WO2013165207A1 - 신규한 옥심에스테르 플로렌 화합물, 이를 포함하는 광중합 개시제 및 포토레지스트 조성물 - Google Patents
신규한 옥심에스테르 플로렌 화합물, 이를 포함하는 광중합 개시제 및 포토레지스트 조성물 Download PDFInfo
- Publication number
- WO2013165207A1 WO2013165207A1 PCT/KR2013/003847 KR2013003847W WO2013165207A1 WO 2013165207 A1 WO2013165207 A1 WO 2013165207A1 KR 2013003847 W KR2013003847 W KR 2013003847W WO 2013165207 A1 WO2013165207 A1 WO 2013165207A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hydroxy
- butyl
- photoresist composition
- alkyl
- meth
- Prior art date
Links
Classifications
-
- 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
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/46—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms
- C07C323/47—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having at least one of the nitrogen atoms, not being part of nitro or nitroso groups, further bound to other hetero atoms to oxygen atoms
-
- 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- 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
- G03F7/09—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
-
- 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
- G03F7/20—Exposure; Apparatus therefor
-
- 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
- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
- G03F7/2014—Contact or film exposure of light sensitive plates such as lithographic plates or circuit boards, e.g. in a vacuum frame
- G03F7/2016—Contact mask being integral part of the photosensitive element and subject to destructive removal during post-exposure processing
- G03F7/202—Masking pattern being obtained by thermal means, e.g. laser ablation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
Definitions
- the present invention relates to a novel oxime ester florene 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, is easy to manufacture, has high thermal stability and storage stability, and is easy to handle and can be used in solvents (PGMEA; propylene glycol monomethyl ether acetate).
- PMEA 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. BACKGROUND ART
- Many studies have been conducted on photoresist compositions containing high-sensitivity photoinitiators capable of pattern formation with color resists and black matrices.
- a photoresist composition containing a binder resin, a polyfunctional monomer having an ethylenically unsaturated bond, and a photoinitiator is preferred.
- an object of the present invention is to provide a novel oxime ester florene compound, a photopolymerization initiator containing the same, and a photoresist composition having a higher sensitivity even when the amount thereof is reduced.
- the present invention provides a compound represented by the following formula (1) and 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 or (C 3 -C 20 ) cycloalkyl;
- A is hydrogen, (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, amino, nitro, cyano or hydroxy.
- Substituents including the "alkyl”, “alkoxy” and other “alkyl” moieties described in the present invention include all linear or pulverized forms, and "cycloalkyl” includes not only a single ring system but also various ring hydrocarbons.
- "Aryl” described in the present invention is an organic radical derived from an aromatic hydrocarbon by one hydrogen removal, and is a single or fused ring containing 4 to 7, preferably 5 or 6 ring atoms in each ring as appropriate. It includes a system, including a form in which a plurality of aryl is connected by a single bond.
- Hydroxyalkyl means OH-alkyl in which a hydroxy group is bonded to the alkyl group defined above, and "hydroxyalkoxyalkyl” means hydroxyalkyl- O -alkyl in which an alkoxy group is bonded to the hydroxyalkyl group.
- 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 (C 1 -C 4 ) 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.
- 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, hydroxymethyl, hydroxyethyl, hydroxy n -propyl, hydroxy n -butyl, hydroxy i -butyl, hydroxy n -pentyl, hydroxy i -penty
- A is hydrogen, methyl, ethyl, n -propyl, i -propyl, n -butyl, i -butyl, t -butyl, phenyl, naphthyl, biphenyl, terphenyl anthryl, indenyl, phenanthryl, methoxy, Ethoxy, propyloxy, butoxy, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxymethoxymethyl, hydroxymethoxyethyl, hydroxymethoxypropyl, hydroxymethoxybutyl, hydroxy Hydroxyethoxymethyl, hydroxyethoxyethyl, hydroxyethoxypropyl, hydroxyethoxybutyl, amino, nitro, cyano or hydroxy, but is not limited thereto.
- R 1 is hydrogen or n -butyl
- R 2 is methyl
- R 3 may be methyl, n -butyl or phenyl.
- Examples of the oxime ester florene derivative compounds according to the present invention include the following compounds, but the following compounds do not limit the present invention.
- the oxime ester florene compound represented by Formula 1 according to the present invention may be prepared as shown in Scheme 1 below.
- the oxime ester florene compound represented by Chemical Formula 1 may be included in the photoresist composition as a photopolymerization initiator.
- the photoresist composition of the present invention comprises an oxime ester florene compound represented by the formula (1), an acrylic polymer or an acrylic polymer having an acrylic unsaturated bond in the side chain, a polymerizable compound having an ethylenically unsaturated bond, a solvent, and the like.
- Excellent thin film properties such as control and heat and chemical resistance.
- 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).
- the 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 carboxylic acid, and a carboxyl 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, such as glycidyl acrylate, glycidyl methacrylate, 3,4-epoxy.
- Acrylic monomer containing methyl groups such as butyl (meth) acrylate, 2,3-epoxycyclohexyl (meth) acrylate, 3,4-epoxycyclohexylmethyl (meth) acrylate, methyl (meth) acrylate, hexyl Alkyl (meth) acrylates, such as (meth) acrylate, cyclohexyl (meth) acrylate, isobonyl (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 ⁇ methyl 2 or 2 types of monomers, such
- the acrylic polymer used as the binder resin of the photoresist composition or the acrylic polymer having an acrylic unsaturated bond in the side chain is 3 to 50% by weight based on 100% by weight of the photoresist composition in order to control pattern properties and impart thin film properties such as heat resistance and chemical resistance. It is preferable to use%, it is preferable to use what the average molecular weight of an acrylic polymer is 2,000-300,000, and dispersion degree is 1.0-10.0, and it is more preferable to use what is average molecular weight 4,000-100,000.
- 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 may be contained in an amount of 0.001 to 40 molar ratio based on 100 moles of the entire monomer solid content of the acrylic polymer used as the binder resin of the present invention or the acrylic polymer having an acrylic unsaturated bond in the side chain. .
