KR101401488B1 - Colored photosensitive resin composition, and color filter and liquid crystal display device prepared by using the same - Google Patents

Abstract

The present invention relates to a colored photosensitive resin composition and a color filter and a liquid crystal display using the same. More particularly, the present invention relates to a color filter and a liquid crystal display using the color photosensitive resin composition, The present invention also relates to a color filter and a liquid crystal display device using the colored photosensitive resin composition, which exhibits excellent processability and high sensitivity even under the condition of forming an image with a low exposure dose by including an activator.

Wherein R ₁ is an ester group or an alkyl group having 1 to 20 carbon atoms, R ₂ , R ₃ and R ₄ are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms, and 1, m and n are integers from 1 to 20 .

 A colored photosensitive resin composition, a color filter, a liquid crystal display

Description

TECHNICAL FIELD [0001] The present invention relates to a colored photosensitive resin composition, and a color filter and a liquid crystal display device using the same. BACKGROUND ART [0002]

The present invention relates to a colored photosensitive resin composition exhibiting high sensitivity characteristics even under a pixel forming condition with a low exposure dose, a color filter manufactured using the composition, and a liquid crystal display device provided with the color filter.

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

Such a color filter is produced by a method of forming a desired coloring pattern using a colored photosensitive resin composition containing a coloring agent. Specifically, it is manufactured by forming a coating layer of a colored photosensitive resin composition on a substrate, forming a pattern on the formed coating layer, exposing and developing the coating layer, and heating and thermally curing the coating layer.

In recent years, in order to improve the productivity of a LCD manufacturing process, a color filter is manufactured by forming a pixel under a low exposure dose in the manufacture of a color filter. Thus, a colored photosensitive resin composition exhibiting high sensitivity even under a low exposure amount is used . However, although the conventionally used colored photosensitive resin composition is known to have a high sensitivity property, when a pixel is formed under a low exposure amount, a defective surface such as development unevenness occurs in the pixel portion.

In order to solve such problems, conventionally, there has been proposed a method of improving the leveling property of a colored photosensitive resin composition by using a surfactant to improve the processability in the production of a color filter. Examples of the surfactant include a fluorine surfactant, Modified silicone surfactants and the like were used. However, since such a surfactant has no reactivity with the photopolymerizable compound or the alkali-soluble resin contained in the colored photosensitive resin composition, there is a limit in improving the processability.

Therefore, it is required to develop a colored photosensitive resin composition for preventing surface defects when applied to the production of color filters and improving the productivity and yield of a LCD manufacturing process even under pixel formation conditions with excellent processability and low exposure dose.

An object of the present invention is to provide a colored photosensitive resin composition which exhibits high sensitivity characteristics even under a pixel forming condition with a low exposure dose and is excellent in processability.

It is another object of the present invention to provide a color filter in which surface defects such as development unevenness do not occur in the pixel portion.

It is still another object of the present invention to provide a liquid crystal display device having the color filter of the present invention.

As a result of intensive studies to solve the above problems, the inventors of the present invention have found that a colored photosensitive resin composition containing a reactive silicone surfactant represented by Chemical Formula 1 has excellent processability unlike the prior art, The present inventors have found that the surface defects do not occur even under the pixel forming conditions in which the exposure amount is low.

Accordingly, the present invention relates to a colored photosensitive resin composition comprising a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, a solvent, and a reactive silicone surfactant represented by the following formula (1)

[Chemical Formula 1]

Wherein R ₁ is an ester group or an alkyl group having 1 to 20 carbon atoms, R ₂ , R ₃ and R ₄ are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms, and 1, m and n are integers from 1 to 20 .

The present invention also provides a color filter comprising a color layer formed by applying a colored photosensitive resin composition on a substrate and exposing and developing it in a predetermined pattern, wherein the colored photosensitive resin composition comprises a colorant, an alkali- Wherein the color filter is a colored photosensitive resin composition comprising a compound, a photopolymerization initiator, a solvent, and a reactive silicone surfactant represented by the general formula (1).

In addition, the present invention provides a liquid crystal display device provided with the color filter.

The colored photosensitive resin composition according to the present invention can produce a color filter which exhibits high sensitivity characteristics even under pixel formation conditions with low exposure amounts and is excellent in processability so that surface defects such as development unevenness do not occur in the pixel portion, Thereby improving productivity and yield in the process. In addition, due to these properties, the colored photosensitive resin composition of the present invention is expected to be usefully used for the production of various high-quality color filters.

The present invention relates to a colored photosensitive resin composition which exhibits high sensitivity even under pixel formation conditions with low exposure amount, a color filter which does not cause surface defects such as development unevenness in a pixel portion by applying the colored photosensitive resin composition, And a liquid crystal display device.

Hereinafter, the present invention will be described in detail.

The colored photosensitive resin composition of the present invention comprises a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, a solvent, and a reactive silicone surfactant represented by the general formula (1).

The colored photosensitive resin composition may further include a photopolymerization initiator, a pigment dispersant, or other additives.

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

coloring agent

In the present invention, the color tone of the colorant is not limited, and the color tone can be selected according to the use of the color filter.

The colorant may be selected from pigments, dyes, natural pigments, or a combination of two or more pigments. Examples of the pigments include organic pigments, which are classified as pigments in the color index (The Society of Dyers and Colourists) , Or an inorganic pigment which is a metal oxide, a metal complex salt or an inorganic salt of barium sulfate, and it is preferable to use an organic pigment in view of excellent heat resistance and color development.

