Colored photosensitive resin composition, color filter, and image display device

Abstract

SOLUTION: To provide a colored photosensitive resin composition which contains a coloring agent, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent, wherein the photopolymerizable compound contains 10-50 wt.% of a tetra- or higher functional (meth)acrylic monomer added with 45 or more ethylene oxides having specific structures with respect to 100 wt.% of the whole photopolymerizable compound, a color filter formed using the same, and an image display device having the color filter.EFFECT: A colored photosensitive resin composition is excellent in adhesion at the time of formation of an ultrahigh resolution pattern, and prevents a residue of a lower substrate and uneven development.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a colored photosensitive resin composition, a color filter, and an image display device, and more particularly to a colored photosensitive resin composition that has excellent adhesion when forming an ultra-high resolution pattern and does not leave residue on a lower substrate or cause uneven development, a color filter formed using the same, and an image display device including the color filter. [Background technology]

[0002] Color filters are widely used in plasma display panels (PDPs), liquid crystal displays (LCDs), field emission displays (FELs), light emitting displays (LEDs), etc., and their range of applications is rapidly expanding. In particular, color filters are recognized as one of the most important components in reproducing the color tones of LCDs.

[0003] Recently, the size of pixels in color filters has been reduced in order to realize ultra-high resolution image quality. Accordingly, there is a demand for colored photosensitive resin compositions that have excellent adhesion even when forming ultra-fine patterns and that do not leave residues on the underlying substrate or cause uneven development.

[0004] In the past, dipentaerythritol hexaacrylate (hereinafter referred to as DPHA) was used as a photopolymerizable compound for forming color filters for liquid crystal displays (LCDs), and a composition containing only DPHA was used. However, when only DPHA was used, there was a problem that the composition that should be removed by an alkaline developer during development when forming ultrafine patterns remained on the substrate as a residue.

[0005] In particular, this problem becomes more serious when developing using a paddle method for saving developer and ensuring large area uniformity.

[0006] Meanwhile, Korean Patent Publication No. 10-2009-0072754 discloses a composition for color filters containing a pigment and a binder resin, but has a problem in that pattern characteristics are deteriorated when a super high resolution pattern is formed. Summary of the Invention [Problem to be solved by the invention]

[0007] An object of the present invention is to provide a colored photosensitive resin composition which has excellent adhesion when forming an ultra-high resolution pattern and does not leave residue on the underlying substrate or cause uneven development.

[0008] Another object of the present invention is to provide a color filter formed using the colored photosensitive resin composition.

[0009] It is still another object of the present invention to provide an image display device equipped with the above color filter. [Means for solving the problem]

[0010] On the other hand, the present invention provides a colored photosensitive resin composition comprising a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent, The photopolymerizable compound provides a colored photosensitive resin composition containing a tetrafunctional or higher (meth)acrylic monomer having ethylene oxide added thereto, represented by the following chemical formula 1, in an amount of 10 to 50% by weight based on 100% by weight of the total photopolymerizable compound.

[0011] [ka]

[0012] In the above formula, X is an aliphatic hydrocarbon group having 1 to 10 carbon atoms which may or may not contain oxygen or a heteroatom, or A; R 1 is an aliphatic hydrocarbon group having 1 to 10 carbon atoms which may or may not contain oxygen or a heteroatom, R2 is an aliphatic hydrocarbon group having 1 to 10 carbon atoms, which may or may not contain a heteroatom; A is,

[0013] [ka]

[0014] and R 3 is hydrogen or a methyl group, EO is an ethylene oxide group; n is an integer from 1 to 4, m is an integer from 45 to 96.

[0015] In one embodiment of the present invention, the photopolymerizable compound may further include a tri- or higher functional (meth)acrylic monomer.

[0016] In one embodiment of the present invention, the tri- or higher functional (meth)acrylic monomer may be included in an amount of 50 to 90% by weight based on 100% by weight of the total photopolymerizable compound.

[0017] In one embodiment of the present invention, the photopolymerizable compound may be included in an amount of 5 to 80% by weight based on 100% by weight of the total solid content in the colored photosensitive resin composition.

[0018] In one embodiment of the present invention, the photopolymerization initiator may include an oxime-based photopolymerization initiator.

[0019] On the other hand, the present invention provides a color filter formed using the colored photosensitive resin composition.

[0020] On the other hand, the present invention provides an image display device comprising the above-mentioned color filter. Effect of the Invention

[0021] The colored photosensitive resin composition according to the present invention contains a tetrafunctional or higher (meth)acrylic monomer having 45 or more ethylene oxide units of a specific structure added thereto as a photopolymerizable compound within a specific content range, and therefore has excellent adhesion, and does not leave residue on the underlying substrate or cause uneven development, and therefore has excellent developability even when subjected to a paddle type development process to form an ultra-high resolution pattern. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0022] The present invention will now be described in more detail. One embodiment of the present invention relates to a colored photosensitive resin composition comprising a colorant (A), an alkali-soluble resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D), and a solvent (E), in which the photopolymerizable compound (C) contains a tetrafunctional or higher (meth)acrylic monomer having 45 or more ethylene oxide units of a specific structure added thereto in an amount of 10 to 50% by weight relative to 100% by weight of the total photopolymerizable compound.

[0023] Colorant (A) In one embodiment of the invention, the colorant (A) comprises a pigment (a1) and / or a dye (a2).

[0024] Pigment (a1) The pigment may be an organic or inorganic pigment commonly used in the art. The organic pigment may be any of various pigments used in printing inks, inkjet inks, and the like. Specific examples of the organic pigment include water-soluble azo pigments, insoluble azo pigments, phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, isoindoline pigments, perylene pigments, perinone pigments, dioxazine pigments, anthraquinone pigments, dianthraquinonyl pigments, anthrapyrimidine pigments, anthanthrone pigments, indanthrone pigments, flavanthrone pigments, pyranthrone pigments, and diketopyrrolopyrrole pigments.

