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WO2016076652A1 - Composition de résine photosensible pour matrice à fond noir pour un panneau d'affichage à cristaux liquides - Google Patents

Composition de résine photosensible pour matrice à fond noir pour un panneau d'affichage à cristaux liquides Download PDF

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Publication number
WO2016076652A1
WO2016076652A1 PCT/KR2015/012191 KR2015012191W WO2016076652A1 WO 2016076652 A1 WO2016076652 A1 WO 2016076652A1 KR 2015012191 W KR2015012191 W KR 2015012191W WO 2016076652 A1 WO2016076652 A1 WO 2016076652A1
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Prior art keywords
hydroxy
alkyl
meth
acrylate
black matrix
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PCT/KR2015/012191
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English (en)
Korean (ko)
Inventor
오천림
김학준
최정식
김태운
안정민
이건표
조용일
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주식회사 삼양사
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Application filed by 주식회사 삼양사 filed Critical 주식회사 삼양사
Priority to CN201580073141.9A priority Critical patent/CN107111232A/zh
Priority to JP2017525535A priority patent/JP2017537347A/ja
Priority claimed from KR1020150158807A external-priority patent/KR101808818B1/ko
Publication of WO2016076652A1 publication Critical patent/WO2016076652A1/fr

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • 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
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements

Definitions

  • the present invention relates to a black matrix, which is a light-sensitive photosensitive resin composition used for a liquid crystal display. More specifically, the present invention relates to a photosensitive resin composition that can be used to prepare black matrices used in liquid crystal displays using photolithography.
  • the black matrix photoresist composition is an essential material for the production of color filters included in display devices such as color filters, liquid crystal displays, organic electroluminescent devices, and display panels.
  • the color filter of the liquid crystal display device is used to prevent the mixing of R (red), G (green), B (blue), or in the touch panel device may be used for the bezel to cover the X, Y metal electrodes.
  • LTPS low temperature poly-silicon
  • oxide thin film transistors have been actively studied as devices for use in high-resolution driving over UD (Ultra Definition) and high-speed driving of 240 Hz or more.
  • the oxide thin film transistor changes the properties of the semiconductor by light
  • the above-described problem is minimized by introducing a light blocking layer.
  • the light shielding layer is mainly formed of a metal light shielding layer since a subsequent process such as PE-CVD is performed at a high temperature after the formation of the light shielding layer, the metal light shielding layer has high reflectivity and light is reflected between the source, the drain electrode, and the light shielding layer.
  • the parasitic voltage is generated between the source and drain electrodes to act as an element that resists the operation of the device and increases the load of the data line.
  • a light shielding layer may be introduced to eliminate a characteristic in which the contrast ratio is significantly lowered by reflection of upper and lower metal interconnections.
  • Patent Document 1 KR 2007-0131523 (2007.12.14)
  • Patent Document 2 [Patent Document 2] KR 2009-0131415 (2009.12.28)
  • Patent Document 3 JP 2011-247437 (2011.11.11)
  • the problem to be solved by the present invention is to provide a black matrix photoresist composition for a liquid crystal display panel which suppresses the effect of reducing the reflectance and inhibits the occurrence of color difference, and is advantageous in the processability of the pattern formation and the development process because the deep curing is advantageous.
  • the purpose is.
  • the present invention provides a black matrix photoresist composition using an oxime ester fluorene derivative compound represented by the following Chemical Formula 1 as a photopolymerization initiator.
