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

Abstract

To provide a colored photosensitive resin composition which can achieve a fine colored pattern excellent in pattern adhesion and residue characteristics in light exposure using an ultrashort-wavelength exposing device of 300 nm or less and has high resolution.SOLUTION: A colored photosensitive resin composition is provided, including a coloring agent, alkali-soluble resin, a photopolymerization initiator, a photopolymerizable compound, and a solvent, wherein the photopolymerization initiator includes a compound represented by a specific chemical formula.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 exhibits excellent pattern adhesion and residue characteristics during exposure using an ultrashort wavelength exposure device of 300 nm or less, thereby realizing high-resolution, fine colored patterns; a color filter formed using the same; and an image display device equipped with the color filter. [Background technology]

[0002] A solid-state image sensor is an element that converts an image captured by light energy into electrical information, and may include a color filter at the bottom of the lens. For example, CMOS image sensors (CIS) employ fine-pitch color filters that are patterned with higher resolution than the color filters corresponding to pixels in typical display devices. The color filters in a CIS usually have a coloring pattern of three primary colors: red (R), green (G), and blue (B), and play the role of decomposing transmitted light into these three primary colors.

[0003] The colored pattern is formed using a colored photosensitive resin composition containing a pigment or dye. The processing of the colored pattern using the colored photosensitive resin composition is usually carried out in a lithography process, and a light source using g-line (wavelength 436 nm) or i-line (wavelength 365 nm) is generally used.

[0004] In recent years, solid-state image sensors used in digital cameras and other devices have been required to further reduce pixel size in order to increase pixel count and improve image quality. Consequently, color patterns also need to be made ultra-fine and thinner. However, it can be said that the size of patterns that can be realized with light sources using wavelengths in the 463-365nm range, which are used to form existing color patterns, has reached its limit.

[0005] To overcome these limitations, research has been conducted on forming patterns using light sources with ultrashort wavelengths of 300 nm or less. However, this leads to problems such as increased colorant content in the colored photosensitive resin composition, reduced adhesion between the colored film and the support, difficulty in ensuring pattern characteristics, and the generation of residue.

[0006] Therefore, there has been a need to develop a colored photosensitive resin composition that is highly sensitive to ultrashort wavelength light sources and also exhibits excellent pattern characteristics such as residue or residual film properties, as well as developability and adhesion, in order to enable fine patterning.

[0007] Korean Published Patent No. 10-2009-0072754 discloses a color filter composition containing a pigment and a binder resin, but it is unsuitable for application to the high-resolution solid-state image sensor color filter mentioned above. [Overview of the project] [Problems that the invention aims to solve]

[0008] One objective of the present invention is to provide a colored photosensitive resin composition that exhibits excellent pattern adhesion and residue characteristics during exposure using an ultrashort wavelength exposure device of 300 nm or less, and can realize high-resolution, fine colored patterns.

[0009] Another object of the present invention is to provide a colored pattern formed using the colored photosensitive resin composition.

[0010] Another object of the present invention is to provide a color filter including the aforementioned coloring pattern.

[0011] A further object of the present invention is to provide an image display device equipped with the color filter.

[0012] A further object of the present invention is to provide a solid-state image sensor equipped with the color filter. [Means for solving the problem]

[0013] On the one hand, the present invention provides a colored photosensitive resin composition containing a colorant, an alkali-soluble resin, a photopolymerization initiator, a photopolymerizable compound, and a solvent, wherein the photopolymerization initiator contains a compound represented by the following chemical formula 1 and a compound represented by the following chemical formula 2.

[0014]

Chemical formula

[0015] In the above formula, R , , , , ,

[0019] , ,

[0018] , , 4 ,

[0021] , , ,

[0020] , , is -(CH2) n R 4 and R 2 is an alkyl group of C1-C 20 and R 3 is

[0016]

Chemical formula

[0017] and R 4 is hydrogen or a C3-C6 cycloalkyl group, n is an integer from 1 to 5.

[0018] In one embodiment of the present invention, the weight ratio of the compound represented by the chemical formula 1 and the compound represented by the chemical formula 2 may be 25:75 to 85:15.

[0019] The colored photosensitive resin composition according to one embodiment of the present invention may be used for manufacturing a color filter of a solid-state imaging device using an ultra-short wavelength exposure device of 300 nm or less.

[0020] In one embodiment of the present invention, the ultra-short wavelength exposure device of 300 nm or less may be a KrF scanner exposure device.

[0021] On the other hand, the present invention provides a colored pattern formed using the colored photosensitive resin composition.

[0022] On the other hand, the present invention also provides a color filter including the aforementioned coloring pattern.

[0023] On the other hand, the present invention also provides an image display device characterized by being equipped with the aforementioned color filter.

[0024] On the other hand, the present invention provides a solid-state image sensor characterized by being equipped with the aforementioned color filter.

[0025] In one embodiment of the present invention, the solid-state image sensor may include a CMOS image sensor. [Effects of the Invention]

[0026] The colored photosensitive resin composition according to the present invention contains a photopolymerization initiator comprising a carbazole compound and an acetophenone compound of a specific structure, enabling the creation of high-resolution, fine colored patterns with excellent pattern adhesion and residue characteristics when exposed using an ultrashort wavelength exposure device of 300 nm or less. [Modes for carrying out the invention]

[0027] The present invention will be described in more detail below.

[0028] One embodiment of the present invention relates to a colored photosensitive resin composition comprising a colorant (A), an alkali-soluble resin (B), a photopolymerization initiator (C), a photopolymerizable compound (D), and a solvent (E), wherein the photopolymerization initiator (C) comprises a carbazole compound and an acetophenone compound of a specific structure.

[0029] The following describes in detail, component by component, a colored photosensitive resin composition according to one embodiment of the present invention.

[0030] [Coloring agent (A)] In one embodiment of the present invention, the colorant (A) may be an organic pigment, an inorganic pigment, or a dye commonly used in the art.

