WO2016122160A1 - Nouveau composé dioximester et amorceur de photopolymérisation et composition de résine photosensible contenant ce composé - Google Patents

Nouveau composé dioximester et amorceur de photopolymérisation et composition de résine photosensible contenant ce composé Download PDF

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WO2016122160A1
WO2016122160A1 PCT/KR2016/000635 KR2016000635W WO2016122160A1 WO 2016122160 A1 WO2016122160 A1 WO 2016122160A1 KR 2016000635 W KR2016000635 W KR 2016000635W WO 2016122160 A1 WO2016122160 A1 WO 2016122160A1
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reaction
mol
added
biphenyl
minutes
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Korean (ko)
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오천림
이득락
이민선
이원중
이재훈
조용일
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주식회사 삼양사
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Publication of WO2016122160A1 publication Critical patent/WO2016122160A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
    • C07C251/64—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids
    • C07C251/66—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids with the esterifying carboxyl groups bound to hydrogen atoms, to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/62—Oximes having oxygen atoms of oxyimino groups esterified
    • C07C251/64—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids
    • C07C251/68—Oximes having oxygen atoms of oxyimino groups esterified by carboxylic acids with at least one of the esterifying carboxyl groups bound to a carbon atom of a six-membered aromatic ring
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—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
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • 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
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • 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
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • 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
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images

Definitions

  • the present invention relates to a novel dioxime ester compound and a photopolymerization initiator and photoresist composition comprising the same.
  • the photopolymerization initiator used in the photoresist composition various kinds such as acetophenone derivatives, benzophenone derivatives, triazine derivatives, biimidazole derivatives, acylphosphine oxide derivatives and oxime ester derivatives are known. It absorbs ultraviolet rays, exhibits little color, has high radical generation efficiency, and has excellent compatibility and stability with photoresist composition materials.
  • the earlier developed oxime derivative compounds have a low photoinitiation efficiency, in particular, a low sensitivity in the pattern exposure process, so the exposure should be increased, resulting in a decrease in production.
  • the oxime ester compound is capable of polymerizing and curing a polymerizable compound having an unsaturated bond by irradiating the photoresist composition with light of 365-435 nm, which is used for a black matrix, color filter, column spacer, flexible insulating film, photoresist composition for overcoat, and the like. It is becoming.
  • the photoinitiator has high sensitivity to long wavelength light sources such as 365-435 nm, has good photopolymerization reactivity, easy to manufacture, high thermal stability and storage stability, and easy to handle, and it is easy to handle (PGMEA; propylene glycol monomethyl ether acetate).
  • PGMEA propylene glycol monomethyl ether acetate
  • photoresist compositions used in thin film displays such as liquid crystal display devices and OLEDs
  • alkaline developer to form organic insulating films, column spacers, UV overcoats, R.G.B.
  • a lot of research is being conducted on the photoresist composition containing a high-sensitivity photopolymerization initiator capable of pattern formation with a color resist, a black matrix, or the like.
  • the photoresist composition containing a binder resin, the polyfunctional monomer which has an ethylenically unsaturated bond, and a photoinitiator is preferable.
  • the sensitivity is low during the exposure process for pattern formation, so the amount of use of the photopolymerization initiator must be increased or the exposure amount must be increased, thereby contaminating the mask in the exposure process, and the photopolymerization initiator at high temperature crosslinking.
  • the yield is reduced as a by-product generated after decomposition, there is a problem that the production process is reduced by increasing the exposure process time according to the increase in the exposure amount, efforts are being made to solve this problem.
  • Patent Document 1 JP 2001-302871 A (2001.10.31)
  • Patent Document 2 JP 2006-160634 A (2006.06.22)
  • Patent Document 3 JP 2005-025169 A (2005.01.27)
  • Patent Document 4 JP 2005-242279 A (2005.09.08)
  • Patent Document 5 WO 02/100903 (2002.12.19)
  • Patent Document 6 WO 07/071497 (2007.06.28)
  • Patent Document 7 WO 08/138733 (2008.11.20)
  • Patent Document 8 WO 08/078686 (2008.07.03)
  • Patent Document 9 WO 09/081483 (2009.07.02)
  • an object of the present invention is to provide a novel dioxime ester compound, a photopolymerization initiator containing the same, and a photoresist composition comprising the dioxime ester compound.
  • Another object of the present invention is to provide a molded article comprising a cured product of a photoresist composition containing a novel dioxime ester compound.
  • Another object of the present invention is to provide a display device including the molding of the present invention.
  • the present invention provides a dioxime ester compound represented by the following formula (1), a photopolymerization initiator and a photoresist composition comprising the same.
  • R 1 to R 3 are each independently hydrogen, halogen, (C 1 -C 20 ) alkyl, (C 6 -C 20 ) aryl, (C 1 -C 20 ) alkoxy, (C 6 -C 20 ) aryl (C 1 -C 20 ) alkyl, hydroxy (C 1 -C 20 ) alkyl, hydroxy (C 1 -C 20 ) alkoxy (C 1 -C 20 ) alkyl, (C 3 -C 20 ) cycloalkyl or (C 3 -C 20 ) cycloalkyl (C 1 -C 20 ) alkyl;
  • A is hydrogen, halogen, (C 1 -C 20 ) alkyl, (C 6 -C 20 ) aryl, (C 6 -C 20 ) aryl (C 1 -C 20 ) alkyl, amino, nitro, cyano or hydroxy ego;
  • n is an integer of 0-2.
