KR20140087983A - Colored photosensitive resin composition and color filter using the same - Google Patents

Abstract

The present invention relates to a colored photosensitive-resin composition which particularly is used for manufacturing a color filter used for a color liquid crystal display device and so on. The present invention aims to provide the colored photosensitive-resin composition from which the color filter having an excellent permeability can be obtained. The colored photosensitive-resin composition includes (A) a coloring agent, (B) an alkali-soluble resin, (C) a photopolymerizable compound, (D) a photopolymerization initiator, (E) solvent, and (F) a thermosetting compound. The (A) coloring agent includes one or more pigments and one or more dyes. The (F) thermosetting compound includes one or more structures of chemical formula 1, chemical formula 2, and chemical formula 1-1.

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, and more particularly, to a colored photosensitive resin composition for a color filter used in manufacturing a color filter used in a color liquid crystal display device or the like.

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

 As the coloring agent in the colored photosensitive resin composition, a pigment dispersion system is generally used. For this purpose, a pigment dispersion method is used. As the pigment dispersion method, there is a method of producing a color filter by photolithography using a coloring and radiation-sensitive composition in which pigments are dispersed in various photosensitive compositions. Since this method uses pigments, sufficient reliability against light and heat can be ensured and it has been widely used as a preferable method for producing a color filter for a large-screen and high-resolution color display (Korean Patent Laid-Open No. 10-2008-0061191) .

However, the conventional color filters also have a low transmittance and a low solvent resistance, heat resistance and hardness of the colored photosensitive resin composition, which is a reality that needs to be improved.

Korean Patent Publication No. 10-2008-0061191

It is an object of the present invention to provide a colored photosensitive resin composition for a color filter which is capable of obtaining a color filter excellent in transmittance. It is another object of the present invention to provide a colored photosensitive resin composition for a color filter excellent in solvent resistance, heat resistance and hardness.

According to an aspect of the present invention,

(A) a colorant, (B) an alkali-soluble resin, (C) a photopolymerizable compound, (D) a photopolymerization initiator, (E) a solvent, and (F) a thermosetting compound,

(A) the colorant comprises at least one kind of pigment and at least one kind of dye, and (F) the thermosetting compound includes at least one of the following chemical formula 1, chemical formula 2 and chemical formula 1-1 By weight based on the total weight of the composition.

[Chemical Formula 1]

(Wherein R 1 to R 5 are each independently a hydroxyl group, -R 6 -R 7 or -R 7, R 6 is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, and R 7 is a hydroxyl group, Alkoxy having 1 to 6 carbon atoms, and all of R1 to R7 can not be hydroxyl groups.

(2)

(Wherein R8 to R11 each independently represent a hydroxyl group, -R12-R13 or -R13, R12 represents an alkyl group having 1 to 6 carbon atoms which is unsubstituted or substituted with a hydroxyl group or an alkoxy group having 1 to 6 carbon atoms, R13 represents a hydroxyl group, Or an alkoxy group having 1 to 6 carbon atoms substituted with an epoxy group, and all of R8 to R13 can not be hydroxyl groups.

[Formula 1-1]

(Wherein R14 to R19 each independently represent a hydroxyl group, -R20-R21 or -R21, wherein R20 is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms which is unsubstituted or substituted with a hydroxyl group, An alkoxy group having 1 to 6 carbon atoms substituted with an epoxy group or an epoxy group, and all of R14 to R21 can not be hydroxyl groups, and the number of n of the polymer is 1 to 1,200.

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

The colored photosensitive resin composition according to the present invention can provide a colored photosensitive resin composition for a color filter excellent in solvent resistance, heat resistance and hardness, and has an advantage that a color filter excellent in transmittance can be obtained.

Hereinafter, the present invention will be described in detail.

The photosensitive resin composition according to the present invention comprises a colorant, (B) an alkali-soluble resin, (C) a photopolymerizable compound, (D) a photopolymerization initiator, (E) a solvent, and (F) a thermosetting compound,

Wherein the colorant (A) comprises at least one pigment and at least one dye, and the thermosetting compound (F) comprises at least one of the following structures (1), (2) Sensitive resin composition.

[Chemical Formula 1]

(Wherein R 1 to R 5 are each independently a hydroxyl group, -R 6 -R 7 or -R 7, R 6 is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, and R 7 is a hydroxyl group, Alkoxy having 1 to 6 carbon atoms, and all of R1 to R7 can not be hydroxyl groups.

(2)

(Wherein R8 to R11 each independently represent a hydroxyl group, -R12-R13 or -R13, R12 represents an alkyl group having 1 to 6 carbon atoms which is unsubstituted or substituted with a hydroxyl group or an alkoxy group having 1 to 6 carbon atoms, R13 represents a hydroxyl group, Or an alkoxy group having 1 to 6 carbon atoms substituted with an epoxy group, and all of R8 to R13 can not be hydroxyl groups.

[Formula 1-1]

(Wherein R14 to R19 each independently represent a hydroxyl group, -R20-R21 or -R21, wherein R20 is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms which is unsubstituted or substituted with a hydroxyl group, An alkoxy group having 1 to 6 carbon atoms substituted with an epoxy group or an epoxy group, and all of R14 to R21 can not be hydroxyl groups, and the number of n of the polymer is 1 to 1,200.

The colorant (A)

The colorant (A) contains at least one pigment (a1) and at least one dye (a2) as essential components.

