KR20140145407A - A colored photosensitive resin composition, color filter and display device comprising the same - Google Patents

A colored photosensitive resin composition, color filter and display device comprising the same Download PDF

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KR20140145407A
KR20140145407A KR1020130067821A KR20130067821A KR20140145407A KR 20140145407 A KR20140145407 A KR 20140145407A KR 1020130067821 A KR1020130067821 A KR 1020130067821A KR 20130067821 A KR20130067821 A KR 20130067821A KR 20140145407 A KR20140145407 A KR 20140145407A
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South Korea
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pigment
organic pigment
photosensitive resin
weight
resin composition
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KR1020130067821A
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Korean (ko)
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KR102024868B1 (en
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정보람
김훈식
이순아
이종수
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동우 화인켐 주식회사
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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
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/201—Filters in the form of arrays
    • 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
    • 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
    • G02F1/1303—Apparatus specially adapted to the manufacture of LCDs
    • 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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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Nonlinear Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Materials For Photolithography (AREA)

Abstract

The present invention relates to a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator and a solvent, wherein the colorant comprises a red organic pigment and a blue organic pigment, wherein the content of the blue organic pigment is larger than that of the red organic pigment To provide a colored photosensitive resin composition.

Description

TECHNICAL FIELD [0001] The present invention relates to a colored photosensitive resin composition, a color filter and a display device comprising the same,

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a colored photosensitive resin composition, a pattern including the same, and a display device.

A color filter may be embedded in a color imaging device of an image sensor such as a complementary metal oxide semiconductor (CMOS), a charge coupled device (CCD), etc., and may be used to actually obtain a color image . In addition, the color filter is widely used for a photographing element, a plasma display panel (PDP), a liquid crystal display (LCD), a field emission display (FEL), a light emitting display (LED) and the like. Particularly, in recent years, the use of LCDs has been further expanded, and accordingly, color filters have been recognized as one of the most important components in reproducing color tones of LCDs.

The color filter is prepared by 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-formed by spin coating and then heating and drying (hereinafter, (Hereinafter sometimes referred to as post-baking) is repeated for each color to form pixels of each color, as required. In recent years, a large-sized display has progressed at a high speed and a high contrast ratio is continuously required. Therefore, a method of using a dye instead of the pigment dispersion method, which was conventionally used as a coloring method of a colored photosensitive resin composition, or using a dye and a pigment simultaneously . However, a colored photosensitive resin composition for a color filter using a dye and a colored photosensitive resin composition for a hybrid type color filter using both a dye and a pigment simultaneously can provide a color filter excellent in transmittance. However, The sensitivity may be lowered depending on the kind of the ink. Therefore, studies have been actively made to solve the above problems and to prevent the sensitivity of the color filter from deteriorating.

On the other hand, Korean Patent Registration No. 10-0529638 discloses a photopolymerizable resin composition containing an N-phenylglycine and a triazine-based compound excellent in adhesion, resolution, surface margin and internal curability as an initiator, It seems to be insufficient for improving the sensitivity of the filter pattern formation.

Korean Patent Publication No. 10-2011-0052978 Japanese Patent No. 3924872

An object of the present invention is to provide a colored photosensitive resin composition capable of improving the defective residual rate of a pattern of a color filter generated in a process of depositing a conductive metal on the pattern top of a color filter during the process of manufacturing a liquid crystal display device. Another object of the present invention is to provide a color filter made of the above-mentioned colored photosensitive resin composition and having little change in coating film thickness even under high temperature conditions.

In order to achieve the above object,

A coloring agent, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator and a solvent, wherein the colorant comprises a red organic pigment and a blue organic pigment, wherein the content of the blue organic pigment is greater than the content of the red organic pigment A photosensitive resin composition is provided.

The present invention also provides a color filter which is manufactured from the colored photosensitive resin composition.

Further, the present invention provides a display device including the color filter.

The colored photosensitive resin composition of the present invention uses a mixture containing a blue organic pigment and a red organic pigment as a coloring agent to form a pattern having a small thickness change in the coating film even in the process of depositing a conductive metal at a high temperature Lt; / RTI > In addition, when the colored photosensitive resin composition is used, it is possible to manufacture a color filter of high reliability with a small color change rate.

Hereinafter, the present invention will be described in more detail.

The colored photosensitive resin composition of the present invention comprises a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator and a solvent, wherein the colorant comprises a red organic pigment and a blue organic pigment, wherein the content of the blue organic pigment is By weight.

The colorant is contained in an amount of 10 to 80% by weight, preferably 30 to 70% by weight, and more preferably 40 to 70% by weight based on the total weight of the solid content of the colored photosensitive resin composition. Exhibits an excellent retention rate in the above range, and exhibits high reliability.

The weight ratio of the red organic pigment to the blue organic pigment contained in the colorant is 10-49: 51-90, preferably 20-45: 55-80, more preferably 30-40: 60-70 .

