Colored Photosensitive Resin Composition, Color Filter, Display Device and Solid State Imaging Device

Abstract

The present invention provides a colored photosensitive resin composition comprising a coloring agent, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent, wherein the photopolymerization initiator comprises an oxime ester compound having a specific structure, a color filter formed using the same, an image display device equipped with the color filter, and a solid-state imaging element. The colored photosensitive resin composition according to the present invention has a low film shrinkage rate and low brightness reduction when forming a pattern, and can prevent the occurrence of double step differences.

Description

Technology 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, and more specifically, to a colored photosensitive resin composition that can suppress film shrinkage during pattern formation while having minimal change in brightness and preventing the occurrence of double step difference, a color filter formed using the same, an image display device equipped with the color filter, and a solid-state imaging element. Background Technology

[0002] Color filters are widely used in solid-state image sensors and liquid crystal displays (LCDs), and their range of applications is rapidly expanding. In particular, solid-state image sensors are elements created using integrated circuit technology that convert optical images into electrical signals. Recently, as the pixel count of color filters used in solid-state image sensors such as CCDs and CMOS has increased, the pixels of solid-state image sensors have become smaller, and there is a demand to make the film thickness even thinner.

[0003] Color filters are typically manufactured by forming pixels of each color by uniformly applying a colored photosensitive resin composition containing pigments corresponding to each color (red, green, and blue) onto a substrate patterned with a black matrix, then exposing and developing the film formed by heat drying, and repeating the operation of further heat curing for each color.

[0004] Korean Patent Publication No. 10-2009-0072754 discloses a photosensitive resin composition for a color filter comprising a pigment and a binder resin.

[0005] However, there is still a need for the development of a colored photosensitive resin composition that can suppress film shrinkage during pattern formation, exhibit minimal changes in brightness, and prevent the occurrence of double step differences. Prior art literature

[0006] Republic of Korea Published Patent No. 10-2009-0072754 The problem to be solved

[0007] One objective of the present invention is to provide a colored photosensitive resin composition that can suppress film shrinkage during pattern formation, has low brightness change, and has excellent taper characteristics to prevent the occurrence of double step differences.

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

[0009] Another objective of the present invention is to provide an image display device and a solid-state imaging element equipped with the color filter. means of solving the problem

[0010] On the one hand, the present invention relates to a colored photosensitive resin composition comprising a coloring agent, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent, wherein

[0011] The present invention provides a colored photosensitive resin composition comprising an oxime ester compound represented by any one of the following chemical formulas 1 to 3, wherein the above photopolymerization initiator is a photopolymerization initiator.

[0012] [Chemical Formula 1]

[0013]

[0014] [Chemical Formula 2]

[0015]

[0016] [Chemical Formula 3]

[0017]

[0018] In the above formula,

[0019] R 1 , R 8 and R 11 C1-C each independently 20 It is an alkyl group or an aryl group, and

[0020] R 2 , R 3 , R 9 , R 10 , R12 and R 13 C1-C each independently 20 alkyl group of, C4-C 16 cycloalkylalkyl group of, C6-C 21 arylalkyl group of, C2-C 20 The alkoxyalkyl group or C3-C 21 It is an alkoxycarbonylalkyl group of,

[0021] Y 1 to Y 3 Each independently has a direct bond, an arylene group, or a C3-C 10 It is a cycloalkylene group, and

[0022] R 4 to R 7 , R 14 and R 15 C1-C each independently 20 alkyl group of, C4-C 16 cycloalkylalkyl group of, C6-C 21 arylalkyl group of, C2-C 20 It is an alkoxyalkyl group or an aryl group.

[0024] In one embodiment of the present invention,

[0025] R 1 C1-C 20 It is an alkyl group or an aryl group, and

[0026] R 2 and R 3 C1-C each independently 20 alkyl group of, C4-C 16 cycloalkylalkyl group of, C6-C 21 arylalkyl group or C2-C 20 It is an alkoxyalkyl group of, and

[0027] Y 1 is a directly bonded or arylene group, and

[0028] R 4 to R 7 C1-C each independently 20 It can be an alkyl group.

[0030] In one embodiment of the present invention,

[0031] R 8 C1-C 20 It is an alkyl group of, and

[0032] R 9 and R 10 C1-C each independently 20 alkyl group of, C4-C 16 cycloalkylalkyl group of, C6-C 21 arylalkyl group or C2-C 20 It is an alkoxyalkyl group of, and

[0033] Y 2 It can be an arylene group.

[0035] In one embodiment of the present invention,

[0036] R 11 C1-C 20 It is an alkyl group of, and

[0037] R 12 and R 13 C1-C each independently 20 alkyl group of, C4-C 16 cycloalkylalkyl group of, C2-C 20 The alkoxyalkyl group or C3-C 21 It is an alkoxycarbonylalkyl group of,

[0038] Y 3 is a directly bonded or arylene group, and

[0039] R 14 and R 15 C1-C each independently 20 It can be an alkyl group.

[0041] In one embodiment of the present invention,

[0042] R 1 , R 8 and R 11 Each can independently be a methyl group or a phenyl group.

[0044] In one embodiment of the present invention,

[0045] R 2 , R 3 , R 9 , R10 , R 12 and R 13 C1-C each independently 10 It may be an alkyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, a benzyl group, a methoxymethyl group, or an ethoxycarbonylmethyl group.

[0047] In one embodiment of the present invention,

[0048] Y 1 to Y 3 Each can independently be a directly bonded phenylene group or a naphthylene group.

[0050] In one embodiment of the present invention,

[0051] R 1 , R 8 and R 11 Each is independently a methyl group or a phenyl group, and

[0052] R 2 , R 3 , R 9 , R 10 , R 12 and R 13 C1-C each independently 10 It is an alkyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, a benzyl group, a methoxymethyl group, or an ethoxycarbonylmethyl group, and

[0053] Y 1 to Y 3 Each is independently a directly bonded phenylene group or a naphthylene group, and

[0054] R 4 to R 7 , R 14 and R 15 C1-C each independently 10 It can be an alkyl group.

[0056] In one embodiment of the present invention, the oxime ester compound may be included in an amount of 5 weight percent or more with respect to 100 weight percent of the total photopolymerization initiator.

[0058] On the other hand, the present invention provides a colored pattern formed using the colored photosensitive resin composition.

[0059] On the other hand, the present invention provides a color filter including the coloring pattern.

[0060] On the other hand, the present invention provides an image display device characterized by having the color filter described above.

[0061] On the other hand, the present invention provides a solid-state imaging element characterized by having the color filter described above. Effects of the invention

[0062] The colored photosensitive resin composition according to the present invention has a high molar extinction coefficient and excellent sensitivity, so by including an oxime ester compound of a specific structure as a photopolymerization initiator that can provide excellent curing degree with a small amount of exposure even when added in small amounts, film shrinkage can be suppressed during pattern formation, while having minimal change in brightness and excellent taper characteristics, thereby preventing the occurrence of double step differences. Specific details for implementing the invention

[0063] The present invention will be described in more detail below.

[0065] One embodiment of the present invention relates to a colored photosensitive resin composition comprising a coloring agent (A), an alkali-soluble resin (B), a photopolymerizable compound (C), a photopolymerization initiator (D), and a solvent (E), wherein the photopolymerization initiator (D) comprises an oxime ester compound having a specific structure.

[0067] Colorant (A)

[0068] In one embodiment of the present invention, the coloring agent (A) comprises a pigment (a1) and / or a dye (a2).

[0070] pigment (a1)

[0071] The above pigment may be an organic pigment or an inorganic pigment commonly used in the field.

[0072] The above organic pigments may include various pigments used in printing inks, inkjet inks, etc. Specifically, examples include water-soluble azo pigments, insoluble azo pigments, phthalocyanine pigments, quinacridone pigments, isoindolinone pigments, isoindoline pigments, perirene pigments, perirone pigments, dioxazine pigments, anthraquinone pigments, dianthraquinonyl pigments, anthrapyrimidine pigments, anthanthrone pigments, indanthrone pigments, prabantron pigments, pyranthrone pigments, diketopyrrolopyrrole pigments, etc.

[0073] Examples of the above-mentioned inorganic pigments include metal compounds such as metal oxides or metal complex salts, and specifically, examples include oxides or complex metal oxides of metals such as iron, cobalt, aluminum, cadmium, lead, copper, titanium, magnesium, chromium, zinc, and antimony; carbon black, etc.

[0074] In particular, the above organic and inorganic pigments may specifically 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 to these.

[0075] 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

[0076] CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, and 71

[0077] 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

[0078] CI Pigment Violet 14, 19, 23, 29, 32, 33, 36, 37 and 38

[0079] CI Pigment Blue 15 (15:3, 15:4, 15:6, etc.), 21, 28, 60, 64, and 76

[0080] CI Pigment Green 7, 10, 15, 25, 36, 47, and 58

[0081] CI Pigment Brown 28

[0082] CI Pigment Black 1 and 7, etc.

[0084] These can each be used individually or in combination of two or more types.

[0085] It is preferable to use a pigment dispersion in which the above pigment has a uniformly dispersed particle size. As an example of a method for uniformly dispersing the particle size of the pigment, a method of dispersion treatment containing a pigment dispersant (a3) ​​can be cited, and according to this method, a pigment dispersion in which the pigment is uniformly dispersed in a solution can be obtained.

[0087] Pigment dispersant (a3)

[0088] The pigment dispersant (a3) ​​above is added to prevent the pigment from clumping and to maintain stability. Specific examples of pigment dispersants include cationic, anionic, nonionic, amphoteric, polyester, and polyamine surfactants, and each of these can be used individually or in combination of two or more types.

[0089] In addition, it is preferable to include an acrylate-based dispersant (hereinafter referred to as an acrylate-based dispersant) comprising butyl methacrylate (BMA) or N,N-dimethylaminoethyl methacrylate (DMAEMA). Examples of commercially available acrylate-based dispersants include DISPER BYK-2000, DISPER BYK-2001, DISPER BYK-2070, or DISPER BYK-2150, and each of the acrylate-based dispersants may be used individually or in combination of two or more types.

[0090] The pigment dispersant (a3) ​​above may use a pigment dispersant of a different resin type in addition to the acrylate-based dispersant described above. The pigment dispersant of the different resin type above may be a known resin type pigment dispersant, in particular a dispersant of a quality such as a polyurethane, a polycarboxylic acid ester represented by polyacrylate, an unsaturated polyamide, a polycarboxylic acid, a (partial) amine salt of a polycarboxylic acid, an ammonium salt of a polycarboxylic acid, an alkylamine salt of a polycarboxylic acid, a polysiloxane, a long-chain polyaminoamide phosphate salt, an ester of a hydroxyl group-containing polycarboxylic acid and its modification products, or an amide or salt thereof formed by the reaction of a polyester having a free carboxyl group with a poly(lower alkyleneimine); Examples include water-soluble resins or water-soluble polymer compounds such as (meth)acrylic acid-styrene copolymer, (meth)acrylic acid-(meth)acrylate ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol or polyvinylpyrrolidone; polyesters; modified polyacrylates; ethylene oxide / propylene oxide adducts and phosphate esters.

[0091] Commercially available resin-type dispersants mentioned above include cationic resin dispersants, for example, BYK Chem’s trade names: DISPER BYK-160, DISPER BYK-161, DISPER BYK-162, DISPER BYK-163, DISPER BYK-164, DISPER BYK-166, DISPER BYK-171, DISPER BYK-182, DISPER BYK-184; BASF product names: EFKA-44, EFKA-46, EFKA-47, EFKA-48, EFKA-4010, EFKA-4050, EFKA-4055, EFKA-4020, EFKA-4015, EFKA-4060, EFKA-4300, EFKA-4330, EFKA-4400, EFKA-4406, EFKA-4510, EFKA-4800; Lubrizol product names: SOLSPERS-24000, SOLSPERS-32550, NBZ-4204 / 10; Kawaken Fine Chemical product names: HINOACT T-6000, HINOACT T-7000, HINOACT T-8000; Examples include Ajinomoto's product names: Ajisper PB-821, Ajisper PB-822, Ajisper PB-823; Kyoei Chemical's product names: Florene DOPA-17HF, Florene DOPA-15BHF, Florene DOPA-33, Florene DOPA-44, etc.

[0092] In addition to the acrylic dispersant mentioned above, other resin-type pigment dispersants may be used individually or in combination of two or more types, and may also be used in combination with the acrylic dispersant.

[0093] 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 pigment (a1). If the content of the pigment dispersant (a3) ​​exceeds 60 parts by weight, the viscosity may increase, and if it is less than 5 parts by weight, it may be difficult to finely pulverize the pigment or cause problems such as gelation after dispersion.

[0095] dye(a2)

[0096] The above dye (a2) may be used without limitation as long as it has solubility in organic solvents. Preferably, it is desirable to use a dye that has solubility in organic solvents and can ensure reliability such as solubility in alkaline developer, heat resistance, and solvent resistance.

[0097] The above dye may be selected from acid dyes having acidic groups such as sulfonic acid or carboxylic acid, salts of acid dyes and nitrogen-containing compounds, sulfonamide-based acid dyes, and derivatives thereof, and in addition, azo-based, xanthenic-based, and phthalocyanine-based acid dyes and derivatives thereof may also be selected.

[0098] Preferably, the above dye may be a compound classified as a dye in the Color Index (published by The Society of Dyers and Colourists) or a known dye listed in dyeing notes (color dyes).

[0099] Specific examples of the above dyes include CI solvent dyes,

[0100] Yellow dyes such as CI solvent yellow 4, 14, 15, 16, 21, 23, 24, 38, 56, 62, 63, 68, 79, 82, 93, 94, 98, 99, 151, 162, 163;

[0101] Red dyes such as CI Solvent Red 8, 45, 49, 89, 111, 122, 125, 130, 132, 146, 179;

[0102] CI solvent orange orange dyes such as 2, 7, 11, 15, 26, 41, 45, 56, 62, etc.;

[0103] Blue dyes such as CI solvent blue 5, 35, 36, 37, 44, 59, 67, 70;

[0104] Violet dyes such as CI solvent violet 8, 9, 13, 14, 36, 37, 47, 49;

[0105] Examples include green dyes such as CI solvent green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35.

[0106] Among them, 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, are preferred, and among them, CI solvent yellow 21, 79; CI solvent red 8, 122, 132; and CI solvent orange 45, 62 are more preferred.