  • R 1 to R 3 are each independently hydrogen, halogen, (C1-C20) alkyl, (C6-C20) aryl, (C1-C20) alkoxy, (C6-C20) aryl (C1-C20) alkyl, hydroxy ( C1-C20) alkyl, hydroxy (C1-C20) alkoxy (C1-C20) alkyl or (C3-C20) cycloalkyl;
  • A is hydrogen, (C1-C20) alkyl, (C6-C20) aryl, (C1-C20) alkoxy, (C6-C20) aryl (C1-C20) alkyl, hydroxy (C1-C20) alkyl, hydroxy ( C1-C20) alkoxy (C1-C20) alkyl, (C3-C20) cycloalkyl, amino, nitro, cyano or hydroxy;
  • n 0 or 1
  • 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 '(C1-C20) alkyl' group described in the present invention is preferably (C1-C10) alkyl, more preferably (C1-C6) alkyl.
  • the '(C6-C20) aryl' group is preferably (C6-C18) aryl.
  • the '(C1-C20) alkoxy' group is preferably (C1-C10) alkoxy, more preferably (C1-C4) alkoxy.
  • the '(C6-C20) aryl (C1-C20) alkyl' group is preferably (C6-C18) aryl (C1-C10) alkyl, more preferably (C6-C18) aryl (C1-C6) 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 (C1-C20) alkoxy (C1-C20) alkyl' group is preferably hydroxy (C1-C10) alkoxy (C1-C10) alkyl, more preferably hydroxy (C1-C4) alkoxy (C1) -C6) alkyl.
  • the '(C3-C20) cycloalkyl' group is preferably (C3-C10) 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- Pen
  • A is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, phenyl, naphthyl, biphenyl, terphenyl anthryl, indenyl, phenanthryl, methoxy, Ethoxy, propaneoxy, butoxy, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxymethoxymethyl, hydroxymethoxyethyl, hydroxymethoxypropyl, hydroxymethoxybutyl, hydroxy Hydroxyethoxymethyl, hydroxyethoxyethyl, hydroxyethoxypropyl, hydroxyethoxybutyl, amino, nitro, cyano or hydroxy, but is not limited thereto.
  • oxime ester fluorene derivative compound As the oxime ester fluorene derivative compound according to the present invention, the following compounds are representatively mentioned, but the following compounds are not intended to limit the present invention.
  • the oxime ester fluorene derivative compound represented by Chemical Formula 1 is included in the black matrix photoresist composition as a photopolymerization initiator.
  • the black matrix photoresist composition of the present invention includes an oxime ester fluorene derivative compound represented by Chemical Formula 1, a binder resin, a polymerizable compound having an ethylenically unsaturated bond, a colorant, and the like, and a reduction in reflectance and inhibition of color difference generation. It is excellent in thin film properties, such as the point which suppresses a phenomenon and advantageously deep-hardens, and is advantageous for pattern formation.
  • an acrylic resin, a cardo resin, a silicone resin, or a mixed resin thereof, which is an acrylic polymer or an acrylic polymer having an acrylic unsaturated bond in the side chain, may be used as the binder resin.
  • the binder resin may control its content in order to provide pattern properties, thin film properties such as heat resistance and chemical resistance. For example, 3 to 50 wt% may be used based on 100 wt% of the photoresist composition.
  • the binder resin preferably has a weight average molecular weight of 2,000 to 300,000, and a dispersion degree of 1.0 to 10.0, more preferably a weight average molecular weight of 4,000 to 100,000,00.
  • the acrylic polymer is a copolymer of monomers including the following monomers, and examples of such monomers include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate and pentyl ( Meth) acrylate, hexyl (meth) acrylate, cyclohexyl (meth) acrylate, heptyl (meth) acrylate, octyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, lauryl (Meth) acrylate, dodecyl (meth) acrylate, tetradecyl (meth) acrylate and hexadecyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, dicyclopentanyl (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, such as acrylic acid, methacrylic acid, itaconic acid, maleic acid and maleic acid monoalkyl ester.
  • 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, 3,4- Acrylic monomer and methyl (meth) acrylate containing epoxy groups, such as epoxy butyl (meth) acrylate, 2, 3- epoxycyclohexyl (meth) acrylate, and 3, 4- epoxycyclohexyl methyl (meth) acrylate, Alkyl (meth) acrylates, such as hexyl (meth) acrylate, cyclohexyl (meth) acrylate, isobonyl (meth) acrylate, adamantyl (meth) acrylate, dicyclopentanyl (meth) acrylate, and dish Clofenthenyl (meth) acrylate, benzyl (meth) acrylate, 2-meth