  • halo or halogen in the present invention means fluorine, chlorine, bromine or iodine atoms.
  • alkyl refers to a monovalent straight-chain or pulverized saturated hydrocarbon radical consisting solely of carbon and hydrogen atoms, e.g. methyl, ethyl, propyl, isopropyl, butyl, isobutyl, t-butyl, pentyl, hexyl , Octyl, nonyl, and the like.
  • aryl in the present invention refers to an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, in which a single or fused ring containing 4 to 7, preferably 5 or 6 ring atoms, suitably in each ring It includes a system, including a form in which a plurality of aryl is connected by a single bond. Specific examples include, but are not limited to, phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, fluorenyl, phenanthryl, and the like.
  • alkoxy refers to an -O-alkyl radical, which may be exemplified by methoxy, ethoxy, isopropoxy, butoxy, isobutoxy, t-butoxy and the like.
  • arylalkyl of the present invention is an alkyl group substituted with aryl as defined above, and may be exemplified by benzyl and the like.
  • hydroxyalkyl of the present invention is an hydroxy substituted alkyl group, which may be exemplified by hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxypentyl, hydroxyhexyl, and the like.
  • hydroxyalkoxyalkyl of the present invention is an alkyl group substituted with hydroxyalkoxy, which is hydroxymethoxymethyl, hydroxymethoxyethyl, hydroxymethoxypropyl, hydroxymethoxybutyl, hydroxyethoxymethyl, Hydroxyethoxyethyl, hydroxyethoxypropyl, hydroxyethoxybutyl, hydroxyethoxypentyl, hydroxyethoxyhexyl and the like.
  • cycloalkyl as used herein means a monocyclic alkyl group having 3 to 7 carbon atoms as well as a polycyclic alkyl group in which two or more monocyclic alkyls are fused. Specific examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like.
  • cycloalkylalkyl refers to an alkyl group substituted with a cycloalkyl as defined above, and may be exemplified by cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclopropylethyl and the like.
  • the '(C 1 -C 20 ) alkyl' group described in the present invention is preferably (C 1 -C 10 ) alkyl, more preferably (C 1 -C 6 ) alkyl.
  • the '(C 6 -C 20 ) aryl' group is preferably (C 6 -C 18 ) aryl.
  • the '(C 1 -C 20 ) alkoxy' group is preferably (C 1 -C 10 ) alkoxy, more preferably (C1-C4) alkoxy.
  • the '(C 6 -C 20 ) aryl (C 1 -C 20 ) alkyl' group is preferably (C 6 -C 18 ) aryl (C 1 -C 10 ) alkyl, more preferably (C 6 -C 18) ) Aryl (C 1 -C 6 ) alkyl.
  • the 'hydroxy (C 1 -C 20 ) alkyl' group is preferably hydroxy (C 1 -C 10 ) alkyl, more preferably hydroxy (C 1 -C 6 ) alkyl.
  • the 'hydroxy (C 1 -C 20 ) alkoxy (C 1 -C 20 ) alkyl' group is preferably hydroxy (C 1 -C 10 ) alkoxy (C 1 -C 10 ) alkyl, more preferably hydroxy (C 1 -C 4 ) alkoxy (C 1 -C 6 )) alkyl.
  • the '(C 3 -C 20 ) cycloalkyl' group is preferably (C 3 -C 10 ) cycloalkyl.
  • the '(C 3 -C 20 ) cycloalkyl (C 1 -C 20 ) alkyl' group is preferably (C 3 -C 10 ) cycloalkyl (C 1 -C 10 ) alkyl, more preferably (C 3- C 10 ) cycloalkyl (C 1 -C 6 ) alkyl.
  • each R 1 may be the same or different from each other.
  • R 1 to R 3 are each independently hydrogen, bromo, chloro, iodo, methyl, ethyl, n -propyl, i -propyl, n -butyl, i -butyl, t -butyl, n -pentyl , i -pentyl, n -hexyl, i -hexyl, phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, phenanthryl, methoxy, ethoxy, n -propyloxy, i -propyloxy, n -Butoxy, i -butoxy, t -butoxy, benzyl, hydroxymethyl, hydroxyethyl, hydroxy n -propyl, hydroxy n -butyl, hydroxy i -butyl, hydroxy n -pentyl, methyl,
  • A is hydrogen, bromo, chloro, methyl, ethyl, n -propyl, i -propyl, n -butyl, i -butyl, t -butyl, phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, Phenanthryl, benzyl, amino, nitro, cyano or hydroxy, but is not limited thereto.