[0107] In addition, as a CI acid dye,

[0108] CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, Yellow dyes such as 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;

[0109] CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 34, 35, 37, 42, 44, 50, 51, 52, 57, 66, 73, 80, 87, 88, 91, 92, 94, 97, 103, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 158, 176, 182, 183, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, Red dyes such as 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;

[0110] CI Acid Orange orange dyes such as 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;

[0111] Blue dyes such as CI Acid Blue 1, 7, 9, 15, 18, 23, 25, 27, 29, 40, 42, 45, 51, 62, 70, 74, 80, 83, 86, 87, 90, 92, 96, 103, 112, 113, 120, 129, 138, 147, 150, 158, 171, 182, 192, 210, 242, 243, 256, 259, 267, 278, 280, 285, 290, 296, 315, 324:1, 335, 340;

[0112] Violet dyes such as CI acid violet 6B, 7, 9, 17, 19, 66;

[0113] Examples of green dyes include CI acid green 1, 3, 5, 9, 16, 25, 27, 50, 58, 63, 65, 80, 104, 105, 106, 109, etc.

[0114] Among them, CI acid yellow 42; CI acid red 52, 92; CI acid blue 80, 90; CI acid violet 66; and CI acid green 27, which have excellent solubility in organic solvents among acid dyes, are preferred.

[0115] In addition, as a CI Direct dye,

[0116] 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;

[0117] Red dyes such as CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250;

[0118] Orange dyes such as CI Direct Orange 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

[0119] CI Direct Blue 38, 44, 57, 70, 77, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 166, 167, 170, 171, 172, 173, 188, 189, 190, 192, Blue dyes of 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.;

[0120] Violet dyes such as CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

[0121] Examples of green dyes include CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82, etc.

[0122] In addition, as a CI modanto dye,

[0123] Yellow dyes such as CI Modanto Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

[0124] Red dyes such as CI Modanto 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;

[0125] Orange dyes such as CI Modanto Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;

[0126] Blue dyes such as CI Modanto 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;

[0127] Violet dyes such as CI Modanto Violet 1, 2, 4, 5, 7, 14, 22, 24, 30, 31, 32, 37, 40, 41, 44, 45, 47, 48, 53, 58;

[0128] Examples of green dyes include CI Modanto Green 1, 3, 4, 5, 10, 15, 19, 26, 29, 33, 34, 35, 41, 43, 53, etc.

[0129] In the present invention, the dyes (a2) can each be used individually or in combination of two or more types.

[0131] In particular, the above coloring agent (A) is a red coloring agent, a green coloring agent, or a blue coloring agent.

[0132] The above red coloring agent comprises one or more of diketopyrrolopyrrole-based red pigments and anthraquinone-based red pigments, preferably a combination thereof, in terms of optical properties such as luminance.

[0133] The above diketopyrrolopyrrole-based red pigment is a red pigment having a diketopyrrolopyrrole or an analog thereof backbone, and may include one or more of CI Pigment Red 254, 255, 264, 270 and 272.

[0134] In particular, the above-mentioned diketopyrrolopyrrole-based red pigment may include CI Pigment Red 254 in terms of optical properties.

[0135] The above anthraquinone-based red pigment is a red pigment having an anthraquinone or an analog thereof backbone, and may include CI Pigment Red 177.

[0136] When the above-mentioned diketopyrrolopyrrole-based red pigment and anthraquinone-based red pigment are used in combination, the mixing ratio of the diketopyrrolopyrrole-based red pigment and the anthraquinone-based red pigment may be 9:1 to 1:9 by weight, preferably 8:2 to 3:7, and more preferably 7:3 to 5:5.

[0138] The above green coloring agent includes a halogenated phthalocyanine-based green pigment in terms of optical properties such as brightness.

[0139] The above halogenated phthalocyanine-based green pigment is a green pigment having a halogenated phthalocyanine or an analog thereof backbone, and may include one or more of CI Pigment Green 7, 36, 58, 59, 62 and 63.

[0140] In particular, the above halogenated phthalocyanine-based green pigment may include one or more of CI pigment greens 58 and 59 in terms of optical properties.

[0141] In one embodiment of the present invention, the green coloring agent may further include a quinophthalone-based yellow pigment in terms of optical properties such as brightness.

[0142] The above quinophthalone-based yellow pigment is a yellow pigment having a quinophthalone or an analog skeleton, and may include CI Pigment Yellow 138.

[0143] The above quinophthalone-based yellow pigment may be included in an amount of 50% by weight or less, preferably 10 to 40% by weight, based on 100% by weight of the total green coloring agent.

[0145] The above blue coloring agent comprises one or more of phthalocyanine-based blue pigments and triphenylmethane-based blue dyes in terms of optical properties such as brightness.

[0146] The above phthalocyanine-based blue pigment is a blue pigment having a phthalocyanine or analog skeleton, and may include one or more of CI pigment blue 15:3, 15:4, 15:6 and 16.

[0147] In particular, the above phthalocyanine-based blue pigment may include CI pigment blue 15:6 in terms of optical properties.

[0148] The above triphenylmethane-based blue dye may include a compound represented by the following chemical formula 7.

[0149] [Chemical Formula 7]

[0150]

[0151] In the above formula,

[0152] R 16 ~R 19 and R 28 It represents a hydrocarbon group having 1 to 10 carbon atoms that may independently have hydrogen atoms or substituents, and

[0153] R 20 ~R 27 It represents a hydrocarbon group having 1 to 5 carbon atoms that may independently have hydrogen atoms, halogen atoms, or substituents, and

[0154] T 1 It represents a divalent aromatic hydrocarbon group that may have substituents, and

[0155] T 2represents a divalent aromatic hydrocarbon group that may have substituents or a divalent aromatic complex group that may have substituents, and

[0156] L 1 ... represents an aliphatic hydrocarbon group having 1 to 12 carbon atoms that may have a substituent, or a group represented by the following formula (i),

[0157]

[0158] T 3 represents an aromatic hydrocarbon group of α that may have substituents or an aromatic complex group of α that may have substituents, and

[0159] L 2 represents a divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms that may have substituents, and

[0160] * is T 2 Represents the bonding hand with,

[0161] X c- represents the anion of c, and

[0162] a represents an integer greater than or equal to 2, and

[0163] b and c independently represent integers greater than or equal to 1, and

[0164] d represents an integer greater than or equal to 0.

[0166] The compound represented by the above chemical formula 7 is a blue dye with high brightness and good colorability, which allows for a reduction in the pigment content of the composition, making it advantageous for thin film fabrication, and it serves to adjust the transmission spectrum and color coordinates when used together with the xanthen dye described later.

[0168] Examples of hydrocarbon groups having 1 to 10 carbon atoms used in this specification include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. In this case, the aliphatic hydrocarbon group may be saturated or unsaturated, and may be chain-like or alicyclic.

[0169] The above-mentioned saturated or unsaturated chain hydrocarbon groups include straight-chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl groups; Branched-chain alkyl groups such as isopropyl group, (1-ethyl)propyl group, isobutyl group, sec-butyl group, tert-butyl group, (1-ethyl)butyl group, (2-ethyl)butyl group, (1-propyl)butyl group, isopentyl group, neopentyl group, tert-pentyl group, (2-methyl)pentyl group, (1-ethyl)pentyl group, (3-ethyl)pentyl group, (1-propyl)pentyl group, (1-butyl)pentyl group, isohexyl group, (2-methyl)hexyl group, (5-methyl)hexyl group, (2-ethyl)hexyl group, (1-butyl)hexyl group, (2-methyl)heptyl group, (2-ethyl)heptyl group, (3-ethyl)heptyl group, (2-methyl)octyl group, (2-ethyl)octyl group, etc. Examples include alkenyl groups such as vinyl groups, 1-propenyl groups, 2-propenyl groups (allyl groups), (1-methyl)ethenyl groups, 2-butenyl groups, 3-butenyl groups, 1,3-butadienyl groups, (1-(2-propenyl))ethenyl groups, (1,2-dimethyl)propenyl groups, and 2-pentenyl groups.

[0170] Examples of the above saturated or unsaturated alicyclic hydrocarbon groups include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl groups; cycloalkenyl groups such as cyclohexenyl (e.g., cyclohexa-2-ene, cyclohexa-3-ene), cycloheptenyl, and cyclooctyl groups; norbornyl, adamantyl, and bicyclo[2,2]octyl groups.

[0171] Examples of the above aromatic hydrocarbon groups include aryl groups such as phenyl groups, 1-naphthyl groups, and 2-naphthyl groups; alkylaryl groups such as o-tolyl groups, m-tolyl groups, p-tolyl groups, 2-ethylphenyl groups, 3-ethylphenyl groups, 4-ethylphenyl groups, 2,3-dimethylphenyl groups, 2,4-dimethylphenyl groups, 2,5-dimethylphenyl groups, 2,6-dimethylphenyl groups, 3,4-dimethylphenyl groups, 3,5-dimethylphenyl groups, 2-methyl-6-ethylphenyl groups, 2,6-diethylphenyl groups, o-isopropylphenyl groups, m-isopropylphenyl groups, p-isopropylphenyl groups, 2-methyl-6-isopropylphenyl groups, o-tert-butylphenyl groups, m-tert-butylphenyl groups, and p-tert-butylphenyl groups; and alkenylaryl groups such as 4-vinylphenyl groups.

[0172] The hydrocarbon groups having 1 to 10 carbon atoms described above may include a combination of two or more of the above chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups, provided that the upper limit of the number of carbon atoms is 10. Such groups include, for example, aralkyl groups such as benzyl groups, phenethyl groups, and 1-methyl-1-phenylethyl groups; aryl alkenyl groups such as phenylethenyl groups (phenylvinyl groups); and aryl alkenyl groups such as phenylethinyl groups. 1-methylcyclopropyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2,2-dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, 2,4,6-trimethylcyclohexyl group, 2,6,6-trimethylcyclohexyl group, Examples include a cyclocyclic hydrocarbon group substituted with an alkyl group such as a 3,3,5,5-tetramethylcyclohexyl group; and an alkyl group to which one or more cyclocyclic hydrocarbon groups such as a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclobutylethyl group, a cyclopentylmethyl group, a cyclopentylethyl group, a cyclohexylmethyl group, a 2-methylcyclohexylmethyl group, and a cyclohexylethyl group are bonded.

[0173] The substituents that the above C1-to-C0 hydrocarbon group may have (hereinafter referred to as substituent A) include a halogen atom, a hydroxyl group, an alkoxy group, a formyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, -SO3 - It may be at least one selected from the group consisting of and -SO3M, where M represents a hydrogen atom or an alkali metal atom.

[0174] Examples of the above halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms, and examples of the above alkoxy groups include carbon 1 to 4 alkoxy groups such as methoxy groups, ethoxy groups, propoxy groups, and butoxy groups.

[0175] The above-mentioned substituted amino group may be an amino group having one or two hydrocarbon groups, and the hydrocarbon group may be the group exemplified as the hydrocarbon group having 1 to 10 carbon atoms described above.

[0176] Examples of the above-mentioned substituted amino groups include N-methylamino group, N,N-dimethylamino group, N-ethylamino group, N,N-diethylamino group, N-propylamino group, N,N-dipropylamino group, N-isopropylamino group, N,N-diisopropylamino group, N-phenylamino group, N,N-diphenylamino group, N,N-ethylmethylamino group, N,N-methylphenylamino group, N,N-ethylphenylamino group, etc.

[0177] R 20 ~R 27 Halogen atoms that appear in this include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

[0178] R 20 ~R 27 Examples of hydrocarbon groups having 1 to 5 carbon atoms represented by include aliphatic hydrocarbon groups having 1 to 5 carbon atoms, and specifically, the above R 16 ~R 19 and R 28 Among the groups exemplified as aliphatic hydrocarbon groups, groups with 1 to 5 carbon atoms can be cited.

[0179] Examples of substituents that may be present in the above hydrocarbon group having 1 to 5 carbon atoms include those shown as examples of substituent A.

[0180] T 1 and T 2 The divalent aromatic hydrocarbon group indicated herein is a group in which two hydrogen atoms directly bonded to the carbon atoms constituting the ring in an aromatic hydrocarbon ring are replaced by bonding hands. The aromatic hydrocarbon rings constituting the divalent aromatic hydrocarbon group can be both single rings and condensed rings; examples include benzene rings, naphthalene rings, anthracene rings, or structures in which at least one hydrogen atom of these aromatic hydrocarbon rings is substituted with a hydrocarbon group. In this case, the hydrocarbon group is the above R 16 ~R 19 and R 28 Examples of hydrocarbon groups having 1 to 10 carbon atoms may be provided, preferably saturated chain hydrocarbon groups, aryl groups, or alkylaryl groups, and more preferably saturated chain hydrocarbon groups having 1 to 4 carbon atoms. The number of hydrocarbon groups bonded to the aromatic hydrocarbon is preferably 0 to 4, and more preferably 0 to 3.

[0181] Specifically, divalent aromatic hydrocarbon groups include groups represented by the following chemical formulas (Ta-1) to (Ta-8).

[0182]

[0183] T 2The divalent aromatic complex group shown in [the figure] is a group in which two hydrogen atoms directly bonded to the atoms constituting the ring in an aromatic complex are replaced by bonding hands. The aromatic complexes constituting the divalent aromatic complex group can be both single rings and condensed rings, and examples include the pyrrole ring, oxazole ring, pyrazol ring, imidazole ring, thiazole ring, furan ring, thiophene ring, pyrimidine ring, pyridazine ring, pyrazine ring, indole ring, benzimidazole ring, quinoline ring, benzofuran ring, and structures in which the hydrogen atoms of these aromatic complexes are substituted with hydrocarbon groups.

[0184] At this time, examples of hydrocarbon groups include the aforementioned R 16 ~R 19 and R 28 Examples of hydrocarbon groups having 1 to 10 carbon atoms may be provided, preferably saturated chain hydrocarbon groups, aryl groups, or alkylaryl groups. The number of hydrocarbon groups bonded to the aromatic heterocyclic ring is preferably 0 to 4, and more preferably 0 to 3.

[0185] The above divalent aromatic hydrocarbon group and divalent aromatic heterocyclic group may have a substituent such as the group exemplified as substituent A.

[0186] L 1 The aliphatic hydrocarbon group of a value of α having 1 to 12 carbon atoms shown in [formula] is a group in which a number of hydrogen atoms constituting the aliphatic hydrocarbon are replaced by bonding hands. It is preferable that the a number of bonding hands exist on different carbon atoms. Examples of aliphatic hydrocarbon groups of a value of α include chain hydrocarbon groups of α, alicyclic hydrocarbon groups of α, and a group of α that is a combination of a chain hydrocarbon and alicyclic hydrocarbon groups.

