KR20140100264A - Colored photosensitive resin composition - Google Patents
Colored photosensitive resin composition Download PDFInfo
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- KR20140100264A KR20140100264A KR1020130013374A KR20130013374A KR20140100264A KR 20140100264 A KR20140100264 A KR 20140100264A KR 1020130013374 A KR1020130013374 A KR 1020130013374A KR 20130013374 A KR20130013374 A KR 20130013374A KR 20140100264 A KR20140100264 A KR 20140100264A
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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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
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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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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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
- G03F7/20—Exposure; Apparatus therefor
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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
- G03F7/20—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
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- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Nonlinear Science (AREA)
- Optics & Photonics (AREA)
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Materials For Photolithography (AREA)
Abstract
Description
The present invention relates to a colored photosensitive resin composition.
BACKGROUND ART [0002] Color filters are widely used in imaging devices, liquid crystal display devices, and the like, and their application range is rapidly expanding. A color filter used for a color liquid crystal display device, an image pickup device, or the like is a device for uniformly applying a colored photosensitive resin composition containing a coloring agent corresponding to each color of red, green and blue on a substrate on which a black matrix is pattern- The coating film formed by heating and drying (hereinafter also referred to as preliminary firing) may be exposed and developed, and if necessary, further heat curing (hereinafter also referred to as post-firing) may be repeated for each color, Color pixels are formed.
As the coloring agent in the colored photosensitive resin composition, a pigment dispersion system is generally used. For this purpose, a pigment dispersion method is used. As the pigment dispersion method, there is a method of producing a color filter by photolithography using a coloring and radiation-sensitive composition in which pigments are dispersed in various photosensitive compositions. This method has been widely used as a preferable method for producing a color filter for a large-screen and high-resolution color display because it can secure sufficient reliability against light or heat since a pigment is used.
However, in recent years, the size of display has been rapidly increasing, and high contrast ratio has been continuously demanded. However, in the conventional pigment dispersing system, the limit of pigment particleization has reached a limit and due to problems such as color unevenness due to coarse particles, A method of simultaneously using a pigment and a dye has been studied (Korean Patent No. 10-881860).
However, when a color filter is produced by using a colored photosensitive resin composition containing a dye as a coloring agent, the light resistance and heat resistance of the dye are poor, so that color shifts occur frequently, and the development speed is slow and sensitivity is low. There is a problem that the formed pattern is peeled off during the process.
It is an object of the present invention to provide a colored photosensitive resin composition capable of producing a color filter excellent in heat resistance and solvent resistance.
It is an object of the present invention to provide a colored photosensitive resin composition capable of producing a color filter having high luminance.
1. a colorant, an alkali-soluble resin, a photopolymerizable compound, a crosslinking agent, a photopolymerization initiator and a solvent; Wherein the colorant comprises a dye represented by the following formula (1); Wherein the crosslinking agent comprises a compound represented by the following formula (2) or (3):
[Chemical Formula 1]
(2)
(Wherein R 1 and R 2 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 4 to 10 carbon atoms, A is an alkyl group having 1 to 6 carbon atoms, an alkoxyalkyl group having 1 to 6 carbon atoms, An aliphatic or aromatic ring having 2 to 6 carbon atoms, substituted or unsubstituted, with or without an ether group, a ketone group or an ester group, with or without a hetero atom)
(3)
(Wherein R 1 and R 2 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 4 to 10 carbon atoms, A is an alkyl group having 1 to 6 carbon atoms, an alkoxyalkyl group having 1 to 6 carbon atoms, An aliphatic or aromatic ring having 2 to 6 carbon atoms, substituted or unsubstituted, with or without an ether group, a ketone group or an ester group, with or without a hetero atom).
2. The colored photosensitive resin composition according to 1 above, wherein the dye represented by Formula 1 is contained in an amount of 10 to 90% by weight based on the total weight of the colorant.
3. The colored photosensitive resin composition according to 1 above, wherein the crosslinking agent represented by the above formula (2) or (3) has a structure represented by the following formulas (4) to (7)
[Chemical Formula 4]
[Chemical Formula 5]
[Chemical Formula 6]
(7)
Wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 independently represent a hydrogen atom, a straight or branched An alkyl group or a cycloalkyl group having 4 to 10 carbon atoms).
4. The colored photosensitive resin composition according to 1 above, wherein the photopolymerization initiator is at least one selected from the group consisting of an acetophenone-based, triazine-based, biimidazole-based and oxime-based compound.
5. The colored photosensitive resin composition according to item 1, further comprising at least one photopolymerization initiation auxiliary selected from the group consisting of an amine compound, a carboxylic acid compound and an organic sulfur compound having a thiol group.
6. The photosensitive resin composition according to any one of 1 to 5 above, wherein the amount of the colorant is 5 to 70 wt%, the amount of the alkali-soluble resin is 5 to 80 wt%, the amount of the photopolymerizable compound is 5 to 45 wt% Is comprised between 5 and 45% by weight; The photopolymerization initiator comprises 0.1 to 40% by weight based on the total amount of the alkali-soluble resin and the photopolymerizable compound based on the solid content; Wherein the solvent comprises 60 to 90% by weight of the total weight of the colored photosensitive resin composition.