  • R 1 is hydrogen, (C 1 -C 20 ) alkyl, (C 6 -C 20 ) aryl (C 1 -C 20 ) alkyl, hydroxy (C 1 -C 20 ) alkyl, hydride Oxy (C 1 -C 20 ) alkoxy (C 1 -C 20 ) alkyl, (C 3 -C 20 ) cycloalkyl or (C 3 -C 20 ) cycloalkyl (C 1 -C 20 ) alkyl;
  • R 2 and R 3 are each independently (C 1 -C 20 ) alkyl, (C 6 -C 20 ) aryl, (C 6 -C 20 ) aryl (C 1 -C 20 ) alkyl, hydroxy (C 1- C 20 ) alkyl, hydroxy (C 1 -C 20 ) alkoxy (C 1 -C 20 ) alkyl, (C 3 -C 20 ) cycloalkyl or (
  • R 1 is hydrogen, (C 1 -C 20 ) alkyl, (C 3 -C 20 ) cycloalkyl or (C 3 -C 20 ) cycloalkyl (C 1 -C 20 ) alkyl ;
  • R 2 and R 3 are each independently (C 1 -C 20 ) alkyl, (C 6 -C 20 ) aryl or (C 3 -C 20 ) cycloalkyl;
  • A can be hydrogen, halogen, (C 1 -C 20 ) alkyl, (C 6 -C 20 ) aryl, nitro or cyano.
  • the dioxime ester compound according to the present invention may include the following compounds, but the following compounds are not intended to limit the present invention.
  • the dioxime ester compound represented by Formula 1 according to the present invention may be prepared as shown in Scheme 1 below.
  • the present invention provides a photopolymerization initiator comprising a dioxime ester compound represented by the formula (1).
  • the present invention provides a photoresist composition
  • a photoresist composition comprising a dioxime ester compound represented by the formula (1).
  • the dioxime ester compound represented by Chemical Formula 1 may be included in the photoresist composition as a photopolymerization initiator.
  • the photoresist composition of the present invention includes a dioxime ester compound represented by Chemical Formula 1, a binder resin, a polymerizable compound having an ethylenically unsaturated bond, a solvent, and the like, and has thin film properties such as pattern property control and heat resistance and chemical resistance. outstanding.
  • the photoresist composition of the present invention is a thioxanthone compound, acetophenone compound, biimidazole compound, triazine compound, thiol compound and O-acyl oxime compound in addition to the dioxime ester compound represented by the formula (1) It may further comprise one or two or more known photopolymerization initiators selected from the group consisting of.
  • thioxanthone-based compound examples include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2,4-dichlorothioxanthone, 2, 4- dimethyl thioxanthone, 2, 4- diethyl thioxanthone, 2, 4- diisopropyl thioxanthone, etc., These can be used individually or in mixture of 2 or more types, respectively.
  • acetophenone compounds examples include 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane-1-one and 2-benzyl-2-dimethylamino-1- (4-morpholine Nophenyl) butan-1-one, 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinophenyl) butan-1-one, and the like; It can mix and use species.
  • biimidazole-based compound 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis ( 2,4-dichlorolophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis (2,4,6-trichlorophenyl) -4 , 4 ', 5,5'-tetraphenyl-1,2'-biimidazole, and the like, and these may be used alone or in combination of two or more thereof.
  • triazine-based compound examples include 2,4,6-tris (trichloromethyl) -s-triazine, 2-methyl-4,6-bis (trichloromethyl) -s-triazine, 2- [2- ( 5-methylfuran-2-yl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- [2- (furan-2-yl) ethenyl] -4,6-bis (Trichloromethyl) -s-triazine, 2- [2- (4-diethylamino-2-methylphenyl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- [ 2- (3,4-dimethoxyphenyl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxyphenyl) -4,6-bis (trichloromethyl ) -s
  • an acrylic polymer or an acrylic polymer having an acrylic unsaturated bond in the side chain may be used, and thin film properties such as pattern property control and heat resistance and chemical resistance may be used. It is preferable to use 3 to 50% by weight with respect to 100% by weight of the photoresist composition, polystyrene reduced weight average molecular weight by gel permeation chromatography (GPC) of the acrylic polymer is 2,000 to 30,000,000, dispersion degree is It is preferable to use what is 1.0-10.0, and it is more preferable to use what is a weight average molecular weight 4,000-100000,00.
  • GPC gel permeation chromatography
  • the acrylic polymer is a copolymer of monomers including the following monomers.
  • the monomers include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, and pentyl (meth).
  • An acrylic polymer having an acrylic unsaturated bond in the side chain is a copolymer obtained by adding an epoxy resin to an acrylic copolymer containing a carboxylic acid, such as acrylic acid, methacrylic acid, itaconic acid, maleic acid, and maleic acid monoalkyl ester.
  • a carboxylic acid such as acrylic acid, methacrylic acid, itaconic acid, maleic acid, and maleic acid monoalkyl ester.
  • an acrylic polymer having an acrylic unsaturated bond in the side chain is a copolymer in which a carboxylic acid is added to an acrylic copolymer containing an epoxy group, and glycidyl acrylate, glycidyl methacrylate, and 3,4-epoxy.
