Colored resin composition, optical filter, and solid-state imaging device

Abstract

The present invention addresses the problem of providing a colored resin composition capable of forming an optical filter having excellent heat resistance. According to the present invention, it is possible to provide a colored resin composition containing a colorant, an alkali-soluble resin, and a solvent. The colorant includes at least one selected from the group consisting of compounds represented by formula (I) and formula (II). The maximum absorption wavelength in the wavelength range of 380-1400 nm is 799 nm or less. [In formula (I), M1 represents a divalent metal atom. And R1-R8 each represents a hydrocarbon group having 1-20 carbon atoms, or the like. And R17 represents a hydrocarbon group having 1-20 carbon atoms, or the like. And A1-A8 independently represent an aryl group having 6-20 carbon atoms, or the like. ] [In formula (II), M2 represents a divalent metal atom. And R9-R16 each represents a saturated hydrocarbon group having 1-10 carbon atoms. And A9-A16 each represents an aryl group having 6-20 carbon atoms, or the like. ] # imgabs0 #

Description

Technical Field

[0001] The present invention relates to a colored resin composition, an optical filter, and a solid-state imaging device. Background Art

[0002] In various fields such as automobiles, home appliances, and security, near-infrared sensors, near-infrared cameras, and other devices are used to detect people. In such a device, a solid-state imaging device is provided with an optical filter having a low transmittance of visible light and a high transmittance of near-infrared light. The optical filter used in the solid-state imaging device is manufactured, for example, from a colored resin composition. As such a colored resin composition, a colored resin composition containing, for example, a colorant, a resin, and a solvent is known (Patent Document 1).

[0003] Prior art literature

[0004] Patent Literature

[0005] Patent Document 1: Japanese Patent Application Publication No. 2021-060580 Summary of the invention

[0006] Problems to be solved by the invention

[0007] Optical filters used in solid-state imaging devices are required to have sufficient near-infrared transmittance. In addition, from the perspective of the use environment, they are also required to have sufficient heat resistance and light resistance. However, the heat resistance and light resistance of conventional optical filters are not necessarily sufficient, and there is room for improvement.

[0008] Therefore, a main object of the present invention is to provide a colored resin composition capable of forming an optical filter having excellent heat resistance.

[0009] Means for solving problems

[0010] The present invention provides the colored resin composition described in [1] to [4], the optical filter described in [5], and the solid-state imaging device described in [6].

[0011] [1] A colored resin composition comprising a colorant, an alkali-soluble resin and a solvent,

[0012] The colorant comprises at least one selected from the group consisting of compounds represented by formula (I) and formula (II),

[0013] The colored resin composition has a maximum absorption wavelength of 799 nm or less in the wavelength range of 380 to 1400 nm.

[0014] [Chemical formula 1]

[0015]

[0016] [In formula (I), M 1 It represents a divalent metal atom.

[0017] R 1 ~R 8 Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or OR 17 Group.

[0018] A 1 ~A 8 Each independently represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms.

[0019] R 17 represents a hydrocarbon group having 1 to 20 carbon atoms, in the presence of two or more R 17 In the case of , they may be the same as or different from each other.]

[0020] [Chemical formula 2]

[0021]

[0022] [In formula (II), M 2 It represents a divalent metal atom.

[0023] R 9 ~R 16 Each independently represents a saturated hydrocarbon group having 1 to 10 carbon atoms.

[0024] A 9 ~A 16 Each independently represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms.]

[0025] [2] The colored resin composition according to [1], wherein M in the formula (I) 1 and M of the aforementioned formula (II) 2 At least one of them is a nickel atom.

[0026] [3] The colored resin composition according to claim [1] or [2], wherein R 1 ~R 8 A hydrogen atom.

[0027] [4] The colored resin composition according to any one of [1] to [3], further comprising at least one of a polymerizable compound and a polymerization initiator.

[0028] [5] An optical filter formed from the colored resin composition according to any one of [1] to [4].

[0029] [6] A solid-state imaging device comprising the optical filter described in [5].

[0030] Effects of the Invention

[0031] According to the present invention, a colored resin composition capable of forming an optical filter having excellent heat resistance can be provided. In addition, the obtained optical filter is also excellent in terms of light resistance. In addition, according to the present invention, an optical filter formed by such a colored resin composition and a solid-state imaging device comprising the optical filter can be provided. DETAILED DESCRIPTION

[0032] Hereinafter, embodiments of the present invention will be described in detail, but the present invention is not limited to the following embodiments.

[0033] In this specification, the numerical range shown by "~" indicates a range including the numerical values ​​recorded before and after "~" as the minimum value and the maximum value, respectively. In the numerical range recorded in stages in this specification, the upper limit value or lower limit value recorded in one numerical range can be replaced by the upper limit value or lower limit value of the numerical range recorded in other stages. In addition, in the numerical range recorded in this specification, the upper limit value or lower limit value of the numerical range can be replaced by the value shown in the embodiment.

[0034] In this specification, (meth)acrylate refers to acrylate or its corresponding methacrylate. The same applies to other similar expressions such as (meth)acryloyl, (meth)acrylate, etc.

[0035] In this specification, the materials exemplified below may be used alone or in combination of two or more within the scope of the conditions unless otherwise specified. Regarding the content of each component, when there are multiple substances belonging to each component, it refers to the total amount of the multiple substances unless otherwise specified.

[0036] [Colored resin composition]

[0037] The colored resin composition of the present embodiment contains a colorant (hereinafter sometimes referred to as "colorant (A)"), an alkali-soluble resin (hereinafter sometimes referred to as "resin (B)"), and a solvent (hereinafter sometimes referred to as "solvent (E)"). The colored resin composition of the present embodiment may further contain at least one of a polymerizable compound (hereinafter sometimes referred to as "polymerizable compound (C)") and a polymerization initiator (hereinafter sometimes referred to as "polymerization initiator (D)"), preferably containing both a polymerizable compound and a polymerization initiator. The colored resin composition of the present embodiment may contain a leveling agent (hereinafter sometimes referred to as "leveling agent (F)").

[0038] <Colorant (A)>

[0039] The colorant (A) contains at least one selected from the group consisting of compounds represented by formula (I) and formula (II) (hereinafter sometimes referred to as "colorant (A1)").

[0040] [Chemical formula 3]

[0041]

[0042] M 1 Represents a divalent metal atom. Examples of the divalent metal atom include atoms such as copper, zinc, iron, cobalt, nickel, ruthenium, lead, rhodium, palladium, platinum, manganese, and tin. Among them, the divalent metal atom is preferably an iron atom, a nickel atom, a palladium atom, a platinum atom, a copper atom, or a zinc atom, more preferably a nickel atom, a palladium atom, or a copper atom, further preferably a nickel atom or a palladium atom, and particularly preferably a nickel atom.

[0043] R 1 ~R 8 Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or OR 17 In one embodiment, R 1 ~R 8 It may be a hydrogen atom.

[0044] As R 1 ~R 8 The hydrocarbon group having 1 to 20 carbon atoms in the group includes, for example, alkyl groups such as methyl, ethyl, propyl, butyl, hexyl, octyl, and dodecyl; aryl groups such as phenyl, o-tolyl, m-tolyl, p-tolyl, 2,4,6-trimethylphenyl, and naphthyl; and aralkyl groups such as benzyl and phenethyl. Some of the hydrogen atoms in these alkyl, aryl, and aralkyl groups may be substituted with halogen atoms (fluorine, chlorine, bromine, and iodine atoms, etc.).

[0045] R 17 represents a hydrocarbon group having 1 to 20 carbon atoms, in the presence of two or more R 17 In the case of , they may be the same as or different from each other. 17 The hydrocarbon group having 1 to 20 carbon atoms in R 1 ~R 8 The groups exemplified in the hydrocarbon group having 1 to 20 carbon atoms.

[0046] A 1 ~A 8 Each independently represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms. Some of the hydrogen atoms in the aryl group and the heteroaryl group may be substituted with a halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom, etc.) or an alkoxy group having 1 to 20 carbon atoms. 1 ~A 8The phenyl group may be substituted with an alkoxy group having 1 to 20 carbon atoms.

[0047] A 1 ~A 8 The aryl group having 6 to 20 carbon atoms in the aryl group may be, for example, a monocyclic or polycyclic (for example, a 2-ring or 3-ring) aryl group. Specific examples of the aryl group include phenyl, o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 4-vinylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, o-tert-butylphenyl, m-tert-butylphenyl, p-tert-butylphenyl, 3,5-di(tert-butyl)phenyl, 3,5-di(tert-butyl)-4-methylphenyl, 4 4-butylphenyl, 4-pentylphenyl, 2,6-bis(1-methylethyl)phenyl, 2,4,6-tris(1-methylethyl)phenyl, 4-cyclohexylphenyl, 2,4,6-trimethylphenyl, 4-octylphenyl, 4-(1,1,3,3-tetramethylbutyl)phenyl, 1-naphthyl, 2-naphthyl, 6-methyl-2-naphthyl, 5,6,7,8-tetrahydro-1-naphthyl, 5,6,7,8-tetrahydro-2-naphthyl, fluorenyl, phenanthrenyl, anthracenyl, 2-dodecylphenyl, 3-dodecylphenyl, 4-dodecylphenyl, phenanthrenyl, fluorenyl, biphenyl, etc. The number of carbon atoms in the aryl group is preferably 6 to 18, more preferably 6 to 15, and even more preferably 6 to 12.