  • a cardo-based resin may be used as the binder resin, and the cardo-based resin refers to an acrylic binder resin including a fluorene group in a main chain, and is not particularly limited in structure.
  • siloxane resin may be used as the silicone resin, and more specifically, the siloxane resin disclosed in Korean Patent No. 10-1537771 may be used as the silicone resin, and a manufacturing method may also be prepared by the method described in the patent. Can be.
  • the siloxane resin may have an acid value in the range of 10 to 200 mgKOH / g resin when titrating KOH.
  • the siloxane resin usable in one embodiment of the present invention may be a siloxane resin including a polymerized unit represented by the following Chemical Formula 2 and a polymerized unit represented by the following Chemical Formula 3.
  • R 4 is a linear or branched alkylene group having 1 to 20 carbon atoms, an arylene group having 6 to 20 carbon atoms, an alkylene group having 7 to 20 carbon atoms substituted with an aryl group, and an arylene group having 7 to 20 carbon atoms substituted with an alkyl group. Or a group having 7 to 20 carbon atoms, in which an alkylene group and an arylene group are connected.
  • X is hydroxy, carboxylic acid, carboxylic anhydride, carboxylic anhydride derivative, imide, imide derivative, amide, amide derivative, amine or mercanto,
  • Each R 4 is independently hydrogen, a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 10 carbon atoms, an unsaturated hydrocarbon group having 2 to 10 carbon atoms, or an acyloxy group having 2 to 10 carbon atoms,
  • the siloxane resin may be composed of 5 to 40 mol% of the polymerized units of Formula 1 and 95 to 60 mol% of the polymerized units of Formula 2 based on 100 mol% of the polymerized units of Formula 1 and the polymerized units of Formula 2.
  • siloxane resin As a specific example of the siloxane resin, a siloxane resin including the first polymer unit represented by the following Chemical Formulas 4 to 17 and the second polymer unit listed below may be used, but is not limited thereto.
  • n and n may be each independently an integer of 1 to 20.
  • tetraalkoxy silane, trialkoxy silane, methyl trialkoxy silane, ethyl trialkoxy silane, n-propyl trialkoxy silane isopropyl trialkoxy silane, n-butyl trialkoxy silane , tert-butyl trialkoxy silane, phenyl trialkoxy silane, naphtha trialkoxy silane, vinyl trialkoxy silane, methacryloxymethyl trialkoxy silane, 2-methacryloxyethyl trialkoxy silane, 3-methacryloxypropyl trialkoxy silane , 3-methacryloxypropyl trialkoxy silane , 3-methacryloxypropyl methyl dialkoxy silane, 3-methacryloxypropyl ethyl dialkoxy silane, acryloxymethyl trialkoxy silane, 2-acryloxyethyl trialkoxy silane, 3-acryloxypropyl trialkoxy silane, 3- Acryloxypropyl methyl dialkoxy silane, 3-acryloxy
  • 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 1 to 200 parts by weight, preferably 10 to 150 parts by weight, more preferably 50 to 120 parts by weight, based on 100 parts by weight of the binder resin.
  • 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 dihydroxy ethyl (
  • the amount of the oxime ester fluorene derivative compound of Formula 1 included as a photopolymerization initiator in the black matrix photoresist composition of the present invention is a content for minimizing the reflectance of black matrix, suppressing color difference, and smoothing the deep curing It may be 0.01 to 50 parts by weight, preferably 0.02 to 25 parts by weight, 0.5 to 10 parts by weight based on 100 parts by weight of the polymerizable compound having an ethylenically unsaturated bond.
  • the degree of photocuring is ensured, thereby making it easier to form a pattern due to the developability difference between the exposed portion and the non-exposed portion, and preventing the formation of a T-shaped pattern due to excessive upper curing.
  • the desired pattern shape can be obtained.