7. A color filter made of a colored photosensitive resin composition according to any one of the above 1 to 6.
8. A liquid crystal display device comprising the color filter of 7 above.
The colored photosensitive resin composition of the present invention can produce a color filter excellent in heat resistance and solvent resistance and can minimize color change even after exposure to high temperature conditions or through a number of chemical treatment steps in the manufacturing process.
The color filter made of the colored photosensitive resin composition of the present invention has excellent brightness.
The present invention includes a colorant, an alkali-soluble resin, a photopolymerizable compound, a crosslinking agent, a photopolymerization initiator and a solvent; The colorant comprises a dye represented by the formula (1); Since the crosslinking agent contains the compound represented by the general formula (2) or (3), it is possible to manufacture a color filter excellent in heat resistance and solvent resistance, and can be used for a long period of time under high temperature conditions, To a colored photosensitive resin composition capable of producing a color filter excellent in luminance.
Hereinafter, the present invention will be described in detail.
The colored photosensitive resin composition of the present invention includes a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.
<Colorant>
The colorant comprises a dye represented by the following formula (1): < EMI ID =
[Chemical Formula 1]
When the dye represented by the formula (1) is contained, the luminance of the color filter produced therefrom is improved.
The content of the dye represented by the formula (1) is not particularly limited and may be, for example, 10 to 90% by weight, preferably 15 to 85% by weight, of the total weight of the colorant. When the content of the dye represented by the general formula (1) is within the above range, the luminance improving effect can be maximized.
The colorant according to the present invention may be an organic pigment, an inorganic pigment or a mixture thereof, which is commonly used in the art within the scope of the present invention, in addition to the above-mentioned dyes.
The organic pigment is not particularly limited and may be a pigment used for printing ink, inkjet ink, etc. Specific examples thereof include water-soluble azo pigments, insoluble azo pigments, phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, Anthanthrone pigments, indanthrone pigments, pravanthrone pigments, anthraquinone pigments, anthraquinone pigments, anthanthrone pigments, anthanthrone pigments, indanthrone pigments, indanthrone pigments, Pyranthrone pigments, diketopyrrolopyrrole pigments, and the like. These may be used alone or in combination of two or more.
The inorganic pigment is not particularly limited and may be a metal compound such as a metal oxide or a metal complex salt and specifically includes a group consisting of iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony and carbon black ≪ / RTI > These may be used alone or in combination of two or more.
Organic pigments and inorganic pigments are compounds classified as pigments in the color index (The Society of Dyers and Colourists), and specifically C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264 and 265; C.I. Pigment Green 7, 10, 15, 25, 36, 47 and 58 and the like. These may be used alone or in combination of two or more.
The content of the colorant is not particularly limited and may be, for example, from 5 to 70% by weight, and preferably from 10 to 50% by weight, based on the total weight of the colorant based on the solid content. When the content of the colorant is within the above range, the color density of the pixel is sufficient and the non-curing portion of the non-cured portion is not deteriorated during development, so that the occurrence of the residue can be reduced.
<Alkali-soluble resin>
The alkali-soluble resin is polymerized including an ethylenically unsaturated monomer having a carboxyl group. The ethylenically unsaturated monomer having a carboxyl group is a component that imparts solubility to an alkali developing solution used in a developing treatment process for forming a pattern.
The ethylenically unsaturated monomer having a carboxyl group is not particularly limited, and examples thereof include monocarboxylic acids such as acrylic acid, methacrylic acid and crotonic acid; Dicarboxylic acids such as fumaric acid, mesaconic acid and itaconic acid, and anhydrides thereof; mono (meth) acrylates of a polymer having a carboxyl group and a hydroxyl group at both terminals such as? -carboxypolycaprolactone mono (meth) acrylate, and the like, preferably acrylic acid and methacrylic acid. These may be used alone or in combination of two or more.