The pigment (a1) may be an organic pigment or an inorganic pigment generally used in the art. Examples of the organic pigment include 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, Anthanthrone pigments, indanthrone pigments, pravanthrone pigments, anthraquinone pigments, anthraquinone pigments, anthanthrone pigments, anthanthrone pigments, indanthrone pigments, indanthrone pigments, Pyranthrone pigments, diketopyrrolopyrrole pigments, and the like. Examples of the inorganic pigments include metallic compounds such as metal oxides and metal complex salts. Specific examples of the inorganic pigments include metals such as iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony and carbon black Oxides or composite metal oxides. Particularly, the organic pigments and inorganic pigments may be specifically classified into pigments in the Society of Dyers and Colourists, and more specifically, those having a color index (CI) number Pigments, but are not limited thereto.

CI 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

CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, and 71

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

CI Pigment Violet 14, 19, 23, 29, 32, 33, 36, 37 and 38

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

CI Pigment Green 7, 10, 15, 25, 36, 47 and 58

CI Pigment Brown 28

CI Pigment Black 1 and 7 Light

The above-mentioned pigments (a1) may be used alone or in combination of two or more.

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

It is preferable to use a pigment dispersion in which the particle diameter of the pigment (a1) is uniformly dispersed. An example of a method for uniformly dispersing the particle diameter of the pigment includes a method of dispersing the pigment dispersion (a3) by containing the pigment dispersant (a3). According to this method, a pigment dispersion in which the pigment is uniformly dispersed in a solution can be obtained have.

Specific examples of the pigment dispersant (a3) 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 alone or in combination of two or more. Can be used.

The content of the pigment (a1) is in the range of 10 to 50% by weight, preferably 15 to 45% by weight with respect to the total solid content in the pigment dispersion composition. When the content of the pigment is in the range of 15 to 40% by weight, the viscosity is low, the storage stability is excellent, and the dispersion efficiency is high, which is effective for increasing the contrast ratio.

The pigment dispersant (a3) is added for maintenance of deagglomeration and stability of the pigment, and any of those generally used in the art can be used without limitation. (Hereinafter referred to as an acrylic dispersant) containing BMA (butyl methacrylate) or DMAEMA (N, N-dimethylaminoethyl methacrylate). At this time, it is preferable to apply the acrylic dispersant prepared by a living control method as disclosed in Korean Patent Laid-Open Publication No. 2004-0014311. DISCLOSURE OF INVENTION It is an object of the present invention to provide an acrylic dispersant, 2000, DISPER BYK-2001, DISPER BYK-2070, and DISPER BYK-2150.

The acrylic dispersants exemplified above may be used alone or in combination of two or more.

As the pigment dispersant (a3), other resin type pigment dispersants other than the acrylic 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, DISPER BYK-160, BYK (trade name) 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 acrylic dispersant, other resin type pigment dispersants may be used alone or in combination of two or more, or may be used in combination with acrylic dispersion.

The amount of the dispersant (a3) to be used is in the range of 5 to 60 parts by mass, more preferably 15 to 50 parts by mass with respect to 100 parts by mass of the solid content of the pigment (a1). If the content of the pigment dispersant (a3) exceeds 60 parts by mass, the viscosity may be increased. If the content of the pigment dispersant is less than 5 parts by mass, it may be difficult to atomize the pigment or cause gelation after dispersion.

The dye (a2) may be used without limitation as long as it has solubility in an organic solvent. It is preferable to use a dye which has solubility in an organic solvent and can ensure 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 a sulfonic acid and a carboxylic acid, salts of an acidic dye and a nitrogen-containing compound, sulfonamides of an acidic dye and derivatives thereof, and azo, xanthate, phthalocyanine 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 dyes include, as CI solvent dyes,

C.I. Yellow dyes such as Solvent Yellow 4, 14, 15, 16, 21, 23, 24, 38, 56, 62, 63, 68, 79, 82, 93, 94, 98, 99, 151, 162, 163;

C.I. Red dyes such as Solvent Red 8, 45, 49, 89, 111, 122, 125, 130, 132, 146, 179;

C.I. Orange dyes such as solvent orange 2, 7, 11, 15, 26, 41, 45, 56, 62;

C.I. Blue dyes such as Solvent Blue 5, 35, 36, 37, 44, 59, 67 and 70;

C.I. Violet dyes such as solvent violet 8, 9, 13, 14, 36, 37, 47, 49;

Green dyes such as CI solvent green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35 and the like.

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

Also, C.I. As an acid dye

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 Yellow dyes such as 1,1,1,2,2,2,2,2,2,23,28, 240,242, 243,251 and the like, such as, for example, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, ;

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 Red dyes such as 382, 383, 394, 401, 412, 417, 418, 422, 426;

Orange dyes such as C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 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, 340 and the like;

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

Green dyes such as CI Acid Green 1, 3, 5, 9, 16, 25, 27, 50, 58, 63, 65, 80, 104, 105, 106,

CI Acid Yellow 42, which is excellent in solubility in organic solvents in acid dyes; CI Acid Red 92; CI Acid Blue 80, 90; CI Acid Violet 66; CI Acid Green 27 is preferred.

As a C.I. direct dye,

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 , Yellow dyes such as 136, 138, and 141;

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, 250;

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

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

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

Also, C.I. As a modantoic dye

Yellow dyes such as C.I. Modatto Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 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, Red dyes such as 41, 43, 45, 46, 48, 53, 56, 63, 71, 74, 85, 86, 88, 90, 94, 95;

CI Modanato Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, dyes;

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;

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

Green dyes such as CI Modatto Green 1, 3, 4, 5, 10, 15, 19, 26, 29, 33, 34, 35, 41, 43,

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

The content of the dye in the colorant (A) is preferably 0.5 to 80% by weight, more preferably 0.5 to 60% by weight, and particularly preferably 1 to 50% by weight, based on the solid content in the colorant (A) Do. When the content of the dye in the colorant (A) is in the above range, it is possible to prevent the problem of lowering the reliability of elution of the dye by the organic solvent after formation of the pattern.