[0025] Examples of the inorganic pigment include metal compounds such as metal oxides and metal complex salts. Specific examples of the inorganic pigment include oxides or composite metal oxides of metals such as iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, and antimony; and carbon black.

[0026] In particular, the organic pigments and inorganic pigments include compounds classified as pigments in the Colour Index (published by The Society of Dyers and Colourists), more specifically, pigments with the following Colour Index (CI) numbers, but are not necessarily limited thereto.

[0027] 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, etc. Among the CI pigment pigments exemplified above, a pigment selected from 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 15:6, CI Pigment Green 7, CI Pigment Green 36, and CI Pigment Green 58 may be suitably used.

[0028] These may be used alone or in combination of two or more.

[0029] It is preferable to use a pigment dispersion in which the pigment is uniformly dispersed. One example of a method for uniformly dispersing the pigment is a method in which a pigment dispersant (a3) ​​is added and a dispersion treatment is performed. This method can obtain a pigment dispersion in which the pigment is uniformly dispersed in the solution.

[0030] Pigment dispersants (a3) The pigment dispersant (a3) ​​is added to deflocculate the pigment and maintain its stability. Specific examples of the pigment dispersant include cationic, anionic, nonionic, amphoteric, polyester, and polyamine surfactants, and these may be used alone or in combination of two or more.

[0031] In addition, it is 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-based dispersants include DISPER BYK-2000, DISPER BYK-2001, DISPER BYK-2070, and DISPER BYK-2150, and the acrylate-based dispersants may be used alone or in combination of two or more.

[0032] The pigment dispersant (a3) ​​may be any other resin-type pigment dispersant in addition to the acrylate-based dispersant. Examples of the other resin-type pigment dispersants include known resin-type pigment dispersants, particularly polyurethanes, polycarboxylates, unsaturated polyamides, polycarboxylic acids, (partial) amine salts of polycarboxylic acids, ammonium salts of polycarboxylic acids, alkylamine salts of polycarboxylic acids, polysiloxanes, long-chain polyaminoamidophosphate salts, esters of hydroxyl-containing polycarboxylic acids and their modified products, or amides formed by the reaction of polyesters having free carboxyl groups with poly(lower alkyleneimines) or their salts, and water-soluble resins or water-soluble polymer compounds such as (meth)acrylic acid-styrene copolymers, (meth)acrylic acid-(meth)acrylate ester copolymers, styrene-maleic acid copolymers, polyvinyl alcohol, or polyvinylpyrrolidone; polyesters; modified polyacrylates; ethylene oxide / propylene oxide addition products, and phosphate esters.

[0033] Commercially available resin-type dispersants include cationic resin dispersants, such as those sold by BYK Chemie under the trade names: DISPER BYK-160, DISPER BYK-161, DISPER BYK-162, DISPER BYK-163, DISPER BYK-164, DISPER BYK-166, DISPER BYK-171, DISPER BYK-182, DISPER BYK-183, DISPER BYK-184, DISPER BYK-185, DISPER BYK-186, DISPER BYK-187, DISPER BYK-188, DISPER BYK-189, DISPER BYK-18 ...9, DISPER BYK-189, DISPER BYK-189, DISPER BYK-189, DISPER BYK-189, DISPER BYK-189, DISPER BYK-184;BASF trade names: EFKA-44, EFKA-46, EFKA-47, EFKA-48, EFKA-4010, EFKA-4050, EFKA-4055, EFKA-4020, EFKA-4015, EFKA-4060, EFKA-4300, EFKA-4330, EFKA-4400, EFKA-4406, EFKA-4510, EFKA-4800;Lubrizol trade names: SOLSPERS-24000, SOLSPERS-32550 , NBZ-4204 / 10; Kawaken Fine Chemical Co., Ltd.'s product names: HINOACT T-6000, HINOACT T-7000, HINOACT T-8000; Ajinomoto Co., Ltd.'s product names: AJISPUR PB-821, AJISPUR PB-822, AJISPUR PB-823; Kyoeisha Chemical Co., Ltd.'s product names: FLORENE DOPA-17HF, FLORENE DOPA-15BHF, FLORENE DOPA-33, FLORENE DOPA-44, and the like.

[0034] 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 the acrylic dispersant.

[0035] The content of the pigment dispersant (a3) ​​is 5 to 60 parts by weight, preferably 15 to 50 parts by weight, based on 100 parts by weight of the pigment (a1). If the content of the pigment dispersant (a3) ​​exceeds 60 parts by weight, the viscosity may increase, whereas if it is less than 5 parts by weight, it may become difficult to atomize the pigment or problems such as gelation after dispersion may occur.

[0036] dye (a2) The dye (a2) may be any dye that is soluble in an organic solvent, and is preferably a dye that is soluble in an organic solvent and has reliability such as solubility in an alkaline developer, heat resistance, and solvent resistance.

[0037] The dye may be selected from acid dyes having an acidic group such as sulfonic acid or carboxylic acid, salts of acid dyes and nitrogen-containing compounds, sulfonamide acid dyes, and derivatives thereof. In addition, azo, xanthene, and phthalocyanine acid dyes and derivatives thereof may also be selected.

[0038] Preferably, the dye is a compound classified as a dye in the Colour Index (published by The Society of Dyers and Colourists) or a known dye as described in Dyeing Notes (Shikisensha).

[0039] Specific examples of the dye include CI solvent dyes: Yellow dyes such as CI Solvent Yellow 4, 14, 15, 16, 21, 23, 24, 38, 56, 62, 63, 68, 79, 82, 93, 94, 98, 99, 151, 162, 163; Red dyes such as CI Solvent Red 8, 45, 49, 89, 111, 122, 125, 130, 132, 146, 179; Orange dyes such as CI Solvent Orange 2, 7, 11, 15, 26, 41, 45, 56, 62; Blue dyes such as CI Solvent Blue 5, 35, 36, 37, 44, 59, 67, 70; Violet dyes such as CI Solvent Violet 8, 9, 13, 14, 36, 37, 47, 49; Examples of green dyes include CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, and 35.

