Coloring Curing Resin Composition

Abstract

The objective of this invention is to provide a color-curable resin composition for optical filters that produces fewer foreign matter. This invention relates to a color-curable resin composition comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator, wherein the colorant is a colorant comprising a compound represented by formula (I) or formula (II).

Description

Technical Field

[0001] This invention relates to color-curable resin compositions, optical filters, and solid-state imaging devices. Background Technology

[0002] Optical filters used in display devices such as liquid crystal displays, electroluminescent displays, and plasma displays, as well as solid-state imaging devices such as CCDs and CMOS sensors, are manufactured from color-curable resin compositions. As such color-curable resin compositions, compositions containing phthalocyanine compounds as colorants are known (Patent Document 1). Patent Document 1 describes that the above-mentioned compositions can absorb near-infrared light to form fine patterns.

[0003] Existing technical documents

[0004] Patent documents

[0005] Patent Document 1: Japanese Patent Application Publication No. 2010-160380 Summary of the Invention

[0006] The problem that the invention aims to solve

[0007] The objective of this invention is to provide a coloring and curing resin composition for optical filters that produces fewer foreign matter.

[0008] Methods for solving problems

[0009] This invention includes the following inventions.

[0010] A coloring and curing resin composition comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator.

[0011] The colorant is a colorant containing a compound represented by formula (I) or formula (II).

[0012]

[0013] In formula (I), X 1 and X 2 Each independently represents a hydrogen atom, SR 1 or NR 2 R 3 .

[0014] Y 1 and Y 2 Each independently represents a hydrogen atom, OR 1 , or SR 1 .

[0015] R 1It represents an aryl group with 6 to 20 carbon atoms or a heteroaryl group with 3 to 20 carbon atoms, wherein the hydrogen atoms contained in the aryl group and the heteroaryl group can be substituted by halogen atoms or alkoxy groups with 1 to 20 carbon atoms.

[0016] R 2 and R 3 Each independently represents an alkyl group having 1 to 10 hydrogen atoms or carbon atoms, wherein the methylene group contained in the alkyl group may be replaced by an oxygen atom, R 2 With R 3 They can bond together to form a ring containing nitrogen atoms.

[0017] There are multiple X's in one molecule. 1 X 2 Y 1 Y 2 R 1 R 2 or R 3 In this case, they can be the same or different.

[0018] M 1 It represents a hydrogen atom, a monovalent metal atom, a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, or an oxide metal atom.

[0019] M 1 When the atom is a hydrogen atom or a monovalent metal atom, m is 2, M 1 When the atom is a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, or an oxidized metal atom, m is 1.

[0020] *a, *a1, *a2, *b, *b1, *b2, *c1, and *c2 all represent chemical bonds. One of the two *a bonds is bonded to *a1, and the other to *a2. One of the two *b bonds is bonded to *b1, and the other to *b2. *c1 and *c2 are bonded to M. 1 Bonding.

[0021]

[0022] In formula (II), Z 1 and Z 2 Each can be independently represented by an oxygen atom, a sulfur atom, or NR. 4 .

[0023] R 4 An alkyl group having 1 to 10 hydrogen or carbon atoms, wherein the methylene group may be replaced with an oxygen atom.

[0024] Ar 1It represents an arylene with 6 to 20 carbon atoms or a heteroarylene with 3 to 20 carbon atoms, wherein the hydrogen atoms contained in the arylene and heteroarylene can be replaced by halogen atoms or alkoxy groups with 1 to 20 carbon atoms.

[0025] Z 3 and Z 4 Each independently represents a hydrogen atom, N(R) 6 2. OR 5 or SR 5 .

[0026] R 5 The alkyl group represents an alkyl group with 1 to 20 carbon atoms, an aryl group with 6 to 20 carbon atoms, or a heteroaryl group with 3 to 20 carbon atoms. The hydrogen atom contained in the alkyl group may be replaced by a halogen atom, the methylene group contained in the alkyl group may be replaced by an oxygen atom, and the hydrogen atom contained in the aryl group and the heteroaryl group may be replaced by a halogen atom or an alkoxy group with 1 to 20 carbon atoms.

[0027] R 6 It represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms (the hydrogen atom contained in the alkyl group can be replaced by an aryl group having 6 to 10 carbon atoms, and the methylene group contained in the alkyl group can be replaced by an oxygen atom).

[0028] There are multiple Z in one molecule. 1 Z 2 Z 3 Z 4 Ar 1 R 4 R 5 or R 6 In this case, they can be the same or different.

[0029] M 2 It represents a hydrogen atom, a monovalent metal atom, a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, or an oxide metal atom.

[0030] M 2 When n is a hydrogen atom or a monovalent metal atom, n is 2, and M is 2. 2 When the atom is a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, or an oxidized metal atom, n is 1.

[0031] *d, *d1, *d2, *e, *e1, *e2, *f1, and *f2 all represent chemical bonds. One of the two *d bonds is bonded to *d1, and the other to *d2. One of the two *e bonds is bonded to *e1, and the other to *e2. *f1 and *f2 are bonded to M. 2 Bonding.

[0032] [2] The coloring curable resin composition as described in [1], wherein the resin is a copolymer comprising a structural unit selected 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 olefinic unsaturated bond.

[0033] [3] An optical filter formed from the coloring and curing resin composition described in [1] or [2].

[0034] [4] A solid-state imaging device comprising the optical filter described in [3].

[0035] Invention Effects

[0036] The coloring and curing resin composition according to the present invention is less prone to generating foreign matter when forming optical filters. Detailed Implementation

[0037] The coloring curable resin composition of the present invention comprises a colorant (hereinafter, sometimes referred to as colorant (A)), a resin (hereinafter, sometimes referred to as resin (B)), a polymerizable compound (hereinafter, sometimes referred to as polymerizable compound (C)), and a polymerization initiator (hereinafter, sometimes referred to as polymerization initiator (D)).

[0038] The coloring and curing resin composition of the present invention preferably further comprises a solvent (hereinafter, sometimes referred to as solvent (E)).

[0039] The coloring and curing resin composition of the present invention may contain a leveling agent (hereinafter, sometimes referred to as leveling agent (F)).

[0040] Unless otherwise specified, the compounds used as examples of ingredients in this specification may be used alone or in combination.

[0041] Colorant (A)

[0042] Colorant (A) comprises a compound represented by formula (I) or (II) as a phthalocyanine compound (also called colorant (A1)). This compound is preferably a compound having a maximum absorption wavelength in the near-infrared region (wavelength 700–2500 nm, preferably 700–1500 nm, more preferably 700–1300 nm). The compound represented by formula (I) is described below.

[0043]

[0044] In formula (I), X 1 and X 2 Each independently represents a hydrogen atom, SR 1 or NR 2 R 3 .

[0045] Y 1 and Y 2 Each independently represents a hydrogen atom, OR 1 , or SR 1 .

[0046] R 1 It represents an aryl group with 6 to 20 carbon atoms or a heteroaryl group with 3 to 20 carbon atoms, wherein the hydrogen atoms contained in the aryl group and the heteroaryl group can be substituted by halogen atoms or alkoxy groups with 1 to 20 carbon atoms.

[0047] R 2 and R 3 Each independently represents an alkyl group having 1 to 10 hydrogen atoms or carbon atoms, wherein the methylene group contained in the alkyl group may be replaced by an oxygen atom, R 2 With R 3 They can bond together to form a ring containing nitrogen atoms.

[0048] There are multiple X's in one molecule. 1 X 2 Y 1 Y 2 R 1 R 2 or R 3 In this case, they can be the same or different.

[0049] M 1 It represents a hydrogen atom, a monovalent metal atom, a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, or an oxide metal atom.

[0050] M 1 When the atom is a hydrogen atom or a monovalent metal atom, m is 2, M 1 When the atom is a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, or an oxidized metal atom, m is 1.

[0051] *a, *a1, *a2, *b, *b1, *b2, *c1, and *c2 all represent chemical bonds. One of the two *a bonds is bonded to *a1, and the other to *a2. One of the two *b bonds is bonded to *b1, and the other to *b2. *c1 and *c2 are bonded to M. 1 Bonding.

[0052] As R 1The aryl group can be, for example, a monocyclic or polycyclic (e.g., 2- or 3-cyclic) aryl group. Specifically, examples 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) ... (tert-butyl)-4-methylphenyl, 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, phenanthryl, anthraceneyl, 2-dodecylphenyl, 3-dodecylphenyl, 4-dodecylphenyl, phenanthryl, fluorenyl, biphenyl, etc. The aryl group preferably has 6 to 18 carbon atoms, more preferably 6 to 15, and even more preferably 6 to 12.

[0053] As R 1 The heteroaryl group represented can be, for example, a monocyclic or polycyclic (e.g., 2- or 3-cyclic) heteroaryl group. Specifically, examples include furanyl, benzofuranyl, pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, thiopheneyl, benzothiopheneyl, oxazolyl, benzooxazolyl, thiazolyl, benzothiazolyl, indolyl, carbazoleyl, acridineyl, imidazolyl, benzimidazolyl, quinolinyl, isoquinolinyl, etc. 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.

[0054] In addition, the number of elements constituting the heteroaryl ring is preferably 5 to 10.

[0055] The halogen atom that can be substituted with the hydrogen atom contained in the aryl group and the heteroaryl group is preferably a chlorine atom, a bromine atom, a fluorine atom, or an iodine atom.

[0056] Examples of alkoxy groups that can be substituted with hydrogen atoms contained in the aryl group and the heteroaryl group 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, heptadecanyloxy, octadecyloxy, and nonadecanyloxy.

[0057] The number of carbon atoms in the alkoxy group is preferably 1 to 18, more preferably 1 to 15, even more preferably 1 to 10, and even more preferably 1 to 8.

[0058] As R 2 and R 3 Examples of alkyl groups that can be represented include:

[0059] Straight-chain alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, and decyl;

[0060] Isopropyl, Isobutyl, sec-butyl, tert-butyl, 2-ethylbutyl, 3,3-dimethylbutyl, 1,1,3,3-tetramethylbutyl, 1-methylbutyl, 1-ethylpropyl, 3-methylbutyl, neopentyl, 1,1-dimethylpropyl, 2-methylpentyl, 3-ethylpentyl, 1,3-dimethylbutyl, 2-propylpentyl, 1-ethyl-1,2-dimethylpropyl, 1-methylpentyl, 4-methylpentyl, 4 -Methylhexyl, 5-methylhexyl, 2-ethylhexyl, 1-methylhexyl, 1-ethylpentyl, 1-propylbutyl, 3-ethylheptyl, 2,2-dimethylheptyl, 1-methylheptyl, 1-ethylhexyl, 1-propylpentyl, 1-methyloctyl, 1-ethylheptyl, 1-propylhexyl, 1-butylpentyl, 1-methylnonyl, 1-ethyloctyl, 1-propylheptyl, and 1-butylhexyl, etc., are branched alkyl groups; etc. The alkyl group preferably has 1 to 8 carbon atoms, more preferably 1 to 6, and even more preferably 1 to 5.