The content of the colorant (A) is preferably 5 to 60% by weight, and more preferably 10 to 45% by weight based on the solid content in the colored photosensitive resin composition. When the colorant (A) is contained in an amount of 5 to 60% by weight based on the above standard, the color density of the pixel is sufficient even when a thin film is formed, and the residue of the non- Do.

In the present invention, 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.

(B) an alkali-soluble resin

The alkali-soluble resin (B) is prepared by copolymerizing an ethylenically unsaturated monomer (b1) having a carboxyl group as an essential component in order to have solubility in an alkali developing solution used in a developing process for forming a pattern. In order to ensure compatibility with the dye (a2) and storage stability of the colored photosensitive resin composition, the acid value of the alkali-soluble resin (B) is preferably 30 to 150 mgKOH / g. When the acid value of the alkali-soluble resin (B) is less than 30 mgKOH / g, it is difficult to ensure a sufficient developing rate of the colored photosensitive resin composition. When the acid value exceeds 150 mgKOH / g, the adhesion with the substrate is decreased, , The dye in the colored photosensitive resin composition is precipitated or the storage stability of the colored photosensitive resin composition is lowered, and the viscosity tends to rise.

A hydroxyl group may be added to secure further developability of the alkali-soluble resin (B). (B) and the hydroxyl group value of (C) of the photopolymerizable compound is limited to 50 mgKOH / g or more and 250 mgKOH / g or less. When the sum of the hydroxyl groups is less than 50 mgKOH / g, a sufficient developing rate can not be secured. When it exceeds 250 mgKOH / g, the dimensional stability of the formed pattern is lowered and the linearity of the pattern becomes poor and the compatibility with the dye is deteriorated A problem of storage stability tends to occur.

Specific examples of the ethylenically unsaturated monomer (b1) having a carboxyl group include monocarboxylic acids such as acrylic acid, methacrylic acid and crotonic acid; Dicarboxylic acids such as fumaric acid, mesaconic acid and itaconic acid; And anhydrides of these dicarboxylic acids; (meth) acrylates of a polymer having a carboxyl group and a hydroxyl group at both terminals such as? -carboxypolycaprolactone mono (meth) acrylate, and acrylic acid and methacrylic acid are preferable.

(B1) having a carboxyl group and an ethylenically unsaturated monomer (b2) having a hydroxyl group in order to impart a hydroxyl group to the alkali-soluble resin (B). The ethylenically unsaturated monomer having a carboxyl group (b1 ) With a glycidyl group-containing compound (b3). (B3) having a glycidyl group in addition to a copolymer of an ethylenically unsaturated monomer (b1) having a carboxyl group and an ethylenically unsaturated monomer (b2) having a hydroxyl group.

Specific examples of the butylenically unsaturated monomer (b2) having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 4-hydroxybutyl Hydroxy-3-phenoxypropyl (meth) acrylate, N-hydroxyethylacrylamide and the like, and 2-hydroxyethyl (meth) acrylate is preferable, and two or more kinds thereof can be used in combination.

Specific examples of the glycidyl group-containing compound (b3) include butyl glycidyl ether, glycidyl propyl ether, glycidyl phenyl ether, 2-ethylhexyl glycidyl ether, glycidyl butyrate, glycidyl methyl ether, Ethyl glycidyl ether, glycidyl isopropyl ether, t-butyl glycidyl ether, benzyl glycidyl ether, glycidyl 4-t-butyl benzoate, glycidyl stearate, aryl glycidyl ether, Methacrylic acid glycidyl ester, etc., and butyl glycidyl ether, aryl glycidyl ether, and methacrylic acid glycidyl ester are preferable, and two or more kinds may be used in combination.

The unsaturated monomers (b4) copolymerizable in the preparation of the alkali-soluble resin (B) are exemplified below, but are not limited thereto.

Specific examples of the polymerizable monomer (b4) having an unsaturated bond capable of copolymerization include styrene, vinyltoluene,? -Methylstyrene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p- Aromatic vinyls such as vinylbenzyl methyl ether, m-vinylbenzyl methyl ether, p-vinyl benzyl methyl ether, o-vinyl benzyl glycidyl ether, m- vinyl benzyl glycidyl ether and p- compound;

N-cyclohexylmaleimide, N-benzylmaleimide, N-phenylmaleimide, No-hydroxyphenylmaleimide, Nm-hydroxyphenylmaleimide, Np-hydroxyphenylmaleimide, No-methylphenylmaleimide, Nm N-substituted maleimide-based compounds such as methylphenyl maleimide, Np-methylphenyl maleimide, No-methoxyphenyl maleimide, Nm-methoxyphenyl maleimide and Np-methoxyphenyl maleimide;

Propyl (meth) acrylate, n-butyl (meth) acrylate, i-butyl (meth) acrylate, alkyl (meth) acrylates such as sec-butyl (meth) acrylate and t-butyl (meth) acrylate; (Meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, tricyclo [5.2.1.0 2,6] decan- Alicyclic (meth) acrylates such as dicyclopentanyloxyethyl (meth) acrylate and isobornyl (meth) acrylate;

Aryl (meth) acrylates such as phenyl (meth) acrylate and benzyl (meth) acrylate;

3- (methacryloyloxymethyl) -2-trifluoromethyl oxetane, 3- (methacryloyloxymethyl) oxetane, 3- (methacryloyloxymethyl) 2- (methacryloyloxymethyl) oxetane, 2- (methacryloyloxymethyl) -4-trifluoromethyloxetane, and the like Unsaturated oxetane compounds.

