Coloring curable resin composition, color filter, and display device

Abstract

The present invention provides a colored curable resin composition, a color filter, and a display device capable of forming a color filter with excellent light resistance. The colored curable resin composition of the present invention is characterized by containing a colorant, a resin, a polymerizable compound, and a polymerization initiator. The colorant includes at least one selected from the group consisting of squarylium dyes and coumarin dyes, and an anthraquinone dye having a carboxyl group.

Description

Technical Field

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

[0002] Color filters used in display devices such as liquid crystal display devices, electroluminescent display devices, and plasma display panels, and solid-state imaging elements such as CCDs or CMOS sensors are manufactured from colored curable resin compositions. As such colored curable resin compositions, 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) are known.

[0003] Prior Art Documents

[0004] Patent Documents

[0005] Patent Document 1: Japanese Unexamined Patent Application Publication No. 2015-86379

[0006] Patent Document 2: Japanese Unexamined Patent Application Publication No. 2015-44982 Summary of the Invention

[0007] Problems to be Solved by the Invention

[0008] However, color filters formed from the above-described colored curable resin compositions have not been able to sufficiently satisfy light resistance.

[0009] Means for Solving the Problems

[0010] The gist of the present invention is as follows.

[0011] [1] A colored curable resin composition, comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator,

[0012] The colorant includes at least one selected from the group consisting of a squarylium dye and a coumarin dye, and an anthraquinone dye having a carboxyl group.

[0013] [2] The colored curable resin composition according to [1], wherein the anthraquinone dye having a carboxyl group is a compound represented by formula (A1).

[0014] [Chemical Formula 1]

[0015]

[0016] [In formula (A1),

[0017] A 1a and A 2a each independently represent a phenylene group which may have a substituent.

[0018] L1a and L 2a each independently represents a divalent hydrocarbon group having 1 to 15 carbon atoms, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -SO2- or -NR 11a -. Among them, adjacent -CH2- will not be replaced by the same group at the same time.

[0019] R 1a to R 6a each independently represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 8 carbon atoms. R 11a represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.]

[0020] [3] A color filter formed from the color-curable resin composition described in [1] or [2].

[0021] [4] A display device comprising the color filter described in [3].

[0022] Advantages of the Invention

[0023] The color-curable resin composition according to the present invention can form a color filter with excellent light resistance. Detailed Embodiments

[0024] The color-curable resin composition of the present invention contains a colorant (hereinafter sometimes referred to as colorant (A)), a resin (hereinafter sometimes referred to as resin (B)), a polymerizable compound (hereinafter sometimes referred to as polymerizable compound (C)), and a polymerization initiator (hereinafter sometimes referred to as polymerization initiator (D)).

[0025] The color-curable resin composition of the present invention preferably further contains a solvent (hereinafter sometimes referred to as solvent (E)).

[0026] The color-curable resin composition of the present invention may contain a leveling agent.

[0027] In this specification, the compounds exemplified as each component can be used alone or in combination of multiple kinds unless otherwise specified.

[0028] <Colorant (A)>

[0029] The colorant contains at least one selected from the group consisting of squarylium dyes and coumarin dyes, and an anthraquinone dye having a carboxyl group. Preferably, it is a combination of a squarylium dye and an anthraquinone dye having a carboxyl group, a combination of a coumarin dye and an anthraquinone dye having a carboxyl group, or a combination of a squarylium dye, a coumarin dye and an anthraquinone dye having a carboxyl group. Each of the squarylium dyes, coumarin dyes, or anthraquinone dyes described later can be one or two kinds.

[0030] <Anthraquinone Dye Having a Carboxyl Group>

[0031] The anthraquinone dye having a carboxyl group may be a compound having at least one (preferably two) carboxyl groups, and is preferably a compound represented by the formula (A1).

[0032] [Chemical formula 2]

[0033]

[0034] [In the formula (A1),

[0035] A 1a and A 2a each independently represent a phenylene group which may have a substituent.

[0036] L 1a and L 2a each independently represent a divalent hydrocarbon group having 1 to 15 carbon atoms, and -CH2- contained in the hydrocarbon group may be substituted by -O-, -SO2- or -NR 11a -. Among them, adjacent -CH2- will not be substituted by the same group at the same time.

[0037] R 1a to R 6a each independently represent a hydrogen atom, a halogen atom or an alkyl group having 1 to 8 carbon atoms. R 11a represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.]

[0038] As the substituents that the phenylene group represented by A 1a and A 2a may have, there may be mentioned 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 R 21a represents a saturated hydrocarbon group having 1 to 20 carbon atoms, and R 21a in -R 21a is preferably an alkyl group having 1 to 8 carbon atoms. The above R 12a and R 13a each independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms or an aralkyl group having 7 to 10 carbon atoms, and R 12a and R 13a may together form a ring containing a nitrogen atom. G +is Na + , K + , or N + (R 15a )4, T + is Na + , K + , or N + (R 16a )4, the 4 Rs 15a can be the same or different, and the 4 Rs 16a can be the same or different. R 15a and R 16a represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms.