[0061] The so-called R 2 and R 3 The group obtained by replacing the methylene group of an alkyl group with an oxygen atom is the group formed by replacing the methylene group of an alkyl group with an oxygen atom. The group obtained by replacing the methylene group of an alkyl group with an oxygen atom is preferably a group with 1 to 10 carbon atoms, more preferably a group with 1 to 6 carbon atoms (the methylene group before the oxygen atom is not included in the carbon atom number. For example, ethoxy has 2 carbon atoms). R 2 and R 3 The alkyl group represented is preferably a straight-chain alkyl group. Examples of such groups include those represented by the following formulas. In the following formulas, * represents a chemical bond.

[0062]

[0063] As R 2 With R 3 Examples of nitrogen-containing non-aromatic 4- to 7-membered rings that are bonded together include pyrrolidine rings, morpholine rings, piperidine rings, and piperazine rings.

[0064] X 1 and X 2SR 1 Preferably, it is an arylthioalkyl group with 6 to 20 carbon atoms or a heteroarylthioalkyl group with 3 to 20 carbon atoms.

[0065] As arylthioalkyl groups, examples include monocyclic and polycyclic (e.g., bicyclic or tricyclic) aryl groups bonded to sulfur atoms. Specifically, examples include phenylthioalkyl, naphthylthioalkyl, anthraceneylthioalkyl, pyreneylthioalkyl, o-tolylthioalkyl, p-tolylthioalkyl, 2,6-dimethylphenylthioalkyl, and 2,4,6-trimethylphenylthioalkyl. Groups formed by monocyclic or bicyclic aryl groups bonded to sulfur atoms are particularly preferred. Phenylthioalkyl and naphthylthioalkyl are particularly preferred. The number of carbon atoms in the arylthioalkyl group is preferably 6 to 18, more preferably 6 to 15, and even more preferably 6 to 12.

[0066] Examples of heteroarylthioalkyl groups include monocyclic and polycyclic (e.g., bicyclic or tricyclic) heteroaryl groups bonded to sulfur atoms. Specifically, examples include pyridyl, pyrimidinyl, indolyl, quinolinyl, benzimidazolyl, furanyl, thiophene, benzofuranyl, and 1,3,4-thiadiazolyl groups bonded to sulfur atoms. Groups formed by monocyclic or bicyclic heteroaryl groups bonded to sulfur atoms are particularly preferred. The number of carbon atoms in the heteroarylthioalkyl group is preferably 3 to 18, more preferably 3 to 12, and even more preferably 3 to 9.

[0067] As X 1 and X 2 NR 2 R 3 Examples of secondary or tertiary amino groups include n-propylamino, isopropylamino, n-butylamino, n-pentylamino, n-hexylamino, cyclohexylamino, n-heptylamino, n-octylamino, 2-ethylhexylamino, dimethylamino, diethylamino, dipropylamino, dibutylamino (di-n-butylamino), ethylbutylamino, di(2-ethylhexyl)amino, pyrrolylalkyl, piperidinyl, 4-methylpiperazinyl, morpholinoyl, etc. Preferably, the amino group is a secondary or tertiary amino group substituted with a straight chain of 1 to 8 carbon atoms, a branched chain of 3 to 8 carbon atoms, or a cyclic alkyl group of 3 to 8 carbon atoms. Particularly preferred are n-butylamino, 2-ethylhexylamino, dimethylamino, diethylamino, and dibutylamino.

[0068] As R 2 and R 3 Preferably, one of them is a hydrogen atom and the other is an alkyl group having 1 to 10 carbon atoms.

[0069] Y 1 and Y 2 OR 1Preferably, it is an aryloxy group with 6 to 20 carbon atoms or a heteroaryloxy group with 3 to 20 carbon atoms.

[0070] Examples of aryloxy groups include monocyclic and polycyclic (e.g., bicyclic or tricyclic) aryl groups bonded to oxygen atoms. Specifically, examples include phenoxy, o-tolyloxy, p-tolyloxy, 2,4,6-trimethylphenoxy, naphthoxy, anthraceneyloxy, phenanthroxy, fluorenyloxy, and pyreneyloxy. Groups formed by monocyclic or bicyclic aryl groups bonded to oxygen atoms are particularly preferred. Phenoxy, o-tolyloxy, 2,4,6-trimethylphenoxy, 1-naphthoxy (1-naphthyloxy), and 2-naphthoxy (2-naphthyloxy) are particularly preferred. The number of carbon atoms in the aryloxy group is preferably 6 to 18, more preferably 6 to 15, and even more preferably 6 to 12.

[0071] Examples of heteroaryloxy groups include monocyclic and polycyclic (e.g., bicyclic or tricyclic) heteroaryl groups bonded to an oxygen atom. Specifically, examples include pyridyl, pyrimidinyl, indolyl, quinolinyl, benzimidazolyl, furanyl, thiophene, benzofuranyl, and 1,3,4-thiadiazolyl groups bonded to an oxygen atom. Groups formed by monocyclic or bicyclic heteroaryl groups bonded to an oxygen atom are particularly preferred. The number of carbon atoms in the heteroaryloxy group is preferably 3 to 18, more preferably 3 to 12, and even more preferably 3 to 9.

[0072] Y 1 and Y 2 SR 1 Preferably, it is an arylthioalkyl group having 6 to 20 carbon atoms or a heteroarylthioalkyl group having 3 to 20 carbon atoms; examples include those related to X. 1 and X 2 The same group as the arylthioalkyl or heteroarylthioalkyl groups described herein.

[0073] M 1 It represents a hydrogen atom, a monovalent metal atom, a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, or an oxide metal atom.

[0074] Examples of monovalent metal atoms include Na, K, and Li.

[0075] Metal atoms that are divalent, trivalent, tetravalent, or contained within metal oxide atoms, for example, include metal atoms belonging to groups 3 to 15 of the periodic table. Specifically, examples of divalent metal atoms include Cu, Zn, Fe, Co, Ni, Ru, Pb, Rh, Pd, Pt, Mn, Sn, and Pb.

[0076] Examples of trivalent substituted metal atoms include Al-F, Al-Cl, Al-Br, Al-I, Al-OH, Ga-F, Ga-Cl, Ga-Br, Ga-I, In-F, In-Cl, In-Br, In-I, Tl-F, Tl-Cl, Tl-Br, Tl-I, Al-C6H5, Al-C6H4(CH3), In-C6H5, In-C6H4(CH3), Mn(OH), Mn(OC6H5), Mn[OSi(CH3)3], Fe-Cl, Ru-Cl, etc.

[0077] Examples of tetravalent substituted metal atoms include CrCl2, SiCl2, SiBr2, SiF2, SiI2, ZrCl2, ZrI2, GeCl2, GeBr2, GeF2, GeI2, SnCl2, SnF2, SnBr2, TiF2, TiCl2, TiBr2, Si(OH)2, Ge(OH)2, Zr(OH)2, Mn(OH)2, Sn(OH)2, and Ti(R). 10 2. Cr(R) 10 )2、Si(R 10 )2、Sn(R 10 )2、Ge(R 10 )2〔In the formula, R 10 [Indicates alkyl, phenyl, naphthyl, or their derivatives], Si(OR) 20 2. Sn(OR) 20 2. Ge (OR) 20 2. Ti(OR) 20 2. Cr(OR) 20 )2〔In the formula, R 20 [Indicates alkyl, phenyl, naphthyl, trialkylsilyl, dialkylalkoxysilyl, or their derivatives], Sn(SR 30 2. Ge(SR) 30 )2〔In the formula, R 30 [Indicates alkyl, phenyl, naphthyl, or their derivatives, etc.]

[0078] Examples of metal oxide atoms include VO, MnO, and TiO.

[0079] M 1 More preferably, Cu, Zn, Fe, Co, Ni, Pd, Mg, VO, TiO, even more preferably Cu, Zn, Ni, VO, and particularly preferably Cu, VO.

[0080] In formula (I), M 1 When the atom is a hydrogen atom or a monovalent metal atom, m is 2, M 1When the atom is a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, or an oxidized metal atom, m is 1.

[0081] *a, *a1, *a2, *b, *b1, *b2, *c1, and *c2 all represent chemical bonds. One of the two *a bonds is bonded to *a1, and the other to *a2. One of the two *b bonds is bonded to *b1, and the other to *b2. *c1 and *c2 are bonded to M. 1 Bonding.

[0082] If such bonding occurs, then the compound represented by formula (I) represents the compound represented by formulas (I-1) to (I-4) described later.

[0083] In formula (I), X 1 and X 2 Each independently represents a hydrogen atom, SR 1 or NR 2 R 3 X 1 and X 2 The preferred combination is hydrogen atoms and SR. 1 Combinations or SR 1 With NR 2 R 3 The combination of .

[0084] Y 1 and Y 2 Each is preferably a hydrogen atom or SR. 1 .

[0085] R 1 Preferably, it is an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 18 carbon atoms, and even more preferably phenyl, o-tolyl, m-tolyl, p-tolyl, or 2,4,6-trimethylphenyl. 2 and R 3 Each of the components is preferably a hydrogen atom or an alkyl group having 1 to 10 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, and even more preferably a hydrogen atom, methyl, ethyl, propyl, butyl, or pentyl.

[0086] Ideally, m should be 1, and M should be 1. 1 It is a divalent metal atom or a metal oxide atom.

[0087] M 1 Preferably, it is an oxide metal atom belonging to Group 5 of the periodic table, or a divalent metal atom belonging to Groups 9 to 12 of the periodic table, more preferably VO, Ni, Pd, Co, Zn or Cu.

[0088] In this application, formula (I) is sometimes abbreviated as formula (Ia), and the compound represented by formula (Ia) is the same as the compound represented by formula (I).

[0089]

[0090] The compound represented by formula (II) is described below.

[0091]

[0092] In formula (II), Z 1 and Z 2 Each can be independently represented by an oxygen atom, a sulfur atom, or NR. 4 .

