KR101992866B1 - Colored photosensitive resin composition - Google Patents

Abstract

The present invention relates to a colored photosensitive resin composition, and more particularly, to a colored photosensitive resin composition comprising a red colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator and a solvent; The red colorant comprises a red pigment and a xanthene dye represented by formula (1); The photopolymerization initiator comprises a compound represented by the general formula (2); Since the solvent contains propylene glycol monomethyl ether acetate and 4-hydroxy-4-methyl-2-pentanone, the developing speed is fast and the sensitivity and adhesion are excellent, so that peeling of the pattern can be suppressed during the developing process, And storage stability, so that foreign matter generation and viscosity change can be suppressed, and a color filter excellent in transmittance and contrast ratio can be produced.

Description

COLORED PHOTOSENSITIVE RESIN COMPOSITION [0002]

The present invention relates to a colored photosensitive resin composition.

BACKGROUND ART [0002] Color filters are widely used in imaging devices, liquid crystal display devices, and the like, and their application range is rapidly expanding. A color filter used for a color liquid crystal display device, an image pickup device, or the like is a device for uniformly applying a colored photosensitive resin composition containing a coloring agent corresponding to each color of red, green and blue on a substrate on which a black matrix is pattern- The coating film formed by heating and drying (hereinafter also referred to as preliminary firing) may be exposed and developed, and if necessary, further heat curing (hereinafter also referred to as post-firing) may be repeated for each color, Color pixels are formed.

As the coloring agent in the colored photosensitive resin composition, a pigment dispersion system is generally used. For this purpose, a pigment dispersion method is used. As the pigment dispersion method, there is a method of producing a color filter by photolithography using a coloring and radiation-sensitive composition in which pigments are dispersed in various photosensitive compositions. This method has been widely used as a preferable method for producing a color filter for a large-screen and high-resolution color display because it can secure sufficient reliability against light or heat since a pigment is used.

However, in recent years, the size of display has been rapidly increasing, and high contrast ratio has been continuously demanded. However, in the conventional pigment dispersing system, the limit of pigment particleization has reached a limit and due to problems such as color unevenness due to coarse particles, A method of simultaneously using a pigment and a dye has been studied (Korean Patent No. 10-0881860).

However, when a color filter is produced by using a colored photosensitive resin composition containing a dye as a coloring agent, the light resistance and heat resistance of the dye are poor, so that color shifts occur frequently, and the development speed is slow and sensitivity is low. There is a problem that the formed pattern is peeled off during the process.

Therefore, research has been conducted to solve this problem. For example, Korean Patent Laid-Open Publication No. 2011-0085005 discloses a ketooxime ester-based photoinitiator having good thermal stability and a method for producing the same, in order to solve the problem of poor OXE-1 ketooxime ester photoinitiator having poor application performance and low thermal stability. / RTI >

Korean Unexamined Patent Publication (Kokai) No. 2010-0088529 discloses an acrylate monomer having a hydroxyl value of not less than 70 mgKOH / g and not more than 130 mgKOH / g, which is inadequate to satisfy the adhesion, resolution, Or less, and a photosensitive resin composition for a black matrix are disclosed.

However, it is still necessary to solve the problem of the developing speed and sensitivity, and the problem of delamination of the pattern in the development process by the alkali developing solution.

Korean Patent Laid-Open Publication No. 2012-112188 discloses a red coloring composition and a color filter for a color filter, but fails to provide an alternative to the above problem.

Korean Patent No. 10-0881860 Korea Patent Publication No. 2011-0085005 Korea Patent Publication No. 2010-0088529

It is an object of the present invention to provide a colored photosensitive resin composition which can obtain a color filter excellent in contrast ratio and transmittance.

An object of the present invention is to provide a colored photosensitive resin composition which is excellent in storage stability and does not have a low sensitivity or an increased viscosity even when stored for a long time.

An object of the present invention is to provide a colored photosensitive resin composition which has a high developing speed and is excellent in sensitivity and adhesion so that no pattern peeling occurs during the development process.

1. A lithographic printing plate comprising: a red colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent; Wherein the red colorant comprises a red pigment and a xanthene dye represented by Formula 1 below; Wherein the alkali-soluble resin has an acid value of 30 to 170 mg KOH / g; Wherein the photopolymerization initiator comprises a compound represented by the following formula (2); Wherein the solvent comprises propylene glycol monomethyl ether acetate and 4-hydroxy-4-methyl-2-pentanone.

[Chemical Formula 1]

(Wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ are independently of each other a hydrogen atom or an alkyl group having 1 to 5 carbon atoms; R ₇ and R ₈ are each independently a hydrogen atom, -COOH ^{_{, -COO -, -SO 3 -,}} -SO 3 H, -SO 3 Na, -COOCH 3 or -COOCH ₂ CH ₃ Im)

(2)

이고; R₂ 및 R₃는 서로 독립적으로 히드록시기 또는 탄소수 1 내지 8의 알킬기로 치환 또는 비치환된 탄소수 1 내지 8의 알킬기, 페닐기, 벤질기 또는 디페닐설파이드기이며; R₄는 탄소수 1 내지 4의 알킬렌기이고; R₅는 탄소수 3 내지 8의 시클로알킬기임).(Wherein R < _{1 >} is

ego; R ₂ and R ₃ independently represent an alkyl group having 1 to 8 carbon atoms, a phenyl group, a benzyl group or a diphenylsulfide group which is substituted or unsubstituted with a hydroxy group or an alkyl group having 1 to 8 carbon atoms; R ₄ is an alkylene group having 1 to 4 carbon atoms; And R < ₅ > is a cycloalkyl group having 3 to 8 carbon atoms.

2. The xanthan dyestuff according to 1 above, wherein the xanthene dye is at least one selected from the group consisting of Acid Red 52, Basic Red 1, Basic Violet 10, Basic Violet 11, Rhodamine B, Rhodamine 6G, Rhodamine 123 and Sulfolodamine B 1 < / RTI >

3. The photosensitive resin composition according to item 1, further comprising at least one photopolymerization initiator selected from the group consisting of an acetophenone-based compound, a benzophenone-based compound, a triazine-based compound, a biimidazole compound and a thioxanthone- Colored photosensitive resin composition.