[0040] Among these, CI solvent dyes having excellent solubility in organic solvents are preferred, including CI Solvent Yellow 14, 16, 21, 56, 79, 93, 151; CI Solvent Red 8, 49, 89, 111, 122, 132, 146, 179; CI Solvent Orange 41, 45, 62; CI Solvent Blue 35, 36, 44, 70; and CI Solvent Violet 13, and among these, CI Solvent Yellow 21, 79; CI Solvent Red 8, 122, 132; and CI Solvent Orange 45, 62 are more preferred.

[0041] Also, as a CI 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, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251, and other yellow dyes; 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, red dyes, such as 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, 426; Orange dyes such as CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173; Blue dyes such as CI Acid Blue 1, 7, 9, 15, 18, 23, 25, 27, 29, 40, 42, 45, 51, 62, 70, 74, 80, 83, 86, 87, 90, 92, 96, 103, 112, 113, 120, 129, 138, 147, 150, 158, 171, 182, 192, 210, 242, 243, 256, 259, 267, 278, 280, 285, 290, 296, 315, 324:1, 335, 340; Violet color dyes such as CI Acid Violet 6B, 7, 9, 17, 19, 66; Examples of green dyes include CI Acid Green 1, 3, 5, 9, 16, 25, 27, 50, 58, 63, 65, 80, 104, 105, 106, and 109.

[0042] Among these, among the acid dyes, CI Acid Yellow 42, CI Acid Red 52, 92, CI Acid Blue 80, 90, CI Acid Violet 66, and CI Acid Green 27, which have excellent solubility in organic solvents, are preferable.

[0043] Also, as a CI direct dye, Yellow dyes such as 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, 141; Red dyes such as 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 CI 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, 1 Blue dyes, such as 71, 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, 293; Violet color dyes such as CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; Examples of green dyes include CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, and 82. Also, as a CI mordant dye, Yellow dyes such as CI Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; Red dyes such as CI Modant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 30, 32, 33, 36, 37, 38, 39, 41, 43, 45, 46, 48, 53, 56, 63, 71, 74, 85, 86, 88, 90, 94, 95; Orange dyes such as CI Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; Blue dyes such as CI Mordant Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84; Violet color dyes such as CI Mordant Violet 1, 2, 4, 5, 7, 14, 22, 24, 30, 31, 32, 37, 40, 41, 44, 45, 47, 48, 53, 58; Examples of green dyes include CI Mordant Green 1, 3, 4, 5, 10, 15, 19, 26, 29, 33, 34, 35, 41, 43, and 53.

[0044] In the present invention, the dyes (a2) may be used alone or in combination of two or more kinds.

[0045] The colorant (A) may be contained in an amount of 5 to 60% by weight, preferably 10 to 45% by weight, based on 100% by weight of the total solid content in the colored photosensitive resin composition. When the content of the colorant (A) is within the above range, there is an advantage that the color density of pixels is sufficient when a thin film is formed, and the non-pixel portion does not decrease in the transparency during development, so that no residue is generated.

[0046] In the present invention, the solid content in the colored photosensitive resin composition means the total of the components excluding the solvent.

[0047] Alkali-soluble resin (B) In one embodiment of the present invention, the alkali-soluble resin (B) generally has reactivity due to the action of light or heat and alkali-solubility, and acts as a dispersion medium for the coloring material. The alkali-soluble resin (B) is preferably produced by copolymerizing an ethylenically unsaturated monomer (b1) having a carboxyl group.

[0048] Specific examples of the ethylenically unsaturated monomer (b1) having a carboxyl group include monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, etc.; dicarboxylic acids such as fumaric acid, mesaconic acid, itaconic acid, etc.; anhydrides of these dicarboxylic acids; mono(meth)acrylates of polymers having a carboxyl group and a hydroxyl group at both ends such as ω-carboxypolycaprolactone mono(meth)acrylate, etc. Among these, acrylic acid and methacrylic acid are preferred.

[0049] The alkali-soluble resin (B) may have a hydroxyl group to further ensure developability.

[0050] In order to give hydroxyl groups to the alkali-soluble resin (B), it may be produced by copolymerizing an ethylenically unsaturated monomer (b1) having a carboxyl group with an ethylenically unsaturated monomer (b2) having a hydroxyl group, or by further reacting a copolymer of an ethylenically unsaturated monomer (b1) having a carboxyl group with a compound (b3) having a glycidyl group. It may also be produced by further reacting a copolymer of an ethylenically unsaturated monomer (b1) having a carboxyl group with an ethylenically unsaturated monomer (b2) having a hydroxyl group with a compound (b3) having a glycidyl group.

[0051] Specific examples of the ethylenically unsaturated monomer (b2) having a hydroxyl group include 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, 2-hydroxy-3-phenoxypropyl (meth)acrylate, and N-hydroxyethylacrylamide. Among these, 2-hydroxyethyl (meth)acrylate is preferred. The ethylenically unsaturated monomer (b2) having a hydroxyl group may be used in combination of two or more kinds.

[0052] Specific examples of the compound (b3) having a glycidyl group 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-butylbenzoate, glycidyl stearate, allyl glycidyl ether, and glycidyl methacrylate. Of these, butyl glycidyl ether, allyl glycidyl ether, and glycidyl methacrylate are preferred. Two or more of the compounds (b3) having a glycidyl group may be used in combination.

[0053] In addition, in the production of the alkali-soluble resin (B), the ethylenically unsaturated monomer having a carboxyl group (b1) may be copolymerized with a copolymerizable unsaturated monomer (b4) in addition to the ethylenically unsaturated monomer having a hydroxyl group (b2) and the compound having a glycidyl group (b3).