[0093] R 4 An alkyl group having 1 to 10 hydrogen or carbon atoms, wherein the methylene group may be replaced with an oxygen atom.

[0094] Ar 1 It represents an arylene with 6 to 20 carbon atoms or a heteroarylene with 3 to 20 carbon atoms, wherein the hydrogen atoms contained in the arylene and heteroarylene can be replaced by halogen atoms or alkoxy groups with 1 to 20 carbon atoms.

[0095] Z 3 and Z 4 Each independently represents a hydrogen atom, N(R) 6 2. OR 5 or SR 5 .

[0096] R 5 The alkyl group represents an alkyl group with 1 to 20 carbon atoms, an aryl group with 6 to 20 carbon atoms, or a heteroaryl group with 3 to 20 carbon atoms. The hydrogen atom contained in the alkyl group may be replaced by a halogen atom, the methylene group contained in the alkyl group may be replaced by an oxygen atom, and the hydrogen atom contained in the aryl group and the heteroaryl group may be replaced by a halogen atom or an alkoxy group with 1 to 20 carbon atoms.

[0097] R 6 It represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms (the hydrogen atom contained in the alkyl group can be replaced by an aryl group having 6 to 10 carbon atoms, and the methylene group contained in the alkyl group can be replaced by an oxygen atom).

[0098] There are multiple Z in one molecule. 1 Z 2 Z 3 Z 4 Ar 1 R 4 R 5 or R 6 In this case, they can be the same or different.

[0099] M 2 It represents a hydrogen atom, a monovalent metal atom, a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, or an oxide metal atom.

[0100] M 2 When n is a hydrogen atom or a monovalent metal atom, n is 2, and M is 2. 2 When the atom is a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, or an oxidized metal atom, n is 1.

[0101] *d, *d1, *d2, *e, *e1, *e2, *f1, and *f2 all represent chemical bonds. One of the two *d bonds is bonded to *d1, and the other to *d2. One of the two *e bonds is bonded to *e1, and the other to *e2. *f1 and *f2 are bonded to M. 2 Bonding.

[0102] R 4 The alkyl group represented can be exemplified by those in R. 2 and R 3 The same alkyl group as described above. R 4 The hydrogen atoms contained in the alkyl group can be replaced by aryl groups with 6 to 20 carbon atoms.

[0103] As R 5 The alkyl group represented, except for the R group mentioned above. 4 Besides the alkyl group indicated, other examples include undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecanyl, octadecyl, nonadecanyl, and eicosyl. The number of carbon atoms in the alkyl group is preferably 1 to 18, more preferably 1 to 15, even more preferably 1 to 12, even more preferably 1 to 10, and particularly preferably 2 to 8.

[0104] The so-called R 4 R 5 and R 6 The group obtained by replacing the methylene group of an alkyl group with an oxygen atom is the group formed by replacing the methylene group of an alkyl group with an oxygen atom. The group obtained by replacing the methylene group of an alkyl group with an oxygen atom is preferably a group with 1 to 10 carbon atoms, more preferably a group with 1 to 6 carbon atoms (the methylene group before the oxygen atom is not included in the carbon atom number. For example, ethoxy has 2 carbon atoms). R 4 R 5 and R 6 The alkyl group represented is preferably a straight-chain alkyl group. Examples of such groups include those represented by the following formulas. In the following formulas, * represents a chemical bond.

[0105]

[0106] R 5 Examples of aryl groups with 6 to 20 carbon atoms or heteroaryl groups with 3 to 20 carbon atoms mentioned above are those with the same R group as those mentioned above. 1 The same aryl or heteroaryl group as described above.

[0107] R 6 Alkyl groups representing 1 to 10 carbon atoms can be exemplified by those in R 2 ~R 4 The same alkyl group as described above. The hydrogen atom in this alkyl group can be replaced by an aryl group having 6 to 10 carbon atoms; examples of such aryl groups include those described in R... 1 and R 5 The same aryl group as described above.

[0108] As Ar 1 The arylene group representing 6 to 20 carbon atoms or the heteroarylene group representing 3 to 20 carbon atoms can be exemplified by those in R. 1 The divalent group is obtained by removing and replacing the hydrogen atoms in the aryl or heteroaryl groups described herein with single bonds. The number of carbon atoms in the aryl or heteroaryl group is preferably 3 to 18, more preferably 3 to 12, and even more preferably 3 to 9.

[0109] Preferably, it is an arylene group, more preferably a phenyldiyl, diphenyldiyl, naphthyl, anthracenediyl, fluorenediyl, biphenylene (e.g., biphenyl-2,2'-diyl), etc.

[0110] Can be used with R 5 The alkyl group represents a halogen atom that is substituted with a hydrogen atom, and a halogen atom that can react with Ar. 1 The halogen atom that is substituted for the hydrogen atom in the arylene and heteroarylene groups represented is preferably a chlorine atom, a bromine atom, a fluorine atom, or an iodine atom.

[0111] As R 5 The aryl and heteroaryl groups represented include alkoxy groups with 1 to 20 carbon atoms that can be substituted with hydrogen atoms, and Ar... 1 The alkoxy groups containing 1 to 20 carbon atoms in the arylene and heteroarylene groups that can be substituted with hydrogen atoms can be exemplified by those in R 1 The same alkoxy group as described above that can be substituted with the hydrogen atoms contained in aryl and heteroaryl groups.

[0112] As Z 1 and Z 2 NR 4 (-N(R 4)-), examples include -N(CH3)-, -N(CH2CH3)-, -N(CH2CH2CH3)-, -N(CH2(CH3)CH3)-, -N(CH2CH2CH2CH3)-, -N(CH2CH2(CH3)CH3)-, -N(CH2CH2CH2CH2CH3)-, -N(CH2CH2CH2CH2C H2CH3)-, -N(CH2CH2CH2CH2CH2CH2CH3)-, -N(CH2CH2CH2CH2CH2CH2CH2CH3)-, -N(CH2CH2CH2CH2CH2CH2CH2CH2CH3)-, -N(CH2CH2CH2CH2CH2CH2CH2CH2CH2CH3)-, etc.

[0113] As Z 3 and Z 4 N(R) represents 6 )2. Examples include amino, methylamino, ethylamino, 2-ethylhexylamino, N,N-dimethylamino, N-ethyl-N-methylamino, N,N-diethylamino, N-propyl-N-methylamino, N,N-dipropylamino, N-isopropyl-N-methylamino, N,N-diisopropylamino, N,N-diisobutylamino, N,N-di(sec-butyl)amino, N-(tert-butyl)-N-methylamino, N,N-di(tert-butyl)amino, N-butyl-N-methylamino, N,N-dibutylamino, etc.

[0114] Z 3 and Z 4 OR 5 Preferably, it is an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, or a heteroaryloxy group having 3 to 20 carbon atoms. Examples of alkoxy groups having 1 to 20 carbon atoms, aryloxy groups having 6 to 20 carbon atoms, or heteroaryloxy groups having 3 to 20 carbon atoms are respectively related to R. 5 The alkoxy groups containing 1 to 20 carbon atoms in the aryl and heteroaryl groups described herein, which can be substituted with hydrogen atoms, in Y 1 and Y 2 The same group as the aryloxy or heteroaryloxy groups described in the document.

[0115] Z 3 and Z 4 SR 5 Preferably, it is an alkylthioalkyl group with 1 to 20 carbon atoms, an arylthioalkyl group with 6 to 20 carbon atoms, or a heteroarylthioalkyl group with 3 to 20 carbon atoms.

[0116] Examples of arylthioalkyl groups having 6 to 20 carbon atoms, or heteroarylthioalkyl groups having 3 to 20 carbon atoms, can be found in relation to X. 1 and X2 The same group as arylthioalkyl or heteroarylthioalkyl.

[0117] Examples of alkylthioalkyl groups having 1 to 20 carbon atoms include R 5 The group is obtained by replacing the oxygen atom in the alkoxy group (1 to 20 carbon atoms) of the aryl and heteroaryl groups that can be substituted with hydrogen atoms with a sulfur atom.

[0118] M 2 It represents a hydrogen atom, a monovalent metal atom, a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, or an oxide metal atom.

[0119] Examples of monovalent metal atoms include Na, K, and Li.

[0120] Metal atoms contained in divalent, trivalent, tetravalent, or oxide metal atoms, for example, metal atoms belonging to groups 3 to 15 of the periodic table.

[0121] Examples of divalent metal atoms include Cu, Zn, Fe, Co, Ni, Ru, Pb, Rh, Pd, Pt, Mn, Sn, and Pb.

[0122] Examples of trivalent substituted metal atoms include Al-F, Al-Cl, Al-Br, Al-I, Al-OH, Ga-F, Ga-Cl, Ga-Br, Ga-I, In-F, In-Cl, In-Br, In-I, Tl-F, Tl-Cl, Tl-Br, Tl-I, Al-C6H5, Al-C6H4(CH3), In-C6H5, In-C6H4(CH3), Mn(OH), Mn(OC6H5), Mn[OSi(CH3)3], Fe-Cl, Ru-Cl, etc.

[0123] Examples of tetravalent substituted metal atoms include CrCl2, SiCl2, SiBr2, SiF2, SiI2, ZrCl2, ZrI2, GeCl2, GeBr2, GeF2, GeI2, SnCl2, SnF2, SnBr2, TiF2, TiCl2, TiBr2, Si(OH)2, Ge(OH)2, Zr(OH)2, Mn(OH)2, Sn(OH)2, and Ti(R). 10 2. Cr(R) 10 )2、Si(R 10 )2、Sn(R 10 )2、Ge(R 10 )2〔In the formula, R 10[Indicates alkyl, phenyl, naphthyl, or their derivatives], Si(OR) 20 2. Sn(OR) 20 2. Ge (OR) 20 2. Ti(OR) 20 2. Cr(OR) 20 )2〔In the formula, R 20 [Indicates alkyl, phenyl, naphthyl, trialkylsilyl, dialkylalkoxysilyl, or their derivatives], Sn(SR 30 2. Ge(SR) 30 )2〔In the formula, R 30 [Indicates alkyl, phenyl, naphthyl, or their derivatives, etc.]

[0124] Examples of metal oxide atoms include VO, MnO, and TiO.

[0125] M 2 More preferably, Cu, Zn, Fe, Co, Ni, Pd, Mg, VO, TiO, even more preferably Cu, Zn, Ni, VO, and particularly preferably Cu, VO.

[0126] M 2 When n is a hydrogen atom or a monovalent metal atom, n is 2, and M is 2. 2 When the atom is a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, or an oxidized metal atom, n is 1.