[0031] The aforementioned organic pigment may be any of the various pigments used in printing inks, inkjet inks, etc. Specifically, examples include phthalocyanine water-soluble azo pigments, insoluble azo pigments, phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, isoindoline pigments, perylene pigments, perinone pigments, dioxazine pigments, anthraquinone pigments, diantraquinonyl pigments, anthrapyrimidine pigments, anthanthrone pigments, indanthrone pigments, flavanthrone pigments, pyranthrone pigments, or diketopyrrolopyrrole pigments.

[0032] The aforementioned pigment may be subjected to, if necessary, resin treatment, surface treatment using pigment derivatives into which acidic or basic groups have been introduced, grafting treatment of the pigment surface with polymer compounds, atomization treatment by sulfuric acid atomization method, washing treatment with organic solvents or water to remove impurities, or treatment to remove ionic impurities by ion exchange method.

[0033] Examples of the inorganic pigments include metal compounds such as metal oxides and metal complex salts, and specifically include metal oxides or complex metal oxides such as iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, antimony, or carbon black.

[0034] The pigments used in the present invention may be organic or inorganic pigments commonly used in the field, and these may be used individually or in combination of two or more.

[0035] In particular, the aforementioned pigments may be compounds classified as pigments in the Color Index (published by The Society of Dyers and Colourists), and more specifically, pigments with the following Color Index (CI) numbers may be used, but are not necessarily limited to these.

[0036] CI Pigment Yellow 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 180, 185, and 242 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, 215, 216, 224, 242, 254, 255, 264, and 277 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, 58, 59, 62, and 63 CI Pigment Brown 28 CI Pigment Black 1 and 7, etc. Among the exemplified CI pigment pigments, it is preferable to use 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 166, CI Pigment Red 177, CI Pigment Red 242, CI Pigment Red 254, CI Pigment Red 255, CI Pigment Violet 23, CI Pigment Blue 15:6, CI Pigment Green 7, CI Pigment Green 36, or CI Pigment Green 58.

[0037] It is preferable to use a pigment dispersion in which the pigment particles are uniformly dispersed. One example of a method for uniformly dispersing the pigment particles is a method of dispersing the pigment by including a pigment dispersant, and by this method, a pigment dispersion can be obtained in which the pigment is uniformly dispersed in the solution.

[0038] Examples of the aforementioned pigment dispersants include cationic, anionic, nonionic, positive, polyester, and polyamine surfactants, which may be used individually or in combination of two or more.

[0039] Specific examples of the aforementioned surfactants include polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyethylene glycol diesters, sorbitan fatty acid esters, fatty acid modified polyesters, tertiary amine modified polyurethanes, polyethyleneimines, and others. Other examples of trade names include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), POLYFLOW (manufactured by Kyoeisha Chemical Co., Ltd.), EFTOP (manufactured by Tochem Products), MEGAFAC (manufactured by Dainippon Ink and Chemicals, Inc.), Flourad (manufactured by Sumitomo 3M Co., Ltd.), Asahi guard, Surflon (manufactured by Asahi Glass Co., Ltd.), SOLSPERSE (manufactured by Zeneca Co., Ltd.), EFKA (manufactured by EFKA Chemicals), and PB 821 (manufactured by Ajinomoto Co., Inc.).

[0040] The pigment dispersant is usually used in an amount of 1 part by weight or less per 1 part by weight of pigment, and preferably in the range of 0.05 to 0.5 parts by weight. When the pigment dispersant is used in the above-mentioned content, it is preferable because a pigment with a uniform particle size can be obtained.

[0041] The aforementioned dye may be used without particular limitations as long as it is soluble in organic solvents. Preferably, a dye may be used that is soluble in organic solvents and can also ensure reliability in terms of solubility in alkaline developers, heat resistance, solvent resistance, etc.

[0042] The aforementioned dyes may be selected from acidic dyes having acidic groups such as sulfonic acid and carboxylic acid, salts of acidic dyes and nitrogen-containing compounds, sulfonamide forms of acidic dyes, and derivatives thereof. In addition, azo, xanthene, and phthalocyanine acidic dyes and their derivatives can also be selected.

[0043] Preferably, the dyes include compounds classified as dyes in the Color Index (published by The Society of Dyers and Colourists) and known dyes listed in the Dyeing Notes (published by Irozome Co., Ltd.).

[0044] Specific examples of the aforementioned dyes include CI solvent dyes, CI Solvent Yellow 4, 14, 15, 21, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 162 and other yellow dyes; CI Solvent Red 8, 45, 49, 122, 125, 130 and other red dyes; Orange dyes such as CI Solvent Orange 2, 7, 11, 15, 26, 56; CI Solvent Blue 35, 37, 59, 67, and other blue dyes; Examples of CI Solvent Greens include green dyes such as 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, and 35.

[0045] 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, Yellow dyes such as 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, etc. 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, 2 Red dyes such as 11, 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; CI Acid Blue blue dyes such as 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, etc. CI Acid Violet 6B, 7, 9, 17, 19, and other violet dyes; 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.

[0046] Also, as a CI direct dye, CI Direct Yellow yellow dyes such as 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, etc. CI Direct Red red dyes such as 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, etc. CI Direct Orange orange dyes such as 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, 17 Blue dyes such as 1, 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, etc. CI Direct Violet, violet dyes such as 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104, etc. 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.

[0047] Also, as a CI modant dye, CI Mordant Yellow yellow dyes such as 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; 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 and other red dyes; CI Mordant Orange orange dyes such as 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; CI Mordant Blue blue dyes such as 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, etc. CI Mordant Violet 1, 2, 4, 5, 7, 14, 22, 24, 30, 31, 32, 37, 40, 41, 44, 45, 47, 48, 53, 58, and other violet-colored dyes; Examples of green dyes include CI Mordant Green 1, 3, 4, 5, 10, 15, 19, 26, 29, 33, 34, 35, 41, 43, and 53.