The monomers exemplified in the above (b4) may be used alone or in combination of two or more.

The content of the alkali-soluble resin (B) should satisfy the condition that the sum of the hydroxyl value of the alkali-soluble resin (B) and the hydroxyl group value of the photopolymerizable compound (C) is from 50 mgKOH / g to 250 mgKOH / g, By weight, preferably 10 to 70% by weight. When the content of the alkali-soluble resin (B) is 10 to 80% by weight based on the above-mentioned criteria, the solubility in a developing solution is sufficient and pattern formation is easy. In the development, film reduction of the pixel portion of the exposed portion is prevented, It is preferable that the dropout property is improved.

(C) Photopolymerization  compound

The photopolymerizable compound (C) is a compound capable of polymerizing under the action of the photopolymerization initiator (D) described below, and a monofunctional monomer, a bifunctional monomer or a polyfunctional monomer can be used, and preferably a bifunctional or more polyfunctional monomer Can be used.

Specific examples of the monofunctional monomer include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate or N- But are not limited thereto.

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

Specific examples of the polyfunctional monomer include trimethylolpropane tri (meth) acrylate, ethoxylated trimethylolpropane tri (meth) acrylate, propoxylated trimethylolpropane tri (meth) acrylate, pentaerythritol tri (Meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, ethoxylated dipentaerythritol hexa (meth) acrylate, propoxylated dipentaerythritol hexa ) Acrylate or dipentaerythritol hexa (meth) acrylate, but are not limited thereto.

The photopolymerizable compound (C) is preferably contained in an amount of 5 to 45% by weight, more preferably 7 to 45% by weight based on the solid content in the colored photosensitive resin composition. When the photopolymerizable compound (C) is contained in an amount of 5 to 45% by weight based on the above-mentioned criteria, the strength and smoothness of the pixel portion are preferably improved.

(D) Light curing Initiator

The photopolymerization initiator (D) comprises a photopolymerization initiator (d1) having a structure represented by the following general formula (13).

[Chemical Formula 13]

[Chemical Formula 14]

In the formula (13), R 1 is represented by the following formula (14), R 4 in the formula (14) is a C 1 -C 4 alkyl, R 5 is a C 3 -C 8 ring structure, and the formula R 2 is a C 1 -C 8 alkyl, phenyl, , A substituted or unsubstituted benzyl group, and R 3 is a substituted or unsubstituted diphenylsulfide group.

The photopolymerization initiator (d1), which is a structure of the above formula (13), exhibits effective photopolymerization properties in a colored photosensitive resin composition containing a dye as a colorant by preventing a decrease in sensitivity due to a dye.

In addition, the photopolymerization initiator (d2) other than those described above may be further used in combination within the range not impairing the effects of the present invention. Typically, it is preferable to use at least one compound selected from the group consisting of an acetophenone-based compound, a benzophenone-based compound, a triazine-based compound, a nonimidazole-based compound, and a thioxanthone-based compound.

Specific examples of the acetophenone-based compound include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethylketal, 2-hydroxy- 1- [4- 2-methyl-1- (4-methylthiophenyl) -2-morpholinopropane-1-one, 2-methylcyclohexyl phenyl ketone, 2-methyl-1- [4- (1-methylvinyl) phenyl] propane-1-one 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinophenyl) butan-1-one.

Examples of the benzophenone compound include benzophenone, methyl 0-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3 ', 4,4'-tetra tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone, 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-methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, (Trichloromethyl) -6- [2- (5-methylfuran-2- (4-methoxystyryl) -1,3,5-triazine, Yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (furan- , 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2-methylphenyl) ethenyl] -1,3,5-triazine, 2,4- ) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine.

Specific examples of the imidazole compound include 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbimidazole, 2,2'-bis (2,3- Phenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (alkoxyphenyl) , 2,2'-bis (2,6-dichlorophenyl) -4,4 ', 5,5'-tetra (trialkoxyphenyl) Imidazole compounds in which 4'5,5'-tetraphenyl-1,2'-biimidazole or phenyl groups at 4,4 ', 5,5' positions are substituted by carboalkoxy groups. Among them, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,3- , 2,2-bis (2,6-dichlorophenyl) -4,4'5,5'-tetraphenyl-1,2'-biimidazole is preferably used do.

Examples of the thioxanthone compound include 2-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4- .

The photopolymerization initiator (D) may further include a photopolymerization initiator (d3) to improve the sensitivity of the colored photosensitive resin composition of the present invention. The colored photosensitive resin composition according to the present invention contains a photopolymerization initiation auxiliary (d3), whereby the sensitivity is further increased and the productivity can be improved.

As the above-mentioned (d3), for example, at least one compound selected from the group consisting of an amine compound, a carboxylic acid compound and an organic sulfur compound having a thiol group can be preferably used.

As the amine compound, an aromatic amine compound is preferably used. Specific examples of the amine compound include aliphatic amine compounds such as triethanolamine, methyldiethanolamine and triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, 4- Dimethylaminobenzoic acid, 2-ethylhexyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, N, N-dimethylparatoluidine, 4,4'-bis (dimethylamino) benzophenone ), 4,4'-bis (diethylamino) benzophenone, and the like.

