CN114127637A - Photosensitive resin composition - Google Patents
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- CN114127637A CN114127637A CN202080050829.6A CN202080050829A CN114127637A CN 114127637 A CN114127637 A CN 114127637A CN 202080050829 A CN202080050829 A CN 202080050829A CN 114127637 A CN114127637 A CN 114127637A
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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
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133512—Light shielding layers, e.g. black matrix
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1339—Gaskets; Spacers; Sealing of cells
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- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1339—Gaskets; Spacers; Sealing of cells
- G02F1/13398—Spacer materials; Spacer properties
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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
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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
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
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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
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
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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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01J—ELECTRIC DISCHARGE TUBES OR DISCHARGE LAMPS
- H01J1/00—Details of electrodes, of magnetic control means, of screens, or of the mounting or spacing thereof, common to two or more basic types of discharge tubes or lamps
- H01J1/02—Main electrodes
- H01J1/36—Solid anodes; Solid auxiliary anodes for maintaining a discharge
- H01J1/44—Rotary anodes; Arrangements for rotating anodes; Cooling rotary anodes
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- Optics & Photonics (AREA)
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Abstract
The present invention relates to a photosensitive resin composition, and more particularly, to a photosensitive resin composition which realizes a fine pattern while having a high residual film ratio, and thus is suitable for forming a columnar spacer, a black matrix, or a colored (e.g., black) columnar spacer, and thus can be used for various electronic elements including OLED displays and TFT-LCD panels.
Description
Technical Field
The present invention relates to a photosensitive resin composition, and more particularly, to a photosensitive resin composition which realizes a fine pattern while having a high residual film ratio, and thus is suitable for forming a columnar spacer, a black matrix, or a colored (e.g., black) columnar spacer, and thus can be used for various electronic elements including OLED displays and TFT-LCD panels.
Background
In recent years, the display industry is roughly classified into TV displays, small and medium-sized displays for notebook computers and computer displays, and the market of mobile displays of 10 inches or less. Since the display market requires high definition products every year, there is a problem in that the integration of the TFT-LCD should be improved, and since the price of the LCD is reduced, the production cost is also required to be reduced.
The black matrix, the columnar spacer, etc. in the liquid crystal display element play a role of maintaining the gap between the upper plate and the lower plate, and in order to form such a fine pattern, the photosensitive composition should have improved film residue ratio, sensitivity, development contrast, definition, solubility of the polymer resin, adhesion to the substrate, and circuit line width uniformity (CD uniformity).
An exemplary structure of the columnar spacer pattern is shown in fig. 1. In such a columnar spacer pattern, if the residual film ratio can be increased at the same Bottom critical dimension (Bottom CD), the consumption of the resist material during the manufacturing process can be reduced, and thus the product price can be reduced.
The existing photosensitive resin composition realizes a fine pattern by using a photopolymerization initiator of a specific structure or realizes a fine pattern by other additives such as a radical scavenger (for example: korean patent laid-open No. 10-1435652). However, the radical functional group generated by exposure from the conventional photopolymerization initiator uses a method of reducing the initiator content for the purpose of forming a fine pattern, but has a disadvantage of reducing the residual film ratio.
Disclosure of Invention
Technical problem to be solved
The present invention has been made to solve the above problems of the prior art, and an object of the present invention is to provide a photosensitive resin composition which can realize a fine pattern and can improve a residual film ratio.
Technical scheme
In order to solve the above-mentioned technical problems, the present invention provides a photosensitive resin composition comprising: (a) an alkali-soluble binder resin; (b) an optional photopolymerizable compound; (c) a photopolymerization initiator having a structure represented by the following chemical formula 1; and (d) an organic solvent, the photosensitive resin composition comprising 0.7 to 20 parts by weight of the (c) photopolymerization initiator, based on 100 parts by weight of the sum of the (a) alkali-soluble binder resin and (b) any photopolymerizable compound.
[ chemical formula 1]
In the chemical formula 1, R1、R2And R4-R10Each independently represents hydrogen, halogen, a linear or branched alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aralkyl group having 7 to 40 carbon atoms, a hydroxyalkyl group having 1 to 20 carbon atoms, a hydroxyalkoxyalkyl group having 2 to 40 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms, R3Represents an aryl group having 6 to 20 carbon atoms.
In one embodiment, the photosensitive resin composition of the present invention may further comprise a chain transfer agent for adjusting the molecular weight.
According to another aspect of the present invention, there is provided a finely patterned cured product formed from the photosensitive resin composition of the present invention.
Advantageous effects
The photosensitive resin composition of the present invention can realize a fine pattern and can increase a residual film ratio, and thus is suitable for forming a columnar spacer, a black matrix, or a colored (e.g., black) columnar spacer, and thus can be used for various electronic components including OLED displays and TFT-LCD panels.
Drawings
Fig. 1 is an exemplary structure of a columnar spacer pattern.
Fig. 2 is a graph showing the residual film ratio of the kinds of photopolymerization initiators used in the examples according to the present invention and the comparative examples.