[0048] A 1 ~A 8 The heteroaryl group having 3 to 20 carbon atoms in the group may be, for example, a monocyclic or polycyclic (for example, 2-ring or 3-ring) heteroaryl group. Specific examples of heteroaryl groups include furanyl, benzofuranyl, pyridyl, pyrimidyl, pyrazinyl, pyridazinyl, thienyl, benzothienyl, oxazolyl, benzoxazolyl, thiazolyl, benzothiazolyl, indolyl, carbazolyl, acridinyl, imidazolyl, benzimidazolyl, quinolyl, and isoquinolyl. The number of carbon atoms in the heteroaryl group is preferably 3 to 18, more preferably 3 to 12, and even more preferably 3 to 9. In addition, the number of atoms constituting the ring of the heteroaryl group is preferably 5 to 10.

[0049] As can be with A 1 ~A 8Examples of the alkoxy group in which a part of the hydrogen atoms of the aryl group or heteroaryl group are substituted include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy, tert-butoxy, n-pentyloxy, isopentyloxy, neopentyloxy, n-hexyloxy, cyclohexyloxy, n-heptyloxy, n-octyloxy, 2-ethylhexyloxy, tert-octyloxy, decyloxy, undecyloxy, dodecyloxy, tridecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy, octadecyloxy, and nonadecyloxy. The number of carbon atoms in the alkoxy group is preferably 1 to 18, more preferably 1 to 15, further preferably 1 to 10, and particularly preferably 1 to 8.

[0050] [Chemical formula 4]

[0051]

[0052] In formula (II), M 2 Represents a divalent metal atom. Examples of the divalent metal atom include atoms such as copper, zinc, iron, cobalt, nickel, ruthenium, lead, rhodium, palladium, platinum, manganese, and tin. Among them, the divalent metal atom is preferably an iron atom, a nickel atom, a palladium atom, a platinum atom, a copper atom, or a zinc atom, more preferably a nickel atom, a palladium atom, or a copper atom, further preferably a nickel atom or a palladium atom, and particularly preferably a nickel atom.

[0053] R 9 ~R 16 Each independently represents a saturated hydrocarbon group having 1 to 10 carbon atoms. The saturated hydrocarbon group having 1 to 10 carbon atoms may be any of linear, branched, and cyclic. Examples of saturated hydrocarbon groups having 1 to 10 carbon atoms include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl; branched alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl; and cyclic alkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and adamantyl. Some of the hydrogen atoms in these saturated hydrocarbon groups may be substituted with halogen atoms (fluorine atoms, chlorine atoms, bromine atoms, iodine atoms, etc.). The number of carbon atoms in the linear alkyl group and the branched alkyl group is preferably 1 to 8, and more preferably 1 to 6. The number of carbon atoms in the cyclic alkyl group is preferably 3 to 10, and more preferably 6 to 10.

[0054] A 9 ~A 16 Each independently represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms. Some of the hydrogen atoms in the aryl group and the heteroaryl group may be substituted with a halogen atom (fluorine atom, chlorine atom, bromine atom, iodine atom, etc.) or an alkoxy group having 1 to 20 carbon atoms. 9 ~A 16The phenyl group may be substituted with an alkoxy group having 1 to 20 carbon atoms.

[0055] As A 9 ~A 16 The aryl group having 6 to 20 carbon atoms in A 1 ~A 8 The groups exemplified in the aryl group having 6 to 20 carbon atoms.

[0056] As A 9 ~A 16 The heteroaryl group having 3 to 20 carbon atoms in A 1 ~A 8 The groups exemplified in the heteroaryl group having 3 to 20 carbon atoms.

[0057] As can be with A 9 ~A 16 The alkoxy group in which a part of the hydrogen atoms of the aryl group or heteroaryl group are substituted includes 1 ~A 8 The groups exemplified in the alkoxy group in which a part of the hydrogen atoms of the aryl group or heteroaryl group are substituted.

[0058] In the colorant (A), as a colorant (A1), at least one selected from the group consisting of compounds represented by formula (I) and formula (II) is included, preferably both a compound represented by formula (I) (at least one selected from the compounds represented by formula (I)) and a compound represented by formula (II) (at least one selected from the compounds represented by formula (II)). By making the colorant (A) contain both a compound represented by formula (I) and a compound represented by formula (II) as a colorant (A1), an optical filter having near-infrared transmittance can be obtained, and the optical filter also has good sensitivity as a sensor and excellent heat resistance and light resistance.

[0059] When the colorant (A) contains both the compound represented by formula (I) and the compound represented by formula (II) as the colorant (A1), the content ratio (mass ratio) of the compound represented by formula (I): the compound represented by formula (II) is preferably 1:10 to 10:1, more preferably 1:5 to 5:1, and even more preferably 1:4 to 4:1.

[0060] The content of the colorant (A1) is preferably 10 to 100% by mass, more preferably 20 to 100% by mass, and even more preferably 30 to 100% by mass based on the total amount of the colorant (A). In one embodiment, the content of the colorant (A1) can be 100% by mass based on the total amount of the colorant (A).

[0061] The colorant (A) may further contain a colorant different from the colorant (A1) (hereinafter, sometimes referred to as "colorant (A2)").

[0062] Examples of the colorant (A2) include dyes and pigments.

[0063] Examples of the dye include compounds classified as substances having a hue other than pigments in the Color Index (published by The Society of Dyers and Colourists) and known dyes described in the Dyeing Guide (published by the Color Dyeing Co., Ltd.).

[0064] Xanthene dyes are dyes containing compounds having a xanthene skeleton in the molecule. Examples of xanthene dyes include CI Acid Red 51 (hereinafter, the description of "CI Acid Red" is omitted and only the number is recorded. Other similar expressions are also similar, and sometimes only the number is recorded.), 52, 87, 92, 94, 289, 388; CI Acid Violet 9, 30, 102; CI Basic Red 1 (Rhodamine 6G), 2, 3, 4, 8, 10, 11; CI Basic Violet 10 (Rhodamine B), 11; CI Solvent Red 218; CI Mordant Red 27; CI Reactive Red 36 (Rhodamine B); Sulforhodamine G; xanthene dyes described in Japanese Patent Publication No. 2010-32999; xanthene dyes described in Japanese Patent Publication No. 4492760, etc. The xanthene dye is preferably a dye soluble in an organic solvent.

[0065] The xanthene dye may be a commercially available xanthene dye (e.g., "Chugai Aminol Fast Pink RH / C" manufactured by Chugai Chemical Co., Ltd., "Rhodamin 6G" manufactured by Taoka Chemical Industry Co., Ltd.) Alternatively, the xanthene dye may be synthesized using a commercially available xanthene dye as a starting material with reference to Japanese Patent Application Laid-Open No. 2010-32999.

[0066] As dyes other than xanthene dyes, azo dyes, cyanine dyes, triphenylmethane dyes, thiazole dyes, oxazine dyes, phthalocyanine dyes, quinophthalone dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, etc. can be used. As dyes other than xanthene dyes, known dyes can be used.

[0067] Specific examples of dyes other than xanthene dyes include CI Solvent Yellow 4 (hereinafter, CI Solvent Yellow is omitted and only the number is described. Similarly, other similar expressions may only be described with the number.), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, 189;

[0068] CI Solvent Red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 222, 227, 230, 245, 247;

[0069] CI Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86;

[0070] CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

[0071] CI Solvent Blue 4, 5, 14, 18, 35, 36, 37, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;

[0072] CI solvent dyes such as CI Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc.

[0073] 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, 156 7, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;

[0074] CI Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 57, 66, 73, 76, 80, 88, 91, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176, 182, 183 , 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, ​​383, 394, 401, 412, 417, 418, 422, 426;

[0075] CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;

[0076] CI Acid Violet 6B, 7, 15, 16, 17, 19, 21, 23, 24, 25, 34, 38, 49, 72;

[0077] CI Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123 , 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324:1, 335, 340;

[0078] CI acid green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109 and other CI acid dyes,

[0079] 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;

[0080] 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;

[0081] CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

[0082] CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

[0083] CI Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167 7, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293;

[0084] CI direct green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82 and other CI direct dyes,

[0085] CI Disperse Yellow 51, 54, 76;

[0086] CI Disperse Violet 26, 27;

[0087] CI disperse blue 1, 14, 56, 60 and other CI disperse dyes,

[0088] CI basic blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89;

[0089] CI Basic Violet 2;

[0090] CI Basic Red 9;

[0091] CI basic dyes such as CI Basic Green 1,

[0092] CI Reactive Yellow 2, 76, 116;

[0093] CI Reactive Orange 16;

[0094] CI reactive dyes such as CI Reactive Red 36,

[0095] CI Medium Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

[0096] CI Medium Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95;

[0097] CI Medium Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;

[0098] CI medium violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58;

[0099] CI Medium 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;

[0100] CI mordant green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53 and other CI mordant dyes,

[0101] CI vat dyes such as CI vat green 1, etc.

[0102] Examples of the pigment include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists). Examples of such pigments include the following pigments.

[0103] Green pigment: CI Pigment Green 7, 36, 58, etc.

[0104] Yellow pigment: CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, etc.

[0105] Orange pigment: CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, etc.

[0106] Red pigment: CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, etc.

[0107] Blue pigment: CI Pigment Blue 15, 15:3, 15:4, 15:6, 60, etc.

[0108] Purple pigment: CI pigment violet 1, 19, 23, 29, 32, 36, 38, etc.

[0109] Black pigment: CI Pigment Black 1, 7, 31, 32, etc.

[0110] These pigments may be used alone or in combination for each color.

[0111] The colorant (A2) is preferably one or more pigments, more preferably two or more pigments, further preferably two or more pigments selected from the group consisting of orange pigments, violet pigments, blue pigments and black pigments, and particularly preferably a combination of an orange pigment, a violet pigment and a blue pigment or a combination of a blue pigment and a black pigment.

