Colored photosensitive resin composition, color filter, image display device, and solid-state imaging element

Abstract

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, a color filter formed using the same, and an image display device and a solid-state imaging element provided with the color filter, the alkali-soluble resin contains a copolymer of a vinyl ether compound and a carboxylic acid ammonium salt compound, and the photopolymerization initiator contains a compound having a specific structure. The colored photosensitive resin composition of the present invention can ensure reliability even when cured at a low temperature, and has high storage stability.

Description

Technical Field

[0001] The present invention relates to a colored photosensitive resin composition, a color filter, an image display device, and a solid-state imaging element. More specifically, it relates to a colored photosensitive resin composition that has excellent solvent resistance and resolution even when cured at low temperatures, thereby ensuring reliability and having high storage stability; a color filter formed using the same; and an image display device and a solid-state imaging element including the color filter. Background Art

[0002] Color filters are widely used in solid-state imaging devices, liquid crystal displays (LCDs), and other applications, and their scope of application is rapidly expanding. In particular, in solid-state imaging devices, these filters, as elements manufactured using integrated circuit technology, play the role of converting optical images into electrical signals. In recent years, as color filters used in solid-state imaging devices such as CCDs and CMOS have advanced toward higher pixel counts, the pixels in these devices have also become smaller, requiring even thinner film thicknesses.

[0003] Color filters are typically manufactured by uniformly coating a colored photosensitive resin composition containing pigments corresponding to red, green, and blue colors on a substrate with a black matrix pattern. The resulting coating is then heat-dried, exposed to light, developed, and further heat-cured as needed. This process is repeated for each color to form pixels of each color.

[0004] To improve productivity, research is underway to produce highly reliable color filters using a low-temperature firing process rather than a high-temperature firing process during pattern formation. For example, Japanese Patent No. 2,937,208 discloses a photosensitive resin composition that includes a thermal crosslinking agent such as a melamine resin or epoxy resin, enabling processing using a low-temperature firing process. Furthermore, Korean Patent No. 10-1464312 discloses a photosensitive resin composition that includes an epoxy resin as a binder resin and an epoxy curing agent such as an amine or anhydride-based epoxy curing agent, enabling complete curing even at low temperatures.

[0005] However, these photosensitive resin compositions have a problem of poor storage stability because they contain epoxy resins.

[0006] Therefore, there is a need for development of a colored photosensitive resin composition that can ensure reliability even when cured at a low temperature of 100° C. or lower and that has high storage stability. Summary of the Invention

[0007] Issues to be addressed

[0008] An object of the present invention is to provide a colored photosensitive resin composition that can ensure reliability even when cured at low temperatures and has high storage stability.

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

[0010] Still another object of the present invention is to provide an image display device and a solid-state imaging element including the above-mentioned color filter.

[0011] Solutions to Problems

[0012] In one aspect, 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.

[0013] The alkali-soluble resin includes a copolymer having a repeating unit represented by the following Chemical Formula 1 and a repeating unit represented by the following Chemical Formula 2,

[0014] The photopolymerization initiator includes a compound represented by the following Chemical Formula 3.

[0015] [Chemical Formula 1]

[0016]

[0017] [Chemical Formula 2]

[0018]

[0019] [Chemical Formula 3]

[0020]

[0021] In the above formula,

[0022] R a is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms,

[0023] R b is an alkyl group having 1 to 19 carbon atoms,

[0024] R c is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms,

[0025] R d is an alkyl group having 1 to 3 carbon atoms,

[0026] n and m are each independently an integer of 1 to 3,

[0027] A is -CH- or a nitrogen atom,

[0028] R 1 ~ R 8are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a group represented by Chemical Formula 4, -COR 16 or -NO2,

[0029] [Chemical Formula 4]

[0030]

[0031] R 13 is an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, a cycloalkenyl group having 4 to 8 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a phenyl group or a naphthyl group,

[0032] R 14 is a hydrogen atom, a cycloalkyl group having 3 to 8 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms,

[0033] R 15 is an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or an alkyl group having 1 to 10 carbon atoms,

[0034] R 16 is an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with one or more substituents selected from the group consisting of an alkoxy group having 1 to 20 carbon atoms and an alkyl group having 1 to 20 carbon atoms,

[0035] X does not exist or is -CO-,

[0036] * indicates a bond.

[0037] In one embodiment of the present invention, the content of the repeating unit represented by the above Chemical Formula 1 may be 10 to 40 mol % relative to 100 mol % of all repeating units constituting the alkali-soluble resin.

[0038] In one embodiment of the present invention, the content of the repeating unit represented by the above Chemical Formula 2 may be 10 to 40 mol % relative to 100 mol % of all repeating units constituting the alkali-soluble resin.

[0039] In one embodiment of the present invention, the above R 1 and R 2 、R 2 and R 3 、R 3 and R 4 、R 5 and R 6 、R 6 and R 7, or R 7 and R 8 At least one pair of them may be a group represented by the following Chemical Formula 5.

[0040] [Chemical Formula 5]

[0041]

[0042] In the above formula,

[0043] The above R 9 ~ R 12 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted phenyl group.

[0044] On the other hand, this invention provides the colored pattern formed using the said colored photosensitive resin composition.

[0045] In yet another aspect, the present invention provides a color filter comprising the above-mentioned colored pattern.

[0046] In yet another aspect, the present invention provides an image display device comprising the above-mentioned color filter.

[0047] In still another aspect, the present invention provides a solid-state imaging device characterized by including the above-mentioned color filter.

[0048] Effects of the Invention

[0049] The colored photosensitive resin composition of the present invention comprises a copolymer having repeating units derived from vinyl ether and repeating units having a carboxylic acid ammonium salt structure as an alkali-soluble resin, and a carbazole oxime-based or fluorene oxime-based photopolymerization initiator having a specific structure as a photopolymerization initiator. Thus, the composition exhibits excellent solvent resistance and resolution even when cured at low temperatures of 100°C or less, ensuring reliability, and also exhibits high storage stability. DETAILED DESCRIPTION

[0050] Hereinafter, the present invention will be described in more detail.

[0051] 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), wherein the alkali-soluble resin (B) comprises a copolymer having repeating units derived from a vinyl ether and repeating units having a carboxylic acid ammonium salt structure, and the photopolymerization initiator (D) comprises a carbazole oxime-based or fluorene oxime-based photopolymerization initiator having a specific structure.

[0052] Colorant (A)

[0053] In one embodiment of the present invention, the colorant (A) contains a pigment (a1) and / or a dye (a2).

[0054] Pigment (a1)

[0055] The pigments may be organic pigments or inorganic pigments commonly used in the art.

[0056] As the organic pigments, various pigments used in printing inks, inkjet inks, etc. can be used. Specifically, water-soluble azo pigments, insoluble azo pigments, phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, isoindolinone pigments, perylene pigments, pyrene pigments, dioxazine pigments, anthraquinone pigments, dianthraquinone-based pigments, anthrapyrimidine pigments, anthranthrone pigments, indanthrone pigments, flavanthrone pigments, pyranthrone pigments, diketopyrrolopyrrole pigments, etc. can be mentioned.

[0057] Examples of the inorganic pigments include metal compounds such as metal oxides and metal complexes, specifically oxides and composite metal oxides of metals such as iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, and antimony; and carbon black.

[0058] In particular, examples of the organic pigments and inorganic pigments include 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, but are not necessarily limited thereto.

[0059] 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;

[0060] CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, and 71;

[0061] 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;

[0062] CI Pigment Violet 14, 19, 23, 29, 32, 33, 36, 37, and 38;

[0063] CI Pigment Blue 15 (15:3, 15:4, 15:6, etc.), 21, 28, 60, 64, and 76;

[0064] CI Pigment Green 7, 10, 15, 25, 36, 47 and 58

[0065] CI Pigment Brown 28;

[0066] CI Pigment Black 1 and 7, etc.