[0048] The aforementioned pigments or dyes may be used in combination of one or more types.

[0049] The coloring agent (A) may be present in an amount of 5 to 80% by weight, preferably 30 to 70% by weight, based on 100% by weight of the total solid content in the colored photosensitive resin composition. When the content of the coloring agent (A) is within the above range, the color density of the pixels becomes sufficient during thin film formation, and the loss of non-pixel areas does not decrease during development, resulting in no residue.

[0050] In the present invention, the solid content in the colored photosensitive resin composition refers to the total sum of the components after the solvent has been removed.

[0051] [Alkali-soluble resin (B)] In one embodiment of the present invention, the alkali-soluble resin (B) may be selected from resins known in the art without particular limitation, as long as it has reactivity in response to light and heat, alkali solubility, acts as a dispersion medium for solid components containing a colorant, and performs the function of a binder resin.

[0052] Specifically, the alkali-soluble resin (B) is preferably a copolymer of an unsaturated carboxyl group-containing monomer and another monomer copolymerizable therewith.

[0053] Examples of the unsaturated carboxyl group-containing monomers include unsaturated monocarboxylic acids, unsaturated dicarboxylic acids, unsaturated tricarboxylic acids, and other unsaturated carboxylic acids having one or more carboxyl groups in their molecules.

[0054] Examples of the unsaturated monocarboxylic acid include acrylic acid, methacrylic acid, crotonic acid, α-chloroacrylic acid, and cinnamic acid. Examples of the unsaturated dicarboxylic acid include maleic acid, fumaric acid, itaconic acid, citraconic acid, and mesaconic acid. The unsaturated polycarboxylic acid may also be an acid anhydride, specifically maleic anhydride, itaconic anhydride, and citraconic anhydride. Furthermore, the unsaturated polycarboxylic acid may also be its mono(2-methacryloyloxyalkyl) ester, for example, mono(2-acryloyloxyethyl) succinate, mono(2-methacryloyloxyethyl) succinate, mono(2-acryloyloxyethyl) phthalate, and mono(2-methacryloyloxyethyl) phthalate. The unsaturated polycarboxylic acid may also be a mono(meth)acrylate of the dicarboxyl polymer at both ends, for example, ω-carboxypolycaprolactone monoacrylate, ω-carboxypolycaprolactone monomethacrylate, and the like.

[0055] The carboxyl group-containing monomers may be used individually or in combination of two or more types.

[0056] Examples of other monomers copolymerizable with the carboxyl group-containing monomer include, for example, 3,4-epoxytricyclo[5.2.1.0 2,6 dec-9-yl acrylate, 3,4-epoxytricyclo[5.2.1.0 2,6Epoxy (meth)acrylate compounds such as decane-8-yl acrylate, glycidyl methacrylate, and 4-hydroxybutyl acrylate glycidyl ether; aromatic vinyl compounds such as styrene, α-methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, o-vinylbenzyl methyl ether, m-vinylbenzyl methyl ether, p-vinylbenzyl methyl ether, o-vinylbenzylglycidyl ether, m-vinylbenzylglycidyl ether, p-vinylbenzylglycidyl ether, and indene;Methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, i-propyl acrylate, i-propyl methacrylate, n-butyl acrylate, n-butyl methacrylate, i-butyl acrylate, i-butyl methacrylate, sec-butyl acrylate, sec-butyl methacrylate, t-butyl acrylate, t-butyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate, 2-hydroxybutyl acrylate, 2-hydroxybutyl methacrylate, 3-hydroxybutyl acrylate, 3-hydroxybutyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, allyl acrylate, allyl methacrylate, benzyl acrylate, benzyl methacrylate, cy Unsaturated carboxylic acid esters such as chlorohexyl acrylate, cyclohexyl methacrylate, phenyl acrylate, phenyl methacrylate, 2-methoxyethyl acrylate, 2-methoxyethyl methacrylate, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate, methoxydiethylene glycol acrylate, methoxydiethylene glycol methacrylate, methoxytriethylene glycol acrylate, methoxytriethylene glycol methacrylate, methoxypropylene glycol acrylate, methoxypropylene glycol methacrylate, methoxydipropylene glycol acrylate, methoxydipropylene glycol methacrylate, isobornyl acrylate, isobornyl methacrylate, dicyclopentadienyl acrylate, dicyclopentadienyl methacrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-hydroxy-3-phenoxypropyl methacrylate, glycerol monoacrylate, glycerol monomethacrylate;Unsaturated aminoalkyl carboxylates such as 2-aminoethyl acrylate, 2-aminoethyl methacrylate, 2-dimethylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate, 2-aminopropyl acrylate, 2-aminopropyl methacrylate, 2-dimethylaminopropyl acrylate, 2-dimethylaminopropyl methacrylate, 3-aminopropyl acrylate, 3-aminopropyl methacrylate, 3-dimethylaminopropyl acrylate, and 3-dimethylaminopropyl methacrylate; unsaturated glycidyl carboxylates such as glycidyl acrylate and glycidyl methacrylate; vinyl carboxylates such as vinyl acetate, vinyl propionate, vinyl butyrate, and vinyl benzoate; vinyl methyl ether, vinyl ethyl ether, and allyl methyl ether. Examples include unsaturated ethers such as glycidyl ether; vinyl cyanide compounds such as acrylonitrile, methacrylonitrile, α-chloroacrylonitrile, and vinylidene cyanide; unsaturated amides such as acrylamide, methacrylamide, α-chloroacrylamide, N-2-hydroxyethylacrylamide, and N-2-hydroxyethylmethacrylamide; unsaturated imides such as maleimide, N-phenylmaleimide, and N-cyclohexylmaleimide; aliphatic conjugated dienes such as 1,3-butadiene, isoprene, and chloroprene; and macromonomers of polystyrene, polymethyl acrylate, polymethyl methacrylate, poly-n-butyl acrylate, poly-n-butyl methacrylate, and polysiloxane having monoacryloyl or monomethacryloyl groups at the ends of their polymer molecular chains. These monomers may be used individually or in combination of two or more.

