KR20170104311A - Colored photosensitive resin composition and color filter using the same - Google Patents

Abstract

The present invention relates to a colored photosensitive resin composition comprising a layered clay compound modified by a silane-based compound, a color filter manufactured by using the composition and an organic light emitting diode. The colored photosensitive resin composition comprising a surface-modified layered clay compound has excellent brightness, solvent resistance, etc. and has excellent oxygen and moisture barrier properties.

Description

TECHNICAL FIELD [0001] The present invention relates to a colored photosensitive resin composition and a color filter using the colored photosensitive resin composition.

The present invention relates to a colored photosensitive resin composition, a color filter manufactured using the same, and an organic light emitting diode.

BACKGROUND ART Color filters are widely used for various display devices such as an image pickup device, a liquid crystal display device (LCD), and an organic light emitting diode (OLED), and the application range thereof is rapidly expanding. The color filter used in the above-mentioned display device may be a coloring pattern of three colors of red, green and blue, or a coloring pattern of yellow, magenta, and cyan And is formed of three coloring patterns.

The coloring pattern of each of the color filters is generally formed using a colored photosensitive resin composition comprising a coloring agent such as pigment or dye, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent. The coloring pattern processing using the colored photosensitive resin composition is usually performed by a lithography process.

2. Description of the Related Art Recently, as a flat panel display device proposed to replace a conventional cathode ray tube display device, a liquid crystal display device, a field emission display device, a plasma display device, A display panel (Plasma Display Panel) and an organic light-emitting diode (OLED) display.

In the organic light emitting diode, the organic light emitting diode provided in the display panel has a high luminance and a low operating voltage characteristic and is self-emitting type, so that the contrast ratio is large and an ultra-thin display can be realized. Is applied to the field.

However, OLEDs are extremely vulnerable to moisture, such as peeling of an interface between a metal electrode and an organic EL layer due to moisture, or degradation of a metal electrode due to reaction with oxygen and moisture, thereby lowering the yield.

The photocurable resin composition, which is generally used in the manufacture of color filters, is low in water or oxygen barrier properties, and it is difficult to prevent defect occurrence and yield deterioration when a color filter for OLED is manufactured.

SUMMARY OF THE INVENTION The present invention has been made in order to solve the problems of the prior art,

It is an object of the present invention to provide a colored photosensitive resin composition containing a layered clay compound modified with a silane compound and having excellent mechanical strength, oxygen barrier property and moisture barrier property.

Another object of the present invention is to provide an OLED having improved quality using a color filter manufactured using the colored photosensitive resin composition.

According to the present invention,

The present invention provides a colored photosensitive resin composition comprising a colorant, a binder resin, a photopolymerizable compound, a photopolymerization initiator, a layered clay compound modified with a silane compound, and a solvent.

In addition,

And a color filter manufactured using the colored photosensitive resin composition.

In addition,

And an organic light emitting diode including the color filter.

The colored photosensitive resin composition of the present invention containing the surface-modified layered clay compound can provide an excellent effect of excellent oxygen and moisture barrier properties as well as excellent luminance, solvent resistance and the like.

In addition, since the color filter manufactured using the composition of the present invention has the above-described characteristics, it can be preferably used for manufacturing a color filter for OLED that is sensitive to moisture and moisture.

1 is a flowchart schematically showing a method for evaluating the occurrence of water stains in Experimental Example 2 of the present invention.

The inventors of the present invention have been studying a colored photosensitive resin composition suitable for use in an OLED which is excellent in oxygen and moisture barrier properties and vulnerable to moisture, and has found that a coloring agent, a binder resin, a photopolymerizable compound, a photopolymerization initiator, The present inventors have found that a colored photosensitive resin composition comprising a compound and a solvent provides such an effect and completed the present invention.

According to the present invention,

The present invention provides a colored photosensitive resin composition comprising a colorant, a binder resin, a photopolymerizable compound, a photopolymerization initiator, a layered clay compound modified with a silane compound, and a solvent. The composition is excellent in mechanical strength, excellent in oxygen barrier property and moisture barrier property, and can be advantageously applied to the production of an OLED which is vulnerable to moisture.

Each component constituting the colored photosensitive resin composition of the present invention will be described below.

(A) Colorant

The colorant contained in the colored photosensitive resin composition of the present invention is a component capable of color development so as to produce a pattern having a desired hue. The colorant is not particularly limited, and a color tone can be selected depending on the use of the color filter to be produced.

The colorant may specifically include one or more selected from pigments and dyes.

Pigment

The pigment may be an organic pigment or an inorganic pigment generally used in the art. The organic pigments or inorganic pigments may be various pigments used in printing ink, ink jet ink, etc. Specific examples thereof include water-soluble azo pigments, insoluble azo pigments, phthalocyanine pigments, quinacridone pigments, isoindolinone pigments An anthanthrone pigment, an indanthrone pigment, an anthraquinone pigment, an anthraquinone pigment, an anthanthrone pigment, an anthanthrone pigment, an indanthrone pigment, an anthanthrone pigment, Pigments, pyranthrone pigments, and diketopyrrolopyrrole pigments.

Examples of the inorganic pigments include metallic compounds such as metal oxides and metal complex salts. Specific examples of the inorganic pigments include oxides of metals such as iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony and carbon black Or composite metal oxides.

Particularly, the above-mentioned pigments are specifically classified into pigments in the Society of Dyers and Colors Publications, and more specifically, pigments having a color index (CI) number as described below , But are not limited thereto.