FIG. 3 is a graph showing a comparison of the absorbance according to the wavelength of absorbed light of the photoinitiator C used in the example of the present invention and the photoinitiator OXE-01 used in comparative example 7.
Detailed Description
The present invention will be described in more detail below.
The photosensitive resin composition of the present invention comprises (a) an alkali-soluble binder resin.
In one embodiment, as the alkali-soluble binder resin, an acrylic polymer or an acrylic polymer having an acrylic unsaturated bond in a side chain may be used.
The acrylic polymer is a polymer (including a homopolymer or a copolymer) of an acrylic-based monomer, and examples of such a monomer include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, 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, hexadecyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, dicyclopentenyl (meth) acrylate, benzyl (meth) acrylate, cyclohexyl (meth) acrylate, cyclopentyl (meth) acrylate, dicyclopentenyl (meth) acrylate, and the like, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, itaconic (meth) acrylate, maleic acid, maleic anhydride, monoalkyl maleate, monoalkyl itaconate, monoalkyl fumarate, glycidyl (meth) acrylate, 3, 4-epoxybutyl (meth) acrylate, 2, 3-epoxycyclohexyl (meth) acrylate, 3, 4-epoxycyclohexylmethyl (meth) acrylate, 3-methyloxetane-3-methyl (meth) acrylate, 3-ethyloxetane-3-methyl (meth) acrylate, styrene, α -methylstyrene, acetoxystyrene, N-methylmaleimide, N-ethylmaleimide, maleic anhydride, itaconic anhydride, 2-3-methyl-3-methyl-3-methyl (meth) acrylate, styrene, N-methyl-maleimide, and N-methyl maleimide, N-propylmaleimide, N-butylmaleimide, N-cyclohexylmaleimide, (meth) acrylamide, N-methyl (meth) acrylamide, or the like, and they may be used each alone or in combination of two or more.
As the acrylic polymer having an acrylic unsaturated bond in a side chain, a copolymer obtained by addition reaction of an acrylic polymer containing a carboxylic acid and an epoxy resin can be used. According to one embodiment, a binder resin obtained by addition reaction of an acrylic copolymer containing a carboxylic acid, which is obtained by reacting an acrylic monomer containing a carboxylic acid such as (meth) acrylic acid, itaconic acid, maleic acid, or monoalkyl maleate with two or more alkyl (meth) acrylates such as methyl (meth) acrylate, hexyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, and the like, and an epoxy compound such as glycidyl (meth) acrylate, 3, 4-epoxybutyl (meth) acrylate, 2, 3-epoxycyclohexyl (meth) acrylate, or 3, 4-epoxycyclohexylmethyl (meth) acrylate, at a temperature of 40 to 180 ℃ can be used, Dicyclopentyl (meth) acrylate, dicyclopentenyl (meth) acrylate, benzyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, styrene, α -methylstyrene, acetoxystyrene, N-methylmaleimide, N-ethylmaleimide, N-propylmaleimide, N-butylmaleimide, N-cyclohexylmaleimide, (meth) acrylamide, N-methyl (meth) acrylamide, and the like.
As another example of the acrylic polymer having an acrylic unsaturated bond in a side chain, a copolymer obtained by addition reaction of an epoxy group-containing acrylic copolymer and a carboxylic acid-containing compound can be cited. According to one embodiment, for example, a binder resin obtained by addition reaction of an epoxy group-containing acrylic copolymer obtained by reacting an epoxy group-containing acrylic monomer such as glycidyl (meth) acrylate, 3, 4-epoxybutyl (meth) acrylate, 2, 3-epoxycyclohexyl (meth) acrylate or 3, 4-epoxycyclohexylmethyl (meth) acrylate with two or more alkyl (meth) acrylates such as glycidyl (meth) acrylate or hexyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, mono (meth) acrylate, or mono (meth) acrylate at a temperature of 40 to 180 ℃ may be used, Adamantyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, benzyl (meth) acrylate, 2-methoxyethyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, styrene, α -methylstyrene, acetoxystyrene, N-methylmaleimide, N-ethylmaleimide, N-propylmaleimide, N-butylmaleimide, N-cyclohexylmaleimide, (meth) acrylamide, N-methyl (meth) acrylamide, and the like.
According to one embodiment of the present invention, the alkali-soluble binder resin may have a weight average molecular weight of 1000 or more, 2000 or more, 3000 or more, or 4000 or more, and may be 300000 or less, 200000 or less, 100000 or less, 50000 or less, or 40000 or less, but is not limited thereto.
According to one embodiment of the present invention, the alkali-soluble binder resin may have a dispersity of 1.0 or more, 1.2 or more, or 1.5 or more, and may be 10.0 or less, 5.0 or less, or 3.0 or less, but is not limited thereto.