[0057] The method for producing the copolymer is not particularly limited, and conventionally known polymerization methods may be used, with solution polymerization being preferred among known polymerization methods. The polymerization temperature and polymerization time vary depending on the type and ratio of monomers introduced, the molecular weight of the desired alkali-soluble resin, and the acid value, but for example, polymerization may be carried out at 60 to 130°C for 1 to 10 hours.

[0058] When a solvent is used during the polymerization, a solvent commonly used in radical polymerization reactions 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 individually or in combination of two or more.

[0059] The polymerization initiator used in the polymerization described above may be any commonly used polymerization initiator, and is not particularly limited. Specifically, examples include organic peroxides such as diisopropylbenzene hydroperoxide, di-t-butyl peroxide, benzoyl peroxide, t-butylperoxyisopropyl carbonate, t-amylperoxy-2-ethylhexanoate, and t-butylperoxy-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 individually or in combination of two or more.

[0060] During the polymerization described above, a chain transfer agent may be used to control the molecular weight and molecular weight distribution of the copolymer. The chain transfer agent may be a mercapto compound such as n-dodecanethiol, mercaptoacetic acid, or methyl mercaptoacetate; or an α-methylstyrene dimer.

[0061] The acid value of the alkali-soluble resin (B) is preferably 30 to 200 mg KOH / g. If the acid value of the alkali-soluble resin (B) is less than 30 mg KOH / g, it is difficult to ensure a sufficient development speed for the colored photosensitive resin composition, and if it exceeds 200 mg KOH / g, the adhesion to the substrate is reduced, making it easy for short circuits to occur in the pattern.

[0062] Furthermore, alkali-soluble resins with a polystyrene-equivalent weight-average molecular weight (hereinafter simply referred to as "weight-average molecular weight") of 3,000 to 100,000, preferably 5,000 to 50,000, as measured by gel permeation chromatography (GPC; using tetrahydrofuran as the eluent), are preferred. A molecular weight within this range is preferable because it tends to improve the hardness of the coating film, increase the residual film rate, and improve resolution due to excellent solubility of unexposed areas in the developer solution.

[0063] The molecular weight distribution [weight-average molecular weight (Mw) / number-average molecular weight (Mn)] of the alkali-soluble resin (B) is preferably 1.5 to 6.0, and more preferably 1.8 to 4.0. A molecular weight distribution [weight-average molecular weight (Mw) / number-average molecular weight (Mn)] of 1.5 to 6.0 is preferred because it exhibits excellent developability.

[0064] The alkali-soluble resin (B) may be included in an amount of 1 to 30% by weight relative to 100% by weight of the total solid content in the colored photosensitive resin composition. It is preferable that the content be within the above range because it ensures sufficient solubility of the developer, facilitating pattern formation, and suppresses film reduction in the exposed pixel areas during development, resulting in good loss of non-pixel areas.

[0065] [Photopolymerization initiator (C)] In one embodiment of the present invention, the photopolymerization initiator (C) includes a compound represented by the following chemical formula 1 and a compound represented by the following chemical formula 2.

[0066] [ka]

[0067] In the above formula, R 1 is, -(CH2) n R 4 And, R 2 C1-C 20 It is an alkyl group, R 3 teeth,

[0068] [ka]

[0069] And, R 4 is hydrogen or a C3-C6 cycloalkyl group, n is an integer between 1 and 5.

[0070] C1-C used in this specification 20 The alkyl group refers to a linear or branched hydrocarbon consisting of 1 to 20 carbon atoms, and includes, but is not limited to, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, pentyl, hexyl, 2-ethylhexyl, heptyl, octyl, nonyl, and decyl.

[0071] As used herein, C3-C6 cycloalkyl groups refer to monocyclic or fused cyclic hydrocarbons consisting of 3 to 6 carbon atoms, and include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0072] The colored photosensitive resin composition according to one embodiment of the present invention uses a mixture of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 as photopolymerization initiators, allowing for easy sensitivity adjustment and improving pattern adhesion and residue characteristics at short wavelengths of 300 nm or less, particularly 248 nm.

[0073] The compound represented by chemical formula 1 has high absorbance and excellent sensitivity to short wavelengths of 300 nm or less, thus improving the adhesion of the pattern.

[0074] Specific examples of compounds represented by the aforementioned chemical formula 1 include ethanolone, 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-, 1-(o-acetyloxime) (trade name: Irgacure OXE-02, manufactured by BASF), 1-propanone, 3-cyclopentyl-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-, 1-(o-acetyloxime) (trade name: TR-PBG-304, manufactured by Changzhou Strong Electronic New Materials Co., Ltd.).

[0075] Furthermore, the compound represented by chemical formula 2 can improve the pattern residue characteristics by appropriately adjusting the sensitivity of the compound represented by chemical formula 1, and it is possible to form ultrafine patterns of 0.5 μm or less in a thin film with a thickness of approximately 0.5 μm.

[0076] The weight ratio of the compound represented by chemical formula 1 to the compound represented by chemical formula 2 is preferably 25:75 to 85:15 from the viewpoint of adjusting sensitivity when exposure using an ultrashort wavelength light source of 300 nm or less, and more preferably 25:75 to 50:50. The photopolymerization initiator (C) may further contain photopolymerization initiators commonly used in the art, to the extent that it does not impair the objectives of the present invention.

[0077] The aforementioned photopolymerization initiators include one or more compounds selected from the group consisting of acetophenone compounds, benzophenone compounds, triazine compounds, biimidazole compounds, oxime compounds, and thioxanthone compounds, from the viewpoint of polymerization characteristics, initiation efficiency, absorption wavelength, availability, and price.