The carboxylic acid compound is preferably an aromatic heteroacetic acid, and more specifically, it is preferably an aromatic heteroaromatic acid such as phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthio Acetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid and the like.

Specific examples of the organic sulfur compound having a thiol group include 2-mercaptobenzothiazole, 1,4-bis (3-mercaptobutyryloxy) butane, 1,3,5-tris (3-mercaptobutyloxyethyl) 1,3,5-triazine-2,4,6 (1H, 3H, 5H) -thione, trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis (3-mercaptopropionate), dipentaerythritol hexacis (3-mercaptopropionate), and tetraethylene glycol bis (3-mercaptopropionate) .

The photopolymerization initiator (D) is contained in an amount of 0.1 to 40 parts by weight, preferably 1 to 30 parts by weight, based on 100 parts by weight of the alkali-soluble resin (B) and the photopolymerizable compound (C) contained in the colored photosensitive resin composition of the present invention . When the photopolymerization initiator (D) is in the range of 0.1 to 40 parts by weight based on the above-mentioned criteria, the colored photosensitive resin composition is highly sensitized and the exposure time is shortened, so that productivity is improved and high resolution can be maintained. It is preferable that the strength of the formed pixel portion and the smoothness on the surface of the pixel portion are improved.

In the case of the photopolymerization initiator (d1) having the structure of Formula 1, 10 to 100 parts by weight, preferably 20 to 100 parts by weight, based on 100 parts by weight of the total photopolymerization initiator, should be included. When the proportion of (d1) in the total photopolymerization initiator is less than 10 parts by weight, the sensitivity deterioration due to the dye can not be overcome and the pattern is likely to be short-circuited during the development process.

When the photopolymerization initiation auxiliary (d3) is further used, the photopolymerization initiation auxiliary (d3) is added to 100 parts by weight of the alkali-soluble resin (B) and the photopolymerization compound (C) contained in the colored photosensitive resin composition of the present invention 0.1 to 40 parts by weight, preferably 1 to 30 parts by weight. When the amount of the photopolymerization initiator (d3) used is within the range of 0.1 to 40 parts by weight, the sensitivity of the colored photosensitive resin composition becomes higher and the productivity of the color filter formed using the composition is improved.

Solvent (E)

The solvent used in the conventional colored photosensitive resin composition may be used without particular limitation as long as it is effective in dissolving the other components contained in the colored photosensitive resin composition. The solvent (E) may be selected from ethers, aromatic hydrocarbons, ketones, Alcohols, esters, amides and the like are preferable.

Examples of the solvent (E) 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,

Ethylene glycol alkyl ether acetates such as methyl cellosolve acetate and ethyl cellosolve acetate,

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,

Aromatic hydrocarbons such as benzene, toluene, xylene, and mesitylene,

Ketones such as methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone and cyclohexanone,

Alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol and glycerin,

Esters such as ethyl 3-ethoxypropionate and methyl 3-methoxypropionate, and cyclic esters such as? -Butyrolactone.

The solvent (E) is preferably an organic solvent having a boiling point of 100 ° C to 200 ° C on the application and drying surface, more preferably propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, ethyl lactate , Butalactate, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, and the like.

The above-mentioned (E) solvents may be used alone or in admixture of two or more, and may be contained in an amount of 60 to 90% by weight, preferably 70 to 85% by weight, based on the total weight of the colored photosensitive resin composition of the present invention have. When the solvent (E) is in the range of 60 to 90% by weight as described above, when it is coated with a coating apparatus such as a roll coater, a spin coater, a slit and spin coater, a slit coater Thereby providing an effect of improving the property.

(F) Thermosetting compound

The thermosetting compound (F) includes at least one of the following structures (1), (2) and (1-1).

[Chemical Formula 1]

(Wherein R 1 to R 5 are each independently a hydroxyl group, -R 6 -R 7 or -R 7, R 6 is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, and R 7 is a hydroxyl group, Alkoxy having 1 to 6 carbon atoms, and all of R1 to R7 can not be hydroxyl groups.

(2)

(Wherein R8 to R11 each independently represent a hydroxyl group, -R12-R13 or -R13, R12 represents an alkyl group having 1 to 6 carbon atoms which is unsubstituted or substituted with a hydroxyl group or an alkoxy group having 1 to 6 carbon atoms, R13 represents a hydroxyl group, Or an alkoxy group having 1 to 6 carbon atoms substituted with an epoxy group, and all of R8 to R13 can not be hydroxyl groups.

[Formula 1-1]

(Wherein R14 to R19 each independently represent a hydroxyl group, -R20-R21 or -R21, wherein R20 is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms which is unsubstituted or substituted with a hydroxyl group, An alkoxy group having 1 to 6 carbon atoms substituted with an epoxy group or an epoxy group, and all of R14 to R21 can not be hydroxyl groups, and the number of n of the polymer is 1 to 1,200.

Specifically, the formula (1) may be any one of the following formulas (3) to (7).

(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

Specifically, the formula (2) may be any one of the following formulas (8) to (12).

[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

The content of the thermosetting compound (F) is preferably 5 to 45% by weight, more preferably 7 to 45% by weight, based on the solid content in the photosensitive resin composition. When the thermosetting compound (F) is contained in an amount of 5 to 45% by weight based on the solid content in the photosensitive resin composition, it is preferable that the occurrence of unevenness after development is small and the solvent resistance is good.