  • Acrylic monomer containing methyl groups such as butyl (meth) acrylate, 2,3-epoxycyclohexyl (meth) acrylate, 3,4-epoxycyclohexyl methyl (meth) acrylate, methyl (meth) acrylate, hexyl Alkyl (meth) acrylates, such as (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclo Pentenyl (meth) acrylate, benzyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, styrene, ⁇ -methylstyrene, acetoxystyrene, N ⁇ Me Maleimide, N - e
  • the polymerizable compound having an ethylenically unsaturated bond serves to form a pattern by crosslinking by photoreaction at the time of pattern formation and crosslinking at high temperature to impart chemical resistance and heat resistance.
  • the polymerizable compound having an ethylenically unsaturated bond preferably uses 0.001 to 40% by weight based on 100% by weight of the photoresist composition.
  • the polymerizable compound having an ethylenically unsaturated bond is specifically methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, lauryl (meth) acryl Alkyl ester of (meth) acrylic acid, such as the rate, glycidyl (meth) acrylate, polyethyleneglycol mono (meth) acrylate whose number of ethylene oxide groups is 2-14, ethylene glycol di (meth) acrylate, ethylene oxide group Polyethylene glycol di (meth) acrylate having a number of from 2 to 14, propylene glycol di (meth) acrylate having a number of from 2 to 14 of propylene oxide group, trimethylolpropanedi (meth) acrylate, bisphenol A diglycidyl ether Acrylic acid adduct, phthalic acid diester of ⁇ -hydroxyethyl
  • the amount of the dioxime ester compound of Chemical Formula 1 used as a photopolymerization initiator in the photoresist composition of the present invention is 0.01 to 10% by weight with respect to 100% by weight of the photoresist composition, preferably to increase transparency and minimize exposure. It is more effective to use 0.1 to 5% by weight.
  • the photoresist composition of the present invention may further include a silicone-based compound having an epoxy group or an amine group as an adhesion aid as necessary.
  • the silicon-based compound may improve adhesion between the ITO electrode and the photoresist composition and may increase heat resistance after curing.
  • a silicone type compound which has the said epoxy group or an amine group (3-glycidoxy propyl) trimethoxysilane, (3-glycidoxy propyl) triethoxy silane, (3-glycidoxy propyl) methyl dimethoxy silane Phosphorus, (3-glycidoxypropyl) methyldiethoxysilane, (3-glycidoxypropyl) dimethylmethoxysilane, (3-glycidoxypropyl) dimethylethoxysilane, 3,4-epoxybutyl Trimethoxysilane, 3,4-epoxybutyltriethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane,
  • the photoresist composition of the present invention may further include a compatible additive such as a photosensitizer, a thermal polymerization inhibitor, an antifoaming agent, a leveling agent and the like as necessary.
  • a compatible additive such as a photosensitizer, a thermal polymerization inhibitor, an antifoaming agent, a leveling agent and the like as necessary.
  • the photoresist composition of the present invention is spin-coated onto a substrate by adding a solvent, and then forms a pattern through a method of developing with an alkali developer by irradiating ultraviolet rays using a mask, wherein the photoresist composition is 10 to 95% by weight based on 100% by weight of the photoresist composition. It is preferred to add% solvent to adjust the viscosity to be in the range of 1 to 50 cps.
  • the solvent may be ethyl acetate, butyl acetate, diethylene glycol dimethyl ether, diethylene glycol dimethyl ethyl ether, methyl methoxy propionate, ethyl ethoxy propionate in consideration of compatibility with binder resins, photoinitiators and other compounds.
  • EEP ethyl lactate
  • PMEA propylene glycol monomethyl ether acetate
  • PMEP propylene glycol methyl ether propionate
  • EEP ethyl lactate
  • PMEA propylene glycol monomethyl ether acetate
  • PMEP propylene glycol methyl ether propyl ether
  • methyl cellosolve acetate ethyl cellosolve acetate
  • Diethylene glycol methyl acetate diethylene glycol ethyl acetate, acetone, methyl isobutyl ketone, cyclohexanone, dimethylformamide (DMF), N , N -dimethylacetamide (DMAc), N -methyl-2-pyrroli Don (NMP), ⁇ -butylolactone, diethyl ether, ethylene glycol dimethyl ether, diglyme, tetrahydrofue Column (THF), methanol, ethanol, propanol,
  • Photoresist composition according to an embodiment of the present invention is a known means such as spin coater, roll coater, bar coater, die coater, curtain coater, various printing, immersion, soda glass, quartz glass, semiconductor substrate, metal, It can be applied to a supporting substrate such as paper or plastic. Moreover, it can transfer to another support base body after performing it once on support bases, such as a film, and there is no restriction
  • a photoresist composition according to an embodiment of the present invention is a color filter in a liquid crystal display device of a color display such as a photocurable paint or varnish, a photocurable adhesive, a printed board, or a color television, a PC monitor, a portable information terminal, a digital camera, or the like.