[0067] Among the CI pigments exemplified above, 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 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.

[0068] The above-mentioned pigments can be used alone or in combination of two or more.

[0069] The pigment is preferably a pigment dispersion in which the particle size of the pigment is uniformly dispersed. As an example of a method for uniformly dispersing the particle size of the pigment, a method of adding a pigment dispersant (a3) for dispersion treatment can be cited. According to this method, a pigment dispersion in which the pigment is uniformly dispersed in a solution can be obtained.

[0070] Pigment dispersant (a3)

[0071] The pigment dispersant (a3) is added to deagglomerate the pigment and maintain its stability. Specific examples of the pigment dispersant include cationic, anionic, nonionic, amphoteric, polyester, polyamine and other surfactants, each of which can be used alone or in combination of two or more.

[0072] In addition, an acrylate dispersant containing butyl methacrylate (BMA) or N,N-dimethylaminoethyl methacrylate (DMAEMA) (hereinafter referred to as an acrylate dispersant) is preferably included. Commercially available products of the acrylate dispersant include DISPER BYK-2000, DISPER BYK-2001, DISPER BYK-2070, and DISPER BYK-2150. These acrylate dispersants can be used alone or in combination of two or more.

[0073] The pigment dispersant (a3) may also use other resin-type pigment dispersants other than the above-mentioned acrylate-based dispersants. Examples of the other resin-type pigment dispersants include known resin-type pigment dispersants, particularly polyurethanes, polycarboxylates represented by polyacrylates, unsaturated polyamides, polycarboxylates, (partial) amine salts of polycarboxylates, ammonium salts of polycarboxylates, alkylamine salts of polycarboxylates, polysiloxanes, long-chain polyaminoamide phosphates, esters of hydroxyl-containing polycarboxylates, and modified products thereof, or oily dispersants such as amides formed by the reaction of polyesters having free carboxyl groups with poly(lower alkylene imines) or salts thereof; water-soluble resins or water-soluble polymer compounds such as (meth)acrylic acid-styrene copolymers, (meth)acrylic acid-(meth)acrylate copolymers, styrene-maleic acid copolymers, polyvinyl alcohol, or polyvinyl pyrrolidone; polyesters; modified polyacrylates; addition products of ethylene oxide / propylene oxide; and phosphates.

[0074] Examples of commercially available products of the above-mentioned resin-type dispersants include cationic resin dispersants, such as BYK Chemicals' trade names: DISPER BYK-160, DISPER BYK-161, DISPER BYK-162, DISPER BYK-163, DISPER BYK-164, DISPER BYK-166, DISPER BYK-171, and DISPER BYK-172. BYK-182, DISPERBYK-184; BASF's 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; Lubirzol's trade names: SOLSPERS-24000, SOLSPERS-32550, NBZ-4204 / 10; Kawakami Fine Chemicals' trade names: HINOACT T-6000, HINOACT T-7000, HINOACT T-8000; Ajinomoto's trade name: AJISPUR PB-821, AJISPUR PB-822, AJISPUR PB-823; Kyoeisha Chemical Co., Ltd.’s trade names: FLORENE DOPA-17HF, FLORENE DOPA-15BHF, FLORENE DOPA-33, FLORENE DOPA-44, etc.

[0075] Other resin-type pigment dispersants other than the above-mentioned acrylic dispersants may be used alone or in combination of two or more, or may be used in combination with the acrylic dispersant.

[0076] The content of the pigment dispersant (a3) is 5 to 60 parts by weight, preferably 15 to 50 parts by weight, per 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. If the content is less than 5 parts by weight, problems such as difficulty in micronizing the pigment or gelation after dispersion may occur.

[0077] Dye (a2)

[0078] The dye (a2) can be used without limitation as long as it is soluble in an organic solvent. It is preferable to use a dye that is soluble in an organic solvent and has reliable solubility in an alkaline developer, heat resistance, solvent resistance, and the like.

[0079] As the above-mentioned dyes, acid dyes having acidic groups such as sulfonic acid or carboxylic acid, salts of acid dyes with nitrogen-containing compounds, sulfonamides of acid dyes, and their derivatives can be selected and used. In addition, azo-based, xanthene-based, phthalocyanine-based acid dyes and their derivatives can also be selected.

[0080] Preferred examples of the dye include compounds classified as dyes in the Color Index (published by Dyers Association) or known dyes described in the Dyeing Handbook (published by Seisensha).

[0081] Specific examples of the dyes include CI solvent dyes:

[0082] CI Solvent Yellow 4, 14, 15, 16, 21, 23, 24, 38, 56, 62, 63, 68, 79, 82, 93, 94, 98, 99, 151, 162, 163 and other yellow dyes;

[0083] CI Solvent Red 8, 45, 49, 89, 111, 122, 125, 130, 132, 146, 179 and other red dyes;

[0084] CI Solvent Orange 2, 7, 11, 15, 26, 41, 45, 56, 62 and other orange dyes;

[0085] CI Solvent Blue 5, 35, 36, 37, 44, 59, 67, 70 and other blue dyes;

[0086] CI Solvent Violet 8, 9, 13, 14, 36, 37, 47, 49 and other purple dyes;

[0087] CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35 and other green dyes, etc.

[0088] Among them, preferred are 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, which have excellent solubility in organic solvents among CI solvent dyes. Among them, more preferred are CI Solvent Yellow 21 and 79; CI Solvent Red 8, 122 and 132; and CI Solvent Orange 45 and 62.

[0089] In addition, CI acid dyes include:

[0090] 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, 1 Yellow dyes such as 60, 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;

[0091] 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, 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 and other red dyes;

[0092] CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173 and other orange dyes;

[0093] 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 and other blue dyes;

[0094] CI Acid Violet 6B, 7, 9, 17, 19, 66 and other purple dyes;

[0095] CI Acid Green 1, 3, 5, 9, 16, 25, 27, 50, 58, 63, 65, 80, 104, 105, 106, 109 and other green dyes, etc.

[0096] Among these, CI Acid Yellow 42, CI Acid Red 52 and 92, CI Acid Blue 80 and 90, CI Acid Violet 66, and CI Acid Green 27 are preferred because they have excellent solubility in organic solvents among acid dyes.

[0097] In addition, CI direct dyes include:

[0098] 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;

[0099] 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 and other red dyes;

[0100] CI Direct Orange 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107 and other orange dyes;

[0101] CI Direct Blue 38, 44, 57, 70, 77, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 166, 167, 170, 171 1. Blue dyes such as 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;

[0102] CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104 and other purple dyes;

[0103] CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82 and other green dyes, etc.

[0104] In addition, CI mordant dyes include:

[0105] CI Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65 and other yellow dyes;

[0106] CI Mordant 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;

[0107] 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 and other orange dyes;

[0108] 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 and other blue dyes;

[0109] CI Medium Violet 1, 2, 4, 5, 7, 14, 22, 24, 30, 31, 32, 37, 40, 41, 44, 45, 47, 48, 53, 58 and other purple dyes;

[0110] CI Mordant Green 1, 3, 4, 5, 10, 15, 19, 26, 29, 33, 34, 35, 41, 43, 53 and other green dyes, etc.

[0111] In the present invention, the dyes (a2) may be used alone or in combination of two or more.

[0112] The content of the colorant (A) can be 5 to 65% by weight, preferably 15 to 60% by weight, relative to 100% by weight of the total solid content in the colored photosensitive resin composition. When the content of the colorant (A) is within this range, the color density of pixels when formed into a thin film is sufficient, and the shedding properties of non-pixel areas during development are not reduced, resulting in no residue.

