KR102397093B1 - A photosensitive resin composition, color filter and display device comprising the same - Google Patents

Abstract

The present invention relates to a colored photosensitive resin composition comprising a colorant, an alkali-soluble resin, a photopolymerizable compound, a photoinitiator, a solvent, and nano silica, and has excellent reliability.

Description

Colored photosensitive resin composition, color filter and display device including same

The present invention relates to a colored photosensitive resin composition, a color filter and a display device comprising the same, and more particularly, a colored photosensitive resin composition with excellent reliability comprising a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, a solvent, and nano silica , to a color filter and a display device including the same.

Electronic display devices used in office automation equipment, portable small televisions, and video camera viewfinders include liquid crystal display (LCD), plasma display panel (PDP), organic light emitting diode (OLED) diode:OLED) are being used, and related technology research is being actively conducted.

The liquid crystal display device has advantages such as light weight, thinness, low cost, low power consumption, and excellent adhesion to integrated circuits, and thus the range of its use is expanding for notebook computers, monitors, and TV images. Such a liquid crystal display device includes a lower substrate on which a black matrix, a color filter, and an ITO pixel electrode are formed, an active circuit portion consisting of a liquid crystal layer, a thin film transistor, and a capacitor layer, and an upper substrate on which the ITO pixel electrode is formed.

The color filter is manufactured by coating a fine area colored with three or more colors on a solid-state imaging device or a transparent substrate. Such a colored thin film is usually formed by a dyeing method, an electrodeposition method, a pigment dispersion method, etc., but recently, a pigment dispersion method excellent in heat resistance and durability is used.

The pigment dispersion method is a method in which a colored thin film is formed by repeating a series of processes of coating, exposing, developing, and thermally curing a photopolymerizable composition containing a colorant on a transparent substrate provided with a light blocking layer (black matrix). The pigment dispersion method has the advantage of improving heat resistance and durability, which are the most important properties of a color filter, and maintaining a uniform thickness of the film.

The colored photosensitive resin composition used for manufacturing a color filter according to the pigment dispersion method is generally composed of a binder resin, a photopolymerizable monomer, a photopolymerization initiator, an epoxy resin, a solvent, and other additives.

Recently, the market demand for a high-quality display with high color reproducibility is increasing, and accordingly, the content of the colorant in the colored photosensitive resin composition used in the manufacture of color filters is continuously increasing, and various kinds of colorants are used outside the existing colorants. use is being considered.

Among them, triphenylmethane or triarylmethane-based colorants have advantages of high molar extinction coefficient, excellent colorability, and high color purity. However, compared to the colorant used in the past, the reliability is insufficient, and improvement is needed.

An object of the present invention is to provide a colored photosensitive resin composition having improved reliability.

Moreover, an object of this invention is to provide the colored photosensitive resin composition excellent in transmittance|permeability, solvent resistance, and adhesiveness.

Another object of the present invention is to provide a color filter and a display device manufactured using the colored photosensitive resin composition.

In order to achieve the above object,

The present invention is a colored photosensitive resin composition comprising a colorant, an alkali-soluble resin, a photopolymerizable compound, a photoinitiator, a solvent and nano silica,

The colorant includes at least one selected from the group consisting of triphenylmethane and triarylmethane-based compounds,

The photopolymerization initiator provides a colored photosensitive resin composition comprising an oxime ester-based compound.

In addition, the present invention provides a color filter prepared from the colored photosensitive resin composition.

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

The colored photosensitive resin composition of the present invention has excellent reliability and has an effect of high color reproduction.

In addition, the colored photosensitive resin composition of the present invention has an excellent effect of transmittance, solvent resistance and adhesiveness.

In addition, the color filter and the display device made of the colored photosensitive resin composition of the present invention have an excellent effect of color reproduction.

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

The present invention is a colored photosensitive resin composition comprising a colorant, an alkali-soluble resin, a photopolymerizable compound, a photoinitiator, a solvent and nano silica,

The colorant includes at least one selected from the group consisting of triphenylmethane and triarylmethane-based compounds,

The photoinitiator relates to a colored photosensitive resin composition comprising an oxime ester compound.

The conventional colored photosensitive resin composition comprising at least one selected from the group consisting of triphenylmethane and triarylmethane-based compounds as a colorant has advantages of high colorability and color purity, but has a low reliability problem.

Therefore, in the present invention, in order to solve the above problems, it was intended to provide a colored photosensitive resin composition containing nano silica.

By including the nano silica, the penetration of the solvent into the coating film formed of the colored photosensitive resin composition is suppressed, and the colorant in the coating film is prevented from eluting, thereby improving the reliability of the colored photosensitive resin composition.

Hereinafter, the colored photosensitive resin composition of the present invention will be described in detail for each component.

(A) Colorant

In the present invention, the colorant includes at least one selected from the group consisting of triphenylmethane and triarylmethane-based compounds.

The triphenylmethane and triarylmethane-based compounds are specifically, for example,

C.I. Solvent Violet 8 and 9;

C.I. Solvent Blue 2, 3, 4, 5, 43 and 124;

C.I. Solvent Green 1;

C.I. Pigment Violet 3, 3:1, 3:3, 27 and 39;

C.I. Pigment Blue 1, 1:2, 9, 14, 24, 56, 56:1, 61, 61:1, 62 and 78 and

C.I. Pigment Green 1, 2, 4, 45, etc. are mentioned.