- 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
- the amount of the oxime ester florene compound used as the photoinitiator in the photoresist composition of the present invention is 0.01 to 10% by weight, preferably 0.1 to 10% by weight based on 100% by weight of the photoresist composition as a content for increasing transparency and minimizing the exposure amount. It is more effective to use 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 compound may be further included in the photoresist composition to improve adhesion between the ITO electrode and the photoresist composition and to 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) ethy
- 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 on a substrate by adding a solvent, a pattern is formed by irradiating ultraviolet rays using a mask and developing with an alkaline developer. 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 methyl ether acetate
- PMEP propylene glycol methyl ether propionate
- EEP ethyl lactate
- PMEA propylene glycol methyl ether propionate
- PMEP propylene glycol methyl ether
- propylene glycol 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-pyrrolidone (NMP), ⁇ -butyrolactone
- diethyl ether ethylene glycol dimethyl ether, diglyme, tetrahydrofuran (THF)
- Methanol ethanol,
- the oxime ester florene derivative compound of the present invention When used as a photoinitiator of the photoresist composition, the oxime ester florene derivative compound of the present invention has excellent sensitivity even in small amounts, and has excellent physical properties such as residual film ratio, pattern stability, chemical resistance, and ductility. Outgassing from the photoinitiator can be minimized in the exposure and post-baking process, thereby reducing contamination and minimizing defects that may occur.
- Binder resins 1 to 2 according to the components and contents shown in Table 1 below in the reaction mixing tank equipped with the UV blocking film and the stirrer; Photoreactive compounds; Compounds 8, 9, 10, 14 as photoinitiators; And FC-430 (3M leveling agent, 0.1% by weight) was added sequentially, stirred at room temperature, and PGMEA was added to 100% by weight as a solvent to prepare a photoresist composition.
- binder resin 1 20 wt% of binder resin 1, 10 wt% of dipentaerythritol hexaacrylate, 0.5 wt% of compound 9, and 25 wt% of solids in propylene glycol methyl ether acetate in a reaction tank equipped with a sunscreen and a stirrer.
- 50% by weight of carbon black dispersed in ether acetate (PGMEA) and FC-430 (3M leveling agent, 0.1% by weight) were added sequentially, stirred at room temperature, and then PGMEA was added as a solvent so that the whole was 100% by weight.
- Black Matrix photoresist compositions were prepared.
- Red photoresist composition was prepared in the same manner as in Example 17, except that 50 wt% of Pigment Red 177 (P.R. 177) dispersion having a solid content of 25 wt% was used instead of carbon black.
- a photoresist composition was prepared in the same manner as in Example 7, except that 1,2-Octanedione-1- [4- (phenylthio) phenyl] -2- (O-benzoyloxime) was used as a photoinitiator instead of compound 8. Prepared.
- a photoresist composition was prepared in the same manner as in Example 7, except that the photoinitiator of Compound 21 was used instead of Compound 8 as the photoinitiator.
- a photoresist composition was prepared in the same manner as in Example 7, except that the photoinitiator of Compound 22 was used instead of Compound 8 as the photoinitiator.
- a photoresist composition was prepared in the same manner as in Example 7, except that the photoinitiator of the following compound 23 was used instead of the compound 8 as a photoinitiator.
- 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 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 postbaked at 230 ° C. for 20 minutes to post the resist film. The thickness ratio (%) before and after baking 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 at 40 ° C. for 10 minutes, 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 spin coater After applying the spin coater to the photoresist composition on the substrate, prebaked for 1 minute at 100 °C, 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 nano indentor was determined to be 'good' when the total variation was over 500 nm with 5 g.f loading, and 'bad' when it was below 500 nm.