[0113] In the present invention, the solid content in the colored photosensitive resin composition means the total amount of components excluding the solvent.

[0114] Alkali soluble resin (B)

[0115] In one embodiment of the present invention, the alkali-soluble resin (B) has reactivity and alkali solubility due to the action of light or heat, and serves as a dispersion medium for solid components such as a colorant, and also functions as a binder resin.

[0116] The alkali-soluble resin includes a copolymer having a repeating unit derived from vinyl ether and a repeating unit having a carboxylic acid ammonium salt structure.

[0117] Specifically, the alkali-soluble resin (B) includes a copolymer having a repeating unit represented by the following Chemical Formula 1 and a repeating unit represented by the following Chemical Formula 2.

[0118] [Chemical Formula 1]

[0119]

[0120] [Chemical Formula 2]

[0121]

[0122] In the above formula,

[0123] R a is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms,

[0124] R b is an alkyl group having 1 to 19 carbon atoms,

[0125] R c is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms,

[0126] R d is an alkyl group having 1 to 3 carbon atoms,

[0127] n and m are each independently an integer of 1 to 3.

[0128] As used herein, an alkyl group having 1 to 3 carbon atoms refers to a linear or branched monovalent hydrocarbon group having 1 to 3 carbon atoms, and includes, but is not limited to, a methyl group, an ethyl group, an n-propyl group, and an isopropyl group.

[0129] As used herein, an alkyl group having 1 to 19 carbon atoms refers to a linear or branched hydrocarbon group having 1 to 19 carbon atoms, and includes, but is not limited to, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a 2-ethylhexyl group, a heptyl group, a 2-ethylheptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, a stearyl group, and a nonadecyl group.

[0130] In one embodiment of the present invention, from the perspective of being easily converted into carboxylic acid after baking, R d Preferably it is an alkyl group having 2 to 3 carbon atoms.

[0131] The alkali-soluble resin (B) includes a copolymer having a repeating unit represented by Chemical Formula 1 and a repeating unit represented by Chemical Formula 2, thereby exhibiting high reliability even when cured at a low temperature, and the colored photosensitive resin composition has excellent storage stability.

[0132] The repeating unit represented by Chemical Formula 1 is a precursor repeating unit in which a structure prior to the formation of a vinyl ether group is bonded to the terminal end of the diol backbone via a protective group. After prebaking, the terminal end is converted to a vinyl ether structure. After conversion to a vinyl ether structure, the repeating unit represented by Chemical Formula 1 crosslinks with vinyl or carboxyl groups present in other alkali-soluble resins during postbaking at temperatures below 100°C, enhancing low-temperature curability and reliability.

[0133] That is, the repeating unit represented by Chemical Formula 1 is protected by a protecting group before pre-baking, thus having no vinyl group. Therefore, it is unreactive during storage, ensuring excellent storage stability. Furthermore, after pre-baking, it is converted into a vinyl ether structure, thereby improving low-temperature curing properties during post-baking.

[0134] The content of the repeating unit represented by Chemical Formula 1 may be 10 to 40 mol%, preferably 15 to 30 mol%, relative to 100 mol% of all repeating units constituting the alkali-soluble resin. If the content of the repeating unit represented by Chemical Formula 1 is less than 10 mol%, low-temperature curing properties may be reduced, leading to decreased reliability. If the content exceeds 40 mol%, residues may be generated during the process or the storage stability of the composition may be deteriorated.

[0135] The repeating unit represented by Chemical Formula 2 is a repeating unit with an ammonium carboxylate structure formed by ring-opening a carboxylic anhydride and linking to the end of a diol backbone. After pre-baking, the ammonium carboxylate salt is converted to a carboxylic acid. After conversion to a carboxylic acid, the repeating unit represented by Chemical Formula 2 crosslinks with vinyl groups present in other alkali-soluble resins during a post-baking process at temperatures below 100°C, enhancing low-temperature curability and reliability.

[0136] That is, the repeating unit represented by Chemical Formula 2 forms a carboxylic acid ammonium salt structure before pre-baking and is therefore unreactive during storage, ensuring excellent storage stability. Furthermore, after pre-baking, it is converted into a carboxylic acid, thereby improving low-temperature curability during post-baking of the exposed portion while ensuring alkali solubility in the non-exposed portion.

[0137] The content of the repeating unit represented by Chemical Formula 2 may be 10 to 40 mol%, preferably 15 to 30 mol%, relative to 100 mol% of all repeating units constituting the alkali-soluble resin. If the content of the repeating unit represented by Chemical Formula 2 is less than 10 mol%, low-temperature curability may be reduced, resulting in decreased reliability. If the content exceeds 40 mol%, the storage stability of the composition may be deteriorated.

[0138] The alkali-soluble resin (B) may further have a repeating unit derived from an ethylenically unsaturated compound having a carboxyl group.

[0139] Specific examples of the ethylenically unsaturated compound having a carboxyl group include monocarboxylic acids such as acrylic acid, methacrylic acid, and crotonic acid; dicarboxylic acids such as fumaric acid, mesaconic acid, and itaconic acid; anhydrides of these dicarboxylic acids; and mono(meth)acrylates of polymers having carboxyl and hydroxyl groups at both ends, such as ω-carboxypolycaprolactone mono(meth)acrylate. Among these, acrylic acid and methacrylic acid are preferred.

[0140] Furthermore, the alkali-soluble resin (B) may further have a repeating unit derived from another compound having an unsaturated double bond in addition to the repeating unit.

[0141] Examples of the above-mentioned other compounds having an unsaturated double bond include:

[0142] Hydroxyalkyl (meth)acrylate compounds such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, and 2-hydroxy-3-phenoxypropyl (meth)acrylate;

[0143] 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, p-vinylbenzyl glycidyl ether and other aromatic vinyl compounds;

[0144] N-substituted maleimide compounds such as N-cyclohexylmaleimide, N-benzylmaleimide, N-phenylmaleimide, N-o-hydroxyphenylmaleimide, N-m-hydroxyphenylmaleimide, N-p-hydroxyphenylmaleimide, N-o-methylphenylmaleimide, N-m-methylphenylmaleimide, N-p-methylphenylmaleimide, N-o-methoxyphenylmaleimide, N-m-methoxyphenylmaleimide, and N-p-methoxyphenylmaleimide;

[0145] Alkyl (meth)acrylate compounds such as methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, sec-butyl (meth)acrylate, and tert-butyl (meth)acrylate;

[0146] Alicyclic (meth)acrylate compounds such as cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, 2-dicyclopentyloxyethyl (meth)acrylate, and isobornyl (meth)acrylate;

[0147] Aryl (meth)acrylates such as phenyl (meth)acrylate and benzyl (meth)acrylate;

[0148] 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;

[0149] vinyl acetate, vinyl propionate and other vinyl carboxylate compounds;

[0150] (Meth)acrylonitrile, vinyl cyanide compounds such as α-chloroacrylonitrile, etc. These can be used alone or in combination of two or more.

[0151] The method for producing the copolymer is not particularly limited, and conventionally known polymerization methods may be used. Among the conventional polymerization methods, solution polymerization is preferred. The polymerization temperature and polymerization time vary depending on the type and ratio of the monomers introduced, the desired molecular weight and acid value of the alkali-soluble resin, and, for example, polymerization may be performed at 60 to 130° C. for 1 to 10 hours.

[0152] If a solvent is used in the polymerization, a solvent commonly used in free 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 alone or in combination of two or more.