4. The colored photosensitive resin composition according to 1 above, wherein the propylene glycol monomethyl ether acetate and 4-hydroxy-4-methyl-2-pentanone are mixed at a ratio of 90:10 to 60:40.

5. The colored photosensitive resin composition according to item 1, further comprising at least one photopolymerization initiation auxiliary selected from the group consisting of an amine compound, a carboxylic acid compound and an organic sulfur compound having a thiol group.

6. The photosensitive resin composition according to 1 above, wherein the amount of the red coloring agent is 5 to 60 wt%, the amount of the alkali-soluble resin is 10 to 80 wt%, and the amount of the photopolymerizable compound is 5 to 45 wt% Being; The photopolymerization initiator is contained in an amount of 0.1 to 40% by weight based on the total amount of the alkali-soluble resin and the photopolymerizable compound based on the solid content; Wherein the solvent comprises 60 to 90% by weight of the total weight of the colored photosensitive resin composition.

7. A color filter made of a colored photosensitive resin composition according to any one of the above 1 to 6.

8. A liquid crystal display device comprising the color filter of 7 above.

The present invention has a high developing speed and is excellent in sensitivity and adhesion so that peeling of the pattern can be suppressed during the developing process.

The colored photosensitive resin composition of the present invention is excellent in dispersibility and storage stability, and can suppress foreign matter generation and viscosity change.

The color filter made of the colored photosensitive resin composition of the present invention has excellent contrast and transmittance.

The present invention includes a red colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent; The red colorant comprises a red pigment and a xanthene dye represented by formula (1); The photopolymerization initiator comprises a compound represented by the general formula (2); Since the solvent contains propylene glycol monomethyl ether acetate and 4-hydroxy-4-methyl-2-pentanone, the developing speed is fast and the sensitivity and adhesion are excellent, so that peeling of the pattern can be suppressed during the developing process, And storage stability, so that foreign matter generation and viscosity change can be suppressed, and a color filter excellent in transmittance and contrast ratio can be produced.

Hereinafter, the present invention will be described in detail.

The colored photosensitive resin composition of the present invention includes a red colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.

<Red colorant>

In the present invention, the red color does not refer to only one color having a specific color index, but refers to a red color.

The red colorant according to the present invention includes pigments and dyes.

The pigment according to the present invention may be an organic pigment, an inorganic pigment or a mixture thereof, which are generally used in the art.

The organic pigment is not particularly limited and may be a pigment used for printing ink, inkjet ink, etc. Specific examples thereof include water-soluble azo pigments, insoluble azo pigments, phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, Anthanthrone pigments, indanthrone pigments, pravanthrone pigments, anthraquinone pigments, anthraquinone pigments, anthanthrone pigments, anthanthrone pigments, indanthrone pigments, indanthrone pigments, Pyranthrone pigments, diketopyrrolopyrrole pigments, and the like. These may be used alone or in combination of two or more.

The inorganic pigment is not particularly limited and may be a metal compound such as a metal oxide or a metal complex salt and specifically includes a group consisting of iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony and carbon black &Lt; / RTI &gt; These may be used alone or in combination of two or more.

Organic pigments and inorganic pigments are classified as C.I. pigment among the compounds classified as pigments in the color index (The Society of Dyers and Colourists). Pigment Red, C.I. Pigment violet, C.I. Pigment Blue, and the like. Specific examples thereof include C.I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, , Preferably CI Pigment Red 122, 166, 177, 224, 242, 254, 255, and the like. These may be used alone or in combination of two or more.

The content of the pigment is not particularly limited and may be, for example, from 5 to 50% by weight, preferably from 10 to 35% by weight, based on the solid content of the colored photosensitive resin. When the content of the pigment is within the above range, it has an appropriate degree of curing and it is easy to secure a color region to be exhibited.

The dye according to the present invention comprises a xanthene dye represented by the following formula (1): &lt; EMI ID =

[Chemical Formula 1]

(Wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ are independently of each other a hydrogen atom or an alkyl group having 1 to 5 carbon atoms; R ₇ and R ₈ are each independently a hydrogen atom, -COOH ^{_{, -COO -, -SO 3 -,}} -SO 3 H, -SO 3 Na, -COOCH 3 or -COOCH ₂ CH _{3 Im).}

When a xanthene dye represented by the general formula (1) is contained, transmittance and contrast ratio are improved.

The xanthene dye represented by the general formula (1) is not particularly limited, and examples thereof include Acid Red 52, Basic Red 1, Basic Violet 10, Basic Violet 11, Rhodamine B, Rhodamine 6G, Rhodamine 123, Sulfolodamine B . These may be used alone or in combination of two or more.

The content of the dye is not particularly limited and may be, for example, 0.5 to 80% by weight, preferably 0.5 to 60% by weight based on the solid content of the red colorant. When the content of the dye is within the above range, it is possible to prevent the problem of lowering the reliability of dye elution by the organic solvent after pattern formation, and the sensitivity is excellent.

The content of the red colorant is not particularly limited and may be in the range of 5 to 60% by weight, preferably in the range of 10 to 45% by weight, based on the solid content of the total amount of the colored photosensitive resin composition. When the content of the red colorant is within the above range, the color density of the pixel is sufficient, and the lack of non-curing part during development does not deteriorate, so that the occurrence of residue can be reduced.

The red colorant is added to the composition in the form of a dispersion for uniform mixing in the composition. The dispersion may be prepared by further including a dispersant and a solvent used in the composition in addition to the colorant.

The dispersing agent is added for maintaining the deagglomeration and stability of the pigment and the dye, and any of those generally used in the art can be used without limitation. Preferably an acrylate-based dispersant comprising BMA (butyl methacrylate) or DMAEMA (N, N-dimethylaminoethyl methacrylate); Polycarboxylic acid esters; Unsaturated polyamides; Polycarboxylic acids; (Partial) amine salts of polycarboxylic acids; Ammonium salts of polycarboxylic acids; Alkylamine salts of polycarboxylic acids; Polysiloxanes; Long chain polyaminoamide phosphate salts; Esters of hydroxyl group-containing polycarboxylic acids and their modification products; An amide formed by the reaction of a polyester having a free carboxyl group with a poly (lower alkyleneimine) or a salt thereof; Soluble resin or water-soluble polymer compound such as (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylate ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol or polyvinylpyrrolidone; Polyester; Modified polyacrylates; Adducts of ethylene oxide / propylene oxide; Phosphate esters and the like. These may be used alone or in combination of two or more.