[0039] Regarding the halogen atoms, R 1a to R 2a which can be substituents of the phenylene group represented by A 1a and A 6a , examples of the halogen atoms include a chlorine atom, a bromine atom, a fluorine atom, an iodine atom, etc. Among them, a chlorine atom and a bromine atom are preferred.

[0040] As the substituents that the phenylene group represented by A 1a and A 2a can have, -R 21a , -SO3H, -SO3 - G + , -COOH, -COO - T + and -SO2NR 12a R 13a are preferred. As -SO3 - G + at this time, -SO3 - N + (R 15a )4 is preferred. The most preferred substituent is -R 21a .

[0041] As the alkyl group having 1 to 8 carbon atoms represented by R 1a to R 6a , R 11a , R 15a , R 16a , and R 21a , for example, linear alkyl groups such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, etc.; branched alkyl groups such as an isopropyl group, an isobutyl group, an isopentyl group, a neopentyl group, etc. Among them, as R 1a to R 6a and R 11a , a hydrogen atom is preferred. R 21aThe alkyl group having 1 to 8 carbon atoms represented is more preferably methyl, ethyl, propyl or butyl, and still more preferably methyl or ethyl.

[0042] The substitution position in the phenylene group may be any position as long as it is a part excluding two bonding sites, and two or more positions may be substituted. When two or more positions are substituted, the substituents may be the same or different.

[0043] As R 12a , R 13a and R 21a The saturated hydrocarbon group having 1 to 20 carbon atoms represented, for example, may include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, icosyl; branched alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, 2-ethylhexyl; alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, tricyclodecyl. The number of carbon atoms of the saturated hydrocarbon group is more preferably 1 to 10, still more preferably 1 to 8, and even more preferably 1 to 5.

[0044] As R 12a and R 13a The aralkyl group having 7 to 10 carbon atoms represented may include benzyl, phenylethyl, phenylbutyl, etc.

[0045] As R 12a and R 13a The ring containing a nitrogen atom formed together, for example, may include the following rings. In the formula, * represents a bonding site.

[0046] [Chemical formula 3]

[0047]

[0048] As N + (R 15a )4, N + (R 16a )4, examples may include tetramethylammonium, tetraethylammonium, tetrapropylammonium, tetrabutylammonium, etc.

[0049] As -OR 21a , for example, may include alkoxy groups such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy and icosyloxy.

[0050] As -CO2R 21a , for example, may include alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, tert-butoxycarbonyl, hexyloxycarbonyl and icosyloxycarbonyl.

[0051] As - SR 21a , for example, alkylthio groups such as methylthio, ethylthio, butylthio, hexylthio, decylthio, and eicosylthio can be cited.

[0052] As - SO2R 21a , for example, alkylsulfonyl groups such as methylsulfonyl, ethylsulfonyl, butylsulfonyl, hexylsulfonyl, decylsulfonyl, and eicosylsulfonyl can be cited.

[0053] As - SO3R 21a , for example, alkoxysulfonyl groups such as methoxysulfonyl, ethoxysulfonyl, propoxysulfonyl, tert - butoxysulfonyl, hexoxysulfonyl, and eicosoxysulfonyl can be cited.

[0054] As - SO2NR 12a R 13a , for example, sulfamoyl group can be cited;

[0055] N - methylsulfamoyl, N - ethylsulfamoyl, N - propylsulfamoyl, N - isopropylsulfamoyl, N - butylsulfamoyl, N - isobutylsulfamoyl, N - sec - butylsulfamoyl, N - tert - butylsulfamoyl, N - pentylsulfamoyl, N-(1 - ethylpropyl)sulfamoyl, N-(1,1 - dimethylpropyl)sulfamoyl, N-(1,2 - dimethylpropyl)sulfamoyl, N-(2,2 - dimethylpropyl)sulfamoyl, N-(1 - methylbutyl)sulfamoyl, N-(2 - methylbutyl)sulfamoyl, N-(3 - methylbutyl)sulfamoyl, N - cyclopentylsulfamoyl, N - hexylsulfamoyl, N-(1,3 - dimethylbutyl)sulfamoyl, N-(3,3 - dimethylbutyl)sulfamoyl, N - heptylsulfamoyl, N-(1 - methylhexyl)sulfamoyl, N-(1,4 - dimethylpentyl)sulfamoyl, N - octylsulfamoyl, N-(2 - ethylhexyl)sulfamoyl, N-(1,5 - dimethylhexyl)sulfamoyl, N-(1,1,2,2 - tetramethylbutyl)sulfamoyl and other N - 1 substituted sulfamoyl groups;

[0056] N,N - dimethylsulfamoyl, N,N - ethylmethylsulfamoyl, N,N - diethylsulfamoyl, N,N - propylmethylsulfamoyl, N,N - isopropylmethylsulfamoyl, N,N - tert - butylmethylsulfamoyl, N,N - butylethylsulfamoyl, N,N - bis(1 - methylpropyl)sulfamoyl, N,N - heptylmethylsulfamoyl and other N,N - 2 substituted sulfamoyl groups, etc.