[0112] The pigment may be subjected to the following as required: rosin treatment; surface treatment using pigment derivatives introduced with acidic or basic groups; grafting treatment onto the pigment surface using polymer compounds; micronization treatment using sulfuric acid micronization method; cleaning treatment for removing impurities using organic solvents, water, etc.; removal of ionic impurities using ion exchange method, etc. The particle size of the pigment is preferably roughly uniform. By dispersing the pigment containing a pigment dispersant, a pigment dispersion can be prepared in a state where the pigment is uniformly dispersed in a pigment dispersant solution. The pigments may be dispersed individually or a plurality of pigments may be mixed and dispersed.

[0113] As pigment dispersants, surfactants such as silicone, fluorine, ester, cationic, anionic, nonionic, amphoteric, polyester, polyamine, acrylic, etc. can be cited. As surfactants, polyoxyethylene alkyl ethers, polyoxyethylene alkylphenyl ethers, polyethylene glycol diesters, sorbitan fatty acid esters, fatty acid modified polyesters, tertiary amine modified polyurethanes, polyethyleneimines, etc. can be cited. As commercial products of surfactants, for example, KP (Shin-Etsu Chemical Industry (Strain) system), FLOWLEN (Kyoeisha Chemical (Strain) system), SOLSPERSE (Zeneca (Strain) system), EFKA (BASF Japan (Strain) system), AJISPER (registered trademark) (Ajinomoto Fine-Techno (Strain) system), Disperbyk (BYK-Chemie company system) etc. can be cited by trade name.

[0114] When a pigment dispersant is used, its usage is preferably 10 to 200 parts by mass, more preferably 15 to 180 parts by mass, and further preferably 20 to 160 parts by mass relative to 100 parts by mass of the pigment. If the usage of the pigment dispersant is within the above range, when two or more pigments are used, there is a tendency to obtain a pigment dispersion liquid in a more uniform dispersion state.

[0115] The content of the colorant (A2) is preferably 0 to 90% by mass, more preferably 0 to 80% by mass, and even more preferably 0 to 70% by mass, based on the total amount of the colorant (A).

[0116] Based on the total amount of the solid content of the colored resin composition, the content of the colorant (A) is preferably 1 to 60% by mass, more preferably 5 to 60% by mass, and further preferably 10 to 60% by mass. If the content of the colorant (A) is within the above range, it is easier to obtain the desired spectroscopic and color concentration. It should be noted that in this specification, the so-called "total amount of the solid content of the colored resin composition" refers to the total amount of the components obtained by removing the solvent from the colored resin composition. The total amount of the solid content of the colored resin composition and the content of each component relative to it can be measured by known analytical means such as liquid chromatography and gas chromatography.

[0117] <Resin (B)>

[0118] Examples of the resin (B) include the following resins [K1] to [K6].

[0119] Resin [K1]: A copolymer having a structural unit derived from at least one (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter sometimes referred to as "(a)") and a structural unit derived from a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b)").

[0120] Resin [K2]: A copolymer having a structural unit derived from (a), a structural unit derived from (b), and a structural unit derived from a monomer (c) copolymerizable with (a) (however, different from (a) and (b)) (hereinafter sometimes referred to as "(c)")

[0121] Resin [K3]: A copolymer having a structural unit derived from (a) and a structural unit derived from (c)

[0122] Resin [K4]: A copolymer having a structural unit in which (b) is added to a structural unit derived from (a), and a structural unit derived from (c)

[0123] Resin [K5]: A copolymer having a structural unit in which (a) is added to a structural unit derived from (b), and a structural unit derived from (c)

[0124] Resin [K6]: A copolymer having a structural unit obtained by adding (a) to a structural unit derived from (b) and further adding a carboxylic acid anhydride, and a structural unit derived from (c)

[0125] Specific examples of (a) include:

[0126] Unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid;

[0127] Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, 1,4-cyclohexenedicarboxylic acid, etc.;

[0128] Bicyclic unsaturated compounds containing a carboxyl group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene;

[0129] Unsaturated dicarboxylic anhydrides such as maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride;

[0130] Unsaturated mono[(meth)acryloyloxyalkyl] esters of polycarboxylic acids having a valence of 2 or more, such as mono[2-(meth)acryloyloxyethyl]succinate and mono[2-(meth)acryloyloxyethyl]phthalate;

[0131] Unsaturated acrylic acid esters containing a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylic acid, etc.

[0132] Among them, (a) is preferably acrylic acid, methacrylic acid or maleic anhydride from the viewpoint of copolymerization reactivity and solubility of the obtained resin in an alkaline aqueous solution.

[0133] (b) may be, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (e.g., at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and an ethylenically unsaturated bond. (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0134] As (b), for example, there can be mentioned a monomer (b1) having an ethylene oxide group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)"), a monomer (b2) having an oxetane group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b2)"), a monomer (b3) having a tetrahydrofuranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)"), etc.

[0135] As (b1), for example, there can be mentioned a monomer (b1-1) having a structure in which a straight-chain or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-1)") and a monomer (b1-2) having a structure in which alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-2)").

[0136] Examples of (b1-1) include glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl o-vinylbenzyl glycidyl ether, α-methyl m-vinylbenzyl glycidyl ether, α-methyl p-vinylbenzyl glycidyl ether, 2,3-bis(glycidyloxymethyl) Styrene, 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tri(glycidyloxymethyl)styrene, 2,3,5-tri(glycidyloxymethyl)styrene, 2,3,6-tri(glycidyloxymethyl)styrene, 3,4,5-tri(glycidyloxymethyl)styrene, 2,4,6-tri(glycidyloxymethyl)styrene, and the like.

[0137] Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000 (manufactured by Daicel)), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer A400 (manufactured by Daicel)), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer M100 (manufactured by Daicel)), 3,4-epoxytricyclo[5.2.1.0](meth)acrylate, 2,6 ]Decyl ester ((meth)acrylate 3,4-epoxytricyclo[5.2.1.0 2,6 ] decane-8-yl ester, (meth)acrylate 3,4-epoxytricyclo[5.2.1.0 2,6 ] decane-9-yl ester, etc.), (meth) acrylic acid 3,4-epoxytricyclo[5.2.1.0 2,6 ]Decyloxyethyl ester, etc.

[0138] (b2) is more preferably a monomer having an oxetane group and a (meth)acryloyloxy group. As (b2), 3-methyl-3-methacryloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, 3-ethyl-3-acryloyloxymethyloxetane, 3-methyl-3-methacryloyloxyethyloxetane, 3-methyl-3-acryloyloxyethyloxetane, 3-ethyl-3-methacryloyloxyethyloxetane, 3-ethyl-3-acryloyloxyethyloxetane, etc. can be mentioned.

[0139] (b3) is more preferably a monomer having a tetrahydrofuranyl group and a (meth)acryloyloxy group. Examples of (b3) include tetrahydrofurfuryl acrylate (for example, Viscoat V#150 (manufactured by Osaka Organic Chemical Industry Co., Ltd.)) and tetrahydrofurfuryl methacrylate.

[0140] From the perspective of being able to further improve the reliability of the obtained optical filter, such as heat resistance and chemical resistance, (b) is preferably (b1). Furthermore, from the perspective of excellent storage stability of the colored resin composition, (b) is more preferably (b1-2).

[0141] As (c), for example, there can be mentioned:

[0142] Methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 ] decane-8-yl ester (in the technical field, it is commonly known as "dicyclopentanyl (meth)acrylate". In addition, it is sometimes referred to as "tricyclodecyl (meth)acrylate".), tricyclo[5.2.1.0 2,6 (Meth)acrylates such as decen-8-yl ester (also known as "dicyclopentenyl (meth)acrylate" as a common name in the art), dicyclopentyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate;

[0143] (Meth)acrylates containing a hydroxyl group, such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate;

[0144] Diethyl maleate, diethyl fumarate, diethyl itaconate and other dicarboxylic acid diesters;

[0145] bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-bis(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-bis(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept-2-ene Bicyclic unsaturated compounds such as bicyclo[2.2.1]hept-2-ene, 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene, and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene;

[0146] Dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidohexanoate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide;

[0147] Styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, etc.

[0148] Among them, (c) is preferably styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide or bicyclo[2.2.1]hept-2-ene from the viewpoint of copolymerization reactivity and heat resistance.

[0149] In the resin [K1], the ratio of the structural units derived from each of the above among all the structural units constituting the resin [K1] is preferably:

[0150] Structural unit derived from (a): 2 to 60 mol%

[0151] Structural unit derived from (b): 40 to 98 mol %

[0152] More preferably:

[0153] Structural unit derived from (a): 10 to 50 mol%

[0154] Structural unit derived from (b): 50 to 90 mol %.

[0155] When the ratio of the structural unit of the resin [K1] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance of the obtained optical filter tend to be excellent.

[0156] The resin [K1] can be produced, for example, by referring to the method described in the document "Experimental Methods for Polymer Synthesis" (written by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st print, published on March 1, 1972) and the cited documents described in the document.

[0157] Specifically, the following method can be cited: a specified amount of (a) and (b), a polymerization initiator and a solvent are added to a reaction vessel, for example, oxygen is replaced with nitrogen to form a deoxygenated atmosphere, and heating and heat preservation are performed while stirring. It should be noted that the polymerization initiator and solvent used here are not particularly limited, and substances commonly used in this field can be used. For example, as a polymerization initiator, azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile)), organic peroxides (benzoyl peroxide, etc.) can be cited. The solvent can be any solvent that dissolves each monomer, for example, the solvent exemplified in the solvent (E) described later can be used.