In addition, in order to improve reliability, including at least one selected from the group consisting of triphenylmethane and triarylmethane-based compounds integrated with an insolubilizing agent such as phosphotungstic acid or molybdic acid More preferably, specifically, for example, C.I. Pigment Blue 1, 9, 14, 62, C.I. Pigment violet 3 and 39, etc. are mentioned.

The colorant comprising at least one selected from the group consisting of triphenylmethane and triarylmethane-based compounds is included in an amount of 5 to 40% by weight based on the total weight of solids in the colored photosensitive resin composition of the present invention, preferably 10 to 30% by weight.

When the content of the colorant is less than 5% by weight, the increase in transmittance is insignificant, and when it exceeds 40% by weight, it is difficult to expect reliability improvement.

In the present invention, the solid content in the colored photosensitive resin composition means the total weight of the remaining components excluding the solvent of the colored photosensitive resin composition.

In addition, the colorant may further include one or more pigments.

(a1) pigment

As the pigment, organic or inorganic pigments generally used in the art may be used. In addition, the pigment may be subjected to resin treatment, surface treatment using a pigment derivative into which an acidic group or a basic group is introduced, graft treatment of the pigment surface with a high molecular compound, etc., atomization treatment by sulfuric acid atomization method, etc., as necessary to remove impurities A cleaning treatment with an organic solvent, water, or the like, or a treatment for removing ionic impurities by an ion exchange method or the like may be performed.

As the organic pigment, various pigments used in printing inks, inkjet inks, etc. may be used, and specifically, water-soluble azo pigments, insoluble azo pigments, phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, isoindoline pigments, Perylene pigment, perinone pigment, dioxazine pigment, anthraquinone pigment, dianthraquinonyl pigment, anthrapyrimidine pigment, ananthrone pigment, indanthrone pigment, pravanthrone pigment, pyranthrone pigment, diketopyrroropyrrole pigment and the like.

In addition, as the inorganic pigment, a metal compound such as a metal oxide or a metal complex salt can be used, and specifically, iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony, carbon black, organic and metal oxides or composite metal oxides, such as black pigments, titanium black, and pigments that are black by mixing red, green and blue.

In particular, the organic and inorganic pigments include compounds classified as pigments in the color index (published by The Society of Dyers and Colorists), and more specifically, the color index (C.I.) number of pigments, but are not necessarily limited thereto.

C.I. Pigment Yellow 13, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 180 and 185;

C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, and 71;

C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 208, 215, 216, 224, 242, 254, 255 and 264;

C.I. Pigment Violet 14, 19, 23, 29, 32, 33, 36, 37 and 38;

C.I. Pigment Blue 15 (15:3, 15:4, 15:6, etc.), 21, 28, 60, 64 and 76;

C.I. Pigment Green 7, 10, 15, 25, 36, 47 and 58;

C.I Pigment Brown 28; and

Pigments, such as C.I Pigment Black 1 and 7, are mentioned.

The pigment may be used alone or in combination of two or more.

As the pigment, it is preferable to use a pigment dispersion in which the particle diameter of the pigment is uniformly dispersed. Examples of the method for uniformly dispersing the particle size of the pigment include a method of dispersing and dispersing the pigment dispersant (a2). According to the method, a pigment dispersion in a state in which the pigment is uniformly dispersed in a solution can be obtained. there is.

(a2) Pigment dispersant

The pigment dispersant is added to deagglomerate and maintain the stability of the pigment, and specific examples of the pigment dispersant include cationic, anionic, nonionic, amphoteric, polyester, polyamine surfactants, etc. , These can be used individually or in combination of 2 or more types, respectively.

Specific examples of the cationic surfactant include amine salts or quaternary ammonium salts such as stearylamine hydrochloride and lauryl trimethylammonium chloride.

Specific examples of the anionic surfactant include higher alcohol sulfate salts such as sodium lauryl alcohol sulfate and sodium oleyl alcohol sulfate, alkyl sulfates such as sodium lauryl sulfate and ammonium lauryl sulfate, sodium dodecylbenzenesulfonate and Alkyl aryl sulfonates, such as sodium dodecyl naphthalene sulfonate, etc. are mentioned.

Specific examples of the nonionic surfactant include polyoxyethylene alkyl ether, polyoxyethylene aryl ether, polyoxyethylene alkyl aryl ether, other polyoxyethylene derivatives, oxyethylene/oxypropylene block copolymer, sorbitan fatty acid ester, Polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, glycerol fatty acid ester, polyoxyethylene fatty acid ester, polyoxyethylene alkylamine, etc. are mentioned.

In addition, polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyethylene glycol diesters, sorbitan fatty acid esters, fatty acid-modified polyesters, tertiary amine-modified polyurethanes, and polyethyleneimines are mentioned. there is.

In addition, the pigment dispersant preferably includes an acrylate-based dispersant (hereinafter, acrylate-based dispersant) including butyl methacrylate (BMA) or N,N-dimethylaminoethyl methacrylate (DMAEMA). Commercially available products of the acrylate-based dispersant include DISPER BYK-2000, DISPER BYK-2001, DISPER BYK-2070 or DISPER BYK-2150, and the acrylate-based dispersant may be used alone or in combination of two or more. can

As the pigment dispersant, other resin type pigment dispersants may be used in addition to the acrylate-based dispersant. As the pigment dispersant of the other resin type, a pigment dispersant of a known resin type, particularly polyurethane, polycarboxylic acid esters typified by polyacrylates, unsaturated polyamides, polycarboxylic acids, polycarboxylic acids (partially) amine salts, ammonium salts of polycarboxylic acids, alkylamine salts of polycarboxylic acids, polysiloxanes, long-chain polyaminoamide phosphate salts, esters of hydroxyl-containing polycarboxylic acids and modified products thereof, or free ) oily dispersants such as amides or salts thereof formed by the reaction of a polyester having a carboxyl group with poly(lower alkyleneimine); water-soluble resins or water-soluble polymer compounds such as (meth)acrylic acid-styrene copolymer, (meth)acrylic acid-(meth)acrylate ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol or polyvinyl pyrrolidone; Polyester; modified polyacrylates; adducts of ethylene oxide/propylene oxide; and phosphate esters.