The alkali-soluble resin according to the present invention may further comprise at least one other monomer copolymerizable with the monomer. Methylstyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, o-vinylbenzyl methyl ether, m-vinylbenzyl methyl ether, p- Aromatic vinyl compounds such as vinyl benzyl methyl ether, o-vinyl benzyl glycidyl ether, m-vinyl benzyl glycidyl ether and p-vinyl benzyl glycidyl ether; N-cyclohexylmaleimide, N-benzylmaleimide, N-phenylmaleimide, No-hydroxyphenylmaleimide, Nm-hydroxyphenylmaleimide, Np-hydroxyphenylmaleimide, No-methylphenylmaleimide, Nm N-substituted maleimide-based compounds such as methylphenyl maleimide, Np-methylphenyl maleimide, No-methoxyphenyl maleimide, Nm-methoxyphenyl maleimide and Np-methoxyphenyl maleimide; Propyl (meth) acrylate, n-butyl (meth) acrylate, i-butyl (meth) acrylate, alkyl (meth) acrylates such as sec-butyl (meth) acrylate and t-butyl (meth) acrylate; (Meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, tricyclo [5.2.1.0 2,6] decan- Alicyclic (meth) acrylates such as dicyclopentanyloxyethyl (meth) acrylate and isobornyl (meth) acrylate; Aryl (meth) acrylates such as phenyl (meth) acrylate and benzyl (meth) acrylate; 3- (methacryloyloxymethyl) -2-trifluoromethyl oxetane, 3- (methacryloyloxymethyl) oxetane, 3- (methacryloyloxymethyl) 2- (methacryloyloxymethyl) oxetane, 2- (methacryloyloxymethyl) -4-trifluoromethyloxetane, and the like Unsaturated oxetane compounds, and the like. These may be used alone or in combination of two or more.
The molecular weight distribution (weight average molecular weight (Mw) / number average molecular weight (Mn)) of the alkali-soluble resin is not particularly limited and may be, for example, from 1.5 to 6.0, and preferably from 1.8 to 4.0. When the molecular weight distribution of the alkali-soluble resin is within the above range, the developability can be excellent.
The content of the alkali-soluble resin may be 5 to 80% by weight, preferably 10 to 70% by weight based on the solid content of the colored photosensitive resin composition. When the content of the alkali-soluble resin is within the above range, solubility in a developing solution is sufficient and pattern formation is easy, and reduction of the film of the pixel portion of the exposed portion is prevented during development, so that the missing property of the non-pixel portion is improved.
One embodiment of the method for producing an alkali-soluble resin is as follows.
0.1 to 10% of a polymerization initiator is added to a 0.5 to 20-fold amount of the monomer, monomer, and monomers in the flask having the stirrer, the thermometer, the reflux condenser, the dropping funnel and the nitrogen- . Thereafter, the mixture is stirred at 40 to 140 DEG C for 1 to 10 hours.
As the solvent, those used in the conventional radical polymerization can be used. Specific examples of the solvent include tetrahydrofuran, dioxane, ethyleneglycol dimethylethyl, diethyleneglycol dimethylethyl, acetone, methylethylketone, methylisobutylketone, cyclohexanone Propanol, n-butanol, ethylene glycol monomethyl ether, propylene glycol monomethyl ether, toluene, xylene, ethylbenzene, methylene chloride, ethyl acetate, butyl acetate, propyleneglycol monomethyl ethyl acetate, 3-methoxybutyl acetate, Chloroform, dimethylsulfoxide, and the like, or a mixture thereof.
The polymerization initiator may be a polymerization initiator commonly used in the art and is not particularly limited. Specific examples thereof include diisopropylbenzene hydroperoxide, di-t-butyl peroxide, benzoyl peroxide, t-butyl peroxyisopropyl carbonate, t-amyl peroxy-2-ethylhexanoate, Organic peroxides such as 2-ethylhexanoate; Azo compounds such as 2,2'-azobis (isobutyronitrile), 2,2'-azobis (2,4-dimethylbarenonitrile) and dimethyl 2,2'-azobis (2-methylpropionate) Nitrogen compounds and the like. These may be used alone or in combination of two or more.
In the above process, an alpha -methylstyrene dimer or a mercapto compound may be used as a chain transfer agent to control the molecular weight. The? -methylstyrene dimer or the mercapto compound may be used in an amount of 0.005 to 5 parts by weight based on 100 parts by weight of the monomer. The above-mentioned polymerization conditions may be appropriately adjusted depending on the production equipment or the amount of heat generated by polymerization and the like.
< Photopolymerization Compound >
The photopolymerizable compound is a component for enhancing the strength of the pattern, and may include 1 to 6 functional monomers. For example, monofunctional compounds such as nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate and N- Monomer; (Meth) acrylates such as 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di 3-methylpentanediol di (meth) acrylate, 3- (acryloyloxy) -2-hydroxypropyl methacrylate, 2-hydroxy-1,3-dimethacryloxypropane, Bifunctional monomers such as 2-hydroxy-1-acryloxy-3-methacryloxypropane; Trifunctional monomers such as trimethylolpropane tri (meth) acrylate and pentaerythritol tri (meth) acrylate; Tetrafunctional monomers such as pentaerythritol tetra (meth) acrylate; Pentafunctional monomers such as dipentaerythritol penta (meth) acrylate; And hexafunctional monomers such as dipentaerythritol hexa (meth) acrylate. These may be used alone or in combination of two or more.
The photopolymerizable compound may preferably be a bifunctional or higher functional monomer and, more preferably, a pentafunctional or higher functional monomer in view of enhancement of pattern strength and improvement in smoothness.
Examples of commercially available photopolymerizable compounds include 701 (NK ESTER), 701A (NK ESTER), ATMM-3L (NK ESTER) and KAYARAD DPHA (Nippon Kayaku).