Further, the colorant may further include a yellow organic pigment. In this case, the yellow organic pigment may be contained in an amount of 3 to 30 parts by weight based on 100 parts by weight of the total of the red organic pigment and the blue organic pigment, preferably 10 To 20 parts by weight.

The red organic pigment may be, for example, C.I. Pigment Red 177, C.I. Pigment Red 179, C.I. Pigment Red 202, C.I. Pigment Red 206, C.I. Pigment Red 207, C.I. Pigment Red 208, C.I. Pigment Red 209, C.I. Pigment Red 215, C.I. Pigment Red 216, C.I. Pigment Red 220, C.I. Pigment Red 224, C.I. Pigment Red 226, C.I. Pigment Red 242, C.I. Pigment Red 243, C.I. Pigment Red 245, C.I. Pigment Red 254, C.I. Pigment Red 255, C.I. Pigment Red 264 and C.I. Pigment Red 265, and among them, C.I. Pigment Red 179, C.I. Pigment Red 209, C.I. Pigment Red 242 and C.I. Pigment Red 254 is preferred.

The blue organic pigment may be, for example, C.I. Pigment Blue 15, C.I. Pigment Blue 15: 3, C.I. Pigment Blue 15: 4 and C.I. Pigment Blue 15: 6, and preferably at least one selected from the group consisting of C.I. Pigment Blue 15: 4 and C.I. Pigment Blue 15: 6, more preferably C.I. Pigment Blue 15: 6.

Further, the yellow organic pigment may be, for example, C.I. Pigment Yellow 138, C.I. Pigment Yellow 139 and C.I. Pigment yellow 150, and preferably at least one selected from the group consisting of C.I. Pigment Yellow 139 and C.I. Pigment Yellow 150.

The alkali-soluble resin should be soluble in the solvent of the present invention and reactive to the action of light or heat. The kind of the acrylic copolymer which functions as a binder resin for the colorant and is soluble in an alkaline developing solution can be used without particular limitation.

The alkali-soluble resin may be a copolymer of a carboxyl group-containing monomer and other monomer copolymerizable with the monomer. The carboxyl group-containing monomer may be, for example, an unsaturated carboxylic acid such as an unsaturated polycarboxylic acid having at least one carboxyl group in a molecule such as an unsaturated monocarboxylic acid, an unsaturated dicarboxylic acid or an unsaturated tricarboxylic acid. The unsaturated monocarboxylic acid may be, for example, acrylic acid, methacrylic acid, crotonic acid,? -Chloroacrylic acid, cinnamic acid, and the like. The unsaturated dicarboxylic acid may be, for example, maleic acid, fumaric acid, itaconic acid, citraconic acid and mesaconic acid. The unsaturated polycarboxylic acid may be an acid anhydride, specifically maleic anhydride, itaconic anhydride and citraconic anhydride. The unsaturated polycarboxylic acid may also be mono (2-methacryloyloxyalkyl) ester, and examples thereof include mono (2-acryloyloxyethyl) succinate, mono (2-methacryloyloxyethyl) ), Phthalic acid mono (2-acryloyloxyethyl), phthalic acid mono (2-methacryloyloxyethyl), and the like. In addition, the unsaturated polycarboxylic acid may be mono (meth) acrylate of a dicarboxylic polymer at both ends, for example,? -Carboxypolycaprolactone monoacrylate and? -Carboxypolycaprolactone monomethacrylate have. The carboxyl group-containing monomers may be used individually or in combination of two or more. Specific examples of the other monomers copolymerizable with the carboxyl group-containing monomer include styrene,? -Methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, p-chlorostyrene, o- P-methoxy styrene, o-vinyl benzyl methyl ether, m-vinyl benzyl methyl ether, p-vinyl benzyl methyl ether, o-vinyl benzyl glycidyl ether, m-vinyl benzyl glycidyl ether, Aromatic vinyl compounds such as vinylbenzyl glycidyl ether and indene; Methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, i-propyl acrylate, i-propyl methacrylate, butyl methacrylate, i-butyl acrylate, i-butyl methacrylate, sec-butyl acrylate, sec-butyl methacrylate, t-butyl acrylate, t-butyl methacrylate, Ethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate, 2-hydroxybutyl methacrylate, 3-hydroxybutyl acrylate, 3-hydroxybutyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, Acrylate, benzyl acrylate, benzyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, phenyl acrylate, phenyl methacrylate, 2-methoxyethyl acrylate, 2-methoxyethyl Methoxyethyl acrylate, methacrylate, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate, methoxy diethylene glycol acrylate, methoxy diethylene glycol methacrylate, methoxy triethylene glycol acrylate, methoxy triethylene glycol Methacrylate, methoxypropylene glycol acrylate, methoxypropylene glycol methacrylate, methoxydipropylene glycol acrylate, methoxydipropylene glycol methacrylate, isobornyl acrylate, isobornyl methacrylate, dicyclopenta Dienyl acrylate, dicyclopentadienyl methacrylate, 2-hydroxy-3-phenoxy Unsaturated carboxylic acid esters such as cyproxy acrylate, 2-hydroxy-3-phenoxypropyl methacrylate, glycerol monoacrylate and glycerol monomethacrylate; Aminoethyl methacrylate, 2-aminoethyl methacrylate, 2-dimethylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate, 2-aminopropyl acrylate, 2-aminopropyl methacrylate, 2- Unsaturated carboxylates such as methyl acrylate, ethyl acrylate, propyl methacrylate, isopropyl acrylate, isopropyl acrylate, isopropyl acrylate, isopropyl acrylate, isopropyl acrylate, Acid amino alkyl esters; Unsaturated carboxylic acid glycidyl esters such as glycidyl acrylate and glycidyl methacrylate; Carboxylic acid vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate and vinyl benzoate; Unsaturated ethers such as vinyl methyl ether, vinyl ethyl ether and allyl glycidyl ether; Vinyl cyanide compounds such as acrylonitrile, methacrylonitrile,? -Chloroacrylonitrile and vinylidene cyanide; Unsaturated amides such as acrylamide, methacrylamide,? -Chloroacrylamide, N-2-hydroxyethyl acrylamide and N-2-hydroxyethyl methacrylamide; Unsaturated imides such as maleimide, N-phenylmaleimide and N-cyclohexylmaleimide; Aliphatic conjugated dienes such as 1,3-butadiene, isoprene and chloroprene; Polystyrene, polymethyl acrylate, polymethyl methacrylate, poly-n-butyl acrylate, poly-n-butyl methacrylate, polysiloxane having a monoacryloyl group or monomethacryloyl group at the end of the polymer molecular chain Macromers and the like. These monomers may be used individually or in combination of two or more.