As a commercial product of the above-mentioned other resin type pigment dispersant, as a cationic resin dispersant, for example, BYK (Big) Chemi Corporation's trade names: DISPER BYK-160, DISPER BYK-161, DISPER BYK-162, DISPER BYK-163, DISPER BYK-164, DISPER BYK-166, DISPER BYK-171, DISPER BYK-182, DISPER BYK-184; BASF brand names: EFKA-44, EFKA-46, EFKA-47, EFKA-48, EFKA-4010, EFKA-4050, EFKA-4055, EFKA-4020, EFKA-4015, EFKA-4060, EFKA-4300, EFKA- 4330, EFKA-4400, EFKA-4406, EFKA-4510, EFKA-4800; Trade names from Lubirzol: SOLSPERS-24000, SOLSPERS-32550, NBZ-4204/10; Trade names of Kawaken Fine Chemicals: HINOACT T-6000, HINOACT T-7000, HINOACT T-8000; Trade names of Ajinomoto Corporation: AJISPUR PB-821, AJISPUR PB-822, AJISPUR PB-823; Trade names of Kyoeisha Chemical Corporation: FLORENE DOPA-17HF, fluorene DOPA-15BHF, fluorene DOPA-33, fluorene DOPA-44, etc. are mentioned.

In addition to the acrylate-based dispersant, other resin-type pigment dispersants may be used alone or in combination of two or more, or may be used in combination with an acrylate-based dispersant.

The content of the pigment dispersant may be included in an amount of 5 to 60% by weight, specifically 15 to 50% by weight, based on the total weight of the solids in the colorant, and when the content of the pigment dispersant satisfies the above range, the viscosity increases, and , it is easy to atomize the pigment, and there is an advantage that can prevent problems such as gelation after dispersion.

(B) Alkali-soluble resin

The alkali-soluble resin of the present invention is preferably prepared by copolymerizing the ethylenically unsaturated monomer (b1) containing a carboxyl group as an essential component in order to have solubility in the alkali developer used in the developing treatment step when forming the pattern. .

Specific examples of the ethylenically unsaturated monomer (b1) containing a carboxyl group include monocarboxylic acids such as acrylic acid, methacrylic acid, and crotonic acid; dicarboxylic acids such as fumaric acid, mesaconic acid, and itaconic acid; anhydrides of dicarboxylic acids; Polymer mono(meth)acrylates containing a carboxyl group and a hydroxyl group at both terminals, such as ω-carboxypolycaprolactone mono(meth)acrylate; etc. are mentioned, and acrylic acid and methacrylic acid are preferable.

In addition, in the preparation of the alkali-soluble resin, an alkali-soluble resin may be prepared by polymerizing an ethylenically unsaturated monomer including the carboxyl group and an unsaturated monomer copolymerizable with the ethylenically unsaturated monomer.

The type of the unsaturated monomer is not particularly limited, but specifically, for example,

2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate and N -ethylenically unsaturated monomers containing a hydroxyl group, such as hydroxyethyl acrylamide;

Styrene, vinyltoluene, α-methylstyrene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, o-vinylbenzylmethyl ether, m-vinylbenzylmethyl ether, p-vinyl aromatic vinyl compounds such as 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, N-o-hydroxyphenylmaleimide, N-m-hydroxyphenylmaleimide, N-p-hydroxyphenylmaleimide, N-o-methylphenylmaleimide, N-m -N-substituted maleimide compounds such as methylphenylmaleimide, N-p-methylphenylmaleimide, N-o-methoxyphenylmaleimide, N-m-methoxyphenylmaleimide and N-p-methoxyphenylmaleimide;

Methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, i-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; Cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, tricyclo [5.2.1.0 2,6 ] decan-8-yl (meth) acrylate, 2- 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)oxetane, 3-(methacryloyloxymethyl)-3-ethyloxetane, 3-(methacryloyloxymethyl)-2-trifluoromethyloxetane; 3-(methacryloyloxymethyl)-2-phenyloxetane, 2-(methacryloyloxymethyl)oxetane and 2-(methacryloyloxymethyl)-4-trifluoromethyloxetane, etc. of unsaturated oxetane compounds.

The unsaturated monomers may be used alone or in combination of two or more.

In addition, the alkali-soluble resin preferably has an acid value of 30 to 150 mgKOH/g, preferably 50 to 120 in order to secure developability.

When the acid value of the alkali-soluble resin is less than 30 mgKOH/g, it is difficult to secure a sufficient development rate of the colored photosensitive resin composition, and when it exceeds 150 mgKOH/g, the adhesion between the colored photosensitive resin composition and the substrate decreases, resulting in a short circuit of the pattern This is easy to happen.

The alkali-soluble resin is included in an amount of 10 to 80% by weight, preferably 10 to 70% by weight, based on the total weight of the colored photosensitive resin composition.

When the content of the alkali-soluble resin is 10 to 80 wt%, the solubility in the developer is sufficient, so that the pattern can be easily formed. .