[0054] Specific examples of the copolymerizable unsaturated monomer (b4) include: Aromatic vinyl compounds such as styrene, vinyltoluene, α-methylstyrene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, o-vinylbenzyl methyl ether, m-vinylbenzyl methyl ether, p-vinylbenzyl methyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, and p-vinylbenzyl glycidyl ether; N-substituted maleimide compounds such as N-cyclohexylmaleimide, N-benzylmaleimide, N-phenylmaleimide, No-hydroxyphenylmaleimide, Nm-hydroxyphenylmaleimide, Np-hydroxyphenylmaleimide, No-methylphenylmaleimide, Nm-methylphenylmaleimide, Np-methylphenylmaleimide, No-methoxyphenylmaleimide, Nm-methoxyphenylmaleimide, and Np-methoxyphenylmaleimide; Alkyl (meth)acrylates such as methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, i-propyl (meth)acrylate, n-butyl (meth)acrylate, i-butyl (meth)acrylate, sec-butyl (meth)acrylate, and t-butyl (meth)acrylate; Cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 ] Alicyclic (meth)acrylates such as decan-8-yl (meth)acrylate, 2-dicyclopentanyloxyethyl (meth)acrylate, and isobornyl (meth)acrylate; Aryl (meth)acrylates such as phenyl (meth)acrylate and benzyl (meth)acrylate; Unsaturated oxetane compounds such as 3-(methacryloyloxymethyl)oxetane, 3-(methacryloyloxymethyl)-3-ethyloxetane, 3-(methacryloyloxymethyl)-2-trifluoromethyloxetane, 3-(methacryloyloxymethyl)-2-phenyloxetane, 2-(methacryloyloxymethyl)oxetane, and 2-(methacryloyloxymethyl)-4-trifluoromethyloxetane are examples.

[0055] The monomers exemplified as the copolymerizable unsaturated monomer (b4) may be used alone or in combination of two or more kinds.

[0056] The method for producing the copolymer is not particularly limited, and may be a conventionally known polymerization method, and among the known polymerization methods, the solution polymerization method is preferred. The polymerization temperature and polymerization time vary depending on the type and ratio of the monomers introduced, the molecular weight and acid value of the desired alkali-soluble resin, and may be, for example, polymerized at 60 to 130°C for 1 to 10 hours.

[0057] When a solvent is used during the polymerization, a solvent used during a normal radical polymerization reaction may be used, specifically, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, ethyl acetate, butyl acetate, propylene glycol monomethyl ether acetate, 3-methoxybutyl acetate, methanol, ethanol, propanol, n-butanol, ethylene glycol monomethyl ether, propylene glycol monomethyl ether, toluene, xylene, ethylbenzene, chloroform, dimethyl sulfoxide, etc. These solvents may be used alone or in combination of two or more.

[0058] The polymerization initiator used in the polymerization may be a commonly used polymerization initiator, and is not particularly limited.Specific examples include organic peroxides such as diisopropylbenzene hydroperoxide, di-t-butyl peroxide, benzoyl peroxide, t-butyl peroxy isopropyl carbonate, t-amyl peroxy-2-ethylhexanoate, and t-butyl peroxy-2-ethylhexanoate; and nitrogen compounds such as 2,2'-azobis(isobutyronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), and dimethyl 2,2'-azobis(2-methylpropionate).These may be used alone or in combination of two or more.

[0059] In the polymerization, a chain transfer agent may be used to control the molecular weight and molecular weight distribution of the copolymer. Examples of the chain transfer agent include mercapto compounds such as n-dodecanethiol, mercaptoacetic acid, and methyl mercaptoacetate; α-methylstyrene dimer, and the like.

[0060] The acid value of the alkali-soluble resin (B) is preferably 30 to 150 mgKOH / g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the polymer, and can usually be determined by titration using an aqueous potassium hydroxide solution. If the acid value of the alkali-soluble resin (B) is less than 30 mgKOH / g, it is difficult for the colored photosensitive resin composition to ensure a sufficient development speed, and if it exceeds 150 mgKOH / g, the adhesion to the substrate decreases, the pattern is likely to short-circuit, and a problem occurs in compatibility with the dye, causing the dye in the colored photosensitive resin composition to precipitate, or the storage stability of the colored photosensitive resin composition decreases, making it easy for the viscosity to increase.

[0061] Also, the alkali-soluble resin preferably has a polystyrene-equivalent weight-average molecular weight (hereinafter, abbreviated as "weight-average molecular weight") of 5,000 to 50,000, preferably 5,000 to 30,000, as measured by gel permeation chromatography (GPC; tetrahydrofuran is used as an elution solvent). When the weight-average molecular weight of the alkali-soluble resin (B) is within the above range, the coating hardness is improved, the residual film rate is high, and the solubility of the unexposed portion in the developer is good, which tends to improve the resolution, and is therefore preferable.

[0062] The molecular weight distribution of the alkali-soluble resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] 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, it is preferable because the developability is excellent.

[0063] The alkali-soluble resin (B) may be contained in an amount of 10 to 80% by weight, preferably 10 to 70% by weight, based on 100% by weight of the total solid content in the colored photosensitive resin composition. When the alkali-soluble resin (B) is contained in the above range, the solubility in the developer is sufficient, making it easy to form a pattern, and the film reduction in the pixel part of the exposed part is prevented during development, resulting in good removability of the non-pixel part, which is preferable.

[0064] Photopolymerizable compound (C) In one embodiment of the present invention, the photopolymerizable compound (C) is a compound that can be polymerized by the action of a photopolymerization initiator (D) described below, and includes a tetrafunctional or higher (meth)acrylic monomer having 45 or more ethylene oxide units of a specific structure added thereto.

[0065] The tetrafunctional or higher (meth)acrylic monomer having 45 or more added ethylene oxide groups is a compound represented by the following chemical formula 1.

[0066] [ka]

[0067] In the above formula, X is an aliphatic hydrocarbon group having 1 to 10 carbon atoms which may or may not contain oxygen or a heteroatom, or A; R 1 is an aliphatic hydrocarbon group having 1 to 10 carbon atoms which may or may not contain oxygen or a heteroatom, R 2 is an aliphatic hydrocarbon group having 1 to 10 carbon atoms, which may or may not contain a heteroatom; A is,

[0068] [ka]

[0069] and R 3 is hydrogen or a methyl group, EO is an ethylene oxide group; n is an integer from 1 to 4, m is an integer from 45 to 96.