The process for producing the colored photosensitive resin composition of the present invention will be described as follows.

First, the pigment (a1) in the colorant (A) is mixed with the solvent (E) and dispersed using a bead mill or the like until the average particle diameter of the pigment becomes about 0.2 μm or less. At this time, if necessary, the pigment dispersant (a3), part or all of the alkali-soluble resin (B), or (a2) the dye may be dissolved or dispersed by mixing with the (E) solvent.

The dye (a2), the remainder of the alkali-soluble resin (B), the photopolymerizable compound (C) and the photopolymerization initiator (D), the thermosetting compound (F) and the solvent (E) Whereby the colored photosensitive resin composition according to the present invention can be produced.

Hereinafter, the present invention will be described in more detail with reference to examples. However, the embodiments of the present invention described below are illustrative only and the scope of the present invention is not limited to these embodiments. The scope of the present invention is indicated in the claims, and moreover, includes all changes within the meaning and range of equivalency of the claims. In the following Examples and Comparative Examples, "%" and "part" representing the content are on a mass basis unless otherwise specified.

Preparation of pigment dispersion composition

<Pigment dispersion composition M1>

4.0 parts by mass of DISPERBYK-2001 (manufactured by BYK) as a pigment dispersant, 44 parts by mass of propylene glycol methyl ether acetate as a solvent and 40 parts by mass of propylene glycol methyl ether as a pigment were mixed with 12.0 parts by mass of CI Pigment Blue 15: 6 And mixed / dispersed for 12 hours to prepare a pigment dispersion M1.

Synthesis of alkali-soluble resin

&Lt; Synthesis Example 1 &

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

Synthesis of thermosetting compounds

&Lt; Synthesis Example 2 &

25 g of alpha -D-glucopyranose is dissolved in 100 mL of 5% sodium hydroxide aqueous solution, and then 50 g of epichlorohydrin and 30 mg of sodium borohydride are added. The mixture is heated to 40 DEG C and stirred for 2 hours. It was extracted with dichloromethane and then evaporated. The resultant was dried in a vacuum oven at 80 DEG C for 48 hours.

&Lt; Synthesis Example 3 &

Dissolve 25 g of alpha -D-glucofuranose in 100 mL of 5% aqueous sodium hydroxide solution, then add 50 g of epichlorohydrin and 30 mg of sodium borohydride. The mixture is heated to 40 DEG C and stirred for 2 hours. It was extracted with dichloromethane and then evaporated. The resultant was dried in a vacuum oven at 80 DEG C for 48 hours.

&Lt; Synthesis Example 4 >

25 g of cellulose is dissolved in 100 mL of 5% sodium hydroxide aqueous solution, and then 50 g of epichlorohydrin and 30 mg of sodium borohydride are added. The mixture is heated to 40 DEG C and stirred for 2 hours. It was extracted with dichloromethane and then evaporated. The resultant was dried in a vacuum oven at 80 DEG C for 48 hours.

Preparation of colored photosensitive resin composition

&Lt; Example 1 >

, 22.5 parts of the pigment dispersion composition M1, 0.3 part of CI Solvent Blue 44 (trade name: VALIFAST BLUE 2620, manufactured by Orient Kagaku Kogyo K.K.), 12.5 parts of the resin of Synthesis Example 1, 12.5 parts of acrylate of dipentaerythritol (KAYARAD DPHA, manufactured by Nippon Kayaku Co., Ltd.), 0.9 part of Irgacure OXE01 (manufactured by BASF), 0.9 part of the thermosetting compound of the structural formula 2, 21.3 parts of propylene glycol monomethyl ether acetate, and 36.5 parts of propylene glycol monomethyl ether Were mixed to prepare a colored photosensitive resin composition.

&Lt; Example 2 >

, 22.5 parts of the pigment dispersion composition M1, 0.3 part of CI Solvent Blue 44 (trade name: VALIFAST BLUE 2620, manufactured by Orient Kagaku Kogyo K.K.), 12.5 parts of the resin of Synthesis Example 1, 12.5 parts of acrylate of dipentaerythritol (KAYARAD DPHA (manufactured by Nippon Kayaku)), 0.9 parts of Irgacure OXE01 (manufactured by BASF), 0.9 parts of the thermosetting compound of the structural formula 3, 21.3 parts of propylene glycol monomethyl ether acetate, and 36.5 parts of propylene glycol monomethyl ether Were mixed to prepare a colored photosensitive resin composition.

&Lt; Example 3 >

, 22.5 parts of the pigment dispersion composition M1, 0.3 part of CI Solvent Blue 44 (trade name: VALIFAST BLUE 2620, manufactured by Orient Kagaku Kogyo K.K.), 12.5 parts of the resin of Synthesis Example 1, 12.5 parts of acrylate of dipentaerythritol (KAYARAD DPHA (manufactured by Nippon Kayaku)), 0.9 parts of Irgacure OXE01 (manufactured by BASF), 0.9 parts of the thermosetting compound of the structural formula 4, 21.3 parts of propylene glycol monomethyl ether acetate, and 36.5 parts of propylene glycol monomethyl ether Were mixed to prepare a colored photosensitive resin composition.

&Lt; Comparative Example 1 &

, 22.5 parts of the pigment dispersion composition M1, 0.3 part of CI Solvent Blue 44 (trade name: VALIFAST BLUE 2620, manufactured by Orient Kagaku Kogyo K.K.), 13.6 parts of the resin of Synthesis Example 1, 13.5 parts of acrylate of dipentaerythritol (KAYARAD DPHA (manufactured by Nippon Kayaku)), 1.0 part of Irgacure OXE01 (BASF), 21.3 parts of propylene glycol monomethyl ether acetate and 35.8 parts of propylene glycol monomethyl ether were mixed to prepare a colored photosensitive resin composition.