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

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

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

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

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

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

C.I. Pigment Brown 28;

C.I. Pigment Black 1 and 7, etc .;

The above-exemplified pigments may be selected from one or more of them so as to be suitable for the desired chromaticity.

The exemplified C.I. Among the pigment pigments, C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, C.I. Pigment Yellow 185, C.I. Pigment Orange 38, C.I. Pigment Red 122, C.I. Pigment Red 166, C.I. Pigment Red 177, C.I. Pigment Red 208, C.I. Pigment Red 242, C.I. Pigment Red 254, C.I. Pigment Red 255, C.I. Pigment Violet 23, C.I. Pigment Blue 15: 3, Pigment Blue 15: 6, C.I. Pigment Green 7, C.I. Pigment Green 36 and C.I. Pigment Green 58 can be preferably used.

dyes

The dye can be used without limitation as long as it has solubility in an organic solvent. However, it is preferable to use a dye having solubility in an organic solvent and securing reliability such as solubility in an alkali developing solution, heat resistance and solvent resistance.

Examples of the dye include acid dyes having an acidic group such as sulfonic acid and carboxylic acid, salts of an acidic dye and a nitrogen-containing compound, sulfonamides of an acidic dye and derivatives thereof, and azo, Based acid dyes and derivatives thereof. Preferably, the dye is a compound classified as a dye in a color index (published by The Society of Dyers and Colourists), or a known dye described in a dyeing note (coloring yarn).

Specific examples of the dye include,

C.I. As a solvent dye

C.I. Solvent Red 8, 45, 49, 89, 111, 122, 125, 130, 132, 146 and 179 and the like;

C.I. Solvent Blue 5, 35, 36, 37, 44, 45, 59, 67 and 70, etc .;

C.I. Solvent Violet 8, 9, 13, 14, 36, 37, 47 and 49 and the like;

C.I. Solvent Yellow 4, 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99 and 162;

C.I. Solvent Orange 2, 7, 11, 15, 26, and 56;

C.I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34 and 35.

C.I. Solvent dye having excellent solubility in an organic solvent. Solvent Yellow 14, 16, 21, 56, 79, 93, 151; C.I. Solvent Red 8, 49, 89, 111, 122, 132, 146, 179; C.I. Solvent Orange 41, 45, 62; C.I. Solvent Blue 35, 36, 44, 45, 70; And C.I. Solvent Violet 13, and among these, C.I. Solvent Yellow 21, 79; C.I. Solvent Red 8, 122, 132; C.I. Solvent Orange 45, 62 is more preferred.

Also, C.I. As an acid dye

CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 34, 35, 37, 42, 44, 50, 51, 52, 57, 66, 73, 80, 87, 88 , 91, 92, 94, 97, 103, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 158, 176, 182, 183, 198, 206, 211, 215, 216, 217 , 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 195, 308, 312, 315, 316, 339, 341, 345, 346, 349 , 382, 383, 394, 401, 412, 417, 418, 422, and 426;

CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112 , 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184 , 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242,

CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169 and 173;

CI Acid Blue 1, 7, 9, 15, 18, 23, 25, 27, 29, 40, 42, 45, 51, 62, 70, 74, 80, 83, 86, 87, 90, , 112, 113, 120, 129, 138, 147, 150, 158, 171, 182, 192, 210, 242, 243, 256, 259, 267, 278, 280, 285, 290, 296, 315, , 335 and 340, etc .;

C.I. Acid Violet 6B, 7, 9, 17, 19 and 66 and the like;

Dyes such as C.I. Acid Green 1, 3, 5, 9, 16, 25, 27, 50, 58, 63, 65, 80, 104, 105, 106 and 109.

C.I. Acid Yellow 42 having excellent solubility in organic solvents in C.I. acid dye; C.I. Acid Red 92; C. I. Acid Blue 80, 90; C.I. Acid Violet 66; Or C. I. Acid Green 27 is preferred.

As a C.I. direct dye,

CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211 , 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246 and 250;

CI Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129 , 136, 138 and 141, etc .;

C.I. Direct Orange 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106 and 107;

CI Direct Blue 38, 44, 57, 70, 77, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113 , 114, 115, 117, 119, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 166, 167, 170, 171, 172, 173, 188, 189 , 190, 192, 193, 194, 196, 198, 199, 200, 207, 209, 210, 212, 213, 214, 222, 228, 229, 237, 238, 242, 243, 244, 245, 247, 248 , 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, and 293;

C. I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103 and 104;

Dyes such as C.I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79 and 82

As C.I. modantoic dyes,

C.I. Modetto Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62 and 65;

CI Modal Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 30, 32, 33, 36, 37, 41, 43, 45, 46, 48, 53, 56, 63, 71, 74, 85, 86, 88, 90, 94 and 95;

C. I. Modatto Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47 and 48;

CI Modanito Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 43, 44, 48, 49, 53, 61, 74, 77, 83 and 84, etc .;

C. I. Modanth violet 1, 2, 4, 5, 7, 14, 22, 24, 30, 31, 32, 37, 40, 41, 44, 45, 47, 48, 53 and 58;

Dyes such as C.I. Modatto Green 1, 3, 4, 5, 10, 15, 19, 26, 29, 33, 34, 35, 41, 43 and 53.

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

The pigment is preferably a pigment dispersion in which the particle diameter of the pigment is uniformly dispersed. As an example of a method for uniformly dispersing the particle diameter of the pigment, there is a method of dispersing the pigment by adding a pigment dispersant. According to the method, a pigment dispersion in which the pigment is uniformly dispersed in a solution can be obtained .