[0070] In one embodiment of the present invention, X may be oxygen, alkylene having 1 to 10 carbon atoms, oxyalkylene having 1 to 10 carbon atoms or A, in particular oxygen or A.

[0071] In one embodiment of the present invention, R 1may be oxygen, alkylene having 1 to 10 carbon atoms or oxyalkylene having 1 to 10 carbon atoms, in particular a methylene group.

[0072] In one embodiment of the present invention, R 2 may be an alkylene group having 1 to 10 carbon atoms or an oxyalkylene group having 1 to 10 carbon atoms, and in particular may be a methylene group.

[0073] In one embodiment of the present invention, as described above, m may be an integer of 45 to 96. If m is an integer less than 45, the developability may decrease or residue may be generated during formation of an ultra-high resolution pattern, and if m is an integer greater than 96, the adhesion may be insufficient, causing pattern peeling.

[0074] Commercially available products of the tetrafunctional or higher (meth)acrylic polyfunctional monomer having ethylene oxide added thereto, represented by the above chemical formula 1, include A-DPH-48E and A-DPH-96E manufactured by Shin-Nakamura Kogyo Co., Ltd.

[0075] The tetrafunctional or higher (meth)acrylic polyfunctional monomer having ethylene oxide added thereto, represented by Chemical Formula 1, may be contained in an amount of 10 to 50% by weight, preferably 20 to 40% by weight, based on 100% by weight of the total photopolymerizable compound. If the content of the tetrafunctional or higher (meth)acrylic polyfunctional monomer having ethylene oxide added thereto, represented by Chemical Formula 1, is less than the above range, the developability may be insufficient during the formation of an ultra-high resolution pattern, resulting in the generation of residues, and if the content exceeds the above range, the adhesion may be insufficient during the formation of an ultra-high resolution pattern, resulting in the generation of pattern peeling.

[0076] In one embodiment of the present invention, the photopolymerizable compound may further include a trifunctional or higher (meth)acrylic monomer. The trifunctional or higher (meth)acrylic monomer may be a trifunctional to hexafunctional (meth)acrylic monomer.

[0077] For example, examples of the tri- or higher functional (meth)acrylic 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(meth)acrylate, and dipentaerythritol hexa(meth)acrylate, but are not limited thereto.

[0078] The trifunctional or higher (meth)acrylic monomer may be contained in an amount of 50 to 90% by weight, preferably 60 to 80% by weight, based on 100% by weight of the total photopolymerizable compound. If the content of the trifunctional or higher (meth)acrylic monomer is less than 50% by weight, the adhesion may be insufficient during the formation of an ultra-high resolution pattern, causing peeling of the pattern, and if it exceeds 90% by weight, the developability may be insufficient during the formation of an ultra-high resolution pattern, causing residues.

[0079] In one embodiment of the present invention, the photopolymerizable compound may be contained in an amount of 5 to 80% by weight, preferably 20 to 60% by weight, and more preferably 30 to 50% by weight, based on 100% by weight of the total solid content in the colored photosensitive resin composition. When the photopolymerizable compound is contained in the above range, the strength and smoothness of the pixel part may be improved, and the pattern characteristics may be improved when a super high resolution pattern is formed.

[0080] Photoinitiator (D) In one embodiment of the present invention, the photopolymerization initiator (D) may be used without any particular limitation as long as it can polymerize the photopolymerizable compound (C). The photopolymerization initiator (D) is preferably one or more compounds selected from the group consisting of acetophenone-based compounds, benzophenone-based compounds, triazine-based compounds, biimidazole-based compounds, oxime-based compounds, and thioxanthone-based compounds from the viewpoints of polymerization characteristics, initiation efficiency, absorption wavelength, availability, price, etc., and in particular, it is preferable to use an oxime-based compound from the viewpoint of pattern characteristics when forming an ultra-high resolution pattern.

[0081] Specific examples of the acetophenone-based compound include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyl dimethyl ketal, 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methylpropan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-(4-methylthiophenyl)-2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butan-1-one, 2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propan-1-one, and 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4-morpholinophenyl)butan-1-one.

[0082] Examples of the benzophenone-based compounds include benzophenone, 0-benzoylmethylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone.

[0083] Specific examples of the biimidazole-based compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole, 2,2-bis(2,6-dichlorophenyl)-4,4'5,5'-tetraphenyl-1,2'-biimidazole, and biimidazole compounds in which the phenyl groups at the 4,4',5,5' positions are substituted with carboalkoxy groups. Among these, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, and 2,2-bis(2,6-dichlorophenyl)-4,4'5,5'-tetraphenyl-1,2'-biimidazole are preferably used.

[0084] Specific examples of the triazine-based 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, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine. [2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan)-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine, and the like.

[0085] Examples of the oxime compounds include 1,2-octanedione, 1-[4-(phenylthio)phenyl]-,2-(O-benzoyloxime), ethanone 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-1-(O-acetyloxime), and the like. Commercially available products include TR-PBG-305 (TRONLY), OXE-01 (BASF), and OXE-02 (BASF).

[0086] Examples of the thioxanthone compounds include 2-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0087] In addition, the photopolymerization initiator (D) may be used in combination with a photopolymerization initiator assistant (d1) in order to improve the sensitivity of the colored photosensitive resin composition of the present invention. By containing the photopolymerization initiator assistant (d1), the colored photosensitive resin composition of the present invention can further increase the sensitivity and improve the productivity.

[0088] The photopolymerization initiation assistant (d1) may preferably be, for example, one or more compounds selected from the group consisting of amine compounds, carboxylic acid compounds, and organic sulfur compounds having a thiol group.

[0089] Specific examples of the amine compound that can be used include aliphatic amine compounds such as triethanolamine, methyldiethanolamine, and triisopropanolamine; and aromatic amine compounds such as methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), and 4,4'-bis(diethylamino)benzophenone. In particular, it is preferable to use an aromatic amine compound.