(C) photopolymerization compound

The photopolymerizable compound as one of the colored photosensitive resin compositions of the present invention must be a compound capable of polymerization by the action of a photoinitiator (D) to be described later.

As the photopolymerizable compound, a monofunctional monomer, a bifunctional monomer, or a polyfunctional monomer may be used, and a bifunctional monomer is preferably used, but is not limited thereto.

Specific examples of the monofunctional monomer include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate, or N-vinylpi Rollidone, and the like, but is not limited thereto.

Specific examples of the bifunctional monomer include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, and triethylene glycol di (meth) acrylate. , bis(acryloyloxyethyl)ether of bisphenol A, or 3-methylpentanediol di(meth)acrylate, but is not limited thereto.

Specific examples of the polyfunctional monomer include trimethylolpropane tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, propoxylated trimethylolpropane tri(meth)acrylate, and pentaerythritol. Tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, ethoxylated dipentaerythritol hexa (meth) acrylate, propoxylated dipentaeryth Ritol hexa (meth) acrylate or dipentaerythritol hexa (meth) acrylate, but is not limited thereto.

The photopolymerizable compound is included in an amount of 5 to 45 wt%, preferably 7 to 45 wt%, based on the total weight of the colored photosensitive resin composition of the present invention. The photopolymerizable compound may improve the strength and reliability of the pixel portion in the range of 5 to 45 wt%.

(D) light curing initiator

The photoinitiator which is one of the coloring photosensitive resin compositions of this invention is a compound which can polymerize the above-mentioned photopolymerizable compound (C).

In the present invention, the photopolymerization initiator essentially includes an oxime ester compound. The sensitivity of the coloring photosensitive resin composition can be improved by including the said oxime ester type compound.

Specifically, as the oxime ester compound, for example, 1,2-octadione (1,2-Octanedione), 1- [4- (phenylthio) phenyl] -, 2- (O-benzoyloxime) ( 1-[4-(phenylthio)phenyl]-,2-(O-benzoyloxime)) and 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone 1- (O-acetyloxime) (1-[9-Ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone 1-(O-acetyloxime)), etc., are commercially available oxime ester compounds. BASF's Irgacure® OXE 01, Irgacure® OXE 02, and Irgacure® OXE 03 are available.

In addition, the photoinitiator may further include other types of photoinitiators in addition to the oxime ester-based compound. Typically, it is preferable to further include at least one compound selected from the group consisting of an acetophenone-based compound, a benzophenone-based compound, a triazine-based compound, a biimidazole-based compound, and a thioxanthone-based compound.

Specifically, the acetophenone-based compound is, for example, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethyl ketal, 2-hydroxy-1-[4-( 2-hydroxyethoxy)phenyl]-2-methylpropan-1-one, 1-hydroxycyclohexylphenylketone, 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropane-1 -one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one, 2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl] propan-1-one and 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4-morpholinophenyl)butan-1-one; and the like.

The benzophenone-based compound is specifically, for example, benzophenone, 0-benzoylbenzoate methyl, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3',4,4'- and tetra(tert-butylperoxycarbonyl)benzophenone and 2,4,6-trimethylbenzophenone.

The triazine-based compound is specifically, for example, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl) )-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2, 4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran) -2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5 -triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine and 2,4-bis( trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine;

The biimidazole compound is specifically, for example, 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',5,5'-tetra(alkoxyphenyl) Biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole, 2,2-bis(2,6-dichlorophenyl) -4,4',5,5'-tetraphenyl-1,2'-biimidazole and imidazole compounds in which the phenyl group at the 4,4',5,5' position is substituted with a carboalkoxy group; can Among them, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4' ,5,5'-tetraphenylbiimidazole and 2,2-bis(2,6-dichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole are preferably used

The thioxanthone-based compound is specifically, for example, 2-isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythiok. Santon etc. are mentioned.

In addition, the photopolymerization initiator may further include a photopolymerization initiation auxiliary (d1) in order to improve the sensitivity of the colored photosensitive resin composition of the present invention. When the colored photosensitive resin composition according to the present invention contains the photopolymerization initiation auxiliary (d1), the sensitivity further increases and productivity can be improved.

The photopolymerization initiation adjuvant, for example, may preferably be used at least one compound selected from the group consisting of an amine compound, a carboxylic acid compound, an organic sulfur compound having a thiol group.

It is preferable to use an aromatic amine compound as the amine compound, and specifically, for example, an aliphatic amine compound such as triethanolamine, methyldiethanolamine and triisopropanolamine; 4-dimethylaminobenzoic acid methyl, 4-dimethylaminobenzoic acid ethyl, 4-dimethylaminobenzoic acid isoamyl, 4-dimethylaminobenzoic acid 2-ethylhexyl, benzoic acid 2-dimethylaminoethyl, N,N-dimethylparatoluidine, 4, 4'-bis(dimethylamino)benzophenone (common name: Michler's ketone) and 4,4'-bis(diethylamino)benzophenone, etc. can be used.

The carboxylic acid compound is preferably aromatic heteroacetic acid, specifically, for example, phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenyl and thioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

The organic sulfur compound having the thiol group is specifically, for example, 2-mercaptobenzothiazole, 1,4-bis(3-mercaptobutyryloxy)butane, 1,3,5-tris(3-mercaptobutyl) Oxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, trimethylolpropanetris(3-mercaptopropionate), pentaerythritoltetrakis(3 -mercaptobutylate), pentaerythritol tetrakis (3-mercaptopropionate), dipentaerythritol hexakis (3-mercaptopropionate) and tetraethylene glycol bis (3-mercaptopropionate) ) and the like.