- the oxime ester florene derivative compounds according to the present invention and the photoresist composition using the same as the photopolymerization initiator do not include a florene group and the photoresist composition using the same as the photopolymerization initiator (Comparative Examples 1 to 1).
- the sensitivity was much better and the physical properties such as residual film ratio, pattern stability, chemical resistance and ductility were excellent. Therefore, outgassing generated from photoinitiator during exposure and post-baking process during TFT-LCD manufacturing process was observed. It can be minimized to reduce contamination and bring the advantages of minimizing the defects that may occur.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Optics & Photonics (AREA)
- Materials For Photolithography (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Polymerisation Methods In General (AREA)
Abstract
Description
실시예 | 바인더 수지(중량%) | 광반응성 화합물(중량%) | 광개시제(중량%) | 첨가제(중량%) |
7 | 1 (40) | 디펜타에리스리톨헥사아크릴레이트 (20) | 화합물 8(0.5) | FC-430(0.1) |
8 | 1 (40) | 펜타에리스리톨트리아크릴레이트 (20) | 화합물 9(0.5) | FC-430(0.1) |
9 | 1 (40) | 트리메틸올프로판트리아크릴레이트 (10) 에틸렌글리콜디아크릴레이트 (10) | 화합물 10(0.5) | FC-430(0.1) |
10 | 1 (40) | 디펜타에리스리톨펜타아크릴레이트 (20) | 화합물 14(0.5) | FC-430(0.1) |
11 | 1 (40) | 비스페놀 A 디글리시딜에테르아크릴산 부가물 (20) | 화합물 8(0.5) | FC-430(0.1) |
12 | 2 (40) | 트리메틸올프로판트리아크릴레이트 (20) | 화합물 9(0.5) | FC-430(0.1) |
13 | 2 (40) | 펜타에리스리톨트리아크릴레이트 (20) | 화합물 10(0.5) | FC-430(0.1) |
14 | 2 (40) | 에틸렌그리콜디메타아크릴레이트 (20) | 화합물 14(0.5) | FC-430(0.1) |
15 | 1 (20)2 (20) | 디펜타에리스리톨헥사아크릴레이트 (20) | 화합물 8(0.5) | FC-430(0.1) |
16 | 1 (20)2 (20) | 펜타에리스리톨테트라아크릴레이트 (20) | 화합물 9(0.5) | FC-430(0.1) |
17 | 1 (20) | 디펜타에리스리톨헥사아크릴레이트 (10) | 화합물 9(0.5) | FC-430 (0.1)카본블랙 (50) |
18 | 1 (20) | 디펜타에리스리톨헥사아크릴레이트 (10) | 화합물 9(0.5) | FC-430 (0.1)P.R.177 (50) |
구분 | 감도 (mJ/cm2) | 잔막율(%) | 패턴안정성 | 내화학성 | 연성 |
실시예 7 | 40 | 91 | 양호 | 양호 | 양호 |
실시예 8 | 50 | 92 | 양호 | 양호 | 양호 |
실시예 9 | 45 | 91 | 양호 | 양호 | 양호 |
실시예 10 | 55 | 90 | 양호 | 양호 | 양호 |
실시예 11 | 35 | 93 | 양호 | 양호 | 양호 |
실시예 12 | 40 | 91 | 양호 | 양호 | 양호 |
실시예 13 | 40 | 91 | 양호 | 양호 | 양호 |
실시예 14 | 50 | 92 | 양호 | 양호 | 양호 |
실시예 15 | 30 | 93 | 양호 | 양호 | 양호 |
실시예 16 | 35 | 93 | 양호 | 양호 | 양호 |
실시예 17 | 60 | 90 | 양호 | 양호 | 양호 |
실시예 18 | 60 | 91 | 양호 | 양호 | 양호 |
비교예 1 | 200 | 87 | 막감 | 불량 | 양호 |
비교예 2 | 80 | 88 | 양호 | 불량 | 불량 |
비교예 3 | 120 | 84 | 막감 | 불량 | 양호 |
비교예 4 | 100 | 85 | 막감 | 불량 | 양호 |
Claims (8)
- 하기 화학식 1로 표시되는 옥심에스테르 플로렌유도체 화합물:[화학식 1]상기 화학식 1에서,R1 내지 R3는 각각 독립적으로 수소, 할로겐, (C1-C20)알킬, (C6-C20)아릴, (C1-C20)알콕시, (C6-C20)아릴(C1-C20)알킬, 히드록시(C1-C20)알킬, 히드록시(C1-C20)알콕시(C1-C20)알킬 또는 (C3-C20)사이클로알킬이고;A는 수소, (C1-C20)알킬, (C6-C20)아릴, (C1-C20)알콕시, (C6-C20)아릴(C1-C20)알킬, 히드록시(C1-C20)알킬, 히드록시(C1-C20)알콕시(C1-C20)알킬, (C3-C10)사이클로알킬, 아미노, 니트로, 시아노 또는 히드록시이다.
- 제 1항에 있어서,상기 R1 내지 R3는 각각 독립적으로 수소, 브로모, 클로로, 아이오도, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, n-펜틸, i-펜틸, n-헥실, i-헥실, 페닐, 나프틸, 바이페닐, 터페닐, 안트릴, 인데닐, 페난트릴, 메톡시, 에톡시, n-프로필옥시, i-프로필옥시, n-부톡시, i-부톡시, t-부톡시, 히드록시메틸, 히드록시에틸, 히드록시n-프로필, 히드록시n-부틸, 히드록시i-부틸, 히드록시n-펜틸, 히드록시i-펜틸, 히드록시n-헥실, 히드록시i-헥실, 히드록시메톡시메틸, 히드록시메톡시에틸, 히드록시메톡시프로필, 히드록시메톡시부틸, 히드록시에톡시메틸, 히드록시에톡시에틸, 히드록시에톡시프로필, 히드록시에톡시부틸, 히드록시에톡시펜틸 또는 히드록시에톡시헥실이고;A는 수소, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, 페닐, 나프틸, 바이페닐, 터페닐 안트릴, 인데닐, 페난트릴, 메톡시, 에톡시, 프로필옥시, 부톡시, 히드록시메틸, 히드록시에틸, 히드록시프로필, 히드록시부틸, 히드록시메톡시메틸, 히드록시메톡시에틸, 히드록시메톡시프로필, 히드록시메톡시부틸, 히드록시에톡시메틸, 히드록시에톡시에틸, 히드록시에톡시프로필, 히드록시에톡시부틸, 아미노, 니트로, 시아노 또는 히드록시인 것을 특징으로 하는 옥심에스테르 플로렌유도체 화합물.
- 제 1항에 있어서,상기 R1은 수소 또는 n-부틸이고;R2는 메틸이며;R3는 메틸, n-부틸 또는 페닐인 것을 특징으로 하는 옥심에스테르 플로렌유도체 화합물.
- 제 1항 내지 제 3항에서 선택되는 어느 한 항의 옥심에스테르 플로렌유도체 화합물을 포함하는 광중합 개시제.
- 제 1항 내지 제 3항에서 선택되는 어느 한 항의 옥심에스테르 플로렌유도체 화합물을 포함하는 포토레지스트 조성물.
- 제 5항에 있어서,상기 옥심에스테르 플로렌유도체 화합물은 포토 레지스트 조성물에 대하여 0.01 내지 10 중량%로 포함되는 것을 특징으로 하는 포토레지스트 조성물.
- 제 5항의 포토레지스트 조성물에 카본블랙을 더 포함하는 블랙 매트릭스용 포토레지스트 조성물.
- 제 5항의 포토레지스트 조성물에 컬러 안료 분산액을 더 포함하는 컬러매트릭스용 포토레지스트 조성물.