The content of the photopolymerizable compound is not particularly limited within a range that the sum of the hydroxyl groups of the alkali-soluble resin and the alkali-soluble resin falls within the above range, and may be, for example, 5 to 45% by weight based on the solid content of the total amount of the photosensitive resin composition By weight, preferably 10 to 35% by weight. When the content of the photopolymerizable compound is within the above range, the strength and smoothness of the pixel portion can be good.
< Cross-linking agent >
The crosslinking agent includes a compound represented by the following formula 2 or 3:
(2)
(Wherein R 1 and R 2 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 4 to 10 carbon atoms, A is an alkyl group having 1 to 6 carbon atoms, an alkoxyalkyl group having 1 to 6 carbon atoms, An aliphatic or aromatic ring having 2 to 6 carbon atoms, substituted or unsubstituted, with or without an ether group, a ketone group or an ester group, with or without a hetero atom)
(3)
(Wherein R 1 and R 2 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 4 to 10 carbon atoms, A is an alkyl group having 1 to 6 carbon atoms, an alkoxyalkyl group having 1 to 6 carbon atoms, An aliphatic or aromatic ring having 2 to 6 carbon atoms, substituted or unsubstituted, with or without an ether group, a ketone group or an ester group, with or without a hetero atom).
The heteroatom may be a nitrogen, oxygen, phosphorus or sulfur atom.
Generally, it is necessary to improve the heat resistance and solvent resistance according to the environment of use and the conditions of the production process, etc. When the crosslinking agent represented by the general formula (2) or (3) is used in combination with the dye represented by the general formula (1), heat resistance and solvent resistance Especially.
The crosslinking agent represented by the general formula (2) or (3) preferably has the structure represented by the following general formulas (4) to (7).
[Chemical Formula 4]
[Chemical Formula 5]
[Chemical Formula 6]
(7)
Wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 independently represent a hydrogen atom, a straight or branched An alkyl group or a cycloalkyl group having 4 to 10 carbon atoms).
The content of the crosslinking agent is not particularly limited and may be, for example, from 5 to 45% by weight, and preferably from 10 to 35% by weight, based on the solid content of the total amount of the colored photosensitive resin composition. When the content of the crosslinking agent is within the above range, the effect of improving heat resistance and solvent resistance can be maximized. The strength and smoothness of the pixel portion can be improved.
< Light curing Initiator >
The type of the photopolymerization initiator is not particularly limited as long as it can initiate polymerization of the photopolymerizable compound, and may be a photopolymerization initiator commonly used in the art. Examples thereof include acetophenone, triazine, biimidazole ), Oxime compounds, and the like. These may be used alone or in combination of two or more.
The acetophenone compound is not particularly limited and includes, for example, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethylketal, 2- (2-hydroxyethoxy) phenyl] -2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2- 1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan- ] Propane-1-one, and 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinophenyl) butan-1-one.
The triazine compound is not particularly limited, and examples thereof include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4- Methyl) -6- (4-methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2 , 2,4-bis (trichloromethyl) -6- [2- (5-methylpiperazin-1-yl) Yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (furan- (Trichloromethyl) -6- [2- (4-diethylamino-2-methylphenyl) ethenyl] -1,3,5-triazine, 2,4-bis (Trichloromethyl) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine.
The imidazole-based compound is not particularly limited, and examples thereof include 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,3-dichlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2-chlorophenyl) -4,4' Phenyl) imidazole, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetra (trialkoxyphenyl) biimidazole, 2,2- Phenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole or an imidazole compound in which the phenyl group at the 4,4', 5,5 'position is substituted with a carboalkoxy group , And preferably 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,3-dichlorophenyl ) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2-bis (2,6-dichlorophenyl) -4,4,5,5'-tetraphenyl- Imidazole and the like.
The oxime-based compound is not particularly limited, and examples thereof include o-ethoxycarbonyl- alpha -oximimino-1-phenylpropan-1-one, compounds represented by the following formulas 8 to 10, and the like.
[Chemical Formula 8]
[Chemical Formula 9]
[Chemical formula 10]
The photopolymerization initiator according to the present invention may further include a photopolymerization initiator commonly used in the art within the scope of the present invention in addition to the above-mentioned compounds, and examples thereof include benzoin, benzophenone, thioxanthone , Anthracene-based compounds, and the like. These may be used alone or in combination of two or more.
The benzoin compound is not particularly limited, and examples thereof include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether.
The benzophenone compound is not particularly limited, and examples thereof include benzophenone, methyl 0-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'- methyldiphenylsulfide, 3,3 ' -Tetra (tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone, and the like.
The thioxanthone compound is not particularly limited and includes, for example, 2-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1- Oakstone, and the like.
The anthracene compound is not particularly limited and includes, for example, 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10- Anthracene and the like.
Other examples include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 10-butyl-2-chloroacridone, 2-ethylanthraquinone, benzyl, 9,10-phenanthrenequinone, camphorquinone, phenylclyoxylic acid Methyl, titanocene compounds, and the like.