According to a specific embodiment of the present invention, in addition to the alkali soluble binder resin, an acrylate group-containing binder resin or a novolac (Novolak) or bisphenol type alkali soluble polymer may be further used. As the binder resin which can be further used in the products sold, there are, but not limited to, PCR-122H, PCR-1173H, PCR-1221H, PCR-1220H, CCR-1171H, CCR-1307H, CCR-1309H, ZAR-1494H, ZAR-2001H, ZFR-1491H, ZFR-1554H available from Nippon Kayaku, Inc.
The alkali-soluble binder resin may be a random copolymer which is not limited by the arrangement order of the respective polymerization units, but is not limited thereto.
The content of the alkali-soluble binder resin in the photosensitive resin composition of the present invention may be appropriately adjusted as needed, and for example, may be 3 parts by weight or more, 5 parts by weight or more, 7 parts by weight or more, 9 parts by weight or more, or 10 parts by weight or more, and may be 99 parts by weight or less, 90 parts by weight or less, 80 parts by weight or less, 70 parts by weight or less, 60 parts by weight or less, 50 parts by weight or less, 45 parts by weight or less, 40 parts by weight or less, 35 parts by weight or less, or 30 parts by weight or less, with respect to 100 parts by weight of the total composition, but is not limited thereto.
The photosensitive resin composition of the present invention may contain (b) a photopolymerizable compound as an optional component.
The photopolymerizable compound may be a crosslinking type monomer having at least 2 or more vinyl double bonds.
In one embodiment, as the photopolymerizable compound, for example, polyethylene glycol di (meth) acrylate, ethylene glycol di (meth) acrylate, polypropylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, trimethylolpropane di (meth) acrylate, an addition reaction product of bisphenol a and diglycidyl ether acrylic acid, ethyl isocyanuric acid tri (meth) acrylate, a phthalic diester of β -hydroxyethyl (meth) acrylate, an addition reaction product of β -hydroxyethyl (meth) acrylate and toluene diisocyanate, trimethylolpropane tri (meth) acrylate, tetramethylolmethane tetra (meth) acrylate, pentaerythritol tri (meth) acrylate, and the like, which are prepared by reacting a mixture of ethylene oxide and propylene oxide with a number of ethylene oxide groups of 2 to 20, and propylene glycol di (meth) acrylate, trimethylolpropane di (meth) acrylate, and propylene oxide groups of 2 to 14, and the like, Pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol tri (meth) acrylate, an addition reaction product of trimethylol and propane triglycidyl ether acrylic acid, an epoxy novolac acrylate resin formed by reacting an addition reaction product of an epoxy novolac resin and (meth) acrylic acid with phthalic anhydride, or a combination thereof, but is not limited thereto.
In another embodiment, an isocyanurate compound may be used as the photopolymerizable compound. Examples of the isocyanurate compound that can be used as the photopolymerizable compound include monoallyl diglycidyl isocyanurate compound, diallyl monoglycidyl isocyanurate compound, and triallyl isocyanurate compound.
Specifically, examples of the monoallyl diglycidyl isocyanurate compound include monoallyl diglycidyl isocyanurate, 1-allyl-3, 5-bis (2-methylepoxypropyl) isocyanurate, 1- (2-methylpropenyl) -3, 5-diglycidyl isocyanurate, and 1- (2-methylpropenyl) -3, 5-bis (2-methylepoxypropyl) isocyanurate, and examples of the diallyl monoglycidyl isocyanurate compound include diallyl monoglycidyl isocyanurate, 1, 3-diallyl-5- (2-methylepoxypropyl) isocyanurate, 1, 3-bis (2-methylpropenyl) -5-glycidyl isocyanurate, 1, 3-bis (2-methylpropenyl) -5- (2-methylepoxypropyl) isocyanurate, and the like, and examples of the triallyl isocyanurate compound include triallyl isocyanurate, tris (2-methylpropenyl) isocyanurate, and any one or two or more selected from them can be used in combination, but not limited thereto.
When the photopolymerizable compound is contained in the photosensitive resin composition of the present invention, the content thereof may be appropriately adjusted as needed, and for example, may be 2 parts by weight or more, 4 parts by weight or more, 6 parts by weight or more, 8 parts by weight or more, or 10 parts by weight or more, and may be 70 parts by weight or less, 65 parts by weight or less, 60 parts by weight or less, 55 parts by weight or less, or 50 parts by weight or less, based on 100 parts by weight of the total composition, but is not limited thereto.
The photosensitive resin composition of the present invention includes (c) a photopolymerization initiator having a structure represented by the following chemical formula 1.
[ chemical formula 1]
In the chemical formula 1, R1、R2And R4-R10Each independently represents hydrogen, halogen, a linear or branched alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aralkyl group having 7 to 40 carbon atoms, a hydroxyalkyl group having 1 to 20 carbon atoms, a hydroxyalkoxyalkyl group having 2 to 40 carbon atoms or a cycloalkyl group having 3 to 20 carbon atoms; r3Represents an aryl group having 6 to 20 carbon atoms.