  • Electrode material for plasma display panel powder coating, printing ink, printing plate, adhesive, dental composition, gel coating, photoresist for electronic engineering, electroplating resist, etching resist, solder resist for both liquid and dry film, various marking Compositions for manufacturing color matrices for use or for forming structures in plasma display panels, electroluminescent displays, and LCDs, compositions for encapsulating electrical and electronic components, magnetic recording materials, micromechanical components Waveguides, Optical Switches, Plating Masks, Etch Masks, Color Test Systems, Fiberglass Cables Coating, stencils for screen printing, materials for manufacturing three-dimensional objects by stereo lithography, materials for holographic recording, image recording materials, microelectronic circuits, color decoloring materials, color decoloring materials for image recording materials, image recording materials using microcapsules It can be used for various applications such as discoloration material for photoresist, photoresist material for printed wiring board, photoresist material for UV and visible laser direct imaging system, photoresist material for forming
  • the present invention provides a photoresist composition comprising a coloring material in the photoresist composition comprising a dioxime ester compound represented by the formula (1).
  • the photoresist composition may be added to the coloring material according to the use to prepare a colored photoresist composition, the coloring material may be used a variety of coloring materials, such as black, red, yellow, green, blue. In order to manufacture a black matrix, a black coloring material is added, and in order to manufacture a color filter, various coloring materials which show R.G.B.color etc. can be used.
  • a coloring material contained in order to apply it to molded object formation resists such as a color filter and a black matrix
  • cyan, magenta, yellow, and black pigment of a red, green, blue, and dark blue mixed system are mentioned.
  • pigments CI Pigment Yellow 12, 13, 14, 17, 20, 24, 55, 83, 86, 93, 109, 110, 117, 125, 137, 139, 147, 148, 153, 154, 166, 168 , CI Pigment Orange 36, 43, 51, 55, 59, 61, CI Pigment Red 9, 97, 122, 123, 149, 168, 177, 180, 192, 215, 216, 217, 220, 223, 224, 226 , 227, 228, 240, CI Pigment Violet 19, 23, 29, 30, 37, 40, 50, CI Pigment Blue 15, 15: 1, 15: 4, 15: 6, 22, 60, 64, CI Pigment Green 7, 36, CI Pigment brown 23, 25, 26, CI pigment black 7, titanium
  • the present invention also provides a molded article comprising the cured product of the photoresist composition.
  • the molding of the present invention is characterized in that the array planarization film, the insulating film, the column spacer, the black column spacer, the black matrix or the color filter.
  • the present invention provides a display device including the molding.
  • the dioxime ester compound of the present invention When used as a photoinitiator of the photoresist composition, the dioxime ester compound of the present invention has excellent sensitivity even when used in a small amount, and has excellent physical properties such as residual film ratio, pattern stability, chemical resistance, and ductility. And it is possible to minimize the outgassing from the photopolymerization initiator in the post-baking process can reduce the contamination and there is an advantage that can minimize the defects that can be caused by this.
  • reaction solution was cooled to room temperature, 30 mL of H 2 O was added thereto, followed by stirring for about 30 minutes, and 40 mL of 1% HCl aqueous solution was slowly added dropwise to neutralize the pH of the reaction product to 6-7. 100 mL of ethyl acetate was added to the reaction solution, the mixture was stirred for 30 minutes, and the organic layer was separated. The organic layer was washed with H 2 O. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
  • n -hexane 1: 4) to obtain 8.54 g (92.0%) of 1- (biphenyl-4-yl) butane-1,3-dione O, O-dicyclohexanecarbonyl dioxime ( 6 ) Got it.
  • reaction solution was cooled to room temperature, 30 mL of H 2 O was added thereto, followed by stirring for about 30 minutes, and 40 mL of 1% HCl aqueous solution was slowly added dropwise to neutralize the pH of the reaction product to 6-7. 100 mL of ethyl acetate was added to the reaction solution, the mixture was stirred for 30 minutes, and the organic layer was separated. The organic layer was washed with H 2 O. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
  • n -hexane 1: 4
  • n -hexane 1: 4
  • Biphenyl ( 14 ) Dissolve 10.0 g (0.065 mol) in 100 mL of dichloromethane, cool the reaction to -5 ° C, slowly add 10.40 g (0.78 mol) of aluminum chloride, and 5 mL of dichloromethane, taking care not to raise the temperature of the reaction. 12.53 g (0.078 mol) of 2-cyclohexylacetyl chloride diluted in was slowly added over 2 hours, and the reaction was stirred at -5 ° C for 1 hour.
  • reaction solution was cooled to room temperature, 30 mL of H 2 O was added, followed by stirring for about 30 minutes, and 30 mL of 1% aqueous HCl solution was slowly added dropwise to neutralize the pH of the reaction product to 6-7. 100 mL of ethyl acetate was added to the reaction solution, the mixture was stirred for 30 minutes, and the organic layer was separated. The organic layer was washed with H 2 O. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
  • n - hexane 1: 4) to give 1- (biphenyl-4-yl) -2-cyclohexyl-butane-1,3-dione O, O- di-acetyl-di-oxime (18) 5.49 g (90.3% )
  • Biphenyl ( 14 ) Dissolve 10.0 g (0.065 mol) in 100 mL of dichloromethane, cool the reaction to -5 ° C, slowly add 10.40 g (0.78 mol) of aluminum chloride, and 5 mL of dichloromethane, taking care not to raise the temperature of the reaction. 12.53 g (0.078 mol) of 3-cyclopentylpropionyl chloride diluted in was slowly added over 2 hours, and the reaction was stirred at -5 ° C for 1 hour.
