Colored curable resin composition, color filter, and display device

Abstract

To provide a colored curable resin composition capable of forming a color filter excellent in light fastness.SOLUTION: A colored curable resin composition contains a colorant, a resin, a polymerizable compound, and a polymerization initiator. The colorant includes an anthraquinone dye having a carboxy group, and at least one selected from the group consisting of squarylium dyes and coumarin dyes.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a colored curable resin composition, a color filter, and a display device. [Background technology]

[0002] Color filters used in displays such as liquid crystal displays, electroluminescent displays, and plasma displays, and solid-state imaging devices such as CCD and CMOS sensors, are manufactured from colored curable resin compositions. Known examples of such colored curable resin compositions include a composition containing a squarylium compound as a colorant (Patent Document 1) and a composition containing a coumarin compound as a colorant (Patent Document 2). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] JP 2015-86379 A [Patent Document 2] JP 2015-44982 A Summary of the Invention [Problem to be solved by the invention]

[0004] However, color filters formed from the above-mentioned conventionally known colored curable resin compositions do not have fully satisfactory light resistance. [Means for solving the problem]

[0005] The gist of the present invention is as follows. [1] A composition comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator; A colored curable resin composition, comprising a colorant comprising at least one dye selected from the group consisting of squarylium dyes and coumarin dyes, and an anthraquinone dye having a carboxy group. [2] The colored curable resin composition according to [1], wherein the anthraquinone dye having a carboxy group is a compound represented by formula (A1). [ka] [In formula (A1), A 1a and A 2a each independently represents a phenylene group which may have a substituent. L 1a and L 2a each independently represents a divalent hydrocarbon group having 1 to 15 carbon atoms, and -CH2- contained in the hydrocarbon group is -O-, -SO2- or -NR 11a However, adjacent -CH2- cannot be simultaneously replaced with the same group. R 1a ~R 6a R each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 8 carbon atoms. 11a represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.] [3] A color filter formed from the colored curable resin composition according to [1] or [2]. [4] A display device comprising the color filter according to [3]. Effect of the Invention

[0006] According to the colored curable resin composition of the present invention, a color filter having excellent light resistance can be formed. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0007] The colored curable resin composition of the present invention contains a colorant (hereinafter, may be referred to as colorant (A)), a resin (hereinafter, may be referred to as resin (B)), a polymerizable compound (hereinafter, may be referred to as polymerizable compound (C)), and a polymerization initiator (hereinafter, may be referred to as polymerization initiator (D)). It is preferable that the colored curable resin composition of the present invention further contains a solvent (hereinafter, sometimes referred to as solvent (E)). The colored curable resin composition of the present invention may contain a leveling agent. In this specification, the compounds exemplified as each component may be used alone or in combination of two or more kinds, unless otherwise specified.

[0008] <Colorant (A)> The colorant contains at least one selected from the group consisting of squarylium dyes and coumarin dyes, and an anthraquinone dye having a carboxy group, and is preferably a combination of a squarylium dye and an anthraquinone dye having a carboxy group, a combination of a coumarin dye and an anthraquinone dye having a carboxy group, or a combination of a squarylium dye, a coumarin dye and an anthraquinone dye having a carboxy group. Each of the squarylium dyes, coumarin dyes, and anthraquinone dyes having a carboxy group described below may be one or more kinds.

[0009] <Anthraquinone dyes with carboxy groups> The anthraquinone dye having a carboxy group may be a compound having at least one (preferably two) carboxy groups, and is preferably a compound represented by formula (A1).

[0010] [ka] [In formula (A1), A 1a and A 2a each independently represents a phenylene group which may have a substituent. L 1a and L 2a each independently represents a divalent hydrocarbon group having 1 to 15 carbon atoms, and -CH2- contained in the hydrocarbon group is -O-, -SO2- or -NR 11a However, adjacent -CH2- cannot be simultaneously replaced with the same group. R 1a ~R 6a R each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 8 carbon atoms. 11a represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.]

[0011] A 1a and A 2a The substituents which the phenylene group represented by the formula (I) may have include a halogen atom, -R 21a , -OH, -OR 21a , -SO3H, -SO3 - G + , -COOH, -COO - T + , -CO2R 21a , -SR 21a , -SO2R 21a , -SO3R 21a or -SO2NR 12a R 13a The above-mentioned R 21a represents a saturated hydrocarbon group having 1 to 20 carbon atoms, -R 21a R in the case 21a is preferably an alkyl group having 1 to 8 carbon atoms. 12a and R 13a each independently represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms; R 12a and R 13a may be joined together to form a ring containing the nitrogen atom. + is Na + , K + , or N + (R 15a )4, and T + is Na + , K + , or N + (R 16a )4, and the four R 15a may be the same or different, and the four R 16a may be the same or different. 15a and R 16a represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.

[0012] A 1a and A 2a a halogen atom as a substituent which may be contained in the phenylene group represented by the formula: 1a ~R 6aExamples of the halogen atom represented by the formula (I) include a chlorine atom, a bromine atom, a fluorine atom, and an iodine atom, and among these, a chlorine atom and a bromine atom are preferred.

[0013] A 1a and A 2a The substituent that the phenylene group represented by the formula (I) may have is, for example, -R 21a , -SO3H, -SO3 - G + , -COOH, -COO - T + and -SO2NR 12a R 13a is preferred, in which case -SO3 - G + As for -SO3 - N + (R 15a )4 is preferred. The most preferred substituent is -R 21a It is.

[0014] R 1a ~R 6a , R 11a , R 15a , R 16a , and R 21a Examples of the alkyl group having 1 to 8 carbon atoms represented by the formula (I) include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, and hexyl groups; and branched alkyl groups such as isopropyl, isobutyl, isopentyl, and neopentyl groups. 1a ~R 6a , and R 11a R is preferably a hydrogen atom. 21a The alkyl group having 1 to 8 carbon atoms represented by the following formula is more preferably a methyl group, an ethyl group, a propyl group, or a butyl group, and even more preferably a methyl group or an ethyl group. The substitution position in the phenylene group may be any position except for the two bonds, and two or more positions may be substituted. When two or more positions are substituted, the substituents may be the same or different.

[0015] R 12a , R 13a , and R21a Examples of the saturated hydrocarbon group having 1 to 20 carbon atoms represented by the formula (1) include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, and icosyl; branched alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl; and alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and tricyclodecyl. The number of carbon atoms in the saturated hydrocarbon group is more preferably 1 to 10, even more preferably 1 to 8, and even more preferably 1 to 5.

[0016] R 12a and R 13a Examples of the aralkyl group having 7 to 10 carbon atoms represented by the following formula include a benzyl group, a phenylethyl group, and a phenylbutyl group.

[0017] R 12a and R 13a Examples of the ring containing a nitrogen atom formed by combining with each other include the following: In the formula, * represents a bond.

[0018] [ka]

[0019] N + (R 15a )4, N + (R 16a ) 4 includes tetramethylammonium, tetraethylammonium, tetrapropylammonium, tetrabutylammonium, and the like.

[0020] -OR 21a Examples of the alkyloxy group include alkyloxy groups such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group, and an icosyloxy group. -CO2R 21a Examples of the alkyloxycarbonyl group include alkyloxycarbonyl groups such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a hexyloxycarbonyl group, and an icosyloxycarbonyl group.

[0021] -SR 21a Examples of the alkylsulfanyl group include alkylsulfanyl groups such as methylsulfanyl group, ethylsulfanyl group, butylsulfanyl group, hexylsulfanyl group, decylsulfanyl group and icosylsulfanyl group. -SO2R 21a Examples of the sulfonyl group include alkylsulfonyl groups such as a methylsulfonyl group, an ethylsulfonyl group, a butylsulfonyl group, a hexylsulfonyl group, a decylsulfonyl group, and an icosylsulfonyl group. -SO3R 21a Examples of the sulfonyl group include alkyloxysulfonyl groups such as a methoxysulfonyl group, an ethoxysulfonyl group, a propoxysulfonyl group, a tert-butoxysulfonyl group, a hexyloxysulfonyl group, and an icosyloxysulfonyl group.

[0022] -SO2NR 12a R 13a Examples of the alkyl group include a sulfamoyl group; N-Methylsulfamoyl group, N-Ethylsulfamoyl group, N-Propylsulfamoyl group, N-Isopropylsulfamoyl group, N-Butylsulfamoyl group, N-Isobutylsulfamoyl group, N-Sec-Butylsulfamoyl group, N-Tert-Butylsulfamoyl group, N-Pentylsulfamoyl group, N-(1-Ethylpropyl)sulfamoyl group, N-(1,1-Dimethylpropyl)sulfamoyl group, N-(1,2-Dimethylpropyl)sulfamoyl group, N-(2,2-Dimethylpropyl)sulfamoyl group, N-(1-Methylbutyl)sulfamoyl group, N-(2-Methylbutyl)sulfamoyl group, N-1 substituted sulfamoyl groups such as amoyl group, N-(3-methylbutyl)sulfamoyl group, N-cyclopentylsulfamoyl group, N-hexylsulfamoyl group, N-(1,3-dimethylbutyl)sulfamoyl group, N-(3,3-dimethylbutyl)sulfamoyl group, N-heptylsulfamoyl group, N-(1-methylhexyl)sulfamoyl group, N-(1,4-dimethylpentyl)sulfamoyl group, N-octylsulfamoyl group, N-(2-ethylhexyl)sulfamoyl group, N-(1,5-dimethylhexyl)sulfamoyl group, and N-(1,1,2,2-tetramethylbutyl)sulfamoyl group; Examples of N,N-disubstituted sulfamoyl groups include N,N-dimethylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-diethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-isopropylmethylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N-butylethylsulfamoyl group, N,N-bis(1-methylpropyl)sulfamoyl group, and N,N-heptylmethylsulfamoyl group.

