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WO2017170182A1 - Composition photosensible et nouveau composé - Google Patents

Composition photosensible et nouveau composé Download PDF

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Publication number
WO2017170182A1
WO2017170182A1 PCT/JP2017/011885 JP2017011885W WO2017170182A1 WO 2017170182 A1 WO2017170182 A1 WO 2017170182A1 JP 2017011885 W JP2017011885 W JP 2017011885W WO 2017170182 A1 WO2017170182 A1 WO 2017170182A1
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Prior art keywords
group
carbon atoms
photosensitive composition
substituent
represented
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PCT/JP2017/011885
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English (en)
Japanese (ja)
Inventor
依純 松井
光裕 岡田
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Adeka Corp
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Adeka Corp
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Priority to CN201780005927.6A priority Critical patent/CN108473609B/zh
Priority to JP2018509214A priority patent/JP6889151B2/ja
Priority to KR1020187015982A priority patent/KR102316645B1/ko
Publication of WO2017170182A1 publication Critical patent/WO2017170182A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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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
    • 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
    • C07D251/26—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 only hetero atoms directly attached to ring carbon atoms
    • C07D251/30—Only oxygen atoms
    • C07D251/34—Cyanuric or isocyanuric esters
    • 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
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • 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
    • 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 photosensitive composition containing a compound having a specific structure, which is inactive at room temperature and is activated by heating to a predetermined temperature to exhibit a function, and a novel compound. Furthermore, the present invention relates to a colored photosensitive composition obtained by adding a colorant to the photosensitive 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.
  • Patent Document 6 discloses a triallylphenol compound useful as a curing agent, but does not suggest a photosensitive composition containing the triallylphenol compound.
  • JP 2011-048382 A US Patent Application Publication No. 2016/016919 JP2015-108649A JP2015-132791A International Publication No. 2014/021023 Japanese Patent Laid-Open No. 3-232732
  • 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 photosensitive composition having high solvent resistance.
  • Another object of the present invention is to provide a colored photosensitive composition obtained by adding a colorant to the photosensitive composition, particularly a colored photosensitive composition suitable for a color filter.
  • a photosensitive composition using a compound having a specific protecting group has less outgas, and the cured product has high solvent resistance. It was found that a colored photosensitive composition obtained by adding a colorant to a 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).
  • the present invention has been reached.
  • the present invention has been made based on the above findings, and provides a photosensitive composition containing a compound having a substituent represented by the following general formula (1).
  • 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. )
  • the photosensitive 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 20 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 and R 2 are either a hydrogen atom or a branched alkyl group having 1 to 8 carbon atoms, particularly a t-butyl group, because outgas is 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.
  • 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 low outgas.
  • the aliphatic hydrocarbon group having 1 to 120 carbon atoms which may have a substituent represented by X 1 in the general formula (IA) and having the same valence as n is 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-ethylhexyl
  • 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,
  • Examples of the trivalent n include phenyl-1,3,5-trimethylene 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.
  • 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—,
  • 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.
  • 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 3 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 includes a carbon-carbon double bond, —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO—.
  • the oxygen atom may be replaced by a linking group combining these without being adjacent to each other, * 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 is a carbon-carbon double bond, —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO.
  • 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 is a carbon-carbon double bond, —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO.
  • 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 is a carbon-carbon double bond, —O—, —S—, —CO—, —COO—, —OCO—, —NH—, —SO 2 —, —CONH— or —NHCO.
  • 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).
  • those satisfying the predetermined number of carbon atoms include trivalent groups substituted with Z 1 , Z 2 and Z 3 , etc.
  • 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 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).
  • the thing illustrated by description of R ⁇ 1 > and R ⁇ 2 > in can be mentioned.
  • 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 10 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, the number of carbon atoms 2 to 21 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
  • 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 It can be obtained by reacting a phenolic compound produced by the methods described in JP-A-7-206871, JP-A-7-252191 and JP-T-2004-501128 with an allyl halide compound.
  • the compound having a substituent represented by the general formula (I) can be used as a latent additive in the photosensitive composition of the present invention.
  • 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 content of the compound having a substituent represented by the general formula (I) as a latent additive is 0.001 to 20 in the solid content of the composition of the present invention. % By mass is preferable, and 0.005 to 5% by mass is more preferable.
  • the photosensitive composition of the present invention is a composition whose properties are changed by light irradiation.
  • a positive resist is one that is soluble in a chemical reaction
  • a negative resist is one that is insoluble in a chemical reaction.
  • the photosensitive composition of the present invention contains 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 light.
  • a radical polymerization initiator is contained as an essential component.
  • Examples of 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 replaced by a halogen atom, a nitro group, a cyano group, a hydroxyl group, a carboxyl group or a heterocyclic group, or may be replaced
  • 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
  • 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 addition amount 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 dispersing agent 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 / Those having 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, and each desired layer is sequentially applied to a transparent substrate and activated through a mask having a predetermined pattern shape. It can be used as a transparent laminate obtained by irradiating light, developing the exposed film with a developer, and heating the developed film. As 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.
  • novel compound of the present invention is represented by any of the following structures.
  • the production method of the novel compound of the present invention is not particularly limited.
  • a phenolic compound produced by the method described in each publication of JP-A-2004-501128 and an allyl halide compound can be obtained.
  • 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. 1 Synthesis of Compound 1 Potassium carbonate (2 equivalents with respect to one phenol group) was added to a dimethylacetamide solution of 1 equivalent of 1 ′ phenol compound (3 times the theoretical yield), and the mixture was stirred at room temperature for 30 minutes. Allyl bromide (1.5 equivalent to one phenol group) was added, and the mixture was stirred at 60 ° C. for 5 hours. After adding ethyl acetate and washing with 1% hydrochloric acid solution, oil-water separation was performed, and after drying the organic layer with anhydrous sodium sulfate, the solvent was distilled off and crystallization was performed. The obtained solid was dried under reduced pressure at 60 ° C. for 3 hours to obtain the desired product. 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].
  • 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].
  • 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 2-3. 1 and no. 3 were each coated on 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%.
  • comparative photosensitive composition No. containing no antioxidant was used.
  • a comparative photosensitive composition No. 1 containing a conventional phenolic antioxidant was used.
  • the photosensitive composition No. 1 using the compound according to the present application as a latent additive was used. It is clear that No. 1 maintains the same solvent resistance as when no antioxidant is contained.
  • the photosensitive composition using the compound of the present invention as a latent additive has less outgas and the cured product is excellent in solvent resistance.