DISPER BYK-161, DISPER BYK-162, DISPER BYK-163, DISPER BYK-164, DISPER BYK-166, DISPER BYK-171, DISPER BYK- DISPER BYK-182, DISPER BYK-184, DISPER BYK-2000, DISPER BYK-2001, DISPER BYK-2070, DISPER BYK-2150 (BYK KEMISA); EFKA-44, EFKA-44, EFKA-47, EFKA-48, EFKA-4010, EFKA-4050, EFKA-4055, EFKA-4020, EFKA-4015, EFKA- 4400, EFKA-4406, EFKA-4510, EFKA-4800 (BASF); SOLSPERS-24000, SOLSPERS-32550, NBZ-4204/10 (Lubirzol); Hinoact T-6000, Hinoact T-7000, Hinoact T-8000 (Kawaken Fine Chemicals); AJISPUR PB-821, Ajisper PB-822, Ajisper PB-823 (Ajinomoto); FLORENE DOPA-17HF, Florene DOPA-15BHF, Florene DOPA-33 and Florene DOPA-44 (Kyoeisha Chemical Co., Ltd.). These may be used alone or in combination of two or more.

The content of the dispersing agent is not particularly limited and may be, for example, 5 to 60 parts by weight, preferably 15 to 50 parts by weight, based on 100 parts by weight of the pigment based on the solid content. When the content of the dispersing agent is within the above range, the pigment can be finely atomized and the red colorant can have an appropriate viscosity.

<Alkali-soluble resin>

The alkali-soluble resin is polymerized including an ethylenically unsaturated monomer having a carboxyl group. The ethylenically unsaturated monomer having a carboxyl group is a component that imparts solubility to an alkali developing solution used in a developing treatment process for forming a pattern.

The ethylenically unsaturated monomer having a carboxyl group is not particularly limited, and examples thereof include monocarboxylic acids such as acrylic acid, methacrylic acid and crotonic acid; Dicarboxylic acids such as fumaric acid, mesaconic acid and itaconic acid, and anhydrides thereof; mono (meth) acrylates of a polymer having a carboxyl group and a hydroxyl group at both terminals such as? -carboxypolycaprolactone mono (meth) acrylate, and the like, preferably acrylic acid and methacrylic acid. These may be used alone or in combination of two or more.

The acid value of the alkali-soluble resin is not particularly limited, and may be, for example, 30 to 170 mgKOH / g, preferably 50 to 160 mgKOH / g. When the acid value of the alkali-soluble resin is within the above range, the compatibility with the dye is excellent, the dye is not precipitated, the storage stability of the colored photosensitive resin composition is excellent, the proper viscosity can be maintained, and sufficient developing speed can be obtained.

A hydroxyl group may be added to secure the further developability of the alkali-soluble resin.

The method of imparting a hydroxyl group to the alkali-soluble resin is not particularly limited and includes, for example, a method of further polymerizing an ethylenically unsaturated monomer having a hydroxyl group, a method of reacting with a compound having a glycidyl group, A method of reacting a polymerized copolymer further including a monomer with a compound having a glycidyl group, and the like.

The ethylenically unsaturated monomer having a hydroxyl group is not particularly limited. (Meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl Hydroxyethyl acrylamide, and N-hydroxyethyl acrylamide. Of these, 2-hydroxyethyl (meth) acrylate is preferable. These may be used alone or in combination of two or more.

The compound having a glycidyl group is not particularly limited and includes, for example, butyl glycidyl ether, glycidyl propyl ether, glycidyl phenyl ether, 2-ethylhexyl glycidyl ether, glycidyl butyrate, glycidyl Methyl ethyl ether, ethyl glycidyl ether, glycidyl isopropyl ether, t-butyl glycidyl ether, benzyl glycidyl ether, glycidyl 4-t-butyl benzoate, glycidyl stearate, Diallyl ether, and methacrylic acid glycidyl ester. Of these, butyl glycidyl ether, aryl glycidyl ether, and methacrylic acid glycidyl ester may be preferably used. These may be used alone or in combination of two or more.

The alkali-soluble resin according to the present invention may further comprise at least one other monomer copolymerizable with the monomer. Methylstyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, o-vinylbenzyl methyl ether, m-vinylbenzyl methyl ether, p- Aromatic vinyl compounds such as vinyl benzyl methyl ether, o-vinyl benzyl glycidyl ether, m-vinyl benzyl glycidyl ether and p-vinyl benzyl glycidyl ether; N-cyclohexylmaleimide, N-benzylmaleimide, N-phenylmaleimide, No-hydroxyphenylmaleimide, Nm-hydroxyphenylmaleimide, Np-hydroxyphenylmaleimide, No-methylphenylmaleimide, Nm N-substituted maleimide-based compounds such as methylphenyl maleimide, Np-methylphenyl maleimide, No-methoxyphenyl maleimide, Nm-methoxyphenyl maleimide and Np-methoxyphenyl maleimide; Propyl (meth) acrylate, n-butyl (meth) acrylate, i-butyl (meth) acrylate, alkyl (meth) acrylates such as sec-butyl (meth) acrylate and t-butyl (meth) acrylate; (Meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, tricyclo [5.2.1.0 2,6] decan- Alicyclic (meth) acrylates such as dicyclopentanyloxyethyl (meth) acrylate and isobornyl (meth) acrylate; Aryl (meth) acrylates such as phenyl (meth) acrylate and benzyl (meth) acrylate; 3- (methacryloyloxymethyl) -2-trifluoromethyl oxetane, 3- (methacryloyloxymethyl) oxetane, 3- (methacryloyloxymethyl) 2- (methacryloyloxymethyl) oxetane, 2- (methacryloyloxymethyl) -4-trifluoromethyloxetane, and the like Unsaturated oxetane compounds, and the like. These may be used alone or in combination of two or more.

The content of the alkali-soluble resin is not particularly limited and may be, for example, 10 to 80% by weight, preferably 10 to 70% by weight, based on the solid content of the total amount of the colored photosensitive resin composition. When the content of the alkali-soluble resin is within the above range, solubility in a developing solution is sufficient and pattern formation is easy, and reduction of the film of the pixel portion of the exposed portion is prevented during development, so that the missing property of the non-pixel portion is improved.