Specific examples of the organic pigments include C.I. Pigment Yellow 1, C.I. Pigment Yellow 3, C.I. Pigment Yellow 12, C.I. Pigment Yellow 13, C.I. Pigment Yellow 14, C.I. Pigment Yellow 15, C.I. Pigment Yellow 16, C.I. Pigment Yellow 17, C.I. Pigment Yellow 20, C.I. Pigment Yellow 24, C.I. Pigment Yellow 31, C.I. Pigment Yellow 53, C.I. Pigment Yellow 83, C.I. Pigment Yellow 86, C.I. Pigment Yellow 93, C.I. Pigment Yellow 94, C.I. Pigment Yellow 109, C.I. Pigment Yellow 110, C.I. Pigment Yellow 117, C.I. Pigment Yellow 125, C.I. Pigment Yellow 128, C.I. Pigment Yellow 137, C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 147, C.I. Pigment Yellow 148, C.I. Pigment Yellow 150, C.I. Pigment Yellow 153, C.I. Pigment Yellow 154, C.I. Pigment Yellow 166, C.I. Pigment Yellow 173, C.I. Pigment Yellow 194, C.I. Yellow pigments such as Pigment Yellow 214; C.I. Pigment Orange 13, C.I. Pigment Orange 31, C.I. Pigment Orange 38, C.I. Pigment Orange 40, C.I. Pigment Orange 42, C.I. Pigment Orange 43, C.I. Pigment Orange 51, C.I. Pigment Orange 55, C.I. Pigment Orange 59, C.I. Pigment Orange 61, C.I. Pigment Orange 64, C.I. Pigment Orange 65, C.I. Pigment Orange 71, C.I. Orange pigments such as Pigment Orange 73; C.I. Pigment Red 9, C.I. Pigment Red 97, C.I. Pigment Red 105, C.I. Pigment Red 122, C.I. Pigment Red 123, C.I. Pigment Red 144, C.I. Pigment Red 149, C.I. Pigment Red 166, C.I. Pigment Red 168, C.I. Pigment Red 176, C.I. Pigment Red 177, C.I. Pigment Red 180, C.I. Pigment Red 192, C.I. Pigment Red 209, C.I. Pigment Red 215, C.I. Pigment Red 216, C.I. Pigment Red 224, C.I. Pigment Red 242, C.I. Pigment Red 254, C.I. Pigment Red 264, C.I. Red pigments such as Pigment Red 265; C.I. Pigment Blue 15, C.I. Pigment Blue 15: 3, C.I. Pigment Blue 15: 4, C.I. Pigment Blue 15: 6, C.I. Blue pigments such as Pigment Blue 60; C.I. Pigment Violet 1, C.I. Pigment Violet 19, C.I. Pigment Violet 23, C.I. Pigment Violet 29, C.I. Pigment Violet 32, C.I. Pigment Violet 36, C.I. Violet pigments such as Pigment Violet 38; C.I. Pigment Green 7, C.I. Pigment Green 36, C.I. Green pigments such as Pigment Green 58; C.I. Pigment Brown 23, C.I. Brown pigments such as Pigment Brown 25; Or C.I. Pigment Black 1, C.I. Pigment Black 7 and the like. Preferably, C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, C.I. Pigment Red 177, C.I. Pigment Red 209, C.I. Pigment Red 254, C.I. Pigment Violet 23, C.I. Pigment Blue 15: 6 and C.I. Pigment Green 36. The term " pigment green 36 "

The organic pigment and the inorganic pigment may be used alone or in combination of two or more. As a specific example, in order to form red pixels, C.I. Pigment Red 254 and C.I. Pigment Yellow 139, and C.I. Pigment Green 36, C.I. Pigment Yellow 150 or C.I. A combination of Pigment Yellow 138 and C.I. Pigment Blue 15: 6.

The colorant may be contained in an amount of 5 to 60 mass%, preferably 10 to 50 mass%, based on the total solid content (100 mass%) in the colored photosensitive resin composition of the present invention. When such a content is included, the color density of the pixel is sufficient even if a thin film is formed, and the residue of the non-curing portion is not deteriorated during development, so that residue tends to be hardly generated. Here, the total solid content in the colored photosensitive resin composition means the total content of the remaining components excluding the solvent from the colored photosensitive resin composition.

When a pigment is used as the colorant, it is preferable to use a pigment having a uniform particle size. As a method of making the particle diameter of the pigment uniform, a method of dispersing the pigment by adding a surfactant as a pigment dispersant can be mentioned. According to this method, a pigment dispersion in which the pigment is uniformly dispersed in a solution can be obtained.

Examples of the pigment dispersant include surfactants such as cationic, anionic, nonionic, and amphoteric surfactants. These surfactants may be used alone or in combination of two or more.

The pigment dispersant is used in an amount of usually 1 part by mass or less, preferably 0.05 to 0.5 parts by mass, per 1 part by mass of the colorant. When used in the above-mentioned amounts, it is preferable because a pigment having a uniform average particle diameter tends to be obtained.

Alkali-soluble resin

In the present invention, the alkali-soluble resin may be an acrylic copolymer that is soluble in the solvent of the present invention and has reactivity to the action of light or heat, functions as a binder resin for the colorant and is soluble in an alkaline developer, Can be used without particular limitation.

Examples of the acrylic copolymer include a copolymer of a carboxyl group-containing monomer and other monomer copolymerizable with the monomer.

Specific examples of the carboxyl group-containing monomer include unsaturated carboxylic acids such as unsaturated monocarboxylic acids or unsaturated polycarboxylic acids having at least one carboxyl group in the molecule such as unsaturated dicarboxylic acid and unsaturated tricarboxylic acid. .

Examples of the unsaturated monocarboxylic acid include acrylic acid, methacrylic acid, crotonic acid,? -Chloroacrylic acid, cinnamic acid, and the like.

Examples of the unsaturated dicarboxylic acid include maleic acid, fumaric acid, itaconic acid, citraconic acid, and mesaconic acid. The unsaturated polycarboxylic acid may be an acid anhydride, and specific examples thereof include maleic anhydride, itaconic anhydride, citraconic anhydride and the like.