[0127] *d, *d1, *d2, *e, *e1, *e2, *f1, and *f2 all represent chemical bonds. One of the two *d bonds is bonded to *d1, and the other to *d2. One of the two *e bonds is bonded to *e1, and the other to *e2. *f1 and *f2 are bonded to M. 2 Bonding.

[0128] If such bonding occurs, then the compound represented by formula (II) represents the compound represented by formulas (II-1) to (II-4) described later.

[0129] In equation (II), Z 1 and Z 2 Each can be independently represented by an oxygen atom, a sulfur atom, or NR. 4 .

[0130] Z 1 and Z 2 The preferred combination is a combination of oxygen atoms with oxygen atoms or sulfur atoms with NR. 4 The combination of R. 4Preferably, it is an alkyl group with 1 to 10 hydrogen atoms or carbon atoms, more preferably an alkyl group with 1 to 8 hydrogen atoms or carbon atoms, and even more preferably a hydrogen atom or methyl, ethyl, propyl, butyl, pentyl, hexyl, 2-ethylhexyl, or 1-phenylmethyl.

[0131] Ar 1 Preferably, it is an arylene with 6 to 20 carbon atoms, more preferably an arylene with 6 to 18 carbon atoms, and even more preferably biphenyl-2,2'-diyl or phenyl-1,2-diyl.

[0132] Z 3 and Z 4 Each is independently preferred to be SR 5 OR 5 or N(R) 6 )2.

[0133] Z 3 and Z 4 The combination of OR is preferred 5 With N(R) 6 Combinations of 2, OR 5 OR 5 Combinations, or OR 5 With SR 5 The combination of .

[0134] R 5 Preferably, it is an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 20 carbon atoms, more preferably an aryl group having 6 to 20 carbon atoms, and even more preferably 1-naphthyl, 2-naphthyl, o-tolyl, m-tolyl, p-tolyl, 2,4,6-trimethylphenyl, or (1,1-dimethyl-3,3-dimethylbutyl)phenyl. 6 Preferably, it is an alkyl group having 1 to 8 carbon atoms, M 2 Preferably, it is an oxide metal atom belonging to Group 5 of the periodic table, or a divalent metal atom belonging to Groups 9 to 12 of the periodic table, more preferably VO, Ni, Pd, Co, Zn or Cu.

[0135] In this application, formula (II) is sometimes abbreviated as formula (IIa), and the compound represented by formula (IIa) is the same as the compound represented by formula (II).

[0136]

[0137] The colorant (A) preferably includes one or more compounds represented by formulas (I-1) to (I-4) or one or more compounds represented by formulas (II-1) to (II-4).

[0138]

[0139] (where X) 1 X 2 Y 1 Y 2 M 1 (Same meaning as above.)

[0140]

[0141] (where Z) 1 Z 2 Ar 1 Z 3 Z 4 M 2 (Same meaning as above.)

[0142] The content of the compound represented by formula (I) or (II) (colorant (A1)) in the total amount of colorant (A) is preferably 20 to 100% by mass, more preferably 30 to 100% by mass, and even more preferably 40 to 100% by mass.

[0143] In the total amount of solid components in the coloring curable resin composition, the content of colorant (Al) is preferably 2 to 60% by mass, more preferably 4 to 55% by mass, and even more preferably 6 to 50% by mass.

[0144] It should be noted that, in this specification, the term "total amount of solid components" refers to the total amount of components remaining after removing the solvent from the coloring and curing resin composition of the present invention. The total amount of solid components and the content of each component therein can be determined by known analytical methods such as liquid chromatography and gas chromatography.

[0145] Colorant (A) preferably also contains a colorant different from colorant (A1) (hereinafter also referred to as colorant (A2)).

[0146] The colorant (A2) can be any colorant in dyes or pigments.

[0147] Examples of dyes include, for instance, compounds classified as hues other than pigments in the Dye Index (published by The Society of Dyers and Colourists) and known dyes listed in dyeing guides (by dyeing companies). Xanthan dyes are particularly preferred.

[0148] Xanthan dyes are dyes containing compounds having a xanthan skeleton within their molecules. Examples of xanthan dyes include, for instance, C1 Acid Red 51 (hereinafter, the description of C1 Acid Red is omitted and only the number is listed. The same applies to others.), 52, 87, 92, 94, 289, 388, C1 Acid Violet 9, 30, 102, C1 Basic Red 1 (Rhodamine 6G), 2, 3, 4, 8, 10, 11, C1 Basic Violet 10 (Rhodamine B), 11, C1 Solvent Red 218, C1 Mordant Red 27, C1 Reactive Red 36 (Rose Red B), sulfonylrhodamine G, xanthan dyes described in Japanese Patent Application Publication No. 2010-32999, and xanthan dyes described in Japanese Patent Publication No. 4492760. Xanthan dyes that are soluble in organic solvents are preferred.

[0149] Commercially available xaton dyes can be used (e.g., "Chugai AminolFast Pink RH / C" manufactured by Chugai Chemical Co., Ltd., and "Rhodamin 6G" manufactured by Taoka Chemical Co., Ltd.). Alternatively, commercially available xaton dyes can be used as starting materials for synthesis, referring to Japanese Patent Application Publication No. 2010-32999.

[0150] Other dyes that can be used include azo dyes, cyanine dyes, triphenylmethane dyes, thiazole dyes, oxazine dyes, phthalocyanine dyes, quinoline dyes, anthraquinone dyes, naphthoquinone dyes, quinone imine dyes, methyl benzoate dyes, methyl imine dyes, squaric acid dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes, and each can be a known dye.

[0151] Specifically, examples of such dyes include:

[0152] CI Solvent Yellow 4 (hereinafter, CI Solvent Yellow is omitted and only the number is recorded.), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99, 117, 162, 163, 167, 189;

[0153] 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;

[0154] CI Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86;

[0155] CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

[0156] 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;

[0157] CI solvent green dyes 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35, etc.

[0158] 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, 15 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;

[0159] 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;

[0160] CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;

[0161] CI Acid Violet 6B, 7, 15, 16, 17, 19, 21, 23, 24, 25, 34, 38, 49, 72;

[0162] Acid Blue (CI) 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;

[0163] CI Acid Green includes 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.

[0164] 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;

[0165] 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;

[0166] CI direct orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

[0167] CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;

[0168] 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, 16 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;

[0169] CI Direct Green includes CI direct dyes such as 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, and 82.

[0170] CI Disperse Yellow 51, 54, 76;

[0171] CI Disperse Violet 26, 27;

[0172] CI disperse blue 1, 14, 56, 60, and other CI disperse dyes.

[0173] 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;

[0174] CI Basic Violet 2;

[0175] CI Basic Red 9;

[0176] CI Basic Green 1; and other CI basic dyes.

[0177] CI Active Yellow 2, 76, 116;

[0178] CI Active Orange 16;

[0179] CI Reactive Red 36; and other CI reactive dyes.

[0180] CI Media Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;

[0181] CI Media 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;

[0182] CI Media Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;

[0183] CI Media Purple 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;

[0184] CI Media 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;

[0185] CI mordant green dyes include 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, and 53.

[0186] CI vat green 1 and other CI vat dyes, etc.

[0187] As for pigments, for example, pigments classified as pigments in the Dye Index (published by The Society of Dyers and Colourists) can be cited, such as the following pigments.

[0188] Green pigments: CI pigments Green 7, 36, 58, etc.

[0189] Yellow pigments: 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.

[0190] Orange pigments: CI pigments Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, etc.

[0191] Red pigments: 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.

[0192] Blue pigments: CI pigment blue 15, 15:3, 15:4, 15:6, 60, etc.

[0193] Purple pigments: CI pigments purple 1, 19, 23, 29, 32, 36, 38, etc.

[0194] These pigments can be used with one or more pigments for each color, or a combination of pigments of different colors can be used.

[0195] Pigments can undergo various treatments as needed, including rosin treatment, surface treatment with pigment derivatives incorporating acidic or basic groups, grafting treatment using polymers, micronization treatment using sulfuric acid micronization, cleaning treatment using organic solvents or water to remove impurities, and removal of ionic impurities using ion exchange. The pigment particle size is preferably approximately uniform. By dispersing the pigment with a pigment dispersant, a pigment dispersion in which the pigment is uniformly dispersed in a pigment dispersant solution can be produced. Pigments can be dispersed individually or in combination.

[0196] As pigment dispersants, the same pigment dispersants as those mentioned above can be cited.

[0197] When using a pigment dispersant, the amount used is preferably 10 to 200 parts by mass relative to 100 parts by mass of pigment, more preferably 15 to 180 parts by mass, and even more preferably 20 to 160 parts by mass. If the amount of pigment dispersant used is within the aforementioned range, when using two or more pigments, there is a tendency to obtain a pigment dispersion with a more uniform dispersion state.

[0198] When colorant (A) includes colorant (A2), the content of colorant (A2) in the total amount of colorant (A) is preferably 1 to 80% by mass, more preferably 1 to 70% by mass, and even more preferably 1 to 60% by mass.

[0199] The content of colorant (A) in the coloring curable resin composition is typically 1% to 70% by mass relative to the total amount of solid components, preferably 2% to 65% by mass, more preferably 5% to 60% by mass, and particularly preferably 7% to 55% by mass. If the content of the aforementioned compound is within the aforementioned range, it is easier to obtain the desired spectroscopic and color concentration.

[0200] <Resin (B)>

[0201] The resin (B) is not particularly limited, but an alkali-soluble resin is preferred. Examples of resin (B) include resins [K1] to [K6].

[0202] Resin [K1]: A copolymer having structural units of at least one (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides, and structural units of monomers (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an olefinic unsaturated bond;

[0203] Resin [K2]: A copolymer having structural units from (a), structural units from (b), and structural units from monomer (c) capable of copolymerizing with (a) (however, different from (a) and (b)). (Hereinafter sometimes referred to as "(c)")

[0204] Resin [K3]: A copolymer having structural units from (a) and structural units from (c);

[0205] Resin [K4]: A copolymer having a structural unit formed by adding (b) to a structural unit from (a) and a structural unit from (c);

[0206] Resin [K5]: A copolymer having structural units formed by adding (a) to structural units from (b) and structural units from (c);

[0207] Resin [K6]: A copolymer having a structural unit formed by adding (a) to a structural unit from (b) and further adding a carboxylic anhydride, and a structural unit from (c).