[0090] The carboxylic acid compound is preferably an aromatic heteroacetic acid, and specific examples thereof include phenylthioacetic acid, methylphenylthioacetic acid, ethylphenylthioacetic acid, methylethylphenylthioacetic acid, dimethylphenylthioacetic acid, methoxyphenylthioacetic acid, dimethoxyphenylthioacetic acid, chlorophenylthioacetic acid, dichlorophenylthioacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0091] 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)-trione, trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptobutyrate), pentaerythritol tetrakis(3-mercaptopropionate), dipentaerythritol hexakis(3-mercaptopropionate), and tetraethylene glycol bis(3-mercaptopropionate).

[0092] The photopolymerization initiator (D) may be contained in an amount of 0.1 to 40 parts by weight, preferably 1 to 30 parts by weight, relative to 100 parts by weight of the total amount of the alkali-soluble resin (B) and the photopolymerizable compound (C). When the photopolymerization initiator (D) is contained in the above range, the colored photosensitive resin composition of the present invention becomes highly sensitive and the exposure time is shortened, which is preferable because it improves productivity and maintains high resolution. In addition, the strength of the pixel part formed using the composition under the above-mentioned conditions and the smoothness of the surface of the pixel part may be improved.

[0093] In addition, when the photopolymerization initiator assistant (d1) is further used, the photopolymerization initiator assistant (d1) may be contained in an amount of 0.1 to 40 parts by weight, preferably 1 to 30 parts by weight, per 100 parts by weight of the total amount of the alkali-soluble resin (B) and the photopolymerizable compound (C). When the photopolymerization initiator assistant (d1) is contained in the above range, the sensitivity of the colored photosensitive resin composition is further increased, and the productivity of the color filter formed using the composition may be improved.

[0094] Solvent (E) In one embodiment of the present invention, the solvent (E) may be any solvent used in a typical colored photosensitive resin composition, without any particular limitation, so long as it is effective in dissolving other components contained in the colored photosensitive resin composition. In particular, ethers, aromatic hydrocarbons, ketones, alcohols, esters, amides, and the like are preferred.

[0095] Specific 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; propylene glycol monomethyl ether acetate, and propylene glycol monoethyl ether. Examples of the alkylene glycol alkyl ether acetates include 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 lactate, butyl lactate, ethyl 3-ethoxypropionate, and methyl 3-methoxypropionate, and cyclic esters such as γ-butyrolactone.

[0096] The solvent (E) is preferably an organic solvent having a boiling point of 100° C. to 200° C. in terms of coatability and drying property, and more preferably, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, ethyl lactate, butyl lactate, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, or the like may be used.

[0097] In one embodiment of the present invention, the solvent (E) may be contained in an amount of 60 to 90% by weight, preferably 65 to 85% by weight, based on 100% by weight of the total colored photosensitive resin composition. When the solvent (E) is contained in the above range, the coatability may be improved when the composition is coated with a coating device such as a roll coater, a spin coater, a slit and spin coater, a slit coater (sometimes called a die coater), or an inkjet.

[0098] Additives (F) In addition to the above-mentioned components, the colored photosensitive resin composition according to one embodiment of the present invention may also contain additives (F) such as fillers, other polymer compounds, curing agents, surfactants, adhesion promoters, ultraviolet absorbers, and anti-aggregation agents, as needed by those skilled in the art, within the scope of the object of the present invention.

[0099] The filler may be specifically glass, silica, alumina, etc., but is not limited thereto.

[0100] Specific examples of the other polymer compounds that can be used include thermosetting resins such as epoxy resins and maleimide resins, and thermoplastic resins such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl acrylate, polyester, and polyurethane, but are not limited thereto.

[0101] The curing agent is used to enhance deep curing and mechanical strength, and may be specifically, but not limited to, an epoxy compound, a polyfunctional isocyanate compound, a melamine compound, an oxetane compound, etc. The epoxy compound may be specifically, but not limited to, a bisphenol A epoxy resin, a hydrogenated bisphenol A epoxy resin, a bisphenol F epoxy resin, a hydrogenated bisphenol F epoxy resin, a novolac epoxy resin, other aromatic epoxy resins, an alicyclic epoxy resin, a glycidyl ester resin, a glycidyl amine resin, or a brominated derivative of such an epoxy resin, an aliphatic, alicyclic or aromatic epoxy compound other than an epoxy resin and its brominated derivative, an epoxidized butadiene (co)polymer, an epoxidized isoprene (co)polymer, a glycidyl (meth)acrylate (co)polymer, a triglycidyl isocyanurate, etc. The oxetane compound may be specifically, but is not limited to, carbonate bisoxetane, xylene bisoxetane, adipate bisoxetane, terephthalate bisoxetane, cyclohexanedicarboxylate bisoxetane, and the like.

[0102] The curing agent may be used in combination with a curing auxiliary compound capable of ring-opening polymerization of the epoxy group of an epoxy compound and the oxetane skeleton of an oxetane compound. Specific examples of the curing auxiliary compound include polyvalent carboxylic acids, polyvalent carboxylic anhydrides, and acid generators. The carboxylic anhydrides may be commercially available epoxy resin curing agents. Examples of commercially available epoxy resin curing agents include those under the trade name (ADEKA HARDNER EH-700) (manufactured by ADEKA INDUSTRIES CO., LTD.), the trade name (RIKACID HH) (manufactured by Shin Nippon Rika Co., Ltd.), and the trade name (MH-700) (manufactured by Shin Nippon Rika Co., Ltd.). The curing agents and curing auxiliary compounds exemplified above may be used alone or in combination of two or more kinds.

[0103] The surfactant may be used to further improve the film-forming properties of the colored photosensitive resin composition of the present invention, and a fluorine-based surfactant, a silicone-based surfactant, or the like may be preferably used.