[0057] As for forming L 1a and L 2aThe divalent hydrocarbon group having 1 to 15 carbon atoms represented may include aliphatic hydrocarbons having 1 to 12 carbon atoms, benzene, aromatic hydrocarbons having 6 to 15 carbon atoms such as benzene having an alkyl group with 1 to 8 carbon atoms. As the divalent aliphatic hydrocarbon group having 1 to 15 carbon atoms, there may be mentioned straight-chain alkanediyl groups having a bonding bond at both ends such as methylene, ethane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, branched-chain alkanediyl groups such as ethane-1,1-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-2,2-diyl, butane-1,1-diyl, butane-1,2-diyl, butane-1,3-diyl, butane-2,2-diyl, butane-2,3-diyl, 2-methylpropane-1,1-diyl, 2-methylpropane-1,2-diyl, 2-methylpropane-1,3-diyl, 2-methylbutane-1,4-diyl, 2-methylbutane-2,3-diyl, 2-methylbutane-2,4-diyl, 2-methylbutane-3,3-diyl, 2-methylbutane-3,4-diyl, 2-methylbutane-4,4-diyl, and cyclic alkanediyl groups such as cyclohexane-1,4-diyl, cyclohexane-1,4-dimethylene. Among them, straight-chain alkanediyl groups are preferred.

[0058] As benzene having an alkyl group with 1 to 8 carbon atoms and inducing a divalent aromatic hydrocarbon group having 6 to 15 carbon atoms, there may be mentioned methylbenzene, dimethylbenzene, ethylbenzene, propylbenzene, ethyl(methyl)benzene, butylbenzene, ethyl(dimethyl)benzene, etc. The divalent group formed by removing two hydrogen atoms from the benzene having an alkyl group with 1 to 8 carbon atoms may be in a form having two bonding bonds on the alkyl group, may be in a form having two bonding bonds on the benzene ring, or may be in a form having one bonding bond on the alkyl group and one bonding bond on the benzene ring. Among them, the form having one bonding bond on the alkyl group and one bonding bond on the benzene ring is preferred.

[0059] L 1a and L 2a The number of carbon atoms of the divalent hydrocarbon group represented is preferably 2 to 15, more preferably 3 to 13, and still more preferably 4 to 11.

[0060] -CH2- contained in the hydrocarbon group may be replaced by -O-, -SO2- or -NR 11a -, and the number of carbon atoms of the hydrocarbon group is defined as the number of carbon atoms before being replaced by these groups.

[0061] Among them, L 1a and L 2a The divalent hydrocarbon group represented is particularly preferably a divalent group formed by removing two hydrogen atoms from benzene having an alkyl group with 1 to 8 carbon atoms, and particularly preferably has one bonding bond on the alkyl group and one bonding bond on the benzene ring.

[0062] One bonding site of the preferred alkyl group is bonded to A 1a or A 2a is bonded, and one bonding site of the benzene ring is bonded to CO2H.

[0063] As the anthraquinone dye, preferably the *-L of formula (A1) 1a -** (* represents the bonding site to A 1a bonding site, ** represents the bonding site to CO2H) and *-L 2a -** (* represents the bonding site to A 2a bonding site, ** represents the bonding site to CO2H) are each independently a compound having any one of the structures represented by formulas (A1A) to (A1h).

[0064] *-O-R 31a -** (A1A)

[0065] *-O-R 32a -** (A1b)

[0066] *-O-R 33a -R 32a -** (A1c)

[0067] *-O-R 32a -R 33a -** (A1d)

[0068] *-SO2-NH-R 31a -** (A1e)

[0069] *-SO2-NH-R 34a -** (A1f)

[0070] *-SO2-NH-R 33a -R 34a -** (A1g)

[0071] *-SO2-NH-R 34a -R 33a -** (A1h)

[0072] [In the formula, R 31a represents an alkanediyl group having 1 to 10 carbon atoms, R 32a and R 34a represent a phenylene group which may be bonded to an alkyl group having 1 to 4 carbon atoms, and R 33a represents an alkanediyl group having 1 to 4 carbon atoms. Among them, the number of carbon atoms of R 32a is 14 or less, and the number of carbon atoms of R 33a is 13 or less. In addition, the sum of the number of carbon atoms of R 32a and R 33a is 14 or less, R33a and R 34a The sum of the number of carbon atoms of is 13 or less. * indicates the bond with A 1a or A 2a bond, ** indicates the bond with CO2H.]

[0073] R 31a alkanediyl having 1 to 10 carbon atoms represented by and R 33a alkanediyl having 1 to 4 carbon atoms represented by can be the same as the groups exemplified as the divalent hydrocarbon group represented by L 1a and L 2a divalent hydrocarbon group (preferably alkanediyl exemplified as a divalent saturated hydrocarbon group).