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015510191A JP6127130B2 (ja) | 2012-05-03 | 2013-05-03 | 新規のオキシムエステルフルオレン化合物、およびこれを含む光重合開始剤、並びにフォトレジスト組成物 |
EP13785166.3A EP2845845B1 (en) | 2012-05-03 | 2013-05-03 | Novel oximester fluorine compound, and photopolymerization initiator and photoresist composition comprising same |
CN201380024274.8A CN104661997B (zh) | 2012-05-03 | 2013-05-03 | 新型芴类肟酯化合物,及含有该芴类肟酯化合物的光聚合引发剂和光阻剂组合物 |
US14/398,565 US9316906B2 (en) | 2012-05-03 | 2013-05-03 | Fluorene oxime ester compound, photopolymerization initiator and photoresist composition containing the same |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2012-0047095 | 2012-05-03 | ||
KR20120047095 | 2012-05-03 | ||
KR1020130049811A KR101518774B1 (ko) | 2012-05-03 | 2013-05-03 | 신규한 옥심에스테르 플로렌 화합물, 이를 포함하는 광중합 개시제 및 포토레지스트 조성물 |
KR10-2013-0049811 | 2013-05-03 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2013165207A1 true WO2013165207A1 (ko) | 2013-11-07 |
Family
ID=49853242
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/KR2013/003847 WO2013165207A1 (ko) | 2012-05-03 | 2013-05-03 | 신규한 옥심에스테르 플로렌 화합물, 이를 포함하는 광중합 개시제 및 포토레지스트 조성물 |
Country Status (7)
Country | Link |
---|---|
US (1) | US9316906B2 (ko) |
EP (1) | EP2845845B1 (ko) |
JP (1) | JP6127130B2 (ko) |
KR (1) | KR101518774B1 (ko) |
CN (1) | CN104661997B (ko) |
TW (1) | TWI472507B (ko) |
WO (1) | WO2013165207A1 (ko) |
Cited By (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103819583A (zh) * | 2014-03-18 | 2014-05-28 | 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 |
JP2014137466A (ja) * | 2013-01-16 | 2014-07-28 | Jsr Corp | 感放射線性着色組成物、着色硬化膜及び表示素子 |
JP2015045686A (ja) * | 2013-08-27 | 2015-03-12 | 凸版印刷株式会社 | 感光性樹脂組成物、カラーフィルタ及び液晶表示装置 |
JP2016519675A (ja) * | 2014-01-17 | 2016-07-07 | サムヤン コーポレーション | 新規なβ‐オキシムエステルフルオレン化合物、それを含む光重合開始剤及びフォトレジスト組成物 |
WO2016126070A1 (ko) * | 2015-02-06 | 2016-08-11 | 한국화학연구원 | 신규한 옥심에스테르 유도체 화합물 및 이를 포함하는 광중합 개시제 및 포토레지스트 조성물 |
JP2017008134A (ja) * | 2015-06-17 | 2017-01-12 | 東京応化工業株式会社 | 硬化性組成物、硬化物の製造方法、及びハードコート材 |
US20170160636A1 (en) * | 2014-07-15 | 2017-06-08 | Tokyo Ohka Kogyo Co., Ltd. | Photosensitive composition and compound |
US9684238B2 (en) * | 2012-09-28 | 2017-06-20 | Tokyo Ohka Kogyo Co., Ltd. | Fluorene-type compound, photopolymerization initiator comprising said fluorene-type compound, and photosensitive composition containing said photopolymerization initiator |
CN107111232A (zh) * | 2014-11-12 | 2017-08-29 | 三养社 | 用于液晶显示面板的黑色矩阵光致抗蚀剂组合物 |
CN107229186A (zh) * | 2016-03-24 | 2017-10-03 | 东友精细化工有限公司 | 着色感光性树脂组合物、包含其的滤色器和显示装置 |
KR20180063252A (ko) * | 2015-10-08 | 2018-06-11 | 샹조우 트론리 뉴 일렉트로닉 머티리얼즈 컴퍼니 리미티드 | 플루오렌 함유 옥심에스테르계 광개시제, 이의 합성, 이를 함유하는 감광성 수지 조성물 및 그 응용 |
US10976660B2 (en) | 2016-09-13 | 2021-04-13 | Changzhou Tronly Advanced Electronic Materials Co , Ltd. | Fluorene photoinitiator, preparation method therefor, photocurable composition having same, and use of same in photocuring field |
US11054743B2 (en) | 2015-12-15 | 2021-07-06 | Changzhou Tronly Advanced Electronic Materials Co., Ltd. | Fluorene polyfunctional photoinitiator and preparation and use thereof, and photosensitive resin composition containing fluorene photoinitiator and use thereof |
US11118065B2 (en) | 2017-02-17 | 2021-09-14 | Changzhou Tronly Advanced Electronic Materials Co., Ltd. | Fluorenylaminoketone photoinitiator, preparation method thereof, and UV photocurable composition containing same |
Families Citing this family (64)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10331032B2 (en) * | 2012-04-23 | 2019-06-25 | Brewer Science, Inc. | Photosensitive, developer-soluble bottom anti-reflective coating material |