More specifically, in the chemical formula 1, R1、R2And R4-R10Each independently represents hydrogen, halogen, a linear or branched alkyl group having 1 to 16 carbon atoms, an aryl group having 6 to 14 carbon atoms, an alkoxy group having 1 to 16 carbon atoms, an aralkyl group having 7 to 30 carbon atoms, a hydroxyalkyl group having 1 to 16 carbon atoms, a hydroxyalkoxyalkyl group having 2 to 32 carbon atoms or a cycloalkyl group having 3 to 16 carbon atoms, R3Represents an aryl group having 6 to 14 carbon atoms.
Further specifically, in the chemical formula 1, R1、R2And R4-R10Each independently represents hydrogen, halogen, a linear or branched alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, a hydroxyalkyl group having 1 to 10 carbon atoms, a hydroxyalkoxyalkyl group having 2 to 20 carbon atoms or a cycloalkyl group having 3 to 10 carbon atoms, R3Represents an aryl group having 6 to 10 carbon atoms.
Further specifically, in the chemical formula 1, R1、R2And R4-R10Each independently represents hydrogen, halogen, a linear or branched alkyl group having 1 to 6 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an aralkyl group having 7 to 16 carbon atoms, a hydroxyalkyl group having 1 to 6 carbon atoms, a hydroxyalkoxyalkyl group having 2 to 12 carbon atoms or a cycloalkyl group having 3 to 6 carbon atoms, R3Represents an aryl group having 6 to 10 carbon atoms.
In the chemical formula 1, the linear or branched alkyl group, the aryl group, the alkoxy group, the aralkyl group, the hydroxyalkyl group, the hydroxyalkoxyalkyl group, and the cycloalkyl group may each independently be unsubstituted, or may be substituted with halogen, a linear or branched alkyl group having 1 to 6 carbon atoms, or a cycloalkyl group having 3 to 6 carbon atoms.
According to a specific embodiment of the present invention, in the chemical formula 1, R1May each independently be hydrogen, methyl, ethyl, propyl or butyl; r2Can be methyl or ethylAlkyl, propyl or butyl; r3May be phenyl; r4-R10May be hydrogen.
The photopolymerization initiator having the structure represented by the chemical formula 1 imparts excellent residual film rate characteristics to the photosensitive resin composition of the present invention, particularly, with respect to R3Conventional photopolymerization initiators having an alkyl group (e.g., methyl group, ethyl group, etc.) at a position provide significantly superior residual film rate characteristics at the same fine pattern size.
In the photosensitive resin composition of the present invention, the (c) photopolymerization initiator of chemical formula 1 is contained in an amount of 0.7 to 20 parts by weight, based on 100 parts by weight of the total of the (a) alkali-soluble binder resin and (b) photopolymerizable compound of any component. When the content of the (c) photopolymerization initiator of chemical formula 1 contained in the photosensitive resin composition of the present invention is less than 0.7 parts by weight based on 100 parts by weight of the total of (a) the alkali-soluble binder resin and (b) the photopolymerizable compound of any component, the residual film ratio may be deteriorated due to low sensitivity and there is difficulty in pattern formation, and when the content of the (c) photopolymerization initiator of chemical formula 1 exceeds 20 parts by weight, a problem may occur in storage stability and foreign substances may be generated on the surface of a film due to the decrease in solubility of the photopolymerization initiator.
In one embodiment, the photopolymerization initiator of formula 1 contained in the photosensitive resin composition of the present invention may be contained in an amount of 0.8 parts by weight or more, 0.9 parts by weight or more, 1.0 parts by weight or more, 1.1 parts by weight or more, 1.2 parts by weight or more, 1.4 parts by weight or more, 1.6 parts by weight or more, or 1.8 parts by weight or more, based on 100 parts by weight of the total of (a) the alkali-soluble binder resin and (b) the photopolymerizable compound, and may be 19.5 parts by weight or less, 19 parts by weight or less, 18.5 parts by weight or less, 18 parts by weight or less, 16 parts by weight or less, 14 parts by weight or less, 12 parts by weight or less, 10 parts by weight or less, or 8 parts by weight or less.