Pigment dispersant

The pigment dispersant is added for the purpose of deagglomeration and stability of the pigment. Specific examples of the pigment dispersant include a cationic surfactant, an anionic surfactant, a nonionic surfactant, a positive surfactant, a polyester surfactant, and a polyamine surfactant. These surfactants may be used singly or in combination of two or more.

It is also preferable to include an acrylate-based dispersant (hereinafter referred to as an acrylate-based dispersant) containing butyl methacrylate (BMA) or N, N-dimethylaminoethyl methacrylate (DMAEMA). Examples of commercially available acrylate dispersants include DISPER BYK-2000, DISPER BYK-2001, DISPER BYK-2070 and DISPER BYK-2150. The acrylate dispersants may be used alone or in combination of two or more. .

As the pigment dispersant, other resin type pigment dispersants other than the acrylate dispersant may be used. The other resin type pigment dispersing agent may be a known resin type pigment dispersing agent, especially a polycarboxylic acid ester such as polyurethane, polyacrylate, unsaturated polyamide, polycarboxylic acid, polycarboxylic acid (partial) Amine salts of polycarboxylic acids, alkylamine salts of polycarboxylic acids, polysiloxanes, long chain polyaminoamide phosphate salts, esters of hydroxyl group-containing polycarboxylic acids and their modified products, or free ) Oil-based dispersants such as amides formed by reaction of a polyester having a carboxyl group with poly (lower alkyleneimine) or salts 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, and phosphate esters.

DISPER BYK-161, DISPER BYK-162, DISPER BYK-163 and DISPER BYK-160 available from BYK (Big) Chemie are commercially available as the above-mentioned resin type pigment dispersant. BYK-164, DISPER BYK-166, DISPER BYK-171, DISPER BYK-182, DISPER BYK-184; EFKA-4060, EFKA-4060, EFKA-4055, EFKA-4055, EFKA-4055, EFKA-4020, EFKA-4015, EFKA-4060, EFKA- 4330, EFKA-4400, EFKA-4406, EFKA-4510, EFKA-4800; SOLSPERS-24000, SOLSPERS-32550, NBZ-4204/10 from Lubirzol; Hinoact T-6000, Hinoact T-7000, Hinoact T-8000; available from Kawaken Fine Chemicals; AJISPUR PB-821, Ajisper PB-822, Ajisper PB-823 manufactured by Ajinomoto; FLORENE DOPA-17HF, fluorene DOPA-15BHF, fluorene DOPA-33, and fluorene DOPA-44 are trade names of Kyoeisha Chemical Co.,

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

The content of the pigment dispersant is preferably 5 to 60 parts by weight, more preferably 15 to 50 parts by weight, based on 100 parts by weight of the solid content of the pigment. If the content of the pigment dispersant is less than 5 parts by weight on the basis of the above-mentioned criteria, it may be difficult to atomize the pigment or cause problems such as gelation after dispersion, and if it exceeds 60 parts by weight, the viscosity may be increased.

The colorant is preferably contained in an amount of 3 to 60% by weight, and more preferably 5 to 55% by weight based on the total weight of the solid content of the colored photosensitive resin composition. When the content of the coloring agent is 3 to 60% by weight on the basis of the above criteria, the color density when the color filter is produced is sufficient and the polymer can be contained in the required amount in the colored photosensitive resin composition, Can be formed.

(B) binder resin

The binder resin contained in the colored photosensitive resin composition of the present invention usually has reactivity and alkali solubility due to the action of light or heat and acts as a dispersion medium of the colorant. The binder resin generally used in the art can be used without particular limitation as long as it acts as a binder resin for the colorant and is soluble in the alkaline developer used in the development step for the production of the color filter.

The binder resin includes, for example, a copolymer of a carboxyl group-containing monomer and another monomer copolymerizable with the monomer.

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

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

 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 and citraconic anhydride. The unsaturated polycarboxylic acid may also be a mono (2-methacryloyloxyalkyl) ester thereof, for example, mono (2-acryloyloxyethyl) succinate, mono (2-methacryloyloxy Ethyl), phthalic acid mono (2-acryloyloxyethyl) and phthalic acid mono (2-methacryloyloxyethyl). The unsaturated polycarboxylic acid may be mono (meth) acrylate of the both terminal dicarboxylic polymer, and examples thereof include ω-carboxypolycaprolactone monoacrylate and ω-carboxypolycaprolactone monomethacrylate. have.

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

Examples of the other monomer 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, dicyclopentadiethyl methacrylate, 2-hydroxy-3-phenoxy Acrylate, 2-hydroxy-3-phenoxypropyl methacrylate, unsaturated carboxylic acid esters such as glycerol monoacrylate and glycerol monomethacrylate; Aminoethyl methacrylate, 2-aminoethyl methacrylate, 2-dimethylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate, 2-aminopropyl acrylate, 2-aminopropyl methacrylate, 2- Unsaturated carboxylates such as methyl acrylate, ethyl acrylate, propyl methacrylate, isopropyl acrylate, isopropyl acrylate, isopropyl acrylate, isopropyl acrylate, isopropyl acrylate, Acid amino alkyl esters; Unsaturated carboxylic acid glycidyl esters such as glycidyl acrylate and glycidyl methacrylate; Carboxylic acid vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate and vinyl benzoate; Unsaturated ethers such as vinyl methyl ether, vinyl ethyl ether and allyl glycidyl ether; Vinyl cyanide compounds such as acrylonitrile, methacrylonitrile,? -Chloroacrylonitrile and vinylidene cyanide; Unsaturated amides such as acrylamide, methacrylamide,? -Chloroacrylamide, N-2-hydroxyethyl acrylamide and N-2-hydroxyethyl methacrylamide; Unsaturated imides such as maleimide, N-phenylmaleimide and N-cyclohexylmaleimide; Aliphatic conjugated dienes such as 1,3-butadiene, isoprene and chloroprene; And a monoacryloyl group or monomethacryloyl group at the end of the polymer molecular chain of polystyrene, polymethyl acrylate, polymethyl methacrylate, poly-n-butyl acrylate, poly-n-butyl methacrylate, And the like. These monomers may be used alone or in combination of two or more.