The unsaturated polycarboxylic acid may be its mono (2-methacryloyloxyalkyl) ester, for example, mono (2-acryloyloxyethyl) succinate, mono (2-methacryloyloxyethyl) Phthalic acid mono (2-acryloyloxyethyl), phthalic acid mono (2-methacryloyloxyethyl), and the like. The unsaturated polycarboxylic acid may be mono (meth) acrylate of the dicarboxylic polymer of both ends thereof, and examples thereof include ω-carboxypolycaprolactone monoacrylate, ω-carboxypolycaprolactone monomethacrylate and the like. .

These carboxyl group-containing monomers may be used alone or in combination of two or more.

Specific examples of the other monomers copolymerizable with the carboxyl group-containing monomer include styrene,? -Methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, p-chlorostyrene, o- P-methoxy styrene, o-vinyl benzyl methyl ether, m-vinyl benzyl methyl ether, p-vinyl benzyl methyl ether, o-vinyl benzyl glycidyl ether, m-vinyl benzyl glycidyl ether, Aromatic vinyl compounds such as vinylbenzyl glycidyl ether and indene;

Methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, i-propyl acrylate, i-propyl methacrylate, butyl methacrylate, i-butyl acrylate, i-butyl methacrylate, sec-butyl acrylate, sec-butyl methacrylate, t-butyl acrylate, t-butyl methacrylate, Ethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate, 2-hydroxybutyl methacrylate, 3-hydroxybutyl acrylate, 3-hydroxybutyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, Acrylate, benzyl acrylate, benzyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, phenyl acrylate, phenyl methacrylate, 2-methoxyethyl acrylate, 2-methoxyethyl Methacrylate, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate, methoxy diethylene glycol acrylate, methoxy diethylene glycol methacrylate, methoxy triethylene glycol acrylate, methoxy triethylene glycol methacrylate Acrylate, methoxypropylene glycol methacrylate, methoxypropylene glycol acrylate, methoxydipropylene glycol methacrylate, isobornyl acrylate, isobornyl methacrylate, dicyclopentadiene Acrylate, dicyclopentadienyl methacrylate, 2-hydroxy-3-phenoxy Acrylate, 2-hydroxy-3-phenoxypropyl methacrylate, glycerol monoacrylate, glycerol monomethacrylate, such as unsaturated carboxylic acid esters;

Aminoethyl methacrylate, 2-aminoethyl methacrylate, 2-dimethylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate, 2-aminopropyl acrylate, 2-aminopropyl methacrylate, 2- Unsaturated carboxylates such as methyl acrylate, ethyl acrylate, propyl methacrylate, isopropyl acrylate, isopropyl acrylate, isopropyl acrylate, isopropyl acrylate, isopropyl acrylate, Acid amino alkyl esters;

Unsaturated carboxylic acid glycidyl esters such as glycidyl acrylate and glycidyl methacrylate;

Carboxylic acid vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate and vinyl benzoate;

Unsaturated ethers such as vinyl methyl ether, vinyl ethyl ether and allyl glycidyl ether;

Vinyl cyanide compounds such as acrylonitrile, methacrylonitrile,? -Chloroacrylonitrile, and vinylidene cyanide;

Unsaturated amides such as acrylamide, methacrylamide,? -Chloroacrylamide, N-2-hydroxyethyl acrylamide and N-2-hydroxyethyl methacrylamide;

Maleimide, N-phenylmaleimide. Unsaturated imides such as N-cyclohexylmaleimide;

Aliphatic conjugated dienes such as 1,3-butadiene, isoprene and chloroprene;

Polystyrene, polymethyl acrylate, polymethyl methacrylate, poly-n-butyl acrylate, poly-n-butyl methacrylate, polysiloxane having a monoacryloyl group or monomethacryloyl group at the end of the polymer molecular chain Macromers and the like.

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

The content of the carboxyl group-containing monomer unit in the alkali-soluble resin is usually 10 to 50 mass%, preferably 15 to 40 mass%, and more preferably 25 to 40 mass%. When the content of the carboxyl group-containing monomer unit is 10 to 50% by mass, the solubility in a developing solution is favorable, and a pattern at the time of development tends to be accurately formed, which is preferable.

Examples of the acrylic copolymer include (meth) acrylic acid / methyl (meth) acrylate copolymer, (meth) acrylic acid / benzyl (meth) acrylate copolymer, (meth) acrylic acid / 2- (Meth) acrylate / benzyl (meth) acrylate copolymer, a (meth) acrylic acid / methyl (meth) acrylate / polystyrene macromonomer copolymer, a (Meth) acrylic acid / benzyl (meth) acrylate / polymethyl (meth) acrylate macromonomer copolymer, (meth) acrylic acid / benzyl (meth) acrylate / polystyrene macromonomer copolymer, (Meth) acrylate / benzyl (meth) acrylate / polystyrene macromonomer copolymer, 2-hydroxyethyl (meth) acrylate / benzyl (Meth) acrylic acid / styrene / benzyl (meth) acrylate / N-phenylmaleimide copolymer, (meth) acrylic acid / succinic acid mono (2-acryloyloxy) Acrylic acid / succinic acid mono (2-acryloyloxyethyl) / styrene / allyl (meth) acrylate / N-phenylmaleimide copolymer / styrene / benzyl (Meth) acrylic acid / benzyl (meth) acrylate / N-phenylmaleimide / styrene / glycerol mono (meth) acrylate copolymer. Here, (meth) acrylate means acrylate or methacrylate.

Of these, (meth) acrylic acid / benzyl (meth) acrylate copolymer, (meth) acrylic acid / benzyl (meth) acrylate / styrene copolymer, (meth) acrylic acid / methyl / Methyl (meth) acrylate / styrene copolymer is preferably used.

The weight average molecular weight of the alkali-soluble resin in terms of polystyrene is usually 5,000 to 50,000, preferably 8,000 to 40,000, more preferably 10,000 to 35,000, and most preferably 10,000 to 30,000. When the molecular weight of the alkali-soluble resin is 5,000 to 50,000, the hardness of the coating film is improved, the residual film ratio is high, the solubility of the unexposed portion in the developing solution is good, and the resolution tends to be improved.