[0158] It should be noted that the obtained copolymer can be used directly as a solution after the reaction, or a concentrated or diluted solution can be used. In addition, the obtained copolymer can also be used as a substance taken out in the form of a solid (powder) by a method such as reprecipitation. In particular, by using a solvent (E) described later as a solvent during the polymerization, the solution after the reaction can be used for the preparation of the colored resin composition, so that the manufacturing process of the colored resin composition of this embodiment can be simplified.

[0159] In the resin [K2], the ratio of the structural units derived from each of the above among all the structural units constituting the resin [K2] is preferably:

[0160] Structural unit derived from (a): 2 to 45 mol%

[0161] Structural unit derived from (b): 2 to 95 mol%

[0162] Structural unit derived from (c): 1 to 65 mol %

[0163] More preferably:

[0164] Structural unit derived from (a): 5 to 40 mol%

[0165] Structural unit derived from (b): 5 to 80 mol%

[0166] Structural unit derived from (c): 5 to 60 mol %.

[0167] When the ratio of the structural unit of the resin [K2] is within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance, heat resistance, and mechanical strength of the obtained optical filter tend to be excellent.

[0168] The resin [K2] can be produced, for example, in the same manner as described as the method for producing the resin [K1].

[0169] In the resin [K3], the ratio of the structural units derived from each of the above among all the structural units constituting the resin [K3] is preferably:

[0170] Structural unit derived from (a): 2 to 60 mol%

[0171] Structural unit derived from (c): 40 to 98 mol %

[0172] More preferably:

[0173] Structural unit derived from (a): 10 to 50 mol%

[0174] Structural unit derived from (c): 50 to 90 mol %.

[0175] The resin [K3] can be produced, for example, in the same manner as described as the method for producing the resin [K1].

[0176] The resin [K4] can be produced by obtaining a copolymer of (a) and (c), and adding a cyclic ether having 2 to 4 carbon atoms contained in (b) to the carboxylic acid and / or carboxylic anhydride contained in (a).

[0177] First, a copolymer of (a) and (c) is produced in the same manner as described as the method for producing resin [K1]. In this case, the ratio of the structural units derived from each is preferably the same as the ratio exemplified in resin [K3].

[0178] Next, the cyclic ether having 2 to 4 carbon atoms contained in (b) is reacted with a portion of the carboxylic acid and / or carboxylic anhydride derived from (a) in the above copolymer. After the copolymer of (a) and (c) is produced, the atmosphere in the flask is replaced from nitrogen to air, (b), a reaction catalyst (e.g., tris(dimethylaminomethyl)phenol, etc.) and a polymerization inhibitor (e.g., hydroquinone, etc.) for the carboxylic acid or carboxylic anhydride and the cyclic ether are added to the flask, and the reaction is carried out at, for example, 60 to 130° C. for 1 to 10 hours, thereby producing resin [K4].

[0179] The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, relative to 100 mol of (a). By setting it within this range, there is a tendency that the storage stability of the colored resin composition, the developability when forming a pattern, and the balance of the solvent resistance, heat resistance, mechanical strength and sensitivity of the obtained pattern become good. Considering that the reactivity of the cyclic ether is high and it is not easy to leave unreacted (b), the (b) used in the resin [K4] is preferably (b1), more preferably (b1-1).

[0180] The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b) and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass relative to 100 parts by mass of the total amount of (a), (b) and (c).

[0181] The reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted in consideration of production equipment, the amount of heat generated by polymerization, and the like.

[0182] Regarding resin [K5], as a first step, a copolymer of (b) and (c) is obtained in the same manner as in the production method of resin [K1]. As in the above, the obtained copolymer may be used directly as a solution after the reaction, or may be used as a concentrated or diluted solution. In addition, the obtained copolymer may be used as a solid (powder) obtained by a method such as reprecipitation.

[0183] The ratio of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the above-mentioned copolymer is preferably:

[0184] Structural unit derived from (b): 5 to 95 mol%

[0185] Structural unit derived from (c): 5 to 95 mol %

[0186] More preferably:

[0187] Structural unit derived from (b): 10 to 90 mol%

[0188] Structural unit derived from (c): 10 to 90 mol %.

[0189] Furthermore, under the same conditions as in the method for producing resin [K4], the carboxylic acid or carboxylic anhydride contained in (a) is reacted with the cyclic ether derived from (b) contained in the copolymer of (b) and (c), thereby obtaining resin [K5].

[0190] The amount of (a) to be reacted with the copolymer is preferably 5 to 80 mol relative to 100 mol of (b). (b) used in the resin [K5] is preferably (b1), more preferably (b1-1), because the cyclic ether has high reactivity and unreacted (b) is less likely to remain.

[0191] The resin [K6] is a resin obtained by further reacting the resin [K5] with a carboxylic acid anhydride. The carboxylic acid anhydride is reacted with a hydroxyl group generated by the reaction of a cyclic ether with a carboxylic acid or a carboxylic acid anhydride.

[0192] Examples of the carboxylic anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, etc. The amount of the carboxylic anhydride used is preferably 0.5 to 1 mol relative to 1 mol of the amount of (a) used.

[0193] Specific examples of the resin (B) include: 3,4-epoxycyclohexylmethyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] decyl ester / (meth)acrylic acid copolymer resins [K1]; (meth)acrylate glycidyl / (meth)acrylate benzyl / (meth)acrylic acid copolymer, (meth)acrylate glycidyl / styrene / (meth)acrylic acid copolymer, acrylic acid 3,4-epoxy tricyclic [5.2.1.0 2,6 ]decyl ester / (meth)acrylic acid / benzyl (meth)acrylate, 3,4-epoxytricyclo[5.2.1.0 2,6 ] decyl ester / (meth) acrylic acid / N-cyclohexyl maleimide copolymer, acrylic acid 3,4-epoxy tricyclo[5.2.1.0 2,6] decyl ester / (meth)acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer and other resins [K2]; benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer and other resins [K3]; resins obtained by adding glycidyl (meth)acrylate to benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, Resins such as a resin obtained by adding glycidyl (meth)acrylate to a copolymer of cyclodecyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid [K4]; a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate with (meth)acrylic acid, a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / styrene / glycidyl (meth)acrylate with (meth)acrylic acid, etc. [K5]; a resin obtained by reacting a copolymer of tricyclodecyl (meth)acrylate / glycidyl (meth)acrylate with (meth)acrylic acid, and further reacting the resin with tetrahydrophthalic anhydride, etc. [K6], etc.

[0194] The resin (B) is preferably a copolymer comprising at least one structural unit derived from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides, and a structural unit having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond, more preferably resin [K1] or resin [K2], and even more preferably resin [K2].

[0195] The weight average molecular weight of the resin (B) in terms of polystyrene is preferably 3000 to 100000, more preferably 5000 to 50000, and further preferably 5000 to 30000. When the weight average molecular weight is within the above range, the hardness of the optical filter is improved, the residual film rate is high, the solubility of the unexposed portion in the developer is good, and the resolution of the colored pattern is improved.

[0196] The dispersion degree [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably 1.1-6, more preferably 1.2-4.

[0197] The acid value of the resin (B) is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150 mg-KOH / g, and further preferably 70 to 135 mg-KOH / g, based on solid content. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be determined, for example, by titration using a potassium hydroxide aqueous solution.

[0198] The content of the resin (B) is preferably 5 to 60% by mass, more preferably 10 to 55% by mass, and further preferably 20 to 50% by mass, based on the total amount of the solid content of the colored resin composition. When the content of the resin (B) is within the above range, a colored pattern can be formed, and the resolution and residual film rate of the colored pattern tend to be improved.

[0199] <Polymerizable Compound (C)>

[0200] The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated by the polymerization initiator (D). Examples of the polymerizable compound (C) include compounds having polymerizable ethylenically unsaturated bonds. The polymerizable compound (C) is preferably a (meth)acrylate compound.

[0201] The polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris(2-(meth)acryloyloxyethyl)isocyanurate, ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, and caprolactone-modified dipentaerythritol hexa(meth)acrylate. Among them, the polymerizable compound (C) is preferably trimethylolpropane triacrylate, dipentaerythritol penta(meth)acrylate, or dipentaerythritol hexa(meth)acrylate.

[0202] The molecular weight or weight average molecular weight of the polymerizable compound (C) is preferably 150 to 2,900, more preferably 250 to 1,500.

[0203] The content of the polymerizable compound (C) is preferably 5 to 60% by mass, more preferably 10 to 50% by mass, and further preferably 20 to 40% by mass, based on the total amount of the solid content of the colored resin composition. When the content of the polymerizable compound (C) is within the above range, the residual film rate when forming a colored pattern and the chemical resistance of the optical filter tend to be improved.

[0204] <Polymerization Initiator (D)>

[0205] The polymerization initiator (D) is not particularly limited as long as it is a compound that generates active free radicals, acids, etc. under the action of light or heat and can initiate polymerization, and known polymerization initiators can be used. Examples of polymerization initiators that generate active free radicals include O-acyl oxime compounds, alkyl phenone compounds, triazine compounds, acyl phosphine oxide compounds, and biimidazole compounds.

[0206] The O-acyl oxime compound is a compound having a partial structure represented by formula (d1).

[0207] [Chemical formula 5]

[0208]

[0209] Examples of the O-acyl oxime compound include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(

[0063] N-acetyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropane-1-one-2-imine, N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-one-2-imine, etc. As the O-acyl oxime compound, commercially available products such as Irgacure (registered trademark, the same below) OXE01 (N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine), Irgacure OXE02 (N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine) (all manufactured by BASF), and N-1919 (manufactured by ADEKA Corporation) can also be used.

[0210] Among them, the O-acyl oxime compound is preferably selected from N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine, N-acetyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine and At least one of the group consisting of N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, more preferably N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octane-1-one-2-imine or N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine. When such an O-acyl oxime compound is used, an optical filter with high brightness tends to be obtained.