The binder resin preferably has an acid value of 20 to 200 mgKOH / g. When the acid value of the binder resin is within the above range, the solubility in the developer is improved to easily dissolve the non-exposed portion and increase the sensitivity, and as a result, the pattern of the exposed portion remains during development to improve the film remaining 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 binder resin preferably has a weight average molecular weight (hereinafter simply referred to as "weight average molecular weight") in terms of polystyrene measured by gel permeation chromatography (GPC; tetrahydrofuran as an elution solvent) of 3,000 to 200,000, It is preferably 5,000 to 100,000. When the weight average molecular weight of the binder resin is within the above range, it is preferable because the hardness of the coating film is improved, the residual film ratio is high, the solubility of the non-exposed portion in the developer is excellent, and the resolution tends to be improved.

The molecular weight distribution (weight average molecular weight (Mw) / number average molecular weight (Mn)) of the binder resin is preferably 1.5 to 6.0, more preferably 1.8 to 4.0. When the molecular weight distribution (weight-average molecular weight (Mw) / number-average molecular weight (Mn)) is 1.5 to 6.0, development is preferable.

The binder resin is preferably contained in an amount of 5 to 85% by weight, and more preferably 10 to 70% by weight based on the total weight of the solid components in the colored photosensitive resin composition. If the content of the binder resin is within the above range, solubility in a 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 the property tends to be good.

(C) Photopolymerization  compound

The photopolymerizable compound contained in the colored photosensitive resin composition of the present invention is a compound capable of polymerizing under the action of light and a photopolymerization initiator described later, and specific examples thereof include monofunctional monomers, bifunctional monomers and polyfunctional monomers.

Specific examples of the monofunctional monomer include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate and N- Ralidon, and the like.

Specific examples of the bifunctional monomer include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) , Bis (acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di (meth) acrylate.

Specific examples of other polyfunctional monomers include trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) And pentaerythritol hexa (meth) acrylate.

Of these, polyfunctional monomers having two or more functional groups can be preferably used as the photopolymerizable compound.

The photopolymerizable compound is preferably contained in an amount of 5 to 50% by weight, more preferably 7 to 45% by weight based on the total weight of the solid content in 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 tends to be favorable.

(D) Light curing Initiator

The photopolymerization initiator contained in the colored photosensitive resin composition of the present invention is a compound which generates a radical capable of initiating polymerization of the photopolymerizable compound described above by exposure to visible light, ultraviolet light, far ultraviolet light, electron beam, X-ray or the like.

As long as the purpose of the present invention is not impaired, the type of the alkali-soluble resin and the photopolymerizable compound which can be used in the art is not particularly limited. Typical examples include oxime compounds, acetophenone compounds, benzoin compounds, benzophenone compounds, nonimidazole compounds, thioxanthone compounds, triazine compounds, and anthracene compounds. And it is possible to select at least one of them. Among them, when the polymerization characteristics, the initiation efficiency and the absorption wavelength are considered, it is more preferable to use an oxime compound.

Examples of the oxime compounds include o-ethoxycarbonyl- alpha -oximimino-1-phenylpropan-1-one, 1- [9-ethyl-6- (2-methylbenzoyl) -9H- (Z) -2 - ((benzoyloxy) imino) -1- (4- (phenylthio) phenyl) octan-1-one, (E) -1- (((1- (9-ethyl-6- (2-methylbenzoyl) -9H-carbazol- (((1- (6- (4 - ((2,2-dimethyl-1,3-dioxolan-4- yl) methoxy) -2-methylbenzoyl) -9- -Yl) ethyl) amino) oxy) ethanone, and commercially available products include, but are not limited to, OXE-01 and OXE-02 from BASF.

Specific examples of the acetophenone-based compound include diethoxyacetophenone, 2-methyl-2-morpholino-1- (4-methylthiophenyl) propan- 2-methyl-1-phenylpropan-1-one, benzyldimethylketal, 2-hydroxy-2-methyl-1- [4- Phenylpropane-1-one, 1-hydroxycyclohexyl phenyl ketone and 2-hydroxy-2-methyl-1- [4- (1-methylvinyl) phenyl] propane- 1-one oligomers and the like.

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 methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3 ', 4,4'-tetra Oxycarbonyl) 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 and 1-chloro- 4-propanedioxanthone, and the like.

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

Examples of the anthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, etc. .

The photopolymerization initiator may be used in combination with a photopolymerization initiator. The photopolymerization initiator may be used for promoting polymerization of a photopolymerizable compound initiated by a photopolymerization initiator. Specific examples thereof include an amine compound and an alkoxyanthracene compound.