[0074] R 32a and R 34a The phenylene group which may be bonded to an alkyl group having 1 to 4 carbon atoms can be the same as the group exemplified as benzene having an alkyl group having 1 to 8 carbon atoms and having two bonds on the benzene ring.

[0075] R 32a and R 34a More preferably 6-methyl-1,3-phenylene, 5-methyl-1,3-phenylene or 4-methyl-1,3-phenylene.

[0076] (A1A) to (A1h), preferably (A1A), (A1f), etc.

[0077] As the anthraquinone dye, a compound represented by the formula (A1X) can be exemplified. Specific examples of the compound represented by the formula (A1X) are represented by the numbers (A1X-1) to (A1X-36) in Table 1.

[0078] [Chemical formula 4]

[0079]

[0080] [Table 1]

[0081]

[0082] In Table 1, Me represents methyl, and RX1 to RX5 and RY1 to RY4 respectively represent the groups represented by the following formulas. In the following formulas, * indicates a bond.

[0083] [Chemical formula 5]

[0084]

[0085] Among them, those preferably further include compounds represented by Nos. (A1X-6) to (A1X-9), compounds represented by Nos. (A1X-15) to (A1X-18), compounds represented by Nos. (A1X-24) to (A1X-27), and compounds represented by Nos. (A1X-33) to (A1X-36).

[0086] The anthraquinone compound (A1) can be produced according to a known method.

[0087] The content rate of the anthraquinone dye is, for example, 5% by mass or more, preferably 10% by mass or more, more preferably 15% by mass or more, for example, 50% by mass or less, preferably 45% by mass or less, and more preferably 40% by mass or less with respect to the total amount of the colorant (A).

[0088] The content rate of the anthraquinone dye is, for example, 1% by mass or more, preferably 2% by mass or more, more preferably 3% by mass or more, for example, 30% by mass or less, preferably 25% by mass or less, and more preferably 20% by mass or less with respect to the solid content of the colored curable resin composition.

[0089] <Squarylium dye>

[0090] The squarylium dye is preferably a compound represented by the formula (A1-2’).

[0091] [Chemical formula 6]

[0092]

[0093] [In the formula (A1-2’), A + and B each independently represent an organic group containing an aromatic ring or a heterocyclic ring.]

[0094] The compound represented by the formula (A1-2’) also includes all compounds having a resonance structure possible for the structure represented by the formula (A1-2’).

[0095] As the squarylium compound represented by the formula (A1-2’), for example, compounds described in JP-A-2013-76926 can be exemplified. Among the compounds represented by the formula (A1-2’), the compound represented by the formula (A1-2) is preferred as the squarylium compound.

[0096] [Chemical formula 7]

[0097]

[0098] [In the formula (A1-2),

[0099] 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. The 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-. Among them, adjacent -CH2- will not be substituted with the same group at the same time, and in addition, the terminal -CH2- will not be substituted either.

[0100] R 5 ~R 8 Each independently represents a hydrogen atom or a hydroxyl group.

[0101] 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.

[0102] 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. The 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 substituted with -O- or -S-. Among them, adjacent -CH2- will not be substituted with the same group at the same time, and in addition, the terminal -CH2- will not be substituted either.

[0103] As the halogen atom in R 1 ~R 4 Examples include a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.

[0104] As the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in R 1 ~R 4 、R 11 and R 12 Examples 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 eicosyl; branched alkyl groups having 3 to 20 carbon atoms such as isopropyl, isobutyl, sec-butyl, tert-butyl, 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.

[0105] R 1 ~R 4 、R 11 and R 12 The number of carbon atoms of the monovalent saturated hydrocarbon group in R ~R 、R and R is preferably 1 to 18, more preferably 2 to 15, further preferably 2 to 12, and even more preferably 3 to 9.

[0106] Examples of the group in which a hydrogen atom contained in these saturated hydrocarbon groups is 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.

[0107] Examples of the group in which a hydrogen atom contained in a saturated hydrocarbon group is substituted with a hydroxyl group include a hydroxyethyl group, a hydroxybutyl group, and a hydroxyhexyl group.

[0108] 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.

[0109] Examples of the group in which -CH2- constituting a monovalent saturated hydrocarbon group is substituted with -O- or -S- include the groups represented by the following formula. In the following formula, * represents a bonding site.

[0110] [Chemical formula 8]

[0111]

[0112] As the group that can substitute R 9 and R 10 with a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms, in addition to the above-mentioned monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, a monovalent unsaturated hydrocarbon group having 2 to 20 carbon atoms can also be mentioned. 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.

[0113] Among them, an alkyl group having 1 to 4 carbon atoms is preferred, and a methyl group and an ethyl group are more preferred.

[0114] Examples of the phenyl group that can be substituted with a monovalent aliphatic hydrocarbon group having 1 to 20 carbon atoms include a phenyl group, a toluoyl group, and the groups represented by the following formula. * represents a bonding site with a nitrogen atom.

