evaluation
  • the photosensitive composition No. obtained in Example 2-1 was used.
  • Comparative photosensitive composition Nos. 1 and 2 obtained in Comparative Examples 2-1 and 2-2. 1-No. 2 were each applied to a glass substrate under conditions of 410 rpm ⁇ 7 seconds and dried on a hot plate (90 ° C. ⁇ 90 seconds).
  • the obtained coating film was exposed (40 mJ / cm 2 ) with an ultrahigh pressure mercury lamp.
  • the exposed coating film was baked under conditions of 230 ° C. ⁇ 30 minutes.
  • the film thickness of the obtained coating film After measuring the film thickness of the obtained coating film, it was immersed in PGMEA, cyclohexanone, N-methylpyrrolidone, and N-ethylpyrrolidone at room temperature for 30 minutes, and the film thickness after immersion was measured. It was evaluated that the solvent resistance was higher as the film thickness ratio before and after immersion (film thickness after immersion ⁇ 100 / film thickness before immersion) was closer to 100%.
  • the photosensitive composition of the present invention using a specific compound as a latent additive has less outgas and the cured product is excellent in solvent resistance.
  • the present invention there is little outgassing and a solvent resistance of a cured product using a compound that is inactive at room temperature and activated by heating to a predetermined temperature and exhibits a function as an antioxidant or an ultraviolet absorber. It is possible to provide a composition having high properties, particularly a photosensitive composition.

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CN111936532A (zh) * 2018-05-08 2020-11-13 株式会社艾迪科 化合物、潜伏性添加剂、组合物、固化物、固化物的制造方法及组合物的制造方法
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