One embodiment of the method for producing an alkali-soluble resin is as follows.

In a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel and a nitrogen-introducing tube, 0.1 to 10% of a polymerization initiator is added to 0.5 to 20 times the amount of the monomers, monomers, . Thereafter, the mixture is stirred at 40 to 140 DEG C for 1 to 10 hours.

The solvent used may be any of those used in ordinary radical polymerization reactions. Specific examples thereof include tetrahydrofuran, dioxane, ethylene glycol dimethylethyl, diethylene glycol dimethylethyl, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone Propanol, n-butanol, ethylene glycol monomethyl ether, propylene glycol monomethyl ether, toluene, xylene, ethylbenzene, methylene chloride, ethyl acetate, butyl acetate, propyleneglycol monomethyl ethyl acetate, 3-methoxybutyl acetate, Chloroform, dimethylsulfoxide, and the like, or a mixture thereof.

The polymerization initiator may be a polymerization initiator commonly used in the art and is not particularly limited. Specific examples thereof include diisopropylbenzene hydroperoxide, di-t-butyl peroxide, benzoyl peroxide, t-butyl peroxyisopropyl carbonate, t-amyl peroxy-2-ethylhexanoate, Organic peroxides such as 2-ethylhexanoate; Azo compounds such as 2,2'-azobis (isobutyronitrile), 2,2'-azobis (2,4-dimethylbarenonitrile) and dimethyl 2,2'-azobis (2-methylpropionate) Nitrogen compounds and the like. These may be used alone or in combination of two or more.

In the above process, an alpha -methylstyrene dimer or a mercapto compound may be used as a chain transfer agent to control the molecular weight. The? -methylstyrene dimer or the mercapto compound may be used in an amount of 0.005 to 5 parts by weight based on 100 parts by weight of the monomer. The above-mentioned polymerization conditions may be appropriately adjusted depending on the production equipment or the amount of heat generated by polymerization and the like.

< Photopolymerization  Compound &gt;

The photopolymerizable compound is a component for enhancing the strength of the pattern, and examples thereof include monofunctional, bifunctional or polyfunctional multimers, and preferably monomers having two or more functionalities. For example, a monofunctional acrylate such as nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate or N-vinylpyrrolidone Monomer; (Meth) acrylates such as 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di Bifunctional monomers such as 3-methylpentanediol di (meth) acrylate or 3-methylpentanediol di (meth) acrylate; (Meth) acrylate, trimethylolpropane tri (meth) acrylate, ethoxylated trimethylolpropane tri (meth) acrylate, propoxylated trimethylolpropane tri (meth) acrylate, pentaerythritol tri (Meth) acrylate, dipentaerythritol penta (meth) acrylate, ethoxylated dipentaerythritol hexa (meth) acrylate, propoxylated dipentaerythritol hexa (meth) acrylate, dipentaerythritol hexa (Meth) acrylate, and the like. These may be used alone or in combination of two or more.

The content of the photopolymerizable compound is not particularly limited and may be, for example, from 5 to 45% by weight, preferably from 7 to 45% by weight, based on the solid content of the total amount of the colored photosensitive resin composition. When the content of the photopolymerizable compound is within the above range, the strength and smoothness of the pixel portion can be good.

< Light curing Initiator >

The photopolymerization initiator according to the present invention includes a compound represented by the following formula (2): &lt; EMI ID =

(2)

이고; R₂ 및 R₃는 서로 독립적으로 히드록시기 또는 탄소수 1 내지 8의 알킬기로 치환 또는 비치환된 탄소수 1 내지 8의 알킬기, 페닐기, 벤질기 또는 디페닐설파이드기이며; R₄는 탄소수 1 내지 4의 알킬렌기이고; R₅는 탄소수 3 내지 8의 시클로알킬기임).(Wherein R &lt; _{1 &gt;} is

ego; R ₂ and R ₃ independently represent an alkyl group having 1 to 8 carbon atoms, a phenyl group, a benzyl group or a diphenylsulfide group which is substituted or unsubstituted with a hydroxy group or an alkyl group having 1 to 8 carbon atoms; R ₄ is an alkylene group having 1 to 4 carbon atoms; And R &lt; ₅ &gt; is a cycloalkyl group having 3 to 8 carbon atoms.

The photopolymerization initiator represented by the general formula (2) prevents photodegradation caused by the dye, thereby exhibiting effective photopolymerization properties in a colored photosensitive resin composition containing a dye as a colorant.

The colored photosensitive resin composition of the present invention may further include at least one photopolymerization initiator commonly used in the art besides the photopolymerization initiator represented by the general formula (2). For example, acetophenone, benzophenone, triazine, biimidazole, thioxanthone compounds and the like. These may be used alone or in combination of two or more.

The acetophenone compound is not particularly limited and includes, for example, diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethylketal, 2- (2-hydroxyethoxy) phenyl] -2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2- 1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan- ] Propane-1-one, and 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinophenyl) butan-1-one.

The benzophenone compound is not particularly limited, and examples thereof include benzophenone, methyl 0-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'- methyldiphenylsulfide, 3,3 ' -Tetra (tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone, and the like.

The triazine compound is not particularly limited, and examples thereof include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4- Methyl) -6- (4-methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2 , 2,4-bis (trichloromethyl) -6- [2- (5-methylpiperazin-1-yl) Yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (furan- (Trichloromethyl) -6- [2- (4-diethylamino-2-methylphenyl) ethenyl] -1,3,5-triazine, 2,4-bis (Trichloromethyl) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine.

The imidazole-based compound is not particularly limited, and examples thereof include 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,3-dichlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2-chlorophenyl) -4,4' Phenyl) imidazole, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetra (trialkoxyphenyl) biimidazole, 2,2- Phenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole or an imidazole compound in which the phenyl group at the 4,4', 5,5 'position is substituted with a carboalkoxy group , And preferably 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,3-dichlorophenyl ) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2-bis (2,6-dichlorophenyl) -4,4,5,5'-tetraphenyl- Imidazole and the like.

The thioxanthone compound is not particularly limited and includes, for example, 2-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1- Oakstone, and the like.