[0078] Specific examples of the aforementioned acetophenone compounds include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethylketal, 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methylpropan-1-one, 1-hydroxycyclohexylphenyl 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.

[0079] Examples of the aforementioned benzophenone compounds include benzophenone, o-methyl benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone.

[0080] Specific examples of the aforementioned triazine compounds include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[ Examples include 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, and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine.

[0081] Specific examples of the biimidazole compounds mentioned above 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, or biimidazole compounds in which the phenyl group at the 4,4',5,5' position is substituted with a carboalkoxy group. 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 preferred.

[0082] Specific examples of the aforementioned oxime compounds include o-ethoxycarbonyl-α-oxyimino-1-phenylpropan-1-one, 1,2-octanedione, -1-(4-phenylthio)phenyl, -2-(o-benzoyl oxime) (trade name: Irgacure OXE-01, manufactured by BASF), methanone, [8-[(acetyloxy)imino][2-(2,2,3,3-tetrafluoropropoxy)phenyl]methyl]-11-(2-ethylhexyl)-11H-benzo[a]carbazole-5-yl]-, (2,4,6-trimethylphenyl) (trade name: Irgacure OXE-03, manufactured by BASF), etanone, 1-[9-ethyl-6-(1,3-dioxolane, 4-(2-methoxyphenoxy)-9H-carbazole-3-yl]-, 1-(o-acetyloxime) (trade name: ADEKA OPT-N-1919 (manufactured by ADEKA), methanone, (9-ethyl-6-nitro-9H-carbazole-3-yl)[4-(2-methoxy-1-methylethoxy-2-methylphenyl]-, o-acetyloxime (trade name: ADEKA Arcules NCI-831, manufactured by ADEKA), 1-propanone, 3-cyclopentyl-1-[2-(2-pyrimidinylthio)-9H-carbazole-3-yl]-, 1-(o-acetyloxime) (trade name: TR-PBG-314, manufactured by Changzhou Strong Electronic New Materials Co., Ltd.), ethanone, 2-cyclohexyl-1-[2-(2-pyrimidinyloxy)-9H-carbazole-3-yl]-, 1-(o- Examples include acetyloxime) (trade name: TR-PBG-326, manufactured by Changzhou Strong Electronic New Materials Co., Ltd.), ethanone, 2-cyclohexyl-1-[2-(2-pyrimidinylthio)-9H-carbazole-3-yl]-, 1-(o-acetyloxime) (trade name: TR-PBG-331, manufactured by Changzhou Strong Electronic New Materials Co., Ltd.), 1-octanone, 1-[4-[3-[1-[(acetyloxy)imino]ethyl]-6-[4-[(4,6-dimethyl-2-pyrimidinyl)thio]-2-methylbenzoyl]-9H-carbazole-9-yl]phenyl]-, and 1-(o-acetyloxime) (trade name: EXTA-9, manufactured by Union Chemical Co., Ltd.).

[0083] Examples of the thioxanthone compounds include 2-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0084] Furthermore, the photopolymerization initiator (C) may be used in combination with a photopolymerization initiator (c1) to improve the sensitivity of the colored photosensitive resin composition of the present invention. The colored photosensitive resin composition according to one embodiment of the present invention can have its sensitivity further enhanced and productivity improved by containing a photopolymerization initiator (c1).

[0085] The photopolymerization initiator (c1) may preferably be one or more compounds selected from the group consisting of amine compounds, carboxylic acid compounds, and organic sulfur compounds having a thiol group.

[0086] The amine compounds may include, specifically, 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-dimethylparatoluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), and 4,4'-bis(diethylamino)benzophenone, with aromatic amine compounds being particularly preferred.

[0087] The carboxylic acid compound is preferably an aromatic heteroacetic acid, and specifically includes 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, naphthoxyacetic acid, and the like.

[0088] Specific examples of organosulfur compounds having the aforementioned 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).

[0089] The photopolymerization initiator (C) may be present in an amount of 0.1 to 5% by weight relative to 100% by weight of the total solid content in the colored photosensitive resin composition of the present invention. Within this range, the crosslinking characteristics by exposure can be improved and high resolution can be effectively achieved.

[0090] Furthermore, if the photopolymerization initiator (c1) is used, the photopolymerization initiator (c1) may be included in an amount of 0.1 to 3% by weight relative to 100% by weight of the total solid content in the colored photosensitive resin composition of the present invention. Within this range, the sensitivity of the colored photosensitive resin composition can be further increased, and the productivity of the color filters formed using the composition can be improved.

[0091] [Photopolymerizable compound (D)] In one embodiment of the present invention, the photopolymerizable compound (D) is a compound that can be polymerized by the action of the above-described photopolymerization initiator (C), and examples include monofunctional photopolymerizable compounds, bifunctional photopolymerizable compounds, or polyfunctional photopolymerizable compounds with three or more functions.

[0092] Specific examples of the monofunctional photopolymerizable compounds include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate, and N-vinylpyrrolidone. Commercially available examples include Aronics M-101 (manufactured by Toagosei Chemical Industry Co., Ltd.), KAYARAD TC-110S (manufactured by Nippon Kayaku Co., Ltd.), or Viscoat 158 ​​(manufactured by Osaka Organic Chemical Industry Co., Ltd.).

[0093] Specific examples of the aforementioned bifunctional photopolymerizable compounds include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloyloxyethyl) ether of bisphenol A, and 3-methylpentanediol di(meth)acrylate. Commercially available products include Aronics M-210, M-1100, M-1200 (manufactured by Toagosei Chemical Industry Co., Ltd.), KAYARAD HDDA (manufactured by Nippon Kayaku Co., Ltd.), Viscoat 260 (manufactured by Osaka Organic Chemical Industry Co., Ltd.), AH-600, AT-600, or UA-306H (manufactured by Kyoeisha Chemical Co., Ltd.).