[0115] [Chemical formula 9]

[0116]

[0117] R 1 ~R 4 Each independently is preferably a hydrogen atom, a hydroxyl group, or a methyl group, and more preferably a hydrogen atom.

[0118] R 5 ~R 8 Each independently is preferably a hydrogen atom, a hydroxyl group, or a methyl group, more preferably a hydrogen atom or a hydroxyl group. Further preferably, R5 and R 8 is a hydroxyl group.

[0119] R 9 and R 10 are each independently preferably a phenyl group substituted with one or more alkyl groups having 1 to 4 carbon atoms, or a phenyl group, more preferably a phenyl group having one or more methyl and / or ethyl groups as substituents, or a phenyl group.

[0120] R 11 and R 12 are preferably a phenyl group that can 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, further preferably a monovalent saturated hydrocarbon group having 2 to 18 carbon atoms, still further preferably a monovalent saturated hydrocarbon group having 3 to 15 carbon atoms, and even further preferably a monovalent saturated hydrocarbon group having 4 to 12 carbon atoms, and particularly preferably butyl or 2-ethylhexyl.

[0121] In formula (A1-2), as the following formula (X 1 ) and formula (X 2 ), for example, groups represented by formula (A2-1) to (A2-8) and groups represented by formula (B2-1) to (B2-8) can be cited. * represents a bonding site to a carbon atom.

[0122] [Chemical formula 10]

[0123]

[0124] [Chemical formula 11]

[0125]

[0126] [Chemical formula 12]

[0127]

[0128] [Chemical formula 13]

[0129]

[0130] As the compound represented by formula (A1-2), for example, compounds (C2-1) to (C2-24) shown in Table 2 and compounds (D2-1) to (D2-24) shown in Table 3 can be cited.

[0131] [Table 2]

[0132] Compound <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > R6 <![CDATA[R 7 > <![CDATA[R 8 > <![CDATA[X 1 > <![CDATA[X 2 > C2-1 H H H H H H H H A2-1 A2-1 C2-2 H H H H H H H H A2-2 A2-2 C2-3 H H H H H H H H A2-3 A2-3 C2-4 H H H H H H H H A2-4 A2-4 C2-5 H H H H H H H H A2-5 A2-5 C2-6 H H H H H H H H A2-6 A2-6 C2-7 H H H H H H H H A2-7 A2-7 C2-8 H H H H H H H H A2-8 A2-8 C2-9 H H H H OH H H OH A2-1 A2-1 C2-10 H H H H OH H H OH A2-2 A2-2 C2-11 H H H H OH H H OH A2-3 A2-3 C2-12 H H H H OH H H OH A2-4 A2-4 C2-13 H H H H OH H H OH A2-5 A2-5 C2-14 H H H H OH H H OH A2-6 A2-6 C2-15 H H H H OH H H OH A2-7 A2-7 C2-16 H H H H OH H H OH A2-8 A2-8 C2-17 H H H H OH OH OH OH A2-1 A2-1 C2-18 H H H H OH OH OH OH A2-2 A2-2 C2-19 H H H H OH OH OH OH A2-3 A2-3 C2-20 H H H H OH OH OH OH A2-4 A2-4 C2-21 H H H H OH OH OH OH A2-5 A2-5 C2-22 H H H H OH OH OH OH A2-6 A2-6 C2-23 H H H H OH OH OH OH A2-7 A2-7 C2-24 H H H H OH OH OH OH A2-8 A2-8

[0133] [Table 3]

[0134] Compound <![CDATA[R 1 > <![CDATA[R 2 > <![CDATA[R 3 > <![CDATA[R 4 > <![CDATA[R 5 > <![CDATA[R 6 > <![CDATA[R 7 > <![CDATA[R 8 > <![CDATA[X 1 > <![CDATA[X 2 > D2-1 H H H H H H H H B2-1 B2-1 D2-2 H H H H H H H H B2-2 B2-2 D2-3 H H H H H H H H B2-3 B2-3 D2-4 H H H H H H H H B2-4 B2-4 D2-5 H H H H H H H H B2-5 B2-5 D2-6 H H H H H H H H B2-6 B2-6 D2-7 H H H H H H H H B2-7 B2-7 D2-8 H H H H H H H H B2-8 B2-8 D2-9 H H H H OH H H OH B2-1 B2-1 D2-10 H H H H OH H H OH B2-2 B2-2 D2-11 H H H H OH H H OH B2-3 B2-3 D2-12 H H H H OH H H OH B2-4 B2-4 D2-13 H H H H OH H H OH B2-5 B2-5 D2-14 H H H H OH H H OH B2-6 B2-6 D2-15 H H H H OH H H OH B2-7 B2-7 D2-16 H H H H OH H H OH B2-8 B2-8 D2-17 H H H H OH OH OH oH B2-1 B2-1 D2-18 H H H H OH OH OH OH B2-2 B2-2 D2-19 H H H H OH OH OH OH B2-3 B2-3 D2-20 H H H H OH OH OH OH B2-4 B2-4 D2-21 H H H H OH OH OH OH B2-5 B2-5 D2-22 H H H H OH OH OH OH B2-6 B2-6 D2-23 H H H H OH OH OH OH B2-7 B2-7 D2-24 H H H H OH OH OH OH B2-8 B2-8

[0135] From the viewpoint of raw material availability, compounds (C2-9) to compounds (C2-16) and compounds (D2-9) to compounds (D2-16) are preferred, and compounds (C2-9) (compounds represented by formula (AII-8) described later) and compounds (D2-9) (compounds represented by formula (AII-X) described later) are more preferred.