[0187] The above-mentioned chain hydrocarbon group of a may be saturated or unsaturated, but it is preferable that it be a saturated chain hydrocarbon group of a. Examples of saturated chain hydrocarbon groups of a include alkanedyl groups such as methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and hexane-1,6-diyl; and groups represented by the following chemical formulas (a-1) to (a-3). The number of carbon atoms in the chain hydrocarbon group of a is preferably 1 to 8, and 1 to 6 is more preferable.

[0188]

[0189] The above a-valent alicyclic hydrocarbon group may be saturated or unsaturated, but a saturated alicyclic hydrocarbon group is preferred. Examples of a saturated alicyclic hydrocarbon groups include divalent saturated alicyclic hydrocarbon groups such as cyclohexyl-1,2-diyl group, cyclohexyl-1,4-diyl group, norbornan-2,5-diyl group; trivalent saturated alicyclic hydrocarbon groups such as cyclohexyl-1,3,5-triyl group; and tetravalent saturated alicyclic hydrocarbon groups such as cyclohexyl-1,2,4,5-tetrayl group. The number of carbon atoms in the alicyclic hydrocarbon group is preferably 3 to 10, and 3 to 6 is more preferred.

[0190] As for the group of a value of a combined chain hydrocarbon group and alicyclic hydrocarbon group, it is preferable that the group of a value of a combined at least one chain hydrocarbon group and at least one saturated alicyclic hydrocarbon group be a combined group of a combined chain hydrocarbon group, and examples include the groups represented by the following formulas (a-4) to (a-7).

[0191]

[0192] The above-mentioned aliphatic hydrocarbon group having 1 to 12 carbon atoms may have a substituent as exemplified by substituent A.

[0193] L 1 is the contribution expressed by the following equation (i).

[0194]

[0195] In the above equation (i), T 3 The aromatic hydrocarbon group of a valence a represented in [the figure] is a group in which a number of hydrogen atoms directly bonded to the carbon atoms constituting the ring in an aromatic hydrocarbon ring are replaced by bonding hands. An example of an aromatic hydrocarbon ring constituting an aromatic hydrocarbon group of a valence a is the structure described earlier as an aromatic hydrocarbon ring constituting a divalent aromatic hydrocarbon group.

[0196] In equation (i), T 3 An aromatic complex group of a valence a, as shown in [the figure], is a group in which a number of hydrogen atoms that are directly bonded to the atoms constituting the ring in an aromatic complex are replaced by bonding hands. An aromatic complex group that constitutes an aromatic complex group of a valence a can be described as the structure explained earlier as an aromatic complex group that constitutes a divalent aromatic complex group.

[0197] The above-mentioned aromatic hydrocarbon group and aromatic complex group of a can be substituents, such as the group exemplified by substituent A.

[0198] In equation (i), L 2 Examples of divalent aliphatic hydrocarbon groups having 1 to 5 carbon atoms shown in the figure include divalent chain hydrocarbon groups having 1 to 5 carbon atoms and divalent alicyclic hydrocarbon groups having 1 to 5 carbon atoms.

[0199] The divalent chain hydrocarbon group may be saturated or unsaturated, but a divalent saturated chain hydrocarbon group is preferred. Examples of divalent saturated chain hydrocarbon groups include alkanedyl groups such as methylene groups, ethylene groups, propane-1,2-diyl groups, propane-1,3-diyl groups, butane-1,4-diyl groups, and pentane-1,5-diyl groups.

[0200] The divalent alicyclic hydrocarbon group may be saturated or unsaturated, but it is preferable that it be a divalent saturated alicyclic hydrocarbon group. Examples of divalent saturated alicyclic hydrocarbon groups include cyclopropyl-1,2-diyl groups and cyclobutyl-1,3-diyl groups.

[0201] The above divalent aliphatic hydrocarbon group having 1 to 5 carbon atoms may have a substituent such as the group exemplified as substituent A.

[0202] X c- Examples of the c-valent anions represented in this equation include known anions, specifically halogenated ions such as fluoride ions, chloride ions, bromide ions, and iodide ions. , Boron-containing ions, aluminum-containing ions, fluorine-containing Examples include anions containing at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus, and oxygen as an essential element.

[0203] Examples of the above boron-containing anions and aluminum-containing anions include anions represented by the following chemical formula 9.

[0204] [Chemical Formula 9]

[0205]

[0206] In the above equation, W 1 and W 2 represents a group having two substituents formed by releasing a proton from a monovalent proton-donating substituent independently, and M represents boron or aluminum.

[0207] A group having two substituents formed by releasing a proton from the above-mentioned monovalent proton-donating substituent may be a group formed by releasing a proton from each of the two proton-donating substituents in a compound having at least two monovalent proton-donating substituents (e.g., hydroxyl group, carboxylic acid group, etc.). The corresponding compound is preferably selected from catechol that may have a substituent, 2,3-dihydroxynaphthalene that may have a substituent, 2,2'-biphenol that may have a substituent, 3-hydroxy-2-naphthoic acid that may have a substituent, 2-hydroxy-1-naphthoic acid that may have a substituent, binaphthol that may have a substituent, salicylic acid that may have a substituent, benzilic acid that may have a substituent, or mandelic acid that may have a substituent.

[0208] In the preferred example compounds described above, substituents may include saturated hydrocarbon groups (e.g., alkyl groups, cycloalkyl groups, etc.), halogen atoms, haloalkyl groups, hydroxyl groups, amino groups, nitro groups, alkoxy groups, etc.

[0209] Salicylic acids that may have the above substituents include salicylic acid, 3-methyl salicylic acid, 3-tert-butyl salicylic acid, 3-methoxysalicylic acid, 3-nitrosalicylic acid, 4-trifluoromethyl salicylic acid, 3,5-di-tert-butylsalicylic acid, 3-aminosalicylic acid, 4-aminosalicylic acid, 5-aminosalicylic acid, 6-aminosalicylic acid, 3-hydroxysalicylic acid (2,3-dihydroxybenzoic acid), 4-hydroxysalicylic acid (2,4-dihydroxybenzoic acid), 5-hydroxysalicylic acid (2,5-dihydroxybenzoic acid), 6-hydroxysalicylic acid (2,6-dihydroxybenzoic acid), 4,5-dihydroxysalicylic acid, 4,6-dihydroxysalicylic acid, 3-chlorosalicylic acid, Examples include 4-chlorosalicylic acid, 6-chlorosalicylic acid, 4-bromosalicylic acid, 6-bromosalicylic acid, etc.

[0210] Examples of benzilic acids that may have the above substituents include compounds of the following structure.

[0211]

[0212] Examples of mandelic acids that may have the above substituents include compounds of the following structure.

[0213]

[0215] Among the anions represented by the above chemical formula 9, a preferred anion is the anion represented by the following chemical formula 10, and specifically, anions BC-1 to BC-24 having substituents listed in Table 1 below may be cited.

[0216] [Chemical Formula 10]

[0217]

[0218]

[0220] In addition, among the anions represented by the above chemical formula 9, preferred anions include the anions BC-25 to BC-28 of the following chemical formulas 11 to 14.

[0221] [Chemical Formula 11]

[0222]

[0223] [Chemical Formula 12]

[0224]

[0225] [Chemical Formula 13]

[0226]

[0227] [Chemical Formula 14]

[0228]

[0230] Examples of the above fluorine-containing anions include anions represented by the following chemical formulas 15 to 18.

[0231] [Chemical Formula 15]

[0232]

[0233] In the above equation, W 3 and W 4 Each independently represents a fluorine atom or a fluorinated alkyl group having 1 to 4 carbon atoms, or W 3 W 4 It combines to form a fluorinated alkanedyl group having 1 to 4 carbon atoms.

[0234] [Chemical Formula 16]

[0235]

[0236] In the above equation, W 5 ~W 7 Each represents an alkyl fluorine atom or a carbon-1 to 4 fluorinated group independently.

[0237] [Chemical Formula 17]

[0238]

[0239] In the above equation, Y 1 It represents a fluorinated alkanedyl group having 1 to 4 carbon atoms.

[0240] [Chemical Formula 18]

[0241]

[0242] In the above equation, Y 2 represents a fluorinated alkyl group having 1 to 4 carbon atoms.

[0244] As for the above carbon-1 to carbon-4 fluorinated alkyl group, a perfluoroalkyl group is preferred. Suitable perfluoroalkyl groups include -CF3 and -CF2CF 3, -CF2CF2CF 3, -CF(CF3)2, -CF2CF2CF2CF 3, Examples include -CF2CF(CF3)2, -C(CF3)3, etc.

[0245] Perfluoroalkanedils are preferred as the above carbon 1 to 4 fluorinated alkanedils. As perfluoroalkanedils, -CF2-, -CF2CF2- , -CF2CF2CF2- ,-C(CF3)2-, -CF2CF2CF2CF2- You can lift the back.

[0246] X c- Examples of anions of the c-valence represented by α include anions containing at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus and oxygen as an essential element, and anions of heteropolyacids or isopolyacids containing tungsten as an essential element are preferred, and anions of phosphotungstic acid, silicotungstic acid, and tungsten-based isopolyacids are more preferred.

[0247] As anions of heteropolyacids or isopolyacids containing such tungsten as an essential element, for example, the Keggine-type phosphotungstate ion α-[PW 12 O 40 ] 3- , Dawson-type phosphotungstate ion α-[P2W 18 O 62 ] 6- , β-[P2W 18 O 62 ] 6- , Keggin-type phosphate tungstate ion α-[SiW 12 O 40 ] 4- , β-[SiW 12 O 40 ] 4- , γ-[SiW 12 O 40 ] 4- , also as another example [P2W 17 O 61 ] 10- , [P2W 15 O 56 ] 12- , [H2P2W 12 O 48 ] 12- , [NaP5W 30 O 110 ] 14- , α-[SiW9O 34 ] 10- , γ-[SiW 10 O 36 ] 8- , α-[SiW 11 O39 ] 8- , β-[SiW 11 O 39 ] 8- , [W6O 19 ] 2- , [W 10 O 32 ] 4- , WO4 2- You can lift the back.

[0248] In addition, among anions other than the anions of heteropolyacid or isopolyacid containing tungsten as an essential element, an anion composed of at least one element selected from the group consisting of silicon and phosphorus and oxygen is preferred.

[0249] As an anion composed of at least one element selected from the group consisting of silicon and phosphorus and oxygen, SiO3 2- , PO4 3- You can lift the back.

[0251] Multiple R in Chemical Formula 7 16 ~R 28 , T 1 , T 2 and L 1 Each may be the same.

[0252] R 16 ~R 19 It is preferable that each be a saturated chain hydrocarbon group having 1 to 10 carbon atoms that may independently have a substituent, an aryl group having 6 to 10 carbon atoms that may have a substituent, or an alkylaryl group having 7 to 10 carbon atoms that may have a substituent.

[0253] In particular, R 16 and R 18 Each of these is an aryl group having 6 to 10 carbon atoms that may independently have a substituent, or an alkylaryl group having 7 to 10 carbon atoms that may have a substituent, and also R 17 and R 19 It is preferable that each is a saturated chain hydrocarbon group having 1 to 10 carbon atoms, which may each independently have a substituent, and R 16and R 18 This is a phenyl group that may each independently have a substituent, and is a group having an alkyl group having 1 to 4 carbon atoms at at least one of two bonding positions that are ortho-positioned with respect to N bonded to the phenyl group, and also R 17 and R 19 It is more preferable that each is a saturated chain hydrocarbon group having 1 to 6 carbon atoms, which may each independently have a substituent, and R 16 and R 18 This is a phenyl group that may each independently have a substituent, and is a group having an alkyl group having 1 to 4 carbon atoms at at least one of two bonding positions that are ortho-positioned with respect to N bonded to the phenyl group, and also R 17 and R 19 It is more preferable that each is a saturated chain hydrocarbon group having 2 to 6 carbon atoms, which may each independently have a substituent, and R 16 and R 18 This is a phenyl group that may each independently have a substituent, and is a group having alkyl groups having 1 to 3 carbon atoms at each of the two bonding positions that are ortho positions with respect to N bonded to the phenyl group, and also R 17 and R 19 It is particularly desirable that each be a saturated chain hydrocarbon group having 2 to 6 carbon atoms, which may each have a substituent independently.

[0254] R 20 ~R 27 It is preferable that it be a hydrogen atom.

[0255] R 28 A hydrocarbon group having 1 to 6 carbon atoms that may have a hydrogen atom or a substituent is preferred, a saturated chain hydrocarbon group having 1 to 6 carbon atoms that may have a hydrogen atom or a substituent is more preferred, and a hydrogen atom, a methyl group, an ethyl group, an n-propyl group, or an isopropyl group is even more preferred.

[0256] T 1As for the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group, it is preferable that the ring be a benzene ring, a naphthalene ring, or have a structure in which at least one hydrogen atom of these rings is substituted with a saturated chain hydrocarbon group having 1 to 10 carbon atoms (preferably 1 to 4).

[0257] T 1 As such, it is more preferable that it be one of the groups represented by the above chemical formulas (Ta-1) to (Ta-8).

[0258] T 2 It is preferable that the aromatic hydrocarbon group may have a substituent, and the aromatic hydrocarbon ring constituting the divalent aromatic hydrocarbon group described above is preferably a benzene ring, a naphthalene ring, or a structure in which at least one hydrogen atom of these rings is replaced by a saturated chain hydrocarbon group having 1 to 10 carbon atoms (preferably 1 to 4 carbon atoms), and it is even more preferable that the benzene ring or a structure in which at least one hydrogen atom of the benzene ring is replaced by a saturated chain hydrocarbon group having 1 to 4 carbon atoms.

[0259] T 2 It is more preferable that the group be one of the groups represented by the following chemical formulas (Tb-1) to (Tb-8).

[0260]

[0262] L 1 is an aliphatic hydrocarbon group having 1 to 8 carbon atoms that may have a substituent, or T in the group represented by the above chemical formula (i). 3 ga is an aromatic hydrocarbon group of a that may have a substituent, and L 2 It is preferable that the group be a divalent saturated chain hydrocarbon group having 1 to 5 carbon atoms, and more preferably one of an alkanediyl group having 1 to 6 carbon atoms that may have substituents, a divalent saturated alicyclic hydrocarbon group having 3 to 10 carbon atoms that may have substituents, or a group represented by the following chemical formulas (i-1) to (i-4).