[0208] As for (a), specifically, examples include:

[0209] Unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, ortho-, meta-, and p-vinylbenzoic acid;

[0210] Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, zeaxanthin, itaconic acid, 3-vinyl phthalic acid, 4-vinyl phthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid.

[0211] 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, 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene, etc., are bicyclic unsaturated compounds containing carboxyl groups;

[0212] Maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinyl phthalic anhydride, 4-vinyl phthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxylic acid bicyclic [2.2.1]hept-2-ene anhydride and other unsaturated dicarboxylic acid anhydrides;

[0213] Unsaturated mono[(meth)acryloyloxyethyl] esters of polycarboxylic acids with two or more members, such as succinate mono[2-(meth)acryloyloxyethyl] ester and phthalate mono[2-(meth)acryloyloxyethyl] ester.

[0214] Unsaturated acrylates such as α-(hydroxymethyl)acrylic acid, which contain both hydroxyl and carboxyl groups in the same molecule.

[0215] Among these, acrylic acid, methacrylic acid, and maleic anhydride are preferred, considering both copolymerization reactivity and the solubility of the resulting resin in alkaline aqueous solutions.

[0216] (b) For example, it refers to a polymeric compound having a cyclic ether structure having 2 to 4 carbon atoms (e.g., selected from at least one of the group consisting of ethylene oxide ring, oxobutane ring and tetrahydrofuran ring) and an olefinic unsaturated bond. (b) Preferably, it is a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0217] It should be noted that in this specification, "(meth)acrylic acid" means at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" have the same meaning.

[0218] As (b), examples include monomers having epoxy ethyl and olefinic unsaturated bonds (b1) (hereinafter sometimes referred to as "(b1)"), monomers having oxocyclobutyl and olefinic unsaturated bonds (b2) (hereinafter sometimes referred to as "(b2)"), monomers having tetrahydrofuranyl and olefinic unsaturated bonds (b3) (hereinafter sometimes referred to as "(b3)"), etc.

[0219] As (b1), for example, examples include monomers (b1-1) (hereinafter sometimes referred to as "(b1-1)") having a structure in which aliphatic unsaturated hydrocarbons are epoxidized in a straight or branched manner, and monomers (b1-2) (hereinafter sometimes referred to as "(b1-2)") having a structure in which alicyclic unsaturated hydrocarbons are epoxidized.

[0220] Examples of (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methylo-vinylbenzyl glycidyl ether, α-methylm-vinylbenzyl glycidyl ether, α-methylp-vinylbenzyl glycidyl ether, and 2,3-bis(glycidyloxymethyl) Styrene, 2,4-bis(glycidoxymethyl)styrene, 2,5-bis(glycidoxymethyl)styrene, 2,6-bis(glycidoxymethyl)styrene, 2,3,4-tris(glycidoxymethyl)styrene, 2,3,5-tris(glycidoxymethyl)styrene, 2,3,6-tris(glycidoxymethyl)styrene, 3,4,5-tris(glycidoxymethyl)styrene, 2,4,6-tris(glycidoxymethyl)styrene, etc.

[0221] Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide 2000; manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexyl methyl methacrylate (e.g., Cyclomer A400; manufactured by Daicel Co., Ltd.), 3,4-epoxycyclohexyl methyl methacrylate (e.g., Cyclomer M100; manufactured by Daicel Co., Ltd.), and 3,4-epoxytricyclo(5.2.1.0) methacrylate. 2,6 Decyl ester, (meth)acrylate 3,4-epoxytricyclic [5.2.1.0] 2,6 Decyloxyethyl ester, etc.

[0222] As (b2), a monomer having an oxetyl group and a (meth)acryloyloxy group is more preferred. Examples of (b2) include 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, and the like.

[0223] As (b3), a monomer having a tetrahydrofuran group and a (meth)acryloyloxy group is more preferred. Specifically, examples of (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemicals Co., Ltd.), tetrahydrofurfuryl methacrylate, etc.

[0224] As for (b), from the perspective of further improving the reliability of the obtained optical filter, such as heat resistance and chemical resistance, (b1) is preferred. Furthermore, from the perspective of excellent storage stability of the coloring and curing resin composition, (b1-2) is more preferred.

[0225] As for (c), for example, the following can be cited:

[0226] Methyl methacrylate, ethyl methacrylate, n-butyl methacrylate, sec-butyl methacrylate, tert-butyl methacrylate, 2-ethylhexyl methacrylate, dodecyl methacrylate, lauryl methacrylate, stearyl methacrylate, cyclopentyl methacrylate, cyclohexyl methacrylate, 2-methylcyclohexyl methacrylate, tricyclo[5.2.1.0] 2,6] Decane-8-yl ester (in this technical field, it is commonly referred to as "(meth)acrylate dicyclopentyl ester". Additionally, it is sometimes called "(meth)acrylate tricyclodecyl ester".), (meth)acrylate tricyclo[5.2.1.0] 2,6 Decen-8-yl ester (commonly referred to as "(meth)acrylate dicyclopentenyl ester"), (meth)acrylate dicyclopentyloxyethyl ester, (meth)acrylate isobornyl ester, (meth)acrylate adamantane ester, (meth)acrylate allyl ester, (meth)acrylate propargyl ester, (meth)acrylate phenyl ester, (meth)acrylate naphthyl ester, (meth)acrylate benzyl ester, and other (meth)acrylate esters;

[0227] 2-Hydroxyethyl methacrylate, 2-Hydroxypropyl methacrylate, and other methacrylates containing hydroxyl groups;

[0228] Diethyl maleate, diethyl fumarate, diethyl itaconic acid, and other dicarboxylic acid diesters;

[0229] 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-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo [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, 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]Hept-2-ene, etc., are bicyclic unsaturated compounds;

[0230] Dicarbonylimide 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, N-(9-acridinyl)maleimide, etc.;

[0231] 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.

[0232] Among these, from the aspects of copolymerization reactivity and heat resistance, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, etc. are preferred.

[0233] In resin [K1], among all the structural units constituting resin [K1], the ratio of the structural units from each is preferably:

[0234] Structural units from (a): 2 to 60 mol%

[0235] Structural units from (b): 40 to 98 mol%,

[0236] More preferably:

[0237] Structural units from (a): 10 to 50 mol%

[0238] Structural units from (b): 50 to 90 mol%.

[0239] If the ratio of the structural units of resin [K1] is within the above range, the storage stability of the colored curable resin composition, the developability when forming a colored pattern, and the solvent resistance of the obtained optical filter tend to be excellent.

[0240] Resin [K1] can be manufactured, for example, by the methods described in the reference document "Experimental Methods of Polymer Synthesis" (実験法高分子合成)(written by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., the 1st edition, the 1st printing, issued on March 1, 1972) and the cited documents described in this document.

[0241] Specifically, the following method can be used: The specified amounts of (a) and (b), the polymerization initiator, and the solvent are added to a reaction vessel. For example, oxygen is replaced with nitrogen to create a deoxygenated atmosphere. Heating and maintaining the temperature are performed while stirring. It should be noted that the polymerization initiator and solvent used here are not particularly limited; substances commonly used in the field can be used. For example, as polymerization initiators, examples include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylpentanonitrile) etc.) and organic peroxides (benzoyl peroxide, etc.). As solvents, any solvent that dissolves the monomers is acceptable; examples include solvents (E) used as solvents in the coloring and curing resin composition of the present invention, as described below.

[0242] It should be noted that, regarding the obtained copolymer, the solution after the reaction can be used directly, or a concentrated or diluted solution can be used, or a substance extracted in solid (powder) form by methods such as reprecipitation can be used. In particular, by using the solvent contained in the color-curing resin composition of the present invention as the solvent during the polymerization, the solution after the reaction can be directly used in the preparation of the color-curing resin composition of the present invention, thus simplifying the manufacturing process of the color-curing resin composition of the present invention.

[0243] In resin [K2], the preferred ratio of structural units from each of the various structural units constituting resin [K2] is:

[0244] Structural units from (a): 2–45 mol%

[0245] Structural units from (b): 2–95 mol%

[0246] Structural units from (c): 1–65 mol%.

[0247] More preferably:

[0248] Structural units from (a): 5–40 mol%

[0249] Structural units from (b): 5–80 mol%

[0250] Structural units from (c): 5–60 mol%.

[0251] If the ratio of the structural units of resin [K2] is within the above range, the color-curable resin composition tends to have excellent storage stability, developability when forming color patterns, and solvent resistance, heat resistance and mechanical strength of the obtained optical filter.

[0252] Resin [K2] can be manufactured, for example, in the same manner as the method described for manufacturing resin [K1].

[0253] In resin [K3], the preferred ratio of structural units from each of the various structural units constituting resin [K3] is:

[0254] Structural units from (a): 2–60 mol%

[0255] Structural units from (c): 40–98 mol%.

[0256] More preferably:

[0257] Structural units from (a): 10–50 mol%

[0258] Structural units from (c): 50–90 mol%.

[0259] Resin [K3] can be manufactured, for example, in the same manner as the method described for manufacturing resin [K1].

[0260] The resin [K4] can be manufactured by obtaining a copolymer of (a) and (c) by adding a cyclic ether having 2 to 4 carbon atoms in (b) to a carboxylic acid and / or carboxylic anhydride in (a).

[0261] First, the copolymers of (a) and (c) are manufactured in the same manner as described in the method for manufacturing resin [K1]. In this case, the ratio of the structural units from each is preferably the same as that described in resin [K3].

[0262] Next, the cyclic ether having 2 to 4 carbon atoms in (b) is reacted with a portion of the carboxylic acid and / or carboxylic anhydride from (a) in the copolymer described above.

[0263] After producing the copolymer of (a) and (c), the atmosphere in the flask is replaced with air instead of nitrogen, and (b), a reaction catalyst (e.g., tris(dimethylaminomethyl)phenol) and a polymerization inhibitor (e.g., hydroquinone) are added to the flask. The reaction is carried out at 60–130°C for 1–10 hours, thereby producing resin [K4].

[0264] The amount of (b) used is preferably 5 to 80 moles, more preferably 10 to 75 moles, relative to 100 moles of (a). By setting it within this range, there is a tendency for the coloring and curing resin composition to have better storage stability, developability when forming a pattern, and a better balance of solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern. Considering the high reactivity of cyclic ethers and the fact that unreacted (b) is less likely to remain, (b1) is preferred as (b) used in resin [K4], and more preferably (b1-1).

[0265] The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass relative to the total amount of (a), (b), and (c) 100 parts by mass. The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass relative to the total amount of (a), (b), and (c) 100 parts by mass.