JP2015014783A (ja) * | 2013-06-04 | 2015-01-22 | 日立化成株式会社 | 硬化膜付き透明基材の製造方法、感光性樹脂組成物、感光性エレメント、及び電子部品 |
WO2016076652A1 (ko) * | 2014-11-12 | 2016-05-19 | 주식회사 삼양사 | 액정디스플레이 패널용 블랙매트릭스 포토레지스트 조성물 |
KR102047079B1 (ko) | 2015-03-11 | 2019-12-02 | 동우 화인켐 주식회사 | 청색 감광성 수지 조성물, 컬러필터 및 이를 포함하는 액정표시장치 |
JP6195645B2 (ja) * | 2015-07-21 | 2017-09-13 | 東京応化工業株式会社 | 着色感光性組成物 |
CN108137443B (zh) * | 2015-07-31 | 2021-06-08 | 克美 | 芴衍生物、包含其的光聚合引发剂及光致抗蚀剂组合物 |
US10719016B2 (en) * | 2015-08-21 | 2020-07-21 | Asahi Kasei Kabushiki Kaisha | Photosensitive resin composition, polyimide production method, and semiconductor device |
CN106483760B (zh) * | 2015-09-02 | 2019-11-12 | 东京应化工业株式会社 | 感光性组合物、其制造方法、膜的形成方法、粘度增加抑制方法、光聚合引发剂及其制造方法 |
JP6894188B2 (ja) * | 2015-09-02 | 2021-06-30 | 東京応化工業株式会社 | 感光性組成物、当該感光性組成物の製造方法、当該感光性組成物を用いる膜の形成方法、感光性組成物の保管時の増粘抑制方法、光重合開始剤、及び光重合開始剤の製造方法 |
KR102108917B1 (ko) * | 2015-09-21 | 2020-05-11 | 동우 화인켐 주식회사 | 착색 감광성 수지 조성물 및 이를 이용하는 컬러 필터 |
KR101788399B1 (ko) * | 2015-09-23 | 2017-10-19 | (주)경인양행 | 내열안정성이 우수한 옥심 에스테르 화합물, 그것을 포함하는 광중합 개시제 및 감광성 수지 조성물 |
KR102466525B1 (ko) * | 2015-09-23 | 2022-11-11 | 주식회사 삼양사 | 신규한 비페닐 옥심 에스테르 유도체 화합물 및 이를 포함하는 광중합 개시제 및 포토레지스트 조성물 |
CN107272336A (zh) * | 2016-04-06 | 2017-10-20 | 常州强力先端电子材料有限公司 | 一种含芴类光引发剂的感光性树脂组合物及其应用 |
KR20170065111A (ko) * | 2015-12-03 | 2017-06-13 | 동우 화인켐 주식회사 | 착색 감광성 수지 조성물, 이를 이용하여 제조된 컬러필터 및 화상 표시 장치 |
CN106883114B (zh) * | 2015-12-15 | 2019-11-19 | 常州强力先端电子材料有限公司 | 一种芴类多官能度光引发剂及其制备和应用 |
KR20170084498A (ko) * | 2016-01-12 | 2017-07-20 | 동우 화인켐 주식회사 | 착색 감광성 수지 조성물, 컬러 필터 및 이를 구비한 화상 표시 장치 |
JP6517767B2 (ja) * | 2015-12-29 | 2019-05-22 | 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. | 着色感光性樹脂組成物、カラーフィルター及びこれを具備した画像表示装置 |
KR102345021B1 (ko) * | 2016-01-12 | 2021-12-28 | 동우 화인켐 주식회사 | 착색 감광성 수지 조성물, 컬러 필터 및 이를 구비한 화상 표시 장치 |
JP6788971B2 (ja) * | 2016-01-14 | 2020-11-25 | 東京応化工業株式会社 | 感光性組成物 |
KR102347918B1 (ko) * | 2016-03-28 | 2022-01-05 | 동우 화인켐 주식회사 | 착색 감광성 수지 조성물, 이를 이용하여 제조된 컬러필터 및 화상표시장치 |
KR102005346B1 (ko) * | 2016-05-24 | 2019-07-30 | 동우 화인켐 주식회사 | 감광성 수지 조성물 및 이로부터 제조되는 광경화 패턴 |
KR102493611B1 (ko) * | 2016-06-14 | 2023-01-31 | 동우 화인켐 주식회사 | 적색 감광성 수지 조성물, 이를 포함하는 컬러필터 및 표시장치 |
CN109134712B (zh) * | 2017-06-28 | 2020-05-19 | 常州强力先端电子材料有限公司 | 芴类多官能度光引发剂、其制备方法及其应用 |
KR102458810B1 (ko) | 2016-09-28 | 2022-10-26 | 메르크 파텐트 게엠베하 | 중합가능 액정 물질 및 중합된 액정 필름 |
KR101986408B1 (ko) * | 2016-11-08 | 2019-06-05 | 동우 화인켐 주식회사 | 착색 감광성 수지 조성물, 컬러필터 및 화상표시장치 |
KR102615683B1 (ko) * | 2016-11-16 | 2023-12-18 | 동우 화인켐 주식회사 | 감광성 수지 조성물 및 이로부터 형성된 광경화 패턴 |
KR101848567B1 (ko) * | 2016-11-18 | 2018-04-12 | 롬엔드하스전자재료코리아유한회사 | 착색 감광성 수지 조성물 및 이로부터 제조된 차광성 스페이서 |
KR101834209B1 (ko) * | 2016-11-25 | 2018-03-06 | 주식회사 삼양사 | 광중합 개시제 및 이를 포함하는 차광용 감광성 수지 조성물 |
KR102121424B1 (ko) * | 2016-12-02 | 2020-06-10 | 삼성에스디아이 주식회사 | 감광성 수지 조성물, 이를 이용한 블랙 화소 격벽층 및 디스플레이 장치 |
KR101991838B1 (ko) * | 2016-12-28 | 2019-06-24 | 주식회사 삼양사 | 신규 1,3-벤조디아졸 베타-옥심 에스테르 화합물 및 이를 포함하는 조성물 |
KR102510668B1 (ko) * | 2017-02-01 | 2023-03-16 | 동우 화인켐 주식회사 | 착색 감광성 수지 조성물, 이를 이용하여 제조된 컬러필터 및 화상표시장치 |
JP6813399B2 (ja) * | 2017-03-10 | 2021-01-13 | 東京応化工業株式会社 | 硬化膜を形成する方法及びめっき造形物の製造方法 |
JP6813398B2 (ja) * | 2017-03-10 | 2021-01-13 | 東京応化工業株式会社 | 感光性組成物、ドライフィルム、及びパターン化された硬化膜を形成する方法 |
US20180259850A1 (en) * | 2017-03-10 | 2018-09-13 | Tokyo Ohka Kogyo Co., Ltd. | Method for forming patterned cured film, photosensitive composition, dry film, and method for producing plated shaped article |
KR102033415B1 (ko) * | 2017-03-17 | 2019-10-17 | 동우 화인켐 주식회사 | 적색 화소용 착색 감광성 수지 조성물, 컬러필터 및 화상표시장치 |
JP7034175B2 (ja) * | 2017-04-25 | 2022-03-11 | 常州強力先端電子材料有限公司 | 重合可能基含有フルオレンオキシムエステル系光開始剤、製造方法およびその応用 |