[0023] L 1a and L 2aExamples of the divalent hydrocarbon having 1 to 15 carbon atoms and forming the group represented by the formula (1) include aliphatic hydrocarbons having 1 to 12 carbon atoms, aromatic hydrocarbons having 6 to 15 carbon atoms, such as benzene and benzene having an alkyl group having 1 to 8 carbon atoms. Examples of the divalent aliphatic hydrocarbon group having 1 to 15 carbon atoms include linear alkanediyl groups having bonds at both ends, such as methylene group, ethane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, and hexane-1,6-diyl group, ethane-1,1-diyl group, propane-1,1-diyl group, propane-1,2-diyl group, propane-2,2-diyl group, butane-1,1-diyl group, butane-1,2-diyl group, butane-1,3-diyl group, butane-2,2-diyl group, butane-2,3-diyl group, 2-methyl Examples of the alkanediyl group include branched alkanediyl groups such as propane-1,1-diyl group, 2-methylpropane-1,2-diyl group, 2-methylpropane-1,3-diyl group, 2-methylbutane-1,4-diyl group, 2-methylbutane-2,3-diyl group, 2-methylbutane-2,4-diyl group, 2-methylbutane-3,3-diyl group, 2-methylbutane-3,4-diyl group, and 2-methylbutane-4,4-diyl group, and cyclic alkanediyl groups such as cyclohexane-1,4-diyl group and cyclohexane-1,4-dimethylene group, and among these, linear alkanediyl groups are preferred.

[0024] Examples of benzene having an alkyl group with 1 to 8 carbon atoms leading to a divalent aromatic hydrocarbon group with 6 to 15 carbon atoms include methylbenzene, dimethylbenzene, ethylbenzene, propylbenzene, ethyl(methyl)benzene, butylbenzene, and ethyl(dimethyl)benzene, and the divalent group formed by removing two hydrogen atoms from the benzene having an alkyl group with 1 to 8 carbon atoms may have two bonds on the alkyl group, two bonds on the benzene ring, or one bond on the alkyl group and one bond on the benzene ring. Among these, the preferred embodiment has one bond on the alkyl group and one bond on the benzene ring.

[0025] L 1a and L2a The divalent hydrocarbon group represented by the following formula (I) preferably has 2 to 15 carbon atoms, more preferably 3 to 13 carbon atoms, and further preferably 4 to 11 carbon atoms. The -CH2- contained in the hydrocarbon group is -O-, -SO2- or -NR 11a Although they may be substituted with -, the number of carbon atoms in the hydrocarbon group is defined as the number of carbon atoms before being substituted with these groups. Among them, L 1a and L 2a It is particularly preferred that the divalent hydrocarbon group represented by the following formula (I) is a divalent group formed by removing two hydrogen atoms from a benzene group having an alkyl group having 1 to 8 carbon atoms, and it is particularly preferred that the alkyl group has one bond and the benzene ring has one bond. One bond of the alkyl group is A 1a Or A 2a and one bond of the benzene ring is preferably bonded to CO2H.

[0026] As the anthraquinone dye, there may be mentioned the following: 1a -**(* is A 1a represents a bond to CO2H, and ** represents a bond to CO2H) and *-L 2a -**(* is A 2a In another embodiment, the compound in which each of the structures represented by formulae (A1a) to (A1h) is independently any one of the structures represented by formulae (A1a) to (A1h) is preferable.

[0027] *-OR 31a -** (A1a) *-OR 32a -** (A1b) *-OR 33a -R 32a -** (A1c) *-OR 32a -R 33a -** (A1d) *-SO2-NH-R 31a -** (A1e) *-SO2-NH-R 34a -** (A1f) *-SO2-NH-R33a -R 34a -** (A1g) *-SO2-NH-R 34a -R 33a -** (A1h) [In the formula, R 31a represents an alkanediyl group having 1 to 10 carbon atoms, R 32a and R 34a represents a phenylene group which may have an alkyl group having 1 to 4 carbon atoms bonded thereto, R 33a represents an alkanediyl group having 1 to 4 carbon atoms. 32a has 14 or less carbon atoms, and R 33a The number of carbon atoms in R is 13 or less. 32a and R 33a The sum of the carbon numbers of R is 14 or less. 33a and R 34a The sum of the carbon numbers is 13 or less. * indicates A 1a Or A 2a represents a bond to the , and ** represents a bond to CO2H.]

[0028] R 31a and an alkanediyl group having 1 to 10 carbon atoms represented by the formula: 33a The alkanediyl group having 1 to 4 carbon atoms represented by the formula: 1a and L 2a The divalent hydrocarbon group may be the same as those exemplified by the divalent hydrocarbon group represented by the following formula (preferably the divalent saturated hydrocarbon group). R 32a and R 34a The phenylene group having an alkyl group of 1 to 4 carbon atoms, represented by the following formula (I) which may be bonded thereto, may be the same as a benzene group having an alkyl group of 1 to 8 carbon atoms, and may be the same as one having two bonds to the benzene. R 32a and R 34a is more preferably a 6-methyl-1,3-phenylene group, a 5-methyl-1,3-phenylene group, or a 4-methyl-1,3-phenylene group.

[0029] Among (A1a) to (A1h), (A1a), (A1f) and the like are preferred.

[0030] The anthraquinone dye includes a compound represented by the formula (A1X). Specific examples of the compound represented by the formula (A1X) are represented by the numbers (A1X-1) to (A1X-36) in Table 1.

[0031] [ka]

[0032] [Table 1]

[0033] In Table 1, Me represents a methyl group, and RX1 to RX5 and RY1 to RY4 represent groups represented by the following formulae, respectively: In the following formulae, * represents a bond.

[0034] [ka]

[0035] Among these, the compounds represented by the numbers (A1X-6) to (A1X-9), the compounds represented by the numbers (A1X-15) to (A1X-18), the compounds represented by the numbers (A1X-24) to (A1X-27), and the compounds represented by the numbers (A1X-33) to (A1X-36) are more preferred.

[0036] The anthraquinone compound (A1) can be produced according to a known method.

[0037] The content of the anthraquinone dye is, relative to the total amount of the colorant (A), for example, 5 mass% or more, preferably 10 mass% or more, and more preferably 15 mass% or more, and for example, 50 mass% or less, preferably 45 mass% or less, and more preferably 40 mass% or less.

[0038] The content of the anthraquinone dye is, relative to the solid content of the colored curable resin composition, for example, 1 mass% or more, preferably 2 mass% or more, more preferably 3 mass% or more, and for example, 30 mass% or less, preferably 25 mass% or less, more preferably 20 mass% or less.

[0039] <Squarylium dye> The squarylium dye is preferably a compound represented by formula (A1-2').

[0040] [ka] [In formula (A1-2'), A + and B each independently represent an organic group containing an aromatic ring or a heterocyclic ring. The compound represented by formula (A1-2') also includes compounds having all possible resonance structures with respect to the structure represented by formula (A1-2').

[0041] Examples of squarylium compounds represented by formula (A1-2') include those described in JP 2013-76926 A. Among the squarylium compounds represented by formula (A1-2'), those represented by formula (A1-2) are preferred.

[0042] [ka]

[0043] [In formula (A1-2), R 1 ~R 4each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms. A hydrogen atom contained in the monovalent saturated hydrocarbon group may be substituted with a halogen atom, a hydroxyl group, or an alkylamino group having 1 to 8 carbon atoms, and -CH2- constituting the monovalent saturated hydrocarbon group may be substituted with -O- or -S-. However, adjacent -CH2- are not simultaneously substituted with the same type of group, and the terminal -CH2- is not substituted. R 5 ~R 8 each independently represents a hydrogen atom or a hydroxy group. R 9 and R 10 each independently represents a phenyl group which may be substituted with a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms. R 11 and R 12 each independently represents a phenyl group which may be substituted with a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom, a hydroxyl group, or an amino group substituted with one or two alkyl groups having 1 to 8 carbon atoms, and -CH2- constituting the saturated hydrocarbon group may be replaced with -O- or -S-, provided that adjacent -CH2- are not simultaneously substituted with the same type of group, and the terminal -CH2- is not substituted.]

[0044] R 1 ~R 4 The halogen atom in the formula (I) includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0045] R 1 ~R 4 , R 11 and R 12Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in the formula (I) include linear alkyl groups having 1 to 20 carbon atoms, such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, and icosyl groups; branched alkyl groups having 3 to 20 carbon atoms, such as isopropyl, isobutyl, sec-butyl, tert-butyl, isopentyl, neopentyl, and 2-ethylhexyl groups; and alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms, such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and tricyclodecyl groups. R 1 ~R 4 , R 11 and R 12 The monovalent saturated hydrocarbon group in preferably has 1 to 18 carbon atoms, more preferably 2 to 15 carbon atoms, further preferably 2 to 12 carbon atoms, and even more preferably 3 to 9 carbon atoms.

[0046] Examples of groups in which a hydrogen atom contained in these saturated hydrocarbon groups has been substituted with a halogen atom include a trifluoromethyl group, a trifluoroethyl group, a fluoroethyl group, a chloroethyl group, a pentafluorobutyl group, a fluorobutyl group, a chlorobutyl group, a heptafluorobutyl group, a fluorohexyl group, and a chlorohexyl group. Examples of the group in which a hydrogen atom contained in a saturated hydrocarbon group is substituted with a hydroxy group include a hydroxyethyl group, a hydroxybutyl group, and a hydroxyhexyl group. Examples of the group in which a hydrogen atom contained in a saturated hydrocarbon group is substituted with an amino group substituted with one or two alkyl groups having 1 to 8 carbon atoms include an N,N-dimethylaminoethyl group, an N,N-diethylaminobutyl group, and an N,N-dibutylaminohexyl group.

[0047] Examples of monovalent saturated hydrocarbon groups in which -CH2- is replaced with -O- or -S- include groups represented by the following formula: In the following formula, * represents a bond.

[0048] [ka]

[0049] R 9 and R 10 In the above formula, examples of the monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms that may substitute for the phenyl group include the above-mentioned monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, as well as monovalent unsaturated hydrocarbon groups having 2 to 20 carbon atoms. Examples of the unsaturated hydrocarbon group include a vinyl group, a propenyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a nonenyl group, and a decenyl group. Among these, alkyl groups having 1 to 4 carbon atoms are preferred, and methyl and ethyl groups are more preferred.

[0050] Examples of the phenyl group which may be substituted with a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms include a phenyl group, a toluyl group, and a group represented by the following formula, in which * represents the bond to the nitrogen atom.

[0051] [ka]

[0052] R 1 ~R 4 are each independently preferably a hydrogen atom, a hydroxyl group, or a methyl group, and more preferably a hydrogen atom. R 5 ~R 8 are each independently preferably a hydrogen atom, a hydroxyl group, or a methyl group, more preferably a hydrogen atom or a hydroxyl group. 5 and R 8 is a hydroxy group. R 9 and R 10 are each independently preferably a phenyl group or a phenyl group substituted with one or more alkyl groups having 1 to 4 carbon atoms, and more preferably a phenyl group or a phenyl group having one or more methyl groups and / or ethyl groups as substituents.