The content of the photopolymerization initiator is not particularly limited and may be, for example, from 0.1 to 40% by weight, preferably from 1 to 30% by weight, based on the total amount of the alkali-soluble resin and the photopolymerizable compound based on the solid content . When the content of the photopolymerization initiator is within the above range, the colored photosensitive resin composition becomes highly sensitive and the exposure time is shortened, so that productivity is improved and high resolution can be maintained, and the strength of the formed pixel portion and the smoothness on the surface of the pixel portion can be improved have.

The content of the compound represented by the general formula (2) in the photopolymerization initiator is not particularly limited and may be, for example, 10 to 100% by weight, preferably 20 to 100% by weight, based on the total weight of the photopolymerization initiator. When the content of the compound represented by the general formula (2) is within the above range, the sensitivity improving effect can be maximized.

< Light curing  Initiation supplements>

The colored photosensitive resin composition of the present invention may further include a photopolymerization initiation auxiliary agent for improving the sensitivity.

The photopolymerization initiation auxiliary is not particularly limited, and examples thereof include an amine compound, a carboxylic acid compound, and an organic sulfur compound having a thiol group. These may be used alone or in combination of two or more.

The amine compound is not particularly limited, and examples thereof include aliphatic amine compounds such as triethanolamine, methyldiethanolamine and triisopropanolamine; 4-dimethylaminobenzoic acid ethyl, 4-dimethylaminobenzoic acid isoamyl, 4-dimethylaminobenzoic acid 2-ethylhexyl, benzoic acid 2-dimethylaminoethyl, N, N-dimethylparatoluidine, Aromatic amine compounds such as 4'-bis (dimethylamino) benzophenone and 4,4'-bis (diethylamino) benzophenone.

The carboxylic acid compound is not particularly limited and includes, for example, phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, And aromatic heteroacetic acids such as phenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

The organic sulfur compound having a thiol group is not particularly limited and examples thereof include 2-mercaptobenzothiazole, 1,4-bis (3-mercaptobutyryloxy) butane, 1,3,5-tris (1H, 3H, 5H) -triene, trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis (3-mercaptopropionate), tetraethylene glycol bis (3-mercaptobutyrate), pentaerythritol tetrakis (3-mercaptopropionate), dipentaerythritol hexakis Phonate), and the like.

The content of the photopolymerization initiator is not particularly limited and may be, for example, 0.01 to 10% by weight, preferably 0.01 to 5% by weight based on the total weight of the colored photosensitive resin composition based on the solid content. When the content of the photopolymerization initiator is within the above range, the sensitivity of the colored photosensitive resin composition is further improved, and productivity to be formed therefrom can be improved.

<Solvent>

Solvents according to the present invention include propylene glycol monomethyl ether acetate and 4-hydroxy-4-methyl-2-pentanone. When propylene glycol monomethyl ether acetate and 4-hydroxy-4-methyl-2-pentanone are included, they are excellent in storage stability and can inhibit the generation of foreign matter and dye precipitation, And the contrast ratio of the color filter formed therefrom can be excellent.

The mixing ratio of the two solvents is not particularly limited. For example, propylene glycol monomethyl ether acetate and 4-hydroxy-4-methyl-2-pentanone may be mixed at a ratio of 90:10 to 60:40, May be mixed at a ratio of 80:20 to 70:30. When the mixing ratio is within the above range, the effect of improving the storage stability and dispersibility is maximized.

For example, the total weight of the colored photosensitive resin composition is 20 to 70% by weight of propylene glycol monomethyl ether acetate, 15 to 45% by weight of 4-hydroxy-4-methyl- %, And preferably 30 to 65 wt% of propylene glycol monomethyl ether acetate and 15 to 35 wt% of 4-hydroxy-4-methyl-2-pentanone. When the content of propylene glycol monomethyl ether acetate and 4-hydroxy-4-methyl-2-pentanone is within the above range, the effect of improving storage stability and dispersibility is maximized.

The colored photosensitive resin composition of the present invention may further contain a solvent commonly used in the art which is capable of dissolving the above components, and examples thereof include ethers, aromatic hydrocarbons, ketones, alcohols, . These may be used alone or in combination of two or more.

Specific examples 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 dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether Ethers such as ether acetate, methoxybutyl acetate and methoxypentyl acetate; Aromatic hydrocarbons such as benzene, toluene, xylene, and mesitylene; Ketones such as methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, and cyclohexanone; Alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol and glycerin; And esters such as ethyl 3-ethoxypropionate, methyl 3-methoxypropionate and? -Butyrolactone. Of these, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, Ethyl lactate, butylacetate, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate and the like.

The content of the solvent is not particularly limited and includes, for example, a solvent contained in the dispersion of the colorant, and the total content thereof may be included in the total weight of the colored photosensitive resin composition in an amount of 60 to 90% by weight, preferably 70 to 85% %. &Lt; / RTI &gt; When the content of the solvent is within the above range, the coating property may be good.

<Additives>

The colored photosensitive resin composition of the present invention may further comprise at least one additive selected from the group consisting of other polymer compounds, a curing agent, a surfactant, an adhesion promoter, an ultraviolet absorber and an anti-aggregation agent, if necessary.

The other polymer compound is not particularly limited, and examples thereof include curable resins such as epoxy resin and maleimide resin, polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl acrylate, polyester, Thermoplastic resins and the like.

The curing agent is a component for increasing deep curing and mechanical strength, and the type thereof is not particularly limited, and examples thereof include epoxy compounds, polyfunctional isocyanate compounds, melamine compounds, and oxetane compounds.

The epoxy compound is not particularly limited and includes, for example, bisphenol A epoxy resin, hydrogenated bisphenol A epoxy resin, bisphenol F epoxy resin, hydrogenated bisphenol F epoxy resin, novolak epoxy resin, other aromatic epoxy resin, Epoxy resins, glycidyl ester resins, glycidyl amine resins, or brominated derivatives of such epoxy resins; Aliphatic, alicyclic or aromatic epoxy compounds other than epoxy resins and brominated derivatives thereof; Butadiene (co) polymeric epoxide; Isoprene (co) polymeric epoxide; Glycidyl (meth) acrylate (co) polymers; Triglycidyl isocyanurate and the like.

The oxetane compound is not particularly limited and includes, for example, carbonate bisoxetane, xylene bisoxetane, adipate bisoxetane, terephthalate bisoxetane, cyclohexanedicarboxylic acid bisoxetane and the like .