&Lt; Comparative Example 2 &

25.0 parts of the pigment dispersion composition M1, 12.4 parts of the resin of Synthesis Example 1, 5.0 parts of acrylate compounds of dipentaerythritol (KAYARAD DPHA (Nippon Kayaku)), 0.9 parts of Irgacure OXE01 (BASF) Synthetic Example 3 A colored photosensitive resin composition was prepared by mixing 0.9 part of the thermosetting compound in the structure, 34.5 parts of propylene glycol monomethyl ether acetate, and 21.3 parts of propylene glycol monomethyl ether.

&Lt; Comparative Example 3 &

, 22.5 parts of the pigment dispersion composition M1, 0.3 part of CI Solvent Blue 44 (trade name: VALIFAST BLUE 2620, manufactured by Orient Kagaku Kogyo K.K.), 12.5 parts of the resin of Synthesis Example 1, 12.5 parts of acrylate of dipentaerythritol , 0.1 part of Irgacure OXE01 (manufactured by BASF), 0.9 part of a thermosetting compound having a structure of cresol novolak (manufactured by Sumitomo Chemical Co., Ltd.), 21.3 parts of propylene glycol monomethyl ether acetate, 0.1 part of propylene glycol mono (manufactured by Nippon Kayaku Co., And 36.5 parts of methyl ether were mixed to prepare a colored photosensitive resin composition.

Experimental Example  1: Measurement of development speed, adhesion and hardness

A color filter was prepared using the colored photosensitive resin compositions prepared in Examples 1 to 3 and Comparative Examples 1 to 3.

Specifically, each of the above colored photosensitive resin compositions was applied on a 2-inch-square glass substrate ("EAGLE XG", manufactured by Corning Inc.) by spin coating, then placed on a heating plate and held at a temperature of 100 ° C. for 3 minutes to form a thin film . Subsequently, a test photomask having a pattern for changing the transmittance in the range of 1 to 100% to a step-like pattern and a line / space pattern of 1 to 50 m was placed on the thin film and the distance between the test photomask and the test photomask was set to 100 m. Respectively. At this time, the ultraviolet light source was irradiated with a high pressure mercury lamp of 1 KW containing g, h and i lines at an illuminance of 100 mJ / cm 2, and no special optical filter was used. The thin film irradiated with ultraviolet rays was immersed in a KOH aqueous solution of pH 10.5 for 2 minutes to develop. The glass plate coated with the thin film was washed with distilled water, and then blown with nitrogen gas, dried, and heated in a heating oven at 200 ° C for 25 minutes to prepare a color filter. The film thickness of the color filter prepared above was 2.3 탆.

&Lt; Development speed >

The time required for completely dissolving the non-exposed part in the developing solution at the time of development was measured and is shown in Table 1 below.

○: ~ 15 seconds

B: 15 to 20 seconds

×: 20 seconds or more

Development speed Example 1 ○ Example 2 ○ Example 3 ○ Comparative Example 1 X Comparative Example 2 △ Comparative Example 3 △

&Lt; Adhesion >

The resultant pattern was evaluated by an optical microscope, and the degree of peeling was evaluated on the following pattern. The results are shown in Table 2 below.

○: No pattern peeling

△: 1 to 3 pattern peeling

X: Pattern peeling 4 or more

Adhesiveness Example 1 ○ Example 2 ○ Example 3 ○ Comparative Example 1 X Comparative Example 2 △ Comparative Example 3 △

<Solvent resistance>

The prepared color filter was immersed in an N-methylpyrrolidone solvent for 30 minutes, and the color change before and after the evaluation was compared and evaluated, as shown in Table 3 below.

The formula to be used at this time is calculated by the following equation (1) representing the color change in the three-dimensional colorimetry defined by L *, a *, b *, and as the color change value is small, a reliable color filter can be manufactured .

When the value of DELTA E * ab is 3.0 or less, a person can not feel color difference.

?: The value of? E * ab is less than 2.0

?: The value of? E * ab is 2.0 to 3.0

X: DELTA E * ab value is 3.0 or more

Equation (1)

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

△ E * ab Example 1 1.10 ○ Example 2 1.13 ○ Example 3 1.23 ○ Comparative Example 1 3.35 X Comparative Example 2 3.14 X Comparative Example 3 1.85 ○

<Hardness Measurement>

The fabricated color filter was measured for Martens Hardness (HM) by a micro-hardness meter and is shown in Table 4 below.

Equipment and conditions were done as follows.

Equipment: Fischerscope H100C

Mode: Load-Unload

Loaing Speed: 0.15mN / sec

Total Loading Time: 8 sec

Loading Creep Time: 15 sec

Unloading Creep Time: 0 sec

Indenter: Vickers Indenter

?: Hardness value of not less than 250.0

?: Hardness value of 240.0 to 250.0

X: Hardness value less than 240.0

Martens Hardness (HM) Example 1 294.4 ○ Example 2 293.9 ○ Example 3 293.1 ○ Comparative Example 1 235.7 X Comparative Example 2 293.5 ○ Comparative Example 3 289.7 ○

Experimental Example  2: Measurement of transmittance and contrast ratio

<Transmittance and Contrast Ratio>

The transmittance and the contrast ratio were measured using a color filter manufactured in the same manner as in Experimental Example 1 except that the test photomask was not used.