[0266] The charging method, reaction temperature, and time, among other reaction conditions, can be appropriately adjusted by taking into account the manufacturing equipment and the heat generated by polymerization. It should be noted that the charging method and reaction temperature can be appropriately adjusted by considering the manufacturing equipment and the heat generated by polymerization, similar to the polymerization conditions.

[0267] Regarding resin [K5], as a first stage, copolymers of (b) and (c) are obtained in the same manner as resin [K1] described above. Similarly, regarding the obtained copolymer, the solution after the reaction can be used directly, or a concentrated or diluted solution can be used, or a substance extracted in solid (powder) form by methods such as reprecipitation can be used.

[0268] The preferred ratios of structural units from (b) and (c) are respectively, relative to the total number of moles of all structural units constituting the copolymer described above.

[0269] Structural units from (b): 5–95 mol%

[0270] Structural units from (c): 5–95 mol%.

[0271] More preferably:

[0272] Structural units from (b): 10–90 mol%

[0273] Structural units from (c): 10–90 mol%.

[0274] Furthermore, under the same conditions as the manufacturing method of resin [K4], the carboxylic acid or carboxylic anhydride contained in (a) is reacted with the cyclic ether from (b) contained in the copolymer of (b) and (c), thereby obtaining resin [K5].

[0275] The amount of (a) used in reaction with the copolymer described above is preferably 5 to 80 moles relative to 100 moles of (b). Considering the high reactivity of cyclic ethers and the low likelihood of unreacted (b) residue, (b1) is preferred as (b) used in resin [K5], and (b1-1) is even more preferred.

[0276] Resin [K6] is a resin obtained by further reacting carboxylic anhydride with resin [K5]. The carboxylic anhydride is reacted with a hydroxyl group (which is generated by the reaction of a cyclic ether with a carboxylic acid or carboxylic anhydride).

[0277] Examples of carboxylic anhydrides 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, and 5,6-dicarboxylic bicyclo[2.2.1]hept-2-ene anhydride. The amount of carboxylic anhydride used is preferably 0.5 to 1 mole relative to 1 mole of (a).

[0278] Specific examples of resin (B) include: methyl 3,4-epoxycyclohexyl methacrylate / (meth)acrylate copolymer, and 3,4-epoxytricyclic methacrylate [5.2.1.0]. 2,6 ] Decyl ester / (meth)acrylic acid copolymer and other resins [K1]; glycidyl methacrylate / benzyl methacrylate / (meth)acrylic acid copolymer, glycidyl methacrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxy tricyclic acrylic acid [5.2.1.0] 2,6 Decyl ester / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxy tricyclic acrylic acid [5.2.1.0] 2,6 Resins such as decyl acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / (meth)acrylic acid 2-hydroxyethyl ester copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer [K2]; resins such as benzyl acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer [K3]; resins formed by adding glycidyl methacrylate to benzyl acrylate / (meth)acrylic acid copolymer, resins formed by adding glycidyl methacrylate to tricyclodecyl acrylate / styrene / (meth)acrylic acid copolymer, and resins formed by adding glycidyl methacrylate to tricyclodecyl acrylate / styrene / (meth)acrylic acid copolymer. Resins such as resins formed by adding glycidyl methacrylate to a copolymer of cyclodecyl methacrylate / benzyl methacrylate / methacrylic acid [K4]; resins formed by reacting a copolymer of tricyclodecyl methacrylate / glycidyl methacrylate with (meth)acrylic acid; resins formed by reacting a copolymer of tricyclodecyl methacrylate / styrene / glycidyl methacrylate with (meth)acrylic acid; resins such as resins formed by reacting a copolymer of tricyclodecyl methacrylate / glycidyl methacrylate with (meth)acrylic acid; and resins formed by further reacting the resin with tetrahydrophthalic anhydride [K6].

[0279] The resin (B) is preferably a copolymer (resin [K1] or resin [K2]) comprising at least one structural unit selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides, and a structural unit having a cyclic ether structure with 2 to 4 carbon atoms and an olefinic unsaturated bond. It is more preferably resin [K2].

[0280] The weight-average molecular weight of resin (B), converted from polystyrene, is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 5,000 to 30,000. If the molecular weight is within the aforementioned range, there is a tendency for the optical filter to have increased hardness, higher residual film rate, better solubility of the unexposed portion in the developer, and improved resolution of the colored pattern.

[0281] The dispersion of resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1.1 to 6, more preferably 1.2 to 4.

[0282] The acid value of resin (B), converted from solid content, is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150 mg-KOH / g, and even more preferably 70 to 135 mg-KOH / g. Here, the acid value is a value determined as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin (B), and can be obtained, for example, by titration using an aqueous solution of potassium hydroxide.

[0283] The content of resin (B) relative to the total amount of solid components is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and even more preferably 17 to 55% by mass. If the content of resin (B) is within the aforementioned range, there is a tendency to form colored patterns, and the resolution and residual film rate of the colored patterns are improved.

[0284] <Polymerizing Compound (C)>

[0285] The polymerizable compound (C) is a compound that can be polymerized using active free radicals and / or acids generated by the polymerization initiator (D). Examples include compounds with polymerizable olefinic unsaturated bonds, and (meth)acrylate compounds are preferred.

[0286] The polymeric compound (C) is preferably a polymeric compound having three or more olefinic unsaturated bonds. Examples of such polymerizable compounds include, for example, 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.

[0287] Among them, trimethylolpropane tri(meth)acrylate, dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate are preferred.

[0288] The weight-average molecular weight of the polymeric compound (C) is preferably 150 or more and 2,900 or less, more preferably 250 or more and 1,500 or less.

[0289] The content of the polymeric compound (C) relative to the total amount of solid components is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and even more preferably 17 to 55% by mass. If the content of the polymeric compound (C) is within the aforementioned range, there is a tendency to improve the residual film rate when forming colored patterns and the chemical resistance of the optical filter.

[0290] <Polymerization Initiator (D)>

[0291] The polymerization initiator (D) is any compound that can generate active free radicals, acids, etc., under the action of light or heat and is capable of initiating polymerization; there are no particular limitations, and known polymerization initiators can be used. Examples of polymerization initiators that generate active free radicals include alkyl phenyl ketone compounds, triazine compounds, acylphosphine oxide compounds, O-acyl oxime compounds, and biimidazole compounds.

[0292] The aforementioned O-acyl oxime compounds are compounds having a partial structure represented by formula (d1). Hereinafter, * denotes chemical bonds.

[0293]

[0294] Examples of the aforementioned O-acyl oxime compounds include, for instance, N-benzoyloxy-1-(4-phenylthioalkylphenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthioalkylphenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthioalkylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethane-1-imine, and N-acetoxy-1-[9-ethyl-6-{2-methyl-4-yl]ethane-1-imine. (3,3-Dimethyl-2,4-dioxanepentylmethyloxy)benzoyl}-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-imine, N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, etc. Commercially available products such as Irgacure OXE01, OXE02 (manufactured by BASF), and N-1919 (manufactured by ADEKA) can be used. The O-acyl oxime compound is preferably selected from at least one of the following groups: N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, and N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine; more preferably, N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine or N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine. Using these O-acyl oxime compounds tends to yield optical filters with high brightness.

[0295] The aforementioned alkyl phenyl ketone compounds are compounds 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 substituents.

[0296]

[0297] Examples of compounds having a partial structure represented by formula (d2) include, for example, 2-methyl-2-morpholino-1-(4-methylthiophenyl)propane-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutane-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholino)phenyl]butane-1-one. Commercially available products such as Irgacure 369, 907, and 379 (all manufactured by BASF) can be used.

[0298] Examples of compounds having a partial structure represented by formula (d3) include, for example, oligomers of 2-hydroxy-2-methyl-1-phenylpropane-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propane-1-one, 1-hydroxycyclohexylphenyl ketone, 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propane-1-one, α,α-diethoxyacetophenone, benzoyladimethyl ketal, etc.

[0299] From a sensitivity perspective, alkyl phenyl ketone compounds are preferably compounds having a partial structure represented by formula (d2).

[0300] Examples of the aforementioned triazine compounds include, for instance, 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-piperyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 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-methylphenyl)vinyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)vinyl]-1,3,5-triazine, etc.

[0301] Examples of the aforementioned acylphosphine oxide compounds include 2,4,6-trimethylbenzoyl diphenylphosphine oxide. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) can be used.

[0302] Examples of the aforementioned biimidazole compounds include, for example, 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 Publication No. 6-75372, Japanese Patent Application Publication No. 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, etc. Biimidazole compounds with alkoxyphenyl groups at the 4,4',5,5'- positions substituted with alkoxycarbonyl groups (e.g., see Japanese Patent Publication No. 48-38403, Japanese Patent Application Publication No. 62-174204, etc.), and biimidazole compounds with phenyl groups at the 4,4',5,5'-position substituted with alkoxycarbonyl groups (e.g., see Japanese Patent Application Publication No. 7-10913, etc.).

[0303] In addition, examples of polymerization initiators (D) include benzoin compounds such as benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as methyl benzoyl peroxide, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthroquinone, 2-ethylanthraquinone, and camphorquinone; and 10-butyl-2-chloroacridone, benzoin, methyl phenylglyoxylate, and titanium dioxide compounds. These are preferably used in combination with polymerization initiators (D1) (especially amines) described later.

[0304] Examples of polymerization initiators that generate acids include, for example, onion salts such as 4-hydroxyphenyl dimethyl sulfonium p-toluenesulfonate, 4-hydroxyphenyl dimethyl sulfonium hexafluoroantimonate, 4-acetoxyphenyl dimethyl sulfonium p-toluenesulfonate, 4-acetoxyphenyl methyl benzyl sulfonium hexafluoroantimonate, triphenyl sulfonium p-toluenesulfonate, triphenyl sulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, nitrobenzyl toluenesulfonate, and benzoin toluenesulfonate.

[0305] As a polymerization initiator (D), it is preferably a polymerization initiator comprising at least one selected from the group consisting of alkyl phenyl ketone compounds, triazine compounds, acylphosphine oxide compounds, O-acyl oxime compounds and bimidazole compounds, and more preferably a polymerization initiator comprising an O-acyl oxime compound.

[0306] The content of polymerization initiator (D) is preferably 0.1 to 30 parts by mass relative to 100 parts by mass of the total amount of resin (B) and polymerizable compound (C), and more preferably 1 to 20 parts by mass. If the content of polymerization initiator (D) is within the aforementioned range, there is a tendency to achieve higher sensitivity and shorten the exposure time, thereby increasing the productivity of optical filters.