[0053] R 11 and R 12 is preferably a phenyl group which may be substituted with a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, more preferably a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, even more preferably a monovalent saturated hydrocarbon group having 2 to 18 carbon atoms, still more preferably a monovalent saturated hydrocarbon group having 3 to 15 carbon atoms, even more preferably a monovalent saturated hydrocarbon group having 4 to 12 carbon atoms, and particularly preferably a butyl group or a 2-ethylhexyl group.

[0054] In formula (A1-2),

[0055] [ka] and

[0056] [ka] Examples of the group include groups represented by formulae (A2-1) to (A2-8) and groups represented by formulae (B2-1) to (B2-8). * represents a bond to a carbon atom.

[0057] [ka]

[0058] [ka]

[0059] Examples of the compound represented by formula (A1-2) include compounds (C2-1) to (C2-24) shown in Table 2 and compounds (D2-1) to (D2-24) shown in Table 3.

[0060] [Table 2]

[0061] [Table 3]

[0062] From the viewpoint of availability of raw materials, compounds (C2-9) to (C2-16) and compounds (D2-9) to (D2-16) are preferred, and compound (C2-9) (a compound represented by formula (AII-8) described later) and compound (D2-9) (a compound represented by formula (AII-X) described later) are more preferred.

[0063] The compound represented by formula (A1-2) can be produced, for example, by the method described in JP-A No. 2002-363434.

[0064] The content of the squarylium dye, relative to the total amount of the colorant (A), is, for example, 10 mass% or more, preferably 20 mass% or more, more preferably 30 mass% or more, and for example, 95 mass% or less, preferably 90 mass% or less, more preferably 80 mass% or less.

[0065] The content of the squarylium dye, relative to the solid content of the colored curable resin composition, is, for example, 2 mass% or more, preferably 4 mass% or more, and more preferably 6 mass% or more, and for example, 60 mass% or less, preferably 50 mass% or less, and more preferably 40 mass% or less.

[0066] <Coumarin dye> The coumarin dye may be any compound having a coumarin skeleton in the molecule. Examples of the coumarin dye include CI Acid Yellow 227, 250; CI Disperse Yellow 82, 184; CI Solvent Orange 112; CI Solvent Yellow 160, 172; and the coumarin compounds described in Japanese Patent No. 1299948, JP 2013-151668, JP 2013-231165, JP 2014-51641, JP 2015-44982, and WO 2014 / 208767.

[0067] The coumarin dye is preferably a compound represented by formula (A1-3) and / or a compound represented by formula (A1-4).

[0068] [ka]

[0069] [In formula (A1-3), R 71 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. R 72 and R 73 each independently represents a halogen atom, an alkoxy group, an amino group which may have a substituent, or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. s represents an integer of 0 to 3, and when s is an integer of 2 or more, a plurality of R 72 may be the same or different. t represents an integer of 0 to 4, and when t is an integer of 2 or more, a plurality of R 73 may be the same or different.]

[0070] R 71 ~R 73Examples of the hydrocarbon group in include an aliphatic hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated, and examples thereof include an alkyl group, an alkenyl group, and an alkynyl group. The alicyclic hydrocarbon group may be saturated or unsaturated, and examples thereof include a cycloalkyl group, a cycloalkenyl group, a condensed polycyclic hydrocarbon group, a bridged ring hydrocarbon group, a spiro hydrocarbon group, and a cyclic terpene hydrocarbon group. Examples of the aromatic hydrocarbon group include a phenyl group and a triyl group. Among them, an alkyl group having 1 to 8 carbon atoms is preferable, and an alkyl group having 1 to 4 carbon atoms is more preferable. Examples of the substituent of the hydrocarbon group include a halogen atom, an alkoxy group having 1 to 8 carbon atoms, a hydroxy group, a nitro group, a carboxy group, a sulfo group, a sulfamoyl group, a carbamoyl group, an N-substituted sulfamoyl group, an alkyloxycarbonyl group, etc. When the substituent has a sulfo group, the sulfo group may be in the form of a salt. R 72 and R 73 Examples of the halogen atom in include a chlorine atom, a fluorine atom, a bromine atom, and an iodine atom. R 72 and R 73 The alkoxy group in is preferably an alkoxy group having 1 to 8 carbon atoms, and more preferably an alkoxy group having 1 to 4 carbon atoms. R 72 and R 73 The amino group in the formula (I) preferably has a substituent, and the N-position substituent is preferably an alkyl group having 1 to 8 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms. s is preferably 1, in which case R 72 is preferably a substituted amino group, more preferably a dialkyl-substituted amino group, and further preferably a dialkyl-substituted amino group substituted with an alkyl group having 1 to 8 carbon atoms. It is preferred that t is 0.

[0071] Specific examples of the compound represented by formula (A1-3) include compounds represented by formula (A1-3-1) or (A1-3-2).

[0072] [ka]

[0073] The compound represented by formula (A1-4) (hereinafter also referred to as (A1-4) compound) is as follows. [ka] (In the formula, L represents a divalent fluorinated hydrocarbon group having 1 to 20 carbon atoms, a divalent hydrocarbon group having 1 to 20 carbon atoms, or a sulfonyl group (-SO2-), X represents an oxygen atom or a sulfur atom, R 7 ~R 13 each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carbamoyl group (-CONH2), a sulfamoyl group (-SO2NH2), -SO3M, -CO2M, a hydroxyl group, a formyl group, an amino group, or a monovalent hydrocarbon group having 1 to 20 carbon atoms, and -CH2- constituting the hydrocarbon group is an oxygen atom, a sulfur atom, -N(R 14 )-, a sulfonyl group or a carbonyl group, and a hydrogen atom contained in the hydrocarbon group may be replaced by a halogen atom, a cyano group, a nitro group, a carbamoyl group, a sulfamoyl group, -SO3M, -CO2M, a hydroxy group, a formyl group or an amino group, and R 14 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms; R 14 When a plurality of M's are present, they may be the same or different. M represents a hydrogen atom or an alkali metal atom. When a plurality of M's are present, they may be the same or different. Z is represented by the formula (Z1):

[0074] [ka] (In the formula, R 1 represents an alkyl group having 1 to 20 carbon atoms, in which -CH2- constituting the alkyl group may be replaced by an oxygen atom, R 2 ~R 6each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carbamoyl group, a sulfamoyl group, -SO3M, -CO2M, a hydroxyl group, a formyl group, an amino group, or a monovalent hydrocarbon group having 1 to 20 carbon atoms, and -CH2- constituting the hydrocarbon group is an oxygen atom, a sulfur atom, -N(R 30 )-, a sulfonyl group or a carbonyl group, and a hydrogen atom contained in the hydrocarbon group may be replaced by a halogen atom, a cyano group, a nitro group, a carbamoyl group, a sulfamoyl group, -SO3M, -CO2M, a hydroxy group, a formyl group or an amino group, and R 30 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms; R 30 When there are a plurality of M's, they may be the same or different, M represents a hydrogen atom or an alkali metal atom, when there are a plurality of M's, they may be the same or different, and * represents a bond.

[0075] In formula (A1-4), L represents a divalent fluorinated hydrocarbon group having 1 to 20 carbon atoms, a divalent hydrocarbon group having 1 to 20 carbon atoms, or a sulfonyl group (—SO2—). Examples of the divalent fluorinated hydrocarbon group having 1 to 20 carbon atoms include groups represented by formulae (L1) to (L12). From the viewpoint of availability of raw materials, groups represented by formulae (L1), (L7), (L8), (L10) or (L11) are preferred, groups represented by formulae (L1), (L7), (L8) or (L11) are more preferred, and groups represented by formula (L1) are particularly preferred. In the following formulae (L1) to (L12), ● represents a bond.

[0076] [ka]

[0077] Examples of the divalent hydrocarbon group having 1 to 20 carbon atoms include a methylene group, a dimethylene group, a trimethylene group, a tetramethylene group, a 1,1-ethylene group, a 2,2-propylene group, and a fluorene-9,9-diyl group, and a divalent hydrocarbon group having 1 to 16 carbon atoms is preferred.

[0078] From the viewpoint of the thermal stability of compound (A1-4), L is preferably a divalent hydrocarbon group having 1 to 16 carbon atoms or a sulfonyl group, and from the viewpoint of availability of raw materials, L is more preferably a group represented by any one of the following formulae (L21) to (L24), further preferably a group represented by any one of the formulae (L21) to (L23), and particularly preferably a group represented by formula (L21) or formula (L22). In the following formulae, ● represents a bond.

[0079] [ka]

[0080] In formula (A1-4), X represents an oxygen atom or a sulfur atom, and is preferably an oxygen atom. A color filter formed from a colored curable resin composition containing a colorant containing a compound (A1-4) in which X is an oxygen atom tends to have high brightness.

[0081] In formula (A1-4), R 7 ~R 13 each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carbamoyl group, a sulfamoyl group, -SO3M, -CO2M, a hydroxyl group, a formyl group, an amino group, or a monovalent hydrocarbon group having 1 to 20 carbon atoms, and -CH2- constituting the hydrocarbon group is an oxygen atom, a sulfur atom, -N(R 14 A hydrogen atom contained in the hydrocarbon group may be replaced by a halogen atom, a cyano group, a nitro group, a carbamoyl group (-CONH2), a sulfamoyl group (-SO2NH2), -SO3M, -CO2M, a hydroxy group, a formyl group or an amino group; R 14 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms; R14 When multiple are present, they may be the same or different.

[0082] M represents a hydrogen atom or an alkali metal atom, and when there are a plurality of M's, they may be the same or different. Examples of alkali metal atoms include sodium and potassium atoms. M is preferably a hydrogen atom. Halogen atoms include fluorine, chlorine, bromine and iodine atoms.