[0136] The compound represented by formula (A1-2) can be produced, for example, according to the method described in JP-A-2002-363434.

[0137] The content rate of the squarylium dye is, for example, 10% by mass or more, preferably 20% by mass or more, more preferably 30% by mass or more, for example, 95% by mass or less, preferably 90% by mass or less, more preferably 80% by mass or less, relative to the total amount of the colorant (A).

[0138] In addition, the content rate of the squarylium dye is, for example, 2% by mass or more, preferably 4% by mass or more, more preferably 6% by mass or more, for example, 60% by mass or less, preferably 50% by mass or less, more preferably 40% by mass or less, relative to the solid content of the colored curable resin composition.

[0139] <Coumarin Dye>

[0140] The coumarin dye may be any compound having a coumarin skeleton in the molecule. Examples of the coumarin dye include C.I. Acid Yellow 227, 250; C.I. Disperse Yellow 82, 184; C.I. Solvent Orange 112; C.I. Solvent Yellow 160, 172; coumarin compounds described in Japanese Patent No. 1299948, JP-A-2013-151668, JP-A-2013-231165, JP-A-2014-51641, JP-A-2015-44982, WO 2014 / 208767, etc.

[0141] The coumarin dye is preferably a compound represented by formula (A1-3) and / or a compound represented by formula (A1-4).

[0142] [Chemical Formula 14]

[0143]

[0144] [In formula (A1-3),

[0145] R 71 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0146] 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.

[0147] s represents an integer of 0 to 3. When s is an integer of 2 or more, a plurality of Rs 72 may be the same or different.

[0148] t represents an integer of 0 to 4. When t is an integer of 2 or more, a plurality of Rs 73 may be the same or different.

[0149] As the hydrocarbon group in R 71 to R 73 aliphatic hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups can be mentioned. The aliphatic hydrocarbon group may be saturated or unsaturated, and examples thereof include alkyl groups, alkenyl groups, and alkynyl groups. The alicyclic hydrocarbon group may be saturated or unsaturated, and examples thereof include cycloalkyl groups, cycloalkenyl groups, condensed polycyclic hydrocarbon groups, bridged cyclic hydrocarbon groups, spiro hydrocarbon groups, cyclic terpene olefin groups, etc. Aromatic hydrocarbon groups can be mentioned such as phenyl group, toluoyl group, etc. Among them, an alkyl group having 1 to 8 carbon atoms is preferred, and an alkyl group having 1 to 4 carbon atoms is more preferred.

[0150] In addition, examples of the substituent of the hydrocarbon group include a halogen atom, an alkoxy group having 1 to 8 carbon atoms, a hydroxyl group, a nitro group, a carboxyl group, a sulfo group, a sulfamoyl group, a carbamoyl group, an N-substituted sulfamoyl group, an alkoxycarbonyl group, etc. When having a sulfo group as a substituent, the sulfo group may be in the form of a salt.

[0151] As the halogen atom in R 72 and R 73 chlorine atom, fluorine atom, bromine atom, iodine atom, etc. can be mentioned.

[0152] As the alkoxy group in R 72 and R 73 an alkoxy group having 1 to 8 carbon atoms is preferred, and an alkoxy group having 1 to 4 carbon atoms is more preferred.

[0153] R 72 and R 73 the amino group in preferably has a substituent. As the N-position substituent, an alkyl group having 1 to 8 carbon atoms is preferred, and an alkyl group having 1 to 4 carbon atoms is more preferred.

[0154] s is preferably 1. In this 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.

[0155] t is preferably 0.

[0156] As specific examples of the compound represented by formula (A1-3), compounds represented by formula (A1-3-1) or formula (A1-3-2) etc. can be cited, for example.

[0157] [Chemical formula 15]

[0158]

[0159] The compound represented by formula (A1-4) (hereinafter, also referred to as (A1-4) compound) is as follows.

[0160] [Chemical formula 16]

[0161]

[0162] (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 may be substituted by 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 substituted by a halogen atom, a cyano group, a nitro group, a carbamoyl group, a sulfamoyl group, -SO3M, -CO2M, a hydroxyl 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, and when there are a plurality of R 14 , they may be the same or different, M represents a hydrogen atom or an alkali metal atom, and when there are a plurality of M, they may be the same or different.