The curing agent may be used together with a curing agent in combination with a curing auxiliary compound capable of ring-opening polymerization of the epoxy group of the epoxy compound and the oxetane skeleton of the oxetane compound.

The curing auxiliary compound is not particularly limited, and examples thereof include polyvalent carboxylic acids, polyvalent carboxylic acid anhydrides, and acid generators. Commercially available polyvalent carboxylic acid anhydrides can be used as an epoxy resin curing agent.

The commercially available epoxy resin curing agent that can be used in the present invention is not particularly limited and includes, for example, a trade name (Adeka Hadona EH-700) (manufactured by Adeka Kogyo Co., Ltd.), a trade name (Rikashido HH) Ltd.) and a trade name (MH-700) (manufactured by Shin-Etsu Chemical Co., Ltd.).

The kind of the surfactant is not particularly limited, and examples thereof include silicone, fluorine, ester, cationic, anionic, nonionic, amphoteric surfactant and the like.

Specific examples thereof include polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyethylene glycol diesters, sorbitan fatty acid esters, fatty acid-modified polyesters, tertiary amine-modified polyurethanes, polyethyleneimines and the like .

Commercially available products include KP (Shinetsugaku Kogaku Co., Ltd.), POLYFLOW (Kyoeisha Chemical Co., Ltd.), EFTOP (manufactured by TOKEM PRODUCTS CO., LTD.), MEGAFAC (Dainippon Ink Asahi guard, Surflon (available from Asahi Glass Co., Ltd.), SOLSPERSE (Lubrisol), EFKA (EFKA (trade name) manufactured by Asahi Chemical Industry Co., Ltd.), Flourad (Sumitomo 3M Co., Ltd.) PB 821 (Ajinomoto Co., Ltd.) and Disperbyk-series (BYK-chemi).

Examples of the adhesion promoter include, but are not limited to, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) Aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyl (meth) acrylate, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3- methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanatepropyltrimethoxysilane, 3-isocyanatepropyltriethoxysilane, and the like. These may be used alone or in combination of two or more.

The content of the adhesion promoter is not particularly limited and may be, for example, 0.01 to 10% by weight, preferably 0.05 to 2% by weight based on the total weight of the colored photosensitive resin composition based on the solid content.

The type of ultraviolet absorber is not particularly limited, and examples thereof include 2- (3-tert-butyl-2-hydroxy-5-methylphenyl) -5-chlorobenzothiazole and alkoxybenzophenone.

The anti-aggregation agent is not particularly limited and may be, for example, sodium polyacrylate.

The thus-prepared colored photosensitive resin composition is advantageous for achieving a high concentration and a high transmittance, and is excellent in dispersion stability and excellent in characteristics according to time, and therefore is useful as a raw material for forming a coloring pattern constituting a color filter.

&Lt; Method for producing colored photosensitive resin composition >

Examples of the method for preparing the colored photosensitive resin composition of the present invention include a method in which a pigment, a dye and a dispersant are added to and dispersed in a solvent to prepare a dispersion of a colorant having a uniform particle diameter, and then an alkali soluble resin dissolved in a solvent, A compound, a photopolymerization initiator and, if necessary, other additives and the like, and mixing them with the colorant dispersion, and adding the solvent again if necessary.

<Color filter>

The present invention also provides a color filter made of the colored photosensitive resin composition.

The color filter includes a substrate and a color layer formed on the substrate.

The substrate may be a substrate of the color filter itself, or may be a portion where the color filter is placed on a display device or the like, and is not particularly limited. The substrate may be glass, silicon (Si), silicon oxide (SiO _x ), or a polymer substrate. The polymer substrate may be polyethersulfone (PES) or polycarbonate (PC).

The color layer may be a layer containing the colored photosensitive resin composition of the present invention, and may be a layer formed by applying the colored photosensitive resin composition and exposing, developing, and thermosetting the colored photosensitive resin composition in a predetermined pattern.

The color filter including the substrate and the color layer as described above may further include a partition wall formed between each color pattern, and may further include a black matrix. Further, it may further comprise a protective film formed on the color layer of the color filter.

<Liquid Crystal Display Device>

The present invention also relates to a liquid crystal display device provided with the color filter.

The liquid crystal display device of the present invention may include a configuration known to those skilled in the art without the color filter, and is not particularly limited in the present invention.

It is to be understood that both the foregoing general description and the following detailed description of the present invention are exemplary and explanatory and are intended to be illustrative of the invention and are not intended to limit the scope of the claims. It will be apparent to those skilled in the art that such variations and modifications are within the scope of the appended claims.

Manufacturing example .

(1) Preparation of colorant dispersion

C.I. , 12.0 parts by weight of Pigment Red 254, 4.0 parts by weight of DISPERBYK-2001 (manufactured by BYK) as dispersing agent, 1.2 parts by weight of Acid Red 52, 72.8 parts by weight of propylene glycol methyl ether acetate as a solvent and 4 parts by weight of 4-hydroxy- -Pentanone 10 parts by weight were mixed and dispersed by a bead mill for 12 hours to prepare a red colorant.

(2) Preparation of colorant dispersion

C.I. 13.2 parts by weight of Pigment Red 254, 4.0 parts by weight of DISPERBYK-2001 (BYK) as a dispersant, 72.8 parts by weight of propylene glycol methyl ether acetate as a solvent and 10 parts by weight of 4-hydroxy-4-methyl- And mixed and dispersed by a mill for 12 hours to prepare a red colorant.

Synthetic example .

(1) Synthesis of alkali-soluble resin

A flask equipped with a stirrer, a thermometer reflux condenser, a dropping funnel and a nitrogen inlet tube was charged with 120 parts of propylene glycol monomethyl ether acetate, 80 parts of propylene glycol monomethyl ether, 2 parts of AIBN, 13.0 parts of acrylic acid, 10 parts of benzyl methacrylate, 57.0 parts of 4-methylstyrene, 20 parts of methyl methacrylate and 3 parts of n-dodecylmercaptan were charged, and air in the flask was replaced with nitrogen gas. Thereafter, the mixture was stirred at 110 DEG C and allowed to react for 6 hours. The alkali-soluble resin thus synthesized had a solid dispersion value of 100.2 mgKOH / g and a weight average molecular weight Mw of about 15110 as measured by GPC.