[0083] Examples of the monovalent hydrocarbon group having 1 to 20 carbon atoms include: aliphatic hydrocarbon groups such as a methyl group, an ethyl group, a propyl group, an isopropyl group, an isopropenyl group, a 1-propenyl group, a 2-propenyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a 2-ethyl-1-butyl group, a 2-butenyl group, a 1,3-butadienyl group, a pentyl group, an isopentyl group, a 3-pentyl group, a neopentyl group, a tert-pentyl group, a 1-methyl-1-pentyl group, a 2-methyl-1-pentyl group, a 2-pentenyl group, a 3-ethyl-1-pentyl group, a hexyl group, an isohexyl group, a 5-methyl-1-hexyl group, a 2-ethyl-1-hexyl group, a heptyl group, a 3-ethyl-1-heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, or an octadecyl group; cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclohexenyl group, cycloheptyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group, 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, alicyclic hydrocarbon groups such as a 2,5-dimethylcyclohexyl group, a 2,6-dimethylcyclohexyl group, a 3,4-dimethylcyclohexyl group, a 3,5-dimethylcyclohexyl group, a 2,2-dimethylcyclohexyl group, a 3,3-dimethylcyclohexyl group, a 4,4-dimethylcyclohexyl group, a 2,4,6-trimethylcyclohexyl group, a 2,2,6,6-tetramethylcyclohexyl group, and a 3,3,5,5-tetramethylcyclohexyl group; Aromatic hydrocarbon groups such as phenyl, o-tolyl, m-tolyl, p-tolyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, mesityl, o-cumenyl, m-cumenyl, p-cumenyl, 2,6-di(2-propyl)phenyl, 1-naphthyl, 2-naphthyl, and biphenyl groups; and Examples of the groups include groups formed by combining two or more of the above groups, such as a cyclohexylmethyl group, a benzyl group, and a phenethyl group.

[0084] The -CH- constituting such a monovalent hydrocarbon group is an oxygen atom, a sulfur atom, -N(R 14 )-, a sulfonyl group or a carbonyl group, and a group in which a hydrogen atom in such a monovalent hydrocarbon group is replaced by a halogen atom, a cyano group, a nitro group, a carbamoyl group, a sulfamoyl group, -SO3M, -CO2M, a hydroxy group, a formyl group or an amino group include: Alkoxy groups such as a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, and a (2-ethyl-1-hexyl)oxy group; Aryloxy groups such as a phenoxy group; aralkyloxy groups such as a benzyloxy group; Acetyl group, ethylcarbonyl group, propylcarbonyl group, isopropylcarbonyl group, isopropenylcarbonyl group, 1-propenylcarbonyl group, 2-propenylcarbonyl group, butylcarbonyl group, isobutylcarbonyl group, sec-butylcarbonyl group, tert-butylcarbonyl group, (1-ethyl-1-butyl)carbonyl group, (2-ethyl-1-butyl)carbonyl group, 2-butenylcarbonyl group, 1,3-butadienylcarbonyl group, pentylcarbonyl group, isopentylcarbonyl group, 3-pentylcarbonyl group, neopentylcarbonyl group, tert-pentylcarbonyl group, (1-methyl-1-pentyl)carbonyl group, (2-methyl-1 acyl groups such as a (1-ethyl-1-pentyl)carbonyl group, a 2-pentenylcarbonyl group, a (1-ethyl-1-pentyl)carbonyl group, a (3-ethyl-1-pentyl)carbonyl group, a hexylcarbonyl group, an isohexylcarbonyl group, a (5-methyl-1-hexyl)carbonyl group, a (2-ethyl-1-hexyl)carbonyl group, a heptylcarbonyl group, a (3-ethyl-1-heptyl)carbonyl group, an octylcarbonyl group, a nonylcarbonyl group, a decylcarbonyl group, an undecylcarbonyl group, a dodecylcarbonyl group, a cyclohexylmethylcarbonyl group, a cyclopropylcarbonyl group, a cyclobutylcarbonyl group, a cyclopentylcarbonyl group, and a cyclohexylcarbonyl group; acyloxy groups such as an acetoxy group or a benzoyloxy group; alkoxycarbonyl groups such as a methoxycarbonyl group, an ethoxycarbonyl group, or a propoxycarbonyl group; Groups represented by the following formulas (GL-1) to (GL-8) (in the following formulas, ● represents a bond);

[0085] [ka]

[0086] N-Methylcarbamoyl group, N-Ethylcarbamoyl group, N-Propylcarbamoyl group, N-Isopropylcarbamoyl group, N-Butylcarbamoyl group, N-Isobutylcarbamoyl group, N-Sec-Butylcarbamoyl group, N-Tert-Butylcarbamoyl group, N-Pentylcarbamoyl group, N-(1-Ethyl-1-propyl)carbamoyl group, N-(1,1-Dimethyl-1-propyl)carbamoyl group, N-(1,2-Dimethyl-1-propyl)carbamoyl group, N-(2,2-Dimethyl-1-propyl)carbamoyl group, N-(1-Methyl-1-butyl)carbamoyl group, N-(2-Methyl-1-butyl)carbamoyl group mono-substituted carbamoyl groups such as an N-(3-methyl-1-butyl)carbamoyl group, an N-cyclopentylcarbamoyl group, an N-hexylcarbamoyl group, an N-(1,3-dimethyl-1-butyl)carbamoyl group, an N-(3,3-dimethyl-1-butyl)carbamoyl group, an N-heptylcarbamoyl group, an N-(1-methyl-1-hexyl)carbamoyl group, an N-(1,4-dimethylpentyl)carbamoyl group, an N-octylcarbamoyl group, an N-(2-ethyl-1-hexyl)carbamoyl group, an N-(1,5-dimethyl-1-hexyl)carbamoyl group, or an N-(1,1,2,2-tetramethyl-1-butyl)carbamoyl group;

[0087] di-substituted carbamoyl groups such as an N,N-dimethylcarbamoyl group, an N,N-ethylmethylcarbamoyl group, an N,N-diethylcarbamoyl group, an N,N-propylmethylcarbamoyl group, an N,N-isopropylmethylcarbamoyl group, an N,N-tert-butylmethylcarbamoyl group, an N,N-butylethylcarbamoyl group, an N,N-bis(1-methyl-1-propyl)carbamoyl group, an N,N-heptylmethylcarbamoyl group, or an N,N-bis(2-ethyl-1-hexyl)carbamoyl group;

[0088] N-Methylsulfamoyl group, N-Ethylsulfamoyl group, N-Propylsulfamoyl group, N-Isopropylsulfamoyl group, N-Butylsulfamoyl group, N-Isobutylsulfamoyl group, N-Sec-Butylsulfamoyl group, N-Tert-Butylsulfamoyl group, N-Pentylsulfamoyl group, N-(1-Ethyl-1-propyl)sulfamoyl group, N-(1,1-Dimethyl-1-propyl)sulfamoyl group, N-(1,2-Dimethyl-1-propyl)sulfamoyl group, N-(2,2-Dimethyl-1-propyl)sulfamoyl group, N-(1-Methyl-1-butyl)sulfamoyl group, N-(2-Methylbutyl)sulfamoyl group mono-substituted sulfamoyl groups such as a N-(3-methyl-1-butyl)sulfamoyl group, a N-cyclopentylsulfamoyl group, a N-hexylsulfamoyl group, a N-(1,3-dimethyl-1-butyl)sulfamoyl group, a N-(3,3-dimethyl-1-butyl)sulfamoyl group, a N-heptylsulfamoyl group, a N-(1-methyl-1-hexyl)sulfamoyl group, a N-(1,4-dimethyl-1-pentyl)sulfamoyl group, a N-octylsulfamoyl group, a N-(2-ethyl-1-hexyl)sulfamoyl group, a N-(1,5-dimethyl-1-hexyl)sulfamoyl group, or a N-(1,1,2,2-tetramethyl-1-butyl)sulfamoyl group;

[0089] di-substituted sulfamoyl groups such as an N,N-dimethylsulfamoyl group, an N,N-ethylmethylsulfamoyl group, an N,N-diethylsulfamoyl group, an N,N-propylmethylsulfamoyl group, an N,N-isopropylmethylsulfamoyl group, an N,N-tert-butylmethylsulfamoyl group, an N,N-butylethylsulfamoyl group, an N,N-bis(1-methyl-1-propyl)sulfamoyl group, an N,N-heptylmethylsulfamoyl group, or an N,N-bis(2-ethyl-1-hexyl)sulfamoyl group;

[0090] N-methylamino group, N-ethylamino group, N-propylamino group, N-isopropylamino group, N-butylamino group, N-isobutylamino group, N-sec-butylamino group, N-tert-butylamino group, N-pentylamino group, N-(1-ethyl-1-propyl)amino group, N-(1,1-dimethyl-1-propyl)amino group, N-(1,2-dimethyl-1-propyl)amino group, N-(2,2-dimethyl-1-propyl)amino group, N-(1-methyl-1-butyl)amino group, N-(2-methyl-1-butyl)amino group, N- N-alkylamino groups such as a (3-methyl-1-butyl)amino group, an N-cyclopentylamino group, an N-hexylamino group, an N-(1,3-dimethyl-1-butyl)amino group, an N-(3,3-dimethyl-1-butyl)amino group, an N-heptylamino group, an N-(1-methyl-1-hexyl)amino group, an N-(1,4-dimethyl-1-pentyl)amino group, an N-octylamino group, an N-(2-ethyl-1-hexyl)amino group, an N-(1,5-dimethyl-1-hexyl)amino group, or an N-(1,1,2,2-tetramethyl-1-butyl)amino group;

[0091] N,N-dialkylamino groups such as an N,N-dimethylamino group, an N,N-ethylmethylamino group, an N,N-diethylamino group, an N,N-propylmethylamino group, an N,N-isopropylmethylamino group, an N,N-tert-butylmethylamino group, an N,N-butylethylamino group, an N,N-bis(1-methyl-1-propyl)amino group, an N,N-heptylmethylamino group, or an N,N-bis(2-ethyl-1-hexyl)amino group;

[0092] N-Methylaminomethyl group, N-Ethylaminomethyl group, N-Propylaminomethyl group, N-Isopropylaminomethyl group, N-Butylaminomethyl group, N-Isobutylaminomethyl group, N-Sec-Butylaminomethyl group, N-Tert-Butylaminomethyl group, N-Pentylaminomethyl group, N-(1-Ethyl-1-propyl)aminomethyl group, N-(1,1-Dimethyl-1-propyl)aminomethyl group, N-(1,2-Dimethyl-1-propyl)aminomethyl group, N-(2,2-Dimethyl-1-propyl)aminomethyl group, N-(1-Methyl-1-butyl)aminomethyl group, N-(2-Methyl-1-butyl)aminomethyl group , N-alkylaminomethyl groups such as an N-(3-methyl-1-butyl)aminomethyl group, an N-cyclopentylaminomethyl group, an N-hexylaminomethyl group, an N-(1,3-dimethyl-1-butyl)aminomethyl group, an N-(3,3-dimethyl-1-butyl)aminomethyl group, an N-heptylaminomethyl group, an N-(1-methyl-1-hexyl)aminomethyl group, an N-(1,4-dimethyl-1-pentyl)aminomethyl group, an N-octylaminomethyl group, an N-(2-ethyl-1-hexyl)aminomethyl group, an N-(1,5-dimethyl-1-hexyl)aminomethyl group, or an N-(1,1,2,2-tetramethyl-1-butyl)aminomethyl group;