In the case of the contrast ratio, the substrate of the color filter was sandwiched between two sheets of polarizing plates, and the maximum and minimum values of the transmitted light intensity were measured by rotating the front side deflector plate while illuminating the fluorescent lamp (wavelength: 380 to 780 nm) -2000 brightness meter (KONICA MINOLTA), and the contrast ratio, which is a value obtained by dividing the maximum value by the minimum value, was calculated. For the transmittance, a colorimeter (OSP-200 manufactured by Olympus Corporation) was used.

The measured transmittance and contrast ratio are shown in Table 5 and Table 6, respectively.

?: Transmittance of 12.20 or more

?: Transmittance was 11.50 to 12.20

X: transmittance not more than 11.50

Transmittance Example 1 12.36 ○ Example 2 12.34 ○ Example 3 12.36 ○ Comparative Example 1 12.32 ○ Comparative Example 2 11.41 X Comparative Example 3 12.19 △

○: Contrast ratio over 17,500

△: Contrast ratio between 16,000 and 17,500

X: Contrast ratio less than 16,000

Contrast ratio Example 1 17,821 ○ Example 2 17,505 ○ Example 3 17,723 ○ Comparative Example 1 17,103 △ Comparative Example 2 15,950 X Comparative Example 3 16,804 △

As described above, the photosensitive resin compositions of Examples 1 to 3 were found to have excellent characteristics in terms of development unevenness, adhesion, solvent resistance, hardness, transmittance and contrast ratio as compared with Comparative Examples 1 to 3.

Therefore, it can be understood that the photosensitive resin composition according to the present invention can provide a colored photosensitive resin composition for a color filter excellent in solvent resistance, heat resistance and hardness, and a color filter excellent in transmittance can be obtained.

Claims (10)

(A) a colorant, (B) an alkali-soluble resin, (C) a photopolymerizable compound, (D) a photopolymerization initiator, (E) a solvent, and (F) a thermosetting compound,
Wherein the colorant (A) comprises at least one pigment and at least one dye, and the thermosetting compound (F) comprises at least one of the following structures (1), (2) Sensitive resin composition.
[Chemical Formula 1]

(Wherein R 1 to R 5 are each independently a hydroxyl group, -R 6 -R 7 or -R 7, R 6 is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, and R 7 is a hydroxyl group, Alkoxy having 1 to 6 carbon atoms, and all of R1 to R7 can not be hydroxyl groups.
(2)

(Wherein R8 to R11 each independently represents a hydroxyl group, -R12-R13 or -R13, R12 represents an alkyl group having 1 to 6 carbon atoms which is unsubstituted or substituted with a hydroxyl group or an alkoxy group having 1 to 6 carbon atoms, R13 represents a hydroxyl group, Or an alkoxy group having 1 to 6 carbon atoms substituted with an epoxy group, and all of R8 to R13 can not be hydroxyl groups.
[Formula 1-1]

(Wherein R14 to R19 each independently represent a hydroxyl group, -R20-R21 or -R21, wherein R20 is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms which is unsubstituted or substituted with a hydroxyl group, An alkoxy group having 1 to 6 carbon atoms substituted with an epoxy group or an epoxy group, and all of R14 to R21 can not be hydroxyl groups, and the number of n of the polymer is 1 to 1,200.
The method according to claim 1,
Wherein the formula (1) is any one of the following formulas (3) to (7).
(3)

[Chemical Formula 4]

[Chemical Formula 5]

[Chemical Formula 6]

(7)

The method according to claim 1,
Wherein the formula (2) is any one of the following formulas (8) to (12).
[Chemical Formula 8]

[Chemical Formula 9]

[Chemical formula 10]

(11)

[Chemical Formula 12]

The method according to claim 1,
The colored photosensitive resin composition contains, based on the total solid weight,
The colorant (A) is contained in an amount of 5 to 60% by weight,
The alkali-soluble resin (B) is contained in an amount of 10 to 80% by weight,
The photopolymerizable compound (C) is contained in an amount of 5 to 45% by weight,
The solvent (E) comprises 60 to 90% by weight,
The thermosetting compound (F) is contained in an amount of 5 to 45% by weight,
Wherein the photopolymerization initiator (D) is contained in an amount of 0.1 to 40% by weight based on the total amount of the alkali-soluble resin (B) and the photopolymerizable compound (C). The method according to claim 1,
Wherein the acid value of the alkali-soluble resin (B) is 30 to 150 mgKOH / g. The method according to claim 1,
Wherein the content of the dye in the colorant (A) is 0.5 to 80% by weight based on the total weight of the solid content of the colorant (A). The method according to claim 1,
The photopolymerization initiator (D) is at least one compound selected from the group consisting of an acetophenone compound, a benzophenone compound, a triazine compound, a nonimidazole compound, an oxime compound and a thioxanthone compound. Colored photosensitive resin composition. The method of claim 7,
Wherein the photopolymerization initiator (D) further comprises at least one photopolymerization initiator (d3) selected from the group consisting of an amine compound, a carboxylic acid compound and an organic sulfur compound having a thiol group. The method of claim 8,
The photopolymerization initiator (d3) is contained in an amount of 0.1 to 40 wt% based on the total amount of the alkali-soluble resin (B) and the photopolymerizable compound (C) based on the total solid weight of the colored photosensitive resin composition. Composition. A color filter made of the colored photosensitive resin composition according to any one of claims 1 to 9.