Specific examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate , 4-dimethylaminobenzoic acid 2-ethylhexyl, N, N-dimethylparatoluidine, 4,4'-bis (dimethylamino) benzophenone (collectively, Michler's ketone), 4,4'- ) Benzophenone, and 4,4'-bis (ethylmethylamino) benzophenone. Of these, 4,4'-bis (diethylamino) benzophenone is more preferable.

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

The photopolymerization initiator may be a commercially available product such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) or the like.

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

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, per mol of the photopolymerization initiator. When the photopolymerization initiator is contained within the above-mentioned content range, the sensitivity of the colored photosensitive resin composition is further improved, and the productivity of the color filter formed using the composition tends to be improved.

The photopolymerization initiator is preferably contained in an amount of 1 to 20% by weight, and more preferably 5 to 15% by weight based on the total weight of the solid content in the colored photosensitive resin composition. When the content of the photopolymerization initiator is within the above-mentioned range, 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.

(E) Silane system  As the compound Reformed Layered clay compound

The layered clay compound modified with the silane compound contained in the colored photosensitive resin composition of the present invention is sufficiently dispersed in the composition to act as moisture and oxygen barrier agent, thereby providing excellent moisture and oxygen barrier properties.

The layered clay compound may be selected from the group consisting of montmorillonite, bentonite, kaolinite, mica, hectorite, fluorohectorite, saponite, beidalite, nontronite, stevensite, vermiculite, hallosite, volkonskoite, suconite, magadite, and kenya It may be preferable to use one or more kinds selected from kenyalite.

More preferably, the layered clay compound may be an organic layered clay compound in which an organic substance is interposed between the layered clay compound layers.

The organic material may be selected from the group consisting of quaternary ammonium, phosphonium, maleate, succinate, acrylate, benzylic hydrogen, and oxazoline. But it is not limited to these organic materials.

Also, it is preferable that the organic matter content is 1 to 10% by weight based on the total weight of the organophilic layered clay compound.

Commercial products of the organically modified layered clay compounds include Cloisite 10A (C10A), Cloisite 15A (C15A), Cloisite 20A (C20A), Cloisite 25A (C25A) and Cloisite 30B C30B), but are not limited thereto.

C25A is a clay modified with dimethyl, hydrogenated tallow, 2-ethylhexyl quaternary ammonium, and having a modifier concentration of 95 meq / 100 g.

The silane compound may more preferably be a siloxane compound containing a siloxane (Si-O) group, and may include an epoxy group or a sulfide group to improve reactivity. Specific examples include 1 (1) selected from glycidoxypropyltrimethoxy silane (GPS) and bis [(3-triethoxysilylpropyl) tetrasulfide], bis It may include, but is not limited to, species.

The layered clay compound modified with the silane compound in the present invention can be prepared by reacting the silane compound with the layered clay compound. For example, the surface of the layered clay compound can be modified with a silane-based compound through the reaction of the silane-based compound with the Si-OH of the layered clay compound.

As one example, moreover, Si-OH, which is a hydrophilic group, remains on the surface of the C25A. Epoxy-Clay, which is a surface-modified layered clay compound, induces a reaction between Si-OH and an epoxy group of Glycidoxypropyltrimethoxy silane (GPS) And can be used to induce a chemical bond with a polymer matrix.

The layered clay compound modified with the silane compound exhibits excellent moisture and oxygen-blocking effect as it is minutely peeled into the composition. It can be judged that the layered clay compound which is finely peeled off in the composition forms a blocking film, thereby improving the barrier properties and mechanical properties of the composition itself.

More specifically, water molecules permeating through the color coat pass through the impermeable clay layer without passing through. As a result, the permeation time of the gas increases, so that permeation of gas and moisture is difficult, and the permeability is reduced. Further, the degree of curing of the color resist can be increased to help improve the reliability.

When the layered clay compound modified with the silane compound of the present invention is used as the clay compound, the contact area between the polymer chain and the layered clay compound is maximized to maximize the ability to inhibit gas and liquid permeation.

The layered clay compound modified with the silane compound may have a nano-sized size in terms of improving moisture and oxygen barrier properties.

The layered clay compound modified with the silane compound is preferably contained in an amount of 0.1 to 10% by weight, and more preferably 2 to 5% by weight based on the total weight of the solid content of the colored photosensitive resin composition. If the content of the modified layered clay compound is less than 0.1% by weight, the oxygen and moisture barrier properties are insignificant. If the modified layered clay compound exceeds 10% by weight It is not preferable because there is a problem of lowering the luminance.

(F) Solvent

The solvent contained in the colored photosensitive resin composition of the present invention may be any organic solvent ordinarily used in the art, provided that it is effective in dissolving other components contained in the colored photosensitive resin composition. Examples of the solvent include, but are not limited to, ethers, acetates, aromatic hydrocarbons, ketones, alcohols or ester solvents.

Specific examples of the ether solvents include ethylene glycol monoalkyl ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, and ethylene glycol monobutyl ether;

Diethylene glycol dialkyl ethers such as diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether and diethylene glycol dibutyl ether; And the like.

Specific examples of the acetate solvents include ethylene glycol alkyl ether acetates such as methyl cellosolve acetate and ethyl cellosolve acetate; And

Alkylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxybutyl acetate and methoxypentyl acetate; And the like.

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

Specific examples of the ketone solvent include methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone, and cyclohexanone.

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

 Specific examples of the ester solvents include ethyl 3-ethoxypropionate and methyl 3-methoxypropionate; And cyclic esters such as? -Butyrolactone.