The content of the photopolymerization initiator is not particularly limited and may be, for example, from 0.1 to 40% by weight, preferably from 1 to 30% by weight, based on the total amount of the alkali-soluble resin and the photopolymerizable compound based on the solid content . When the content of the photopolymerization initiator is within the above range, the colored photosensitive resin composition becomes highly sensitive and the exposure time is shortened, so that productivity is improved and high resolution can be maintained, and the strength of the formed pixel portion and the smoothness on the surface of the pixel portion can be improved have.
< Light curing Initiation supplements>
The colored photosensitive resin composition of the present invention may further include a photopolymerization initiation auxiliary agent for improving the sensitivity.
The photopolymerization initiation auxiliary is not particularly limited, and examples thereof include an amine compound, a carboxylic acid compound, and an organic sulfur compound having a thiol group. These may be used alone or in combination of two or more.
The amine compound is not particularly limited, and examples thereof include aliphatic amine compounds such as triethanolamine, methyldiethanolamine and triisopropanolamine; 4-dimethylaminobenzoic acid ethyl, 4-dimethylaminobenzoic acid isoamyl, 4-dimethylaminobenzoic acid 2-ethylhexyl, benzoic acid 2-dimethylaminoethyl, N, N-dimethylparatoluidine, Aromatic amine compounds such as 4'-bis (dimethylamino) benzophenone and 4,4'-bis (diethylamino) benzophenone.
The carboxylic acid compound is not particularly limited and includes, for example, phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, And aromatic heteroacetic acids such as phenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.
The organic sulfur compound having a thiol group is not particularly limited and examples thereof include 2-mercaptobenzothiazole, 1,4-bis (3-mercaptobutyryloxy) butane, 1,3,5-tris (1H, 3H, 5H) -triene, trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis (3-mercaptopropionate), tetraethylene glycol bis (3-mercaptobutyrate), pentaerythritol tetrakis (3-mercaptopropionate), dipentaerythritol hexakis Phonate), and the like.
The content of the photopolymerization initiator is not particularly limited and may be, for example, from 0.1 to 50% by weight, preferably from 1 to 40% by weight, based on the total amount of the alkali-soluble resin and the photopolymerizable compound based on the solid content have. When the content of the photopolymerization initiator is within the above range, the sensitivity of the colored photosensitive resin composition is further improved, and productivity to be formed therefrom can be improved.
<Solvent>
The solvent is not particularly limited as long as it can dissolve the above components, and examples thereof include ethers, aromatic hydrocarbons, ketones, alcohols and esters. These may be used alone or in combination of two or more.
For example, ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether and ethylene glycol monobutyl ether; Diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, propylene glycol monomethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monomethyl ether Ethers such as acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxybutyl acetate, and methoxypentyl acetate; Aromatic hydrocarbons such as benzene, toluene, xylene, and mesitylene; Ketones such as methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, and cyclohexanone; Alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol and glycerin; And esters such as ethyl 3-ethoxypropionate, methyl 3-methoxypropionate and? -Butyrolactone. Of these, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, Ethyl lactate, butalactate, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, and the like.
The solvent is preferably an organic solvent having a boiling point of 100 占 폚 to 200 占 폚 in view of coatability and dryness.
The content of the solvent is not particularly limited and includes, for example, a solvent contained in the colorant dispersion. The total content of the solvent may be 60 to 90% by weight of the total weight of the colored photosensitive resin composition, preferably 70 to 85% %. ≪ / RTI > When the content of the solvent is within the above range, the coating property may be good.
<Additives>
The colored photosensitive resin composition of the present invention may further contain at least one additive selected from the group consisting of a dispersant, another polymer compound, a curing agent, a surfactant, an adhesion promoter, an antioxidant, an ultraviolet absorber and an anti-
The dispersing agent is added for maintaining the deagglomeration and stability of the pigment and the dye, and any of those generally used in the art can be used without limitation. Preferably an acrylate-based dispersant comprising BMA (butyl methacrylate) or DMAEMA (N, N-dimethylaminoethyl methacrylate); Polycarboxylic acid esters; Unsaturated polyamides; Polycarboxylic acids; (Partial) amine salts of polycarboxylic acids; Ammonium salts of polycarboxylic acids; Alkylamine salts of polycarboxylic acids; Polysiloxanes; Long chain polyaminoamide phosphate salts; Esters of hydroxyl group-containing polycarboxylic acids and their modification products; An amide formed by the reaction of a polyester having a free carboxyl group with a poly (lower alkyleneimine) or a salt thereof; Soluble resin or water-soluble polymer compound such as (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylate ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol or polyvinylpyrrolidone; Polyester; Modified polyacrylates; Adducts of ethylene oxide / propylene oxide; Phosphate esters and the like. These may be used alone or in combination of two or more.