The photosensitive resin composition of the present invention may further include an additional photopolymerization initiator, if necessary, in addition to the photopolymerization initiator of chemical formula 1. Examples of the photopolymerization initiator which can be further used in the present invention include commonly used photoinitiator compounds such as triazines, benzoins, acetophenones, imidazoles, xanthenone and oxime esters, more specifically triphenylphosphinyl, phenylbiphenone, 1-hydroxy-1-benzoylcyclohexane, benzyldimethyl ketal, 1-benzyl-1-dimethylamino-1- (4-morpholino-benzoyl) propane, 2-morpholino-2- (4-methylthio) benzoylpropane, thioxanthone (thioxanthone), 1-chloro-4-propylthioxanthone, isopropylthioxanthone, diethylthioxanthone, ethylanthraquinone, 4-benzoyl-4-methylbenzophenone, benzoin butyl ether, thioethers and the like, 2-hydroxy-2-benzoylpropane, 2-hydroxy-2- (4-isopropyl) benzoylpropane, 4-butylbenzoyltrichloromethane (4-butylbenzoyltrichloromethane), 4-phenoxybenzoyl dichloromethane, methyl benzoylformate, 1, 7-bis (9-acridinyl) heptane, 9-n-butyl-3, 6-bis (2-morpholino-isobutyryl) carbazole, 2-methyl-4, 6-bis (trichloromethyl) -s-triazine, 2-phenyl-4, 6-bis (trichloromethyl) -s-triazine, 2-naphthyl-4, 6-bis (trichloromethyl) -s-triazine, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -1-butanone, 2-methyl-1- [ (4-methylthio) phenyl ] -2-morpholinopropan-1-one, 2 ' -bis (2, 4-dichlorophenyl) -4,4 ', 5,5 ' -tetraphenyl-1, 2 ' -biimidazole, 4 ' -bis (diethylamino) benzophenone, 2-mercaptobenzothiazole, Irgacure 369, Irgacure 379, Irgacure 651, Irgacure 907, Darocur TPO, Irgacure 819, OXE-01, OXE-02, N-1919, NCI-831, SPI-02, SPI-03, SPI-04, SPI-05 and the like of Ciba Specialty Chemicals, but are not limited thereto. When the photosensitive resin composition of the present invention contains such an additional photopolymerization initiator, the content thereof may be appropriately adjusted as necessary within a range in which the object of the present invention can be achieved.
The photosensitive resin composition of the present invention comprises (d) an organic solvent.
Examples of the organic solvent include: alcohols such as methanol and ethanol; ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, anisole and tetrahydrofuran; glycol ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; cellosolve acetates such as methyl cellosolve acetate, ethyl cellosolve acetate, and diethyl cellosolve acetate; carbitols such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, and diethylene glycol diethyl ether; propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate; aromatic hydrocarbons such as toluene and xylene; ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl-n-amyl ketone, and 2-heptanone; saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate and isobutyl acetate; lactic acid esters such as methyl lactate and ethyl lactate; alkyl oxyacetates such as methyl oxyacetate, ethyl oxyacetate and butyl oxyacetate; alkyl alkoxyacetates such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate and ethyl ethoxyacetate; alkyl esters of 3-oxopropionic acid such as methyl 3-oxopropionate and ethyl 3-oxopropionate; alkyl esters of 3-alkoxypropionic acid such as methyl 3-methoxypropionate, ethyl 3-ethoxypropionate and methyl 3-ethoxypropionate; alkyl esters of 2-oxopropionic acid such as methyl 2-oxopropionate, ethyl 2-oxopropionate and propyl 2-oxopropionate; alkyl esters of 2-alkoxypropionic acid such as methyl 2-methoxypropionate, ethyl 2-ethoxypropionate and methyl 2-ethoxypropionate; alkyl esters of monooxymonocarboxylic acids such as 2-oxo-2-methylpropanoic acid esters such as methyl 2-oxo-2-methylpropionate and ethyl 2-oxo-2-methylpropionate, and alkyl 2-alkoxy-2-methylpropionates such as methyl 2-methoxy-2-methylpropionate and ethyl 2-ethoxy-2-methylpropionate; esters such as ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl glycolate, and methyl 2-hydroxy-3-methylbutyrate; ketonic acid esters such as ethyl pyruvate and the like, and N-methylformamide, N-dimethylformamide, N-methylformanilide, N-methylacetamide, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, benzylethyl ether, dihexyl ether, acetylacetone, isophorone, hexanoic acid, octanoic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, γ -butyrolactone, ethylene carbonate, propylene carbonate, phenylcellosolve acetate and the like are exemplified. The organic solvents selected from the above may be used alone or in combination of two or more.
The content of the organic solvent in the photosensitive resin composition of the present invention may be appropriately adjusted as needed, and for example, may be 30 parts by weight or more, 35 parts by weight or more, 40 parts by weight or more, 45 parts by weight or more, or 50 parts by weight or more, and may be 90 parts by weight or less, 85 parts by weight or less, 80 parts by weight or less, 75 parts by weight or less, or 70 parts by weight or less, based on 100 parts by weight of the total composition, but is not limited thereto. The solid concentration of the photosensitive resin composition of the present invention is not particularly limited, and in one embodiment, the solid concentration may be 10 to 50% by weight, but is not limited thereto.
In one embodiment, the photosensitive resin composition of the present invention may further comprise a chain transfer agent for adjusting the molecular weight.