  • a thioxanthone compound, acetophenone compound, biimidazole compound, triazine compound, thiol compound as an additional photopolymerization initiator in addition to the oxime ester fluorene derivative compound of Chemical Formula 1 It may further comprise one or two or more selected from the group consisting of O-acyl oxime compounds other than the compound represented by the formula (1).
  • thioxanthone type compound for example, thioxanthone, 2-chloro thioxanthone, 2-methyl thioxanthone, 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2, 4- dichloro Thioxanthone, 2, 4- dimethyl thioxanthone, 2, 4- diethyl thioxanthone, 2, 4- diisopropyl thioxanthone, etc.
  • 2-chloro thioxanthone 2-methyl thioxanthone
  • 2-isopropyl thioxanthone 4-isopropyl thioxanthone
  • 2, 4- dichloro Thioxanthone 2, 4- dimethyl thioxanthone, 2, 4- diethyl thioxanthone, 2, 4- diisopropyl thioxanthone, etc.
  • 2-methyl-1- [4- (methylthio) phenyl] -2- morpholino propane- 1-one, 2-benzyl-2- dimethylamino-1- ( 4-morpholinophenyl) butan-1-one, 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinophenyl) butan-1-one, and the like can be used.
  • biimidazole type compound 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'- tetraphenyl- 1,2'-biimidazole, 2,2, for example '-Bis (2,4-dichlororophenyl) -4,4', 5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis (2,4,6-trichloro Phenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole and the like.
  • triazine-based compound examples include 2,4,6-tris (trichloromethyl) -s-triazine, 2-methyl-4,6-bis (trichloromethyl) -s-triazine and 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
  • O-acyl oxime type compound 1,2-octanedione, 1- [4- (phenylthio) phenyl] -2- (O-benzoyl oxime), ethanone-1- [9-ethyl, for example] -6- (2-methylbenzoyl) -9H-carbazol-3-yl] -1- (O-acetyloxime), ethanone-1- [9-ethyl-6- (2-methyl-4-tetrahydro Furanylmethoxybenzoyl) -9H-carbazol-3-yl] -1- (O-acetyloxime), ethanone-1- [9-ethyl-6-X2-methyl-4- (2,2-dimethyl- 1,3-dioxoranyl) methoxybenzoyl r-9H-carbazol-3-yl] -1- (O-acetyloxime) and the like can be used.
  • the additional photopolymerization initiator other than the oxime ester fluorene derivative compound of formula 1 used as the photopolymerization initiator in the photoresist composition of the present invention is 0.01 to 20 parts by weight, preferably 100 parts by weight of the polymerizable compound having an ethylenically unsaturated bond. 0.05 to 10 parts by weight may be used.
  • the black matrix 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 silicone-based compound may improve adhesion between the ITO electrode and the photoresist composition and may increase heat resistance after curing.
  • the silicone compound having an epoxy group or an amine group include (3-glycidoxy propyl) trimethoxysilane, (3-glycidoxy propyl) triethoxysilane, and (3-glycidoxy propyl) methyldimethoxy silane.
  • Phosphorus (3-glycidoxypropyl) methyldiethoxysilane, (3-glycidoxypropyl) dimethylmethoxysilane, (3-glycidoxypropyl) dimethylethoxysilane, 3,4-epoxy butyl Trimethoxysilane, 3,4-epoxybutyltriethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrie Methoxysilane, aminopropyltrimethoxy silane, and the like, and these may be used alone or in combination of two or more thereof.
  • the content of the silicon compound having the epoxy group or the amine group may be 0.0001 to 20 parts by weight based on 100 parts by weight of the binder resin.
  • the black matrix 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 colorant of the present invention at least one selected from carbon black, titanium black, acekylene black, aniline black, perylene black, strontium titanate, chromium oxide, and ceria, which preferably exhibits light blocking properties, may be used.
  • the content of the colorant may be 1 to 300 parts by weight, preferably 3 to 200 parts by weight, more preferably 5 to 150 parts by weight based on 100 parts by weight of the binder resin.
  • the effect of light shielding may be improved, and in addition, process characteristics and electrical characteristics for pattern formation may be improved.