[0211] The alkylphenone compound is a compound having a partial structure represented by formula (d2) or a partial structure represented by formula (d3). In these partial structures, the benzene ring may have a substituent.

[0212] [Chemical formula 6]

[0213]

[0214] Examples of the compound having a partial structure represented by formula (d2) include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propane-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutane-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butane-1-one. Commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) can be used as the compound having a partial structure represented by formula (d2).

[0215] Examples of compounds having a partial structure represented by formula (d3) include 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propane-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1-one, α,α-diethoxyacetophenone, and benzil dimethyl ketal.

[0216] From the viewpoint of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by formula (d2).

[0217] Examples of the triazine compound include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(5-methylfuran-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino)-2

[0218] -methylphenyl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine, and the like.

[0219] Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, etc. As the acylphosphine oxide compound, commercially available products such as Irgacure 819 (manufactured by BASF) can also be used.

[0220] Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, Japanese Patent Application Laid-Open No. 6-75372 and Japanese Patent Application Laid-Open No. 6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, Biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with alkoxycarbonyl groups (for example, see Japanese Patent Publication No. 7-10913, etc.), and the like.

[0221] In addition, examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetrakis (tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzil, methyl phenylglyoxylate, and titanocene compounds, etc. These are preferably used in combination with the polymerization initiator aid (D1) (particularly amines) described later.

[0222] Examples of the polymerization initiator that generates an acid include onium salts such as 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenylmethylbenzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, and diphenyliodonium hexafluoroantimonate, nitrobenzyl toluenesulfonates, and benzoin toluenesulfonates.

[0223] The polymerization initiator (D) preferably contains at least one selected from the group consisting of O-acyl oxime compounds, alkylphenone compounds, triazine compounds, acylphosphine oxide compounds and biimidazole compounds, and more preferably contains an O-acyl oxime compound.

[0224] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). If the content of the polymerization initiator (D) is within the above range, there is a tendency to achieve high sensitivity and shorten the exposure time, so it can be expected that the productivity of the optical filter will be improved.

[0225] <Polymerization initiator aid (D1)>

[0226] The polymerization initiator aid (D1) is a compound or a sensitizer for accelerating the polymerization of the polymerizable compound. When the colored resin composition contains the polymerization initiator aid (D1), it is usually used in combination with the polymerization initiator (D).

[0227] Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0228] As the amine compound, triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isopentyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, 4,4'-bis(ethylmethylamino)benzophenone, etc. can be cited. As the amine compound, commercial products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can also be used. Among them, the amine compound is preferably 4,4'-bis(diethylamino)benzophenone.

[0229] Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.

[0230] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0231] Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0232] When these polymerization initiation aids (D1) are used, the content is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). If the amount of the polymerization initiation aid (D1) is within this range, there is a tendency that a colored pattern can be formed with higher sensitivity, and the productivity of the optical filter is improved.

[0233] <Solvent (E)>

[0234] The solvent (E) is not particularly limited, and a solvent commonly used in this field can be used. For example, an ester solvent (a solvent containing -COO- in the molecule and not containing -O-), an ether solvent (a solvent containing -O- in the molecule and not containing -COO-), an ether ester solvent (a solvent containing -C OO- and -O- in the molecule), a ketone solvent (a solvent containing -CO- in the molecule and not containing -COO-), an alcohol solvent (a solvent containing OH in the molecule and not containing -O-, -CO- and -COO-), an aromatic hydrocarbon solvent, an amide solvent, dimethyl sulfoxide, etc. can be mentioned.

[0235] Examples of the ester solvent include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0236] Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenethyl ether, and methyl anisole.

[0237] Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and diethylene glycol monobutyl ether acetate.

[0238] Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0239] Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0240] Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene, and mesitylene.

[0241] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0242] Among them, the solvent (E) is preferably at least one selected from the group consisting of ether ester solvents and ether solvents, and more preferably propylene glycol monomethyl ether acetate or diethylene glycol ethyl methyl ether.

[0243] The content of the solvent (E) is preferably 70 to 95% by mass, more preferably 75 to 92% by mass, based on the total amount of the colored resin composition. In other words, the solid content of the colored resin composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass, based on the total amount of the colored resin composition. When the content of the solvent (E) is within the above range, the flatness during coating becomes good, and the color density is not easily insufficient when forming an optical filter, so there is a tendency that the display characteristics become good.

[0244] When an ether ester solvent is used, the content of the ether ester solvent is preferably 10 to 100% by mass, more preferably 15 to 90% by mass, and even more preferably 17 to 80% by mass based on the total amount of the solvent.

[0245] When an ether solvent is used, the content of the ether solvent is preferably 20 to 90% by mass, more preferably 30 to 85% by mass, and even more preferably 40 to 80% by mass based on the total amount of the solvent.

[0246] <Leveling agent (F)>

[0247] As the leveling agent (F), there can be mentioned silicone-based surfactants, fluorine-based surfactants, silicone-based surfactants having fluorine atoms, etc. These may have a polymerizable group in a side chain.

[0248] Examples of the silicone-based surfactant include surfactants having a siloxane bond in the molecule. Specific examples include TORAY SILICONE DC3PA, TORAY SILICONE SH7PA, TORAY SILICONE DC11PA, TORAY SILICONE SH21PA, TORAY SILICONE SH28PA, TORAY SILICONE SH29PA, TORAY SILICONE SH30PA, TORAY SILICONE SH8400 (trade names, manufactured by Toray Dow Corning Corporation), KP321, KP322, KP323, KP324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Materials Japan Co., Ltd.).

[0249] Examples of the fluorine-based surfactant include surfactants having a fluorine-carbon chain in the molecule. Specifically, examples include FLOURAD (registered trademark) FC430, FLOURAD FC431 (manufactured by Sumitomo 3M Co., Ltd.), MEGAFACE (registered trademark) F142D, MEGAFACE F171, MEGAFACE F172, MEGAFACE F173, MEGAFACE F177, MEGAFACE F183, MEGAFACE F554, MEGAFACE R30, MEGAFACE RS-718-K (manufactured by DIC Corporation), EFTOP (registered trademark) EF301, EFTOP EF303, EFTOP EF351, EFTOP EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), SURFLON (registered trademark) S381, SURFLON S382, SURFLON SC101, SURFLON SC105 (manufactured by AGC Corporation (formerly Asahi Glass Corporation)) and E5844 (manufactured by Daikin Fine Chemicals Laboratories, Ltd.), etc.

[0250] Examples of the organosilicon-based surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule, and more specifically, MEGAFACE (registered trademark) R08, MEGAFACE BL20, MEGAFACE F475, MEGAFACE F477, and MEGAFACE F443 (manufactured by DIC Corporation).

[0251] The content of the leveling agent (F) is preferably 0.001 to 0.2 mass %, more preferably 0.002 to 0.1 mass %, and further preferably 0.01 to 0.05 mass %, based on the total amount of the colored resin composition. It should be noted that this content does not include the content of the above-mentioned pigment dispersant. If the content of the leveling agent (F) is within the above range, the flatness of the optical filter can be improved.

[0252] <Other ingredients>

[0253] The colored resin composition of the present embodiment may contain additives known in the technical field such as a dispersant, a filler, other polymer compounds, an adhesion promoter, an antioxidant, a light stabilizer, and a chain transfer agent as needed. The colored resin composition of the present embodiment can be suitably used to transmit infrared rays.

[0254] In the colored resin composition of the present embodiment, the maximum absorption wavelength in the range of wavelengths of 380 to 1400 nm is 799 nm or less. If the maximum absorption wavelength is 799 nm or less, there is a tendency to easily absorb light of 780 nm, which is the upper limit of visible light. The maximum absorption wavelength is preferably 795 nm or less, more preferably 790 nm or less, and further preferably 785 nm or less. The lower limit of the maximum absorption wavelength is not particularly limited, for example, it can be 750 nm or more, preferably 755 nm or more, more preferably 760 nm or more, and further preferably 765 nm or more.

[0255] The maximum absorption wavelength in the range of 380 to 1400 nm can be measured using an ultraviolet-visible-near-infrared absorption spectrometer (for example, V-770, manufactured by JASCO Corporation). The measurement method can be carried out, for example, as follows. First, the content of the compounds represented by formula (I) and formula (II) in the colored resin composition is diluted with a solvent (for example, solvent (E) described later) to be 10 mass ppm to prepare a measurement solution. The measurement solution prepared in this way is placed in a 1 cm square quartz cuvette, and the spectrum is measured in the range of 1400 to 300 nm (data collection interval 1 nm) using an ultraviolet-visible-near-infrared absorption spectrometer. At this time, the wavelength showing the maximum value of the absorbance is taken as the maximum absorption wavelength λ max. By operating as described above, the maximum absorption wavelength can be obtained. It should be noted that there is a tendency that the maximum absorption wavelength does not change even when the resin (B), polymerizable compound (C), polymerization initiator (D), etc. described later are present in the measuring solution. Therefore, for example, a solution containing a colorant and a solvent obtained by removing the resin (B), polymerizable compound (C), polymerization initiator (D), etc. described later from the colored resin composition can be prepared as a measuring solution, and the maximum absorption wavelength in the range of 380 to 1400 nm measured using the solution is regarded as the maximum absorption wavelength in the range of 380 to 1400 nm of the colored resin composition.