The solvent is preferably an organic solvent having a boiling point of 100 ° C to 200 ° C in terms of coatability and dryness, more preferably an alkylene glycol alkyl ether acetate, a ketone, ethyl 3-ethoxypropionate, Propylene glycol monomethyl ether acetate, cyclohexanone, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, and the like can be given. Among them, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, have. These solvents may be used alone or in combination of two or more.

The content of the solvent is preferably 60 to 90% by weight, more preferably 70 to 85% by weight based on the total weight of the colored photosensitive resin composition of the present invention. When the content of the solvent is within the range of 60 to 90% by weight on the basis of the above-mentioned criteria, when the solvent is applied by a coating device such as a roll coater, a spin coater, a slit and spin coater, a slit coater (sometimes referred to as a die coater) Is preferable because it tends to be good.

(G) Additive

It is also possible that the colored photosensitive composition of the present invention further contains other additives according to the needs of those skilled in the art, in addition to the above-mentioned components, so long as the objects of the present invention are not impaired.

The additive may be optionally added, for example, a filler, another polymer compound, a pigment dispersant, a curing agent, an adhesion promoter, an antioxidant, an ultraviolet absorber or an aggregation inhibitor, Can be selected and used.

Specific examples of the filler include glass, silica and alumina.

Specific examples of the other polymer compound include a curable resin such as epoxy resin and maleimide resin, a thermoplastic resin such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl acrylate, polyester, polyurethane and the like .

As the pigment dispersant, a commercially available surfactant can be used, and examples thereof include surfactants such as silicone, fluorine, ester, cationic, anionic, nonionic, and amphoteric surfactants. These may be used alone or in combination of two or more. Examples of the surfactant include polyoxyethylene alkyl ethers, polyoxyethylene alkylpethers, polyethylene glycol diesters, sorbitan fatty esters, fatty acid modified polyesters, tertiary amine modified polyurethanes (Manufactured by Shin-Etsu Chemical Co., Ltd.), POLYFLOW (manufactured by Kyoeisha Chemical Co., Ltd.), EFTOP (manufactured by TOKEM PRODUCTS CO., LTD.), And polyethyleneimine, (Manufactured by Dainippon Ink and Chemicals, Inc.), Flourad (manufactured by Sumitomo 3M Limited), Asahi guard, Surflon (manufactured by Asahi Glass Co., Ltd.), Sol SOLSPERSE (manufactured by Genene), EFKA (manufactured by EFKA Chemical), PB 821 (manufactured by Ajinomoto), and the like.

TS-4440, TSF-4445, TSF-4446, etc. of GE Toshiba Silicones such as DC3PA, DC7PA, SH11PA, SH21PA and SH-8400 from Dow Corning Toray Silicone Co., TSF-4460 and TSF-4452. Examples of the fluorine-based surfactant include Megapis F-470, F-471, F-475, F-482 and F-489 commercially available from Dainippon Ink and Chemicals, Incorporated.

The above-exemplified surfactants may be used alone or in combination of two or more.

The curing agent is used for increasing the curing depth and mechanical strength, and specific examples thereof include an epoxy compound, a polyfunctional isocyanate compound, a melamine compound and an oxetane compound.

Specific examples of the adhesion promoter include vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2 (aminoethyl) - (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3- Trimethoxysilane, and the like.

Specific examples of the antioxidant include 2,2'-thiobis (4-methyl-6-t-butylphenol) and 2,6-di-t-butyl-4-methylphenol.

Specific examples of the ultraviolet absorber include 2- (3-tert-butyl-2-hydroxy-5-methylphenyl) -5-chlorobenzothiazole and alkoxybenzophenone.

Specific examples of the anti-aggregation agent include sodium polyacrylate and the like.

The additive may be contained in an amount of preferably 0.01 to 10% by weight, more preferably 0.05 to 3% by weight based on the total weight of the solid content in the colored photosensitive resin composition.

<Color filter>

According to another aspect of the present invention, there is provided a color filter comprising a color layer formed by applying a colored photosensitive resin composition according to the present invention on a substrate, and exposing and developing the color filter in a predetermined pattern, to provide.

The color filter of the present invention comprises a substrate and a coloring pattern made of the colored photosensitive resin composition of the present invention on the substrate. The substrate may be made of a transparent material having sufficient strength and supporting force for the stability of the color filter. Preferably, a glass having excellent chemical stability and high strength can be used.

That is, the present invention provides a color filter including a coloring pattern made of the colored photosensitive resin composition of the present invention, and the manufacturing method of the color filter can use a conventional method well known in the art.

< Organic light emitting diode >

The present invention also provides an organic light emitting diode including the color filter. The organic light emitting diode includes a structure known to those skilled in the art, except that the organic light emitting diode is provided with the color filter of the present invention. That is, the present invention includes an organic light emitting diode to which the color filter of the present invention is applied.

Hereinafter, the present invention will be described in more detail with reference to examples. However, it should be understood that the following examples are illustrative of the present invention, and the present invention is not limited by the following examples, and various modifications and changes may be made without departing from the scope of the present invention. The scope of the present invention will be determined by the technical idea of the following claims.

< Manufacturing example >

Manufacturing example  1. Preparation of Pigment Dispersion Composition (M1)

C.I. 13.5 parts by weight of Pigment Blue 15: 6, 5.0 parts by weight of DISPERBYK-2001 (manufactured by BYK) as a pigment dispersant, 61.5 parts by weight of propylene glycol monomethyl ether acetate as a solvent and 4 parts by weight of 4-hydroxy- Were mixed and dispersed by a bead mill for 12 hours to prepare a pigment dispersion composition.