The acid value of the alkali-soluble resin is usually 50 to 150, preferably 60 to 140, more preferably 80 to 135, and most preferably 80 to 130. When the acid value is in the range of 50 to 150, the solubility in the developer is improved, the unexposed portions are easily dissolved, the sensitivity is increased, and the pattern of the exposed portions in the development remains to improve the residual film ratio. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide necessary for neutralizing 1 g of the acrylic polymer, and can be generally determined by titration using an aqueous solution of potassium hydroxide.

The alkali-soluble resin may be contained in an amount of 5 to 85 mass%, preferably 10 to 70 mass%, based on the total solid content (100 mass%) in the colored photosensitive resin composition of the present invention. When such a content is included, the solubility in the developing solution is sufficient, so that development residue does not easily occur on the substrate of the non-pixel portion, and film reduction of the pixel portion of the exposed portion is hardly caused at the time of development, It is preferable since it tends to be good.

Photopolymerization  compound

In the present invention, the photopolymerizable compound is a photopolymerizable compound that can be polymerized by an active radical, acid, or the like generated from a photopolymerization initiator by irradiation of light. In the present specification, the term "photopolymerizable compound" means a monomer having at least one functional group and is described as a monofunctional, bifunctional, or bifunctional polymerizable compound depending on the number of functional groups.

Specific examples of the monofunctional polymerizable compound include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate, Pyrrolidone and the like.

Specific examples of the bifunctional polymerizable compound include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) Acrylate, bis (acryloyloxyethyl) ether of bisphenol A, 3-methylpentanediol di (meth) acrylate, butylene glycol dimethacrylate, hexanediol di (meth) acrylate, diethylene glycol di (Meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, dipropylene glycol diacrylate, tripropylene glycol diacrylate, ethoxy Diethyleneglycol diacrylate, diethyleneglycol diacrylate, diethyleneglycol diacrylate, diethyleneglycol diacrylate, and the like.

Specific examples of the triblock polymerizable compound include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, ethoxylate trimethylolpropane tri (meth) acrylate, propyloxylate trimethylolpropane tri (Meth) acrylate, glyceryl propyloxytriacrylate, isocyanurate triarylate, and the like.

Specific examples of the tetrafunctional polymerizable compound include pentaerythritol tetra (meth) acrylate, dimethylol propane tetra (methyl) acrylate, and the like.

Specific examples of the pentafunctional polymerizable compound include dipentaerythritol penta (meth) acrylate, and specific examples of the hexafunctional photopolymerizable compound include dipentaerythritol hexa (meth) acrylate.

Of these, multifunctional polymerizable compounds having two or more functionalities are preferably used. Particularly preferred is a polyfunctional polymerizable compound having five or more functionalities.

The photopolymerizable compound is preferably contained in an amount of 5 to 50 mass%, more preferably 7 to 45 mass%, based on the total solid content (100 mass%) in the colored photosensitive resin composition. When such a content is included, the strength and smoothness of the pixel portion tends to be favorable.

Light curing Initiator

In the present invention, the photopolymerization initiator can be used without any particular limitation as long as it can polymerize the alkali-soluble resin and the photopolymerizable compound. In particular, from the viewpoints of polymerization characteristics, initiation efficiency, absorption wavelength, availability, and price, it is preferable to use an acetophenone, benzoin, benzophenone, thioxanthone, triazine, oxime, And a benzoin tosylate-based compound, and a light stabilizer may be used in combination. The photopolymerization initiator may be divided into an active radical generator which generates an active radical upon irradiation with light, a sensitizer, an acid generator, and the like.

Examples of the active radical generator include benzoin, acetophenone, benzophenone, thioxanthone, triazine, and oxime compounds.

Specific examples of the acetophenone-based compound include diethoxyacetophenone, 2-methyl-2-morpholino-1- (4-methylthiophenyl) propan- Phenylpropane-1-one, benzyldimethylketal, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) Oligomers of 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propan- Methylthiophenyl) propan-1-one are more preferable. The acetophenone-based compounds may be used alone or in combination of two or more, and may be used in combination with other photopolymerization initiators.

Specific examples of the benzoin compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether.

Specific examples of the benzophenone compound include benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3 ', 4,4'- Butyl peroxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone, and the like.

Specific examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1- Propanedioxanthone, and the like.

Specific examples of triazine compounds include 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- (4- methoxystyryl) Bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4- (Trichloromethyl) -6- [2- (4-diethylamino-2- (trifluoromethyl) Methylphenyl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (3,4- dimethoxyphenyl) ethenyl] -1,3,5- Triazine, and the like.

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

Specific examples of the sensitizer include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,2-bis (o-chlorophenyl) -4,4 ', 5,5'-tetraphenyl- Benzyl, 9,10-phenanthrenequinone, camphorquinone, methyl phenylglyoxylate, titanocene compounds, and the like can be given. have.

Specific examples of the acid generator include 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate , 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyl iodonium p-toluenesulfonate, di Onium salts such as phenyl iodonium hexafluoroantimonate, and nitrobenzyl tosylates, benzoin tosylates and the like. Among the above compounds, for example, there are compounds which simultaneously generate an active radical and an acid such as a triazine-based compound.

The photopolymerization initiator may be contained in an amount of 0.1 to 40 mass%, preferably 1 to 30 mass%, based on the total solids content (100 mass%) of the alkali-soluble resin and the photopolymerizable compound of the present invention. When such a content is included, the colored photosensitive resin composition is highly sensitized and the exposure time is shortened, which is preferable because productivity can be improved and high resolution can be maintained.

In the present invention, a photopolymerization initiator may be further added together with a photopolymerization initiator. The photopolymerization initiator is used in combination with a photopolymerization initiator and is used to promote polymerization of the photopolymerizable compound initiated by the photopolymerization initiator. Examples of the photopolymerization initiator include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and the like.