Therefore, the alkali-soluble resin is preferably a copolymer of (meth) acrylic acid / methyl (meth) acrylate, (meth) acrylic acid / benzyl (meth) acrylate copolymer, (meth) acrylic acid / 2-hydroxyethyl (Meth) acrylate / polymethyl (meth) acrylate / benzyl (meth) acrylate copolymer, a (meth) acrylic acid / methyl (meth) acrylate / polystyrene macromonomer copolymer, (Meth) acrylic acid / benzyl (meth) acrylate / polystyrene macromonomer copolymer, (meth) acrylic acid / benzyl (meth) acrylate / polymethyl (meth) acrylate macromonomer copolymer, (Meth) acrylic acid / 2-hydroxyethyl (meth) acrylate / benzyl (meth) acrylate / polystyrene macromonomer copolymer, Acrylic acid / styrene / benzyl (meth) acrylate / N-phenylmaleimide copolymer, (meth) acrylic acid / succinic acid mono (2-acryloyloxy) acrylate / polymethyl (meth) acrylate macromonomer copolymer, Acrylic acid / succinic acid mono (2-acryloyloxyethyl) / styrene / allyl (meth) acrylate / N-phenylmaleimide copolymer / styrene / benzyl (Meth) acrylic acid / benzyl (meth) acrylate / N-phenylmaleimide / styrene / glycerol mono (meth) acrylate copolymer. The (meth) acrylate means acrylate or methacrylate.

 (Meth) acrylic acid / benzyl (meth) acrylate copolymer, (meth) acrylic acid / benzyl (meth) acrylate / styrene copolymer, (meth) acrylic acid / methyl Methacrylic acid / methyl (meth) acrylate / styrene copolymer is preferably used.

The alkali-soluble resin should have a weight average molecular weight of 5,000 to 50,000, preferably 8,000 to 40,000, more preferably 10,000 to 10,000, as measured by gel permeation chromatography (GPC) using tetrahydrofuran as an eluting solvent. To 30,000. When the weight average molecular weight of the alkali-soluble resin is in the range of 5,000 to 50,000, the hardness of the coating film is improved, the residual film ratio is excellent, and the good solubility of the developer in the unexposed area and the improved resolution can be shown. Also, the acid value should be 50 to 150 (mgKOH / g), preferably 60 to 140, and more preferably 80 to 130. Within the acid value range, the alkali-soluble resin has improved solubility in a developing solution, so that the unexposed portion can be easily dissolved and highly sensitized, and a pattern of the exposed portion can remain to improve the residual film ratio. The alkali-soluble resin may be contained in an amount of 5 to 80% by weight, and preferably 10 to 60% by weight based on the total solid weight of the colored photosensitive resin composition. If the thickness is out of the above range, the residual film rate and reliability may be deteriorated and pattern formation may not be easy.