[0093] N,N-dialkylaminomethyl groups such as an N,N-dimethylaminomethyl group, an N,N-ethylmethylaminomethyl group, an N,N-diethylaminomethyl group, an N,N-propylmethylaminomethyl group, an N,N-isopropylmethylaminomethyl group, an N,N-tert-butylmethylaminomethyl group, an N,N-butylethylaminomethyl group, an N,N-bis(1-methyl-1-propyl)aminomethyl group, an N,N-heptylmethylaminomethyl group, or an N,N-di(2-ethyl-1-hexyl)aminomethyl group;

[0094] trifluoromethyl group, perfluoroethyl group, perfluoropropyl group, perfluoroisopropyl group, perfluoroisopropenyl group, perfluoro(1-propenyl) group, perfluoro(2-propenyl) group, perfluorobutyl group, perfluoroisobutyl group, perfluoro(sec-butyl) group, perfluoro(tert-butyl) group, perfluoro(2-butenyl) group, perfluoro(1,3-butadienyl) group, perfluoropentyl group, perfluoro(isopentyl) group, perfluoro(3-pentyl) group, perfluoroneopentyl group, aliphatic hydrocarbon groups having a fluorine atom, such as a perfluoro(tert-pentyl) group, a perfluoro(1-methylpentyl) group, a perfluoro(2-methyl-1-pentyl) group, a perfluoro(2-pentenyl) group, a perfluorohexyl group, a perfluoroisohexyl group, a perfluoro(5-methyl-1-hexyl) group, a perfluoro(2-ethyl-1-hexyl) group, a perfluoroheptyl group, a perfluorooctyl group, a perfluorononyl group, a perfluorodecyl group, a perfluoroundecyl group, a perfluorododecyl group, or a perfluorooctadecyl group;

[0095] perfluorocyclopropyl group, perfluorocyclobutyl group, perfluorocyclopentyl group, perfluorocyclohexyl group, perfluorocyclohexenyl group, perfluorocycloheptyl group, perfluoro(1-methylcyclohexyl) group, perfluoro(2-methylcyclohexyl) group, perfluoro(3-methylcyclohexyl) group, perfluoro(4-methylcyclohexyl) group, perfluoro(1,2-dimethylcyclohexyl) group, perfluoro(1,3-dimethylcyclohexyl) group, perfluoro(1,4-dimethylcyclohexyl) group, perfluoro(2,3-dimethylcyclohexyl) group, perfluoro(2,4-dimethyl alicyclic hydrocarbon groups having a fluorine atom, such as a perfluoro(2,5-dimethylcyclohexyl) group, a perfluoro(2,6-dimethylcyclohexyl) group, a perfluoro(3,4-dimethylcyclohexyl) group, a perfluoro(3,5-dimethylcyclohexyl) group, a perfluoro(2,2-dimethylcyclohexyl) group, a perfluoro(3,3-dimethylcyclohexyl) group, a perfluoro(4,4-dimethylcyclohexyl) group, a perfluoro(2,4,6-trimethylcyclohexyl) group, a perfluoro(2,2,6,6-tetramethylcyclohexyl) group, or a perfluoro(3,3,5,5-tetramethylcyclohexyl) group;

[0096] aromatic hydrocarbon groups having a fluorine atom, such as a perfluorophenyl group, a perfluoro(o-tolyl) group, a perfluoro(m-tolyl) group, a perfluoro(p-tolyl) group, a perfluoroxylyl group, a perfluoromesityl group, a perfluoro(o-cumenyl) group, a perfluoro(m-cumenyl) group, a perfluoro(p-cumenyl) group, a perfluorobenzyl group, a perfluorophenethyl group, a perfluorobiphenylyl group, a perfluoro(1-naphthyl) group, a perfluoro(2-naphthyl) group, a 1-trifluoromethylphenyl group, a 2-trifluoromethylphenyl group, a 3-trifluoromethylphenyl group, or a 4-trifluoromethylphenyl group;

[0097] perfluoromethoxy group, perfluoroethoxy group, perfluoropropoxy group, perfluoro(isopropoxy) group, perfluorobutoxy group, perfluoro(isobutoxy) group, perfluoro(sec-butoxy) group, perfluoro(tert-butoxy) group, perfluoropentyloxy group, perfluorophenoxy group, perfluorobenzyloxy group, 2,2,2-trifluoroethoxy group, (perfluoroethyl)methoxy group, (perfluoropropyl)methoxy group, (perfluoro(isopropyl))methoxy group, (perfluoro(isopropenyl))methoxy group, (perfluoro(1-propenyl))methoxy group, (perfluoro(2-propenyl))methoxy group, (perfluorobutyl)methoxy group, (perfluoro(isobutyl))methoxy group, (perfluoro(sec-butyl))methoxy group, (perfluoro(tert-butyl))methoxy group, (perfluoro(2-butenyl))methoxy group, (perfluoro(1,3-butadienyl) )methoxy group, (perfluoropentyl)methoxy group, (perfluoro(isopentyl))methoxy group, (perfluoro(3-pentyl))methoxy group, (perfluoro(neopentyl))methoxy group, (perfluoro(tert-pentyl))methoxy group, (perfluoro(1-methyl-1-pentyl))methoxy group, (perfluoro(2-methylpentyl))methoxy group, (perfluoro(2-pentenyl))methoxy group, (perfluorohexyl)methoxy group, (perfluoro(isohexyl))methoxy group, (perfluoro(5-methyl-1-hexyl))methoxy group, (perfluoro(2-ethyl-1-hexyl))methoxy group, (perfluoroheptyl)methoxy group, (perfluorooctyl)methoxy group, (perfluorononyl)methoxy group, (perfluorodecyl)methoxy group, (perfluoroundecyl)methoxy group, (perfluorododecyl)methoxy group, (perfluorooctadecyl)methoxy group, and other substituted oxy groups having a fluorine atom;

[0098] Examples of such groups include a 2,3-bis(trifluoromethyl)phenylmethyl group, a 2,4-bis(trifluoromethyl)phenylmethyl group, a 2,5-bis(trifluoromethyl)phenylmethyl group, a 2,6-bis(trifluoromethyl)phenylmethyl group, a 3,4-bis(trifluoromethyl)phenylmethyl group, and a 3,5-bis(trifluoromethyl)phenylmethyl group.

[0099] R 7 ~R 11 and R 13 is preferably a hydrogen atom. R 12 is preferably a hydrogen atom, -SO3M or -CO2M, more preferably a hydrogen atom or -SO3M, and particularly preferably a hydrogen atom.

[0100] In formula (A1-4), Z represents a group represented by the following formula (Z1) (in the following formula, * represents a bond).

[0101] [ka]

[0102] In formula (Z1), R 1 represents an alkyl group having 1 to 20 carbon atoms, and -CH2- constituting the alkyl group may be replaced with an oxygen atom. Examples of such an alkyl group include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a 2-ethyl-1-butyl group, a pentyl group, an isopentyl group, a 3-pentyl group, a neopentyl group, a tert-pentyl group, a 1-methyl-1-pentyl group, a 2-methyl-1-pentyl group, a 3-ethyl-1-pentyl group, a hexyl group, an isohexyl group, a 5-methyl-1-hexyl group, a 2-ethyl-1-hexyl group, a heptyl group, a 3-ethyl-1-heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, and an octadecyl group, and an alkyl group having 1 to 16 carbon atoms is preferred.

[0103] Examples of the groups in which --CH2-- constituting these alkyl groups is replaced with an oxygen atom include the groups represented by the above formulae (GL-1) to (GL-8).

[0104] When L is a divalent hydrocarbon group having 1 to 20 carbon atoms or a sulfonyl group, and Z is a group represented by formula (Z1), from the viewpoint of the solubility of compound (A1-4) in a solvent, R 1 is preferably an alkyl group having 1 to 16 carbon atoms or a group represented by any one of formulas (GL-1) to (GL-8), more preferably an alkyl group having 4 to 12 carbon atoms or a group represented by any one of formulas (GL-1) to (GL-8), even more preferably an alkyl group having 6 to 10 carbon atoms (e.g., 2-ethyl-1-hexyl group, 1-octyl group, etc.) or a group represented by any one of formulas (GL-3) to (GL-8), and particularly preferably a 1-octyl group.

[0105] In formula (Z1), R 2 ~R 6 each independently represents a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carbamoyl group, a sulfamoyl group, -SO3M, -CO2M, a hydroxyl group, a formyl group, an amino group, or a monovalent hydrocarbon group having 1 to 20 carbon atoms, and -CH2- constituting the hydrocarbon group is an oxygen atom, a sulfur atom, -N(R 30 The hydrogen atoms contained in the hydrocarbon group may be replaced by halogen atoms, cyano groups, nitro groups, carbamoyl groups, sulfamoyl groups, -SO3M, -CO2M, hydroxy groups, formyl groups or amino groups. 30 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms; R 30 When a plurality of M's are present, they may be the same or different. M represents a hydrogen atom or an alkali metal atom. When a plurality of M's are present, they may be the same or different. R 2 ~R 6 As the R 7 ~R 13The same can be mentioned. R 30 Also, R 14 The same can be mentioned.

[0106] When L is a divalent hydrocarbon group having 1 to 20 carbon atoms or a sulfonyl group, and Z is a group represented by formula (Z1), from the viewpoint of the solubility of compound (A1-4) in a solvent, R 2 is preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 10 carbon atoms, more preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, further preferably a methyl group, an ethyl group or a 2-propyl group, and particularly preferably a methyl group. 2 A color filter formed from a colored curable resin composition containing a colorant that contains the compound (A1-4) in which R is one of these groups tends to have high brightness.