[0163] Z is of formula (Z1):

[0164] [Chemical formula 17]

[0165]

[0166] (In the formula, R 1 represents an alkyl group having 1 to 20 carbon atoms, and -CH2- constituting the alkyl group may be substituted by an oxygen atom, 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 may be substituted by an oxygen atom, a sulfur atom, -N(R30 )-, a sulfonyl group or a carbonyl group, and the hydrogen atoms contained in the hydrocarbon group may be substituted with a halogen atom, a cyano group, a nitro group, a carbamoyl group, a sulfamoyl group, -SO3M, -CO2M, a hydroxyl group, a formyl group or an amino group, R 30 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms. When there are a plurality of R 30 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. * represents a bonding site.)

[0167] 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-).

[0168] Examples of the divalent fluorinated hydrocarbon group having 1 to 20 carbon atoms include the groups represented by formula (L1) to formula (L12). From the viewpoint of the availability of raw materials, the groups represented by formula (L1), formula (L7), formula (L8), formula (L10) or formula (L11) are preferred, the groups represented by formula (L1), formula (L7), formula (L8) or formula (L11) are more preferred, and the group represented by formula (L1) is particularly preferred. In the following formula (L1) to formula (L12), ● represents a bonding site.

[0169] [Chemical formula 18]

[0170]

[0171] Examples of the divalent hydrocarbon group having 1 to 20 carbon atoms include methylene, dimethylene, trimethylene, tetramethylene, 1,1-ethylene, 2,2-propylene, fluorene-9,9-diyl, etc., and a divalent hydrocarbon group having 1 to 16 carbon atoms is preferred.

[0172] 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. From the viewpoint of the availability of raw materials, it is preferably any one of the groups represented by the following formula (L21) to formula (L24), more preferably any one of the groups represented by formula (L21) to formula (L23), and particularly preferably the group represented by formula (L21) or formula (L22). In the following formula, ● represents a bonding site.

[0173] [Chemical formula 19]

[0174]

[0175] In formula (A1-4), X represents an oxygen atom or a sulfur atom, 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.

[0176] 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 may be replaced by 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 (-CONH2), a sulfamoyl group (-SO2NH2), -SO3M, -CO2M, a hydroxyl 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, and when there are a plurality of R 14 , they may be the same or different.

[0177] M represents a hydrogen atom or an alkali metal atom, and when there are a plurality of M, they may be the same or different. Examples of the alkali metal atom include a sodium atom and a potassium atom. M is preferably a hydrogen atom.

[0178] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0179] Examples of the monovalent hydrocarbon group having 1 to 20 carbon atoms include aliphatic hydrocarbon groups such as methyl, ethyl, propyl, isopropyl, isopropenyl, 1-propenyl, 2-propenyl, butyl, isobutyl, sec-butyl, tert-butyl, 2-ethyl-1-butyl, 2-buteneyl, 1,3-butadienyl, pentyl, isopentyl, 3-pentyl, neopentyl, tert-pentyl, 1-methyl-1-pentyl, 2-methyl-1-pentyl, 2-pentenyl, 3-ethyl-1-pentyl, hexyl, isohexyl, 5-methyl-1-hexyl, 2-ethyl-1-hexyl, heptyl, 3-ethyl-1-heptyl, octyl, nonyl, decyl, undecyl, dodecyl, octadecyl;

[0180] alicyclic hydrocarbon groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexenyl, cycloheptyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 1,2-dimethylcyclohexyl, 1,3-dimethylcyclohexyl, 1,4-dimethylcyclohexyl, 2,3-dimethylcyclohexyl, 2,4-dimethylcyclohexyl, 2,5-dimethylcyclohexyl, 2,6-dimethylcyclohexyl, 3,4-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, 2,2-dimethylcyclohexyl, 3,3-dimethylcyclohexyl, 4,4-dimethylcyclohexyl, 2,4,6-trimethylcyclohexyl, 2,2,6,6-tetramethylcyclohexyl, 3,3,5,5-tetramethylcyclohexyl;

[0181] 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, groups such as o-cumenyl, m-cumenyl, p-cumenyl, 2,6-bis(2-propyl)phenyl, 1-naphthyl, 2-naphthyl, biphenyl and other aromatic hydrocarbon groups; and groups formed by combining two or more of the above groups such as cyclohexylmethyl, benzyl, phenethyl.