(2) Synthesis of alkali-soluble resin

A flask equipped with a stirrer, a thermometer reflux condenser, a dropping funnel and a nitrogen inlet tube was charged with 120 parts of propylene glycol monomethyl ether acetate, 80 parts of propylene glycol monomethyl ether, 2 parts of AIBN, 3.5 parts of acrylic acid, 10 parts of benzyl methacrylate, 66.5 parts of 4-methylstyrene, 20 parts of methyl methacrylate and 3 parts of n-dodecylmercaptan were charged, and air in the flask was replaced with nitrogen gas. Thereafter, the mixture was stirred at 110 DEG C and allowed to react for 6 hours. The alkali-soluble resin thus synthesized had a solid dispersion value of 26.5 mgKOH / g and a weight average molecular weight Mw of about 16070 as measured by GPC.

(3) Synthesis of alkali-soluble resin

A flask equipped with a stirrer, a thermometer reflux condenser, a dropping funnel and a nitrogen inlet tube was charged with 120 parts of propylene glycol monomethyl ether acetate, 80 parts of propylene glycol monomethyl ether, 2 parts of AIBN, 22.5 parts of acrylic acid, 10 parts of benzyl methacrylate, 47.5 parts of 4-methylstyrene, 20 parts of methyl methacrylate and 3 parts of n-dodecylmercaptan were substituted with nitrogen gas in the flask. Thereafter, the mixture was stirred at 110 DEG C and allowed to react for 6 hours. The thus-synthesized alkali-soluble resin had a solid dispersion value of 172.3 mgKOH / g and a weight average molecular weight Mw of about 14850 as measured by GPC.

Example  One.

39.8 parts of the colorant dispersion of Production Example (1), 11.1 parts of the resin of Synthesis Example (1), 3.7 parts of KAYARAD DPHA (Nippon Kayaku), 0.8 part of TR-PBG-305 (TRONLY), 0.1 parts of propylene glycol monomethyl ether Acetate 34.6 parts and 4-hydroxy-4-methyl-2-pentanone 10.0 parts were mixed to prepare a colored photosensitive resin composition.

Example  2.

39.8 parts of the colorant dispersion of Production Example (1), 11.1 parts of the resin of Synthesis Example (1), 3.7 parts of KAYARAD DPHA (Nippon Kayaku), 0.8 part of TR-PBG-305 (TRONLY), 0.1 parts of propylene glycol monomethyl ether Acetate 19.6 parts and 4-hydroxy-4-methyl-2-pentanone 25 parts were mixed to prepare a colored photosensitive resin composition.

Comparative Example  One.

39.8 parts of the colorant dispersion of Production Example (1), 11.1 parts of the resin of Synthesis Example (1), 3.7 parts of KAYARAD DPHA (Nippon Kayaku), 0.8 part of TR-PBG-305 (TRONLY), 0.1 parts of propylene glycol monomethyl ether Acetate (44.6 parts) were mixed to prepare a colored photosensitive resin composition.

Comparative Example  2.

39.8 parts of the colorant dispersion of Production Example (1), 11.1 parts of the resin of Synthesis Example (1), 3.7 parts of KAYARAD DPHA (Nippon Kayaku), 0.8 part of TR-PBG-305 (TRONLY) And 44.6 parts of 4-methyl-2-pentanone were mixed to prepare a colored photosensitive resin composition.

Comparative Example  3.

39.8 parts of the colorant dispersion of Production Example (1), 11.1 parts of the resin of Synthesis Example (2), 3.7 parts of KAYARAD DPHA (manufactured by Nippon Kayaku Co., Ltd.), 0.8 part of TR-PBG-305 (manufactured by TRONLY), propylene glycol monomethyl ether Acetate 34.6 parts and 4-hydroxy-4-methyl-2-pentanone 10.0 parts were mixed to prepare a colored photosensitive resin composition.

Comparative Example  4.

39.8 parts of the colorant dispersion of Production Example (1), 11.1 parts of the resin of Synthesis Example (3), 3.7 parts of KAYARAD DPHA (Nippon Kayaku), 0.8 part of TR-PBG-305 (TRONLY) Acetate 34.6 parts and 4-hydroxy-4-methyl-2-pentanone 10.0 parts were mixed to prepare a colored photosensitive resin composition.

Comparative Example  5.

39.8 parts of the colorant dispersion of Production Example (1), 11.1 parts of the resin of Synthesis Example (1), 3.7 parts of KAYARAD DPHA (Nippon Kayaku), 0.8 parts of Irgacure OXE01 (manufactured by BASF), 34.6 parts of propylene glycol monomethyl ether acetate And 10.0 parts of 4-hydroxy-4-methyl-2-pentanone were mixed to prepare a colored photosensitive resin composition.

Comparative Example  6.

39.8 parts of the colorant dispersion of Production Example (2), 11.1 parts of the resin of Synthesis Example (1), 3.7 parts of KAYARAD DPHA (Nippon Kayaku), 0.8 part of TR-PBG-305 (TRONLY) Acetate 34.6 parts and 4-hydroxy-4-methyl-2-pentanone 10.0 parts were mixed to prepare a colored photosensitive resin composition.

Experimental Example  One.

(1) Evaluation of viscosity change

The initial viscosity of the colored photosensitive resin compositions prepared in Examples and Comparative Examples was measured and stored at 5 캜 for one month, and the viscosity was measured to observe the change in viscosity. The viscosity was measured with a Brookfield viscometer (Brookfield Viscometer DVI +, manufactured by BROOKFIELD) at 25 ° C. The measurement results are shown in Table 1 below.

○: Viscosity change 5% or less

?: Change in viscosity exceeding 5% to 10%

×: Viscosity change exceeding 10%

(2) Evaluation of foreign matter

Each of the colored photosensitive resin compositions prepared in Examples and Comparative Examples was stored at 5 占 폚 for one month, and then observed with a reflection type optical microscope (observation magnification: 2,500 times) to perform foreign object evaluation. The evaluation results are shown in Table 1 below.

◎: Two or less foreign objects

○: 3 to 5 foreign objects

?: 6 to 10 foreign objects

X: 11 or more foreign objects

Experimental Example  2.