  • reaction solution was cooled to room temperature, 30 mL of H 2 O was added, followed by stirring for about 30 minutes, and 30 mL of 1% aqueous HCl solution was slowly added dropwise to neutralize the pH of the reaction product to 6-7. 100 mL of ethyl acetate was added to the reaction solution, the mixture was stirred for 30 minutes, and the organic layer was separated. The organic layer was washed with H 2 O. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
  • reaction solution was cooled to room temperature, 30 mL of H 2 O was added thereto, followed by stirring for about 30 minutes, and 40 mL of 1% HCl aqueous solution was slowly added dropwise to neutralize the pH of the reaction product to 6-7. 100 mL of ethyl acetate was added to the reaction solution, the mixture was stirred for 30 minutes, and the organic layer was separated. The organic layer was washed with H 2 O. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
  • n -hexane 1: 4) to obtain 5.84 g (90.3%) of 1- (biphenyl-4-yl) hexane-1,3-dione O, O-diacetyl dioxime ( 25 ).
  • reaction solution was cooled to room temperature, 30 mL of H 2 O was added thereto, followed by stirring for about 30 minutes, and 80 mL of an aqueous 1% HCl solution was slowly added dropwise to neutralize the pH of the reaction product to 6-7. 100 mL of ethyl acetate was added to the reaction solution, the mixture was stirred for 30 minutes, and the organic layer was separated. The organic layer was washed with H 2 O. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
  • the obtained solid product was dispersed in 500 mL of distilled water, stirred at room temperature for about 30 minutes, filtered, washed sufficiently with distilled water, and dried to light gray 1- (4'-nitro-biphenyl-4-yl) ethanone ( 31 ). 17.8 g (67.2%) was obtained.
  • reaction solution was cooled to room temperature, 30 mL of H 2 O was added thereto, followed by stirring for about 30 minutes, and 80 mL of an aqueous 1% HCl solution was slowly added dropwise to neutralize the pH of the reaction product to 6-7. 100 mL of ethyl acetate was added to the reaction solution, the mixture was stirred for 30 minutes, and the organic layer was separated. The organic layer was washed with H 2 O. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
  • reaction solution was cooled to room temperature, 30 mL of H 2 O was added thereto, followed by stirring for about 30 minutes, and 80 mL of an aqueous 1% HCl solution was slowly added dropwise to neutralize the pH of the reaction product to 6-7. 100 mL of ethyl acetate was added to the reaction solution, the mixture was stirred for 30 minutes, and the organic layer was separated. The organic layer was washed with H 2 O. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
  • Biphenyl ( 14 ) Dissolve 10.0 g (0.065 mol) in 100 mL of dichloromethane, cool the reaction to -5 ° C, slowly add 10.40 g (0.78 mol) of aluminum chloride, and 5 mL of dichloromethane, taking care not to raise the temperature of the reaction. 11.59 g (0.078 mol) of heptanoyl chloride diluted in was slowly added over 2 hours, and the reaction was stirred at -5 ° C for 1 hour.
  • reaction solution was cooled to room temperature, 30 mL of H 2 O was added, followed by stirring for about 30 minutes, and 30 mL of 1% aqueous HCl solution was slowly added dropwise to neutralize the pH of the reaction product to 6-7. 100 mL of ethyl acetate was added to the reaction solution, the mixture was stirred for 30 minutes, and the organic layer was separated. The organic layer was washed with H 2 O. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
  • reaction solution was cooled to room temperature, 30 mL of H 2 O was added, followed by stirring for about 30 minutes, and 30 mL of 1% aqueous HCl solution was slowly added dropwise to neutralize the pH of the reaction product to 6-7. 100 mL of ethyl acetate was added to the reaction solution, the mixture was stirred for 30 minutes, and the organic layer was separated. The organic layer was washed with H 2 O. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
  • reaction solution was cooled to room temperature, 30 mL of H 2 O was added, followed by stirring for about 30 minutes, and 30 mL of 1% aqueous HCl solution was slowly added dropwise to neutralize the pH of the reaction product to 6-7. 100 mL of ethyl acetate was added to the reaction solution, the mixture was stirred for 30 minutes, and the organic layer was separated. The organic layer was washed with H 2 O. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
  • reaction solution was cooled to room temperature, 30 mL of H 2 O was added thereto, stirred for about 30 minutes, and then slowly added dropwise 50 mL of an aqueous 1% HCl solution to neutralize the reactant to 6-7. 100 mL of ethyl acetate was added to the reaction solution, the mixture was stirred for 30 minutes, and the organic layer was separated. The organic layer was washed with H 2 O. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
  • reaction solution was cooled to room temperature, 30 mL of H 2 O was added thereto, followed by stirring for about 30 minutes, and 40 mL of 1% HCl aqueous solution was slowly added dropwise to neutralize the pH of the reaction product to 6-7. 100 mL of ethyl acetate was added to the reaction solution, the mixture was stirred for 30 minutes, and the organic layer was separated. The organic layer was washed with H 2 O. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure.
  • methacrylic acid, styrene, methylmethacrylic acid, and cyclohexyl methacrylic acid were added in a molar ratio of 40: 20: 20: 20, respectively.