[0107] When L is a divalent hydrocarbon group having 1 to 20 carbon atoms or a sulfonyl group, and Z is a group represented by formula (Z1), from the viewpoint of the solubility of compound (A1-4) in a solvent, R 4 is preferably a hydrogen atom, -SO3M, -CO2M, or an alkyl group having 1 to 8 carbon atoms (e.g., a methyl group, an ethyl group, a 1-propyl group, a 2-propyl group, a 1-butyl group, a tert-butyl group, a 1-hexyl group, a 2-ethyl-1-hexyl group, a 1-octyl group, etc.), more preferably a hydrogen atom, -SO3M, -CO2M, or an alkyl group having 1 to 4 carbon atoms, and even more preferably a methyl group.

[0108] When L is a divalent hydrocarbon group having 1 to 20 carbon atoms or a sulfonyl group, and Z is a group represented by formula (Z1), R 6 is preferably a hydrogen atom, an aliphatic hydrocarbon group having 1 to 10 carbon atoms, -SO3M or -CO2M, more preferably a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or -SO3M, and particularly preferably a hydrogen atom.

[0109] When L is a divalent hydrocarbon group having 1 to 20 carbon atoms or a sulfonyl group, and Z is a group represented by formula (Z1), R3 and R 5 is preferably a hydrogen atom.

[0110] From the viewpoint of light fastness, the coumarin dye is preferably one or both of a compound represented by formula (A1-3) and a compound represented by formula (A1-4), and from the viewpoint of further improved light fastness, a compound represented by formula (A1-4) is more preferable.

[0111] The content of the coumarin dye, relative to the total amount of the colorant (A), is, for example, 10 mass% or more, preferably 20 mass% or more, more preferably 30 mass% or more, and for example, 95 mass% or less, preferably 90 mass% or less, more preferably 80 mass% or less.

[0112] The content of the coumarin dye, relative to the solid content of the colored curable resin composition, is, for example, 2 mass% or more, preferably 4 mass% or more, and more preferably 6 mass% or more, and for example, 60 mass% or less, preferably 50 mass% or less, and more preferably 40 mass% or less.

[0113] The content ratio of squarylium dye and coumarin dye to anthraquinone dye is preferably 0.5 or more, more preferably 1 or more, even more preferably 1.5 or more, even more preferably 1.7 or more, and is preferably 10 or less, more preferably 7 or less, even more preferably 5 or less.

[0114] The colored curable resin composition of the present invention may contain a colorant (hereinafter, sometimes referred to as colorant (A2)) other than an anthraquinone dye, a squarylium dye, and a coumarin dye having a carboxy group as the colorant (A). The colorant (A2) may contain one or more types of colorants.

[0115] The colorant (A2) may be a dye or a pigment. Examples of the dye include known dyes described in the Color Index (published by The Society of Dyers and Colourists) and Dyeing Notes (Shikisensha). In addition, according to the chemical structure, examples of the dye include azo dyes, anthraquinone dyes (excluding the compound represented by formula (A1)), triphenylmethane dyes, cyanine dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes (excluding the compound represented by formula (A1-2)), acridine dyes, styryl dyes, coumarin dyes (excluding the compound represented by formula (A1-3) and the compound represented by formula (A1-4)), quinoline dyes, nitro dyes, and phthalocyanine dyes. Among these, organic solvent-soluble dyes are preferred. These dyes may be used in combination of two or more kinds.

[0116] Specifically, dyes with the following Color Index (CI) numbers are included: CI Solvent Yellow 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162; CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; CI Reactive Yellow 2, 76, 116; CI Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141; CI Disperse Yellow 51, 54, 76; CI Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 99; CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173; CI Reactive Orange 16; CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI Solvent Red 24, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; CI Acid Red 73, 80, 91, 92, 97, 138, 151, 211, 274, 289; CI Acid Violet 34, 102; CI Disperse Violet 26, 27; CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; CI Solvent Blue 14, 18, 35, 36, 45, 58, 59, 59:1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; CI Acid Blue 25, 27, 40, 45, 78, 80, 112; CI Direct Blue 40; CI Disperse Blue 1, 14, 56, 60; CI Solvent Green 1, 3, 5, 28, 29, 32, 33; CI Acid Green 3, 5, 9, 25, 27, 28, 41; CI Basic Green 1; CI Bat Green 1st Class.

[0117] As the pigment, known pigments can be used, for example, pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists). Two or more kinds of pigments may be used in combination. Specifically, yellow pigments such as 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; Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73; Red pigments such as CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 192, 202, 208, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273, brominated diketopyrrolopyrroles; Blue pigments such as CI Pigment Blue 15, 15:3, 15:4, 15:6, 60; Violet pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, 38; Examples of green pigments include CI Pigment Green 7, 36, 58, and 59.

[0118] The colorant (A2) may be subjected to, as necessary, a rosin treatment, a surface treatment using a colorant derivative having an acidic or basic group introduced therein, a grafting treatment to the surface of the pigment using a polymer compound, a microparticulation treatment using a sulfuric acid microparticulation method, a washing treatment using an organic solvent or water to remove impurities, a removal treatment of ionic impurities using an ion exchange method, etc. The particle size of the pigment is preferably approximately uniform. The colorant (A2) is uniformly dispersed in the dispersion by adding a dispersant and carrying out a dispersion treatment.

[0119] Examples of the dispersant include surfactants, which may be cationic, anionic, nonionic, or amphoteric. Specific examples include polyester, polyamine, and acrylic surfactants. As another dispersant, a resin (B) described later may be used. These dispersants may be used alone or in combination of two or more. Examples of the dispersant, in terms of trade name, include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWRENE (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK), and BYK (registered trademark) (manufactured by BYK).

[0120] When a dispersant is used, the amount of the dispersant used is preferably 100 parts by mass or less, more preferably 5 parts by mass or more and 50 parts by mass or less, relative to 100 parts by mass of the colorant (A2). When the amount of the dispersant used is within the above range, a liquid containing the colorant (A2) in a more uniformly dispersed state tends to be obtained.

[0121] In the colored curable resin composition, when the colorant (A2) is contained, the content thereof is usually from 0.1 mass% to 50 mass% inclusive, preferably from 1 mass% to 40 mass% inclusive, and more preferably from 1 mass% to 30 mass% inclusive, in the total amount of solids.

[0122] <Resin (B)> Resin (B) is not particularly limited, but is preferably an alkali-soluble resin, and more preferably a resin having a structural unit derived from at least one type (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides. Resin (B) further preferably has at least one structural unit selected from the group consisting of a structural unit derived from a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond, a structural unit derived from a monomer (c) (however, different from (a) and (b)) (hereinafter sometimes referred to as "(c)") copolymerizable with (a), and a structural unit having an ethylenically unsaturated bond in a side chain.

[0123] Specific examples of (a) include acrylic acid, methacrylic acid, maleic anhydride, itaconic anhydride, and 3,4,5,6-tetrahydrophthalic anhydride; Examples of the monomer include mono[2-(meth)acryloyloxyethyl] succinate, and preferred are acrylic acid, methacrylic acid, and maleic anhydride. In this specification, the term "(meth)acrylic acid" refers to 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.

[0124] (b) is preferably a monomer having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and a (meth)acryloyloxy group. Examples of (b) include glycidyl (meth)acrylate, vinylbenzyl glycidyl ether, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl(meth)acrylate, 3-ethyl-3-(meth)acryloyloxymethyloxetane, tetrahydrofurfuryl(meth)acrylate, etc., and preferably, glycidyl(meth)acrylate, 3,4-epoxytricyclo[5.2.1.0 2,6]decyl (meth)acrylate, 3-ethyl-3-(meth)acryloyloxymethyloxetane.

[0125] Examples of (c) include methyl (meth)acrylate, butyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]Decan-8-yl (meth)acrylate benzyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, styrene, vinyltoluene, etc., are mentioned, and preferably styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, 2-hydroxyethyl (meth)acrylate, etc. are preferred.

[0126] The resin having a structural unit having an ethylenically unsaturated bond in the side chain can be produced by adding (b) to a copolymer of (a) and (c), or by adding (a) to a copolymer of (b) and (c). The resin may be a resin obtained by adding (a) to a copolymer of (b) and (c) and then reacting with a carboxylic acid anhydride.

[0127] The polystyrene-equivalent weight average molecular weight of resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 5,000 to 30,000. The dispersity of the resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1.1-6, and more preferably 1.2-4.

[0128] The acid value of the resin (B) is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150 mg-KOH / g, and further preferably 70 to 135 mg-KOH / g, calculated as solid content. The acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be determined, for example, by titration with an aqueous potassium hydroxide solution.

[0129] The content of the resin (B) is preferably from 10 to 70% by mass, more preferably from 15 to 65% by mass, and further preferably from 20 to 60% by mass, based on the total solid content.

[0130] <Polymerizable compound (C)> The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and are preferably (meth)acrylic acid ester compounds.

[0131] Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa(meth)acrylate.

[0132] The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, and more preferably 250 or more and 1,500 or less.

[0133] The content of the polymerizable compound (C) is preferably from 10 to 70% by mass, more preferably from 15 to 65% by mass, and further preferably from 20 to 60% by mass, based on the total solid content.

[0134] <Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that generates active radicals, acids, etc. by the action of light or heat and can initiate polymerization, and known polymerization initiators can be used. Examples of polymerization initiators that generate active radicals include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, 2-methyl-2-morpholino-1-(4-methylsulfonylphenyl)-2-methylsulfonylphenyl, and the like. Examples of such amines include 2-dimethylamino-1-(4-morpholinophenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 1-hydroxycyclohexyl phenyl ketone 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, and 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole.

[0135] The polymerization initiator is preferably a polymerization initiator containing at least one selected from the group consisting of a triazine compound, an acylphosphine oxide compound, an alkylphenone compound, an O-acyloxime compound, and a biimidazole compound, and more preferably a polymerization initiator containing an O-acyloxime compound.

[0136] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, the sensitivity is increased and the exposure time tends to be shortened, thereby improving the productivity of the color filter.

[0137] The content of the O-acyloxime compound is preferably 50% by mass or more, more preferably 80% by mass or more, even more preferably 90% by mass or more, and particularly preferably 95% by mass or more, based on the total amount of the polymerization initiator (D). When the content of the O-acyloxime compound is within the above range, there is a tendency that the sensitivity and developability when forming a colored pattern, and a color filter with high brightness even when the colorant content is high, can be produced.

[0138] The colored curable resin composition of the present invention may contain a polymerization initiator aid.

[0139] <Polymerization initiator aid (D1)> The polymerization initiation aid (D1) is a compound used to promote the polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator, or a sensitizer. When the polymerization initiation aid (D1) is contained, it is usually used in combination with the polymerization initiator (D). Examples of the polymerization initiator aid (D1) include 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, 9,10-dimethoxyanthracene, 2,4-diethylthioxanthone, N-phenylglycine, and the like.