[0263]

[0265] X c- The c-valent anion represented by is preferably a halide ion or an anion containing at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus and oxygen as an essential element, more preferably a halide ion or an anion of a heteropoly acid or isopoly acid containing tungsten as an essential element, and more preferably a halide ion or an anion of an isopoly acid containing tungsten as an essential element.

[0266] The substituents (i.e., substituent A) of the compound of Chemical Formula 7 include a halogen atom, a hydroxyl group, an alkoxy group, a substituted or unsubstituted amino group, and -SO3 - It is preferable that at least one is selected from the group consisting of and -SO3M, and more preferably an alkoxy group, -SO3 - It is at least one selected from the group consisting of and -SO3M.

[0267] a is preferably an integer between 2 and 6, more preferably an integer between 2 and 4, and even more preferably 2 or 3.

[0268] c is typically 1 to 14, preferably 1 to 12, more preferably 1 to 10, even more preferably 1 to 6, and particularly preferably 1 to 4.

[0269] b and d are -SO3 that a, c, and the compound of Formula 7 have as substituents. - It is determined by the number of (hereinafter referred to as e), and generally, it is adjusted so that the total charge of Chemical Formula 7 becomes 0.

[0270] Therefore, a~d in chemical formula 7 usually satisfy the relationship of equation (z) below.

[0271] a×b = (c×d) + e ··· (z)

[0272] In the above formula, a to d represent the meanings as above, and e represents the -SO3 that the compound of Chemical Formula 7 has as a substituent. - Represents the number of

[0273] e is an integer greater than or equal to 0, preferably greater than or equal to (a+1), more preferably greater than or equal to a, and even more preferably 0 or a. In particular, when d is 1 or greater, e is 0, i.e., the compound of Formula 7 is -SO3 - It is desirable not to have, and when d is 0, it is desirable that e=a.

[0274] In addition, from the perspective of heat resistance and solvent resistance, X c- A compound is preferred in which at least one element selected from the group consisting of tungsten, molybdenum, silicon, and phosphorus and oxygen is an essential element, and d is 1 or more and e is 0.

[0276] The compound represented by the above chemical formula 7 may preferably have a transmittance (T1) at 450 nm of greater than 85% and less than 99%, and a transmittance (T2) at 730 nm of greater than 50% and less than 99%. If the compound represented by the above chemical formula 7 has such transmittance characteristics, high brightness and high color reproduction are possible, and the pigment content can be reduced, resulting in excellent reliability.

[0278] In one embodiment of the present invention, the blue coloring agent may further include a xanthenic dye.

[0279] The above xanthen dye has high brightness and good colorability, which allows for a reduction in the pigment content of the composition, making it advantageous for thin film fabrication, and it serves to adjust the transmission spectrum and color coordinates when used together with a phthalocyanine-based blue pigment or a triphenylmethane dye represented by Chemical Formula 7.

[0280] The above xanthen dye is a dye containing a compound having a xanthen backbone within its molecule.

[0281] Examples of xanthen dyes include CI Acid Red dyes such as CI Acid Red 51, 52, 87, 92, 94, 289, 388; CI Acid Violet dyes such as CI Acid Violet 9, 30, 102; CI Basic Red dyes such as CI Basic Red 1 (Rhodamine 6G), 2, 3, 4, 8, 10 (Rhodamine B), 11; CI Basic Violet dyes such as CI Basic Violet 10, 11, 25; CI Solvent Red dyes such as CI Solvent Red 218; CI Mordaunt Red dyes such as CI Mordaunt Red 27; CI Reactive Red dyes such as CI Reactive Red 36 (Rose Bengal B); Rhodamine 123; Sulphorodamine B; Sulphorodamine G; and xanthen dyes described in Japanese Patent Publication No. 2010-32999. Examples include xanthen dyes described in Japanese Patent No. 4492760.

[0282] Among these, the above xanthenic dye may include a compound represented by the following chemical formula 8.

[0283] [Chemical Formula 8]

[0284]

[0285] In the above formula,

[0286] R 29 to R 34 Each is independently a hydrogen atom or a carbon-1 to carbon-5 alkyl group, and

[0287] R 35 and R 36 Each independently consists of a hydrogen atom, -COOH, -COO - , -SO3 - , -SO3H, -SO3Na, -COOCH3 or -COOCH2CH3.

[0289] As used in this specification, alkyl groups having 1 to 5 carbon atoms refer to straight-chain or branched monovalent hydrocarbons composed of 1 to 5 carbon atoms, and include, but are not limited to, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, etc.

[0291] The above xanthen-based dye may be purchased and used, or synthesized directly and used. Specifically, the above xanthen-based dye may include xanthalium salt, 3-dipropylamino, 6-diethylamino, 9-(2-sulfophenyl)-, intramolecular salt (manufactured by Sumitomo Chemical), but is not limited thereto.

[0293] The above xanthen dye may be included in an amount of 30% by weight or less, for example, 1 to 30% by weight, based on 100% by weight of the total blue coloring agent. When the above xanthen dye is included within the above content range, reliability and compatibility with the solvent can be ensured.

[0295] The above coloring agent (A) may be included in an amount of 5 to 65 weight%, preferably 10 to 60 weight%, based on 100 weight% of the total solid content of the colored photosensitive resin composition. If the content of the coloring agent (A) is within the above range, the color intensity of the pixels is sufficient when forming a thin film, and there is an advantage that the omission of non-pixel parts is not reduced during development, so no residue is generated.

[0296] In the present invention, the term "solid content" in the colored photosensitive resin composition refers to the sum of the components excluding the solvent.

[0298] Alkali-soluble resin (B)

[0299] In one embodiment of the present invention, the alkali-soluble resin (B) may be selected and used without special limitations from any resin known in the art, provided that it has reactivity and alkali solubility through the action of light or heat, acts as a dispersion medium for solids, and performs the function of a binding resin.

[0300] The above alkali-soluble resin (B) may be a copolymer of an ethylenically unsaturated monomer having a carboxyl group and a monomer having other unsaturated double bonds.

[0301] Specific examples of the ethylenically unsaturated monomer having the above-mentioned 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.

[0302] Other monomers having unsaturated double bonds include 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;

[0303] Aromatic vinyl compounds such as styrene, vinyltoluene, α-methylstyrene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, o-vinylbenzylmethyl ether, m-vinylbenzylmethyl ether, p-vinylbenzylmethyl ether, o-vinylbenzylglycidyl ether, m-vinylbenzylglycidyl ether, p-vinylbenzylglycidyl ether;

[0304] N-substituted maleimide compounds such as N-cyclohexylmaleimide, N-benzylmaleimide, N-phenylmaleimide, No-hydroxyphenylmaleimide, Nm-hydroxyphenylmaleimide, Np-hydroxyphenylmaleimide, No-methylphenylmaleimide, Nm-methylphenylmaleimide, Np-methylphenylmaleimide, No-methoxyphenylmaleimide, Nm-methoxyphenylmaleimide, Np-methoxyphenylmaleimide, etc.;

[0305] Alkyl (meth)acrylate compounds such as methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, i-propyl (meth)acrylate, n-butyl (meth)acrylate, i-butyl (meth)acrylate, sec-butyl (meth)acrylate, t-butyl (meth)acrylate, etc.;

[0306] cyclophenyl(meth)acrylate compounds such as cyclopentyl(meth)acrylate, cyclohexyl(meth)acrylate, 2-methylcyclohexyl(meth)acrylate, 2-dicyclofentanyloxyethyl(meth)acrylate, isobornyl(meth)acrylate, etc.;

[0307] Aryl (meth)acrylates such as phenyl (meth)acrylate and benzyl (meth)acrylate;

[0308] Unsaturated oxetane compounds such as 3-(methacryloyloxymethyl)oxetane, 3-(methacryloyloxymethyl)-3-ethyloxetane, 3-(methacryloyloxymethyl)-2-trifluoromethyloxetane, 3-(methacryloyloxymethyl)-2-phenyloxetane, 2-(methacryloyloxymethyl)oxetane, 2-(methacryloyloxymethyl)-4-trifluoromethyloxetane;

[0309] Vinyl carboxylate ester compounds such as vinyl acetate, vinyl propionate, etc.;

[0310] Examples include vinyl cyanide compounds such as (meth)acrylonitrile and α-chloroacrylonitrile. These can be used individually or in combination of two or more.

[0312] The method for manufacturing the above copolymer is not particularly limited, and conventionally known polymerization methods may be used, and among known polymerization methods, solution polymerization is preferred. In addition, the polymerization temperature or polymerization time varies depending on the type or ratio of the monomer introduced, the molecular weight and acid value of the desired alkali-soluble resin, but, for example, polymerization can be carried out at 60 to 130°C for 1 to 10 hours.

[0314] The above alkali-soluble resin (B) may have an acid value of 20 to 200 (KOH mg / g). If the acid value is within the above range, solubility in the developer is improved, so the non-exposed area dissolves easily and sensitivity increases, and consequently, the pattern of the exposed area remains during development, which is desirable as it improves the film remaining ratio. Here, the acid value is a value measured as the amount of potassium hydroxide (mg) required to neutralize 1 g of polymer, and can typically be obtained by titrating using an aqueous potassium hydroxide solution.

[0315] The above alkali-soluble resin (B) may have a polystyrene equivalent weight-average molecular weight (hereinafter simply referred to as "weight-average molecular weight") measured by gel permeation chromatography (GPC; using tetrahydrofuran as the elution solvent) of 3,000 to 200,000, preferably 5,000 to 100,000. It is desirable that the molecular weight is within the above range, as this improves the hardness of the coating film, increases the residual film rate, and tends to improve the solubility of the non-exposed portion in the developer solution and the resolution.

[0316] 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 provides excellent developability.

[0318] The alkali-soluble resin (B) may be included in an amount of 5 to 80 weight%, preferably 10 to 70 weight%, based on 100 weight% of the total solid content of the colored photosensitive resin composition. When the alkali-soluble resin (B) is included in the above range, it is desirable because the solubility in the developer is sufficient to facilitate pattern formation, and the reduction of the film in the exposed area during development is prevented, thereby improving the omission of the non-exposed area.

[0320] Photopolymerizable compound (C)

[0321] 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 later, and may include a monofunctional photopolymerizable compound, a difunctional photopolymerizable compound, or a polyfunctional photopolymerizable compound with three or more functions.

[0322] Specific examples of the above monofunctional photopolymerizable compounds include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, and commercially available products include Aronics M-101 (Doagosei), KAYARAD TC-110S (Nippon Kayaku), or Viscote 158 (Osaka Yukigaku High School).

[0323] Specific examples of the above-mentioned difunctional 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, and commercially available products include Aronics M-210, M-1100, M-1200 (Doagosei), KAYARAD HDDA (Nippon Kayaku), Viscote 260 (Osaka Yuki Kagaku Kogyo), AH-600, AT-600, or UA-306H (Kyoeisha Kagaku Co., Ltd.).

[0324] Specific examples of the above-mentioned 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, propoxylated dipentaerythritol hexa(meth)acrylate, and others; commercially available products include NK ESTER ATM-4E (Shinnakamura) and Aronics M-309. Examples include the M-520 (Doagosei), KAYARAD TMPTA, KAYARAD DPHA, or KAYARAD DPHA-40H (Nippon Kayaku).

[0325] The photopolymerizable compounds exemplified above may be used alone or in a mixture of two or more.

[0326] The above photopolymerizable compound (C) may be included in an amount of 0.5 to 50 weight%, particularly 5 to 30 weight%, based on 100 weight% of the total solid content of the colored photosensitive resin composition. When the above photopolymerizable compound (C) is included in the above range, the strength or smoothness of the pixel portion may be improved.

[0328] Photopolymerization initiator (D)

[0329] In one embodiment of the present invention, the photopolymerization initiator (D) is a compound for initiating the polymerization of the photopolymerizable compound (C), and comprises an oxime ester compound represented by any one of the following chemical formulas 1 to 3.

[0330] [Chemical Formula 1]

[0331]

[0332] [Chemical Formula 2]

[0333]

[0334] [Chemical Formula 3]

[0335]

[0336] In the above formula,

[0337] R 1 , R 8 and R 11 C1-C each independently 20 It is an alkyl group or an aryl group, and

[0338] R 2 , R 3 , R 9 , R 10 , R 12 and R 13 C1-C each independently 20 alkyl group of, C4-C 16 cycloalkylalkyl group of, C6-C 21 arylalkyl group of, C2-C 20 The alkoxyalkyl group or C3-C 21 It is an alkoxycarbonylalkyl group of,

[0339] Y 1 to Y 3 Each independently has a direct bond, an arylene group, or a C3-C 10 It is a cycloalkylene group, and

[0340] R 4 to R 7 , R 14 and R 15 C1-C each independently 20 alkyl group of, C4-C 16 cycloalkylalkyl group of, C6-C 21 arylalkyl group of, C2-C 20 It is an alkoxyalkyl group or an aryl group.

[0342] C1-C used in this specification 20The alkyl group refers to a straight-chain or branched hydrocarbon composed 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, 2-ethylheptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, stearyl, nonadecyl, eicosanyl, etc.

[0343] As used herein, aryl groups include aromatic groups, heteroaromatic groups, and their partially reduced derivatives. The aromatic group is a simple or fused ring type with 5 to 15 members, and the heteroaromatic group refers to an aromatic group containing one or more oxygen, sulfur, or nitrogen. Representative examples of aryl groups include, but are not limited to, phenyl, naphthyl, pyridinyl, pyrimidinyl, furanyl, thiophenyl, indolyl, quinolinyl, imidazolinyl, oxazolyl, thiazolyl, tetrahydronaphthyl, and pyridinyl.

[0344] C4-C used in this specification 16 The cycloalkylalkyl group of is C3-C 10 It refers to a complex group formed by connecting a cycloalkyl group and a C1-C6 alkyl group, and includes, but is not limited to, cyclopentylmethyl group, cyclohexylmethyl group, cyclopentylethyl group, cyclohexylethyl group, cyclopentylpropyl group, cyclohexylpropyl group, etc.

[0345] C6-C used in this specification 21 The arylalkyl group is C5-C 15 It refers to a complex group formed by substituting an aryl group (aromatic hydrocarbon group) on a carbon of a C1-C6 alkyl group, and includes, but is not limited to, benzyl, phenethyl, etc.