DISPER BYK-161, DISPER BYK-162, DISPER BYK-163, DISPER BYK-164, DISPER BYK-166, DISPER BYK-171, DISPER BYK- DISPER BYK-182, DISPER BYK-184, DISPER BYK-2000, DISPER BYK-2001, DISPER BYK-2070, DISPER BYK-2150 (BYK KEMISA); EFKA-44, EFKA-44, EFKA-47, EFKA-48, EFKA-4010, EFKA-4050, EFKA-4055, EFKA-4020, EFKA-4015, EFKA- 4400, EFKA-4406, EFKA-4510, EFKA-4800 (BASF); SOLSPERS-24000, SOLSPERS-32550, NBZ-4204/10 (Lubirzol); Hinoact T-6000, Hinoact T-7000, Hinoact T-8000 (Kawaken Fine Chemicals); AJISPUR PB-821, Ajisper PB-822, Ajisper PB-823 (Ajinomoto); FLORENE DOPA-17HF, Florene DOPA-15BHF, Florene DOPA-33 and Florene DOPA-44 (Kyoeisha Chemical Co., Ltd.). These may be used alone or in combination of two or more.
The content of the dispersing agent is not particularly limited and may be, for example, 5 to 60 parts by weight, preferably 15 to 50 parts by weight, based on 100 parts by weight of the pigment based on the solid content. When the content of the dispersing agent is within the above range, the pigment can be finely atomized and the red colorant can have an appropriate viscosity.
The other polymer compound is not particularly limited, and examples thereof include curable resins such as epoxy resin and maleimide resin, polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl acrylate, polyester, Thermoplastic resins and the like.
The curing agent is a component for increasing deep curing and mechanical strength, and the type thereof is not particularly limited, and examples thereof include epoxy compounds, polyfunctional isocyanate compounds, melamine compounds, and oxetane compounds.
The epoxy compound is not particularly limited and includes, for example, bisphenol A epoxy resin, hydrogenated bisphenol A epoxy resin, bisphenol F epoxy resin, hydrogenated bisphenol F epoxy resin, novolak epoxy resin, other aromatic epoxy resin, Epoxy resins, glycidyl ester resins, glycidyl amine resins, or brominated derivatives of such epoxy resins; Aliphatic, alicyclic or aromatic epoxy compounds other than epoxy resins and brominated derivatives thereof; Butadiene (co) polymeric epoxide; Isoprene (co) polymeric epoxide; Glycidyl (meth) acrylate (co) polymers; Triglycidyl isocyanurate and the like.
The oxetane compound is not particularly limited and includes, for example, carbonate bisoxetane, xylene bisoxetane, adipate bisoxetane, terephthalate bisoxetane, cyclohexanedicarboxylic acid bisoxetane and the like .
The curing agent may be used together with a curing agent in combination with a curing auxiliary compound capable of ring-opening polymerization of the epoxy group of the epoxy compound and the oxetane skeleton of the oxetane compound.
The curing auxiliary compound is not particularly limited, and examples thereof include polyvalent carboxylic acids, polyvalent carboxylic acid anhydrides, and acid generators. Commercially available polyvalent carboxylic acid anhydrides can be used as an epoxy resin curing agent.
The commercially available epoxy resin curing agent that can be used in the present invention is not particularly limited and includes, for example, a trade name (Adeka Hadona EH-700) (manufactured by Adeka Kogyo Co., Ltd.), a trade name (Rikashido HH) Ltd.) and a trade name (MH-700) (manufactured by Shin-Etsu Chemical Co., Ltd.).
The surfactant is a component for improving the film-forming property of the photosensitive resin composition, and the kind thereof is not particularly limited, and examples thereof include a fluorine surfactant, a silicone surfactant, or a mixture thereof.
The silicone surfactant is not particularly limited, and examples thereof include DC3PA, DC7PA, SH11PA, SH21PA, and SH8400 of Dow Corning Toray Silicone Co., Ltd.; TS F-4440, TSF-4300, TSF-4445, TSF-4446, TSF-4460 and TSF-4452 of GE Toshiba Silicones.
Examples of the fluorochemical surfactant include, but are not limited to, Megapis F-470, F-471, F-475, F-482 and F-489 commercially available from Dainippon Ink and Chemicals, Incorporated.
Examples of the adhesion promoter include, but are not limited to, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) Aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyl (meth) acrylate, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3- methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanatepropyltrimethoxysilane, 3-isocyanatepropyltriethoxysilane, and the like. These may be used alone or in combination of two or more.
The content of the adhesion promoter is not particularly limited and may be, for example, 0.01 to 10% by weight, preferably 0.05 to 2% by weight based on the total weight of the colored photosensitive resin composition based on the solid content.
The kind of the antioxidant is not particularly limited and includes, for example, 2,2'-thiobis (4-methyl-6-t-butylphenol), 2,6- .
The type of ultraviolet absorber is not particularly limited, and examples thereof include 2- (3-tert-butyl-2-hydroxy-5-methylphenyl) -5-chlorobenzothiazole and alkoxybenzophenone.
The anti-aggregation agent is not particularly limited and may be, for example, sodium polyacrylate.