Manufacturing example  2. Silane system  As the compound Reformed  Manufacture of Epoxy-Clay

As the layered clay compound, Cloisite 25A (C25A) of Southern Clay Product (USA) was used. The C25A was a clay modified with dimethyl, hydrogenated tallow, 2-ethylhexyl quaternary ammonium, and modifier concentration ) Is 95meq / 100g.

3.5 g of glycidoxypropyltrimethoxy silane was hydrolyzed in an aqueous solution of pH 4.0 for 4 hours and then a mixed solution (200 ml) of ethanol (90 wt%) / distilled water (10 wt% . Then 10 g of organoclay, C25A, was added together and refluxed at 70 ° C for 12 hours. The product was diluted with 5-fold n-propanol (1 L) to remove residues, filtered, and washed several times with ethanol at room temperature. Then, it was dried in a vacuum oven at 40 DEG C for about 48 hours to prepare Epoxy-Clay (EC) as a layered clay compound modified with a silane compound.

Manufacturing example  3. Silane system  As the compound Reformed  Manufacture of Sulfide-Clay

As the layered clay compound, Cloisite (R) 25A (C25A) of Southern Clay Product, USA was used in the same manner as in Preparation Example 2.

HCl was added to the mixed solution (400 g) of ethanol (90 wt%) / distilled water (10 wt%) so that the pH was 3 to 4 and the mixture was stirred for 1 hour. Then, 4 g of bis [(3-triethoxysilylpropyl) tetrasulfide] (TSS) (Shin-Etsu Chemical Co.) was added and the mixture was hydrolyzed by stirring for 2 hours. Then 20 g of C25A as an organoclay was added, and the mixture was stirred at 70 DEG C for 14 hours or longer. The product was filtered, washed several times with ethanol, and then completely dried in a vacuum oven for more than 48 hours to prepare Sulfide-Clay (SC) as a layered clay compound modified with a silane compound.

< Example  And Comparative Example >

Example  1 to 6 and Comparative Example  1-2.

The compositions and contents shown in Table 1 below were combined to prepare colored photosensitive resin compositions.

(Parts by weight) Comparative Example 1 Comparative Example 2 Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Mill base 33 33 33 33 33 33 33 33 Binder resin 8.2 8.2 8.2 8.2 8.2 8.2 8.2 8.2 Photopolymerizable compound 9.2 9.2 9.2 9.2 9.2 9.2 9.2 9.2 Photopolymerization initiator 3 3 3 3 3 3 3 3 The layered clay compound (E-1) - One - - - - - One The layered clay compound (E-2) - - One 2.5 5.5 - - - The layered clay compound (E-3) - - - - - 1.5 2.5 5 additive 0.6 0.6 0.6 0.6 0.6 0.6 0.6 0.6 solvent 40.5 40.5 40.5 39 36 40 39 36.5

Note) In Table 1,

Mill base: The pigment dispersion composition M1 prepared in Preparation Example 1

Binder resin: copolymer of methacrylic acid and benzyl methacrylate (the molar ratio of methacrylic acid unit to benzyl methacrylate unit is 31:69, acid value is 100 mgKOH / g, polystyrene reduced weight average molecular weight is 20,000)

Photopolymerizable compound: KAYARAD DPHA (Nippon Kayaku Co., Ltd.)

Photopolymerization initiator: Irgacure OXE-02 (BASF)

Layered Clay Compound (E-1): Cloisite (R) 25A (C25A) from Southern Clay Product,

Layered clay compound (E-2): Epoxy-Clay

Layered clay compound (E-3): Sulfide-Clay

Solvent: Propylene glycol monomethyl ether acetate

Additives: SH-8400 (Dow Corning)

< Experimental Example >

Experimental Example  1. Measurement and evaluation of moisture content of colored photosensitive resin composition

Each of the colored photosensitive resin compositions prepared in Examples 1 to 6 and Comparative Examples 1 and 2 was applied to a glass of 5 * 5 cm, dried, and then coated to a thickness of 2.5 m. Thereafter, the solvent was removed by drying in a 100 ° C oven for 3 minutes, and the color filter was prepared by exposing the solvent to 300 m in terms of the distance from the photomask to 40 mJ of the 313 nm wavelength of the fusion lamp. The color filter was immersed in a KOH aqueous solution of pH 14 for 3 minutes and then taken out. The color filter was then immersed in distilled water for 1 minute and then taken out. The color filter was cured in an oven at 230 DEG C for 20 minutes and then developed at 150 DEG C for 30 minutes using TDS1200 (ESCO) The amount of water was measured. The results are shown in Table 2. The lower the value, the lower the moisture content.

Experimental Example  2. Preparation of colored photosensitive resin composition Water stain  Measurement evaluation

Each of the colored photosensitive resin compositions prepared in Examples 1 to 6 and Comparative Examples 1 and 2 was applied to a glass of 5 * 5 cm, dried, and then coated to a thickness of 2.5 탆. Thereafter, the solvent was removed by drying in an oven at 100 ° C for 3 minutes, and then the color filter was prepared by exposing the solvent to 300 m in terms of the distance from the photomask to 40 mJ of the 313 nm wavelength of the fusion lamp. The color filter was allowed to stand in distilled water for 10 minutes as shown in Fig. 1, and then blown with nitrogen gas to dry. Then, a stain between the portion not contained in the distilled water and the portion not observed was observed with a surface inspection lamp (FY-100R). The results according to the following evaluation criteria are shown in Table 2 below.