[0094] Specific examples of the aforementioned polyfunctional photopolymerizable compounds with three or more functions include trimethylolpropane tri(meth)acrylate, ethoxylated trimethylolpropane tri(meth)acrylate, propoxylated trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, ethoxylated pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, ethoxylated dipentaerythritol hexa(meth)acrylate, and propoxylated dipentaerythritol hexa(meth)acrylate. Commercially available products include NK ESTER ATM-4E (manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) and NK ESTER. Examples include A-DPH-12E (manufactured by Shin-Nakamura Chemical Industry Co., Ltd.), Aronics M-309, M-520 (manufactured by Toagosei Chemical Industry Co., Ltd.), KAYARAD TMPTA, KAYARAD DPHA, or KAYARAD DPHA-40H (manufactured by Nippon Kayaku Co., Ltd.).

[0095] The photopolymerizable compounds exemplified above may be used individually or as a mixture of two or more.

[0096] The photopolymerizable compound may be present in the colored photosensitive resin composition of the present invention in an amount of 0.5 to 45% by weight, preferably 1 to 30% by weight, based on 100% by weight of the total solid content. When the photopolymerizable compound is present in the above range, it is preferable because there is no reduction in light sensitivity, the film strength is sufficient, the pattern does not disappear during development, the pattern is well constructed even in fine pattern areas, and the smoothness of the resist tends to be good.

[0097] [Solvent (E)] In one embodiment of the present invention, the solvent may be any solvent commonly used in colored photosensitive resin compositions, as long as it is effective in dissolving other components contained in the colored photosensitive resin composition of the present invention. In particular, ethers, aromatic hydrocarbons, ketones, alcohols, esters, or amides are preferred.

[0098] The aforementioned solvents specifically 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; and propylene glycol monomethyl ether acetate and propylene glycol monoethyl ether. Examples include alkylene glycol alkyl ether acetates such as 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 γ-butyrolactone.

[0099] Among the aforementioned solvents, it is more preferable to use an organic solvent with a boiling point of 100°C to 200°C from the viewpoint of application and drying properties. Examples of such solvents include propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, ethyl lactate, butyl lactate, ethyl 3-ethoxypropionate, and methyl 3-methoxypropionate.

[0100] The aforementioned solvents may be used individually or in combination of two or more.

[0101] The solvent may be present in an amount of 30 to 95% by weight, preferably 40 to 85% by weight, relative to 100% by weight of the colored photosensitive resin composition of the present invention. When the solvent is in the range of 30 to 95% by weight, it has the effect of improving coatability when applied by coating equipment such as a roll coater, spin coater, slit and spin coater, slit coater (sometimes also called a die coater), or inkjet.

[0102] [Additives (F)] The colored photosensitive resin composition of the present invention may optionally contain other additives such as polymer compounds, curing agents, surfactants, adhesion promoters, antioxidants, UV absorbers, and anti-aggregation agents.

[0103] Specific examples of the aforementioned other polymer compounds include thermosetting resins such as epoxy resins and maleimide resins, and thermoplastic resins such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ethers, polyfluoroalkyl acrylates, polyesters, and polyurethanes.

[0104] The curing agent is used to enhance deep curing and mechanical strength. Specific examples of curing agents include epoxy compounds, polyfunctional isocyanate compounds, melamine compounds, and oxetane compounds.

[0105] Specific examples of epoxy compounds in the curing agent include bisphenol A epoxy resins, hydrogenated bisphenol A epoxy resins, bisphenol F epoxy resins, hydrogenated bisphenol F epoxy resins, novolac-type epoxy resins, other aromatic epoxy resins, alicyclic epoxy resins, glycidyl ester resins, glycidylamine resins, or brominated derivatives of such epoxy resins, aliphatic, alicyclic or aromatic epoxy compounds other than epoxy resins and their brominated derivatives, butadiene (co)polymer epoxidized products, isoprene (co)polymer epoxidized products, glycidyl (meth)acrylate (co)polymers, triglycidyl isocyanurates, and the like.

[0106] Specific examples of oxetane compounds in the curing agent include carbonate bisoxetane, xylene bisoxetane, adipate bisoxetane, terephthalate bisoxetane, and cyclohexanedicarboxylic acid bisoxetane.

[0107] The curing agents exemplified above may be used individually or in combination of two or more types.

[0108] The curing agent may be used in combination with a curing auxiliary compound that can perform ring-opening polymerization of the epoxy group of the epoxy compound and the oxetane skeleton of the oxetane compound. Examples of the curing auxiliary compound include polycarboxylic acids, polycarboxylic acid anhydrides, and acid generators. The polycarboxylic acid anhydrides may be those commercially available as epoxy resin curing agents. Specific examples of epoxy resin curing agents include Adeka Hardener EH-700 (manufactured by Adeka Industries Co., Ltd.), Ricacid HH (manufactured by Shin-Nippon Rika Co., Ltd.), and MH-700 (manufactured by Shin-Nippon Rika Co., Ltd.).

[0109] The surfactant may be used to further improve the film-forming properties of the colored photosensitive resin composition, and fluorine-based surfactants, silicone-based surfactants, and the like may be preferably used.

[0110] Examples of the silicone-based surfactants include commercially available DC3PA, DC7PA, SH11PA, SH21PA, and SH8400 from Dow Corning Toray Silicone Co., Ltd., and TSF-4440, TSF-4300, TSF-4445, TSF-4446, TSF-4460, and TSF-4452 from GE Toshiba Silicone Co., Ltd. Examples of the fluorine-based surfactants include commercially available Megafac F-470, F-471, F-475, F-482, and F-489 from Dainippon Ink and Chemicals, Inc. The surfactants exemplified above may be used individually or in combination of two or more.