Each of the colored photosensitive resin compositions prepared in Examples and Comparative Examples was applied on a glass substrate (EAGLE XG, manufactured by Corning Incorporated) having a 2-inch square by spin coating, then placed on a heating plate and maintained at a temperature of 100 캜 for 3 minutes To form a thin film. Subsequently, a test photomask having a pattern for changing the transmittance in the range of 1 to 100% to a step-like pattern and a line / space pattern of 1 to 50 m was placed on the thin film and the distance between the test photomask and the test photomask was set to 100 m. Respectively. At this time, the ultraviolet light source was irradiated at a light intensity of 100 mJ / cm 2 using a 1 kW high pressure mercury lamp containing g, h and i lines. The thin film irradiated with ultraviolet rays was immersed in a KOH aqueous solution of pH 10.5 for 2 minutes to develop. The glass plate coated with the thin film was washed with distilled water, dried by blowing nitrogen gas, and heated in a heating oven at 200 ° C for 25 minutes to prepare a color filter. The film thickness of the manufactured color filter was 2.0 탆.

(1) Development speed measurement

The time taken for the unexposed area to completely dissolve in the developing solution at the time of development was measured and is shown in Table 1 below.

(2) Evaluation of adhesion

When the resulting pattern was evaluated by an optical microscope, the following pattern was evaluated on the basis of the degree of peeling, and the results are shown in Table 1 below.

○: No pattern peeling

△: 1 to 3 pattern peeling

X: Pattern peeling 4 or more

(3) pattern of Line width  Measure

The line width of the generated pattern was observed with a scanning electron microscope and measured. When the line width of the pattern is measured to be not less than the line width of the photomask, the sensitivity of the colored photosensitive resin composition is sufficient and the line width is enlarged. Table 1 shows the enlarged line widths of the photomask.

Experimental Example  3.

A color filter was prepared in the same manner as in Experimental Example 2 except that the test photomask was not used.

(1) Measurement of contrast ratio change

The color filter was similarly prepared from the colored photosensitive resin compositions of the examples and comparative examples in which the initial contrast ratio of the prepared color filter was measured and stored at 5 캜 for 1 month, and the contrast ratio was measured.

(2) Measurement of transmittance

And the transmittance in the visible light region was measured with a colorimeter (OSP-200, manufactured by Olympus Corporation). The results are shown in Table 1 below.

division Viscosity change Neglect Development speed
(second) Adhesiveness Pattern line width expansion (㎛) Contrast Ratio (%) Transmittance Example 1 ○ ○ 21 ○ 2.5 99 18.5 Example 2 △ ◎ 19 ○ 2.1 101.3 18.3 Comparative Example 1 X X 21 ○ 2.4 70.5 18.2 Comparative Example 2 X ◎ 19 ○ 2.2 98.3 18.3 Comparative Example 3 ○ ○ 48 ○ 3.1 99 18.4 Comparative Example 4 △ ○ 11 X 1.8 99.5 18.2 Comparative Example 5 ○ ○ 25 ○ -1.8 90.7 18.4 Comparative Example 6 ○ ◎ 23 ○ 4.1 100.5 17.5

Referring to Table 1, the compositions of Examples 1 and 2 exhibited less change in viscosity and less generation of foreign matter with time. Also, it can be seen that the developing speed in the production of the color filter is fast, the pattern adhesion is excellent, the change in the contrast ratio is small, and the sensitivity and the transmissivity are excellent.

However, the compositions of Comparative Examples 1 to 6 were inferior in at least one of storage stability, development speed, adhesion, sensitivity, contrast ratio, and transmittance, and thus a color filter excellent in all of the characteristics could not be produced.

Claims (8)

A red colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent;
Wherein the red colorant comprises a red pigment and a xanthene dye represented by Formula 1 below;
Wherein the alkali-soluble resin has an acid value of 30 to 170 mg KOH / g;
Wherein the photopolymerization initiator comprises a compound represented by the following formula (2);
Wherein the solvent comprises propylene glycol monomethyl ether acetate and 4-hydroxy-4-methyl-2-pentanone, propylene glycol monomethyl ether acetate and 4-hydroxy- 10 to 60:40. The colored photosensitive resin composition according to claim 1,
[Chemical Formula 1]

(Wherein R ₁ , R ₂ , R ₃ , R ₄ , R ₅ and R ₆ are independently of each other a hydrogen atom or an alkyl group having 1 to 5 carbon atoms; R ₇ and R ₈ are each independently a hydrogen atom, -COOH ^{_{, -COO -, -SO 3 -,}} -SO 3 H, -SO 3 Na, -COOCH 3 or -COOCH ₂ CH ₃ Im)
(2)

(Wherein R &lt; _{1 &gt;} is

ego; R ₂ and R ₃ independently represent an alkyl group having 1 to 8 carbon atoms, a phenyl group, a benzyl group or a diphenylsulfide group which is substituted or unsubstituted with a hydroxy group or an alkyl group having 1 to 8 carbon atoms; R ₄ is an alkylene group having 1 to 4 carbon atoms; And R &lt; ₅ &gt; is a cycloalkyl group having 3 to 8 carbon atoms.
The xanthene dye according to claim 1, wherein the xanthene dye is at least one selected from the group consisting of Acid Red 52, Basic Red 1, Basic Violet 10, Basic Violet 11, Rhodamine B, Rhodamine 6G, Rhodamine 123 and Sulfododamine B Colored photosensitive resin composition.
[4] The photosensitive resin composition according to claim 1, further comprising at least one photopolymerization initiator selected from the group consisting of an acetophenone compound, a benzophenone compound, a triazine compound, a biimidazole compound and a thioxanthone compound, Resin composition.
delete The colored photosensitive resin composition according to claim 1, further comprising at least one photopolymerization initiation auxiliary selected from the group consisting of an amine compound, a carboxylic acid compound and an organic sulfur compound having a thiol group.
2. The colored photosensitive resin composition according to claim 1, wherein the total weight of the colored photosensitive resin composition
The red colorant may be present in an amount of from 5 to 60%
The alkali-soluble resin preferably comprises 10 to 80% by weight,
Said photopolymerizable compound comprises from 5 to 45% by weight;
The photopolymerization initiator is contained in an amount of 0.1 to 40% by weight based on the total amount of the alkali-soluble resin and the photopolymerizable compound based on the solid content;
Wherein the solvent comprises 60 to 90% by weight of the total weight of the colored photosensitive resin composition.
A color filter made of the colored photosensitive resin composition according to any one of claims 1 to 3 and 5 to 6.
A liquid crystal display device comprising the color filter of claim 7.