Specific examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, (Dimethylamino) benzophenone, 4,4'-bis (diethylamino) benzophenone, 4,4'-bis (dimethylamino) benzophenone, Bis (ethylmethylamino) benzophenone, and 4,4'-bis (diethylamino) benzophenone are preferable.

Specific examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, .

Specific examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1- -Propoxyloxanthone, and the like.

The photopolymerization initiator may be used alone or in combination of two or more. A commercially available product, EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used.

Specific examples of the combination of the preferred photopolymerization initiator and the photopolymerization initiator are diethoxyacetophenone and 4,4'-bis (diethylamino) benzophenone; 2-methyl-2-morpholino-1- (4-methylthiophenyl) propan-1-one and 4,4'-bis (diethylamino) benzophenone; 2-hydroxy-2-methyl-phenylpropan-1-one and 4,4'-bis (diethylamino) benzophenone; 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl] propan-1-one and 4,4'-bis (diethylamino) benzophenone; 1-hydroxycyclohexyl phenyl ketone and 4,4'-bis (diethylamino) benzophenone; Oligomers of 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propan-1-one and 4,4'-bis (diethylamino) benzophenone; A combination of 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one and 4,4'-bis (diethylamino) benzophenone, Methyl-2-morpholino-1- (4-methylthiophenyl) propan-1-one and 4,4'-bis (diethylamino) benzophenone.

When the photopolymerization initiator and the photopolymerization initiator are used together, the content of the photopolymerization initiator is preferably 10 mol or less, more preferably 0.01 to 5 mol based on 1 mol of the photopolymerization initiator. When the photopolymerization initiator is used in the same amount as described above, the sensitivity of the colored photosensitive resin composition is higher and the productivity of the color filter formed using the composition tends to be improved.

solvent

In the present invention, the solvent is not particularly limited as long as it is effective for dispersing or dissolving the other components contained in the colored photosensitive resin composition. The solvent may be selected from esters, aromatic hydrocarbons, ketones, alcohols, Drew and the like are preferable.

Specific examples of the ethers include tetrahydrofuran, tetrahydropyrane, 1,4-dioxane, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol mono Methyl ethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, propylene glycol methyl ether, propylene Propyleneglycol monomethyl ether acetate, propyleneglycol monopropyl ether acetate, methyl cellosolve acetate, ethyl cellosolve acetate, ethyl carbitol acetate, butyl carbitol acetate, propyleneglycol methyl ether acetate, methoxy Butylacetate And the like can be given site, methoxy pentyl acetate, anisole, phenetole or methyl anisole.

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

Specific examples of the ketone include acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone or cyclohexanone.

Specific examples of the alcohols include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and glycerin.

Specific examples of the esters include ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, butyl butyrate, alkyl esters, Methyl methoxyacetate, methyl methoxyacetate, methyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-oxypropionate, 3- Ethyl propionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-oxypropionate, ethyl 2-oxypropionate, Methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, 2- Methyl propionate, methyl 2-oxy-2-methylpropionate, ethyl 2-oxy-2-methylpropionate, methyl 2-methoxy- But are not limited to, methyl ethyl ketone, ethyl methyl ketone, ethyl methyl ketone, ethyl methyl ketone, ethyl methyl ketone, ethyl methyl ketone, ethyl methyl ketone, ethyl methyl ketone, ethyl methyl ketone, And lactones.

Specific examples of amides include N, N-dimethylformamide or N, N-dimethylacetamide.

Examples of other solvents include N-methylpyrrolidone and dimethylsulfoxide.

Preferably, ethyl 3-ethoxypropionate, propylene glycol monomethyl ether acetate or propylene glycol methyl ether are used alone or in combination of two or more.

The solvent may be contained in an amount of 60 to 90 mass%, preferably 70 to 85 mass%, based on the total amount (100 mass%) of the colored photosensitive resin composition of the present invention containing the above-mentioned solvent. When it is contained in the above-mentioned amounts, when it is coated with a coating device such as a roll coater, a spin coater, a slit and spin coater, a slit coater (or a "die coater") or an inkjet, desirable.

Reactive silicone surfactant

In the present invention, the reactive silicone surfactant is a compound that can be polymerized by an active radical or an acid generated from a photopolymerization initiator by irradiation with light, and is excellent in reactivity with the photopolymerizable compound or alkali-soluble resin, Thereby improving the sensitivity and fairness of the composition.

The reactive silicone surfactant is a compound containing a siloxane bond and a reactive acrylate chain, and may be a compound represented by the following formula (1).

[Chemical Formula 1]

Wherein R ₁ is an ester group or an alkyl group having 1 to 20 carbon atoms, R ₂ , R ₃ and R ₄ are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms, and 1, m and n are integers from 1 to 20 .

The alkyl group having 1 to 10 carbon atoms may be methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, desirable.

Preferably, the reactive silicone surfactant may be a compound represented by the following formula (2), wherein R ₂ , R ₃ , and R ₄ each independently represents a methyl group.

(2)

Wherein R ₁ is an ester group or an alkyl group having 1 to 20 carbon atoms, and 1, m and n are an integer of 1 to 20.

Specific examples of the reactive silicone surfactant include Tego Rad 2100, Tego Rad 2200N, Tego Rad 2250, Tego Rad 2300, Tego Rad 2500, Tego Rad 2600, and Tego Rad 2700 (manufactured by Degussa).

In the present invention, a silicon-containing surfactant, a silicon-based surfactant or a fluorinated surfactant having a fluorine atom is further contained in an amount of 60 mass% or less based on the total content of the reactive silicon surfactant (100 mass%), together with the reactive silicon surface- It is possible.

Examples of the silicon-based surfactant having a fluorine atom include a surfactant having a siloxane bond and a fluorocarbon chain. Specific examples include Megapox (registered trademark) R08, Megapax BL20, Megapax F475, Megapax F477, Megapax F443 (manufactured by Dainippon Ink Kagaku Kogyo), and Megapax F475 is preferable.