[0111] Specific examples of the adhesion promoters include 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-methacrylateoxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanatetopropyltrimethoxysilane, and 3-isocyanatetopropyltriethoxysilane. The adhesion promoters exemplified above may be used individually or in combination of two or more.

[0112] Specific examples of the aforementioned antioxidants include 2,2'-thiobis(4-methyl-6-t-butylphenol) and 2,6-di-t-butyl-4-methylphenol.

[0113] Specific examples of the aforementioned ultraviolet absorbers include 2-(3-t-butyl-2-hydroxy-5-methylphenyl)-5-chlorobenzotriazole and alkoxybenzophenone.

[0114] Specific examples of the aforementioned anti-coagulant include sodium polyacrylate.

[0115] A colored photosensitive resin composition according to one embodiment of the present invention can be manufactured, for example, by the following method.

[0116] First, the pigment from the coloring agent (A) is mixed with the solvent (E) and dispersed using a bead mill or the like until the average particle size of the pigment is about 0.2 μm or less. At this time, if necessary, a pigment dispersant, part or all of the alkali-soluble resin (B), or a dye may be mixed with the solvent (E) to dissolve or disperse. The remaining alkali-soluble resin (B), a photopolymerizable compound (D), a photopolymerization initiator (C), and an additive (F), and optionally the solvent (E) are further added to the mixed dispersion to a predetermined concentration to produce the colored photosensitive resin composition according to the present invention.

[0117] The colored photosensitive resin composition according to the present invention may be used when forming a colored pattern. Furthermore, as will be described later, the colored pattern may be used, for example, in a color filter, specifically in a color filter included in an image display device or a solid-state image sensor.

[0118] Accordingly, one embodiment of the present invention relates to a colored pattern and a color filter formed using the above-described colored photosensitive resin composition. The color filter according to one embodiment of the present invention may be manufactured by applying the above-described colored photosensitive resin composition onto a substrate and exposing and developing it in a predetermined pattern to form a colored pattern.

[0119] For example, the above-mentioned colored photosensitive resin composition may be applied to a substrate and dried to form a preliminary colored film.

[0120] When the color filter is applied to an image display device, the substrate is an uncoated glass substrate or SiN x A glass substrate may have a protective film coated to a thickness of 500 to 1,500 Å.

[0121] When the color filter is applied to a solid-state image sensor, the substrate may include a photoelectric conversion element substrate used in the solid-state image sensor (e.g., a silicon substrate for CCDs or CMOS sensors). The substrate may also include a black matrix or black stripe for isolating each pixel.

[0122] The coating process may include, for example, a coating or printing process such as roll coating, spin coating, slit coating, or inkjet printing.

[0123] Next, the preliminary colored film may be exposed and developed to form a colored pattern corresponding to each pixel.

[0124] The exposure process may include laser exposure using a mask that selectively exposes the pixel region. The light source may be a g-line (wavelength: 436 nm), h-line, KrF (248 nm), i-line (wavelength: 365 nm), etc. In particular, a KrF scanner may be used to realize ultra-fine patterns. The KrF scanner is an exposure device that uses a krypton fluoride source and emits a laser with a wavelength band of 248 nm.

[0125] Next, the unexposed areas may be selectively removed with a developer to form the colored pattern.

[0126] The developer may, for example, contain an inorganic or organic alkaline compound. Examples of the inorganic alkaline compound include sodium hydroxide, potassium hydroxide, disodium hydrogen phosphate, sodium dihydrogen phosphate, diammonium hydrogen phosphate, ammonium dihydrogen phosphate, potassium dihydrogen phosphate, sodium silicate, potassium silicate, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium borate, potassium borate, and ammonia. Examples of the organic alkaline compound include tetramethylammonium hydroxide, 2-hydroxyethyltrimethylammonium hydroxide, monomethylamine, dimethylamine, trimethylamine, monoethylamine, diethylamine, triethylamine, monoisopropylamine, diisopropylamine, and ethanolamine. These may be used individually or in combination of two or more.

[0127] After the development process, a post-baking process may be performed at, for example, 150-230°C.

[0128] One embodiment of the present invention relates to an image display device equipped with the above-described color filter.

[0129] The color filter of the present invention is applicable not only to conventional liquid crystal displays (LCDs) but also to various image display devices such as electroluminescent displays (ELs), plasma displays (PDPs), field emission displays (FEDs), and organic light-emitting devices (OLEDs).

[0130] The image display device of the present invention includes a configuration known in the art, except that it is equipped with the color filter described above.

[0131] An image display device according to one embodiment of the present invention may further include a color filter containing a red pattern layer containing red quantum dot particles, a green pattern layer containing green quantum dot particles, and a blue pattern layer containing blue quantum dot particles, in addition to the color filter described above. In such a case, the emitted light of the light source applied to the image display device is not particularly limited, but from the standpoint of better color reproduction, a light source emitting blue light may be preferably used.

[0132] An image display device according to one embodiment of the present invention may further include a color filter that, in addition to the color filter described above, includes pattern layers of only two hues from among a red pattern layer, a green pattern layer, and a blue pattern layer. In such a case, the color filter further includes a transparent pattern layer that does not contain quantum dot particles. When only two hue pattern layers are included, a light source that emits light of wavelengths representing the remaining hues that are not included may be used. For example, when only a red pattern layer and a green pattern layer are included, a light source that emits blue light may be used. In such a case, the red quantum dot particles emit red light, the green quantum dot particles emit green light, and the transparent pattern layer allows blue light to pass through, resulting in a blue color.

[0133] One embodiment of the present invention relates to a solid-state image sensor equipped with the color filter described above.

[0134] The solid-state image sensor may include, for example, a CMOS Image Sensor (CIS).

[0135] The solid-state image sensor includes a support containing a semiconductor element or a photoelectric conversion element and a microlens, and the color filter may be disposed between the support and the microlens. [Examples]

[0136] The present invention will be described in more detail below with reference to examples, comparative examples, and experimental examples. It should be noted that these examples, comparative examples, and experimental examples are merely for illustrative purposes, and it will be obvious to those skilled in the art that the scope of the present invention is not limited thereto.