The photopolymerization initiator may be included in an amount of 0.1 to 20% by weight, preferably 1 to 15% by weight, based on the total weight of the solid content in the colored photosensitive resin composition of the present invention.

When the photopolymerization initiator is included in an amount of 0.1 to 40% by weight, the colored photosensitive resin composition is highly sensitive, and the exposure time is shortened, thereby improving productivity and maintaining high resolution. In addition, the intensity of the pixel portion and smoothness on the surface of the pixel portion may be improved.

In addition. The photopolymerization initiation adjuvant is included in an amount of 10 to 100 wt%, preferably 20 to 100 wt%, based on the total weight of the photopolymerization initiator.

When the photopolymerization initiation auxiliary agent is included in an amount of less than 10% by weight, the decrease in sensitivity due to the dye cannot be overcome, and a short circuit of the pattern tends to occur during the development process.

(E) Solvent

As long as the solvent is effective in dissolving other components included in the colored photosensitive resin composition, the solvent used in the conventional colored photosensitive resin composition may be used without particular limitation, and in particular, ethers, acetates, aromatic hydrocarbons, ketones, Alcohols, esters or amides are preferable.

Examples of the ethers include 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 dialkyl ethers, such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, and diethylene glycol dibutyl ether, etc. are mentioned.

The acetates include, for example, methyl cellosolve acetate, ethyl cellosolve acetate, ethyl acetate, butyl acetate, amyl acetate, methyl lactate, ethyl lactate, butyl lactate, 3-methoxybutyl acetate, 3 -Methyl-3-methoxy-1-butyl acetate, methoxypentyl acetate, ethylene glycol monoacetate, ethylene glycol diacetate, methyl 3-methoxypropionate, propylene glycol methyl ether acetate, 3-methoxy-1- Butyl acetate, 1,2-propylene glycol diacetate, ethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, dipropylene glycol methyl ether acetate, 1,3-butylene glycol diacetate, diethylene glycol monobutyl ether Acetate, 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, etc. are mentioned.

Examples of the aromatic hydrocarbons include benzene, toluene, xylene, and mesitylene.

Examples of the ketones include methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone and cyclohexanone.

Examples of the alcohols include ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, glycerin, and 4-hydroxy-4-methyl-2-pentanone.

Examples of the esters include ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, and γ-butyrolactone.

Examples of the amides include dimethylformamide (DMF) and N-methyl-2-pyrilidone (NMP).

Each of the solvents may be used alone or in combination of two or more.

The solvent is preferably an organic solvent having a boiling point of 100°C to 200°C in terms of applicability and dryness, for example, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, ethylac Tate, butyl lactate, 3-ethoxy ethyl propionate, 3-methoxy methyl propionate, etc. are mentioned.

The solvent is included in an amount of 60 to 90% by weight, preferably 70 to 85% by weight, based on the total weight of the colored photosensitive resin composition. When the solvent is included in the range of 60 to 90% by weight, the coating property is good when applied with a roll coater, a spin coater, a slit and spin coater, a slit coater (sometimes referred to as a die coater), and an inkjet coating device. can be done

(F) Nano silica

The colored photosensitive resin composition of the present invention suppresses penetration of a solvent into the coating film formed of the colored photosensitive resin composition by including nano silica, and can prevent the colorant from eluting in the coating film. That is, it is possible to provide a colored photosensitive resin composition having excellent reliability through this.

The structure of the nano-silica is a structure in which fine particles containing 20 to 50 SiO ₂ have a colloidal form.

In addition, the diameter of the nano-silica is 5 to 100 nm, preferably 20 to 50 nm. When the diameter of the nano-silica is less than 5 nm, the effect due to the addition of the nano-silica is insignificant, and when it exceeds 100 nm, a decrease in transmittance and a decrease in the contrast ratio may occur due to the nano-silica.

The nano-silica is included in an amount of 1 wt% or more and less than 10 wt%, preferably 2 to 7 wt%, based on the total weight of the solid content in the colored photosensitive resin composition of the present invention.

If the content of the nano-silica is less than 1% by weight, it cannot effectively suppress the penetration of the solvent into the coating film formed of the colored photosensitive resin composition. easy.

It is preferable to use the nano silica dispersed in the solvent of the colored photosensitive resin composition, and representatively, ORGANOSILICASOL of NISSAN CHEMICAL and NANOPOL of Evonik may be used.

(G) Additives

The additive may be selectively added as needed, and may include, for example, at least one selected from the group consisting of fillers, other high molecular compounds, curing agents, surfactants, adhesion promoters, ultraviolet absorbers, and anti-aggregation agents. .

Glass or alumina may be used as the filler, but the type is not limited thereto.

Specific examples of the other high molecular compounds include curable resins such as epoxy resins and maleimide resins, thermoplastic resins such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl acrylate, polyester, and polyurethane. can be heard

The curing agent is used to enhance deep curing and mechanical strength, and specific examples of the curing agent include an epoxy compound, a polyfunctional isocyanate compound, a melamine compound, and an oxetane compound.

Specific examples of the epoxy compound in the curing agent include bisphenol A epoxy resin, hydrogenated bisphenol A epoxy resin, bisphenol F epoxy resin, hydrogenated bisphenol F epoxy resin, novolak epoxy resin, other aromatic epoxy resins, alicyclic epoxy resins , glycidyl ester-based resins, glycidylamine-based resins, or brominated derivatives of the above epoxy resins, aliphatic, alicyclic or aromatic epoxy compounds other than epoxy resins and brominated derivatives thereof, butadiene (co)polymer epoxides, isoprene ( A co)polymer epoxidized product, a glycidyl (meth)acrylate (co)polymer, triglycidyl isocyanurate, etc. are mentioned.