[0140] When these polymerization initiation aids (D1) are used, the content thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with higher sensitivity, and the productivity of the color filter tends to improve.

[0141] The colored curable resin composition of the present invention preferably contains a solvent.

[0142] <Solvent (E)> The solvent (E) is not particularly limited, and a solvent commonly used in the field can be used. For example, ester solvent (solvent containing -COO- in the molecule and not containing -O-), ether solvent (solvent containing -O- in the molecule and not containing -COO-), ether ester solvent (solvent containing -COO- and -O- in the molecule), ketone solvent (solvent containing -CO- in the molecule and not containing -COO-), alcohol solvent (solvent containing OH in the molecule and not containing -O-, -CO- and -COO-), aromatic hydrocarbon solvent, amide solvent, dimethyl sulfoxide, etc. can be mentioned.

[0143] Examples of the solvent include ester solvents (solvents that contain -COO- and do not contain -O- in the molecule) such as ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, methyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone; ether solvents (solvents that contain -O- and do not contain -COO- in the molecule) such as ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, 3-methoxy-1-butanol, diethylene glycol dimethyl ether, and diethylene glycol methyl ethyl ether; Ether ester solvents (solvents containing -COO- and -O- in the molecule) such as methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, 3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, and diethylene glycol monoethyl ether acetate; Ketone solvents such as 4-hydroxy-4-methyl-2-pentanone, heptanone, 4-methyl-2-pentanone, and cyclohexanone (solvents that contain -CO- but not -COO- in the molecule); Alcohol solvents such as butanol, cyclohexanol, and propylene glycol (solvents that contain OH in the molecule but do not contain -O-, -CO-, or -COO-); Examples of the solvent include aromatic hydrocarbon solvents such as toluene and xylene, and amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0144] More preferred solvents are propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, cyclohexanone, N-methylpyrrolidone and ethyl 3-ethoxypropionate.

[0145] The solvent is preferably a mixed solvent containing propylene glycol monomethyl ether acetate.The solvent to be combined with propylene glycol monomethyl ether acetate is preferably ethyl lactate, propylene glycol monomethyl ether, 3-ethoxypropionate ethyl, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, dipropylene glycol methyl ether acetate, 3-methoxybutyl acetate, 3-methoxy-1-butanol, N-methylpyrrolidone and 4-hydroxy-4-methyl-2-pentanone, more preferably propylene glycol monomethyl ether, dipropylene glycol methyl ether acetate, ethyl lactate, 3-methoxybutyl acetate, 3-methoxy-1-butanol, N-methylpyrrolidone and 3-ethoxypropionate ethyl, more preferably ethyl lactate, 4-hydroxy-4-methyl-2-pentanone, N-methylpyrrolidone and propylene glycol monomethyl ether.

[0146] The content of the solvent to be combined with propylene glycol monomethyl ether acetate is preferably 1% by mass or more and 90% by mass or less, more preferably 3% by mass or more and 85% by mass or less, and even more preferably 5% by mass or more and 80% by mass or less, based on the total amount of the solvent.

[0147] When the colored curable resin composition contains a solvent (E), the content of the solvent (E) is preferably 20 to 90% by mass, more preferably 25 to 85% by mass, based on the total amount of the colored curable resin composition of the present invention. In other words, the total amount of solids in the colored curable resin composition is preferably 10 to 80% by mass, more preferably 15 to 75% by mass. When the content of the solvent (E) is within the above range, the flatness during coating is good, and the color density is not insufficient when a color filter is formed, so that the display characteristics tend to be good.

[0148] <Other ingredients> The colored curable resin composition of the present invention may contain additives known in the technical field, such as a leveling agent, a filler, another polymer compound, an adhesion promoter, an antioxidant, a light stabilizer, and a chain transfer agent, as necessary.

[0149] <Method for producing colored curable resin composition> The colored curable resin composition of the present invention can be prepared by mixing the colorant (A), the resin (B), the polymerizable compound (C), the polymerization initiator (D), and, if necessary, the solvent (E) and other components.

[0150] <Manufacturing method of color filters> Methods for producing a colored pattern from the colored curable resin composition of the present invention include photolithography, inkjet, and printing. Among them, photolithography is preferred. In the photolithography, a colored coating film, which is a cured product of the colored curable resin composition layer, can be formed by not using a photomask during exposure and / or not developing. The colored pattern or colored coating film thus formed is the color filter of the present invention.

[0151] The colored curable resin composition can be used to prepare a color filter having excellent light resistance. The color filter is useful as a color filter for use in display devices (e.g., liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging devices. EXAMPLES

[0152] The present invention will now be described in more detail with reference to examples. In the examples, % and parts indicating the content or amount used are by weight unless otherwise specified.

[0153] In the following examples, the structures of the compounds were identified by mass spectrometry (LC; Agilent 1200 model, MASS; Agilent LC / MSD model) or NMR (JNM-EX-270; JEOL Ltd.).

[0154] [Synthesis Example 1] [ka]

[0155] In a flask equipped with a cooling tube and a stirrer, 66.9 parts of chlorosulfuric acid was added and cooled to 10°C or less, and 3.6 parts of CISolvent Blue 104 (compound (X-1)) was slowly added while stirring. After that, the reaction liquid was allowed to warm up to room temperature and stirred at the same temperature for 6 hours. The resulting reaction liquid was dropped into 108 parts of ice water to form a suspension, and the precipitated crystals were filtered off, washed thoroughly with ion-exchanged water, and dried under reduced pressure at 60°C overnight to obtain 4.9 parts of a crude compound represented by formula (A-1-IM1). This was purified by silica gel column chromatography (solvent: chloroform) to obtain 3.4 parts of a compound represented by formula (A-1-IM1).

[0156] [ka]

[0157] In a flask equipped with a cooling tube and a stirrer, 4.6 parts of methyl 3-amino-4-methylbenzoate and 16.5 parts of chloroform were added and cooled to 10°C or less, and a solution of 2.4 parts of the compound represented by formula (A-1-IM1) dissolved in 16.5 parts of chloroform and 2.2 parts of pyridine were successively added dropwise under stirring. Thereafter, the reaction solution was allowed to warm up to room temperature and stirred at the same temperature for 5.5 hours. 150 parts of chloroform and 50 parts of 2N hydrochloric acid were added to the obtained reaction solution to separate the liquid, and the organic layer was washed twice with 50 parts of 2N hydrochloric acid. The obtained organic layer was dried with excess sodium sulfate, and the solution obtained after filtration was evaporated to obtain 3.4 parts of a crude product of the compound represented by formula (A-1-IM2). This was purified by silica gel column chromatography (solvent: chloroform) to obtain 2.8 parts of the compound represented by formula (A-1-IM2).

[0158] [ka]

[0159] Identification of the compound represented by formula (A-1-IM2) (Mass spectrometry) Ionization mode = ESI + : m / z= [M+H] + 929.2 Exact Mass: 928.3

[0160] In a flask equipped with a condenser and a stirrer, 2.5 parts of the compound represented by formula (A-1-IM2), 35 parts of N-methylpyrrolidone, and 17 parts of an 8% aqueous sodium hydroxide solution were added and stirred for 5 hours at 50° C. The resulting reaction liquid was added to 175 parts of 2N hydrochloric acid to form a suspension, and the precipitated crystals were filtered off, thoroughly washed with ion-exchanged water, and dried overnight under reduced pressure at 60° C. to obtain 2.1 parts of the compound represented by formula (A-1) (hereinafter sometimes referred to as “dye (A-1)”).

[0161] [ka]

[0162] Identification of the compound represented by formula (A-1) (Mass spectrometry) Ionization mode = ESI + : m / z= [M+H] + 901.2 Exact Mass: 900.3

[0163] [Synthesis Example 2] 10.0 parts of 2,4-dimethylaniline (Tokyo Chemical Industry Co., Ltd.), 17.0 parts of 2-ethylhexane bromide (Tokyo Chemical Industry Co., Ltd.), and 44.0 parts of tetrabutylammonium bromide (Fujifilm Wako Pure Chemical Industries, Ltd.) were mixed. The resulting mixture was stirred at 90°C for 8 hours. After the reaction was completed, 50 parts of 10% sodium bicarbonate water was added, and then 100 parts of ethyl acetate was added and the aqueous layer was discarded. The operation of washing with water and 10% hydrochloric acid was repeated twice, and the solvent was distilled off. The obtained oil was dried under reduced pressure at 60°C for 24 hours to obtain 9.3 parts of the compound represented by formula (d-1).

[0164] [ka]

[0165] The compound represented by formula (d-1) 1 H-NMR (270MHz, δ value (ppm, TMS standard), DMSO-d6) 0.85 (m, 6H), 1.23-1.42 (br, 8H), 1.59 (br, 1H), 2 .04(s,3H), 2.12(s,3H), 2.91(d,2H), 4.37(br,1H), 6.38(d,1H), 6.75(s,1H), 6.77(d,1H)

[0166] 3.0 parts of the compound represented by formula (d-1) obtained above, 2.2 parts of 3-bromophenol (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.015 parts of palladium acetate, 3.2 parts of sodium tert-butoxide (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.055 parts of tri-tert-butylphosphine (manufactured by Tokyo Chemical Industry Co., Ltd.) and 25.6 parts of toluene were mixed and stirred at 100 ° C. for 15 hours. 30 parts of ethyl acetate and 100 parts of water were added to the obtained mixture and the aqueous layer was discarded. After repeating the operation of washing with water twice, the solvent was distilled off. The residue was purified by silica gel chromatography (chloroform / hexane = 1 / 1), and the obtained oil was dried under reduced pressure at 60 ° C. for 24 hours to obtain 1.9 parts of the compound represented by formula (d-2).