In one embodiment, as the chain transfer agent for adjusting the molecular weight, a compound containing a sulfur atom may be used. The chain transfer agent containing a sulfur atom may be selected from, for example, thioglycolic acid, thiomalic acid, thiosalicylic acid, 2-mercaptopropionic acid, 3-mercaptobutyric acid, N- (2-mercaptopropionyl) glycine, 2-mercaptonicotinic acid, 3- [ N- (2-mercaptoethyl) carbamoyl ] propionic acid, 3- [ N- (2-mercaptoethyl) amino ] propionic acid, N- (3-mercaptopropionyl) alanine, 2-mercaptoethanesulfonic acid, 3-mercaptopropanesulfonic acid, 4-mercaptobutanesulfonic acid, dodecyl (4-methylthio) phenyl ether, 2-mercaptoethanol, 3-mercapto-1, 2-propanediol, 1-mercapto-2-propanol, 3-mercapto-2-butanol, thiosalicylic acid, 3-mercaptopropionic acid, 2-mercaptopropionic acid, and mixtures thereof, Thiols such as mercaptophenol, 2-mercaptoethylamine, 2-mercaptoimidazole, 2-mercaptobenzimidazole, 2-mercapto-3-pyridinol, 2-mercaptobenzothiazole, thioglycolic acid, trimethylolpropane tris (3-mercaptopropionic acid) ester, pentaerythritol tetrakis (3-mercaptopropionic acid acetic acid, dodecylmercaptan, 2, 4-diphenyl-4-methyl-1-pentene, octylmercaptan, and 2-mercaptoethanol, or combinations thereof, but the present invention is not limited thereto.
When the chain transfer agent is contained in the photosensitive resin composition of the present invention, the content thereof may be appropriately adjusted as needed, and for example, it may be contained in an amount of 0.1 to 10 parts by weight, more specifically 0.2 to 5 parts by weight, and still more specifically 0.5 to 2 parts by weight, based on 100 parts by weight of the total composition, but is not limited thereto.
In addition, in one embodiment, the photosensitive resin composition of the present invention may optionally further contain additives known in the art, such as fillers, other high molecular compounds, thermal radical initiators, ultraviolet absorbers, tackifiers, polymerization regulators, pH regulators, scale inhibitors, electrolytes, and the like, as needed. The kind and content of these additional additives are not particularly limited, and the usual kinds and contents known in the art may be used.
The photosensitive composition of the present invention may contain, in addition to the above-mentioned components, one or more additional components, for example, a colorant, an auxiliary curing agent, an adhesion promoter and/or a surfactant, as necessary.
The colorant may comprise an organic pigment, a dye, or a combination thereof. The organic pigment may be one or a mixture of two or more selected from red pigments, green pigments, blue pigments and yellow pigments. In addition, the black colorant may include a black inorganic colorant, a black organic colorant, or a mixture thereof.
The red pigment may be c.i. red pigment 179, c.i. red pigment 254, c.i. red pigment 255, c.i. red pigment 264, c.i. red pigment 270, c.i. red pigment 272, c.i. red pigment 177, c.i. red pigment 89, etc. in the Color Index (Color Index), and they may be used alone or in combination of two or more, but are not necessarily limited thereto.
The green pigment may be a halogen-substituted copper phthalocyanine pigment such as c.i. green pigment 59, c.i. green pigment 58, c.i. green pigment 36, c.i. green pigment 7, etc. in the color index, and they may be used alone or in a mixture of two or more, but are not necessarily limited thereto.
The blue pigment may be c.i. blue pigment 15:6, c.i. blue pigment 15:0, c.i. blue pigment 15:1, c.i. blue pigment 15:2, c.i. blue pigment 15:3, c.i. blue pigment 15:4, c.i. blue pigment 15:5, c.i. blue pigment 15:6, c.i. blue pigment 16, etc. in the color index, and they may be used alone or in a mixture of two or more, but are not necessarily limited thereto.
The yellow pigment may be an isoindoline-based pigment such as c.i. yellow pigment 139, a quinoline yellow-based pigment such as c.i. yellow pigment 138, a nickel complex pigment such as c.i. yellow pigment 150, c.i. yellow pigment 100, or the like in color index, and may be used alone or in a mixture of two or more thereof, but is not necessarily limited thereto.
As specific examples of the black inorganic colorant, metal oxides such as carbon black, titanium black, Cu-Fe-Mn-based oxides, and synthetic iron black, which may be used alone or in a mixture of two or more, and the like may be used, but are not necessarily limited thereto.
Specific examples of the Black organic colorant include aniline Black, lactam Black, perylene Black, and the like, and among them, lactam Black (e.g., Black 582 from basf corporation) can be used, and these can be used alone or in a mixture of two or more kinds, but the Black organic colorant is not necessarily limited thereto.
When a pigment is used as the colorant, the pigment may be added to the colored photosensitive resin composition in the form of a colored dispersion (mill base) mixed with a dispersant, a copolymer resin, a solvent, or the like, in order to disperse the pigment.
When the colorant is contained in the photosensitive resin composition of the present invention, the content thereof may be appropriately adjusted as needed, and for example, it may be contained in an amount of 1 to 40 parts by weight, more specifically 2 to 20 parts by weight, and still more specifically 5 to 10 parts by weight, based on 100 parts by weight of the total composition, but is not limited thereto.