Specific examples of the oxetane compound in the curing agent include carbonate bisoxetane, xylenebisoxetane, adipate bisoxetane, terephthalate bisoxetane, and cyclohexanedicarboxylic acid bisoxetane.

The curing agent may be used 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 together with the curing agent.

The curing auxiliary compound includes, for example, polyhydric carboxylic acids, polyhydric carboxylic acid anhydrides, and acid generators. As the polyhydric carboxylic acid anhydrides, commercially available epoxy resin curing agents may be used. Examples of the commercially available products include ADEKAHADONA EH-700 (manufactured by Adeka Industrial Co., Ltd.), Rikashiddo HH (manufactured by New Nippon Ewha Co., Ltd.), and MH-700 (manufactured by Nippon Ewha Co., Ltd.). The curing agents exemplified above may be used alone or in combination of two or more.

The surfactant may be used to further improve the film formation of the colored photosensitive resin composition, and silicone-based, fluorine-based, ester-based, cationic, anionic, nonionic, amphoteric, and the like surfactants may be preferably used.

The silicone-based surfactants include, for example, DC3PA, DC7PA, SH11PA, SH21PA and SH8400 of Dow Corning Toray Silicone Co. -4460 and TSF-4452.

The fluorine-based surfactant includes, for example, Megapiece F-470, F-471, F-475, F-482 and F-489 manufactured by Dainippon Ink Chemical Co., Ltd. as a commercially available product.

In addition, other commercially available products include KP (Shin-Etsu Chemical Co., Ltd.), POLYFLOW (Kyoeisha Chemical Co., Ltd.), EFTOP (Tochem Products), and MEGAFAC. (Dainippon Ink Chemical High School Co., Ltd.), Florad (Sumitomo 3M Co., Ltd.), Asahi guard, Surflon (above, Asahi Glass Co., Ltd.), SOLSPERSE (Lubrisol) , EFKA (EFKA Chemicals), PB 821 (Ajinomoto), Disperbyk-series (BYK-chemi), and the like.

Each of the surfactants exemplified above may be used alone or in combination of two or more.

The type of the adhesion promoter is not particularly limited, and specific examples of the adhesion promoter that can be used include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, N-(2-aminoethyl). )-3-Aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3 -Glycidoxypropylmethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxy propyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanatepropyltrimethoxysilane, 3-isocyanatepropyltriethoxysilane, etc. are mentioned.

The adhesion promoters illustrated above can be used individually or in combination of 2 or more types, respectively. The adhesion promoter may be included in an amount of 0.01 to 10% by weight, preferably 0.05 to 2% by weight, based on the total weight of the solid content in the colored photosensitive resin composition.

The type of the ultraviolet absorber is not particularly limited, but specific examples that can be used include 2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chlorobenzothiazole, alkoxybenzophenone, and the like. .

The type of the aggregation inhibitor is not particularly limited, and specific examples that can be used include sodium polyacrylate.

The manufacturing method of the coloring photosensitive resin composition of this invention is as follows.

First, the colorant (A) is mixed with the solvent (E) and dispersed using a bead mill or the like until the average particle diameter of the pigment is about 0.2 µm or less. At this time, if necessary, a part or all of the pigment dispersant (a2) and alkali-soluble resin (B) may be mixed with the solvent (E) to be dissolved or dispersed.

The remainder of the alkali-soluble resin (B), photopolymerizable compound (C), photoinitiator (D), nano silica (F) and, if necessary, additives (G) and solvent (E) are added to the mixed colorant at a predetermined concentration It can be further added to prepare a colored photosensitive resin composition according to the present invention.

In addition, the present invention provides a color filter made of a colored photosensitive resin composition and a display device having the same.

First, the colored photosensitive resin composition is applied on a substrate (usually glass) or a layer made of the solid content of the previously formed colored photosensitive resin composition, and then volatile components such as a solvent are removed by heating and drying to obtain a smooth coating film.

As a coating method, it can carry out by the spin coating method, the casting|flow_spread coating method, the roll coating method, the slit-and-spin coating method, or the slit coating method, etc., for example. Heat-drying after application|coating (pre-baking), or heating after drying under reduced pressure to volatilize volatile components, such as a solvent. Here, the heating temperature is usually 70 to 200°C, preferably 80 to 130°C. The thickness of the coating film after heat drying is usually about 1 to 8 µm. In this way, an ultraviolet-ray is irradiated through the mask for forming the target pattern on the obtained coating film. At this time, it is preferable to use a device such as a mask aligner or a stepper so that parallel rays are uniformly irradiated to the entire exposed portion and the mask and the substrate are precisely aligned. When irradiated with ultraviolet rays, the portion irradiated with ultraviolet rays is cured.

As the ultraviolet rays, g-line (wavelength: 436 nm), h-line, i-line (wavelength: 365 nm), etc. may be used. The irradiation amount of ultraviolet rays may be appropriately selected according to necessity, and the present invention is not limited thereto. When the cured coating film is brought into contact with a developer to dissolve the unexposed portion and developed, a spacer having a desired pattern shape can be obtained.

The developing method is not particularly limited to a liquid addition method, a dipping method, a spray method, or the like. In addition, you may incline a board|substrate at an arbitrary angle at the time of development. The developer is usually an aqueous solution containing an alkaline compound and a surfactant.