[0346] C2-C used in this specification 20 The alkoxyalkyl group is C1-C 10 The alkoxy group and C1-C 10 It refers to a complex group formed by connecting alkyl groups, and includes, but is not limited to, examples such as methoxymethyl group, methoxyethyl group, methoxypropyl group, ethoxymethyl group, ethoxyethyl group, ethoxypropyl group, etc.

[0347] C3-C used in this specification 21 The alkoxycarbonylalkyl group of is C1-C 10 alkoxy groups, carbonyl groups, and C1-C 10 It refers to a complex group formed by connecting alkyl groups, and includes, but is not limited to, methoxycarbonylmethyl group, methoxycarbonylethyl group, methoxycarbonylpropyl group, ethoxycarbonylmethyl group, ethoxycarbonylethyl group, ethoxycarbonylpropyl group, etc.

[0348] As used herein, arylene groups include divalent aromatic groups, heteroaromatic groups, and their partially reduced derivatives. The aromatic groups are simple or fused ring types with 5 to 15 members, and heteroaromatic groups refer to aromatic groups containing one or more oxygen, sulfur, or nitrogen. Representative examples of arylene groups include, but are not limited to, phenylene, naphthylene, pyridinylene, furanylene, thiophenylene, indolylene, quinolinylene, imidazolinylene, oxazolylene, thiazolylene, and tetrahydronaphthylene.

[0349] C3-C used in this specification 10The cycloalkylene group refers to a simple or fused cyclic hydrocarbon composed of 3 to 10 carbon atoms of divalent form, and includes, but is not limited to, cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene, etc.

[0350] The above aryl group and C6-C 21 The arylalkyl group has one or more hydrogens that are C1-C6 alkyl groups, C2-C6 alkenyl groups, C2-C6 alkynyl groups, C3-C 10 cycloalkyl group of, C3-C 10 heterocycloalkyl group of, C3-C 10 It can be substituted with heterocycloalkyloxy groups, C1-C6 haloalkyl groups, C1-C6 alkoxy groups, C1-C6 thioalkoxy groups, aryl groups, acyl groups, hydroxyl, thio, halogen, amino, alkoxycarbonyl, carboxyl, carbamoyl, cyano, nitro, etc.

[0352] In one embodiment of the present invention, regarding suppression of double step difference occurrence, suppression of brightness reduction, improvement of sensitivity, and reduction of film shrinkage rate resulting therefrom

[0353] R 1 C1-C 20 It is an alkyl group or an aryl group, and

[0354] R 2 and R 3 C1-C each independently 20 alkyl group of, C4-C 16 cycloalkylalkyl group of, C6-C 21 arylalkyl group or C2-C 20 It is an alkoxyalkyl group of, and

[0355] Y 1 is a directly bonded or arylene group, and

[0356] R 4 to R 7 C1-C each independently 20 It can be an alkyl group.

[0358] In one embodiment of the present invention, R in terms of solubility, dispersibility, and brightness improvement 2 and R 3 They may not be identical to each other.

[0360] In one embodiment of the present invention, regarding suppression of double step difference occurrence, suppression of brightness reduction, improvement of sensitivity, and reduction of film shrinkage rate resulting therefrom

[0361] R 8 C1-C 20 It is an alkyl group of, and

[0362] R 9 and R 10 C1-C each independently 20 alkyl group of, C4-C 16 cycloalkylalkyl group of, C6-C 21 arylalkyl group or C2-C 20 It is an alkoxyalkyl group of, and

[0363] Y 2 It can be an arylene group.

[0365] In one embodiment of the present invention, R in terms of solubility, dispersibility, and brightness improvement 9 and R 10 They may not be identical to each other.

[0367] In one embodiment of the present invention, regarding suppression of double step difference occurrence, suppression of brightness reduction, improvement of sensitivity, and reduction of film shrinkage rate resulting therefrom

[0368] R 11 C1-C 20 It is an alkyl group of, and

[0369] R 12 and R 13 C1-C each independently 20 alkyl group of, C4-C 16 cycloalkylalkyl group of, C2-C 20 The alkoxyalkyl group or C3-C 21 It is an alkoxycarbonylalkyl group of,

[0370] Y 3 is a directly bonded or arylene group, and

[0371] R 14 and R 15 C1-C each independently 20 It can be an alkyl group.

[0373] In one embodiment of the present invention, R in terms of solubility, dispersibility, and brightness improvement 12 and R 13 They may not be identical to each other.

[0375] In one embodiment of the present invention, R in terms of suppressing double step difference occurrence, suppressing brightness reduction, improving sensitivity, and reducing film shrinkage rate resulting therefrom 1 , R 8 and R 11 Each can independently be a methyl group or a phenyl group.

[0376] In one embodiment of the present invention, R in terms of suppressing double step difference occurrence, suppressing brightness reduction, improving sensitivity, and reducing film shrinkage rate resulting therefrom 2 , R 3 , R 9 , R 10 , R 12 and R 13 C1-C each independently 10 It may be an alkyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, a benzyl group, a methoxymethyl group, or an ethoxycarbonylmethyl group.

[0377] In one embodiment of the present invention, Y in terms of suppressing double step difference occurrence, suppressing brightness reduction, improving sensitivity, and reducing film shrinkage rate resulting therefrom 1 to Y 3 Each can independently be a directly bonded phenylene group or a naphthylene group.

[0378] In particular, Y 1 to Y 3 In the case of direct bonding, the minimum exposure amount is low, exhibiting high sensitivity, and not only can the solvent resistance of the coating film be improved, but the transmittance in the visible light region is also improved when forming a color coating film, which can increase brightness.

[0380] In one embodiment of the present invention, regarding suppression of double step difference occurrence, suppression of brightness reduction, improvement of sensitivity, and reduction of film shrinkage rate resulting therefrom

[0381] R 1 , R 8 and R 11 Each is independently a methyl group or a phenyl group, and

[0382] R 2 , R 3 , R 9 , R 10 , R 12 and R 13 C1-C each independently 10 It is an alkyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, a benzyl group, a methoxymethyl group, or an ethoxycarbonylmethyl group, and

[0383] Y 1 to Y 3 Each is independently a directly bonded phenylene group or a naphthylene group, and

[0384] R 4 to R 7 , R 14 and R 15 C1-C each independently 10 It can be an alkyl group.

[0386] Specifically, the oxime ester compound according to one embodiment of the present invention may be selected from compounds represented by the following chemical formulas 1-1 to 1-18, 2-1 to 2-17 and 3-1 to 3-17.

[0387] [Chemical Formula 1-1]

[0388]

[0389] [Chemical Formula 1-2]

[0390]

[0391] [Chemical Formula 1-3]

[0392]

[0393] [Chemical Formula 1-4]

[0394]

[0395] [Chemical Formula 1-5]

[0396]

[0397] [Chemical Formula 1-6]

[0398]

[0399] [Chemical Formula 1-7]

[0400]

[0401] [Chemical Formula 1-8]

[0402]

[0403] [Chemical Formula 1-9]

[0404]

[0405] [Chemical Formula 1-10]

[0406]

[0407] [Chemical Formula 1-11]

[0408]

[0409] [Chemical Formula 1-12]

[0410]

[0411] [Chemical Formula 1-13]

[0412]

[0413] [Chemical Formula 1-14]

[0414]

[0415] [Chemical Formula 1-15]

[0416]

[0417] [Chemical Formula 1-16]

[0418]

[0419] [Chemical Formula 1-17]

[0420]

[0421] [Chemical Formula 1-18]

[0422]

[0423] [Chemical Formula 2-1]

[0424]

[0425] [Chemical Formula 2-2]

[0426]

[0427] [Chemical Formula 2-3]

[0428]

[0429] [Chemical Formula 2-4]

[0430]

[0431] [Chemical Formula 2-5]

[0432]

[0433] [Chemical Formula 2-6]

[0434]

[0435] [Chemical Formula 2-7]

[0436]

[0437] [Chemical Formula 2-8]

[0438]

[0439] [Chemical Formula 2-9]

[0440]

[0441] [Chemical Formula 2-10]

[0442]

[0443] [Chemical Formula 2-11]

[0444]

[0445] [Chemical Formula 2-12]

[0446]

[0447] [Chemical Formula 2-13]

[0448]

[0449] [Chemical Formula 2-14]

[0450]

[0451] [Chemical Formula 2-15]

[0452]

[0453] [Chemical Formula 2-16]

[0454]

[0455] [Chemical Formula 2-17]

[0456]

[0457] [Chemical Formula 3-1]

[0458]

[0459] [Chemical Formula 3-2]

[0460]

[0461] [Chemical Formula 3-3]

[0462]

[0463] [Chemical Formula 3-4]

[0464]

[0465] [Chemical Formula 3-5]

[0466]

[0467] [Chemical Formula 3-6]

[0468]

[0469] [Chemical Formula 3-7]

[0470]

[0471] [Chemical Formula 3-8]

[0472]

[0473] [Chemical Formula 3-9]

[0474]

[0475] [Chemical Formula 3-10]

[0476]

[0477] [Chemical Formula 3-11]

[0478]

[0479] [Chemical Formula 3-12]

[0480]

[0481] [Chemical Formula 3-13]

[0482]

[0483] [Chemical Formula 3-14]

[0484]

[0485] [Chemical Formula 3-15]

[0486]

[0487] [Chemical Formula 3-16]

[0488]

[0489] [Chemical Formula 3-17]

[0490]

[0492] An oxime ester compound represented by any one of the above chemical formulas 1 to 3 can be prepared by a method known in the art.

[0493] Specifically, a fluorene, diphenylsulfane, or carbazole compound can be prepared by reacting it with an acyl chloride compound via Friedel-Crafts acylation to obtain an intermediate compound of a fluorene, diphenylsulfane, or carbazole backbone with an acyl group substituted therein, then reacting 2 equivalents of the intermediate compound with 1 equivalent of a diacyl chloride compound via Friedel-Crafts acylation, then reacting it with isobutyl nitrite under an acid catalyst to introduce an oxime group, and then acylating the oxime group in the presence of a base.

[0494] The above Friedel-Crafts acylation reaction can be carried out using a metal catalyst, for example, aluminum chloride.

[0495] Hydrochloric acid, etc., can be used as the acid catalyst when introducing the above oxime group.

[0496] Triethylamine (TEA), etc., can be used as the base in the above acylation reaction.

[0497] For example, an oxime ester compound represented by any one of the above chemical formulas 1 to 3 can be prepared by the method described in the synthesis example below.

[0499] An oxime ester compound represented by any one of the above chemical formulas 1 to 3 has a structure in which two aromatic polycyclic functional groups and oxime ester functional groups are bonded to both sides via a carbonyl group.

[0500] Specifically, the oxime ester compound represented by Chemical Formula 1 has a structure in which two fluorene groups and oxime ester functional groups are bonded to both sides via a carbonyl group, the oxime ester compound represented by Chemical Formula 2 has a structure in which two bisphenyl sulfide groups and oxime ester functional groups are bonded to both sides via a carbonyl group, and the oxime ester compound represented by Chemical Formula 3 has a structure in which two carbazole groups and oxime ester functional groups are bonded to both sides via a carbonyl group.

[0501] Accordingly, the oxime ester compound represented by any one of the above chemical formulas 1 to 3 has a high molar extinction coefficient and excellent sensitivity, so it can be used as a high-sensitivity photopolymerization initiator that provides excellent curing with a small amount of exposure even when added in small quantities. In addition, the oxime ester compound represented by any one of the above chemical formulas 1 to 3 can be applied to a colored photosensitive resin composition to improve brightness during pattern formation and improve the solvent resistance of the cured film. Furthermore, the above oxime ester compound can suppress film shrinkage while preventing light leakage caused by differences in film thickness due to double step differences occurring at the edge portions of the formed pattern.

[0503] In particular, the oxime ester compound represented by Chemical Formula 3 is R 12 and R 13 When these are not identical, that is, when they have an asymmetric structure in which two functional groups of different structures are bonded to each other via a carbonyl group, the solubility for solvents commonly used in the art, such as propylene glycol methyl ether acetate (PGMEA), can be increased, and crystallinity and self-aggregation can be lowered to increase dispersibility within the composition after dissolution and suppress the decrease in transmittance due to aggregation, thereby further improving brightness.

[0504] In addition, in the case of oxime ester compounds represented by Chemical Formula 1 or 2, R 2 and R 3 , and R 9 and R 10 When these are not identical, that is, when they have an asymmetric structure in which two functional groups of different structures are bonded to each other via a carbonyl group, the solubility in solvents commonly used in the art, such as propylene glycol methyl ether acetate (PGMEA), may be increased and the brightness may be further improved.

[0506] An oxime ester compound represented by any one of the above chemical formulas 1 to 3 may be included in an amount of 5% or more by weight, preferably 10% or more by weight, 20% or more by weight, 30% or more by weight, 40% or more by weight, 50% or more by weight, for example, 5 to 100% by weight, based on 100% by weight of the total photopolymerization initiator. If an oxime ester compound represented by any one of the above chemical formulas 1 to 3 is included in an amount less than the above range based on 100% by weight of the total photopolymerization initiator, it may be difficult to achieve high sensitivity.

[0507] In one embodiment of the present invention, the photopolymerization initiator may additionally include one or more compounds selected from the group consisting of acetophenone-based compounds, benzophenone-based compounds, triazine-based compounds, nonimidazole-based compounds, oxime-based compounds, and thioxanthone-based compounds, in addition to the oxime ester compound represented by any one of the formulas 1 to 3, with respect to polymerization characteristics, initiation efficiency, absorption wavelength, availability, price, etc.

[0508] Specific examples of the above acetophenone-based compounds include diethoxyacetophenone, 2-hydroxy-2-methyl-1-phenylpropan-1-one, benzyldimethylketal, 2-hydroxy-1-[4-(2-hydroxyethoxy)phenyl]-2-methylpropan-1-one, 1-hydroxycyclohexylphenylketone, 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, 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4-morpholinophenyl)butan-1-one, etc.

[0509] Examples of the above benzophenone compounds include benzophenone, 0-methyl benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenylsulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, 2,4,6-trimethylbenzophenone, etc.

[0510] Specific examples of the above-mentioned nonimidazole compounds 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 nonimidazole compounds in which the phenyl group at the 4,4',5,5' position is substituted by 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 preferably used.

[0511] Specific examples of the above 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, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine. Examples include 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine.