The photopolymerizable compound is a compound that can be polymerized by an active radical or an acid generated from a photopolymerization initiator upon irradiation with light, and may be a monofunctional or polyfunctional polymerizable compound depending on the number of functional groups. Examples of the monofunctional polymerizable compound include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate and N- Lt; / RTI > Examples of the bifunctional polymerizable compound include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (Meth) acrylate, hexanediol di (meth) acrylate, diethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, Acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, Pentyl glycol diacrylate and propyloxylate neopentyl glycol diacrylate, and the like. Examples of the trifunctional polymerizable compound include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, ethoxylate trimethylolpropane tri (meth) acrylate, propyloxytrimethylolpropane tri ) Acrylate, glyceryl propoxylate triacrylate, isocyanurate triarylate, and the like. Examples of the tetrafunctional polymerizable compound include pentaerythritol tetra (meth) acrylate and dimethylol propane tetra (methyl) acrylate. The pentafunctional polymerizable compound may be dipentaerythritol penta (meth) acrylate, and the hexafunctional photopolymerizable compound may be dipentaerythritol hexa (meth) acrylate. Of these, as the photopolymerizable compound, a bifunctional or higher functional polyfunctional polymerizable compound can be preferably used, and in particular, a polyfunctional polymerizable compound having five or more functionalities can be preferably used.

The photopolymerizable compound is contained in an amount of 5 to 50% by weight, and more preferably 7 to 45% by weight based on the total weight of the solid content of the colored photosensitive resin composition. When the photopolymerizable compound is contained in the range as described above, the strength and smoothness of the pixel portion can be improved.

The photopolymerization initiator can be used without limitation as long as it can polymerize the alkali-soluble resin and the photopolymerizable compound. The photopolymerization initiator may be divided into an active radical generator which generates an active radical upon irradiation with light, a sensitizer, and an acid generator.

Examples of the active radical generator include acetophenone, benzoin, benzophenone, thioxanthone, triazine, and oxime compounds. Specific examples of the acetophenone-based compound include diethoxyacetophenone, 2-methyl-2-morpholino-1- (4-methylthiophenyl) propan- 2-methyl-1- [4- (2-hydroxyethoxy) phenyl] propan-1-one, 1-hydroxycyclohexyl phenyl ketone And oligomers of 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propan-1-one and the like, Can be used in combination with a photopolymerization initiator. Further, acetophenone-based 2-methyl-2-morpholino-1- (4-methylthiophenyl) propan-1-one is preferred. Specific examples of the benzoin-based compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether. Specific examples of the benzophenone compound include benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3 ', 4,4'-tetra (t -Butylperoxycarbonyl) benzophenone, and 2,4,6-trimethylbenzophenone. Specific examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2, 4-diethylthioxanthone, 2,4-dichlorothioxanthone and 1-chloro-4-propoxythioxanthone, and the like. Specific examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) 6,4-bis (trichloromethyl) -6- (4-methoxystyryl) -1,3,5-triazine, , 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5- Yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino- -Methylphenyl) ethenyl] -1,3,5-triazine and 2,4-bis (trichloromethyl) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5 -Triazine, and the like.

Specific examples of the oxime-based compound include 2- (O-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione, 1- (4-methylsulfanyl-phenyl) -butan-1-one oxime-O-acetate, hydroxyimino- ) -Acetic acid ethyl ester-O-acetate and hydroxyimino- (4-methylsulfanyl-phenyl) -acetic acid ethyl ester-O-benzoate.

Specific examples of the sensitizer include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,2-bis (o-chlorophenyl) -4,4 ', 5,5'-tetraphenyl- 2-chloroacridone, 2-ethyl anthraquinone, benzyl, 9,10-phenanthrenequinone, camphorquinone, methyl phenylglyoxylate and titanocene compounds, etc. .

Specific examples of the acid generator include 4-hydroxyphenyldimethylsulfonium p-toluene sulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluene sulfone 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyl iodonium p-toluenesulfonate and diphenyl iodonium p- Diphenyl iodonium hexafluoroantimonate and the like, and nitrobenzyl tosylates, benzoin tosylates, and the like.

Among these compounds, there are compounds which simultaneously generate an active radical and an acid such as a triazine-based compound.

The photopolymerization initiator may be contained in an amount of 0.1 to 40 parts by weight, preferably 1 to 30 parts by weight based on 100 parts by weight of the total of the alkali-soluble resin and the photopolymerizable compound based on the solid content. Within the above range, the colored photosensitive resin composition is highly sensitized, the exposure time is shortened, productivity is improved, and high resolution can be maintained. In addition, the strength of the pixel portion formed using the composition and the smoothness of the surface of the pixel portion can be improved.