  • a binder of acrylic polymer having an acrylic unsaturated bond in the side chain was added by adding 20 molar ratios of glycidylmethacrylic acid to 0.3 g of N, N -dimethylaniline and 100 moles of solids of all monomers in the reactor.
  • Resin 2 was prepared.
  • the weight average molecular weight of polystyrene reduced by gel permeation chromatography (GPC) of the copolymer thus prepared was 20, 000 and the degree of dispersion was 2.0.
  • glycidylmethacrylic acid, styrene, methylmethacrylic acid and cyclohexylmethacrylic acid were each acrylic in a molar ratio of 40: 20: 20: 20.
  • a solid content of the monomer was added at 40% by weight, and then polymerized by stirring with stirring at 70 ° C. for 5 hours under a nitrogen atmosphere.
  • 0.3 g of N, N -dimethylaniline and 20 molar ratios of acrylic acid were added to 100 moles of solids of the entire monomer, followed by stirring at 100 ° C.
  • binder resin 3 an acrylic polymer having an acrylic unsaturated bond in the side chain. It was.
  • the weight average molecular weight of polystyrene reduced by gel permeation chromatography (GPC) of the copolymer thus prepared was 18,000, and the degree of dispersion was found to be 1.8.
  • Binder resins 1 to 3 according to the components and contents shown in Table 1 below in the reaction mixing tank equipped with the ultraviolet shielding film and the stirrer; Photoreactive compounds; Photopolymerization initiator of the present invention; And FC-430 (a 3M leveling agent) were added sequentially, stirred at room temperature, and PGMEA was added to the solvent so that the composition totaled 100% by weight to prepare a photoresist composition.
  • a red photoresist composition was prepared in the same manner except that 50 wt% of Pigment Red 177 (PR 177) dispersion having a solid content of 25 wt% was used instead of carbon black in Example 44. .
  • a photoresist composition was prepared in the same manner as in Example 27, except that Compound 4 was used instead of Compound 4 as a photopolymerization initiator.
  • the photoresist was spin coated on a glass substrate, dried on a hot plate at 100 ° C. for 1 minute, exposed using a step mask, and then developed in a 0.04% KOH aqueous solution. Sensitivity was evaluated for the exposure amount in which the step mask pattern maintains 80% of the initial thickness.
  • the photoresist composition was applied onto the substrate using a spin coater, then prebaked at 100 ° C. for 1 minute, exposed at 365 nm, and post-baked at 230 ° C. for 20 minutes to form a resist film.
  • the thickness ratio (%) before and after the postbaking was measured.
  • the silicon wafer in which the photoresist pattern was formed was cut
  • the pattern side wall was erected at an angle of 55 degrees or more with respect to the substrate, the film was not reduced, and it was determined as 'good', and the reduction of the film was judged as 'film'.
  • the resist film formed through a process such as prebake and postbake was immersed in a stripper solution for 10 minutes at 40 ° C., and then The change in transmittance and thickness was examined. When the change in transmittance and thickness is 2% or less, it is set as 'good', and when the change in transmittance and thickness is 2% or more, it is determined as 'poor'.
  • the photoresist composition was prebaked at 100 ° C. for 1 minute, exposed to the sensitivity of the photoresist, and then developed with a KOH aqueous solution to form a pattern of 20 um x 20 um. .
  • the formed pattern was crosslinked by postbake at 230 ° C. for 20 minutes, and the ductility was measured using a nano indentor. The measurement of the nanoindenter was determined to be 'good' if the total variation was more than 500 nm with 5 g.f loading, and 'bad' if it was less than 500 nm.
  • Example Sensitivity (mJ / cm 2 ) Residual rate (%) Pattern stability Chemical resistance ductility 27 45 91 Good Good Good 28 50 92 Good Good Good 29 45 91 Good Good Good 30 35 93 Good Good Good 31 45 93 Good Good 32 40 91 Good Good Good 33 40 91 Good Good Good 34 45 90 Good Good Good 35 50 92 Good Good Good 36 50 90 Good Good Good 37 50 89 Good Good Good 38 30 93 Good Good 39 45 91 Good Good Good 40 45 90 Good Good Good Good 41 40 93 Good Good Good Good 42 35 90 Good Good Good Good 43 40 90 Good Good Good Good 44 35 92 Good Good Good 45 40 91 Good Good Good Good Comparative Example 1 200 87 Film Bad Good Comparative Example 2 250 80 Film Bad Bad Bad
  • Dioxime ester compound according to the present invention from Table 2 is excellent in sensitivity even when using a small amount when used as a photopolymerization initiator of the photoresist composition, excellent properties such as residual film ratio, pattern stability, chemical resistance and ductility TFT- It was confirmed that the outgassing generated from the photopolymerization initiator can be minimized in the exposure and post-baking processes during the LCD manufacturing process, thereby reducing contamination and minimizing the defects that may occur.
  • the dioxime ester compound of the present invention When used as a photoinitiator of the photoresist composition, the dioxime ester compound of the present invention has excellent sensitivity even when used in a small amount, and has excellent physical properties such as residual film ratio, pattern stability, chemical resistance, and ductility. And it is possible to minimize the outgassing from the photopolymerization initiator in the post-baking process can reduce the contamination and there is an advantage that can minimize the defects that can be caused by this.