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Abstract

L'invention concerne une composition photosensible contenant un composé présentant un substituant indiqué par la formule générale (1). (Dans la formule, R1 et R2 représentent chacun indépendamment un atome d'hydrogène, un atome d'halogène, un groupe cyano, un groupe hydroxyle, un groupe nitro, un groupe carboxyle, un groupe alkyle en C1-40 pouvant présenter un groupe substituant, un groupe aryle en C6-20, un groupe arylalkyle en C7-20, un groupe contenant un noyau hétérocyclique en C2-20 ou un groupe trialkylsilyle. j représente un nombre de 1 à 3 et * indique une liaison à un groupe adjacent, au niveau de la section *.)
PCT/JP2017/011885 2016-03-31 2017-03-23 Composition photosensible et nouveau composé Ceased WO2017170182A1 (fr)

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2020070436A (ja) * 2018-10-25 2020-05-07 株式会社Adeka 組成物、ソルダーレジスト組成物、硬化物及び硬化物の製造方法
JPWO2019004142A1 (ja) * 2017-06-28 2020-07-02 三菱瓦斯化学株式会社 膜形成材料、リソグラフィー用膜形成用組成物、光学部品形成用材料、レジスト組成物、レジストパターン形成方法、レジスト用永久膜、感放射線性組成物、アモルファス膜の製造方法、リソグラフィー用下層膜形成材料、リソグラフィー用下層膜形成用組成物、リソグラフィー用下層膜の製造方法及び回路パターン形成方法
US10927082B2 (en) 2017-03-15 2021-02-23 Metacrine, Inc. Farnesoid X receptor agonists and uses thereof
US11084817B2 (en) 2018-09-18 2021-08-10 Metacrine, Inc. Farnesoid X receptor agonists and uses thereof
US11236071B1 (en) 2017-03-15 2022-02-01 Metacrine, Inc. Farnesoid X receptor agonists and uses thereof
WO2022176753A1 (fr) * 2021-02-18 2022-08-25 本州化学工業株式会社 Nouveau composé de tris(allyl éther) ayant une structure de triphénylalcane
JP2023084279A (ja) * 2021-12-07 2023-06-19 Dic株式会社 硬化性樹脂組成物、硬化物及び物品
JP2023084278A (ja) * 2021-12-07 2023-06-19 Dic株式会社 硬化性樹脂組成物、硬化物、絶縁材料及びレジスト部材
WO2023176725A1 (fr) * 2022-03-16 2023-09-21 本州化学工業株式会社 Composé d'éther allylique et son procédé de production, composition de résine durcissable, vernis, préimprégné, produit durci, agent de durcissement de résine d'éther de polyphénylène, et cristaux et leur procédé de production