[0153] As the polymerization initiator used in the above-mentioned polymerization, a commonly used polymerization initiator can be added without particular limitation. Specifically, organic peroxides such as diisopropylbenzene hydroperoxide, di-tert-butyl peroxide, benzoyl peroxide, tert-butyl peroxyisopropyl carbonate, tert-amyl peroxy-2-ethylhexanoate, and tert-butyl peroxy-2-ethylhexanoate; and nitrogen compounds such as 2,2'-azobis(isobutyronitrile), 2,2'-azobis(2,4-dimethylvaleronitrile), and 2,2'-azobis(2-methylpropionic acid)dimethyl ester can be used alone or in combination of two or more.

[0154] During the polymerization, a chain transfer agent may be used to control the molecular weight or molecular weight distribution of the copolymer. Examples of the chain transfer agent include mercapto compounds such as n-dodecylmercaptan, thioglycolic acid, and methyl thioglycolate; and α-methylstyrene dimer.

[0155] The acid number of above-mentioned alkali soluble resin (B) can be 20~200 (mgKOH / g).If acid number is in above-mentioned scope, then the solubility in developer is improved and non-exposed portion is easily dissolved, and sensitivity improves, and the pattern of exposed portion is left when developing and film remaining rate (film remaining ratio) is improved, therefore preferably.Here, so-called acid number, refers to the value measured as the amount (mg) of potassium hydroxide required when neutralizing 1g polymer, can usually use potassium hydroxide aqueous solution to carry out titration and obtain.

[0156] The alkali-soluble resin (B) may have a polystyrene-equivalent weight average molecular weight (hereinafter referred to as "weight average molecular weight") as measured by gel permeation chromatography (GPC; using tetrahydrofuran as the elution solvent) of 3,000 to 200,000, preferably 5,000 to 100,000. A molecular weight within this range is preferred because it tends to improve the hardness of the coating film and increase the film retention rate, improve the solubility of the non-exposed portion in the developer, and improve the resolution.

[0157] 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, 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 provides excellent developability.

[0158] The content of the alkali-soluble resin (B) can be 5 to 60% by weight, preferably 5 to 45% by weight, relative to 100% by weight of the total solid content in the colored photosensitive resin composition. When the content of the alkali-soluble resin (B) is within this range, it is preferred because it has sufficient solubility in the developer, facilitates pattern formation, and prevents film reduction in the pixel portion of the exposed area during development, thereby improving the peeling resistance of the non-pixel portion.

[0159] Photopolymerizable compound (C)

[0160] 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 examples thereof include monofunctional photopolymerizable compounds, difunctional photopolymerizable compounds, and trifunctional or higher polyfunctional photopolymerizable compounds.

[0161] Specific examples of the monofunctional photopolymerizable compound include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinyl pyrrolidone, and the like. Commercially available products include ARONIX M-101 (Toagosei), KAYARAD TC-110S (Nippon Kayaku), and VISCOAT 158 (Osaka Organic Chemical Industry).

[0162] Specific examples of the above-mentioned 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, 3-methylpentanediol di(meth)acrylate, etc., and commercially available products include ARONIX M-210, M-1100, M-1200 (Toagosei), KAYARAD HDDA (Nippon Kayaku), VISCOAT 260 (Osaka Organic Chemical Industry), AH-600, AT-600 or UA-306H (Kyoeisha Chemical Co., Ltd.), etc.

[0163] Specific examples of the trifunctional or higher polyfunctional photopolymerizable compound 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 (Shin-Nakamura), ARONIX M-309 and M-520 (Toagosei), KAYARAD TMPTA, KAYARAD DPHA, and KAYARAD DPHA-40H (Nippon Kayaku).

[0164] The photopolymerizable compounds exemplified above can be used alone or in combination of two or more.

[0165] The content of the photopolymerizable compound (C) may be 0.5 to 50% by weight, particularly 5 to 30% by weight, relative to 100% by weight of the total solid content in the colored photosensitive resin composition. When the content of the photopolymerizable compound (C) is within this range, the strength and smoothness of the pixel portion can be improved.

[0166] Photopolymerization initiator (D)

[0167] In one embodiment of the present invention, the photopolymerization initiator (D) is a compound for initiating polymerization of the photopolymerizable compound (C), and includes one or more photopolymerization initiators of the carbazole oxime type and the fluorene oxime type.

[0168] Particularly, the photopolymerization initiator (D) includes a compound represented by the following Chemical Formula 3.

[0169] [Chemical Formula 3]

[0170]

[0171] In the above formula,

[0172] A is -CH- or a nitrogen atom,

[0173] R 1 ~ R 8 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a group represented by Chemical Formula 4, -COR 16 or -NO2,

[0174] [Chemical Formula 4]

[0175]

[0176] R 13 is an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, a cycloalkenyl group having 4 to 8 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a phenyl group or a naphthyl group,

[0177] R 14 is a hydrogen atom, a cycloalkyl group having 3 to 8 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms,

[0178] R 15 is an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or an alkyl group having 1 to 10 carbon atoms,

[0179] R 16 is an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with one or more substituents selected from the group consisting of an alkoxy group having 1 to 20 carbon atoms and an alkyl group having 1 to 20 carbon atoms,

[0180] X does not exist or is -CO-,

[0181] * indicates a bond.

[0182] In one embodiment of the present invention, the above R 1and R 2 、R 2 and R 3 、R 3 and R 4 、R 5 and R 6 、R 6 and R 7 , or R 7 and R 8 At least one pair of them may be a group represented by the following Chemical Formula 5.

[0183] [Chemical Formula 5]

[0184]

[0185] In the above formula,

[0186] The above R 9 ~ R 12 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted phenyl group.

[0187] As used herein, an alkyl group having 1 to 20 carbon atoms refers to a linear or branched hydrocarbon group having 1 to 20 carbon atoms, and includes, but is not limited to, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a 2-ethylhexyl group, a heptyl group, a 2-ethylheptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, a stearyl group, a nonadecyl group, and an eicosyl group.

[0188] As used herein, an alkenyl group having 2 to 12 carbon atoms refers to a linear or branched divalent unsaturated hydrocarbon group having 2 to 12 carbon atoms and having one or more carbon-carbon double bonds, and includes, but is not limited to, ethenyl, propenyl, butenyl, and pentenyl.

[0189] As used herein, a cycloalkenyl group having 4 to 8 carbon atoms refers to a monocyclic or condensed ring hydrocarbon group having 4 to 8 carbon atoms and having one or more carbon-carbon double bonds, and includes, but is not limited to, cyclobutenyl, cyclopentenyl, and cyclohexenyl.

[0190] As used herein, an alkynyl group having 2 to 12 carbon atoms refers to a linear or branched unsaturated hydrocarbon group having 2 to 12 carbon atoms and having one or more carbon-carbon triple bonds, including, but not limited to, ethynyl, propynyl, and butynyl.

[0191] As used herein, a cycloalkyl group having 3 to 10 carbon atoms refers to a monocyclic or condensed ring hydrocarbon group having 3 to 10 carbon atoms, and includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0192] As used herein, a cycloalkyl group having 3 to 8 carbon atoms refers to a monocyclic or condensed ring hydrocarbon group having 3 to 8 carbon atoms, and includes, but is not limited to, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.

[0193] As used herein, an alkenyl group having 2 to 5 carbon atoms refers to a linear or branched divalent unsaturated hydrocarbon group having 2 to 5 carbon atoms and having one or more carbon-carbon double bonds, and includes, but is not limited to, ethenyl, propenyl, butenyl, and pentenyl.

[0194] As used herein, an alkoxy group having 1 to 20 carbon atoms refers to a linear or branched alkoxy group having 1 to 20 carbon atoms, including, but not limited to, a methoxy group, an ethoxy group, and an n-propoxy group.