<Evaluation Criteria>

○: Dirt was observed (water stain occurred)

X: No staining observed (no water stains)

Experimental Example  3. Preparation of colored photosensitive resin composition Solvent resistance  evaluation

Each of the colored photosensitive resin compositions prepared in Examples 1 to 6 and Comparative Examples 1 and 2 was applied on a glass substrate of 50 mm x 50 mm using a spin coater by adjusting the number of revolutions so that the film thickness after drying was 2.5 [ And then dried in an oven at 100 ° C for 3 minutes. A color filter was prepared by exposing the dried substrate such that the interval between the substrate and the photomask was 300 mu m so that the accumulated light quantity at a wavelength of 313 nm of the fusion lamp was 40 mJ. Thereafter, it was developed with a spray developing apparatus using a KOH aqueous solution having a pH of 10.5 for 1 minute, washed with water, and then air-dried.

It was then cured in a 230 ° C oven for 20 minutes. This substrate was immersed in a NMP solution at room temperature for 30 minutes, washed with ultrapure water and dried on a hot plate heated to 120 DEG C for 2 minutes, and the chromaticity before and after immersion was measured. The formula used here is calculated by the following equation (1) representing the color change in the three-dimensional colorimetry defined by L *, a *, b *, and a color filter with high reliability can be manufactured as the color change value becomes smaller. The results of the above experimental examples are shown in Table 2 below.

&Quot; (1) &quot;

? Eab * = [(? L *) 2+ (? A *) 2+ (? B *) 2]

Experimental Example  4. Evaluation of the luminance (Y) of the colored photosensitive resin composition

The chromaticity was measured using a colorimeter (OSP-SP2000, Olympus). At this time, the luminance was evaluated as a Y value in the color coordinate of the XYZ color system, and the evaluation criteria of the luminance were as follows, and the results are shown in Table 2 below.

<Evaluation Criteria>

O: Y > 13.0

?: 12.0 < Y? 13.0

X: Y? 12.0

Moisture content Water stain Solvent resistance Luminance Comparative Example 1 9.1 X 6.2 ○ Comparative Example 2 6.5 X 4.5 △ Example 1 5.8 △ 3.6 ○ Example 2 3.5 ○ 2.0 ○ Example 3 2.2 ○ 2.2 △ Example 4 3.2 ○ 3.0 ○ Example 5 3.0 ○ 1.7 ○ Example 6 2.5 ○ 2.0 △

As can be seen from the results of Table 2, in the case of the compositions of the present invention including the layered clay compound modified with the silane compound, in Examples 1 to 6, the water content which can confirm water and moisture barrier properties was low, The solvent resistance was excellent, and the luminance was also suitable for commercialization. Furthermore, it was confirmed that the layered clay compound modified with the silane-based compound plays a role in improving the degree of curing, whereby the water stain evaluation result is also excellent.

It can be confirmed that this is a remarkably superior level to the water content, water stain, solvent resistance and luminance evaluation results of Comparative Examples 1 and 2 which do not include the layered clay compound modified with the silane compound.

Claims (12)

A colorant, a binder resin, a photopolymerizable compound, a photopolymerization initiator, a layered clay compound modified with a silane compound, and a solvent. The method according to claim 1,
About the total weight of solids in the composition
3 to 60% by weight of a colorant,
5 to 85% by weight binder resin,
5 to 50% by weight of a photopolymerizable compound,
1 to 20% by weight of a photopolymerization initiator and
0.1 to 10% by weight of a layered clay compound modified with a silane-based compound,
About the total weight of the composition
And 60 to 90% by weight of a solvent. The composition according to claim 2, wherein, based on the total weight of solids in the composition,
And the layered clay compound modified with the silane compound is contained in an amount of 2 wt% to less than 5 wt%. The method according to claim 1,
And at least one additive selected from fillers, other polymer compounds, pigment dispersants, curing agents, adhesion promoters, antioxidants, ultraviolet absorbers and antiflocculating agents. The method of claim 4,
Wherein the additive is contained in an amount of 0.01 to 10% by weight based on the total weight of the solid content in the colored photosensitive resin composition. The method according to claim 1,
The layered clay compound may be selected from the group consisting of montmorillonite, bentonite, kaolinite, mica, hectorite, fluorohectorite, saponite, beidalite, nontronite, stevensite, vermiculite, hallosite, volkonskoite, suconite, magadite, and kenya Wherein the coloring photosensitive resin composition is at least one selected from the group consisting of styrene, acrylonitrile, and styrene. The method according to claim 1,
Wherein the layered clay compound is an organically modified layered clay compound in which an organic substance is interposed between the layered clay compound layers. The method of claim 7,
The organic material may be selected from the group consisting of quaternary ammonium, phosphonium, maleate, succinate, acrylate, benzylic hydrogen, and oxazoline. Wherein the organic photosensitive material is an organic material containing at least one functional group selected from the group consisting of a halogen atom and a halogen atom. The method according to claim 1,
The silane compound is at least one compound selected from glycidoxypropyltrimethoxy silane and bis [(3-triethoxysilylpropyl) tetrasulfide]) By weight based on the total weight of the colored photosensitive resin composition. The method according to claim 1,
Wherein the colored photosensitive resin composition is used for producing a color filter for an organic light emitting diode. A color filter produced by using the colored photosensitive resin composition of claim 1. An organic light emitting diode comprising the color filter of claim 11.

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