As the silicone surfactant, a surfactant having a siloxane bond can be mentioned. Specific examples thereof include Toray Silicon DC3PA, Toray Silicon DC11PA, Toray Silicone SH21PA, Toray Silicone SH28PA, Toray Silicon 29SHPA, Toray Silicone SH30PA, Polyether Modified Silicone Oil SH8400 (trade name: Toray Silicone Co., Ltd.), KP321, KP322, KP323, KP324, KP340, KP341 (manufactured by Shin-Etsu Silicone), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452 and TSF4460 (manufactured by Jitoshiba Silicone Co., Ltd.).

Examples of the fluorochemical surfactant include a surfactant having a fluorocarbon chain. Specific examples thereof include Florinate (registered trademark) FC430, Florinate FC431 (manufactured by Sumitomo 3M Ltd.), Megafox (registered trademark) F142D, Megafox F171, Megafox F172, Megafox F173, Megafox F177, Megafox F183 , Megapax R30 (manufactured by Dainippon Ink and Chemicals, Incorporated), and E5844 (manufactured by Daikin Fine Chemical Co., Ltd.).

The reactive silicone surfactant is preferably contained in an amount of 0.001 to 14 mass%, more preferably 0.1 to 10 mass%, based on the total solid content (100 mass%) in the colored photosensitive resin composition of the present invention. When the content is 0.001 to 14 mass%, it is possible to produce a colored photosensitive resin composition that does not cause surface defects such as development unevenness even under pixel formation conditions with a low exposure amount.

The colored photosensitive resin composition of the present invention containing the above components may further contain a small amount of additives such as a pigment dispersant, a defoaming agent, a heat crosslinking agent, and an adhesion promoter in order to improve performance as required.

The colored photosensitive resin composition of the present invention can be produced, for example, by the following method. The colorant is mixed with a solvent in advance and dispersed using a bead mill or the like until the average particle diameter of the colorant becomes about 0.2 탆 or less. At this time, a pigment dispersant may be used if necessary, and some or all of the alkali-soluble resin may be blended. The remainder of the alkali-soluble resin, the photopolymerizable compound, the photopolymerization initiator and the reactive silicone surfactant, and other components which are used if necessary, and the additional solvent (if necessary) are added to the obtained dispersion (hereinafter also referred to as "mill base" Is further added to a predetermined concentration to obtain a desired colored photosensitive resin composition.

The colored photosensitive resin composition of the present invention is applied to the production of a color filter, and the color filter of the present invention and a method for producing the same will be described below.

The color filter of the present invention comprises 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 a glass plate, a silicon wafer, a plate of a plastic substrate such as polyethersulfone (PES), polycarbonate (PC), or the like. That is, the substrate may be a substrate of silicon (Si), silicon oxide (SiO _x ), a glass plate, or a polymer substrate of a plastic substrate.

The color layer is a layer containing a colored photosensitive resin composition comprising a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, a solvent and a reactive silicone surfactant represented by the general formula (1) Developing, developing and thermosetting in a pattern of a photolithography process.

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.

Figs. 1A to 1C show a procedure for producing a color filter including a color layer formed from the above-mentioned colored photosensitive resin composition.

In the production of a color filter, the colored photosensitive resin composition of the present invention is subjected to pattern treatment in order to form a colored pattern. Specifically, as shown in FIG. 1A, a color layer 11 made of a colored photosensitive resin composition is formed on a substrate 10, and a color layer 11 formed as shown in FIG. , And then developed as shown in Fig. 1C.

In order to form the color layer 11 made of the colored photosensitive resin composition on the substrate 10 as shown in FIG. 1A, for example, a colored photosensitive resin composition diluted with a solvent is spun, Is coated on the substrate by a coating method such as roll, spray, or ink jet method, and then volatile components such as a solvent are volatilized. Thereby, a color layer 11 made of a colored photosensitive resin composition is formed. The formed color layer is composed of solid components of the colored photosensitive resin composition and contains little volatile components. The thickness of the color layer is determined by coating conditions such as the viscosity of the colored photosensitive resin composition, the concentration of the solid component, the coating speed, etc. When the colored photosensitive resin composition of the present invention is used, the color layer 11 ) Can be formed.

Next, the color layer 11 formed to irradiate the color layer 11 formed as shown in Fig. 1B in a predetermined pattern is exposed to light. In order to expose, for example, the color layer 11 is irradiated with a predetermined pattern through a photomask 20. As the light, g-line (wavelength: 436 nm), h-line and i-line (wavelength: 365 nm) of ultraviolet rays are usually used. The light rays pass according to the pattern of the photomask. The photomask 20 is formed by providing a light-shielding layer for shielding a light beam on a surface of a glass plate in a predetermined pattern. The light ray is shielded by the light shielding layer, and the portion of the photomask 20 to which the light shielding layer is not provided is a light transmitting portion through which the light ray passes. According to the pattern of the light transmitting portion, the color layer 11 is exposed. The irradiation dose of the light ray is appropriately selected according to the used colored photosensitive resin composition. The portion irradiated with the light ray has a much lower solubility than the portion irradiated with no light ray, so that the difference in solubility between the two portions is maximized.

Next, as shown in Fig. 1C, development is performed after exposure. For the development, for example, the colored photosensitive resin composition layer after exposure is immersed in a developer. As the developer, an alkaline compound, specifically, an aqueous solution of sodium carbonate, sodium hydroxide, potassium hydroxide, potassium carbonate, tetramethylammonium hydroxide or the like is used. Through the development, the light ray unirradiated region not irradiated with the light ray of the layer formed from the colored photosensitive resin composition is removed. On the contrary, the light-irradiated region irradiated by the light ray remains to constitute a coloring pattern.

After the development is completed, the developed layer is washed with ordinary water and dried to obtain a predetermined coloring pattern. After drying, a heat treatment may be performed. The colored pattern formed by the heat treatment is thermally cured, thereby improving the mechanical strength. Since the mechanical strength of the colored pattern can be improved by the heat treatment as described above, it is preferable to use a colored photosensitive composition containing a curing agent. At this time, the heating temperature is usually 180 ° C or higher, preferably 200 to 250 ° C.