  • the black matrix photoresist composition according to the exemplary embodiment of the present invention may form a pattern through spin coating on a substrate by adding a solvent and then irradiating ultraviolet rays using a mask to develop the alkaline developer.
  • the content of the solvent may be 10 to 3,000 parts by weight, preferably 20 to 1,000 parts by weight, more preferably 30 to 500 parts by weight, based on 100 parts by weight of the binder resin.
  • the solvent may be ethyl acetate, butyl acetate, diethylene glycol dimethyl ether, diethylene glycol dimethyl ethyl ether, methyl methoxy propionate, ethyl ethoxy propion, in consideration of compatibility with binder resins, photopolymerization initiators and other compounds.
  • examples of the colorant included for application to the black matrix forming resist of the present invention include carbon black, titanium black, aniline black, and C.I. pigment black 7.
  • the black matrix photoresist composition is used as an photopolymerization initiator with an oxime ester fluorene derivative compound to suppress the effect of reducing the reflectance of the black matrix thin film and inhibiting the occurrence of color difference, and advantageously, deep curing is advantageous for the formation of a pattern.
  • an advantage that can be usefully used in the manufacture of a thin film.
  • the reaction temperature was raised to 85 ° C., and the reaction proceeded at the elevated temperature for 6 hours.
  • tetrahydrotrofuran and methanol were evaporated off in an appropriate amount, extracted with ether and water, and the organic phase was recovered. The remaining alcohol and solvent were evaporated to remove 54g of siloxane resin.
  • the obtained siloxane resin is dissolved in 125.5 g of propylene glycol monomethyl ether acetate.
  • the weight average molecular weight of the obtained siloxane resin was 6,000.
  • Cardo-based binder resin used CAP-01 (manufacturer: Miwon).
  • the content of Compound 1 was added 1.0, 2.0, 3.0% by weight, and the carbon black was not added to check the solubility, and the other components and the stirring method were prepared in the same photoresist composition as in Example 2.
  • Black matrix photoresist compositions of Comparative Examples 1 to 3 were prepared in the same manner as in Example 2, except that the following Compounds 5, 6, and 7 were used as photopolymerization initiators, respectively.
  • the photoresist composition was prepared in the same manner as in Example 2, with other components and stirring methods using 1.0 wt%, 2.0 wt%, and 3.0 wt% of the compound 6 as the photopolymerization initiator and no carbon black added for solubility. Was prepared.
  • the photoresist was spin-coated on the glass substrate to form a coating film having a thickness of about 1.9 ⁇ m after the heat treatment at 100 ° C. for 90 seconds.
  • the exposure gap was 150 ⁇ m using a photomask to measure CD (critical demension) of a pattern formed by increasing the pressure from 20 mJ / cm 2 to 10 mJ / cm 2 with a high pressure mercury lamp. After exposure it was developed in 0.04% KOH aqueous solution. Thereafter, the mixture was washed with pure water, dried, and post-baked in a convection oven at 230 ° C. for 30 minutes to form a black matrix pattern.
  • the sensitivity was expressed by the sensitivity of each sample as the exposure amount at which the size of the CD (Critical demension) of the pattern was saturated.
  • the number of pinholes generated on the surface of the black matrix was determined to be less than 0 to 3, less than 3 to 7 in 10 mm X 10 mm, and more than 7 to be X.
  • the reflectance of the black matrix formed through a process such as prebake, exposure, and postbake was measured.
  • Example Sensitivity Surface Hardness Developing Process Range (sec) reflectivity(%) Solubility One 60 ⁇ 80 6.5 - 2 80 ⁇ 60 6.7 - 3 90 ⁇ 40 6.5 - 4 120 ⁇ 30 6.7 - 5 40 ⁇ 110 6.4 - 6 60 ⁇ 70 6.4 - 7 60 ⁇ 70 6.5 - 8 80 ⁇ 50 6.3 - 9 40 ⁇ 110 6.4 - 10 60 ⁇ 70 6.3 - 11 60 ⁇ 70 6.4 - 12 80 ⁇ 50 6.5 - 13 60 ⁇ 100 5.8 - 14 80 ⁇ 80 5.9 - 15 90 ⁇ 80 6.1 - 16 120 ⁇ 60 6.0 - 17 60 ⁇ 100 5.9 - 18 ⁇ 40 ⁇ 100 - ⁇ 19 ⁇ 40 ⁇ 120 - ⁇ 20 ⁇ 40 ⁇ 120 - ⁇ Comparative Example 1 150 X 10 7.4 - Comparative Example 2 70 ⁇ 70 7.8 - Comparative Example 3 80 ⁇ 70 7.2 - Comparative Example 4 ⁇ 40 ⁇ 80