[0167] [ka]

[0168] The compound represented by formula (d-2) 1 H-NMR (270MHz, δ value (ppm, TMS standard), DMSO-d6) 0.85 (m, 6H), 1.23-1.42 (br, 8H), 1.55 (br, 1H), 1.94 (s, 3) H), 2.27(s,3H), 2.90(d,2H), 6.37(d,1H), 6.75(s,1H), 6.76(d,1H), 6.92-7.14(m,4H), 8.93(s,1H)

[0169] 4.4 parts of the compound represented by formula (d-2) obtained above, 0.8 parts of 3,4-dihydroxy-3-cyclobutene-1,2-dione (manufactured by Tokyo Chemical Industry Co., Ltd.), 90 parts of 1-butanol, and 60 parts of toluene were mixed. The obtained mixture was stirred at 125°C for 3 hours while removing the water generated using a Dean-Stark tube. After the reaction was completed, the solvent was distilled off, 15 parts of acetic acid was added, and then dropped into 100 parts of 18% saline, and the precipitated solid was filtered off. The filtered solid was washed with hexane. The obtained solid was dried under reduced pressure at 60°C for 24 hours to obtain 4.9 parts of a compound represented by formula (AII-8) (hereinafter sometimes referred to as "dye (AII-8)").

[0170] [ka]

[0171] The compound represented by formula (AII-8) 1 H-NMR (270MHz, δ value (ppm, TMS standard), DMSO-d6) 0.87 (m, 12H), 1.21-1.57 (m, 16H), 1.72 (br, 2H), 2.05 (s, 6H), 2.36 (s, 6H), 3.37(br,2H), 3.78(br,2H), 6.00(br,4H), 6.97-7.12(m,6H), 7.77-7.95(m,2H), 11.35(s,1H), 12.06(s,1H)

[0172] [Synthesis Example 3] The same procedure as in Synthesis Example 2 was repeated, except that in Synthesis Example 2, the compound represented by formula (d-1) was replaced by the compound represented by formula (d-3) and the compound represented by formula (d-2) was replaced by the compound represented by formula (d-4), to obtain a compound represented by the following formula (AII-X).

[0173] [ka]

[0174] [ka]

[0175] [ka]

[0176] [Synthesis Example 4] Based on Examples 1 and 2 of WO 2014 / 208767, a compound represented by the following formula (AII-Y) was prepared.

[0177] [ka]

[0178] [Synthesis Example 5] 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, and 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were added and heated to 85°C with stirring. Next, 38 parts of acrylic acid and 3,4-epoxytricyclo[5.2.1.0 2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 A mixture of 25 parts of a mixture of decan-9-yl acrylate (content ratio 1:1 by molar ratio), 137 parts of N-cyclohexylmaleimide, 50 parts of 2-hydroxyethyl methacrylate, and 338 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a solution of 5 parts of 2,2-azobisisobutyronitrile dissolved in 88 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the dropwise addition was completed, the mixture was kept at 85°C for 4 hours and then cooled to room temperature to obtain a copolymer (resin B-1) solution with a viscosity of 23 mPas measured with a B-type viscometer (23°C) and a solid content of 25.6%. The weight average molecular weight Mw of the resulting copolymer was 8.0 x 10 3 The resin B-1 had a molecular weight of 1,200, a polydispersity of 2.1, and an acid value calculated as solid content of 109 mg-KOH / g.

[0179] [ka]

[0180] The weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by GPC under the following conditions. Equipment: K2479 (Shimadzu Corporation) Column: SHIMADZU Shim-pack GPC-80M Column temperature: 40°C Solvent: THF (tetrahydrofuran) Test solution concentration: 25mg / mL (solvent: THF) Flow rate; 1.0mL / min Detector: RI Calibration standard materials: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation) The ratio of the weight average molecular weight and the number average molecular weight calculated in terms of polystyrene obtained above was defined as the dispersity (Mw / Mn).

[0181] Example 1 <Preparation of Colored Curable Resin Composition> (A) Colorant: Dye (AII-8) 10 parts (A) Coloring agent: Dye (A-1) 5 parts (B) Resin: Resin (B-1) (solid content equivalent) 50 parts (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 7 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: 596 parts of propylene glycol monomethyl ether acetate (E) Solvent: N-methylpyrrolidone 95 parts The above components were mixed to obtain a colored curable resin composition.

[0182] Comparative Example 1 <Preparation of Colored Curable Resin Composition> (A) Colorant: Dye (AII-8) 9 parts (B) Resin: Resin (B-1) (solid content equivalent) 50 parts (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 7 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: 659 parts of propylene glycol monomethyl ether acetate The above components were mixed to obtain a colored curable resin composition.

[0183] Example 2 <Preparation of Colored Curable Resin Composition> (A) Colorant: CI Disperse Yellow 82 (coumarin dye) 10 parts (A) Coloring agent: Dye (A-1) 5 parts (B) Resin: Resin (B-1) (solid content equivalent) 50 parts (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 7 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: propylene glycol monomethyl ether acetate 145 parts (E) Solvent: N-methylpyrrolidone 546 parts The above components were mixed to obtain a colored curable resin composition.

[0184] Comparative Example 2 <Preparation of Colored Curable Resin Composition> (A) Colorant: CI Disperse Yellow 82 9 parts (B) Resin: Resin (B-1) (solid content equivalent) 50 parts (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 7 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: propylene glycol monomethyl ether acetate 145 parts (E) Solvent: N-methylpyrrolidone 515 parts The above components were mixed to obtain a colored curable resin composition.

[0185] Example 3 <Preparation of Colored Curable Resin Composition> (A) Colorant: Dye (AII-8) 9.5 parts (A) Colorant: Dye (A-1) 1.6 parts (B) Resin: Resin (B-1) (solid content equivalent) 50 parts (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 7 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: 639 parts of propylene glycol monomethyl ether acetate (E) Solvent: N-methylpyrrolidone 30 parts The above components were mixed to obtain a colored curable resin composition.

[0186] Example 4 <Preparation of Colored Curable Resin Composition> (A) Colorant: Dye (AII-8) 9.4 parts (A) Colorant: Dye (A-1) 1 part (B) Resin: Resin (B-1) (solid content equivalent) 50 parts (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 7 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: 646 parts of propylene glycol monomethyl ether acetate (E) Solvent: N-methylpyrrolidone 20 parts The above components were mixed to obtain a colored curable resin composition.

[0187] Example 5 <Preparation of Colored Curable Resin Composition> (A) Colorant: CI Disperse Yellow 82 9.5 parts (A) Colorant: Dye (A-1) 1.6 parts (B) Resin: Resin (B-1) (solid content equivalent) 50 parts (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 7 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: propylene glycol monomethyl ether acetate 145 parts (E) Solvent: N-methylpyrrolidone 525 parts The above components were mixed to obtain a colored curable resin composition.

[0188] Example 6 <Preparation of Colored Curable Resin Composition> (A) Colorant: CI Disperse Yellow 82 9.4 parts (A) Colorant: Dye (A-1) 1 part (B) Resin: Resin (B-1) (solid content equivalent) 50 parts (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 7 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: propylene glycol monomethyl ether acetate 145 parts (E) Solvent: N-methylpyrrolidone 521 parts The above components were mixed to obtain a colored curable resin composition.

[0189] Example 7 <Preparation of Colored Curable Resin Composition> (A) Colorant: Dye (AII-8) 4.9 parts (A) Colorant: CI Disperse Yellow 82 4.9 parts (A) Colorant: Dye (A-1) 4.9 parts (B) Resin: Resin (B-1) (solid content equivalent) 50 parts (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 7 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: 237 parts of propylene glycol monomethyl ether acetate (E) Solvent: N-methylpyrrolidone 452 parts The above components were mixed to obtain a colored curable resin composition.

[0190] Example 8 <Preparation of Colored Curable Resin Composition> (A) Colorant: Dye (AII-X) 9.8 parts (A) Coloring agent: Dye (A-1) 5 parts (B) Resin: Resin (B-1) (solid content equivalent) 50 parts (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 7 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: propylene glycol monomethyl ether acetate 145 parts (E) Solvent: N-methylpyrrolidone 546 parts The above components were mixed to obtain a colored curable resin composition.

[0191] Example 9 <Preparation of Colored Curable Resin Composition> (A) Colorant: Dye (AII-Y) 9.8 parts (A) Coloring agent: Dye (A-1) 5 parts (B) Resin: Resin (B-1) (solid content equivalent) 50 parts (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 7 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: propylene glycol monomethyl ether acetate 145 parts (E) Solvent: N-methylpyrrolidone 546 parts The above components were mixed to obtain a colored curable resin composition.

[0192] Comparative Example 3 <Preparation of Colored Curable Resin Composition> (A) Colorant: Dye (AII-Y) 9.3 parts (B) Resin: Resin (B-1) (solid content equivalent) 50 parts (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 7 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: propylene glycol monomethyl ether acetate 145 parts (E) Solvent: N-methylpyrrolidone 515 parts The above components were mixed to obtain a colored curable resin composition.

[0193] <Color evaluation> The spectrum of the obtained colored pattern was measured using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and the xy chromaticity coordinates (x, y) and stimulus value Y in the CIE XYZ color system were measured using the characteristic function of the C light source.

[0194] <Light resistance evaluation> An ultraviolet ray-cutting filter (COLORED OPTICAL GLASS L38; manufactured by Hoya; cuts out light of 380 nm or less) was placed on the obtained colored pattern, and the pattern was irradiated with xenon lamp light for 48 hours using a light resistance tester (Suntest CPS+; manufactured by Toyo Seiki Co., Ltd.). The xy chromaticity coordinates (x, y) and Y were measured before and after irradiation, and the color difference ΔEab* was calculated from the measured values ​​according to the method described in JIS Z 8730:2009 (7. Calculation method of color difference), and the results are shown in Table 4. The smaller ΔEab* means the smaller the color change.

[0195] [Table 4]

[0196] It was confirmed that the color filters obtained using the colored curable resin compositions of the Examples exhibited excellent light resistance.

Claims

1. The composition contains a colorant, an alkali-soluble resin, a polymerizable compound having an ethylenically unsaturated bond, and a polymerization initiator, A colored curable resin composition, comprising a colorant comprising at least one dye selected from the group consisting of squarylium dyes and coumarin dyes, and an anthraquinone dye having a carboxy group.

2. 2. The colored curable resin composition according to claim 1, wherein the anthraquinone dye having a carboxy group is a compound represented by formula (A1). 【Chemistry 1】 [In formula (A1), A 1a and A 2a each independently represents a phenylene group which may have a substituent. L 1a and L 2a each independently represents a divalent hydrocarbon group having 1 to 15 carbon atoms, 2 - is -O-, -SO 2 -or-NR 11a However, adjacent -CH 2 - cannot be simultaneously substituted with the same group. R 1a ~R 6a R each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 8 carbon atoms. 11a represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.

3. A color filter formed from the colored curable resin composition according to claim 1 or 2.

4. A display device comprising the color filter according to claim 3.

Images