[0307] <Polymerization Initiator (D1)>

[0308] A polymerization initiator (D1) is a compound or sensitizer used to promote the polymerization of a polymerizable compound that is initiated by a polymerization initiator. In cases where a polymerization initiator (D1) is included, it is typically used in combination with a polymerization initiator (D).

[0309] Examples of polymerization initiators (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0310] Examples of the aforementioned amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as michalcone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone, among which 4,4'-bis(diethylamino)benzophenone is preferred. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) can be used.

[0311] Examples of the aforementioned alkoxyanthracene compounds 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.

[0312] Examples of the aforementioned thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0313] Examples of the aforementioned carboxylic acid compounds include phenylthioalkylacetic acid, methylphenylthioalkylacetic acid, ethylphenylthioalkylacetic acid, methylethylphenylthioalkylacetic acid, dimethylphenylthioalkylacetic acid, methoxyphenylthioalkylacetic acid, dimethoxyphenylthioalkylacetic acid, chlorophenylthioalkylacetic acid, dichlorophenylthioalkylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0314] When using these polymerization initiators (D1), 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 resin (B) and polymerizable compound (C). If the amount of polymerization initiator (D1) is within this range, there is a tendency to be able to form colored patterns with higher sensitivity and to improve the productivity of optical filters.

[0315] <Solvent (E)>

[0316] The solvent (E) is not particularly limited and can be any solvent commonly used in this field. Examples include ester solvents (solvents containing -COO- but not -O-), ether solvents (solvents containing -O- but not -COO-), ether ester solvents (solvents containing both -COO- and -O-), ketone solvents (solvents containing -CO- but not -COO-), alcohol solvents (solvents containing OH but not -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc.

[0317] Examples of ester solvents 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.

[0318] Examples of ether solvents 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.

[0319] Examples of ether ester solvents 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-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.

[0320] Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0321] Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerol.

[0322] Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0323] Examples of amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0324] The solvent is preferably one or more selected from the group consisting of ether solvents, ether ester solvents, and amide solvents, more preferably including ether solvents, ether ester solvents, and amide solvents, and even more preferably including diethylene glycol methyl ethyl ether, propylene glycol monomethyl ether acetate, and N-methylpyrrolidone. With the solvent described above, the solubility of the colorant increases, making it less likely to generate foreign matter in the optical filter.

[0325] The solvent (E) content is preferably 70-95% by mass, more preferably 75-92% by mass, relative to the total amount of the color-curing resin composition of the present invention. In other words, the solid component of the color-curing resin composition is preferably 5-30% by mass, more preferably 8-25% by mass. If the solvent (E) content is within the aforementioned range, the flatness during coating becomes good, and since the color concentration is not insufficient when forming the optical filter, there is a tendency for the display characteristics to become good.

[0326] The content of ether solvent relative to the total amount of solvent is preferably 1 to 55% by mass, more preferably 2 to 53% by mass, and even more preferably 3 to 50% by mass.

[0327] The content of ether ester solvent relative to the total amount of solvent is preferably 1 to 30% by mass, more preferably 2 to 25% by mass, and even more preferably 3 to 20% by mass.

[0328] The content of amide solvent relative to the total amount of solvent is preferably 1 to 50% by mass, more preferably 2 to 47% by mass, and even more preferably 3 to 45% by mass.

[0329] <Leveling Agent (F)>

[0330] Examples of leveling agents (F) include silicone surfactants, fluorinated surfactants, and silicone surfactants containing fluorine atoms. They may have polymerizable groups on their side chains.

[0331] Examples of organosilicon surfactants include surfactants that have intramolecular siloxane bonds. Specifically, 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 name: Toray Corning Co., Ltd.), 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 Advanced Materials Japan Contract Co., Ltd.).

[0332] As examples of the aforementioned fluorinated surfactants, surfactants with intramolecular fluorocarbon chains can be cited. Specifically, examples include FLOURAD (registered trademark) FC430, FLOURAD FC431 (manufactured by Sumitomo 3M Co., Ltd.), MEGAFAC (registered trademark) F142D, MEGAFAC F171, MEGAFAC F172, MEGAFAC F173, MEGAFAC F177, MEGAFAC F183, MEGAFAC F554, MEGAFAC R30, MEGAFAC RS-718-K (manufactured by DIC Co., Ltd.), EFTOP (registered trademark) EF301, EFTOP EF303, EFTOP EF351, EFTOP EF352 (manufactured by Mitsubishi Materials Electronics & Chemicals Co., Ltd.), SURFLON (registered trademark) S381, SURFLON S382, SURFLON SC101, and SURFLON... SC105 (manufactured by AGC Corporation (formerly Asahi Glass Corporation)) and E5844 (manufactured by Daikin Fine Chemicals Research Institute Co., Ltd.), etc.

[0333] As examples of organosilicon surfactants containing fluorine atoms, surfactants with siloxane bonds and fluorocarbon chains within the molecule can be cited. Specifically, examples include MEGAFAC (registered trademark) R08, MEGAFAC BL20, MEGAFACF475, MEGAFAC F477, and MEGAFAC F443 (manufactured by DIC Corporation).

[0334] The leveling agent (F) content, relative to the total amount of the coloring and curing resin composition, is preferably 0.001% by mass to 0.2% by mass, more preferably 0.002% by mass to 0.1% by mass, and even more preferably 0.01% by mass to 0.05% by mass. It should be noted that this content does not include the aforementioned pigment dispersant content. If the leveling agent (F) content is within the aforementioned range, the flatness of the optical filter can be well achieved.

[0335] <Other Ingredients>

[0336] The coloring and curing resin composition of the present invention may include fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain-moving agents and other additives known in the art as needed.

[0337] <Method for manufacturing coloring and curing resin compositions>

[0338] The coloring and curing resin composition of the present invention can be prepared, for example, by mixing a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and a solvent (E), a leveling agent (F), a polymerization initiation aid (D1), and other components as needed.

[0339] Colorant (A) can also be prepared using the coloring dispersion and pigment dispersion described above. The remaining components can be mixed into the coloring dispersion and pigment dispersion to achieve a specified concentration, thereby preparing the target coloring curable resin composition.

[0340] For dyes that contain dyes, solutions can be prepared by pre-dissolving them separately in part or all of the solvent (E). Preferably, the solution is filtered using a filter with a pore size of about 0.01 to 1 μm.

[0341] Preferably, the mixed coloring and curing resin composition is filtered using a filter with a pore size of about 0.01 to 10 μm.

[0342] <Manufacturing Methods of Optical Filters>

[0343] Methods for manufacturing colored patterns from the color-curable resin composition of the present invention include photolithography, inkjet printing, and printing. Photolithography is preferred. The photolithography method involves coating the aforementioned color-curable resin composition onto a substrate, drying it to form a color composition layer, exposing the color composition layer through a photomask, and developing it. In the photolithography method, by not using a photomask during exposure and / or not developing, a colored coating film, which is a cured product of the aforementioned color composition layer, can be formed. The resulting colored pattern and colored coating film constitute the optical filter of the present invention.

[0344] The film thickness of the fabricated optical filter is not particularly limited and can be appropriately adjusted according to the purpose and application, for example, 0.1 to 30 μm, preferably 0.1 to 20 μm, and more preferably 0.5 to 6 μm.

[0345] As substrates, the following can be used: glass plates such as quartz glass, borosilicate glass, aluminosilicate glass, and soda-lime glass with a silica coating; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; silicon; and substrates on which aluminum, silver, or silver / copper / palladium alloy thin films are formed. Other optical filter layers, resin layers, transistors, circuits, etc., can also be formed on these substrates.

[0346] The formation of individual color pixels using photolithography can be carried out using known or conventional devices and conditions. For example, it can be fabricated in the following manner.

[0347] First, a coloring curable resin composition is coated onto a substrate, and volatile components such as solvents are removed by heating and drying (pre-baking) and / or vacuum drying, thereby obtaining a smooth coloring composition layer.

[0348] Examples of coating methods include spin coating, slot coating, and a combination of slot and spin coating.

[0349] The preferred temperature for heating and drying is 30–120°C, more preferably 50–110°C. The preferred heating time is 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.

[0350] When performing vacuum drying, it is preferable to carry out the process at a pressure of 50–150 Pa and a temperature range of 20–25 °C.

[0351] The film thickness of the coloring composition layer is not particularly limited, and can be appropriately selected according to the film thickness of the optical filter to be targeted.

[0352] Next, the coloring composition layer is exposed through a photomask used to form the target coloring pattern. The pattern on the photomask is not particularly limited and can be a pattern appropriate for the intended use.

[0353] The preferred light source for exposure is one that produces light with wavelengths in the range of 250–450 nm. For example, a filter that cuts off wavelengths less than 350 nm can be used to cut off this wavelength range; alternatively, a bandpass filter that extracts wavelengths around 436 nm, 408 nm, and 365 nm can be used to selectively extract light. Specifically, examples include mercury lamps, light-emitting diodes (LEDs), metal halide lamps, and halogen lamps.

[0354] In order to uniformly illuminate the entire exposure surface with parallel light and accurately align the photomask with the substrate on which the colored composition layer is formed, it is preferable to use exposure devices such as a mask aligner and a stepper.

[0355] A colored pattern is formed on a substrate by contacting the exposed coloring composition layer with a developing solution. During development, the unexposed portions of the coloring composition layer dissolve in the developing solution and are removed. As the developing solution, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide is preferred. 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. Furthermore, the developing solution may contain a surfactant.

[0356] The development method can be any of the following: spin-dip, immersion, or spray. Furthermore, the substrate can be tilted at any angle during development.

[0357] After development, it is preferable to wash with water.

[0358] Preferably, the obtained colored pattern is further baked. The post-baking temperature is preferably 150-250°C, more preferably 160-250°C. The post-baking time is preferably 1-120 minutes, more preferably 5-60 minutes.

[0359] The color-curable resin composition according to the present invention can be used to manufacture optical filters that are less prone to generating foreign matter. This optical filter is useful as a film for use in display devices (e.g., liquid crystal displays, organic EL devices, electronic paper, etc.) and solid-state imaging devices.

[0360] Example

[0361] The present invention will be described in more detail below with examples, but the present invention is not limited to the following examples. Of course, it can be implemented by appropriate modifications within the scope of the spirit described above and below, and all such modifications are included within the technical scope of the present invention. It should be noted that, unless otherwise specified, "parts" in the following text refers to "parts by mass" and "%" refers to "% by mass".