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111072605B (zh) * 2019-12-17 2021-11-02 赣南医学院 一种氟烷基取代的苯并呋喃衍生物或吲哚衍生物的制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06298911A (ja) * 1993-04-16 1994-10-25 Toyo Ink Mfg Co Ltd 感光性組成物
JP2002120233A (ja) * 2000-10-13 2002-04-23 Seiko Epson Corp プラスチックレンズの製造方法
WO2007109295A2 (fr) * 2006-03-20 2007-09-27 Ophthonix, Inc. Monomeres et polymeres sur mesure pour verres de lunettes
JP2010285507A (ja) * 2009-06-10 2010-12-24 Kaneka Corp 接着性硬化性組成物

Family Cites Families (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE630551A (fr) * 1961-06-16
CH484695A (de) * 1962-10-30 1970-01-31 Ciba Geigy Verwendung von neuen Hydroxyphenyl-1,3,5-triazinen als Ultraviolettschutzmittel ausserhalb der Textilindustrie
US4321396A (en) * 1980-01-17 1982-03-23 Gaf Corporation Copolymerizable, ultraviolet light absorber allyloxy-2-(2H-benzotriazol-2-yl)-4-alkylbenzenes
US4373060A (en) * 1980-05-30 1983-02-08 General Electric Company Silicone coating for unprimed plastic substrate and coated articles
US4316033A (en) * 1980-05-30 1982-02-16 General Electric Company Alkoxysilylbenzotriazoles
US4467082A (en) * 1982-03-15 1984-08-21 Dow Corning Corporation Organopolysiloxane photosensitizers and methods for their preparation
CA1189872A (fr) * 1982-03-23 1985-07-02 Keiichi Kishimoto Agents de photosensibilisation a base d'organopolysiloxane, et methode de preparation
JPS5915418A (ja) * 1982-07-15 1984-01-26 Matsushita Electric Ind Co Ltd 感光性樹脂
JPS6185421A (ja) * 1984-10-02 1986-05-01 Japan Synthetic Rubber Co Ltd 感光性樹脂の製造方法
JPS63183440A (ja) * 1987-01-27 1988-07-28 Japan Synthetic Rubber Co Ltd パタ−ン形成方法
JPH03232832A (ja) * 1990-02-05 1991-10-16 Mitsubishi Petrochem Co Ltd トリアリルフェノール化合物及び硬化剤
JP3334112B2 (ja) * 1992-03-23 2002-10-15 ジェイエスアール株式会社 レジスト塗布組成物
KR100341563B1 (ko) * 1992-03-23 2002-10-25 제이에스알 가부시끼가이샤 레지스트도포조성물
JPH10212469A (ja) * 1997-01-28 1998-08-11 Dai Ichi Kogyo Seiyaku Co Ltd 紫外線吸収剤
JP4225612B2 (ja) * 1998-09-09 2009-02-18 スター・ジャパン株式会社 眼用レンズ材料
JP4146105B2 (ja) * 2001-05-30 2008-09-03 富士フイルム株式会社 紫外線吸収剤及びその製造方法、紫外線吸収剤を含有する組成物、ならびに画像形成方法
TW200631930A (en) * 2004-10-26 2006-09-16 Showa Denko Kk Thiol compound and photosensitive composition using the compound
KR101472869B1 (ko) * 2008-04-28 2014-12-15 후지필름 가부시키가이샤 광중합성 조성물, 컬러필터용 광중합성 조성물, 컬러필터와 그 제조 방법, 고체촬상소자, 및 평판 인쇄판 원판
JP2010008780A (ja) * 2008-06-27 2010-01-14 Fujifilm Corp 光重合性組成物、カラーフィルタ及びその製造方法、固体撮像素子、並びに平版印刷版原版
JP2011048382A (ja) 2010-10-01 2011-03-10 Kodak Japan Ltd 感光性組成物、感光性平版印刷版および平版印刷版の作成方法
JP5644476B2 (ja) * 2010-12-22 2014-12-24 東レ株式会社 感光性樹脂組成物、それを用いた硬化膜、半導体装置の製造方法および半導体装置
TWI542644B (zh) * 2011-02-09 2016-07-21 Sumitomo Chemical Co Coloring the photosensitive resin composition
EP2881450B1 (fr) 2012-07-31 2020-09-09 Adeka Corporation Additif latent et composition le contenant
JP6049521B2 (ja) 2013-03-29 2016-12-21 富士フイルム株式会社 感光性樹脂組成物、硬化膜、画像形成方法、固体撮像素子、カラーフィルタおよび紫外線吸収剤
WO2014192973A1 (fr) * 2013-05-31 2014-12-04 住友化学株式会社 Composé et composition de résine vulcanisable colorée
JP2015108649A (ja) 2013-12-03 2015-06-11 凸版印刷株式会社 青色感光性組成物およびカラーフィルタ基板
JP2015132791A (ja) 2013-12-13 2015-07-23 株式会社Adeka 着色感光性組成物