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  • Materials For Photolithography (AREA)

Abstract

La présente invention concerne une composition de résine photosensible pour matrice à fond noir pour un panneau d'affichage à cristaux liquides, la composition n'ayant aucune influence sur le facteur de transmission du panneau d'affichage à cristaux liquides en raison de l'utilisation d'un excellent initiateur de photo-polymérisation, supprimant la réduction du facteur de réflexion d'un film mince pour matrice à fond noir et l'inhibition de la génération d'une différence de couleurs, et étant avantageuse lors de la formation de motifs grâce à un durcissement de section profonde favorable. Plus précisément, un composé ester d'oxime dérivé du fluorène utilisé en tant qu'initiateur de photo-polymérisation dans la présente invention est représenté par la formule chimique 1 décrite dans l'invention.
PCT/KR2015/012191 2014-11-12 2015-11-12 Composition de résine photosensible pour matrice à fond noir pour un panneau d'affichage à cristaux liquides WO2016076652A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
CN201580073141.9A CN107111232A (zh) 2014-11-12 2015-11-12 用于液晶显示面板的黑色矩阵光致抗蚀剂组合物
JP2017525535A JP2017537347A (ja) 2014-11-12 2015-11-12 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

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KR10-2014-0157328 2014-11-12
KR20140157328 2014-11-12
KR1020150158807A KR101808818B1 (ko) 2014-11-12 2015-11-12 액정디스플레이 패널용 블랙매트릭스 포토레지스트 조성물
KR10-2015-0158807 2015-11-12

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WO2016076652A1 true WO2016076652A1 (fr) 2016-05-19

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KR20180002364A (ko) * 2016-06-29 2018-01-08 엘지디스플레이 주식회사 유기발광 표시장치용 포토레지스트 조성물 및 이를 이용한 유기발광 표시장치의 제조방법
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KR102458810B1 (ko) 2016-09-28 2022-10-26 메르크 파텐트 게엠베하 중합가능 액정 물질 및 중합된 액정 필름
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CN108073037A (zh) * 2016-11-18 2018-05-25 罗门哈斯电子材料韩国有限公司 著色感光性树脂组合物及由其制备的遮光间隔区
CN108073037B (zh) * 2016-11-18 2023-09-05 罗门哈斯电子材料韩国有限公司 著色感光性树脂组合物及由其制备的遮光间隔区
CN108153113B (zh) * 2016-12-02 2022-01-18 三星Sdi株式会社 感光性树脂组合物、使用其的黑色像素界定层以及显示装置
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CN108153113A (zh) * 2016-12-02 2018-06-12 三星Sdi株式会社 感光性树脂组合物、使用其的黑色像素界定层以及显示装置
CN108375876A (zh) * 2017-02-01 2018-08-07 东友精细化工有限公司 着色感光性树脂组合物、滤色器和图像显示装置
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WO2019034590A1 (fr) 2017-08-15 2019-02-21 Merck Patent Gmbh Matériau cristallin liquide polymérisable et film cristallin liquide polymérisé
WO2019064979A1 (fr) * 2017-09-27 2019-04-04 富士フイルム株式会社 Encre pour jet d'encre de type à durcissement par rayon actinique, et film de blocage de lumière ainsi que procédé de fabrication de celui-ci
JPWO2019064979A1 (ja) * 2017-09-27 2020-11-05 富士フイルム株式会社 活性エネルギー線硬化型インクジェットインク、遮光膜、及び遮光膜の製造方法
US11299643B2 (en) 2017-09-27 2022-04-12 Fujifilm Corporation Active energy ray curable-type ink jet ink, light shielding film, and method of manufacturing light shielding film
WO2019207081A1 (fr) 2018-04-27 2019-10-31 Merck Patent Gmbh Matériau de cristaux liquides polymérisables et film de cristaux liquides polymérisés
CN110471255A (zh) * 2018-05-10 2019-11-19 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
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
KR102381639B1 (ko) 2018-11-16 2022-04-01 주식회사 엘지화학 감광성 수지 조성물, 감광재, 디스플레이 장치 및 감광성 수지 조성물의 저온 경화 방법
KR20200057861A (ko) * 2018-11-16 2020-05-27 주식회사 엘지화학 감광성 수지 조성물, 감광재, 디스플레이 장치 및 감광성 수지 조성물의 저온 경화 방법

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