The solvent is not particularly limited as long as it dissolves the colored photosensitive resin composition, and in particular, ethers, aromatic hydrocarbons, ketones, alcohols, esters or amides are preferable. Specific examples thereof include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol di Butyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, dipropylene glycol dipropyl ether and dipropylene glycol Ethers such as dibutyl ether; 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; Methylcellosolve acetate, ethylcellosolve acetate, ethyl acetate, butyl acetate, amyl acetate, methyl lactate, ethyl lactate, butyl lactate, 3-methoxypropionate, methyl 3-methoxypropionate, Methoxybutyl acetate, ethylene glycol monoacetate, ethylene glycol diacetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol Monoacetate, diethylene glycol diacetate, diethylene glycol monobutyl ether acetate, propylene glycol monoacetate, propylene glycol diacetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene carbonate, propylene carbonate, Lactone Esters and the like. The solvent may be a mixture of one or more selected from the group consisting of the solvents exemplified above. In view of coatability and dryness, the solvent should have a boiling point of 100 to 200 ° C, and propylene glycol monomethyl ether acetate, Propylene glycol monoethyl ether acetate, cyclohexanone, ethyl lactate, butalactate, ethyl 3-ethoxypropionate and methyl 3-methoxypropionate are preferable.

The solvent is contained in an amount of 25 to 80% by weight, preferably 30 to 70% by weight based on the total weight of the colored photosensitive resin composition. When it is applied in the above-described range with a coating device such as a roll coater, a spin coater, a slit and spin coater, a slit coater (or a die coater) and a kett, good coating properties can be shown.

The present invention provides a color filter made of the colored photosensitive resin composition. The colored photosensitive resin composition may be coated on a substrate, and the pattern may be formed by photo-curing and developing.

First, the colored photosensitive resin composition is coated on a substrate or a layer composed of a solid component of a photosensitive resin composition, followed by heating and drying to remove volatile components such as a solvent to obtain a smooth coated film.

The coating method may be carried out by a spin coating method, a flexible coating method, a roll coating method, a slit and spin coating method, a slit coating method, or the like. After application, heating and drying (prebaking), or drying under reduced pressure to evaporate the volatile components such as solvent. The heating temperature is 70 to 200 캜, preferably 80 to 130 캜. The thickness of the coating film after drying by heating is about 1 to 8 占 퐉. Ultraviolet rays are applied to the coating film through a mask to form a desired pattern. At this time, it is preferable to use an apparatus such as a mask aligner or a stepper to uniformly irradiate a parallel light beam onto the entire exposed portion and align the exact position of the mask and the substrate. When ultraviolet light is irradiated, the site irradiated with ultraviolet light is cured. G-line (wavelength: 436 nm), h-line and i-line (wavelength: 365 nm) may be used as the ultraviolet ray. The dose of ultraviolet rays can be appropriately selected according to need, and the present invention is not limited thereto. When the coating film after curing is brought into contact with a developing solution to dissolve and develop the non-visible portion, a spacer having a desired pattern shape can be obtained.

Examples of the developing method include a liquid addition method, a dipping method, a spray method, and the like, and are not particularly limited. Further, the substrate may be inclined at an arbitrary angle during development. The developer is an aqueous solution containing an alkaline compound and a surfactant. The alkaline compound is an inorganic or organic alkaline compound. The inorganic alkaline compound is selected from the group consisting of sodium hydroxide, potassium hydroxide, disodium hydrogenphosphate, sodium dihydrogen phosphate, ammonium dihydrogen phosphate, ammonium dihydrogen phosphate, potassium dihydrogen phosphate, sodium silicate, potassium silicate, sodium carbonate, , Potassium hydrogencarbonate, sodium borate, potassium borate and ammonia. The organic alkaline compound may also be selected from the group consisting of tetramethylammonium hydroxide, 2-hydroxyethyltrimethylammonium hydroxide, monomethylamine, dimethylamine, trimethylamine, monoethylamine, diethylamine, triethylamine, monoisopropylamine , Diisopropylamine and ethanolamine. The inorganic and organic alkaline compounds may be used individually or in combination of two or more. The concentration of the alkaline compound in the alkali developing solution is preferably 0.01 to 10% by weight, more preferably 0.03 to 5% by weight.

The surfactant in the alkali developer may be at least one selected from the group consisting of a nonionic surfactant, an anionic surfactant, and a cationic surfactant.

Examples of the nonionic surfactant include polyoxyethylene alkyl ethers, polyoxyethylene aryl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene derivatives, oxyethylene / oxypropylene block copolymers, sorbitan fatty acid esters, polyoxyethylene sorbitan Fatty acid esters, polyoxyethylene sorbitol fatty acid esters, glycerin fatty acid esters, polyoxyethylene fatty acid esters and polyoxyethylene alkylamines.

Examples of the anionic surfactant include higher alcohol sulfuric acid ester salts such as sodium lauryl alcohol sulfate ester and sodium oleyl alcohol sulfate ester, alkylsulfates such as sodium laurylsulfate or ammonium laurylsulfate, sodium dodecylbenzenesulfonate or dodecylnaphthalene And alkylarylsulfonic acid salts such as sodium sulfonate.

Examples of the cationic surfactant include amine salts such as stearylamine hydrochloride and lauryltrimethylammonium chloride, and quaternary ammonium salts. These surfactants may be used individually or in combination of two or more.