CN108727517B (zh) * | 2017-04-25 | 2021-05-07 | 常州强力先端电子材料有限公司 | 含有可聚合基团的芴肟酯类光引发剂、其制备方法及应用 |
CN109459914B (zh) * | 2017-09-06 | 2021-07-13 | 常州强力先端电子材料有限公司 | 光固化树脂组合物及其应用 |
KR20180135370A (ko) * | 2017-06-12 | 2018-12-20 | 롬엔드하스전자재료코리아유한회사 | 착색 감광성 수지 조성물 및 이로부터 제조된 차광성 스페이서 |
JP6437050B2 (ja) * | 2017-06-15 | 2018-12-12 | 東京応化工業株式会社 | 感光性組成物、パターン形成方法、硬化膜、絶縁膜、及び表示装置 |
JP7051321B2 (ja) * | 2017-07-21 | 2022-04-11 | 東京応化工業株式会社 | 感光性組成物、パターン形成方法、硬化物、及び表示装置 |
CN107445860A (zh) * | 2017-08-04 | 2017-12-08 | 吴赣药业(苏州)有限公司 | 一种2‑乙酰肟基‑9,9‑二乙基芴的制备方法 |
CN107459469A (zh) * | 2017-08-04 | 2017-12-12 | 吴赣药业(苏州)有限公司 | 一种2,7‑二乙酰肟基‑9,9‑二丁基芴的制备方法 |
CN107445861A (zh) * | 2017-08-04 | 2017-12-08 | 吴赣药业(苏州)有限公司 | 一种2‑硝基‑7‑乙酰肟基‑9,9‑二丁基芴的制备方法 |
JP7430631B2 (ja) * | 2017-08-15 | 2024-02-13 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | 重合性液晶材料および重合した液晶フィルム |
JP7079581B2 (ja) * | 2017-08-31 | 2022-06-02 | 東京応化工業株式会社 | 感光性組成物、硬化物形成方法、硬化物、画像表示装置用パネル、及び画像表示装置 |
JP6968633B2 (ja) * | 2017-09-07 | 2021-11-17 | 東京応化工業株式会社 | 感光性組成物、及びそれに用いられる光重合開始剤 |
KR102374880B1 (ko) * | 2017-09-29 | 2022-03-16 | 후지필름 가부시키가이샤 | 착색 감광성 조성물 및 광학 필터의 제조 방법 |
CN108117616B (zh) | 2017-11-22 | 2019-08-09 | 惠州市华泓新材料股份有限公司 | 二丁基芴基衍生物与其作为光引发剂的应用 |
KR102361560B1 (ko) * | 2017-12-22 | 2022-02-14 | 창저우 트론리 어드벤스드 일렉트로닉 머티어리얼스 컴퍼니, 리미티드 | 불소-함유 플루오렌 옥심 에스테르 광개시제, 이를 포함하는 광경화성 조성물, 및 이의 용도 |
CN109957046B (zh) * | 2017-12-22 | 2020-07-03 | 常州强力先端电子材料有限公司 | 含氟芴肟酯类光引发剂、包含其的光固化组合物及其应用 |
TW202003591A (zh) | 2018-04-27 | 2020-01-16 | 德商馬克專利公司 | 可聚合的液晶材料及經聚合的液晶膜 |
CN110471255B (zh) * | 2018-05-10 | 2022-05-06 | 东友精细化工有限公司 | 感光性树脂组合物、光固化图案及图像显示装置 |
EP3793750A4 (en) * | 2018-05-14 | 2022-06-22 | NBD Nanotechnologies, Inc. | ORGANOSILANE COATING COMPOSITIONS |
CN112189007B (zh) * | 2018-08-07 | 2023-07-04 | 株式会社艾迪科 | 氨基甲酰肟化合物以及含有该化合物的聚合引发剂及聚合性组合物 |
JP7175168B2 (ja) * | 2018-11-29 | 2022-11-18 | 東京応化工業株式会社 | 感光性樹脂組成物、パターン化された硬化膜の製造方法、及びパターン化された硬化膜 |
CN112010788B (zh) * | 2019-05-31 | 2022-10-21 | 常州强力先端电子材料有限公司 | 一种非离子型肟酯类光产酸剂 |
CN112279800B (zh) * | 2019-07-24 | 2022-12-09 | 常州强力电子新材料股份有限公司 | 增感化合物、感光性树脂组合物及各自的应用 |
CN113004738B (zh) * | 2019-12-19 | 2022-04-22 | 常州强力电子新材料股份有限公司 | 光固化组合物、光固化油墨 |
WO2021121135A1 (zh) * | 2019-12-19 | 2021-06-24 | 常州强力电子新材料股份有限公司 | 光引发剂、其制备方法及应用、光固化组合物 |
CN113004440B (zh) * | 2019-12-19 | 2022-05-10 | 常州强力电子新材料股份有限公司 | 光引发剂、其制备方法及应用、光固化组合物 |
KR102211634B1 (ko) * | 2020-04-29 | 2021-02-03 | 동우 화인켐 주식회사 | 착색 감광성 수지 조성물 및 이를 이용하는 컬러 필터 |
KR20240075890A (ko) * | 2021-11-09 | 2024-05-29 | 후지필름 가부시키가이샤 | 경화성 조성물, 경화물의 제조 방법, 막, 광학 소자, 이미지 센서, 고체 촬상 소자, 화상 표시 장치, 및, 라디칼 중합 개시제 |
CN114181110A (zh) * | 2021-12-10 | 2022-03-15 | 阜阳欣奕华材料科技有限公司 | 一种双酚芴肟酯光引发剂及其制备方法和应用 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20010012596A1 (en) * | 1999-12-15 | 2001-08-09 | Kazuhiko Kunimoto | Oxime ester photoinitiators |
US20090087759A1 (en) * | 2005-12-01 | 2009-04-02 | Akira Matsumoto | Oxime Ester Photoinitiators |
EP2072500A1 (en) * | 2006-12-27 | 2009-06-24 | Adeka Corporation | Oxime ester compound and photopolymerization initiator containing the compound |
US8133656B2 (en) * | 2006-12-27 | 2012-03-13 | Adeka Corporation | Oxime ester compound and photopolymerization initiator containing the same |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101007440B1 (ko) | 2007-07-18 | 2011-01-12 | 주식회사 엘지화학 | 옥심 에스테르를 포함하는 수지상 광활성 화합물 및 이의제조방법 |
JP2010015025A (ja) * | 2008-07-04 | 2010-01-21 | Adeka Corp | 特定の光重合開始剤を含有する感光性組成物 |
JP5573578B2 (ja) * | 2009-10-16 | 2014-08-20 | 信越化学工業株式会社 | パターン形成方法及びレジスト材料 |
JP5914379B2 (ja) * | 2012-03-02 | 2016-05-11 | 富士フイルム株式会社 | 着色硬化性組成物およびカラーフィルタ |
US9684238B2 (en) * | 2012-09-28 | 2017-06-20 | Tokyo Ohka Kogyo Co., Ltd. | Fluorene-type compound, photopolymerization initiator comprising said fluorene-type compound, and photosensitive composition containing said photopolymerization initiator |