The alkaline compound is not particularly limited to an inorganic or organic alkaline compound. Examples of the inorganic alkaline compound include sodium hydroxide, potassium hydroxide, disodium hydrogen phosphate, sodium dihydrogen phosphate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate, potassium dihydrogen phosphate, sodium silicate, potassium silicate, sodium carbonate, Potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium borate, potassium borate, ammonia, etc. are mentioned.

Further, as the organic alkaline compound, for example, tetramethylammonium hydroxide, 2-hydroxyethyltrimethylammonium hydroxide, monomethylamine, dimethylamine, trimethylamine, monoethylamine, diethylamine, triethylamine , monoisopropylamine, diisopropylamine, ethanolamine, and the like.

Each of the inorganic or organic alkaline compounds may be used alone or in combination of two or more. The concentration of the alkaline compound in the developer is 0.01 to 10% by weight, preferably 0.03 to 5% by weight, based on the total weight of the developer.

The surfactant in the developer may be at least one selected from the group consisting of the aforementioned nonionic surfactants, anionic surfactants and cationic surfactants. The concentration of the surfactant in the developer is 0.01 to 10% by weight, preferably 0.05 to 8% by weight, more preferably 0.1 to 5% by weight based on the total weight of the developer. After development, it may be washed with water and, if necessary, may be post-baked at 150 to 230°C for 10 to 60 minutes.

A specific pattern can be formed on a board|substrate through each process as mentioned above using the coloring photosensitive resin composition of this invention.

Hereinafter, in order to describe the present invention in detail, examples will be described in detail. However, the embodiments according to the present invention may be modified in various other forms, and the scope of the present invention should not be construed as being limited to the embodiments described in detail below. The embodiments of the present invention are provided to more completely explain the present invention to those of ordinary skill in the art.

Synthesis example 1. Synthesis of alkali-soluble resin

120 parts by weight of propylene glycol monomethyl ether acetate, 80 parts by weight of propylene glycol monomethyl ether, 2 parts by weight of AIBN, 13 parts by weight of acrylic acid, benzyl meta into a 1000 mL flask equipped with a stirrer, thermometer reflux cooling tube, dropping funnel and nitrogen inlet tube. 10 parts by weight of acrylate, 57 parts by weight of 4-methylstyrene, 20 parts by weight of methyl methacrylate, and 3 parts by weight of n-dodecyl mercapto were added and nitrogen substituted. Thereafter, the temperature of the reaction solution was raised to 110° C. with stirring, and the reaction was carried out for 6 hours after the rise.

The alkali-soluble resin thus prepared had a solid content acid value of 100.2 mgKOH/g, and a weight average molecular weight Mw measured by GPC was about 15110.

<Preparation of pigment dispersion composition>

production example One.

As a colorant, C.I. 12 parts by weight of Pigment Blue 1, 6 parts by weight of LPN-6919 (manufactured by BYK) as a pigment dispersant, and 82 parts by weight of propylene glycol monomethyl ether acetate as a solvent were mixed, and the pigment was mixed and dispersed for 12 hours using a bead mill. A dispersion composition M1 was prepared.

production example 2.

As a colorant, C.I. Pigment Blue 15:6 12 parts by weight, LPN-6919 (manufactured by BYK) 6 parts by weight as a pigment dispersant, and 82 parts by weight of propylene glycol monomethyl ether acetate as a solvent are mixed, and mixed and dispersed for 12 hours using a bead mill to prepare a pigment dispersion composition M2.

<Production of colored photosensitive resin composition>

Example 1 to 4 and comparative example 1 to 4.

Colored photosensitive resin compositions of Examples 1 to 4 and Comparative Examples 1 to 4 were prepared with the composition shown in Table 1 below.

(Unit: % by weight) division Example comparative example One 2 3 4 One 2 3 4 pigment dispersion
composition M1 25 12.5 25 12.5 25 12.5 25 12.5 M2 - 12.5 - 12.5 - 12.5 - 12.5 alkali soluble
profit 13.36 13.36 13.14 13.14 13.36 13.36 13.36 13.36 photopolymerizable compound 4.45 4.45 4.38 4.38 4.45 4.45 4.45 4.45 light curing
initiator D1 1.34 1.34 1.31 1.31 1.34 1.34 - - D2 - - - - - - 1.34 1.34 solvent E1 17 17 17 17 17 17 17 17 E2 38.58 38.58 38.73 38.73 38.58 38.58 38.58 38.58 nano silica F1 0.27 0.27 - - - - 0.27 0.27 F2 - - 0.44 0.44 - - - -

pigment dispersion composition

M1: Pigment dispersion composition prepared in Preparation Example 1

M2: Pigment dispersion composition prepared in Preparation Example 2

Alkali-soluble resin: alkali-soluble resin prepared in Synthesis Example 1

Photopolymerizable compound: KAYARAD DPHA (Nippon Kayaku)

photopolymerization initiator

D1: PBG-327 (manufactured by Tronley)

D2: Irgacure 369 (manufactured by BASF)

solvent

E1: diacetone alcohol

E2: propylene glycol monomethyl ether acetate

Nano Silica

F1 : Nanopol C764 (Evonik)

F2 : MEK-AC-2140Z (Organosilicasol)

Experimental example 1. Color filter manufacturing and physical properties measurement

Each of the colored photosensitive resin compositions of Examples 1 to 4 and Comparative Examples 1 to 4 was coated on a 2-inch glass substrate (“EAGLE XG, manufactured by Corning) by spin coating,” and then placed on a heating plate at a temperature of 100° C. for 3 minutes. was maintained to form a thin film.