[0362] Synthesis example 1

[0363] A suitable amount of nitrogen was poured into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen. 340 parts of propylene glycol monomethyl ether acetate were then added, and the mixture was heated to 80°C while stirring. Next, 57 parts of acrylic acid and 3,4-epoxytricyclic acrylic acid [5.2.1.0] were added dropwise over 5 hours. 2,6 ] Decane-8-yl ester and 3,4-epoxytricyclic acrylate [5.2.1.0] 2,6 A mixture of decane-9-yl esters (containing 54 parts in a molar ratio of 1:1), 239 parts benzyl methacrylate, and 73 parts propylene glycol monomethyl ether acetate was prepared. On the other hand, a solution was prepared by dropwise addition of 40 parts of polymerization initiator 2,2-azobis(2,4-dimethylpentanonitrile) dissolved in 197 parts propylene glycol monomethyl ether acetate over 6 hours. After the addition of the initiator solution was completed, the solution was maintained at 80°C for 3 hours and then cooled to room temperature to obtain a copolymer (resin B-1) solution with a viscosity of 127 mPas and a solid content of 37.0%, as measured by a type B viscometer (23°C). The weight-average molecular weight (Mw) of the resulting copolymer was 9.4 × 10⁻⁶. 3 The dispersion is 1.89, and the acid value converted from solid components is 114 mg-KOH / g. Resin B-1 has the following structural units.

[0364]

[0365] Example 1

[0366] [Preparation of Coloring and Curing Resin Composition 1]

[0367] By mixing the following components, a coloring and curing resin composition 1 is obtained.

[0368] Colorant (A): 4.50 parts of phthalocyanine compound Pc-02 (compound 1) described in Material Example 1 of Japanese Patent Application Publication No. 2014-19838.

[0369] Resin (B): 23.6 parts of resin (B-1) obtained in Synthesis Example 1 (converted to solid state).

[0370] Polymerizable compound (C): (C-1) (Dipentaerythritol polyacrylate: trade name A-9550, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) 7.86 parts (on solid-state basis)

[0371] (C-2) (Trimethylolpropane triacrylate: trade name A-TMPT, manufactured by Shin-Nakamura Chemical Industry Co., Ltd.) 7.86 parts

[0372] Polymerization initiator (D): (D-1)N-acetyloxy-1-(4-phenylthiophenyl)-3-cyclohexylpropane-1-one-2-imine: trade name TR-PBG327 (manufactured by Changzhou Qiangli Electronic New Materials Co., Ltd.) 1.18 parts

[0373] Solvent (E): 52.4 parts of (E-1) propylene glycol monomethyl ether acetate

[0374] Solvent (E): 111 parts of (E-2) diethylene glycol ethyl methyl ether

[0375] Solvent (E): 91.6 parts of (E-3)N-methylpyrrolidone

[0376] Leveling agent (F): Polyether-modified silicone oil (TORAY SILICONE SH8400; manufactured by Toray Dow Corning Co., Ltd.) 0.045 parts

[0377]

[0378] Examples 2-10

[0379] [Preparation of coloring and curing resin compositions 2-10]

[0380] Except that the colorant (A) in Example 1 was replaced with the phthalocyanine compounds (compounds 2 to 10) described below, the coloring curable resin compositions 2 to 10 were obtained by the same method.

[0381] Example 2: Phthalocyanine compounds (1-5) (compound 2) described in Example 5 of WO2014 / 208514

[0382]

[0383] Example 3: Phthalocyanine compounds (1-3) described in Example 3 of WO2014 / 208514 (Compound 3)

[0384]

[0385] Example 4: Phthalocyanine compounds (1-8) (compound 4) described in Example 8 of WO2014 / 208514

[0386]

[0387] Example 5: Phthalocyanine compounds (1-2) (compound 5) described in Example 2 of WO2014 / 208514

[0388]

[0389] Example 6: The phthalocyanine compound (compound 6) of Example 93, which is the compound of chemical formula 11 described in Japanese Patent Application Publication No. 2013-108060, is synthesized from the compound of Example 8.

[0390]

[0391] Example 7: Phthalocyanine compounds (1-6) (compound 7) described in Example 6 of WO2014 / 115692

[0392]

[0393] Example 8: Phthalocyanine compounds (1-2) described in Example 2 of WO2014 / 115692 (Compound 8)

[0394]

[0395] Example 9: Phthalocyanine compounds (1-3) described in Example 3 of WO2014 / 115692 (Compound 9)

[0396]

[0397] Example 10: Phthalocyanine compounds (1-4) (Compound 10) described in Example 4 of WO2014 / 115692

[0398]

[0399] [Formation of Optical Filters (Method 1)]

[0400] The colored curable resin compositions 1-10 obtained in Examples 1-10 were stored at 40°C for one week. Each colored curable resin composition, after storage, was coated onto a 5cm square glass substrate (Eagle 2000; manufactured by Corning) using a spin-coating method. Then, a pre-baking process was performed at 100°C for 3 minutes to obtain an optical filter. Subsequently, the filter was baked in an oven at 230°C for 20 minutes to obtain the optical filter.

[0401] For the coloring and curing resin compositions 1 to 10 obtained in Examples 1 to 10, no foreign matter was observed in the optical filter.

[0402] Comparative Examples 1-3

[0403] [Preparation of coloring and curing resin compositions 1' to 3']

[0404] Except that the colorant (A) in Example 1 was replaced with the phthalocyanine compounds (compounds 11 to 13) described below, the coloring curable resin compositions 1' to 3' were obtained by the same method.

[0405] Comparative Example 1: The phthalocyanine compound (compound 11) described in Example 1 of Japanese Patent Application Publication No. 2010-160380.

[0406]

[0407] Comparative Example 2: The phthalocyanine compound (compound 12) described in Example 2 of Japanese Patent Application Publication No. 2010-160380.

[0408]

[0409] Comparative Example 3: Phthalocyanine compound (compound 13) described in Example 3 of Japanese Patent Application Publication No. 2010-160380.

[0410]

[0411] Reference Example 1

[0412] [Preparation of Coloring and Curing Resin Composition 11]

[0413] The components were mixed in such a manner as shown below to obtain the coloring and curing resin composition 11 of Reference Example 1. All components shown below, except for the solvent (E), are solid component equivalents.

[0414]

[0415] See Examples 2-10 and Examples 1'-3'

[0416] [Preparation of coloring and curing resin compositions 12-20 and 4'-6']

[0417] Except that the colorant (A) in Reference Example 1 was replaced with compounds 2 to 10 used in Examples 2 to 10 and compounds 11 to 13 used in Comparative Examples 1 to 3, the same procedure as in Reference Example 1 was followed to obtain coloring curable resin compositions 12 to 20 of Reference Examples 2 to 10 and coloring curable resin compositions 4' to 6' of Reference Examples 1' to 3'.

[0418] [Formation of Optical Filters (Method 2)]

[0419] The colored curable resin compositions 11-20 and 4'-6' obtained in Reference Examples 1-10 and Reference Examples 1'-3' were stored at 40°C for one week. Using spin coating, each colored curable resin composition was coated onto a 5cm square glass substrate (Eagle XG; manufactured by Corning) with a post-baking film thickness of 0.5μm. Then, the substrate was pre-baked at 70°C for 1 minute on a heated plate to obtain an optical filter. Subsequently, it was post-baked at 240°C for 9 minutes on a heated plate to obtain the optical filter.

[0420] The obtained optical filter was observed using an optical microscope to confirm whether any foreign objects larger than 10 μm were observed.

[0421] As a result, no foreign matter was observed in the optical filter for the coloring and curing resin compositions 11 to 20 obtained in Reference Examples 1 to 10, while foreign matter was observed in the optical filter for the coloring and curing resin compositions 4' to 6' obtained in Reference Examples 1' to 3'.

Claims

1. A coloring and curing resin composition comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator. The colorant is a colorant containing a compound represented by formula (II). In equation (II), Z 1 and Z 2 Each can be independently represented by an oxygen atom, a sulfur atom, or NR. 4 ; R 4 The alkyl group represents a group containing 1 to 10 hydrogen atoms or carbon atoms, wherein the methylene group contained in the alkyl group may optionally be replaced with an oxygen atom; Ar 1 It represents an arylene with 6 to 20 carbon atoms or a heteroarylene with 3 to 20 carbon atoms, wherein the hydrogen atoms contained in the arylene and heteroarylene are optionally replaced by halogen atoms or alkoxy groups with 1 to 20 carbon atoms; Z 3 and Z 4 Each independently represents a hydrogen atom, N(R) 6 2. OR 5 or SR 5 ; R 5 The alkyl group having 1 to 20 carbon atoms, the aryl group having 6 to 20 carbon atoms, or the heteroaryl group having 3 to 20 carbon atoms, wherein the hydrogen atom contained in the alkyl group is optionally replaced by a halogen atom, the methylene group contained in the alkyl group is optionally replaced by an oxygen atom, and the hydrogen atom contained in the aryl group and the heteroaryl group is optionally replaced by a halogen atom or an alkoxy group having 1 to 20 carbon atoms. R 6 The alkyl group represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms (the hydrogen atom contained in the alkyl group may optionally be replaced by an aryl group having 6 to 10 carbon atoms, and the methylene group contained in the alkyl group may optionally be replaced by an oxygen atom); There are multiple Z in one molecule. 1 Z 2 Z 3 Z 4 Ar 1 R 4 R 5 or R 6 In some cases, they may be the same or different from each other; M 2 It represents a hydrogen atom, a monovalent metal atom, a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, or an oxide metal atom; M 2 When n is a hydrogen atom or a monovalent metal atom, n is 2, and M is 2. 2 When the atom is a divalent metal atom, a trivalent substituted metal atom, a tetravalent substituted metal atom, or an oxidized metal atom, n is 1; *d, *d1, *d2, *e, *e1, *e2, *f1, and *f2 all represent chemical bonds. One of the two *d bonds is bonded to *d1, and the other to *d2; one of the two *e bonds is bonded to *e1, and the other to *e2; *f1 and *f2 are bonded to M. 2 Bonding.

2. The coloring and curing resin composition according to claim 1, wherein, The resin is a copolymer comprising structural units selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides, and structural units having a cyclic ether structure having 2 to 4 carbon atoms and an olefinic unsaturated bond.

3. An optical filter formed from the coloring and curing resin composition of claim 1 or 2.

4. A solid-state imaging device comprising the optical filter of claim 3.

Images