[0512] The above oxime-based compounds include 1,2-octanedione, 1-[4-(phenylthio)phenyl]-,2-(O-benzoyloxime), ethanol 1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-1-(O-acetyloxime), 1-[4-(phenylthio)phenyl]-3-cyclopentylpropane-1,2-dione-2-(O-benzoyloxime), 1-[4-(phenylthio)phenyl]-3-cyclohexylpropane-1,2-dione-2-(O-acetyloxime), and commercially available products include TR-PBG-305 (TRONLY), OXE-01 (BASF), and OXE-02 (BASF).

[0513] Examples of the above thioxantone compounds include 2-isopropylthioxantone, 2,4-diethylthioxantone, 2,4-dichlorothioxantone, 1-chloro-4-propoxythioxantone, etc.

[0515] In addition, the photopolymerization initiator (D) may be used in combination with a photopolymerization initiation aid (D-1) to improve the sensitivity of the colored photosensitive resin composition of the present invention. By containing the photopolymerization initiation aid, the colored photosensitive resin composition according to the present invention can have its sensitivity further increased, thereby improving productivity.

[0516] The above photopolymerization initiation aid may preferably be one or more compounds selected from the group consisting of, for example, amine compounds, carboxylic acid compounds, and organic sulfur compounds having thiol groups.

[0517] Specifically, the above amine compounds may include aliphatic amine compounds such as triethanolamine, methyldiethanolamine, and triisopropanolamine; aromatic amine compounds such as 4-dimethylaminobenzoate, 4-dimethylaminobenzoate ethyl, 4-dimethylaminobenzoate isoamyl, 4-dimethylaminobenzoate 2-ethylhexyl, 2-dimethylaminoethyl benzoate, N,N-dimethylparatoluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Mihiler ketone), and 4,4'-bis(diethylamino)benzophenone, and it is particularly preferable to use aromatic amine compounds.

[0518] The above carboxylic acid compound is preferably an aromatic heteroacetic acid, and specifically, examples 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, naphthoxyacetic acid, etc.

[0519] Specific examples of organic sulfur compounds having the above-mentioned 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 tetraethyleneglycolbis(3-mercaptopropionate).

[0521] The above photopolymerization initiator (D) may be included in an amount of 0.01 to 10 weight%, preferably 1 to 7 weight%, based on 100 weight% of the total solid content of the colored photosensitive resin composition. When the above photopolymerization initiator (D) is included in the above range, it is desirable because the colored photosensitive resin composition of the present invention becomes highly sensitive, thereby shortening the exposure time and improving productivity. In addition, the strength of the coating film formed using the composition under the above conditions and the smoothness on the surface of the coating film may be improved.

[0522] In addition, when the above photopolymerization initiation aid (D-1) is further used, it is preferable to use the above photopolymerization initiation aid (D-1) in an amount typically 10 moles or less per mole of photopolymerization initiator, preferably in the range of 0.01 to 5 moles. When the above photopolymerization initiation aid (D-1) is included in the above range, the sensitivity of the colored photosensitive resin composition can be increased and productivity can be improved.

[0524] Solvent (E)

[0525] In one embodiment of the present invention, the solvent (E) can be used without special limitation as long as it is effective in dissolving other components included in the colored photosensitive resin composition, and solvents used in conventional colored photosensitive resin compositions are particularly preferred, such as ethers, aromatic hydrocarbons, ketones, alcohols, esters, or amides.

[0526] The above solvent (E) specifically includes 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; Alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, and glycerin; Examples include esters such as 3-ethyl ethoxypropionate, 3-methyl 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. The above solvents can each be used individually or in a mixture of two or more types.

[0527] The solvent (E) may be included in an amount of 30 to 95 weight%, preferably 40 to 90 weight%, based on 100 weight% of the total color-sensitive resin composition. When the solvent (E) is included in the above range, the coating performance may be improved when applied using a coating device such as a roll coater, spin coater, slit-and-spin coater, slit coater (sometimes called a die coater), or inkjet.

[0529] Additives (F)

[0530] In addition to the above components, the colored photosensitive resin composition according to one embodiment of the present invention may also use additives (F), such as fillers, other polymer compounds, curing agents, surfactants, adhesion promoters, ultraviolet absorbers, and anti-aggregation agents, as needed by those skilled in the art, within a range that does not impair the purpose of the present invention.

[0531] Specifically, the above-mentioned filler may be glass, silica, alumina, etc., but is not limited thereto.

[0532] The above-mentioned other polymer compounds may specifically include thermosetting resins such as epoxy resin and maleimide resin, and thermoplastic resins such as polyvinyl alcohol, polyacrylic acid, polyethylene glycol monoalkyl ether, polyfluoroalkyl acrylate, polyester, and polyurethane, but are not limited thereto.

[0533] The above-mentioned curing agent is used to increase deep curing and mechanical strength, and specifically, epoxy compounds, polyfunctional isocyanate compounds, melamine compounds, oxetane compounds, etc. may be used, but is not limited thereto. Specifically, the above-mentioned epoxy compounds may include bisphenol A-based epoxy resin, hydrogenated bisphenol A-based epoxy resin, bisphenol F-based epoxy resin, hydrogenated bisphenol F-based epoxy resin, novolak-type epoxy resin, other aromatic epoxy resins, alicyclic epoxy resins, glycidyl ester-based resins, glycidylamine-based 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 epoxides, isoprene (co)polymer epoxides, glycidyl (meth)acrylate (co)polymers, triglycidyl isocyanurate, etc., but are not limited thereto. Specifically, the above oxetane compounds may include carbonate bis-oxetane, xylene bis-oxetane, adipate bis-oxetane, terephthalate bis-oxetane, cyclohexane dicarboxylic acid bis-oxetane, etc., but are not limited thereto.

[0534] The above-mentioned curing agent may be used in combination with a curing aid compound capable of causing ring-opening polymerization of the epoxy groups of the epoxy compound and the oxetane backbone of the oxetane compound. Specifically, the above-mentioned curing aid compound may be polycarboxylic acids, polycarboxylic anhydrides, acid generators, etc. The above-mentioned polycarboxylic anhydrides may be commercially available as epoxy resin curing agents. Examples of the above-mentioned commercially available epoxy resin curing agents include the product name (Adeka Hadona EH-700) (manufactured by Adeka Industries, Ltd.), the product name (Ricasitdo HH) (manufactured by Shin Nippon Iwa Co., Ltd.), and the product name (MH-700) (manufactured by Shin Nippon Iwa Co., Ltd.).

[0535] The curing agents and curing aid compounds exemplified above can each be used individually or in a mixture of two or more types.

[0536] The above surfactant can be used to further improve the film-forming ability of the colored photosensitive resin composition of the present invention, and fluorine-based surfactants, silicone-based surfactants, etc. may be preferably used.

[0537] Examples of the above silicone-based surfactants include commercially available products such as DC3PA, DC7PA, SH11PA, SH21PA, SH8400 from Dow Corning Toray Silicon, and TSF-4440, TSF-4300, TSF-4445, TSF-4446, TSF-4460, TSF-4452 from GE Toshiba Silicon. Examples of the above fluorine-based surfactants include commercially available products such as MegaPac F-470, F-471, F-475, F-482, F-489, F-554 from Dainippon Ink & Chemical Co., Ltd.

[0538] The surfactants exemplified above can each be used individually or in combination of two or more types.

[0539] Specifically, the above adhesion promoter may be used alone or a mixture thereof selected from the group consisting of vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris(2-methoxyethoxy)silane, N-(2-aminoethyl)-3-aminopropylmethyldimethoxysilane, N-(2-aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanatepropyltrimethoxysilane, and 3-isocyanatepropyltriethoxysilane.

[0540] The above adhesion promoter may be included in an amount of 0.01 to 10 weight%, preferably 0.05 to 2 weight%, based on 100 weight% of the total solid content in the colored photosensitive resin composition.

[0541] Specifically, the above-mentioned ultraviolet absorber may include 2-(3-tert-butyl-2-hydroxy-5-methylphenyl)-5-chlorobenzotriazole, alkoxybenzophenone, etc., but is not limited thereto.

[0542] The above anti-coagulant may specifically use sodium polyacrylate, but is not limited thereto.

[0543] The above additive (F) may be included in an amount of 0.01 to 15 weight%, preferably 0.05 to 5 weight%, based on 100 weight% of the total solid content in the colored photosensitive resin composition.

[0545] A colored photosensitive resin composition according to one embodiment of the present invention can be prepared by, for example, the following method.

[0546] First, the pigment among the above-mentioned coloring agents is mixed with a solvent and dispersed using a bead mill or the like until the average particle size of the pigment is approximately 0.2 μm or less. At this time, if necessary, a pigment dispersant, part or all of the alkali-soluble resin, and a dye may be mixed with the solvent to dissolve or disperse them. The remainder of the alkali-soluble resin, a photopolymerization initiator, a photopolymerizable compound, and additives, and if necessary, a solvent may be further added to the mixed dispersion to achieve a predetermined concentration to produce a colored photosensitive resin composition according to the present invention.

[0548] The colored photosensitive resin composition according to the present invention can be used to manufacture a colored pattern, and the colored pattern can be used, for example, as described below, in a color filter, specifically in a color filter of an image display device or a solid-state imaging element.

[0549] Accordingly, one embodiment of the present invention relates to a colored pattern and a color filter formed using the colored photosensitive resin composition described above. A color filter according to one embodiment of the present invention is characterized by including a colored pattern formed by applying the colored photosensitive resin composition described above onto a substrate and exposing and developing it in a predetermined pattern.

[0551] Hereinafter, a method for forming a pattern using the colored photosensitive resin composition of the present invention will be described in detail.

[0552] A method for forming a pattern using the colored photosensitive resin composition of the present invention may use methods known in the art, but typically includes a coating step; an exposure step; and a removal step. By applying the colored photosensitive resin composition of the present invention onto a substrate and forming a pattern through photocuring and development, it becomes possible to use it as a colored pixel (colored image).

[0553] Specifically, the above-described colored photosensitive resin composition is applied onto a substrate using a suitable method such as spin coating or slit coating. After application, light is irradiated to form a pattern required for a color filter. As a light source, g-lines (wavelength: 436 nm), h-lines, i-lines (wavelength: 365 nm), KrF-lines (wavelength: 248 nm), etc., may be used. The exposure amount can be appropriately selected as needed, for example, 20 to 2,000 mJ / cm². After irradiating with light, the coating layer is treated with an alkaline developer, causing the unirradiated portions of the coating layer to dissolve and the pattern required for the color filter to be formed. By repeating this process according to the required number of R, G, and B colors, a color filter having a desired pattern can be obtained. Furthermore, in the above process, crack resistance, solvent resistance, etc., can be further improved by reheating the image pattern obtained by development or by curing it through active light irradiation.

[0554] When the above color filter is applied to an image display device, the substrate may be a glass substrate with nothing coated on it or a glass substrate coated with SiNx (protective film) to a thickness of 500 to 1,500 Å.

[0555] When the above color filter is applied to a solid-state image sensor, the substrate may include a photoelectric conversion device substrate used in the solid-state image sensor (e.g., a silicon substrate for a CCD or CMOS). The substrate may also include a black matrix or a black stripe for isolating each pixel.

[0557] One embodiment of the present invention relates to an image display device equipped with the color filter described above.

[0558] The color filter of the present invention can be applied not only to conventional liquid crystal displays (LCDs) but also to various image display devices such as electroluminescent displays (EL), plasma display devices (PDPs), field emission displays (FEDs), and organic light-emitting diodes (OLEDs).

[0559] The image display device of the present invention includes a configuration known in the art, except for having the color filter described above.

[0560] An image display device according to one embodiment of the present invention may additionally comprise a color filter including 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 preferably, a light source emitting blue light may be used for better color reproduction.

[0561] An image display device according to one embodiment of the present invention may additionally comprise a color filter comprising only two color pattern layers among a red pattern layer, a green pattern layer, and a blue pattern layer, in addition to the color filter described above. In such a case, the color filter further comprises a transparent pattern layer that does not contain quantum dot particles. When only two color pattern layers are provided, a light source emitting light of a wavelength representing the remaining color not included may be used. For example, when only a red pattern layer and a green pattern layer are provided, a light source emitting 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 transmits the blue light as is to display blue.

[0563] One embodiment of the present invention relates to a solid-state imaging element equipped with the color filter described above.

[0564] The above solid-state imaging element may include, for example, a CMOS image sensor.

[0565] The above-described solid-state imaging element includes a support comprising a semiconductor element or a photoelectric conversion element and a microlens, and the color filter may be disposed between the support and the microlens.

[0567] The present invention will be explained more specifically below through examples, comparative examples, and experimental examples. These examples, comparative examples, and experimental examples are intended solely to illustrate the present invention, and it is obvious to those skilled in the art that the scope of the present invention is not limited thereto.

[0569] Preparation Example 1: Preparation of pigment dispersion (A-1)

[0570] 13 parts by weight of CI Pigment Red 254 as a pigment, 4 parts by weight of BYKLPN-6919 (BYK) as a pigment dispersant, and 83 parts by weight of propylene glycol monomethyl ether acetate as a solvent were mixed and mixed and dispersed using a bead mill to prepare a pigment dispersion.

[0572] Preparation Example 2: Preparation of pigment dispersion (A-2)

[0573] 17 parts by weight of CI Pigment Red 177 as a pigment, 4 parts by weight of BYKLPN-6919 (BYK) as a pigment dispersant, and 79 parts by weight of propylene glycol monomethyl ether acetate as a solvent were mixed and mixed and dispersed using a bead mill to prepare a pigment dispersion.

[0575] Preparation Example 3: Preparation of pigment dispersion (A-3)

[0576] 15 parts by weight of CI Pigment Green 58 as a pigment, 5 parts by weight of BYKLPN-6919 (BYK) as a pigment dispersant, and 80 parts by weight of propylene glycol monomethyl ether acetate as a solvent were mixed and mixed and dispersed using a bead mill to prepare a pigment dispersion.

[0578] Preparation Example 4: Preparation of pigment dispersion (A-4)

[0579] 13 parts by weight of CI Pigment Green 59 as a pigment, 4 parts by weight of BYKLPN-6919 (BYK) as a pigment dispersant, and 83 parts by weight of propylene glycol monomethyl ether acetate as a solvent were mixed and mixed and dispersed using a bead mill to prepare a pigment dispersion.

[0581] Preparation Example 5: Preparation of pigment dispersion (A-5)

[0582] 12 parts by weight of CI Pigment Yellow 138 as a pigment, 4 parts by weight of BYKLPN-6919 (BYK) as a pigment dispersant, and 84 parts by weight of propylene glycol monomethyl ether acetate as a solvent were mixed and mixed and dispersed using a bead mill to prepare a pigment dispersion.