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06298911A (ja) * 1993-04-16 1994-10-25 Toyo Ink Mfg Co Ltd 感光性組成物
JP2002120233A (ja) * 2000-10-13 2002-04-23 Seiko Epson Corp プラスチックレンズの製造方法
WO2007109295A2 (fr) * 2006-03-20 2007-09-27 Ophthonix, Inc. Monomeres et polymeres sur mesure pour verres de lunettes
JP2010285507A (ja) * 2009-06-10 2010-12-24 Kaneka Corp 接着性硬化性組成物

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* Cited by examiner, † Cited by third party
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US10961198B2 (en) 2017-03-15 2021-03-30 Metacrine, Inc. Farnesoid X receptor agonists and uses thereof
US11236071B1 (en) 2017-03-15 2022-02-01 Metacrine, Inc. Farnesoid X receptor agonists and uses thereof
JPWO2019004142A1 (ja) * 2017-06-28 2020-07-02 三菱瓦斯化学株式会社 膜形成材料、リソグラフィー用膜形成用組成物、光学部品形成用材料、レジスト組成物、レジストパターン形成方法、レジスト用永久膜、感放射線性組成物、アモルファス膜の製造方法、リソグラフィー用下層膜形成材料、リソグラフィー用下層膜形成用組成物、リソグラフィー用下層膜の製造方法及び回路パターン形成方法
JP7252516B2 (ja) 2017-06-28 2023-04-05 三菱瓦斯化学株式会社 膜形成材料、リソグラフィー用膜形成用組成物、光学部品形成用材料、レジスト組成物、レジストパターン形成方法、レジスト用永久膜、感放射線性組成物、アモルファス膜の製造方法、リソグラフィー用下層膜形成材料、リソグラフィー用下層膜形成用組成物、リソグラフィー用下層膜の製造方法及び回路パターン形成方法
US11773094B2 (en) 2018-09-18 2023-10-03 Organovo, Inc. Farnesoid X receptor agonists and uses thereof
US11084817B2 (en) 2018-09-18 2021-08-10 Metacrine, Inc. Farnesoid X receptor agonists and uses thereof
JP2020070436A (ja) * 2018-10-25 2020-05-07 株式会社Adeka 組成物、ソルダーレジスト組成物、硬化物及び硬化物の製造方法
JP7436176B2 (ja) 2018-10-25 2024-02-21 株式会社Adeka 組成物、ソルダーレジスト組成物、硬化物及び硬化物の製造方法
WO2022176753A1 (fr) * 2021-02-18 2022-08-25 本州化学工業株式会社 Nouveau composé de tris(allyl éther) ayant une structure de triphénylalcane
JP2023084278A (ja) * 2021-12-07 2023-06-19 Dic株式会社 硬化性樹脂組成物、硬化物、絶縁材料及びレジスト部材
JP2023084279A (ja) * 2021-12-07 2023-06-19 Dic株式会社 硬化性樹脂組成物、硬化物及び物品
JP7739991B2 (ja) 2021-12-07 2025-09-17 Dic株式会社 硬化性樹脂組成物、硬化物及び物品
JP7739990B2 (ja) 2021-12-07 2025-09-17 Dic株式会社 硬化性樹脂組成物、硬化物、絶縁材料及びレジスト部材
WO2023176725A1 (fr) * 2022-03-16 2023-09-21 本州化学工業株式会社 Composé d'éther allylique et son procédé de production, composition de résine durcissable, vernis, préimprégné, produit durci, agent de durcissement de résine d'éther de polyphénylène, et cristaux et leur procédé de production

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