≪ Method for producing colored photosensitive resin composition >
Examples of the method for preparing the colored photosensitive resin composition of the present invention include a method in which a colorant and a dispersant are added to and dispersed in a solvent to prepare a colorant dispersion having a uniform particle diameter and then an alkali soluble resin dissolved in a solvent, A photopolymerization initiator and, if necessary, other additives, etc. are mixed and mixed with the dispersion of the colorant and, if necessary, the solvent is added again.
<Color filter>
The present invention also provides a color filter made of the colored photosensitive resin composition.
The color filter includes a substrate and a color layer formed on the substrate.
The substrate may be a substrate of the color filter itself, or may be a portion where the color filter is placed on a display device or the like, and is not particularly limited. The substrate may be glass, silicon (Si), silicon oxide (SiO x ), or a polymer substrate. The polymer substrate may be polyethersulfone (PES) or polycarbonate (PC).
The color layer may be a layer containing the colored photosensitive resin composition of the present invention, and may be a layer formed by applying the colored photosensitive resin composition and exposing, developing, and thermosetting the colored photosensitive resin composition in a predetermined pattern.
The color filter including the substrate and the color layer as described above may further include a partition wall formed between each color pattern, and may further include a black matrix. Further, it may further comprise a protective film formed on the color layer of the color filter.
<Liquid Crystal Display Device>
The present invention also relates to a liquid crystal display device provided with the color filter.
The liquid crystal display device of the present invention may include a configuration known to those skilled in the art without the color filter, and is not particularly limited in the present invention.
It is to be understood that both the foregoing general description and the following detailed description of the present invention are exemplary and explanatory and are intended to be illustrative of the invention and are not intended to limit the scope of the claims. It will be apparent to those skilled in the art that such variations and modifications are within the scope of the appended claims.
Example And Comparative Example .
A colored photosensitive resin composition having the composition and the content (parts by weight) of the following Table 1 was prepared.
(A)
(B)
(C)
(D)
(E)
(F)
(G)
A-4
1.29
E-2 /
E-3
0.3 /
0.8
F-2
12
G-2 /
G-3
0.1 /
0.01
A-4
1.29
E-2 /
E-3
0.3 /
0.8
F-2
12
G-2 /
G-3
0.1 /
0.01
A-3
2
E-2 /
E-3
0.3 /
0.8
F-2
12
G-2 /
G-3
0.1 /
0.01
A-3
1.29
E-2 /
E-3
0.3 /
0.8
F-2
12
G-2 /
G-3
0.1 /
0.01
A-4
1.29
E-2 /
E-3
0.3 /
0.8
F-2
/ 12
G-2 /
G-3
0.1 /
0.01
A-3: CI Pigment Yellow 138, A-4: Suncron yellow 10GN (Oh Young Ind.),
B: a copolymer of methacrylic acid and benzyl methacrylate having a molar ratio of methacrylic acid unit to benzyl methacrylate unit of 31:69, a weight average molecular weight of 30,000 and an acid value of 105 mgKOH / g,
C: dipentaerythritol hexaacrylate (KAYARAD DPHA, Nippon Kayaku Co., Ltd.),
D: 1,3,4,6-tetrakis (methoxymethyl) tetrahydroimidazo [4,5-d] imidazol-2,5 (lh, 3h) -dione (Powderlink 1174,
E-1: 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropane-1-one (I-369,
E-2: Eab-f (manufactured by Ciba),
E-3: 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine (N-1919,
F-1: Propylene glycol monomethyl ether acetate,
F-2: ethyl 3-ethoxypropionate,
G-1: SH8400 (Dow Donington Silicones),
G-2: DISPER BYK-2001 (BYK),
G-3: 3-methacryloxypropyltrimethoxysilane
Experimental Example .
Each of the colored photosensitive resin compositions prepared in Examples and Comparative Examples was applied on a glass substrate (EAGLE XG, manufactured by Corning Incorporated) having a 2-inch square by spin coating, then placed on a heating plate and maintained at a temperature of 100 캜 for 3 minutes To form a thin film. Subsequently, a test photomask having a pattern for changing the transmittance in the range of 1 to 100% to a step-like pattern and a line / space pattern of 1 to 50 m was placed on the thin film and the distance between the test photomask and the test photomask was set to 100 m. Respectively. At this time, the ultraviolet light source was irradiated at a light intensity of 100 mJ / cm 2 using a 1 kW high pressure mercury lamp containing g, h and i lines. The thin film irradiated with ultraviolet rays was immersed in a KOH aqueous solution of pH 10.5 for 2 minutes to develop. The glass plate coated with the thin film was washed with distilled water, dried by blowing nitrogen gas, and heated in a heating oven at 220 ° C for 1 hour to prepare a color filter. The film thickness of the prepared color filter was 2.0 mu m.
(1) Luminance measurement
The luminance Y was measured from the same color coordinates (Gx = 0.222, Gy = 0.662) of the manufactured color filter using a microspectrophotometer OSP-SP2000. The measurement results are shown in Table 2 below.