[0104] Examples of the silicone surfactant include commercially available products such as DC3PA, DC7PA, SH11PA, SH21PA, and SH8400 manufactured by Dow Corning Toray Silicones, and TSF-4440, TSF-4300, TSF-4445, TSF-4446, TSF-4460, and TSF-4452 manufactured by GE Toshiba Silicones. Examples of the fluorine surfactant include commercially available products such as Megafac F-470, F-471, F-475, F-482, F-489, and F-554 manufactured by Dainippon Ink and Chemicals, Inc.

[0105] The above-exemplified surfactants may be used alone or in combination of two or more kinds.

[0106] Specifically, the adhesion promoter may be selected from the group consisting of vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane, and 3-isocyanatopropyltriethoxysilane, either alone or in combination. The adhesion promoter may be contained in an amount of 0.01 to 10% by weight, preferably 0.05 to 2% by weight, relative to 100% by weight of the total solid content in the colored photosensitive resin composition.

[0107] The ultraviolet absorbing agent may be specifically 2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chlorobenzotriazole, alkoxybenzophenone, or the like, but is not limited thereto.

[0108] The anti-agglomerating agent may be, specifically, sodium polyacrylate, but is not limited thereto.

[0109] The colored photosensitive resin composition according to one embodiment of the present invention can be produced, for example, by the following method.

[0110] First, the pigment (a1) of the colorant (A) is mixed with the solvent (E) and dispersed using a bead mill or the like until the average particle size of the pigment becomes about 0.2 μm or less. At this time, if necessary, the pigment dispersant (a3), a part or all of the alkali-soluble resin (B), or the dye (a2) may be mixed with the solvent (E) to dissolve or disperse it. The remaining alkali-soluble resin (B), the photopolymerization initiator (D), the photopolymerizable compound (C), and the additive (F), and if necessary, the solvent (E) are further added to the mixed dispersion to a predetermined concentration, thereby producing the colored photosensitive resin composition according to the present invention.

[0111] One embodiment of the present invention relates to a color filter formed using the above-mentioned colored photosensitive resin composition. The color filter according to one embodiment of the present invention is characterized by including a color layer formed by applying the above-mentioned colored photosensitive resin composition on a substrate, exposing the same to light in a predetermined pattern, and developing the same.

[0112] The pattern forming method using the colored photosensitive resin composition of the present invention will be described in detail below.

[0113] The method for forming a pattern using the colored photosensitive resin composition of the present invention may be a method known in the art, but typically includes a coating step, an exposure step, and a removal step. The colored photosensitive resin composition of the present invention is coated on a substrate, and photocured and developed to form a pattern, which can be used as a colored pixel (colored image).

[0114] Specifically, the colored photosensitive resin composition is applied to a thickness of 2.0 to 3.4 μm on a glass substrate that is not coated with anything or a glass substrate that is coated with a SiNx (protective film) to a thickness of 500 to 1,500 Å by a suitable method such as spin coating or slit coating. After coating, light is irradiated to form a pattern required for the color filter. After light irradiation, the coating layer is treated with an alkaline developer to dissolve the non-irradiated part of the coating layer and form a pattern required for the color filter. This process is repeated for the number of required R, G, and B colors to obtain a color filter having a desired pattern. In addition, in the above process, the image pattern obtained by development is heated again or cured by irradiation with active rays, etc., to further improve crack resistance, solvent resistance, etc.

[0115] One embodiment of the present invention relates to an image display device including the above-mentioned color filter.

[0116] The color filter of the present invention can be applied to various image display devices such as not only conventional liquid crystal display devices (LCDs) but also electroluminescence display devices (ELs), plasma display devices (PDPs), field emission displays (FEDs), and organic light emitting devices (OLEDs).

[0117] The image display device of the present invention includes a configuration known in the art, except for the inclusion of the above-mentioned color filter.

[0118] The present invention will be described in more detail below with reference to examples, comparative examples, and experimental examples. It will be obvious to those skilled in the art that these examples, comparative examples, and experimental examples are merely for the purpose of explaining the present invention, and the scope of the present invention is not limited thereto.

[0119] Production Example 1: Production of Pigment Dispersion A-1 12.0 parts by weight of CI Pigment Blue 15:6, 1.8 parts by weight of CI Acid Red 52, 4.0 parts by weight of BYK-2001 as a pigment dispersant, and 82.2 parts by weight of propylene glycol monomethyl ether acetate were mixed and dispersed in a bead mill for 12 hours to produce pigment dispersion A-1.

[0120] Synthesis Example 1: Synthesis of alkali-soluble resin (B-1) Into a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping funnel, and a nitrogen inlet tube, 120 parts by weight of propylene glycol monomethyl ether acetate, 80 parts by weight of propylene glycol monomethyl ether, 2 parts by weight of AIBN, 19 parts by weight of acrylic acid, 10 parts by weight of benzyl methacrylate, 51 parts by weight of styrene, and 3 parts by weight of n-dodecyl mercaptan were put and replaced with nitrogen. Then, the mixture was stirred and the temperature was raised to 110°C and reacted for 6 hours. Next, the temperature of the reaction liquid was lowered to room temperature, the air in the flask was replaced with general air, and then 0.3 parts by weight of triethylamine and 20 parts by weight of glycidyl methacrylate were put in and reacted at 110°C for 5 hours to produce an alkali-soluble resin (solid content 60% by weight). The acid value of the solid content of the alkali-soluble resin synthesized in this way was 80 mgKOH / g, and the weight average molecular weight (Mw) measured by GPC was about 22,000.

[0121] Examples 1 to 6 and Comparative Examples 1 to 6: Production of colored photosensitive resin compositions A colored photosensitive resin composition was produced by mixing the components according to the composition in Table 1 below (unit: parts by weight).