The concentration of the surfactant in the developer is 0.01 to 10% by weight, preferably 0.05 to 8% by weight, and more preferably 0.1 to 5% by weight. After development, the substrate is washed with water, and if necessary baked at 150 to 230 DEG C for 10 to 60 minutes.

By using the photosensitive resin composition of the present invention, a specific pattern can be formed on the substrate through each of the steps as described above.

Further, the present invention can provide a display device including the color filter. The display device is excellent in visible light shielding property, and has high heat resistance and chemical stability (solvent resistance) because of its excellent adhesion to a substrate due to its high crosslinking density even at a low exposure dose.

Hereinafter, the present invention will be described in more detail with reference to Synthesis Examples, Examples and Experimental Examples. However, the following Synthesis Examples, Examples and Experimental Examples are for illustrating the present invention, and the scope of the present invention is not limited to the following Synthesis Examples, Examples and Experimental Examples.

Synthetic example  1. Preparation of alkali-soluble resin

A flask equipped with a stirrer, a thermometer reflux condenser, a dropping funnel and a nitrogen inlet tube was prepared. As a monomer dropping lot, a mixture 40 of 3,4-epoxytricyclodecan-8-yl (meth) acrylate and 3,4-epoxytricyclodecan-9-yl (meth) acrylate in a molar ratio of 50:50 50 parts by weight of methyl methacrylate, 40 parts by weight of acrylic acid, 70 parts by weight of vinyltoluene, 4 parts by weight of t-butylperoxy-2-ethylhexanoate, and 40 parts by weight of propylene glycol monomethyl ether acetate (PGMEA) And stirring was prepared. As a chain transfer agent dropping tank, 6 parts by weight of n-dodecanethiol and 24 parts by weight of PGMEA were added to prepare stirring. Thereafter, 395 parts by weight of PGMEA was added to the flask, and the atmosphere in the flask was replaced with nitrogen in air, and the temperature of the flask was raised to 90 DEG C with stirring. The monomer and the chain transfer agent were then started to be added dropwise from the dropping funnel. The temperature was raised to 110 DEG C for 1 hour and maintained for 5 hours to obtain a resin (B-1) having a solid acid value of 75 mgKOH / g.

The weight average molecular weight (Mw) and number average molecular weight (Mn) of the alkali-soluble resin were measured by the GPC method under the following conditions.

HLC-8120GPC (manufactured by TOSOH CORPORATION) apparatus was used. TSK-GELG4000HXL and TSK-GELG2000HXL columns were connected in series and the temperature of the column was set at 40 ° C. Tetrahydrofuran was used as mobile phase solvent and flow rate was measured at 1.0 mL / min flow rate. The concentration of the measurement sample was 0.6% by weight, and the injection amount was 50 μL, and analyzed using an RI detector. As the standard materials for calibration, TSK STANDARD POLYSTYRENE F-40, F-4, F-1, A-2500 and A-500 (manufactured by TOSOH CORPORATION) The average molecular weight was measured.

The weight average molecular weight measured by GPC in terms of polystyrene was 17,000 and the molecular weight distribution (Mw / Mn) was 2.3.

Example  1 to 8 and Comparative Example  1 to 5. Preparation of colored photosensitive resin composition

A colored photosensitive resin composition was prepared according to a conventional method with the components and compositions shown in Tables 1 and 2 below. Table 1 is a colored photosensitive resin composition using a red organic pigment and a blue organic pigment as a colorant, and Table 2 is a colored photosensitive resin composition using a red organic pigment, a blue organic pigment and a yellow organic pigment as colorants.

division Example Comparative Example One 2 3 One 2 (A-1) Red organic pigment 23 - - 37 (A-2) Red organic pigment - 23 20 - 45 (A-3) Blue organic pigment 37 - - 23 (A-4) Blue organic pigment - 37 40 45 (B) an alkali-soluble resin 30.0 30.0 30.0 30.0 30.0 (C) Photopolymerizable compound 26.0 27.0 25.0 25.0 26.0 (D) Photopolymerization initiator 4.0 3.0 5.0 5.0 4.0 (E) Solvent 100.0 100.0 100.0 100.0 100.0

division Example Comparative Example 4 5 6 7 8 3 4 5 (A-1) Red organic pigment 17 - - - - - (A-2) Red organic pigment - 17 12 17 28 35 10 30 (A-3) Blue organic pigment 35 - - 35 17 30 (A-4) Blue organic pigment - 35 40 50 - 6 - (A-5) Yellow organic pigment 8 8 8 8 12 8 4 (B) an alkali-soluble resin 30.0 30.0 30.0 30.0 30.0 30.0 30.0 30.0 (C) Photopolymerizable compound 26.0 27.0 25.0 25.0 26.0 25.0 26.0 27.0 (D) Photopolymerization initiator 4.0 3.0 5.0 5.0 4.0 5.0 4.0 3.0 (E) Solvent 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0

The compositions of Table 1 and Table 2 are as follows.