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Abstract

La présente invention concerne un nouveau composé dioximester et un amorceur de photopolymérisation et une composition de résine photosensible contenant ce composé.
PCT/KR2016/000635 2015-01-26 2016-01-21 Nouveau composé dioximester et amorceur de photopolymérisation et composition de résine photosensible contenant ce composé WO2016122160A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20190103370A (ko) * 2017-02-17 2019-09-04 창저우 트론리 어드벤스드 일렉트로닉 머티어리얼스 컴퍼니, 리미티드 플루오레닐아미노케톤 광개시제, 이의 제조 방법 및 이를 함유하는 uv 광경화성 조성물

Families Citing this family (1)

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Publication number Priority date Publication date Assignee Title
CN115160249B (zh) * 2022-06-23 2024-04-02 济南立德医药技术有限公司 一种5-甲基-3,4-二苯基异噁唑的制备方法

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20000006480A (ko) * 1998-06-26 2000-01-25 에프. 아. 프라저, 에른스트 알테르 (에. 알테르), 한스 페터 비틀린 (하. 페. 비틀린), 피. 랍 보프, 브이. 스펜글러, 페. 아에글러 신규ｏ-아실옥심광개시제
JP2001302871A (ja) * 2000-04-25 2001-10-31 Taiyo Ink Mfg Ltd 光硬化性・熱硬化性樹脂組成物とこれを用いて形成したソルダーレジスト皮膜や樹脂絶縁層を有するプリント配線板
JP2007256845A (ja) * 2006-03-24 2007-10-04 Fujifilm Corp 感光性組成物、感光性フィルム、永久パターン形成方法、及びプリント基板
JP2007298538A (ja) * 2006-04-27 2007-11-15 Fujifilm Corp 感光性組成物、感光性フィルム、永久パターン形成方法、及びプリント基板

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1395615B1 (fr) 2001-06-11 2009-10-21 Basf Se Photoamorceurs d'oxime ester possedant une structure combinee
TW200714651A (en) 2002-10-28 2007-04-16 Mitsubishi Chem Corp Photopolymerization composition and color filter using the same
JP4595374B2 (ja) 2003-04-24 2010-12-08 住友化学株式会社 黒色感光性樹脂組成物
JP3798008B2 (ja) 2004-12-03 2006-07-19 旭電化工業株式会社 オキシムエステル化合物及び該化合物を含有する光重合開始剤
EP1963374B1 (fr) 2005-12-20 2010-02-17 Basf Se Photoinitiateurs de type ester d'oxime
EP2128132B1 (fr) 2006-12-27 2014-01-15 Adeka Corporation Composé ester d'oxime et initiateur de photopolymérisation contenant le même
US8349548B2 (en) 2007-05-11 2013-01-08 Basf Se Oxime ester photoinitiators
CN101855201B (zh) 2007-12-25 2013-09-18 株式会社艾迪科 肟酯化合物及含有该化合物的光聚合引发剂
US8391887B2 (en) 2010-08-13 2013-03-05 Research In Motion Limited Methods and apparatus to activate location measurements
EP2625166B1 (fr) 2010-10-05 2014-09-24 Basf Se Dérivés ester d'oxime de composés benzocarbazole et leur utilisation comme photoinitiateurs dans des compositions photopolymérisables
CN103819583B (zh) * 2014-03-18 2016-05-18 常州强力电子新材料股份有限公司 一种含硝基双肟酯类光引发剂及其制备方法和应用

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20000006480A (ko) * 1998-06-26 2000-01-25 에프. 아. 프라저, 에른스트 알테르 (에. 알테르), 한스 페터 비틀린 (하. 페. 비틀린), 피. 랍 보프, 브이. 스펜글러, 페. 아에글러 신규ｏ-아실옥심광개시제
JP2001302871A (ja) * 2000-04-25 2001-10-31 Taiyo Ink Mfg Ltd 光硬化性・熱硬化性樹脂組成物とこれを用いて形成したソルダーレジスト皮膜や樹脂絶縁層を有するプリント配線板
JP2007256845A (ja) * 2006-03-24 2007-10-04 Fujifilm Corp 感光性組成物、感光性フィルム、永久パターン形成方法、及びプリント基板
JP2007298538A (ja) * 2006-04-27 2007-11-15 Fujifilm Corp 感光性組成物、感光性フィルム、永久パターン形成方法、及びプリント基板

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20190103370A (ko) * 2017-02-17 2019-09-04 창저우 트론리 어드벤스드 일렉트로닉 머티어리얼스 컴퍼니, 리미티드 플루오레닐아미노케톤 광개시제, 이의 제조 방법 및 이를 함유하는 uv 광경화성 조성물
KR102252495B1 (ko) 2017-02-17 2021-05-14 창저우 트론리 어드벤스드 일렉트로닉 머티어리얼스 컴퍼니, 리미티드 플루오레닐아미노케톤 광개시제, 이의 제조 방법 및 이를 함유하는 uv 광경화성 조성물

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