The auxiliary curing agent plays a role in enhancing the formation of radicals of the photoinitiator and the degree of curing of the film, and examples thereof include pentaerythritol tetrakis (3-mercaptopropionate), dioctyl phthalate, diisononyl phthalate, dioctyl adipate, tricresyl phosphate, and 2,2, 4-trimethyl-1, 3-pentanediol monoisobutyrate, 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5, -dimercapto-1, 3, 4-thiadiazole, 2-mercapto-4, 6-dimethylaminopyridine, and the like, and these may be used alone or in a mixture of two or more thereof, but are not necessarily limited thereto. When the auxiliary curing agent is contained in the photosensitive resin composition of the present invention, the content thereof may be appropriately adjusted as needed, and for example, it may be contained in an amount of 0.1 to 10 parts by weight, more specifically 0.2 to 8 parts by weight, and further specifically 0.4 to 5 parts by weight, based on 100 parts by weight of the total composition, but is not limited thereto.
The adhesion promoter plays a role in improving adhesion to a substrate, and may have a reactive substituent such as a vinyl group, a carboxyl group, a methacryloxy group, an isocyanate group, or an epoxy group in order to improve adhesion to a substrate. Examples of the adhesion promoter include trimethoxysilylbenzoic acid (trimethyoxysilylbenzoic acid), gamma-methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, gamma-isocyanatopropyltriethoxysilane, gamma-methacryloxypropyltrimethoxysilane, beta- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, and the like, and these may be used alone or in combination of two or more, but are not necessarily limited thereto. When the adhesion promoter is contained in the photosensitive resin composition of the present invention, the content thereof may be appropriately adjusted as needed, and for example, it may be contained in an amount of 0.1 to 10 parts by weight, more specifically 0.2 to 8 parts by weight, and further specifically 0.4 to 5 parts by weight, based on 100 parts by weight of the total composition, but is not limited thereto.
The surfactant plays a role of improving coatability or developability of the photosensitive resin composition, and the kind thereof is not particularly limited, and may be, for example, a fluorine-based surfactant or a silicon surfactant. Commercially available products of fluorine-based surfactants include BM-1000, BM-1100(BM Chemie), Fluorad FC-135/FC-170C/FC-430 (Sumitomo 3M Co., Ltd.), SH-28PA/-190/SZ-6032(Toray Silicone Co., Ltd.), and the like. Commercially available silicon surfactants include, but are not necessarily limited to, BYK-310, BYK-313, BYK-320, BYK-333, and the like available from BYK. When the surfactant is contained in the photosensitive resin composition of the present invention, the content thereof may be appropriately adjusted as needed, and for example, it may be contained in an amount of 0.01 to 5 parts by weight, more specifically 0.02 to 4 parts by weight, and further specifically 0.05 to 2 parts by weight, based on 100 parts by weight of the total composition, but is not limited thereto.
The photosensitive resin composition of the present invention can realize a fine pattern and can increase a residual film ratio, and thus is suitable for forming a columnar spacer, a black matrix, or a colored (e.g., black) columnar spacer, and thus can be used for various electronic components including OLED displays and TFT-LCD panels.
Therefore, according to another aspect of the present invention, there is provided a finely patterned cured product formed from the photosensitive resin composition of the present invention.
In one embodiment, the micropatterned cured object may be a columnar spacer, a black matrix, or a colored (e.g., black) columnar spacer.
The finely patterned cured product can be formed, for example, by a method of applying the photosensitive resin composition of the present invention on a substrate, and then pattern-exposing and developing the applied composition, but is not limited thereto.
The present invention will be described in more detail below with reference to examples. However, the scope of the present invention is not limited to these examples.
[ examples ]
Preparation example: preparation of adhesive resin
30 parts by weight of a monomer mixture in which methacrylic acid, methyl methacrylate, glycidyl methacrylate and benzyl acrylate were mixed, 1 part by weight of V-65(Wako Chemical company) as a thermal initiator, 1 part by weight of 3-Mercaptopropionic acid (3-Mercaptopropionic acid) as a chain transfer agent for adjusting molecular weight, and 68 parts by weight of methyl 3-methoxypropionate as an organic solvent were added to a reaction vessel in a molar ratio of 020:30:30:20, respectively, and then polymerization was performed by stirring for 8 hours while maintaining 65 ℃ under a nitrogen atmosphere, thereby preparing an acrylic polymer as a binder resin. The weight average molecular weight of the acrylic polymer prepared was 25000.
Examples 1 to 5 and comparative examples 1 to 9: preparation of photosensitive resin composition
A binder resin (13 parts by weight), a polymerizable compound having an unsaturated bond (26 parts by weight), a photopolymerization initiator, and a solvent (60 parts by weight) were added to a reaction mixing tank provided with an ultraviolet shielding film and a stirrer, and mixed under stirring at normal temperature, according to the composition shown in table 1 below. Thereafter, the mixed solution was filtered using a filter having a size of 0.5 μm, thereby preparing a photosensitive resin composition.