[0195] As used herein, the term "aryl group having 6 to 20 carbon atoms" includes all monovalent aromatic groups and their partially reduced derivatives. The aromatic group is a monocyclic or condensed ring having 6 to 20 carbon atoms. Representative examples of aryl groups include, but are not limited to, phenyl, naphthyl, tetrahydronaphthyl, pyrenyl, fluorenyl, diphenylfluorenyl, dinaphthylfluorenyl, carbazolyl, and biphenyl.

[0196] As used herein, heteroaryl groups having 3 to 20 carbon atoms include all monovalent heteroaromatic groups and partially reduced derivatives thereof. The heteroaromatic groups are monocyclic or condensed rings having 3 to 20 carbon atoms and containing one or more oxygen, sulfur, or nitrogen groups. Representative examples of heteroaryl groups include, but are not limited to, pyridinyl, furanyl, thiophenyl, indolyl, quinolinyl, imidazolinyl, oxazolyl, and thiazolyl.

[0197] As used herein, an alkyl group having 1 to 10 carbon atoms refers to a linear or branched hydrocarbon group having 1 to 10 carbon atoms, and includes, but is not limited to, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, a 2-ethylhexyl group, a heptyl group, a 2-ethylheptyl group, an octyl group, a nonyl group, and a decyl group.

[0198] When the compound represented by Chemical Formula 3 is used as the photopolymerization initiator (D), the degree of curing can be increased even at low temperature, thereby achieving high reliability.

[0199] Examples of commercially available products of the compound represented by the above Chemical Formula 3 include PBG-314 and PBG-345 (both manufactured by TRONLY).

[0200] In addition to the compound represented by Chemical Formula 3, the photopolymerization initiator (D) may further include other photopolymerization initiators commonly used in the art in an amount of 40 wt % or less based on the total weight of the photopolymerization initiator.

[0201] For example, as the above-mentioned other photopolymerization initiators, from the viewpoints of polymerization characteristics, initiation efficiency, absorption wavelength, availability, price, etc., it is preferred to use one or more compounds selected from the group consisting of acetophenone compounds, benzophenone compounds, triazine compounds, biimidazole compounds, oxime compounds and thioxanthone compounds.

[0202] Specific examples of the acetophenone compounds include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropane-1-one, benzyl dimethyl ketal, 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methylpropane-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1-(4-methylphenylthio)-2-morpholinopropane-1-one, 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)butane-1-one, 2-hydroxy-2-methyl-1-[4-(1-methylvinyl)phenyl]propane-1-one, and 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4-morpholinophenyl)butane-1-one.

[0203] Examples of the benzophenone-based compound include benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, 3,3′,4,4′-tetrakis(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone.

[0204] Specific examples of the biimidazole 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 alkoxycarbonyl groups. Among them, 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.

[0205] Specific examples of the 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-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, -[2-(5-methylfuran-2-yl)ethylidene]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethylidene]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethylidene]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethylidene]-1,3,5-triazine, etc.

[0206] Examples of the oxime compounds include 1-[4-(phenylthio)phenyl]-1,2-octanedione-2-(O-benzoyloxime), 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethanone-1-(O-acetyloxime), and commercially available products include TR-PBG-305 (TRONLY), OXE-01 (BASF), and OXE-02 (BASF).

[0207] Examples of the thioxanthone-based compounds include 2-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0208] Examples of the benzoin-based compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.

[0209] In addition to the compounds exemplified above, carbazole compounds, diketone compounds, sulfonium borate compounds, diazo compounds, biimidazole compounds, and the like can also be used as the photopolymerization initiator.

[0210] The photopolymerization initiator (D) can be used together with a photopolymerization initiation aid (d1) to improve the sensitivity of the colored photosensitive resin composition of the present invention. The colored photosensitive resin composition of the present invention can further increase sensitivity and improve productivity by containing a photopolymerization initiation aid (d1).

[0211] As the photopolymerization initiation aid (d1), 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 can be preferably used.

[0212] As the above-mentioned amine compounds, specifically, aliphatic amine compounds such as triethanolamine, methyldiethanolamine, and triisopropanolamine; aromatic amine compounds such as methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isopentyl 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 can be used, and aromatic amine compounds are particularly preferably used.

[0213] 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.

[0214] 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-mercaptobutoxyethyl)-1,3,5-triazine-2,4,6(1H,3H,5H)-trione, trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptobutyrate), pentaerythritol tetrakis(3-mercaptopropionate), dipentaerythritol hexa(3-mercaptopropionate), and tetraethylene glycol bis(3-mercaptopropionate).

[0215] Relative to the overall 100 weight percent of solid content in colored photosensitive resin composition, the content of above-mentioned photopolymerization initiator (D) can be 0.1 ~ 10 weight percent, preferably can be 1 ~ 8 weight percent.If the content of above-mentioned photopolymerization initiator (D) is in above-mentioned scope, then the colored photosensitive resin composition of the present invention is highly sensitive and exposure time is shortened, thus productivity is improved, and high resolution can be maintained, therefore preferably.In addition, the intensity of the pixel portion formed using the composition of above-mentioned conditions and the surface smoothness of above-mentioned pixel portion can become good.

[0216] When the photopolymerization initiator aid (d1) is further used, the amount of the photopolymerization initiator aid (d1) is generally 10 mol or less, preferably 0.01 to 5 mol, based on 1 mol of the photopolymerization initiator. When the content of the photopolymerization initiator aid (d1) is within 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 can be improved.

[0217] Solvent (E)

[0218] In one embodiment of the present invention, the solvent (E) may be any solvent commonly used in colored photosensitive resin compositions without particular limitation, as long as it is effective in dissolving other components contained in the colored photosensitive resin composition. Particularly preferred are ethers, aromatic hydrocarbons, ketones, alcohols, esters, and amides.

[0219] Specific examples of the solvent (E) include ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, dipropylene glycol dipropyl ether and dipropylene glycol dibutyl ether; aromatic hydrocarbons such as benzene, toluene, xylene and mesitylene; ketones such as methyl ethyl ketone, acetone, methyl amyl ketone, methyl isobutyl ketone and cyclohexanone; and alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol and glycerol. esters such as ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, methyl cellosolve acetate, ethyl cellosolve acetate, ethyl acetate, butyl acetate, amyl acetate, methyl lactate, ethyl lactate, butyl lactate, 3-methoxybutyl acetate, 3-methyl-3-methoxy-1-butyl acetate, methoxypentyl acetate, ethylene glycol monoacetate, ethylene glycol diacetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoacetate, diethylene glycol diacetate, diethylene glycol monobutyl ether acetate, propylene glycol monoacetate, propylene glycol diacetate, propylene glycol monoethyl ether acetate, ethylene carbonate, propylene carbonate, and γ-butyrolactone. Each of the above solvents can be used alone or in combination of two or more.

[0220] The content of the solvent (E) can be 30 to 95% by weight, preferably 40 to 85% by weight, relative to 100% by weight of the total colored photosensitive resin composition. When the content of the solvent (E) is within the above range, coating properties can be improved when coating is performed using a coating apparatus such as a roll coater, a spin coater, a slot spin coater, a slot coater (sometimes also referred to as a die coater), or an inkjet printer.

[0221] Additives (F)

[0222] In the colored photosensitive resin composition of one embodiment of the present invention, in addition to the above-mentioned components, additives (F) such as fillers, other polymer compounds, curing agents, adhesion promoters, ultraviolet absorbers, and anti-coagulation agents may be used in combination as needed by those skilled in the art within the scope of not impairing the purpose of the present invention.

[0223] Specifically, glass, silica, alumina, etc. can be used as the filler, but the filler is not limited thereto.

[0224] Specific examples of the other polymer compounds include curable 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.