[0584] Preparation Example 6: Preparation of pigment dispersion (A-6)

[0585] 15 parts by weight of CI Pigment Blue 15:6 as a pigment, 4 parts by weight of BYKLPN-6919 (BYK) as a pigment dispersant, and 81 parts by weight of propylene glycol monomethyl ether acetate as a solvent were mixed and mixed and dispersed using a bead mill to prepare a pigment dispersion.

[0587] Preparation Example 7: Preparation of a triphenylmethane-based blue dye dispersion (A-7)

[0588] A triphenylmethane-based blue dye dispersion was obtained by mixing 10 parts by weight of a compound represented by the following chemical formula 7-1, 5 parts by weight of a dispersant (BYKLPN-6919, BYK) (calculated based on solid content), 82 parts by weight of propylene glycol monomethyl ether acetate, and 3 parts by weight of diacetone alcohol, adding 300 parts by weight of 0.2 mm zirconia beads, and mixing and dispersing.

[0589] [Chemical Formula 7-1]

[0590]

[0592] Preparation Example 8: Preparation of xanthenic dye dispersion (A-8)

[0593] 6 parts by weight of xantylium salt, 3-dipropylamino, 6-diethylamino, 9-(2-sulfophenyl)-, intramolecular salt (manufactured by Sumitomo Chemical) as a xanthene dye represented by chemical formula 8, 5 parts by weight of a dispersant (BYKLPN-6919, BYK Co.) (calculated based on solid content), 86 parts by weight of propylene glycol monomethyl ether acetate, and 3 parts by weight of diacetone alcohol were mixed, and 300 parts by weight of 0.2 mm zirconia beads were added and mixed and dispersed to obtain a xanthene-based dye dispersion.

[0595] Synthesis Example 1: Synthesis of the compound of Chemical Formula 1-5

[0596] Synthesis Example 1-1: Synthesis of the compound of Chemical Formula 4-1

[0597] [Chemical Formula 4-1]

[0598]

[0599] Aluminum chloride (9.5 g, 71.8 mmol) and 100 g of dichloroethane were added to a reaction vessel, and under ice cooling, dipropylfluorene (23.0 g, 61.0 mmol) and octanoyl chloride (11.5 g, 71.0 mmol) were added in that order. After reacting at room temperature for 1 hour, the reaction mixture was poured into an ice bath. After oil-water separation, the organic layer was washed three times with water, and silica gel column purification was performed to obtain the compound of Chemical Formula 4-1 as an intermediate.

[0601] Synthesis Example 1-2: Synthesis of the compound of Chemical Formula 5-1

[0602] [Chemical Formula 5-1]

[0603]

[0604] Aluminum chloride (18.7 g, 139.52 mmol) and 100 g of dichloroethane were added to a reaction vessel. Under ice cooling, the compound of Formula 4-1 (16.4 g, 43.6 mmol) and terephthaloyl chloride (4.3 g, 21.2 mmol) were added in that order. After reacting at room temperature for 1 hour, the reaction mixture was poured into an ice bath. After oil-water separation, the organic layer was washed three times with water, and silica gel column purification was performed to obtain the compound of Formula 5-1 as an intermediate.

[0606] Synthesis Example 1-3: Synthesis of the compound of Formula 6-1

[0607] [Chemical Formula 6-1]

[0608]

[0609] Compound of Formula 5-1 (15.5g, 17.6mol) and DMF (40.0g) were added to a reaction vessel, and 2.7g of 35% hydrochloric acid and isobutyl nitrite (10.8g, 104.4mol) were added in sequence while stirring at 5°C, and the reaction was carried out at room temperature for 12 hours. Ethyl acetate was added, and after oil-water separation, the organic layer was washed three times with water and purified by a silica gel column to obtain the compound of Formula 6-1 as an intermediate.

[0611] Synthesis Example 1-4: Synthesis of the compound of Chemical Formula 1-5

[0612] [Chemical Formula 1-5]

[0613]

[0614] Compound of Formula 6-1 (13.7 g, 14.6 mmol) and 50.0 g of ethyl acetate were added to a reaction vessel, and under ice cooling, acetyl chloride (2.32 g, 29.6 mmol) and triethylamine (2.99 g, 29.6 mmol) were added dropwise. After stirring at room temperature for 1 hour, ion-exchanged water was added, and oil-water separation was performed. The organic layer was washed with water three times, and after desolvation, purification was performed using a silica gel column to obtain the compound of Formula 1-5 (10.9 g, yield 72.5%).

[0615] The obtained compound is dissolved in dichloroform, and 1 H-NMR measurements were performed. The results are shown below.

[0616] 1 H-NMR: 8.30(s, 2H), 8.28(d, 2H), 8.19(s, 2H), 8.13(d, 2H), 8.00(s, 4H), 7.89(d, 2H), 7.83(d, 2H), 2.87-2.83(m, 4H), 2.28(s, 6H), 1.85-1.78(m, 8H), 1.74-1.25(m, 24H), 0.87-0.83(m, 18H)

[0618] Synthesis Example 2: Synthesis of the compound of Chemical Formula 1-7

[0619] Synthesis Example 2-1: Synthesis of the compound of Chemical Formula 4-2

[0620] [Chemical Formula 4-2]

[0621]

[0622] A compound of Formula 4-2 was obtained by carrying out the same procedure as Synthesis Example 1-1, except that cyclohexylpropanoyl chloride was used instead of octanoyl chloride in Synthesis Example 1-1.

[0624] Synthesis Example 2-2: Synthesis of the compound of Chemical Formula 1-7

[0625] [Chemical Formula 1-7]

[0626]

[0627] A compound of Formula 1-7 was obtained by carrying out the same procedure as in Synthesis Example 1, except that the compound of Formula 4-2 was used instead of the compound of Formula 4-1 in Synthesis Example 1-2 (11.0g, yield 71.8%).

[0628] 1 H-NMR: 8.30(s, 2H), 8.28(d, 2H), 8.19(s, 2H), 8.13(d, 2H), 8.00(s, 4H), 7.89(d, 2H), 7.83(d, 2H), 2.87-2.83(m, 4H), 2.28(s, 6H), 1.85-1.78(m, 8H), 1.73-1.46(m, 30H), 0.87-0.83(m, 12H)

[0630] Synthesis Example 3: Synthesis of the compound of Chemical Formula 2-4

[0631] Synthesis Example 3-1: Synthesis of the compound of Chemical Formula 4-3

[0632] [Chemical Formula 4-3]

[0633]

[0634] A compound of Formula 4-3 was obtained by carrying out the same procedure as Synthesis Example 1-1, except that diphenyl sulfide was used instead of dipropylfluorene in Synthesis Example 1-1.

[0636] Synthesis Example 3-2: Synthesis of the compound of Chemical Formula 2-4

[0637] [Chemical Formula 2-4]

[0638]

[0639] A compound of Formula 2-4 was obtained by carrying out the same procedure as in Synthesis Example 1, except that the compound of Formula 4-3 was used instead of the compound of Formula 4-1 in Synthesis Example 1-2 (9.01g, yield 68.8%).

[0640] 1H-NMR: 8.00(s, 4H), 7.86(d, 4H), 7.80(d, 4H), 7.75(d, 4H), 7.67(d, 4H), 2.85(m, 4H), 2.28(s, 6H), 1.53-1.26(m, 16H), 0.87-0.83(m, 6H)

[0642] Synthesis Example 4: Synthesis of the compound of Chemical Formula 3-1

[0643] Synthesis Example 4-1: Synthesis of the compound of Chemical Formula 4-4

[0644] [Chemical Formula 4-4]

[0645]

[0646] A compound of Formula 4-4 was obtained by carrying out the same procedure as Synthesis Example 1-1, except that ethylcarbazole was used instead of dipropylfluorene in Synthesis Example 1-1.

[0648] Synthesis Example 4-2: Synthesis of the compound of Chemical Formula 4-5

[0649] [Chemical Formula 4-5]

[0650]

[0651] A compound of Formula 4-5 was obtained by carrying out the same procedure as Synthesis Example 1-1, except that cyclohexylpropanoyl chloride and ethylcarbazole were used instead of octanoyl chloride and dipropylfluorene of Synthesis Example 1-1.

[0653] Synthesis Example 4-3: Synthesis of the compound of Chemical Formula 3-1

[0654] [Chemical Formula 3-1]

[0655]

[0656] A compound of Formula 3-1 was obtained by carrying out the same procedure as in Synthesis Example 1, except that a mixture of the compound of Formula 4-4 and the compound of Formula 4-5 in a 1:1 molar ratio was used instead of the compound of Formula 4-1 in Synthesis Example 1-2 (9.5g, yield 70.1%).

[0657] 1H-NMR: 8.92(s, 2H), 8.74(s, 2H), 8.31(d, 2H), 8.14(d, 2H), 8.00(s, 4H), 7.55(d, 2H), 7.51(d, 2H), 4.47(m, 4H), 2.85-2.50(m, 4H), 2.28(s, 6H), 1.79-1.49(m, 17H), 1.43-1.24(m, 8H), 0.86(m, 3H)

[0659] Synthesis Example 5: Synthesis of the compound of Chemical Formula 3-3

[0660] [Chemical Formula 3-3]

[0661]

[0662] A compound of Formula 3-3 was obtained by carrying out the same procedure as in Synthesis Example 1, except that instead of the compound of Formula 4-1 of Synthesis Example 1-2, a mixture of the compound of Formula 4-4 and the compound of Formula 4-5 was used in a 1:1 molar ratio, and oxalyl chloride was used instead of terephthaloyl chloride (8.51 g, yield 68.5%).

[0663] 1 H-NMR: 8.86-8.83(m, 4H), 8.30(d, 2H), 8.26(d, 2H), 7.54(d, 2H), 7.49(d, 2H), 4.44(m, 4H), 2.86-2.82(m, 4H), 2.26(s, 6H), 1.79-1.49(m, 17H), 1.43-1.24(m, 8H), 0.86(m, 3H)

[0665] Synthesis Example 6: Synthesis of the compound of Chemical Formula 3-13

[0666] [Chemical Formula 3-13]

[0667]

[0668] A compound of Formula 3-13 was obtained by carrying out the same procedure as in Synthesis Example 1, except that the compound of Formula 4-4 was used instead of the compound of Formula 4-1 in Synthesis Example 1-2, and oxalyl chloride was used instead of terephthaloyl chloride (4.74 g, yield 38.7%).

[0669] 1 H-NMR: 8.85-8.83(m, 4H), 8.30(d, 2H), 8.26(d, 2H), 7.54(d, 2H), 7.49(d, 2H), 4.44(m, 4H), 2.86-2.82(m, 4H), 2.26(s, 6H), 1.64-1.57(m, 6H), 1.49-1.26(m, 16H), 0.85(m, 6H)

[0671] Synthesis Example 7: Synthesis of the compound of Chemical Formula 1-12

[0672] [Chemical Formula 1-12]

[0673]

[0674] A compound of Formula 1-12 was obtained by carrying out the same procedure as in Synthesis Example 1, except that instead of using only the compound of Formula 4-1 of Synthesis Example 1-2, the compounds of Formula 4-1 and Formula 4-2 were used in a 1:1 molar ratio (9.7g, yield 64.1%).

[0675] 1H-NMR: 8.30(s, 2H), 8.28(d, 2H), 8.19(s, 2H), 8.13(d, 2H), 8.00(s, 4H), 7.89(d, 2H), 7.83(d, 2H), 2.87-2.83(m, 4H), 2.28(s, 6H), 1.85-1.78(m, 8H), 1.74-1.25(m, 27H), 0.87-0.83(m, 15H)

[0677] Synthesis Example 8: Synthesis of the compound of Chemical Formula 1-17

[0678] [Chemical Formula 1-17]

[0679]

[0680] A compound of Formula 1-17 was obtained by carrying out the same procedure as in Synthesis Example 1, except that instead of using only the compound of Formula 4-1 of Synthesis Example 1-2, the compounds of Formula 4-1 and Formula 4-2 were used in a 1:1 molar ratio, and oxalyl chloride was used instead of terephthaloyl chloride (7.29 g, yield 52.1%).

[0681] 1H-NMR: 8.25(d, 2H), 8.23(s, 2H), 8.13-8.10 (m, 4H), 7.84(d, 2H), 7.80(d, 2H), 2.87-2.83(m, 4H), 2.28(s, 6H), 1.85-1.78(m, 8H), 1.74-1.25(m, 27H), 0.87-0.83(m, 15H)

[0683] Synthesis Example 9: Synthesis of the compound of Chemical Formula 2-11

[0684] Synthesis Example 9-1: Synthesis of the compound of Chemical Formula 4-6

[0685] [Chemical Formula 4-6]

[0686]

[0687] A compound of Formula 4-6 was obtained by carrying out the same procedure as in Synthesis Example 1-1, except that cyclohexylpropanoyl chloride and diphenyl sulfide were used instead of octanoyl chloride and dipropylfluorene of Synthesis Example 1-1.

[0689] Synthesis Example 9-2: Synthesis of the compound of Chemical Formula 2-11

[0690] [Chemical Formula 2-11]

[0691]

[0692] A compound of Formula 2-11 was obtained by carrying out the same procedure as in Synthesis Example 1, except that compounds of Formula 4-3 and Formula 4-6 were used in a 1:1 molar ratio instead of the compound of Formula 4-1 in Synthesis Example 1-2 (7.99g, yield 60.2%).

[0693] 1 H-NMR: 8.00(s, 4H), 7.86(d, 4H), 7.80(d, 4H), 7.75(d, 4H), 7.67(d, 4H), 2.85(m, 4H), 2.28(s, 6H), 1.55-1.23(m, 19H), 0.86(m, 3H)

[0695] Synthesis Example 10: Synthesis of the compound of Chemical Formula 2-17

[0696] [Chemical Formula 2-17]

[0697]

[0698] A compound of Formula 2-17 was obtained by carrying out the same procedure as in Synthesis Example 1, except that the compounds of Formula 4-3 and Formula 4-6 were used in a 1:1 molar ratio instead of the compound of Formula 4-1 in Synthesis Example 1-2, and oxalyl chloride was used instead of terephthaloyl chloride (5.90 g, yield 48.5%).