JP2014134763A (ja) * | 2012-12-11 | 2014-07-24 | Jsr Corp | 感放射線性樹脂組成物、表示素子用硬化膜、表示素子用硬化膜の形成方法及び表示素子 |
JP6065596B2 (ja) * | 2013-01-16 | 2017-01-25 | Jsr株式会社 | 感放射線性着色組成物、着色硬化膜及び表示素子 |
JP2014182253A (ja) * | 2013-03-19 | 2014-09-29 | Toppan Printing Co Ltd | 黒色感光性樹脂組成物、カラーフィルタ及び液晶表示装置 |
-
2013
- 2013-05-03 JP JP2015510191A patent/JP6127130B2/ja active Active
- 2013-05-03 TW TW102115857A patent/TWI472507B/zh active
- 2013-05-03 US US14/398,565 patent/US9316906B2/en active Active
- 2013-05-03 KR KR1020130049811A patent/KR101518774B1/ko active IP Right Grant
- 2013-05-03 EP EP13785166.3A patent/EP2845845B1/en active Active
- 2013-05-03 WO PCT/KR2013/003847 patent/WO2013165207A1/ko active Application Filing
- 2013-05-03 CN CN201380024274.8A patent/CN104661997B/zh active Active
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20010012596A1 (en) * | 1999-12-15 | 2001-08-09 | Kazuhiko Kunimoto | Oxime ester photoinitiators |
US20090087759A1 (en) * | 2005-12-01 | 2009-04-02 | Akira Matsumoto | Oxime Ester Photoinitiators |
EP2072500A1 (en) * | 2006-12-27 | 2009-06-24 | Adeka Corporation | Oxime ester compound and photopolymerization initiator containing the compound |
US8133656B2 (en) * | 2006-12-27 | 2012-03-13 | Adeka Corporation | Oxime ester compound and photopolymerization initiator containing the same |
Cited By (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9684238B2 (en) * | 2012-09-28 | 2017-06-20 | Tokyo Ohka Kogyo Co., Ltd. | Fluorene-type compound, photopolymerization initiator comprising said fluorene-type compound, and photosensitive composition containing said photopolymerization initiator |
JP2014137466A (ja) * | 2013-01-16 | 2014-07-28 | Jsr Corp | 感放射線性着色組成物、着色硬化膜及び表示素子 |
JP2015045686A (ja) * | 2013-08-27 | 2015-03-12 | 凸版印刷株式会社 | 感光性樹脂組成物、カラーフィルタ及び液晶表示装置 |
JP2017061498A (ja) * | 2014-01-17 | 2017-03-30 | サムヤン コーポレーション | 新規なβ‐オキシムエステルフルオレン化合物、それを含む光重合開始剤及びフォトレジスト組成物 |
JP2016519675A (ja) * | 2014-01-17 | 2016-07-07 | サムヤン コーポレーション | 新規なβ‐オキシムエステルフルオレン化合物、それを含む光重合開始剤及びフォトレジスト組成物 |
US9873663B2 (en) | 2014-01-17 | 2018-01-23 | Samyang Corporation | Fluorenyl β-oxime ester compounds, photopolymerization initiator and photoresist composition containing the same |
CN103819583A (zh) * | 2014-03-18 | 2014-05-28 | 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 |
US10539872B2 (en) | 2014-07-15 | 2020-01-21 | Tokyo Ohka Kogyo Co., Ltd. | Photosensitive composition and compound |
JP2018072849A (ja) * | 2014-07-15 | 2018-05-10 | 東京応化工業株式会社 | 感光性組成物及び化合物 |
US20170160636A1 (en) * | 2014-07-15 | 2017-06-08 | Tokyo Ohka Kogyo Co., Ltd. | Photosensitive composition and compound |
EP3165965A4 (en) * | 2014-07-15 | 2017-08-02 | Tokyo Ohka Kogyo Co., Ltd. | Photosensitive composition and compound |
JP2017537347A (ja) * | 2014-11-12 | 2017-12-14 | サムヤン コーポレーション | 液晶ディスプレイパネル用ブラックマトリックスフォトレジスト組成物 |
CN107111232A (zh) * | 2014-11-12 | 2017-08-29 | 三养社 | 用于液晶显示面板的黑色矩阵光致抗蚀剂组合物 |
CN107250105A (zh) * | 2015-02-06 | 2017-10-13 | 韩国化学研究院 | 新型肟酯衍生物化合物、包含其的光聚合引发剂及光致抗蚀剂组合物 |
JP2018506532A (ja) * | 2015-02-06 | 2018-03-08 | コリア リサーチ インスティテュート オブ ケミカル テクノロジー | 新規のオキシムエステル誘導体化合物およびこれを含む光重合開始剤、ならびにフォトレジスト組成物 |
CN107250105B (zh) * | 2015-02-06 | 2019-08-20 | 韩国化学研究院 | 新型肟酯衍生物化合物、包含其的光聚合引发剂及光致抗蚀剂组合物 |
WO2016126070A1 (ko) * | 2015-02-06 | 2016-08-11 | 한국화학연구원 | 신규한 옥심에스테르 유도체 화합물 및 이를 포함하는 광중합 개시제 및 포토레지스트 조성물 |
JP2017008134A (ja) * | 2015-06-17 | 2017-01-12 | 東京応化工業株式会社 | 硬化性組成物、硬化物の製造方法、及びハードコート材 |
KR20180063252A (ko) * | 2015-10-08 | 2018-06-11 | 샹조우 트론리 뉴 일렉트로닉 머티리얼즈 컴퍼니 리미티드 | 플루오렌 함유 옥심에스테르계 광개시제, 이의 합성, 이를 함유하는 감광성 수지 조성물 및 그 응용 |