[0256] In the colored resin composition of the present embodiment, the absorbance Abs(780) at a wavelength of 780 nm and λ max The absorbance Abs(λ max ) ratio (Abs(780) / Abs(λ max )) can be, for example, 0.50 or more. The optical filter needs to absorb light of 780 nm, which is the upper limit of the visible region. Therefore, the larger this value is, the more preferable it is as a characteristic of an optical filter having near-infrared transmittance. Abs(780) / Abs(λ max ) is preferably 0.60 or more, more preferably 0.70 or more, and still more preferably 0.75 or more. Abs(780) / Abs(λ max ) can be, for example, 1.00 or less.

[0257] In the colored resin composition of the present embodiment, the maximum absorbance Abs(900-1400) in the wavelength range of 900 to 1400 nm and λ max The absorbance Abs(λ max ) ratio (Abs(900-1400) / Abs(λ max )) can be, for example, 0.30 or less. The smaller this value is, the higher the transmittance in the near-infrared region is, and the higher the sensitivity as a sensor is. Therefore, it is more preferred as a characteristic of an optical filter having near-infrared transmittance. Abs(900-1400) / Abs(λ max ) is preferably 0.25 or less, more preferably 0.20 or less, and further preferably 0.16 or less. Abs(900-1400) / Abs(λ max ) can be, for example, greater than or equal to 0.01 or greater than or equal to 0.03.

[0258] <Method for producing colored resin composition>

[0259] The colored resin composition of the present embodiment can be prepared by mixing, for example, a colorant (A), a resin (B), a solvent (E), and, if necessary, a polymerizable compound (C), a polymerization initiator (D), a leveling agent (F), a polymerization initiation aid (D1), and other components.

[0260] The colorant (A) can be prepared as a coloring dispersion or a pigment dispersion containing the colorant (A1). For example, the remaining components can be mixed into the coloring dispersion or the pigment dispersion so as to have a predetermined concentration, thereby preparing the target colored resin composition.

[0261] When the colored resin composition contains a dye as the colorant (A2), the dye may be dissolved in part or all of the solvent (E) to prepare a solution. The solution is preferably filtered through a filter having a pore size of about 0.01 to 1 μm.

[0262] It is preferred that the colored resin composition be filtered through a filter having a pore size of about 0.01 to 10 μm after mixing the components.

[0263] [Optical filter and method of manufacturing the same]

[0264] As a method for manufacturing a colored pattern by the colored resin composition of the present embodiment, photolithography, inkjet method, printing method, etc. can be cited. Among them, the method for manufacturing a colored pattern is preferably photolithography. Photolithography is the following method: the colored resin composition is applied to a substrate, dried to form a colored coating film, the colored coating film is exposed across a photomask, and developed. In the photolithography, by not using a photomask and / or not developing during exposure, a colored cured coating film as a cured product of the colored coating film can be formed. The colored pattern or colored cured coating film so formed is an optical filter of the present embodiment.

[0265] The film thickness of the produced optical filter is not particularly limited and can be appropriately adjusted according to the purpose and application, etc. The film thickness of the optical filter can be, for example, 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably 0.5 to 6 μm.

[0266] Examples of the substrate include glass plates such as quartz glass, borosilicate glass, aluminosilicate glass, and soda-lime glass coated with silicon dioxide; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; silicon substrates; substrates formed with thin films of aluminum, silver, silver / copper / palladium alloy, etc. on these substrates, etc. Other optical filters (colored patterns or colored cured coatings), resin films, transistors, circuits, etc. may also be formed on these substrates.

[0267] The formation of each color pixel by photolithography can be performed by a known or commonly used device, condition, etc. The formation of each color pixel by photolithography can be performed, for example, in the following manner.

[0268] First, a colored resin composition is applied onto a substrate, and volatile components such as a solvent are removed by heat drying (prebaking) and / or reduced pressure drying, followed by drying to obtain a smooth colored coating film.

[0269] As the coating method, spin coating, slit coating, slit and spin coating, etc. can be mentioned. The temperature in the case of heating and drying is preferably 30 to 120°C, more preferably 50 to 110°C. In addition, the heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes. When reduced pressure drying is performed, it is preferably carried out under a pressure of 50 to 150 Pa and in a temperature range of 20 to 25°C.

[0270] The film thickness of the colored coating film is not particularly limited and can be appropriately selected depending on the film thickness of the target optical filter.

[0271] Next, the colored coating film is exposed through a photomask for forming a target colored pattern. The pattern on the photomask is not particularly limited, and a pattern according to the target application can be used.

[0272] The light source used in the exposure is preferably a light source that generates light with a wavelength of 250 to 450 nm. The light source used in the exposure may be, for example, a light source that cuts off light less than 350 nm using a filter that cuts off the wavelength region, or a light source that selectively extracts light near 436 nm, near 408 nm, and near 365 nm using a bandpass filter that extracts these wavelength regions. Specific examples of the light source used in the exposure include mercury lamps, light emitting diodes, metal halide lamps, halogen lamps, and the like.

[0273] During exposure, it is preferable to use an exposure device such as a mask aligner or a stepper in order to uniformly irradiate the entire exposure surface with parallel light and accurately align the photomask and the substrate on which the colored coating film is formed.

[0274] The colored coating film (i.e., the colored cured coating film) after exposure is brought into contact with a developer to form a colored pattern on the substrate. By developing, the unexposed portion of the colored composition layer is dissolved in the developer and removed. As the developer, for example, aqueous solutions of alkaline compounds such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide can be cited. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. The developer may further contain a surfactant.

[0275] As a developing method, a spinning immersion method, an immersion method, a spray method, etc. can be cited. During development, the substrate can be tilted at any angle. In addition, after development, it is preferred that the obtained colored pattern is washed with water.

[0276] The obtained colored pattern is preferably post-baked. The post-baking temperature is preferably 150 to 250° C., more preferably 160 to 235° C. The post-baking time is preferably 1 to 120 minutes, more preferably 10 to 60 minutes.

[0277] [Solid-state imaging device]

[0278] The solid-state imaging device of the present embodiment includes an optical filter, and the optical filter is a colored pattern, a colored cured coating film, or the like.

[0279] The colored resin composition of this embodiment can produce, for example, an infrared transmission filter, which is useful as a film used in display devices (eg, liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging devices.

[0280] Example

[0281] Hereinafter, the present invention will be described in more detail by giving examples, but the present invention is not limited to the following examples at all, and can certainly be appropriately changed and implemented within the scope that can be suitable for the above-mentioned and following purports, and they are all included in the technical scope of the present invention. It should be noted that, hereinafter, as long as there is no special explanation, "part" means "part by mass", and "%" means "% by mass".

[0282] In the following examples, the structures of the compounds were confirmed using a mass spectrometer (LC: Model 1200 manufactured by Agilent, MASS: Model LC / MSD6130 manufactured by Agilent).

[0283] In the following Examples, the absorbance and the maximum absorption wavelength were confirmed using an ultraviolet-visible-near-infrared absorption spectrometer (V-770 manufactured by JASCO Corporation, slit width: 1 nm).

[0284] The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by the GPC method under the following conditions.

[0285] Equipment: HLC-8120GPC (manufactured by Tosoh Corporation)

[0286] Column: TSK-GELG2000HXL

[0287] Column temperature: 40°C

[0288] Solvent: Tetrahydrofuran

[0289] Flow rate: 1.0mL / min

[0290] Solid content concentration of the analysis sample: 0.001 to 0.01 mass%

[0291] Injection volume: 50μL

[0292] Detector: RI

[0293] Calibration standard substances: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)

[0294] The ratio of the weight average molecular weight and the number average molecular weight (Mw / Mn) obtained above in terms of polystyrene conversion was defined as the degree of dispersion.

[0295] (Synthesis example 1)

[0296] <Preparation of Compound (Ia)>

[0297] Under nitrogen atmosphere, 48 parts of 3,6-dihydroxyphthalonitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), 96 parts of dehydrated pyridine (manufactured by Kanto Chemical Co., Ltd.) and 1296 parts of dichloromethane (dehydrated product manufactured by Kanto Chemical Co., Ltd.) were mixed and cooled to -78°C in a dry ice-acetone bath. 211 parts of trifluoromethanesulfonic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) were added dropwise over 30 minutes so that the temperature in the system did not rise from -50°C. After the addition was completed, the dry ice-acetone bath was removed, and the temperature was adjusted to room temperature (18 to 24°C), and then stirred at the temperature for 22 hours. The reaction solution was poured into 600 parts of pure water and a liquid separation operation was performed. The obtained organic layer was washed with 1000 parts of 1M hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.), 1000 parts of ion exchange water and 1000 parts of saturated saline in this order, and then dehydrated with anhydrous sodium sulfate (manufactured by Kanto Chemical Co., Ltd.). After filtering the sodium sulfate, the solvent was distilled off and the crude product was recrystallized from dichloromethane to obtain 53 parts (yield 42%) of the compound represented by formula (Ia) as colorless crystals.

[0298] [Chemical formula 7]

[0299]

[0300] <Identification of Compound (Ia)>

[0301] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 425

[0302] Exact mass: 424

[0303] (Synthesis example 2)

[0304] <Preparation of Compound (Ib)>

[0305] Under a nitrogen atmosphere, 42 parts of the compound (Ia) prepared in Synthesis Example 1, 57 parts of potassium carbonate (manufactured by Kanto Chemical Co., Ltd.) and 819 parts of dimethyl sulfoxide (dehydrated product manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 23°C for 18 hours. While the obtained mixture was kept below 40°C, 22 parts of thiophenol (manufactured by Tokyo Chemical Industry Co., Ltd.) were added dropwise over 30 minutes. After the addition was completed, the mixture was stirred at room temperature (18-24°C) for 19 hours. After the reaction was completed, the reaction solution was injected into 15,000 parts of pure water, and liquid-liquid extraction was performed three times using 5,000 parts of dichloromethane. The organic layer obtained by separation was dehydrated using anhydrous sodium sulfate (manufactured by Kanto Chemical Co., Ltd.), and after filtering the sodium sulfate, the solvent was distilled off. The crude product was purified by silica gel column chromatography (developing solvent: chloroform) to obtain 17 parts of the compound represented by formula (Ib) as pale yellow crystals (yield: 51%).