[0225] The curing agent is used to achieve deep curing and improve mechanical strength, and specifically, epoxy compounds, multifunctional isocyanate compounds, melamine compounds, oxetane compounds, etc. can be used, but are not limited thereto. The epoxy compound can specifically use bisphenol A epoxy resin, hydrogenated bisphenol A epoxy resin, bisphenol F epoxy resin, hydrogenated bisphenol F epoxy resin, novolac epoxy resin, other aromatic epoxy resins, alicyclic epoxy resins, glycidyl ester resins, glycidyl amine resins, or brominated derivatives of these epoxy resins, aliphatic, alicyclic or aromatic epoxy compounds other than epoxy resins and brominated derivatives thereof, butadiene (co)polymer epoxides, isoprene (co)polymer epoxides, glycidyl (meth)acrylate (co)polymers, triglycidyl isocyanurate, etc., but are not limited thereto. Specific examples of the oxetane compound include carbonate bisoxetane, xylene bisoxetane, adipate bisoxetane, terephthalate bisoxetane, and cyclohexanedicarboxylic acid bisoxetane, but are not limited thereto.

[0226] The above-mentioned curing agent can be used in combination with a co-curing compound, which can, together with the curing agent, cause the epoxy group of the epoxy compound and the oxetane skeleton of the oxetane compound to undergo ring-opening polymerization. The above-mentioned co-curing compound can specifically use polycarboxylic acids, polycarboxylic acid anhydrides, acid generators, etc. The above-mentioned polycarboxylic acid anhydrides can utilize commercially available epoxy resin curing agents. As commercially available epoxy resin curing agents, for example, ADEKA HARDENER EH-700 (trade name, manufactured by ADEKA Industries (Strain)), RIKACID HH (trade name, manufactured by Shin Nippon Rika (Strain)), MH-700 (trade name, manufactured by Shin Nippon Rika (Strain)), etc.

[0227] The curing agents and auxiliary curing compounds exemplified above may be used alone or in combination of two or more.

[0228] The above-mentioned adhesion promoter can specifically use one or a mixture of two or more selected from the group consisting of vinyltrimethoxysilane, vinyltriethoxysilane, vinyltri(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-methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanatepropyltrimethoxysilane and 3-isocyanatepropyltriethoxysilane.

[0229] The content of the adhesion promoter may be 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.

[0230] Specific examples of the ultraviolet absorber include 2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chlorobenzotriazole and alkoxybenzophenone, but are not limited thereto.

[0231] Specifically, sodium polyacrylate and the like can be used as the anti-coagulant, but the invention is not limited thereto.

[0232] The colored photosensitive resin composition according to one embodiment of the present invention can be produced, for example, by the following method.

[0233] First, the pigment in the colorant is mixed with a solvent and dispersed using a bead mill or the like until the average particle size of the pigment is 0.2 μm or less. At this point, the pigment dispersant, part or all of the alkali-soluble resin, and the dye may be mixed with the solvent as needed to dissolve or disperse them. The remaining alkali-soluble resin, photopolymerization initiator, photopolymerizable compound, and additives are added to the mixed dispersion, and further solvent is added as needed to achieve a predetermined concentration. This allows the production of the colored photosensitive resin composition of the present invention.

[0234] The colored photosensitive resin composition of the present invention can be used to produce a colored pattern. As described below, the colored pattern can be used for, for example, a color filter, specifically, a color filter for an image display device or a solid-state imaging element.

[0235] Therefore, one embodiment of the present invention relates to a colored pattern and a color filter formed using the colored photosensitive resin composition. The color filter according to one embodiment of the present invention is characterized in that it includes a colored pattern formed by applying the colored photosensitive resin composition on a substrate, exposing it to light in a predetermined pattern, and developing it.

[0236] Hereinafter, the pattern forming method using the colored photosensitive resin composition of the present invention will be described in detail.

[0237] The method for forming a pattern using the colored photosensitive resin composition of the present invention can be a method known in the art, and generally 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 then photocured and developed to form a pattern, thereby enabling use as a colored pixel (colored image).

[0238] Specifically, the colored photosensitive resin composition is applied to a substrate using an appropriate method such as spin coating or slit coating. After coating, the substrate is irradiated with light to form the desired pattern for the color filter. After irradiation, if the coating layer is treated with an alkaline developer, the unirradiated portions of the coating layer will dissolve, forming the desired pattern for the color filter. This process is repeated according to the required number of R, G, and B colors to obtain a color filter with the desired pattern. Furthermore, the image pattern obtained by development in the above process can be cured by reheating or irradiation with active radiation, which can further improve crack resistance and solvent resistance.

[0239] When the color filter is applied to an image display device, the substrate may be a glass substrate not coated with any substance or a glass substrate coated with SiNx (protective film) with a thickness of 500 to 1,500 Å.

[0240] When the color filter is applied to a solid-state imaging device, the substrate may include a photoelectric conversion element substrate for the solid-state imaging device (for example, a silicon substrate for CCD or CMOS) and may include a black matrix or black stripes for isolating pixels.

[0241] One embodiment of the present invention relates to an image display device including the above-mentioned color filter.

[0242] The color filter of the present invention can be applied not only to conventional liquid crystal display devices (LCDs), but also to various image display devices such as electroluminescent display devices (ELs), plasma display devices (PDPs), field emission display devices (FEDs), and organic light emitting elements (OLEDs).

[0243] The image display device of the present invention includes a configuration known in the technical field in addition to the color filter described above.

[0244] In one embodiment of the present invention, an image display device may further include, in addition to the aforementioned color filter, a color filter comprising a red patterned layer containing red quantum dot particles, a green patterned layer containing green quantum dot particles, and a blue patterned layer containing blue quantum dot particles. In this case, the light source used in the image display device is not particularly limited in terms of light emission, but a light source emitting blue light is preferably used for better color reproducibility.

[0245] In one embodiment of the present invention, the image display device may further include, in addition to the color filter described above, a color filter comprising only two color pattern layers among a red pattern layer, a green pattern layer, and a blue pattern layer. In this case, the color filter further includes a transparent pattern layer that does not contain quantum dot particles. In the case of only two color pattern layers, a light source that emits light with wavelengths representing the remaining colors not included can be used. For example, in the case of only a red pattern layer and a green pattern layer, a light source that emits blue light can be used. In this case, the red quantum dot particles emit red light, the green quantum dot particles emit green light, and the transparent pattern layer allows the blue light to pass directly through, resulting in a blue appearance.

[0246] One embodiment of the present invention relates to a solid-state imaging element including the above-mentioned color filter.

[0247] The solid-state imaging element may include, for example, a CMOS image sensor.

[0248] The solid-state imaging element includes a support including a semiconductor element or a photoelectric conversion element and a microlens, and the color filter may be arranged between the support and the microlens.

[0249] The present invention will be described in more detail below by way of examples, comparative examples and experimental examples. It will be apparent to those skilled in the art that these examples, comparative examples and experimental examples are merely illustrative of the present invention and the scope of the present invention is not limited thereto.

[0250] Preparation Example 1: Preparation of Pigment Dispersion

[0251] 20 parts by weight of CI Pigment Green 36 as a pigment, 5 parts by weight of BYK LPN-6919 (BYK) as a pigment dispersant, and 75 parts by weight of propylene glycol monomethyl ether acetate as a solvent were mixed and dispersed using a bead mill to prepare a pigment dispersion.