Thereafter, a test photomask having a line/space pattern of 1 to 100 µm was placed on the thin film, and ultraviolet rays were irradiated with an interval of 300 µm from the test photomask. At this time, ultraviolet rays were irradiated with an illuminance of 50 mJ/cm 2 using a high-pressure mercury lamp of 1 kW containing all of the g, h and i rays, and no special optical filter was used.

The thin film irradiated with ultraviolet light was developed by immersing it in a developing solution of a KOH aqueous solution having a pH of 10.5 for 2 minutes. 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 230° C. for 25 minutes to prepare a color filter.

1-1. Adhesion measurement

The pattern generated on the color filter prepared above was observed using an optical microscope to evaluate the degree of pattern tearing.

The evaluation criteria are as follows, and the results are shown in Table 2 below.

<Evaluation criteria>

○: No tearing in pattern

△: 1 to 4 torn patterns

×: 5 or more torn in the pattern

1-2. transmittance measurement

When the color filter was manufactured by the above method, except that a test photomask was not used, a color filter was prepared in the same manner and transmittance was measured using a colorimeter (manufactured by Olympus, OSP-200), and the results are shown in Table 2 below. shown in

1-3. solvent resistance Measure

A color filter was manufactured in the same manner except that a test photomask was not used when manufacturing the color filter by the above method.

The color coordinates of the color filter were measured with a colorimeter (manufactured by Olympus, OSP-200), and the substrate on which the color coordinates were measured was immersed in N-methylpyrrolidone at 90° C. for 2 minutes.

After taking out the substrate, it was washed with distilled water to measure chromaticity again, and the color difference before and after immersion in N-methylpyrrolidone was calculated as ΔE*ab of Equation 1 below.

The evaluation criteria are as follows, and the results are shown in Table 2 below.

[Equation 1]

Color coordinates before immersion in L*, a* and b* coordinate systems = (L ₁ *, a ₁ *, b ₁ *)

Color coordinates after immersion in L*, a* and b* coordinate systems = (L ₂ *, a ₂ *, b ₂ *)

<Evaluation criteria>

○ : ΔE*ab 5.0 or less

△: ΔE*ab greater than 5.0 and less than or equal to 10.0

X: ΔE*ab greater than 10.0

composition transmittance solvent resistance adhesion Example 1 10.67 ○ ○ Example 2 10.34 ○ ○ Example 3 10.65 ○ ○ Example 4 10.31 ○ ○ Comparative Example 1 10.68 Ⅹ △ Comparative Example 2 10.35 △ ○ Comparative Example 3 10.62 Ⅹ Ⅹ Comparative Example 4 10.32 △ Ⅹ

From the results of Table 2, the colored photosensitive resin composition of the present invention showed excellent results in transmittance, solvent resistance, and adhesion.

On the other hand, the colored photosensitive resin compositions of Comparative Examples 1 and 2 that did not contain nanosilica did not show excellent solvent resistance, and the colored photosensitive resin compositions of Comparative Examples 3 and 4 that did not contain an oxime ester-based compound as a photopolymerization initiator Silver did not show excellent results in both solvent resistance and adhesion.

Therefore, it was confirmed through experiments that the colored photosensitive resin composition of the present invention including nano silica and an oxime ester-based compound as a photopolymerization initiator has excellent solvent resistance and adhesion, and thus excellent reliability.

Claims (8)

A colored photosensitive resin composition comprising a colorant, an alkali-soluble resin, a photopolymerizable compound, a photoinitiator, a solvent, and nano silica,
The colorant includes at least one selected from the group consisting of triphenylmethane and triarylmethane-based compounds,
The photopolymerization initiator includes an oxime ester-based compound,
The colored photosensitive resin composition, characterized in that the nano-silica has a diameter of 5 to 100 nm. The method according to claim 1, wherein the triphenylmethane and triarylmethane-based compound is
CI Solvent Violet 8 and 9;
CI Solvent Blue 2, 3, 4, 5, 43 and 124;
CI Solvent Green 1;
CI Pigment Violet 3, 3:1, 3:3, 27 and 39;
CI Pigment Blue 1, 1:2, 9, 14, 24, 56, 56:1, 61, 61:1, 62 and 78; and
A colored photosensitive resin composition comprising at least one selected from the group consisting of CI Pigment Green 1, 2, 4 and 45. The colored photosensitive resin composition according to claim 1, wherein the colorant further comprises a pigment. The method according to claim 1, wherein the oxime ester compound is 1,2-octadione, 1-[4-(phenylthio)phenyl]-,2-(O-benzoyloxime) and 1-[9-ethyl-6- (2-methylbenzoyl)-9H-carbazol-3-yl]ethanone A colored photosensitive resin composition comprising at least one selected from the group consisting of 1-(O-acetyloxime). delete The method according to claim 1, 5 to 40% by weight of the colorant, 10 to 80% by weight of the alkali-soluble resin, 5 to 45% by weight of the photopolymerizable compound, 0.1 to 20% by weight of the photopolymerization initiator based on the total weight of the solid content in the colored photosensitive resin composition, and nano silica 1 or more and less than 10% by weight, the colored photosensitive resin composition comprising 60 to 90% by weight of a solvent based on the total weight of the colored photosensitive resin composition. A color filter made of the colored photosensitive resin composition of claim 1. A display device including the color filter of claim 7.