[0306] [Chemical formula 8]

[0307]

[0308] <Identification of Compound (Ib)>

[0309] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 345

[0310] Exact mass: 344

[0311] (Synthesis example 3)

[0312] <Preparation of Compound (I-1)>

[0313] Under a nitrogen atmosphere, 8.6 parts of the compound (Ib) prepared in Synthesis Example 2, 0.81 parts of nickel (II) chloride (manufactured by FUJIFILM WakoPure Chemical Corporation), 808 parts of 1-pentanol (manufactured by Tokyo Chemical Industry Co., Ltd.), and 20 parts of 1,8-diazabicyclo[5,4,0]-7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed and refluxed at 160°C for 7 hours. After the reaction was completed, the reaction solution was cooled to room temperature (18-24°C) and injected into 8000 parts of methanol. The precipitated solid was washed twice with 200 parts of ion exchange water and twice with 200 parts of methanol by decantation. The crude product was purified by silica gel column chromatography (developing solvent: chloroform) to obtain 4.9 parts of compound (I-1) represented by formula (I-1) in the form of a solid (yield of 55%).

[0314] [Chemical formula 9]

[0315]

[0316] <Identification of Compound (I-1)>

[0317] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 1435

[0318] Exact mass: 1434

[0319] (Synthesis Example 4)

[0320] <Preparation of Compound (II-a)>

[0321] Under a nitrogen atmosphere, 10 parts of 2,3-dichloro-5,6-dicyano-p-benzoquinone (manufactured by Tokyo Chemical Industry Co., Ltd.), 13 parts of sodium dithionite (manufactured by FUJIFILM Wako Pure Chemical Corporation), 170 parts of ion exchange water and 170 parts of toluene (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at room temperature (18-24°C) for 1 hour. After the reaction was completed, the precipitated solid was filtered, washed with 30 parts of ice-cooled ion exchange water, and further washed with 30 parts of n-hexane. The crude product was recrystallized using acetone / water, and as a result, 7.0 parts (yield of 70%) of the compound represented by formula (II-a) were obtained as colorless crystals.

[0322] [Chemical formula 10]

[0323]

[0324] <Identification of Compound (II-a)>

[0325] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 229

[0326] Exact mass: 228

[0327] (Synthesis Example 5)

[0328] <Preparation of Compound (II-b)>

[0329] Under a nitrogen atmosphere, 30 parts of the compound (II-a) obtained in Synthesis Example 4, 54 parts of 1-bromobutane (manufactured by Tokyo Chemical Industry Co., Ltd.), 109 parts of potassium carbonate (manufactured by Kanto Chemical Industry Co., Ltd.), 43 parts of potassium iodide (manufactured by Kanto Chemical Industry Co., Ltd.) and 669 parts of N,N-dimethylformamide (dehydrated product manufactured by Kanto Chemical Industry Co., Ltd.) were mixed and stirred at 80°C for 3 hours. After the reaction was completed, it was cooled to room temperature (18-24°C) and filtered using diatomaceous earth. It was washed with 3000 parts of ethyl acetate, and 1300 parts of ion exchange water was added to the obtained filtrate to perform a liquid separation operation. The obtained organic layer was dehydrated with anhydrous sodium sulfate (manufactured by Kanto Chemical Industry Co., Ltd.), and after filtering the sodium sulfate, the solvent was distilled off. The crude product was purified by silica gel column chromatography (developing solvent: hexane / chloroform = 1 / 1 (volume / volume)) to obtain 33 parts of the compound represented by formula (II-b) (yield: 75%).

[0330] [Chemical formula 11]

[0331]

[0332] <Identification of Compound (II-b)>

[0333] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 348

[0334] Exact mass: 347

[0335] (Synthesis Example 6)

[0336] <Preparation of Compound (II-c)>

[0337] Under a nitrogen atmosphere, 18 parts of potassium hydroxide (manufactured by Kanto Chemical Co., Ltd.), 36 parts of thiophenol (manufactured by Tokyo Chemical Industry Co., Ltd.) and 78 parts of ion-exchanged water were mixed. A solution formed by 50 parts of compound (II-b) obtained in Synthesis Example 5 and 588 parts of acetone (dehydrated product manufactured by Kanto Chemical Co., Ltd.) was added at 40°C over 30 minutes, and the mixture was stirred at 60°C for 2 hours. 2000 parts of ethyl acetate and 1000 parts of ion-exchanged water were added to perform a liquid separation operation. The obtained organic layer was dehydrated using anhydrous sodium sulfate (manufactured by Kanto Chemical Co., Ltd.), the sodium sulfate was filtered, and the solvent was distilled off. The crude product was purified using silica gel column chromatography (developing solvent: chloroform) to obtain 59 parts of the compound represented by formula (II-c) (yield: 83%).

[0338] [Chemical formula 12]

[0339]

[0340] <Identification of Compound (II-c)>

[0341] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 489

[0342] Exact mass: 488

[0343] (Synthesis Example 7)

[0344] <Preparation of Compound (II-d)>

[0345] 68 parts of compound (II-d) were obtained in the same manner as in Synthesis Example 6 except that 45 parts of 4-methoxythiophenol (Tokyo Chemical Industry Co., Ltd.) was used instead of 36 parts of thiophenol (Tokyo Chemical Industry Co., Ltd.).

[0346] [Chemical formula 13]

[0347]

[0348] (Synthesis Example 8)

[0349] <Preparation of Compound (II-1)>

[0350] Under a nitrogen atmosphere, 8.6 parts of the compound (II-c) prepared in Synthesis Example 6, 0.57 parts of nickel (II) chloride (manufactured by FUJIFILM Wako Pure Chemical Corporation), 808 parts of 1-pentanol (manufactured by Tokyo Chemical Industry Co., Ltd.), and 141 parts of 1,8-diazabicyclo [5,4,0] -7-undecene (manufactured by Tokyo Chemical Industry Co., Ltd.) were mixed and refluxed at 160°C for 15 hours. After the reaction was completed, the reaction solution was cooled to room temperature (18-24°C) and injected into 8000 parts of methanol. The precipitated solid was washed twice with 200 parts of ion exchange water and twice with 200 parts of methanol by decantation. The crude product was purified by silica gel column chromatography (developing solvent: chloroform) to obtain 5.3 parts of compound (II-1) represented by formula (II-1) in the form of a solid (yield of 59%).

[0351] [Chemical formula 14]

[0352]

[0353] <Identification of Compound (II-1)>

[0354] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 2011

[0355] Exact quality: 2010

[0356] (Synthesis Example 9)

[0357] <Preparation of Compound (II-2)>

[0358] Except for replacing 8.6 parts of compound (II-c) with 45 parts of 9.6 parts of compound (II-d) obtained in Synthesis Example 7 (manufactured by Tokyo Chemical Industry Co., Ltd.), the same operation was carried out as in Synthesis Example 8 to obtain 4.4 parts of compound (II-2) represented by formula (II-2) in the form of a solid (yield 50%).

[0359] [Chemical formula 15]

[0360]

[0361] <Identification of Compound (II-2)>

[0362] (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 2235

[0363] Exact mass: 2234

[0364] (Synthesis Example 10)

[0365] <Preparation of Resin (B-1)>

[0366] A suitable amount of nitrogen was passed through a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen, and 340 parts of propylene glycol monomethyl ether acetate was added, and heated to 80° C. while stirring. Then, 57 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decane-8-yl ester and 3,4-epoxytricyclo[5.2.1.0 2,6 ] A mixed solution of 54 parts of a mixture of decane-9-yl ester (containing a molar ratio of 1:1), 239 parts of benzyl methacrylate, and 73 parts of propylene glycol monomethyl ether acetate. On the other hand, an initiator solution obtained by dissolving 40 parts of a polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) in 197 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition of the initiator solution was completed, it was kept at 80°C for 3 hours and then cooled to room temperature (18-24°C) to obtain a copolymer (resin (B-1)) solution having a viscosity of 127 mPa·s and a solid content of 37.0% as measured by a B-type viscometer (23°C). The weight average molecular weight Mw of the resulting copolymer is 9.4×10 3 , the dispersion degree was 1.89, and the acid value converted to solid content was 114 mg-KOH / g. Resin (B-1) has the following structural units.

[0367] [Chemical formula 16]

[0368]

[0369] (Comparative Synthesis Example)

[0370] According to the synthesis method described in Example 1 of JP-A-2014-19838, a phthalocyanine compound Pc-02 was obtained.

[0371] [Chemical formula 17]

[0372]

[0373] <Example 1>

[0374] (1) Preparation of Colored Resin Composition 1A

[0375] 30 parts of compound (I-1) as a colorant (A), 24 parts of a dispersant (BYK LPN-6919 manufactured by BYK) (calculated as solid content), 24 parts of the resin (B-1) obtained in Synthesis Example 10 as a resin (B) (calculated as solid content), 522 parts of propylene glycol monomethyl ether acetate as a solvent (E) and 900 parts of 0.2 mm zirconium oxide beads were mixed, and the obtained mixture was shaken for 1 hour using a paint conditioner (manufactured by LAU). Then, the zirconium oxide beads were removed by filtration to obtain a colored resin composition 1A.