[0252] Synthesis Example 1: Synthesis of Alkali-Soluble Resin B-1

[0253] In a reaction vessel equipped with a thermometer, a stirrer, a gas inlet pipe, a condenser, and a dropping tank inlet port, 146.8 parts by weight of propylene glycol monomethyl ether acetate was placed, and after nitrogen substitution, the mixture was heated to 60° C. Separately, as a dropping tank (A), a solution prepared by stirring and mixing 2.0 parts by weight (0.02 mol) of N-benzylmaleimide, 35.5 parts by weight (0.37 mol) of cyclohexyl methacrylate, 1.0 part by weight (0.02 mol) of methyl methacrylate, 30.0 parts by weight (0.4 mol) of 2-hydroxyethyl methacrylate, 30.0 parts by weight of propylene glycol monomethyl ether acetate, and 2.0 parts by weight of n-dodecylmercaptan was prepared in a beaker. As a dropping tank (B), a uniform mixed solution prepared by charging and stirring 28.5 parts by weight of propylene glycol monomethyl ether acetate, 10.1 parts by weight (0.2 mol) of butyric acid, and 0.002 parts by weight of p-toluenesulfonic acid was prepared in a beaker. Next, 21.4 parts by weight (0.2 mol) of 2-(2-vinyloxyethoxy)ethyl acrylate was added dropwise to the mixture, taking care to avoid heat buildup. After the addition was complete, the mixture was stirred at 30°C for 3 hours. 0.12 parts by weight of triethylamine was added and stirred, and the resulting solution was used as the addition tank (B). As the initiator tank, a solution of 2.0 parts by weight of 2,2'-azobis(2,4-dimethylvaleronitrile) and 28.0 parts by weight of propylene glycol monomethyl ether acetate was prepared in a beaker and stirred. After the reaction tank temperature reached 60°C, polymerization was continued over 3 hours from the addition tanks (A) and (B), as well as the initiator tank, while maintaining the same temperature. The total of 30 parts by weight of the initiator tank was added to the reaction tank in six separate batches of 5 parts each, starting at 0 minutes, 30 minutes, 1 hour, 1.5 hours, 2 hours, and 2.5 hours after the start of polymerization. After the addition was complete, the mixture was aged for 1 hour while maintaining the temperature at 60°C. The temperature was then raised to 70°C and aged for 6 hours. After cooling to room temperature, 11.5 parts by weight (0.2 mol) of succinic anhydride, 11.7 parts by weight of triethylamine, and 29.6 parts by weight of propylene glycol monomethyl ether acetate were added to the reaction vessel and reacted at 50°C for 1 hour. After the reaction, the mixture was cooled to room temperature to obtain alkali-soluble resin B-1 (Mw: 15,200, AV 61 mgKOH / g, solids content 29.1% by weight).

[0254] Synthesis Example 2: Synthesis of Alkali-Soluble Resin B-2

[0255] In a reaction vessel equipped with a thermometer, a stirrer, a gas inlet pipe, a condenser, and a dropping tank inlet port, 146.8 parts by weight of propylene glycol monomethyl ether acetate was placed, and after nitrogen substitution, the mixture was heated to 60° C. Separately, as a dropping tank (A), a solution prepared by stirring and mixing 2.0 parts by weight (0.02 mol) of N-benzylmaleimide, 35.5 parts by weight (0.37 mol) of cyclohexyl methacrylate, 1.0 part by weight (0.02 mol) of methyl methacrylate, 30.0 parts by weight (0.4 mol) of 2-hydroxyethyl methacrylate, 30.0 parts by weight of propylene glycol monomethyl ether acetate, and 2.0 parts by weight of n-dodecylmercaptan was prepared in a beaker. As a dropping tank (B), a uniform mixed solution prepared by charging and stirring 28.5 parts by weight of propylene glycol monomethyl ether acetate, 10.1 parts by weight (0.2 mol) of butyric acid, and 0.002 parts by weight of p-toluenesulfonic acid was prepared in a beaker. Next, while paying attention to heat generation, 21.4 parts by weight (0.2 mol) of 2-[2-(vinyloxy)ethoxy]ethyl 2-acrylate was added dropwise to the above mixed solution. After the addition was completed, the mixture was stirred at 30°C for 3 hours. 0.12 parts by weight of triethylamine was added and stirred, and the resulting solution was used as the addition tank (B). As the initiator tank, a solution of 2.0 parts by weight of 2,2'-azobis(2,4-dimethylvaleronitrile) and 28.0 parts by weight of propylene glycol monomethyl ether acetate was prepared and stirred in a beaker. After the reaction tank temperature reached 60°C, polymerization was carried out by adding dropwise additions to the reaction tanks (A) and (B) and the initiator tank over 3 hours while maintaining the same temperature. A total of 30 parts by weight of the initiator tank was added to the reaction tank in six separate batches of 5 parts each, at 0 minutes, 30 minutes, 1 hour, 1.5 hours, 2 hours, and 2.5 hours after the start of polymerization. After the addition was complete, the mixture was aged for 1 hour while maintaining the temperature at 60°C. The temperature was then raised to 70°C and aged for 6 hours. After cooling to room temperature, 11.5 parts by weight (0.2 mol) of succinic anhydride, 11.7 parts by weight of triethylamine, and 29.6 parts by weight of propylene glycol monomethyl ether acetate were added to the reaction vessel and reacted at 50°C for 1 hour. After the reaction, the mixture was cooled to room temperature to obtain alkali-soluble resin B-2 (Mw: 16,300, AV 63 mgKOH / g, solids content 29.5% by weight).

[0256] Synthesis Example 3: Synthesis of Alkali-Soluble Resin B-3

[0257] Alkali-soluble resin B-3 (Mw: 15,900, AV 66 mgKOH / g, solid content 29.3 wt %) was obtained in the same manner as in Synthesis Example 1 except that propionic acid was used instead of butyric acid.

[0258] Synthesis Example 4: Synthesis of Alkali-Soluble Resin B-4

[0259] Alkali-soluble resin B-4 (Mw: 16,430, AV 67 mgKOH / g, solid content 29.6 wt %) was obtained in the same manner as in Synthesis Example 1 except that undecanoic acid was used instead of butyric acid.

[0260] Synthesis Example 5: Synthesis of Alkali-Soluble Resin B-6

[0261] A 1000 ml flask equipped with a stirrer, thermometer, reflux condenser, dropping funnel, and nitrogen inlet tube was charged with 300 parts by weight of propylene glycol monomethyl ether acetate, 7 parts by weight of AIBN, 15 parts by weight of tricyclodecyl methacrylate, 30 parts by weight of methyl methacrylate, 20 parts by weight of methacrylic acid, and 15 parts by weight of 2-hydroxyethyl methacrylate, and the atmosphere was purged with nitrogen (reaction tank A). The reaction mixture was then stirred and the temperature was raised to 80°C. 22 parts by weight of 2-(2-oxiethyl)ethyl 2-acrylate was diluted with 100 parts by weight of propylene glycol monomethyl ether acetate (reaction tank B). This reaction mixture was then added to reaction tank A in six portions at 30-minute intervals while stirring. After completion of the additions, the mixture was allowed to react for 3.5 hours, and then terminated to obtain epoxy-containing alkali-soluble resin B-6. The epoxy group-containing alkali-soluble resin B-6 synthesized in this manner had a final solid content of 28.0% by weight, a solid content acid value of 62 mgKOH / g, and a weight average molecular weight as measured by GPC of 14,300.

[0262] Synthesis Example 6: Synthesis of Alkali-Soluble Resin B-7

[0263] A 1000 ml flask equipped with a stirrer, thermometer, reflux condenser, dropping funnel, and nitrogen inlet tube was charged with 300 parts by weight of propylene glycol monomethyl ether acetate, 7 parts by weight of AIBN, 15 parts by weight of tricyclodecyl methacrylate, 30 parts by weight of methyl methacrylate, 20 parts by weight of methacrylic acid, and 15 parts by weight of 2-hydroxyethyl methacrylate, and the atmosphere was purged with nitrogen (reaction tank A). The reaction mixture was then stirred and the temperature was raised to 80°C. 22 parts by weight of 4-hydroxybutyl acrylate glycidyl ether was diluted with 100 parts by weight of propylene glycol monomethyl ether acetate (reaction tank B). This reaction mixture was then added to reaction tank A in six portions at 30-minute intervals while stirring. After completion of the additions, the mixture was allowed to react for 3.5 hours, and then terminated to obtain epoxy-containing alkali-soluble resin B-7. The epoxy-containing alkali-soluble resin B-7 synthesized in this manner had a final solid content of 28.0% by weight, a solid content acid value of 70 mgKOH / g, and a weight average molecular weight as measured by GPC of 15,100.