○: Y is 35 or more
X: Y is less than 35
(2) Solvent resistance evaluation
The prepared color filter was immersed in NMP (1-methyl-2-pyrrolidone) for 30 minutes to measure the color change before and after the immersion, and the solvent resistance was evaluated according to the following criteria. And L *, a * and b * in the equation (1) represent the color change in the three-dimensional colorimeter. The results are shown in Table 2 below.
[Equation 1]
△ Eab * = (△ L * ) 2 + (△ a *) 2 + (△ b *) 2] (1/2)
?: Eab * is 1 to 2;
?:? Eab * is more than 2 and not more than 3.
X: △ Eab * exceeds 3.
(3) Evaluation of heat resistance
The fabricated color filter was allowed to stand in an oven at 230 DEG C for 2 hours, and heat resistance was evaluated by color change before and after the heat treatment. And L *, a * and b * in the equation (1) represent the color change in the three-dimensional colorimeter. The results are shown in Table 2 below.
[Equation 1]
△ Eab * = (△ L * ) 2 + (△ a *) 2 + (△ b *) 2] (1/2)
?: Eab * is 1 to 2;
?:? Eab * is more than 2 and not more than 3.
X: △ Eab * exceeds 3.
Referring to Table 2, it can be confirmed that the color filters prepared from the colored photosensitive resin compositions of Examples 1 and 2 have excellent brightness, excellent solvent resistance and heat resistance.
However, the color filters prepared with the compositions of Comparative Examples 1 and 2, which do not include the dyes represented by Chemical Formula 1, have poor brightness and the color filters prepared with the composition of Comparative Example 3 which does not include a crosslinking agent have a somewhat solvent resistance Fell and the heat resistance was significantly reduced.
Claims (8)
Wherein the colorant comprises a dye represented by the following formula (1);
Wherein the crosslinking agent comprises a compound represented by the following formula (2) or (3):
[Chemical Formula 1]
(2)
(Wherein R 1 and R 2 are independently of each other a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 4 to 10 carbon atoms;
A is an aliphatic or aromatic ring having 2 to 6 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, an alkoxyalkyl group having 1 to 6 carbon atoms, or an amino group, with or without an ether group, a ketone group or an ester group, With or without an atom)
(3)
(Wherein R 1 and R 2 are independently of each other a hydrogen atom, an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 4 to 10 carbon atoms;
A is an aliphatic or aromatic ring having 2 to 6 carbon atoms which is substituted or unsubstituted with an alkyl group having 1 to 6 carbon atoms, an alkoxyalkyl group having 1 to 6 carbon atoms, or an amino group, with or without an ether group, a ketone group or an ester group, With or without atoms).
[Chemical Formula 4]
[Chemical Formula 5]
[Chemical Formula 6]
(7)
Wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 and R 10 independently represent a hydrogen atom, a straight or branched An alkyl group or a cycloalkyl group having 4 to 10 carbon atoms).
Wherein the colorant comprises 5 to 70% by weight,
The alkali-soluble resin may contain 5 to 80% by weight,
The photopolymerizable compound is contained in an amount of 5 to 45% by weight,
The cross-linking agent comprises from 5 to 45% by weight;
The photopolymerization initiator comprises 0.1 to 40% by weight based on the total amount of the alkali-soluble resin and the photopolymerizable compound based on the solid content;
Wherein the solvent comprises 60 to 90% by weight of the total weight of the colored photosensitive resin composition.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160091524A (en) * | 2015-01-23 | 2016-08-03 | 삼성디스플레이 주식회사 | Photosensitive resin composition and display device |
| KR20170111655A (en) * | 2016-03-29 | 2017-10-12 | 동우 화인켐 주식회사 | Colored photosensitive resin composition for organic light emitting diodes, color filter and image display device produced using the same |
| KR20180027372A (en) * | 2016-09-06 | 2018-03-14 | 스미또모 가가꾸 가부시키가이샤 | Compound useful as colorant |
| KR20180027371A (en) * | 2016-09-06 | 2018-03-14 | 스미또모 가가꾸 가부시키가이샤 | Colored composition |
-
2013
- 2013-02-06 KR KR1020130013374A patent/KR20140100264A/en not_active Application Discontinuation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160091524A (en) * | 2015-01-23 | 2016-08-03 | 삼성디스플레이 주식회사 | Photosensitive resin composition and display device |
| KR20170111655A (en) * | 2016-03-29 | 2017-10-12 | 동우 화인켐 주식회사 | Colored photosensitive resin composition for organic light emitting diodes, color filter and image display device produced using the same |
| KR20180027372A (en) * | 2016-09-06 | 2018-03-14 | 스미또모 가가꾸 가부시키가이샤 | Compound useful as colorant |
| KR20180027371A (en) * | 2016-09-06 | 2018-03-14 | 스미또모 가가꾸 가부시키가이샤 | Colored composition |
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