Red organic pigment (A-1): C.I. Pigment Red 179 (Shanghai Mole Chemical Co., Ltd., China)

Red organic pigment (A-2): C.I. Pigment Red 254 (TCI, Japan)

Blue organic pigment (A-3): C.I. Pigment Blue 15: 6 (Hangzhou Xcolor, China)

Blue organic pigment (A-4): C.I. Pigment Blue 15: 4 (LANSCO COLORS, USA)

Yellow organic pigment (A-5): C.I. Pigment Yellow 150 (LANSCO COLORS, USA)

Alkali-soluble resin (B): The resin of Synthesis Example 1

Photopolymerizable compound (C): dipentaerythritol hexaacrylate (KAYARD DPHA; manufactured by Nippon Kayaku Co., Ltd.)

Photopolymerization initiator (D-1): 2-O-benzoyloxime-1- [4- (phenylthio) phenyl] -1,2-octanedione (OXE-

Photopolymerization initiator (D-2): 2-Methyl-2-morpholino-1- (4-methylthiophenyl) propan-1-one (Irgacure 907 (Ciba Specialty Chemical)

Solvent (E): Propylene glycol monomethyl ether acetate

Experimental Example  One. Measuring specimen (Color filter) production

A glass substrate (Eagle 2000; Corning) having a width of 2 inches and a length of 2 inches was sequentially washed with a neutral detergent, water and alcohol, and then dried. The colored photosensitive resin compositions prepared in the above Examples and Comparative Examples were each spin-coated on the glass substrate, and then pre-baked in a clean oven at 90 占 폚 for 3 minutes. After the prebaked substrate was cooled to room temperature, the spacing between the substrate and the quartz glass photomask was adjusted to 10 mu m, exposure was performed at an exposure dose of 60 mJ / cm2 (based on 365 nm) using an exposure apparatus (TME-150RSK; Topcon Co., Respectively. The irradiation of the polymerizable resin composition at this time was carried out by using radiation from an ultra-high pressure mercury lamp. At this time, a photomask in which patterns are formed on the same plane was used. (Pattern) of one side having a width of 10 mu m to 100 mu m, and the spacing of the square was 100 mu m. After light irradiation, the coating film was immersed in an aqueous developing solution containing 0.12% by weight of a nonionic surfactant and 0.04% by weight of potassium hydroxide at 25 캜 for 100 seconds and developed. After washing with water, post-baking was performed in an oven at 220 캜 for 20 minutes Respectively. The obtained film thickness was 3 占 퐉. The film thickness was measured using a film thickness measuring apparatus (DEKTAK 6M; Veeco).

Experimental Example  2. Residual film ratio  Measure

The color filters prepared from the colored photosensitive resin compositions of Examples 1 to 5 and Comparative Examples 1 to 3 were measured at room temperature (23 ° C) and high temperature (230 ° C) to confirm the change in film thickness. The results are shown in Table 3 below.

Film Thickness (μm) Rate of change (%) Room temperature (23 DEG C) (A) High temperature (230 DEG C) (B) Example 1 2.30 2.26 -1.74 Example 2 2.30 2.25 -2.17 Example 3 2.30 2.27 -1.30 Example 4 2.30 2.25 -2.17 Example 5 2.30 2.27 -1.30 Example 6 2.30 2.28 -0.87 Example 7 2.30 2.24 -2.61 Example 8 2.30 2.29 -0.43 Comparative Example 1 2.30 1.80 -21.74 Comparative Example 2 2.30 1.75 -23.91 Comparative Example 3 2.30 1.73 -24.78 Comparative Example 4 2.30 1.92 -16.52 Comparative Example 5 2.30 1.82 -20.87

Figure pat00001

The colored photosensitive resin compositions of Examples 1 to 8 showed a slight decrease in thickness at high temperatures, but the colored photosensitive resin compositions of Comparative Examples 1 to 5 showed a high reduction rate. Therefore, it can be said that the color photosensitive resin compositions of Examples 1 to 8 have excellent residual film ratios.

Experimental Example  3. Reliability Evaluation

The color filter further prepared at the exposure amount of 40 mJ / cm 2 and 150 mJ / cm 2 was immersed in the SPS-250EL solvent of BASF Co. for 10 minutes at 35 캜 for 10 minutes, The color change was compared and evaluated. Table 4 shows the results calculated by the following equation representing the color change in the three-dimensional colorimetric system defined by L *, a *, b *. The smaller the color change value is, the more reliable the color filter can be manufactured.