[0264] Examples and Comparative Examples: Preparation of Colored Photosensitive Resin Compositions

[0265] The respective components were mixed according to the composition shown in Table 1 below to produce a colored photosensitive resin composition (unit: wt %).

[0266] [Table 1]

[0267]

[0268] A-1: Pigment dispersion of Production Example 1

[0269] B-1: Vinyl ether resin of Synthesis Example 1

[0270] B-2: Vinyl ether resin of Synthesis Example 2

[0271] B-3: Vinyl ether resin of Synthesis Example 3

[0272] B-4: Vinyl ether resin of Synthesis Example 4

[0273] B-5: Acrylic resin (Resonac SPCY-1L)

[0274] B-6: Epoxy resin of Synthesis Example 5

[0275] B-7: Epoxy resin of Synthesis Example 6

[0276] C-1: Dipentaerythritol hexaacrylate (DPHA)

[0277] D-1: PBG-345 (TRONLY)

[0278] D-2: PBG-314 (TRONLY)

[0279] D-3: I-369 (Ciba)

[0280] E-1: Propylene glycol monomethyl ether acetate (PGMEA)

[0281] F-1: F-554 (DIC Corporation)

[0282] Experimental Example 1:

[0283] Color filters were produced as follows using the colored photosensitive resin compositions produced in the above Examples and Comparative Examples. The physical properties of the color filters were measured by the following methods. The results are shown in Table 2 below.

[0284] <Manufacturing of Color Filter>

[0285] Each of the colored photosensitive resin compositions was applied onto a bare glass substrate by spin coating, and then placed on a hot plate and maintained at 100° C. for 2 minutes to form a thin film.

[0286] Next, a test photomask with a pattern that changes the transmittance in steps from 1 to 100% and a line / space pattern of 1 μm to 100 μm was placed on the film, and the distance between the test photomask and the test photomask was set at 200 μm, and the film was irradiated with ultraviolet light. At this time, a 1 kW high-pressure mercury lamp that includes g, h, and i rays was used as the ultraviolet light source, and the radiation was 50 mJ / cm 2 The film was irradiated at an illumination intensity of 100°C without using any special optical filters. The film, after UV irradiation, was immersed in a KOH aqueous solution (pH 10.5) for 2 minutes for development. Post-baking was performed on a 100°C hotplate for 60 minutes. The resulting color filter pattern (film) had a thickness of 3.0 μm.

[0287] (1) Solvent resistance

[0288] The color filter produced above was immersed in a solvent (propylene glycol monomethyl ether acetate, PGMEA) at 60° C. for 5 minutes to observe whether the pattern was peeled off. The solvent resistance was evaluated according to the following evaluation criteria.

[0289] <Evaluation Criteria>

[0290] OK: The pattern remains after dipping

[0291] NG: The pattern falls off after dipping

[0292] (2) Resolution

[0293] The line / space pattern of the color filter produced as described above is observed under a microscope, and the minimum line width among the formed lines is defined as the resolution. For example, if the minimum line width among the formed lines is 7 μm, the resolution is 7 μm.

[0294] (3) Storage stability

[0295] Immediately after the colored photosensitive resin composition was prepared, a color filter was produced as described above and the initial image break point (BP), that is, the time it takes for a pattern to appear during development (unit: seconds, sec) was measured.

[0296] Furthermore, after the colored photosensitive resin composition was left to stand at room temperature (23° C.) for 7 days, a color filter was produced as described above, and BP was measured to evaluate storage stability based on the degree of BP retardation.

[0297] [Table 2]

[0298]

[0299] As shown in Table 2, the colored photosensitive resin compositions of Examples 1 to 5 of the present invention, which contain a copolymer having a repeating unit derived from a vinyl ether and a repeating unit having a carboxylic acid ammonium salt structure as an alkali-soluble resin and a carbazole oxime-based or fluorene oxime-based photopolymerization initiator having a specific structure as a photopolymerization initiator, were confirmed to have excellent solvent resistance and resolution even when cured (POB) at a low temperature of 100° C. or less, ensuring reliability, and also having high storage stability.

[0300] On the other hand, the colored photosensitive resin compositions of Comparative Examples 1 to 5 that did not satisfy any of the above-mentioned alkali-soluble resin and photopolymerization initiator showed that it was difficult to simultaneously ensure reliability and storage stability during low-temperature curing.

[0301] While specific aspects of the present invention have been described in detail above, it will be apparent to those skilled in the art that these specific techniques are merely preferred embodiments and that the scope of the present invention is not limited thereto. Based on the above, those skilled in the art should be able to apply and modify the present invention in various ways within the scope of the present invention.

[0302] Therefore, the true scope of the invention should be determined by the appended claims and their equivalents.

Claims

1. A colored photosensitive resin composition comprising a colorant, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent, The alkali-soluble resin includes a copolymer having a repeating unit represented by the following Chemical Formula 1 and a repeating unit represented by the following Chemical Formula 2, The photopolymerization initiator includes a compound represented by the following Chemical Formula 3: Chemical formula 1 Chemical formula 2 Chemical formula 3 In the formula, R a is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R b is an alkyl group having 1 to 19 carbon atoms, R c is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, R d is an alkyl group having 1 to 3 carbon atoms, n and m are each independently an integer of 1 to 3, A is -CH- or a nitrogen atom, R 1 ~ R 8 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a group represented by Chemical Formula 4, -COR 16 or -NO2, Chemical formula 4 R 13 is an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, a cycloalkenyl group having 4 to 8 carbon atoms, an alkynyl group having 2 to 12 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a phenyl group or a naphthyl group, R 14 is a hydrogen atom, a cycloalkyl group having 3 to 8 carbon atoms, an alkenyl group having 2 to 5 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms, R 15 is an aryl group having 6 to 20 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, or an alkyl group having 1 to 10 carbon atoms, R 16 is an aryl group having 6 to 20 carbon atoms which is substituted or unsubstituted with one or more substituents selected from the group consisting of an alkoxy group having 1 to 20 carbon atoms and an alkyl group having 1 to 20 carbon atoms, X does not exist or is -CO-, * indicates a bond.

2. The colored photosensitive resin composition according to claim 1 , wherein the content of the repeating unit represented by Chemical Formula 1 is 10 to 40 mol % relative to 100 mol % of all repeating units constituting the alkali-soluble resin.

3. The colored photosensitive resin composition according to claim 1 , wherein the content of the repeating unit represented by Chemical Formula 2 is 10 to 40 mol % relative to 100 mol % of all repeating units constituting the alkali-soluble resin.

4. The colored photosensitive resin composition according to claim 1, wherein R 1 and R 2 、R 2 and R 3 、R 3 and R 4 、R 5 and R 6 、R 6 and R 7 , or R 7 and R 8 At least one pair of them is a group represented by the following chemical formula 5: Chemical formula 5 In the formula, The R 9 ~ R 12 Each is independently a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, or a substituted or unsubstituted phenyl group. 5 . A colored pattern formed using the colored photosensitive resin composition according to claim 1 . A color filter comprising the colored pattern according to claim 5 .

7. An image display device, characterized in that: A color filter according to claim 6 is provided.

8. A solid-state imaging element, characterized in that: A color filter according to claim 6 is provided.

Images