[0699] 1 H-NMR: 7.85(d, 4H), 7.76(d, 4H), 7.75(d, 4H), 7.72(d, 4H), 2.85(m, 4H), 2.28(s, 6H), 1.55-1.23(m, 19H), 0.86(m, 3H)

[0701] Synthesis Example 11: Synthesis of alkali-soluble resin (B-1)

[0702] 100 parts by weight of propylene glycol monomethyl ether acetate, 100 parts by weight of propylene glycol monomethyl ether, 5 parts by weight of AIBN, 15 parts by weight of vinyltoluene, 20.0 parts by weight of 2-phenylthioethyl acrylate, 3 parts by weight of methacrylate, and 30 parts by weight of methacrylic acid were added to a flask equipped with a stirrer, a thermometer, a reflux condenser, a dropping lot, and a nitrogen inlet tube, and nitrogen was applied. Then, the temperature of the reaction mixture was raised to 80°C while stirring, and the reaction was carried out for 6 hours.

[0703] After that, 15 parts by weight of glycidyl methacrylate were added to the resulting reaction product, the temperature was raised to 110°C, and the reaction was carried out for 4 hours.

[0704] The solid dispersion acid value of the alkali-soluble resin synthesized in this way was 71.9 mgKOH / g, and the weight-average molecular weight (Mw) measured by GPC was approximately 12,160.

[0706] Examples and Comparative Examples: Preparation of Colored Photosensitive Resin Compositions

[0707] Colored photosensitive resin compositions were prepared by mixing each component according to the compositions of Tables 2 to 4 below (Unit: weight%).

[0708] Examples 1 2 3 4 5 6 7 8 9 10 Colorant (A) A-1 28.94 28.94 28.94 28.94 28.94 A-2 16.11 16.11 16.11 16.11 16.11 A-3 29.89 29.89 29.89 29.89 29.89 A-4 5.55 5.55 5.55 5.55 5.55 A-5 16.80 16.80 16.80 16.80 16.80 A-6 A-7 A-8 Alkali-soluble resin (B) B-1 3.71 3.71 3.71 3.71 3.71 1.66 1.66 1.66 1.66 1.66 Photopolymerizable compound (C) C-1 3.12 3.12 3.12 3.12 3.12 3.09 3.09 3.09 3.09 3.09 Photopolymerization initiator (D) D-1 0.35 0.35 D-2 0.35 0.35 D-3 0.35 0.35 D-4 0.35 0.35 D-5 0.35 0.35 D-6 D-7 D-8 Additives (F) F-1 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 Solvent (E) E-1 47.62 47.62 47.62 47.62 47.62 42.51 42.51 42.51 42.51 42.51

[0710] Examples 11 12 13 14 15 16 17 18 19 20 Colorant (A) A-1 A-2 A-3 A-4 A-5 A-6 18.59 18.59 18.59 18.59 18.59 A-7 46.57 46.57 46.57 46.57 46.57 A-8 6.86 6.86 6.86 6.86 6.86 8.76 8.76 8.76 8.76 8.76 Alkali-soluble resin (B) B-1 12.97 12.97 12.97 12.97 12.97 5.29 5.29 5.29 5.29 5.29 Photopolymerizable compound (C) C-1 4.98 4.98 4.98 4.98 4.98 3.90 3.90 3.90 3.90 3.90 Photopolymerization initiator (D) D-1 0.54 0.43 D-2 0.54 0.43 D-3 0.54 0.43 D-4 0.54 0.43 D-5 0.54 0.43 D-6 D-7 D-8 Additives (F) F-1 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 Solvent (E) E-1 55.91 55.91 55.91 55.91 55.91 34.90 34.90 34.90 34.90 34.90

[0712] Comparative example 1 2 3 4 5 6 7 8 9 10 11 12 Colorant (A) A-1 28.94 28.94 28.94 A-2 16.11 16.11 16.11 A-3 29.89 29.89 29.89 A-4 5.55 5.55 5.55 A-5 16.80 16.80 16.80 A-6 18.59 18.59 18.59 A-7 46.57 46.57 46.57 A-8 6.86 6.86 6.86 8.76 8.76 8.76 Alkali-soluble resin (B) B-1 3.71 3.71 3.71 1.66 1.66 1.66 12.97 12.97 12.97 5.29 5.29 5.29 Photopolymerizable compound (C) C-1 3.12 3.12 3.12 3.09 3.09 3.09 4.98 4.98 4.98 3.90 3.90 3.90 Photopolymerization initiator (D) D-1 D-2 D-3 D-4 D-5 D-6 0.35 0.35 0.54 0.43 D-7 0.35 0.35 0.54 0.43 D-8 0.35 0.35 0.54 0.43 Additives (F) F-1 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 0.15 Solvent (E) E-1 47.62 47.62 47.62 42.51 42.51 42.51 55.91 55.91 55.91 34.90 34.90 34.90

[0714] A-1 to A-6: Pigment dispersions of Preparation Examples 1 to 6, respectively

[0715] A-7: Triphenylmethane-based blue dye dispersion of Preparation Example 7

[0716] A-8: Xanthene-based dye dispersion of Preparation Example 8

[0717] B-1: Alkali-soluble resin synthesized in Synthesis Example 11

[0718] C-1: KAYARAD DPHA (Japan Kayaku Co., Ltd.)

[0719] D-1 to D-5: Oxime ester compounds synthesized in Synthesis Examples 1, 3, 4, 7, and 9, respectively.

[0720] D-6: PBG-345 (Tronly Inc.)

[0721] D-7: NCI-831E (Adeka)

[0722] D-8: OXE-02(BASF)

[0723] F-1: F-554 (DIC)

[0724] E-1: Propylene glycol monomethyl ether acetate (PGMEA)

[0726] Experimental Example 1:

[0727] A coating film was prepared as follows using the colored photosensitive resin composition prepared in the above examples and comparative examples, and the physical properties were measured in the following manner, and the results are shown in Tables 5 and 6 below.

[0729] <Manufacture of the film>

[0730] A colored photosensitive resin composition was spin-coated onto the surface of a glass substrate (manufacturer: Corning, thickness: 0.5 mm) in a clean room at 23°C to a thickness of 2.0 μm after drying, and then dried at 90°C for 90 seconds to form a coating layer. After cooling the formed coating layer to 23°C, it was irradiated with light using an exposure device. Subsequently, the exposed thin film was spray-developed with an aqueous solution at 23°C containing 0.04 wt% potassium hydroxide. The glass substrate coated with the thin film was washed with distilled water, and then baked at 230°C for 20 minutes to produce a coating film.

[0732] (1) Membrane shrinkage rate

[0733] In the above film manufacturing process, the film thickness was measured before and after post-baking to observe the change in film thickness before and after.

[0734] At this time, a contact-type film thickness measuring device (model DektakXT, DEKTAK) was used. The film shrinkage rate was calculated according to Equation 1 below. The film shrinkage rate was evaluated according to the following evaluation criteria.

[0735] [Mathematical Formula 1]

[0736] Film shrinkage rate (%) = (Film thickness after post-baking) / (Film thickness before post-baking) × 100

[0738] <Evaluation Criteria>

[0739] ◎: Membrane shrinkage rate 88% or higher

[0740] ○: Membrane shrinkage rate 85% or more and less than 88%

[0741] △: Membrane shrinkage rate 83% or more and less than 85%

[0742] ×: Membrane shrinkage rate less than 83%

[0744] (2) Brightness (heat resistance)

[0745] After heating the coating film prepared by the above method in a heating oven at 230°C for 2 hours, the color change before and after heating was measured to check the change in brightness (ΔY) before and after the heat resistance evaluation, and to check whether there was a decrease in brightness due to thermal yellowing.

[0746] At this time, a microscopic spectrophotometer (model No. OSP-SP2000, Olympus) was used to measure the change in luminance before and after the heat resistance evaluation. The criteria for the luminance (heat resistance) evaluation are as described below.

[0747] <Evaluation Criteria>

[0748] ◎: △Y is -0.05 or greater

[0749] ○: △Y is -0.1 or greater and less than -0.05

[0750] △: △Y is -0.4 or greater and less than -0.1

[0751] ×: △Y is less than -0.4

[0753] (3) Whether double step difference occurs

[0754] After manufacturing the above coating film, the occurrence of double step differences was confirmed using SEM on the Line Space Pattern formed.

[0755] <Evaluation Criteria>

[0756] ○: No double step difference occurred

[0757] ×: Double step difference occurs

[0759] Membrane shrinkage rate Luminance (%) Double step Example 1 ◎ ◎ ○ Example 2 ◎ ◎ ○ Example 3 ◎ ◎ ○ Example 4 ◎ ○ ○ Example 5 ◎ ◎ ○ Example 6 ◎ ◎ ○ Example 7 ◎ ◎ ○ Example 8 ◎ ◎ ○ Example 9 ◎ ○ ○ Example 10 ◎ ◎ ○ Example 11 ◎ ○ ○ Example 12 ◎ ○ ○ Example 13 ◎ ○ ○ Example 14 ◎ ○ ○ Example 15 ◎ ◎ ○ Example 16 ○ ○ ○ Example 17 ○ ○ ○ Example 18 ○ ○ ○ Example 19 ◎ ○ ○ Example 20 ◎ ◎ ○

[0761] Membrane shrinkage rate Luminance (%) Double step Comparative Example 1 △ △ ○ Comparative Example 2 △ △ △ Comparative Example 3 X ◎ X Comparative Example 4 △ △ ○ Comparative Example 5 △ △ △ Comparative Example 6 X △ X Comparative Example 7 △ △ ○ Comparative Example 8 △ △ △ Comparative Example 9 X X X Comparative Example 10 △ △ ○ Comparative Example 11 △ △ △ Comparative Example 12 X △ X

[0763] As shown in Table 5 above, it can be confirmed that the colored photosensitive resin compositions of Examples 1 to 20, which include an oxime ester compound having a specific structure as a photopolymerization initiator according to the present invention, have a low film shrinkage rate, a small decrease in brightness, and no double step difference when forming a pattern.

[0764] On the other hand, as shown in Table 6 above, the colored photosensitive resin compositions of Comparative Examples 1 to 12, which do not contain an oxime ester compound having a specific structure as a photopolymerization initiator, were found to have a high film shrinkage rate, a large decrease in brightness, or a double step difference when forming a pattern.

[0766] As specific parts of the present invention have been described in detail above, it is evident to those skilled in the art that such specific descriptions are merely preferred embodiments and do not limit the scope of the present invention. Those skilled in the art will be able to make various applications and modifications within the scope of the present invention based on the above description.

[0767] Accordingly, the substantial scope of the present invention shall be defined by the appended claims and their equivalents.

Claims

Claim 1 A colored photosensitive resin composition comprising a coloring agent, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent, wherein the photopolymerization initiator comprises an oxime ester compound represented by any one of the following chemical formulas 1 to 3: [Chemical Formula 1] [Chemical Formula 2] [Chemical Formula 3] In the above equation, R 1 , R 8 and R 11 C1-C each independently 20 It is an alkyl group or an aryl group of, and R 2 , R 3 , R 9 , R 10 , R 12 and R 13 C1-C each independently 20 alkyl group of, C4-C 16 cycloalkylalkyl group of, C6-C 21 arylalkyl group of, C2-C 20 The alkoxyalkyl group or C3-C 21 It is an alkoxycarbonylalkyl group of, and Y 1 to Y 3 Each independently has a direct bond, an arylene group, or a C3-C 10 It is a cycloalkylene group of, and R 4 to R 7 , R 14 and R 15 C1-C each independently 20 alkyl group of, C4-C 16 cycloalkylalkyl group of, C6-C 21 arylalkyl group of, C2-C 20 It is an alkoxyalkyl group or an aryl group. Claim 2 In paragraph 1, R 1 C1-C 20 It is an alkyl group or an aryl group of, and R 2 and R 3 C1-C each independently 20 alkyl group of, C4-C 16 cycloalkylalkyl group of, C6-C 21 arylalkyl group or C2-C 20 It is an alkoxyalkyl group of, and Y 1 is a directly bonded or arylene group, and R 4 to R 7 C1-C each independently 20 Colored photosensitive resin composition having an alkyl group. Claim 3 In paragraph 1, R 8 C1-C 20 It is an alkyl group of, and R 9 and R 10 C1-C each independently 20 alkyl group of, C4-C 16 cycloalkylalkyl group of, C6-C 21 arylalkyl group or C2-C 20 It is an alkoxyalkyl group of, and Y 2 is a colored photosensitive resin composition containing an arylene group. Claim 4 In paragraph 1, R 11 C1-C 20 It is an alkyl group of, and R 12 and R 13 C1-C each independently 20 alkyl group of, C4-C 16 cycloalkylalkyl group of, C2-C 20 The alkoxyalkyl group or C3-C 21 It is an alkoxycarbonylalkyl group of, and Y 3 is a directly bonded or arylene group, and R 14 and R 15 C1-C each independently 20 Colored photosensitive resin composition having an alkyl group. Claim 5 In paragraph 1, R 1 , R 8 and R 11 A colored photosensitive resin composition in which each is independently a methyl group or a phenyl group. Claim 6 In paragraph 1, R 2 , R 3 , R 9 , R 10 , R 12 and R 13 C1-C each independently 10 A colored photosensitive resin composition comprising an alkyl group, a cyclopentylmethyl group, a cyclohexylmethyl group, a benzyl group, a methoxymethyl group, or an ethoxycarbonylmethyl group. Claim 7 In paragraph 1, Y 1 to Y 3 A colored photosensitive resin composition in which each is independently directly bonded, a phenylene group, or a naphthylene group. Claim 8 In paragraph 1, R 1 , R 8 and R 11 Each is independently a methyl group or a phenyl group, and R 2 , R 3 , R 9 , R 10 , R 12 and R 13 C1-C each independently 10 It is an alkyl group, cyclopentylmethyl group, cyclohexylmethyl group, benzyl group, methoxymethyl group, or ethoxycarbonylmethyl group, and Y 1 to Y 3 are each independently directly bonded to a phenylene group or a naphthylene group, and R 4 to R 7 , R 14 and R 15 C1-C each independently 10 Colored photosensitive resin composition having an alkyl group. Claim 9 A colored photosensitive resin composition according to claim 1, wherein the oxime ester compound is included in an amount of 5% by weight or more based on 100% by weight of the total photopolymerization initiator. Claim 10 A colored pattern formed using a colored photosensitive resin composition according to any one of claims 1 to 9. Claim 11 A color filter including a coloring pattern according to Clause 10. Claim 12 An image display device characterized by having a color filter according to Clause 11. Claim 13 A solid-state imaging element characterized by being equipped with a color filter according to claim 11.

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