A liquid crystal display device of the present invention comprises a color filter of the present invention comprising a substrate and a color layer.

The color filter comprises a substrate, and a colored photosensitive resin composition comprising a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, a solvent and a reactive silicone surfactant represented by Chemical Formula 1 on the substrate, And a color layer formed by exposure, development and thermosetting.

The liquid crystal display includes a configuration known to those skilled in the art, except that the color filter is provided.

It will be apparent to those skilled in the art that various modifications and variations can be made in the present invention without departing from the spirit or scope of the present invention. Such variations and modifications are intended to be within the scope of the appended claims.

In the following Examples and Comparative Examples, "%" and "part" representing the content are on a mass basis unless otherwise specified.

Example  One

≪ Preparation of colored photosensitive resin composition &

C.I. 3.55 parts of Pigment Blue 15: 6 (1-A)

9.57 parts of a copolymer of methacrylic acid and benzyl methacrylate (the molar ratio of methacrylic acid unit to benzyl methacrylate unit: 27:73, acid value: 83, weight average molecular weight: 18,000) as an alkali-soluble resin,

As the photopolymerizable compound, 2.79 parts of dipentaerythritol hexaacrylate (3-A)

0.74 part of 2-methyl-2-morpholino-1- (4-methylthiophenyl) propane-1-one (4-A)

0.37 part of 4,4'-bis (diethylamino) benzophenone (4-B) as a photopolymerization initiator,

0.24 parts of TEGO (registered trademark) Rad 2700 (5-A) (Degussa) as a reactive silicone surfactant,

26.39 parts of ethyl 3-ethoxypropionate (6-A), 54.01 parts of propylene glycol monomethyl ether acetate (6-B) as a solvent,

1.08 parts of a polyester-based pigment dispersant (7-A) as an additive, 1.24 parts of an epoxy resin (SUMI-EPOXY ESCN-195XL) (7-B) as a thermal crosslinking agent, C) (0.02 part) were mixed and dispersed to prepare a colored photosensitive resin composition.

≪ Production of color filter &

The colored photosensitive resin composition thus prepared was applied to the top of a glass substrate by a spin coating method and then placed on a heating plate and held at a temperature of 100 ° C for 3 minutes to form a color layer thin film. Subsequently, a test photomask having a pattern changing in a stepwise manner with a transmittance of 1 to 100% and a line / space pattern of 1 to 50 m was placed on the color layer thin film, And irradiated with ultraviolet rays. 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, and no special optical filter was used. The color layer thin film irradiated with ultraviolet rays was immersed in a KOH aqueous solution of pH 10.5 for 2 minutes for development. The glass substrate on which the developed color layer thin film was formed was washed with distilled water, dried in a nitrogen gas atmosphere, and heated for 1 hour in a heating oven at 200 ° C to thermally cure the color filter. The thickness of the color layer of the manufactured color filter was 1.8 mu m.

Example  2

In the preparation of the colored photosensitive resin composition in Example 1, 0.48 part of TEGO Rad 2700 (5-A), which is a reactive silicone surfactant, and 0.48 part of propylene glycol monomethyl ether acetate (6-B ) Was used instead of 53.77 parts of the above-mentioned catalyst.

Example  3

In the preparation of the colored photosensitive resin composition in Example 1, 0.96 part of Tego Rad 2700 (5-A), which is a reactive silicone surfactant, and 0.96 part of propylene glycol monomethyl ether acetate (6-B ) Was used in place of 53.29 parts of the polyimide precursor.

Example  4

In the preparation of the colored photosensitive resin composition in Example 1, 0.96 part of Tego Rad 2700 (5-A), Megafox (registered trademark) F475 (5-C), which is a reactive silicone surfactant, , And 52.81 parts of propylene glycol monomethyl ether acetate (6-B), which was a solvent, were used as the solvent.

Comparative Example  One

In the preparation of the colored photosensitive resin composition in Example 1, polyether-modified silicone oil SH8400 (manufactured by Toray Silicone Co., Ltd.) was used instead of Tego Rad 2700 (5-A), which is a reactive silicone surfactant, (5-B) was used instead of the compound (5-B).

Comparative Example  2

In the preparation of the colored photosensitive resin composition in Example 1, polyether-modified silicone oil SH8400 (manufactured by Toray Silicone Co., Ltd.) was used instead of Tego Rad 2700 (5-A), which is a reactive silicone surfactant, Except for using 0.48 part of propylene glycol monomethyl ether acetate (5-B) and 53.77 parts of propylene glycol monomethyl ether acetate (6-B) as a solvent.

Comparative Example  3

In the preparation of the colored photosensitive resin composition in Example 1, polyether-modified silicone oil SH8400 (manufactured by Toray Silicone Co., Ltd.) was used instead of Tego Rad 2700 (5-A), which is a reactive silicone surfactant, Except for using 0.96 part of propylene glycol monomethyl ether acetate (5-B) and 53.29 parts of propylene glycol monomethyl ether acetate (6-B) as a solvent.

Comparative Example  4

In the preparation of the colored photosensitive resin composition in Example 1, polyether-modified silicone oil SH8400 (manufactured by Toray Silicone Co., Ltd.) was used instead of Tego Rad 2700 (5-A), which is a reactive silicone surfactant, Except for using 0.48 part of the above-mentioned propylene glycol monomethyl ether acetate (5-B), 0.48 part of Megafox (registered trademark) F475 (5-C) and 52.81 parts of propylene glycol monomethyl ether acetate (6-B) Respectively.