△ Eab * = [(△ L *) 2 + (△ a *) 2 + (△ b *) 2] (1/2)


 Example Comparative Example One 2 3 4 5 6 7 8 One 2 3 4 5 Exposure dose
(mJ / cm 2 ) 150 150 150 150 150 150 150 150 150 150 150 150 150 △ Eab * 1.7 1.9 1.8 1.8 1.6 1.9 1.7 1.9 4.7 4.4 4.5 4.8 4.4 Exposure dose
(mJ / cm 2 ) 60 60 60 60 60 60 60 60 60 60 60 60 60 △ Eab * 1.9 2.2 2.0 2.1 2.1 2.3 2.2 2.3 5.7 6.5 5.9 Exposure dose
(mJ / cm 2 ) 40 40 40 40 40 40 40 40 40 40 40 40 40 △ Eab * 2.4 2.4 2.3 2.5 2.4 2.6 2.3 2.6 7.8 8.1 8.0 7.7 7.4

Although the color change value was higher as the exposure amount was lowered, good color change values were shown in Examples 1 to 8, while higher color change values were shown in Comparative Examples 1 to 5. Therefore, it can be said that the colored photosensitive resin compositions of Examples 1 to 8 showed high reliability.

Claims (10)

A colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent,
Wherein the colorant comprises a red organic pigment and a blue organic pigment, and the content of the blue organic pigment is greater than the content of the red organic pigment. The photosensitive resin composition according to claim 1, which comprises 10 to 80% by weight of a colorant, 5 to 80% by weight of an alkali-soluble resin and 5 to 50% by weight of a photopolymerizable compound based on the total weight of solid components in the colored photosensitive resin composition, Wherein the solvent comprises from 0.1 to 40 parts by weight based on 100 parts by weight of the total of the alkali-soluble resin and the photopolymerizable compound, and the solvent comprises 25 to 80% by weight based on the total weight of the colored photosensitive resin composition. The colored photosensitive resin composition according to claim 1, wherein the weight ratio of the red organic pigment to the blue organic pigment is 10 to 49: 51 to 90. The color photosensitive resin composition according to claim 2, wherein the colorant further comprises a yellow organic pigment, and the yellow organic pigment is contained in an amount of 3 to 30 parts by weight based on 100 parts by weight of the total of the red organic pigment and the blue organic pigment. Composition. The method of claim 1, wherein the red organic pigment is selected from the group consisting of C.I. Pigment Red 179, C.I. Pigment Red 209, C.I. Pigment Red 242 and C.I. Pigment Red 254. The colored photosensitive resin composition according to claim 1, The method of claim 1, wherein the blue organic pigment is selected from the group consisting of C.I. Pigment Blue 15: 4 and C.I. Pigment Blue 15: 6. ≪ RTI ID = 0.0 > 11. < / RTI > The method of claim 4, wherein the yellow organic pigment is selected from the group consisting of C.I. Pigment Yellow 139 and C.I. Pigment Yellow 150. 15. The colored photosensitive resin composition according to claim 1, The colored photosensitive resin composition according to claim 1, wherein the alkali-soluble resin has a polystyrene-reduced weight average molecular weight of 5,000 to 50,000 and an acid value of 50 to 150 (mgKOH / g). A color filter produced by the colored photosensitive resin composition of claim 1. A display device comprising the color filter of claim 9.
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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20170087330A (en) * 2016-01-20 2017-07-28 동우 화인켐 주식회사 Colored photosensitive resin composition for red pixel

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3924872B2 (en) 1997-04-28 2007-06-06 住友化学株式会社 Red composition for color filter and color filter
KR20100031617A (en) * 2007-07-17 2010-03-23 클라리언트 파이넌스 (비브이아이)리미티드 Fine-particle epsilon copper phthalocyanine pigment preparation
KR20110052978A (en) 2009-11-13 2011-05-19 동우 화인켐 주식회사 Red colored photosensitive resin composition, color filter and liquid crystal display device having the same
KR20110103601A (en) * 2010-03-15 2011-09-21 동우 화인켐 주식회사 A black photosensitive resin composition, color filter and liquid crystal display device having the same
KR20120019039A (en) * 2010-08-24 2012-03-06 동우 화인켐 주식회사 Colored photosensitive resin composition, color filter and liquid crystal display device having the same

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3924872B2 (en) 1997-04-28 2007-06-06 住友化学株式会社 Red composition for color filter and color filter
KR20100031617A (en) * 2007-07-17 2010-03-23 클라리언트 파이넌스 (비브이아이)리미티드 Fine-particle epsilon copper phthalocyanine pigment preparation
KR20110052978A (en) 2009-11-13 2011-05-19 동우 화인켐 주식회사 Red colored photosensitive resin composition, color filter and liquid crystal display device having the same
KR20110103601A (en) * 2010-03-15 2011-09-21 동우 화인켐 주식회사 A black photosensitive resin composition, color filter and liquid crystal display device having the same
KR20120019039A (en) * 2010-08-24 2012-03-06 동우 화인켐 주식회사 Colored photosensitive resin composition, color filter and liquid crystal display device having the same

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20170087330A (en) * 2016-01-20 2017-07-28 동우 화인켐 주식회사 Colored photosensitive resin composition for red pixel

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