[0122] [Table 1]

[0123] A-1: Pigment dispersion of Production Example 1 B-1: Alkali-soluble resin of Synthesis Example 1 C-1: Trimethylolpropane triacrylate (trifunctional (meth)acrylic monomer, A-TMPT, Shin-Nakamura Kogyosha) C-2: Dipentaerythritol hexaacrylate (hexafunctional (meth)acrylic monomer, A-9550, Shin-Nakamura Kogyosha) C-3: Compound in which m is 48 in Chemical Formula 1 (6 functional groups, A-DPH-48E, Shin-Nakamura Kogyosha) C-4: Compound in which m is 96 in Chemical Formula 1 (6 functional groups, A-DPH-96E, Shin-Nakamura Kogyosha) C-5: Compound in which m is 24 in Chemical Formula 1 (6 functional groups, A-DPH-24E, Shin-Nakamura Kogyosha) C-6: 1,6-Hexanediol diacrylate (A-HD-N, Shin-Nakamura Kogyosha) D-1: Ethanone 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-1-(O-acetyloxime) (Irgacure OXE-02, BASF) E-1: Propylene glycol monomethyl ether acetate Experimental Example 1 Color filters were manufactured using the colored photosensitive resin compositions prepared in the Examples and Comparative Examples as described below. The physical properties of the color filters were measured as described below. The results are shown in Table 2 below.

[0124] <Manufacturing of color filters> The colored photosensitive resin composition was applied onto a glass substrate by spin coating, and the glass substrate was placed on a heating plate and maintained at a temperature of 100°C for 3 minutes to form a thin film. Next, a test photomask having a line / space pattern of 1 μm to 10 μm was placed on the thin film, and ultraviolet light was irradiated. At this time, a 1KW high-pressure mercury lamp containing g, h, and i rays was used as the ultraviolet light source, and the intensity was 100 mJ / cm. 2No special optical filter was used. The thin film irradiated with UV light was developed by the puddle method using a developing solution of KOH aqueous solution with pH 10.5. The glass substrate coated with the thin film was washed with distilled water, dried by blowing nitrogen gas, and heated in a heating oven at 230°C for 5 minutes to produce a color filter.

[0125] (1) Adhesion The generated pattern was observed under an optical microscope and evaluated based on the degree of peeling that occurred in the pattern image, according to the following evaluation criteria.

[0126] <Evaluation criteria> ○: No peeling in the pattern image △: 1 to 5 peelings in the pattern image ×: More than 5 peeled areas in the pattern image (2) Residue of the lower substrate According to the following evaluation criteria, the degree of undevelopedness on the lower substrate was evaluated when the non-patterned portion of the produced color filter was observed under an optical microscope.

[0127] <Evaluation criteria> ○: No residue △: Residue is present on part of the lower substrate ×: Residue present on the entire lower substrate (3) Uneven development Distilled water was dropped onto the substrate, and the substrate was left at room temperature for 2 minutes, after which nitrogen gas was sprayed onto the substrate to dry it.Then, the substrate was irradiated with a Na lamp, and the surface condition of the coating film was observed to visually judge whether or not unevenness occurred, and the development unevenness was evaluated according to the following evaluation criteria.

[0128] <Evaluation criteria> ○: No circular water stains are visible on the coating surface △: Small circular water stains are visible on the coating surface. ×: Water stains are clearly visible on the coating surface.

[0129] [Table 2]

[0130] As shown in Table 2, the colored photosensitive resin compositions of Examples 1 to 6, which contain a tetrafunctional or higher (meth)acrylic monomer having 45 or more ethylene oxide units of a specific structure added thereto as the photopolymerizable compound according to the present invention in an amount of 10 to 50% by weight based on 100% by weight of the total photopolymerizable compound, have excellent adhesion when forming ultrafine patterns, and do not cause residues or uneven development on the underlying substrate.

[0131] In contrast, the colored photosensitive resin compositions of Comparative Examples 1 to 5, which did not contain a tetrafunctional or higher (meth)acrylic monomer having 45 or more added ethylene oxide units of a specific structure, or which had a content outside the range, were found to have reduced adhesion during the formation of ultrafine patterns, or to have residues on the lower substrate and / or uneven development. Meanwhile, the colored photosensitive resin composition of Comparative Example 6, which used a (meth)acrylic monomer with less than three functionalities, showed results such as insufficient adhesion and the occurrence of pattern peeling.

[0132] Although specific parts of the present invention have been described in detail above, it is clear to those skilled in the art that such specific descriptions are merely preferred embodiments and do not limit the scope of the present invention. Those skilled in the art will be able to make various applications and modifications within the scope of the present invention based on the above contents.

[0133] Therefore, the true scope of the invention is to be defined by the following claims and their equivalents.

Claims

1. A colored photosensitive resin composition for a color filter, comprising a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent, The photopolymerizable compound is a colored photosensitive resin composition containing a tetrafunctional or higher (meth)acrylic monomer having ethylene oxide added thereto, represented by the following chemical formula 1, in an amount of 20 to 40% by weight based on 100% by weight of the total photopolymerizable compound, and a trifunctional or higher (meth)acrylic monomer in an amount of 60 to 80% by weight based on 100% by weight of the total photopolymerizable compound. 【Chemistry 1】 In the above formula, X is an aliphatic hydrocarbon group having 1 to 10 carbon atoms which may or may not contain oxygen or heteroatoms, or A; R １ is an aliphatic hydrocarbon group having 1 to 10 carbon atoms which may or may not contain oxygen or a heteroatom, R ２ is an aliphatic hydrocarbon group having 1 to 10 carbon atoms, which may or may not contain a heteroatom, A is, 【Chemistry 2】 and R ３ is hydrogen or a methyl group, EO is an ethylene oxide group; n is an integer from 1 to 4, The sum of m is an integer from 45 to 96.

2. 2. The colored photosensitive resin composition according to claim 1, wherein the photopolymerizable compound is contained in an amount of 5 to 80% by weight based on 100% by weight of the total solid content in the colored photosensitive resin composition.

3. The colored photosensitive resin composition according to claim 1 , wherein the photopolymerization initiator comprises an oxime-based photopolymerization initiator.

4. A color filter formed using the colored photosensitive resin composition according to any one of claims 1 to 3.

5. An image display device comprising the color filter according to claim 4.

Images