< description of Components of the composition used >
Binder resin: acrylic acid polymers obtained in preparation examples
DPHA: dipentaerythritol hexaacrylate (dipentaerythritolhritol hexaacrylate)
[ photoinitiator A ]
[ photoinitiator B ]
[ photoinitiator C ]
[OXE-01]
Solvent: 3-Methoxypropionic acid methyl ester (MMP)
[ Table 1]
The photosensitive resin compositions of the examples and comparative examples prepared above were coated on glass in a thickness of about 1.0 to 15.0 μm, respectively, and then the solvent present on the coated surface was primarily removed at a low pressure of 1.0 to 0.5 torr (torr), after which it was left on a hot plate at 80 to 110 ℃ for about 30 to 120 seconds, thereby removing the residual solvent.
The film prepared as described above was exposed to light, the exposed film was developed with an alkaline aqueous solution (tetramethylammonium hydroxide), and the formed pattern was then heat-treated in an oven at 150-250 ℃ for 30-90 minutes, thereby obtaining a final cured film having a fine pattern.
The following items were evaluated for each pattern of the examples and comparative examples obtained above.
1) Size of pattern
The dimensions of the pattern prepared above were measured using an SNU apparatus of SNU corporation.
2) Residual film rate
In the above-described method for producing a cured film, the ratio of the change in the thickness of the film before exposure to the thickness of the final cured film is calculated without interposing a mask, and the ratio is set as the residual film ratio.
Residual film ratio (%) [ thickness after curing/thickness before exposure ]. 100
The evaluation results of the above items are shown in table 2 below.
[ Table 2]
As can be seen from table 2, when the compositions of the examples and comparative examples are compared, as shown in fig. 1, the compositions of the examples show an excellent residual film ratio compared to the comparative examples under the same pattern size.
Further, as for the photoinitiator C, the photoinitiator C formed a high residual film rate as compared with OXE-01 (comparative example 7) which was currently used in large amounts while forming the same radical, as shown in FIG. 2, it is considered that this is because the area of the photoinitiator C absorbing light of the I-line (I-line) is wider than that of OXE-01.
Claims (10)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20190084627 | 2019-07-12 | ||
| KR10-2019-0084627 | 2019-07-12 | ||
| PCT/KR2020/009132 WO2021010683A1 (en) | 2019-07-12 | 2020-07-10 | Photosensitive resin composition |
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| CN114127637A true CN114127637A (en) | 2022-03-01 |
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| JP (1) | JP2022540658A (en) |
| KR (1) | KR20210008315A (en) |
| CN (1) | CN114127637A (en) |
| WO (1) | WO2021010683A1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2010054825A (en) * | 2008-08-28 | 2010-03-11 | Nof Corp | Alkali-developable negative resin composition |
| KR20110106287A (en) * | 2008-12-05 | 2011-09-28 | 아사히 가라스 가부시키가이샤 | Photocurable composition and method for producing a molded article having a fine pattern on the surface |
| WO2012132558A1 (en) * | 2011-03-25 | 2012-10-04 | 株式会社Adeka | Oxime ester compound and photoinitiator containing said compound |
| KR20160047550A (en) * | 2013-08-30 | 2016-05-02 | 닛산 가가쿠 고교 가부시키 가이샤 | Method for forming resist pattern, and composition for forming resist pattern |
| KR102190911B1 (en) * | 2014-07-15 | 2020-12-14 | 도쿄 오카 고교 가부시키가이샤 | Photosensitive composition and compound |
| TW201623225A (en) * | 2014-11-12 | 2016-07-01 | 三養公司 | Composition of black matrix photoresist for liquid crystal display panel |
| JP6464764B2 (en) * | 2015-01-16 | 2019-02-06 | Jsr株式会社 | Radiation-sensitive coloring composition, spacer, method for forming the same, and liquid crystal display device |
| KR102047079B1 (en) * | 2015-03-11 | 2019-12-02 | 동우 화인켐 주식회사 | A colored photo sensitive resin composition, color filter and liquid crystal display device having the same |
| KR101788399B1 (en) * | 2015-09-23 | 2017-10-19 | (주)경인양행 | Oxime ester compound having improved heat stability, photopolymerization initiator and photoresist composition comprising the same |
| WO2018060110A1 (en) * | 2016-09-28 | 2018-04-05 | Merck Patent Gmbh | Polymerisable liquid crystal material and polymerised liquid crystal film |
| JP6891880B2 (en) * | 2017-03-28 | 2021-06-18 | 東レ株式会社 | A photosensitive resin composition, a cured film, an element having a cured film, an organic EL display device having a cured film, a method for manufacturing a cured film, and a method for manufacturing an organic EL display device. |
| CN108727517B (en) * | 2017-04-25 | 2021-05-07 | 常州强力先端电子材料有限公司 | Fluorenoxime ester photoinitiator containing polymerizable group, and preparation method and application thereof |
| WO2018235665A1 (en) * | 2017-06-20 | 2018-12-27 | 株式会社Adeka | Polymerizable composition, photosensitive composition for black matrix, and photosensitive composition for black column spacer |
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