[0376] (2) Ultraviolet-visible-near-infrared absorption spectrometry of colorant (A)

[0377] The colored resin composition 1A was diluted with propylene glycol monomethyl ether acetate so that the content of the compound (I-1) in the colored resin composition 1A was 10 mass ppm, and a measurement solution was prepared. The measurement solution prepared in this way was placed in a 1 cm square quartz cuvette, and the measurement was performed in the wavelength range of 1400 to 300 nm (data collection interval 1 nm) using an ultraviolet visible near infrared absorption spectrometer. At this time, the wavelength showing the maximum absorbance was taken as the maximum absorption wavelength λ max In addition, calculate the absorbance Abs(780) at a wavelength of 780nm and λ max The absorbance Abs(λ max ) ratio (Abs(780) / Abs(λ max )). The optical filter needs to absorb light of 780nm, which is the upper limit of the visible region. Therefore, the larger the value, the more preferable it is as a characteristic of an optical filter having near-infrared transmittance. In addition, the maximum absorbance Abs(900-1400) and λ in the wavelength range of 900 to 1400nm are calculated. max The absorbance Abs(λ max ) ratio (Abs(900-1400) / Abs(λmax )). The smaller the value, the higher the transmittance in the near-infrared region, and the higher the sensitivity as a sensor, and therefore, the more preferable it is as a characteristic of an optical filter having near-infrared transmittance.

[0378] (3) Preparation of Colored Resin Composition 1B

[0379] The following components were mixed to obtain a colored resin composition 1B.

[0380] Colored resin composition 1A: 720 parts

[0381] (Colorant (A): Compound (I-1) 36 parts

[0382] Resin (B): Resin (B-1) (converted to solid content) 28.8 parts

[0383] Solvent (E): 626 parts of propylene glycol monomethyl ether acetate

[0384] Other ingredients: dispersant (BYK LPN-6919, manufactured by BYK) (calculated as solid content) 28.8 parts)

[0385] Resin (B): 73 parts of the resin (B-1) obtained in Synthesis Example 10 (calculated on a solid basis)

[0386] · Polymerizable compound (C): 68 parts of dipentaerythritol polyacrylate (trade name A-9550, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) (calculated on a solid basis)

[0387] Polymerization initiator (D): 5.1 parts of N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-one-2-imine (trade name TR-PBG327, manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.)

[0388] Solvent (E): 1134 parts of propylene glycol monomethyl ether acetate

[0389] Leveling agent (F): 1.4 parts of polyether-modified silicone oil (trade name: TORAY SILICONE SH 8400, manufactured by Dow Corning Toray Co., Ltd.)

[0390] (4) Preparation of colored cured coating film

[0391] The colored resin composition 1B was applied on a 5 cm square glass substrate (Eagle 2000, manufactured by Corning) by spin coating to obtain a colored coating film. The colored coating film was then pre-baked at 100°C for 3 minutes and post-baked in an oven at 230°C for 20 minutes to obtain a colored cured coating film.

[0392] (5) Heat resistance test

[0393] In an oven, under an atmospheric atmosphere, the obtained colored cured coating film was heated at 260°C for 10 minutes, and the absorbance maintenance rate of the colored cured coating film before and after heating was measured. Here, the so-called absorbance maintenance rate is a value calculated by the following formula, and the higher the absorbance maintenance rate, the better the heat resistance. In addition, if the heat resistance of the colored cured coating film is good, it can be said that the heat resistance of the optical filter made from the same colored resin composition is also excellent. The results are shown in Table 1.

[0394] Absorbance maintenance rate (%) = (absorbance at the maximum absorption wavelength of the colored cured coating film after heating) / (absorbance at the maximum absorption wavelength of the colored cured coating film before heating) × 100

[0395] (6) Light resistance test

[0396] An ultraviolet cutoff filter (COLORED OPTICAL GLASSL38, manufactured by Hoya, a filter that cuts off light below 380nm) was configured on the obtained colored cured coating film, and a xenon lamp was irradiated for 68 hours using a light resistance tester (SUNTEST CPS+, manufactured by Toyo Seiki Seisakusho, Ltd.), and the absorbance maintenance rate of the colored cured coating film before and after irradiation was measured. Here, the so-called absorbance maintenance rate is a value calculated by the following formula, and the higher the absorbance maintenance rate, the better the light resistance. In addition, if the light resistance of the colored cured coating film is good, it can be said that the light resistance of the optical filter made from the same colored resin composition is also excellent. The results are shown in Table 1.

[0397] Absorbance maintenance rate (%) = (absorbance at the maximum absorption wavelength of the colored cured coating film after irradiation) / (absorbance at the maximum absorption wavelength of the colored cured coating film before irradiation) × 100

[0398] <Example 2>

[0399] Except that 30 parts of compound (I-1) was replaced with 30 parts of compound (II-1), the same operation as in Example 1 was performed to obtain a colored resin composition 2A and a colored resin composition 2B, and a colored cured coating film was prepared. For the colored resin composition 2A and the colored cured coating film, ultraviolet visible near infrared absorption spectrometry, heat resistance test and light resistance test were performed in the same manner as in Example 1. The results are shown in Table 1.

[0400] <Example 3>

[0401] Except that 30 parts of compound (I-1) was replaced with 30 parts of compound (II-2), the same operation as in Example 1 was performed to obtain colored resin composition 3A and colored resin composition 3B, and a colored cured coating film was prepared. For the colored resin composition 3A and the colored cured coating film, ultraviolet visible near infrared absorption spectrometry, heat resistance test and light resistance test were performed in the same manner as in Example 1. The results are shown in Table 1.

[0402] <Example 4>

[0403] Except that 15 parts of compound (I-1) and 15 parts of compound (II-1) were used instead of 30 parts of compound (I-1), the same operation as in Example 1 was performed to obtain colored resin composition 4A and colored resin composition 4B, and a colored cured coating film was prepared. For the colored resin composition 4A and the colored cured coating film, ultraviolet visible near infrared absorption spectrometry, heat resistance test and light resistance test were performed in the same manner as in Example 1. The results are shown in Table 1.

[0404] <Example 5>

[0405] The same operation as in Example 1 was performed except that 6 parts of the compound (I-1) and 24 parts of the compound (II-1) were used instead of 30 parts of the compound (I-1) to obtain a colored resin composition 5A and a colored resin composition 5B, and a colored cured coating film was prepared. For the colored resin composition 5A and the colored cured coating film, ultraviolet-visible-near-infrared absorption spectrometry, heat resistance test, and light resistance test were performed in the same manner as in Example 1. The results are shown in Table 1.

[0406] <Example 6>

[0407] The same operation as in Example 1 was performed except that 10 parts of the compound (I-1) and 20 parts of the compound (II-1) were used instead of 30 parts of the compound (I-1) to obtain a colored resin composition 6A and a colored resin composition 6B, and a colored cured coating film was prepared. For the colored resin composition 6A and the colored cured coating film, ultraviolet-visible-near-infrared absorption spectrometry, heat resistance test, and light resistance test were performed in the same manner as in Example 1. The results are shown in Table 1.

[0408] <Example 7>

[0409] The same operation as in Example 1 was performed except that 20 parts of the compound (I-1) and 10 parts of the compound (II-1) were used instead of 30 parts of the compound (I-1) to obtain the colored resin composition 7A and the colored resin composition 7B, and a colored cured coating film was prepared. The colored resin composition 7A and the colored cured coating film were subjected to ultraviolet-visible-near infrared absorption spectrometry, a heat resistance test, and a light resistance test in the same manner as in Example 1. The results are shown in Table 1.

[0410] <Comparative Example 1>

[0411] The same operation as in Example 1 was performed except that 30 parts of the phthalocyanine compound Pc-02 was used instead of 30 parts of the compound (I-1) to obtain a colored resin composition 1a and a colored resin composition 1b, and a colored cured coating film was prepared. The colored resin composition 1a and the colored cured coating film were subjected to ultraviolet-visible-near infrared absorption spectrometry, a heat resistance test, and a light resistance test in the same manner as in Example 1. The results are shown in Table 1.

[0412] [Table 1]

[0413]

[0414] As shown in Table 1, the colored cured coating films of Examples 1 to 7 containing a predetermined colorant were superior in heat resistance and light resistance to the colored cured coating film of Comparative Example 1 not containing a predetermined colorant. These results confirmed that the colored resin composition of the present invention can form an optical filter having excellent heat resistance.

Claims

1. A colored resin composition comprising a colorant, an alkali-soluble resin and a solvent, The colorant comprises at least one selected from the group consisting of compounds represented by formula (I) and formula (II), The colored resin composition has a maximum absorption wavelength of 799 nm or less in the wavelength range of 380 to 1400 nm, [Chemical formula 1] In formula (I), M 1 represents a divalent metal atom; R 1 ~R 8 Each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms, or OR 17 Group; R 17 represents a hydrocarbon group having 1 to 20 carbon atoms, in the presence of two or more R 17 In the case of , they may be the same or different from each other; A 1 ~A 8 Each independently represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms; [Chemical formula 2] In formula (II), M 2 represents a divalent metal atom; R 9 ~R 16 Each independently represents a saturated hydrocarbon group having 1 to 10 carbon atoms; A 9 ~A 16 Each independently represents an aryl group having 6 to 20 carbon atoms or a heteroaryl group having 3 to 20 carbon atoms.

2. The colored resin composition according to claim 1, wherein M of the formula (I) 1 And M of the formula (II) 2 At least one of them is a nickel atom.

3. The colored resin composition according to claim 1 or 2, wherein R of formula (I) 1 ~R 8 A hydrogen atom. 4 . The colored resin composition according to claim 1 , further comprising at least one of a polymerizable compound and a polymerization initiator. 5 . An optical filter formed from the colored resin composition according to claim 1 . 6 . A solid-state imaging device comprising the optical filter according to claim 5 .

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