KR102189685B1 (ko) * | 2015-10-08 | 2020-12-14 | 샹조우 트론리 뉴 일렉트로닉 머티리얼즈 컴퍼니 리미티드 | 플루오렌 함유 옥심에스테르계 광개시제, 이의 합성, 이를 함유하는 감광성 수지 조성물 및 그 응용 |
US11054743B2 (en) | 2015-12-15 | 2021-07-06 | Changzhou Tronly Advanced Electronic Materials Co., Ltd. | Fluorene polyfunctional photoinitiator and preparation and use thereof, and photosensitive resin composition containing fluorene photoinitiator and use thereof |
CN107229186A (zh) * | 2016-03-24 | 2017-10-03 | 东友精细化工有限公司 | 着色感光性树脂组合物、包含其的滤色器和显示装置 |
CN107229186B (zh) * | 2016-03-24 | 2021-06-29 | 东友精细化工有限公司 | 着色感光性树脂组合物、包含其的滤色器和显示装置 |
US10976660B2 (en) | 2016-09-13 | 2021-04-13 | Changzhou Tronly Advanced Electronic Materials Co , Ltd. | Fluorene photoinitiator, preparation method therefor, photocurable composition having same, and use of same in photocuring field |
US11118065B2 (en) | 2017-02-17 | 2021-09-14 | Changzhou Tronly Advanced Electronic Materials Co., Ltd. | Fluorenylaminoketone photoinitiator, preparation method thereof, and UV photocurable composition containing same |
Also Published As
Publication number | Publication date |
---|---|
US9316906B2 (en) | 2016-04-19 |
US20150111152A1 (en) | 2015-04-23 |
EP2845845B1 (en) | 2019-07-03 |
KR101518774B1 (ko) | 2015-05-11 |
CN104661997B (zh) | 2018-06-26 |
JP6127130B2 (ja) | 2017-05-10 |
JP2015523318A (ja) | 2015-08-13 |
TW201345882A (zh) | 2013-11-16 |
EP2845845A1 (en) | 2015-03-11 |
CN104661997A (zh) | 2015-05-27 |
KR20130124215A (ko) | 2013-11-13 |
TWI472507B (zh) | 2015-02-11 |
EP2845845A4 (en) | 2015-12-09 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2013165207A1 (ko) | 신규한 옥심에스테르 플로렌 화합물, 이를 포함하는 광중합 개시제 및 포토레지스트 조성물 | |
JP6196363B2 (ja) | 新規なβ‐オキシムエステルフルオレン化合物、それを含む光重合開始剤及びフォトレジスト組成物 | |
KR101963931B1 (ko) | 흑색 감광성 수지 조성물, 이를 이용한 블랙매트릭스 및 이를 구비한 화상 표시 장치 | |
WO2016076652A1 (ko) | 액정디스플레이 패널용 블랙매트릭스 포토레지스트 조성물 | |
WO2018159975A1 (ko) | 고분자 수지 화합물 및 이를 포함하는 블랙 뱅크용 감광성 수지 조성물 | |
WO2013018986A1 (ko) | 염료를 포함하는 고분자 화합물 및 이를 포함하는 경화성 수지 조성물 | |
WO2020139042A2 (ko) | 카바졸 멀티 베타 옥심에스테르 유도체 화합물 및 이를 포함하는 광중합 개시제와 포토레지스트 조성물 | |
WO2018097580A1 (ko) | 광-개시제 및 이를 포함하는 차광용 감광성 수지 조성물 | |
WO2012064074A1 (en) | Photosensitive resin composition, and dielectric insulating film and electronic device using the same | |
WO2010041810A1 (ko) | 우레탄계 다관능성 모노머, 그의 제조방법 및 이를 포함하는 감광성 수지 조성물 | |
TWI603949B (zh) | 新穎肟酯聯苯基化合物、及含彼之光起始劑與光敏樹脂組合物 | |
WO2017209449A1 (ko) | 광활성 화합물, 이를 포함하는 광중합 개시제 및 포토레지스트 조성물 | |
WO2015163681A1 (ko) | 투명 플라스틱 기판용 수지 조성물 | |
KR101574535B1 (ko) | 신규한 옥심에스테르 비페닐 화합물, 이를 포함하는 광개시제 및 감광성 수지 조성물 | |
WO2019022447A1 (ko) | 카바졸 유도체, 이를 포함하는 광중합 개시제 및 포토레지스트 조성물 | |
KR101828927B1 (ko) | 신규한 옥심에스테르 화합물, 이를 포함하는 광중합 개시제 및 포토레지스트 조성물 | |
KR102466525B1 (ko) | 신규한 비페닐 옥심 에스테르 유도체 화합물 및 이를 포함하는 광중합 개시제 및 포토레지스트 조성물 | |
WO2021010683A1 (ko) | 감광성 수지 조성물 | |
WO2022177332A1 (ko) | 유기금속 화합물 및 폴리실록산 공중합체를 포함하는 감광성 조성물 및 그 제조방법 | |
KR101478292B1 (ko) | 신규한 β-옥심에스테르 비페닐 화합물, 이를 포함하는 광개시제 및 감광성 수지 조성물 | |
WO2021177654A1 (ko) | 신규한 옥심에스테르 카바졸 유도체 화합물 | |
WO2016204346A1 (ko) | 고분지형 덴드리틱 알칼리 가용성 바인더 수지와 이의 제조방법 및 이를 포함하는 감광성 수지 조성물 | |
WO2017131378A1 (ko) | 카바졸 유도체, 이를 포함하는 광중합 개시제 및 포토레지스트 조성물 | |
WO2021177653A1 (ko) | 신규한 옥심에스테르 카바졸 유도체 화합물 | |
KR102509606B1 (ko) | 신규한 퀴놀리닐 베타 옥심에스테르 유도체 화합물, 이를 포함하는 광중합 개시제, 및 포토레지스트 조성물 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 13785166 Country of ref document: EP Kind code of ref document: A1 |
|
ENP | Entry into the national phase |
Ref document number: 2015510191 Country of ref document: JP Kind code of ref document: A |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 14398565 Country of ref document: US |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2013785166 Country of ref document: EP |