The components and compositions of the colored photosensitive resin compositions prepared in the above Examples and Comparative Examples are shown in Table 1 below. At this time, the content of each component represents the mass part.

division Example Comparative Example One 2 3 4 One 2 3 4 coloring agent 1-A 3.55 3.55 3.55 3.55 3.55 3.55 3.55 3.55 Alkali-soluble resin 2-A 9.57 9.57 9.57 9.57 9.57 9.57 9.57 9.57 Photopolymerizable compound 3-A 2.79 2.79 2.79 2.79 2.79 2.79 2.79 2.79 Photopolymerization initiator 4-A 0.74 0.74 0.74 0.74 0.74 0.74 0.74 0.74 Initiation of photopolymerization
Supplements 4-B 0.37 0.37 0.37 0.37 0.37 0.37 0.37 0.37 Interface
Activator 5-A 0.24 0.48 0.96 0.96 - - - - 5-B - - - - 0.24 0.48 0.96 0.96 5-C - - - 0.48 - - - 0.48 solvent 6-A 26.39 26.39 26.39 26.39 26.39 26.39 26.39 26.39 6-B 54.01 53.77 53.29 52.81 54.01 53.77 53.29 52.81 additive
7-A 1.08 1.08 1.08 1.08 1.08 1.08 1.08 1.08 7-B 1.24 1.24 1.24 1.24 1.24 1.24 1.24 1.24 7-C 0.02 0.02 0.02 0.02 0.02 0.02 0.02 0.02

The components in Table 1 are as follows.

(1-A) Colorant: C.I. Pigment Blue 15: 6

(2-A) Alkali-soluble resin: copolymer of methacrylic acid and benzyl methacrylate (the molar ratio of methacrylic acid unit to benzyl methacrylate unit was 27:73, acid value was 83, weight average molecular weight was 18,000)

(3-A) Photopolymerizable compound: dipentaerythritol hexaacrylate

(4-A) Photopolymerization initiator: 2-methyl-2-morpholino-1- (4-methylthiophenyl) propan-

(4-B) Photopolymerization initiator: 4,4'-bis (diethylamino) benzophenone

(5-A) Surfactant: Tego Rad 2700 (Degussa)

(5-B) Surfactant: polyether-modified silicone oil SH8400 (manufactured by Toray Silicone Co., Ltd.)

(5-C) Surfactant: Megafox (registered trademark) F475 (manufactured by Dainippon Ink and Chemicals, Inc.)

(6-A) Solvent: ethyl 3-ethoxypropionate

(6-B) Solvent: Propylene glycol monomethyl ether acetate

(7-A) Additive: Polyester-based pigment dispersant

(7-B) Additive: Epoxy resin (SUMI-EPOXY ESCN-195XL) which is a thermal cross-

(7-C) Additive: Methacryloxypropyltrimethoxysilane as an adhesion promoter

Test Example

The occurrence of development unevenness according to the amount of exposure of the color filters prepared in Examples 1 to 4 and Comparative Examples 1 to 4 was measured and evaluated in the following manner, and the results are shown in Table 2 below.

* Measured under the conditions of exposure amounts of 100, 60 and 40 mJ / cm 2, respectively.

* Evaluation standard

- No stains on the substrate: ○

- On the substrate, development stain is weak: △

- Heavy stain on substrate: X

division Example Comparative Example One 2 3 4 One 2 3 4 Exposure dose
(mJ / cm 2) 100 100 100 100 100 100 100 100 Stain ○ ○ ○ ○ △ ○ ○ ○ Exposure dose
(mJ / cm 2) 60 60 60 60 60 60 60 60 Stain ○ ○ ○ ○ △ △ ○ ○ Exposure dose
(mJ / cm 2) 40 40 40 40 40 40 40 40 Stain △ ○ ○ ○ X X △ △

As shown in Table 2, the color filters prepared using the colored photosensitive resin compositions of Examples 1 to 4 including the reactive silicone surfactants according to the present invention exhibited a phenomenon even under a developing condition that the exposure amount was as low as 40 mJ / No stain occurred.

On the other hand, the color filters prepared by using the colored photosensitive resin compositions of Comparative Examples 1 to 4 including the polyether-modified silicone oil did not cause developing unevenness under the developing condition with a high exposure amount, Under the conditions, development unevenness occurred.

Accordingly, by applying the colored photosensitive resin composition containing the reactive silicone surfactant of the present invention, it is possible to improve productivity and yield in the process, and to form a high quality color filter pattern free from development unevenness and pattern errors.

1A to 1C are process diagrams for producing a color filter using a colored photosensitive resin composition according to an embodiment of the present invention.

Description of the Related Art [0002]

10: substrate 11: color layer 11R: color layer (red)

20: Photomask 30: Light

Claims (7)

coloring agent; Alkali-soluble resins; Photopolymerizable compounds; A photopolymerization initiator; solvent; A reactive silicone surfactant represented by the following formula (1); And at least one surfactant selected from the group consisting of silicone surfactants having a fluorine atom, silicone surfactants and fluorine surfactants. [Chemical Formula 1]

Wherein R ₁ is an ester group or an alkyl group having 1 to 20 carbon atoms, R ₂ , R ₃ and R ₄ are each independently hydrogen or an alkyl group having 1 to 10 carbon atoms, and 1, m and n are integers from 1 to 20 . The colored photosensitive resin composition according to claim 1, wherein the reactive silicone surfactant is a reactive silicone surfactant represented by the following formula: (2)

Wherein R ₁ is an ester group or an alkyl group having 1 to 20 carbon atoms, and 1, m and n are an integer of 1 to 20. The colored photosensitive resin composition according to claim 1, wherein the reactive silicone surfactant is contained in an amount of 0.001 to 14% by mass based on 100% by mass of the total solid content in the colored photosensitive resin composition. The colored photosensitive resin composition according to claim 1, wherein the reactive silicone surfactant is contained in an amount of 0.1 to 10% by mass based on 100% by mass of the total solid content in the colored photosensitive resin composition. delete A color filter comprising a color layer formed by applying a colored photosensitive resin composition on a substrate and exposing and developing the color filter in a predetermined pattern, wherein the colored photosensitive resin composition is the color filter according to any one of claims 1 to 4 ≪ / RTI > A liquid crystal display device comprising the color filter of claim 6.

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