[0137] [Examples 1-5 and Comparative Examples 1-7: Production of Colored Photosensitive Resin Compositions] A colored photosensitive resin composition was prepared by mixing the components according to the composition shown in Table 1 below (unit: weight %).

[0138] Experimental Example 1: Colored patterns were formed using the colored photosensitive resin compositions produced in Examples 1-5 and Comparative Examples 1-5, and the adhesion and residue of the colored patterns were measured by the following methods. The measurement results are shown in Tables 1 and 2 below.

[0139] The colored photosensitive resin compositions of the above examples and comparative examples were applied to the surface of an 8-inch silicon wafer by spin coating, and then placed on a heating plate and maintained at a temperature of 100°C for 90 seconds to form a preliminary colored layer. After the wafers with the preliminary colored layer formed were cooled to 23°C, they were exposed using a KrF scanner. The exposed coating was developed with a 0.2 wt% tetramethylammonium hydroxide (TMAH) aqueous solution and heated at 200°C for 180 seconds to form a colored pattern. The thickness of the colored pattern was 0.5 μm in all cases, and the minimum line width (resolution) was 0.5 μm.

[0140] The adhesion and residue of the formed colored patterns were evaluated according to the following criteria, and the results are shown in Tables 1 and 2 below.

[0141] (1) Evaluation of adhesion We observed whether the formed pattern remained 100% intact without any loss using CD-SEM and evaluated it according to the following evaluation criteria.

[0142] <Evaluation Criteria for Adhesion> 5: The formed pattern remains 100% intact without any loss. 4: The formed pattern remains at a rate of 90% or more but less than 100%. 3: The formed pattern remains at a rate of 70% or more but less than 90%. 2: The formed pattern remains at a rate of 50% or more but less than 70%. 1: Less than 50% of the formed pattern remains. (2) Evaluation of residues The resulting colored pattern residues were observed using CD-SEM and evaluated according to the following evaluation criteria.

[0143] <Criteria for evaluating residue> 5: No residue observed between colored patterns. 4: Residue distribution is present in the area between colored patterns, with a ratio of more than 0% to less than 10% of the total area. 3: Residue distribution is present in areas between the colored patterns, representing 10% to less than 20% of the total area. 2: Residue distribution is present in an area between 20% and 30% of the total area relative to the colored pattern. 1: Residue distribution is present in areas of 30% or more of the total area between colored patterns. Experimental Example 2: Except for using an i-line scanner instead of a KrF scanner for exposure, the same method as in Experimental Example 1 was used to form colored patterns using the colored photosensitive resin compositions produced in Comparative Examples 6 and 7, and the adhesion of the colored patterns and the residue were measured.

[0144] The measurement results are shown in Table 2 below.

[0145] [Table 1]

[0146] [Table 2]

[0147] As shown in Table 1 above, the colored photosensitive resin compositions of Examples 1 to 5, which contain carbazole compounds and acetophenone compounds of specific structures as photopolymerization initiators, were confirmed to exhibit excellent pattern adhesion and residue characteristics when exposed using an ultrashort wavelength light source of 300 nm or less.

[0148] In contrast, the colored photosensitive resin compositions of Comparative Examples 1 to 5, which used photopolymerization initiators that did not contain any of the compounds with the specific structures described above, were found to have poor adhesion or residue characteristics when exposed using a light source with an ultrashort wavelength of 300 nm or less.

[0149] Furthermore, it was confirmed that the colored photosensitive resin compositions of Comparative Examples 6 and 7, which contained carbazole and acetophenone compounds of specific structures as photopolymerization initiators, exhibited poor adhesion when exposed using a light source exceeding 300 nm.

[0150] Although specific parts of the present invention have been described in detail above, it is clear to any person with ordinary skill in the art to which the present invention belongs that such specific descriptions are merely preferred examples and do not limit the scope of the present invention. A person with ordinary skill in the art to which the present invention belongs will be able to make various applications and modifications within the scope of the present invention based on the above content.

[0151] Therefore, the substantial scope of the present invention can be defined by the claims and their equivalents.

Claims

1. A colored photosensitive resin composition comprising a colorant, an alkali-soluble resin, a photopolymerization initiator, a photopolymerizable compound, and a solvent, The aforementioned photopolymerization initiator is a colored photosensitive resin composition for forming a colored pattern using an ultrashort wavelength light source of 300 nm or less, comprising a compound represented by the following chemical formula 1 and a compound represented by the following chemical formula 2. 【Chemistry 1】 In the above formula, R １ is, -(CH ２ ) ｎ R ４ And, R ２ C １ -C ２０ It is an alkyl group, R ３ teeth, 【Chemistry 2】 And, R ４ is hydrogen or a C ３ -C ６ cycloalkyl group, and n is an integer between 1 and 5.

2. The colored photosensitive resin composition according to claim 1, wherein the weight ratio of the compound represented by chemical formula 1 and the compound represented by chemical formula 2 is 25:75 to 85:

15.

3. The colored photosensitive resin composition according to claim 1, wherein the colored photosensitive resin composition is for manufacturing a color filter for a solid-state image sensor.

4. The colored photosensitive resin composition according to claim 1, wherein the ultrashort wavelength light source of 300 nm or less is a light source irradiated by a KrF scanner exposure unit.

5. A colored pattern formed using the colored photosensitive resin composition according to any one of claims 1 to 4.

6. A color filter comprising the coloring pattern described in claim 5.

7. An image display device characterized by being equipped with the color filter described in claim 6.

8. A solid-state image sensor characterized by being equipped with the color filter described in claim 6.

9. A solid-state image sensor according to claim 8, comprising a CMOS Image Sensor (CIS).

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