[0182] As the -CH2- constituting the above monovalent hydrocarbon group is replaced by an oxygen atom, a sulfur atom, -N(R 14 )-, a sulfonyl group or a carbonyl group, and the hydrogen atom contained in the above monovalent hydrocarbon group is replaced by a halogen atom, a cyano group, a nitro group, a carbamoyl group, a sulfamoyl group, -SO3M, -CO2M, a hydroxyl group, a formyl group or an amino group, examples thereof include:

[0183] alkoxy groups such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, (2-ethyl-1-hexyl)oxy;

[0184] aryloxy groups such as phenoxy;

[0185] aralkyloxy groups such as benzyloxy;

[0186] Acyl groups such as acetyl, ethylcarbonyl, propylcarbonyl, isopropylcarbonyl, isopropenylcarbonyl, 1-propenylcarbonyl, 2-propenylcarbonyl, butylcarbonyl, isobutylcarbonyl, sec-butylcarbonyl, tert-butylcarbonyl, (1-ethyl-1-butyl)carbonyl, (2-ethyl-1-butyl)carbonyl, 2-butenylcarbonyl, 1,3-butadienylcarbonyl, pentylcarbonyl, isopentylcarbonyl, 3-pentylcarbonyl, neopentylcarbonyl, tert-pentylcarbonyl, (1-methyl-1-pentyl)carbonyl, (2-methyl-1-pentyl)carbonyl, 2-pentenylcarbonyl, (1-ethyl-1-pentyl)carbonyl, (3-ethyl-1-pentyl)carbonyl, hexylcarbonyl, isohexylcarbonyl, (5-methyl-1-hexyl)carbonyl, (2-ethyl-1-hexyl)carbonyl, heptylcarbonyl, (3-ethyl-1-heptyl)carbonyl, octylcarbonyl, nonylcarbonyl, decylcarbonyl, undecylcarbonyl, dodecylcarbonyl, cyclohexylmethylcarbonyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl;

[0187] Acetyloxy, benzoyloxy and other acyloxy groups;

[0188] Alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl;

[0189] Groups represented by the following formulas (GL-1) to (GL-8) (it should be noted that in the following formulas, ● represents a bonding site.);

[0190] [Chemical formula 20]

[0191]

[0192] Monosubstituted carbamoyl groups such as N-methylcarbamoyl, N-ethylcarbamoyl, N-propylcarbamoyl, N-isopropylcarbamoyl, N-butylcarbamoyl, N-isobutylcarbamoyl, N-sec-butylcarbamoyl, N-tert-butylcarbamoyl, N-pentylcarbamoyl, N-(1-ethyl-1-propyl)carbamoyl, N-(1,1-dimethyl-1-propyl)carbamoyl, N-(1,2-dimethyl-1-propyl)carbamoyl, N-(2,2-dimethyl-1-propyl)carbamoyl, N-(1-methyl-1-butyl)carbamoyl, N-(2-methyl-1-butyl)carbamoyl, N-(3-methyl-1-butyl)carbamoyl, N-cyclopentylcarbamoyl, N-hexylcarbamoyl, N-(1,3-dimethyl-1-butyl)carbamoyl, N-(3,3-dimethyl-1-butyl)carbamoyl, N-heptylcarbamoyl, N-(1-methyl-1-hexyl)carbamoyl, N-(1,4-dimethylpentyl)carbamoyl, N-octylcarbamoyl, N-(2-ethyl-1-hexyl)carbamoyl, N-(1,5-dimethyl-1-hexyl)carbamoyl, N-(1,1,2,2-tetramethyl-1-butyl)carbamoyl;

[0193] Disubstituted carbamoyl groups such as N,N-dimethylcarbamoyl, N,N-ethylmethylcarbamoyl, N,N-diethylcarbamoyl, N,N-propylmethylcarbamoyl, N,N-isopropylmethylcarbamoyl, N,N-tert-butylmethylcarbamoyl, N,N-butylethylcarbamoyl, N,N-bis(1-methyl-1-propyl)carbamoyl, N,N-heptylmethylcarbamoyl, N,N-bis(2-ethyl-1-hexyl)carbamoyl;

[0194] Monosubstituted sulfamoyl groups such as N-methylsulfamoyl, N-ethylsulfamoyl, N-propylsulfamoyl, N-isopropylsulfamoyl, N-butylsulfamoyl, N-isobutylsulfamoyl, N-sec-butylsulfamoyl, N-tert-butylsulfamoyl, N-pentylsulfamoyl, N-(1-ethyl-1-propyl)sulfamoyl, N-(1,1-dimethyl-1-propyl)sulfamoyl, N-(1,2-dimethyl-1-propyl)sulfamoyl, N-(2,2-dimethyl-1-propyl)sulfamoyl, N-(1-methyl-1-butyl)sulfamoyl, N-(2-methylbutyl)sulfamoyl, N-(3-methyl-1-butyl)sulfamoyl, N-cyclopentylsulfamoyl, N-hexylsulfamoyl, N-(1,3-dimethyl-1-butyl)sulfamoyl, N-(3,3-dimethyl-1-butyl)sulfamoyl, N-heptylsulfamoyl, N-(1-methyl-1-hexyl)sulfamoyl, N-(1,4-dimethyl-1-pentyl)sulfamoyl, N-octylsulfamoyl, N-(2-ethyl-1-hexyl)sulfamoyl, N-(1,5-dimethyl-1-hexyl)sulfamoyl, N-(1,1,2,2-tetramethyl-1-butyl)sulfamoyl;

[0195] Disubstituted sulfamoyl groups such as N,N-dimethylsulfamoyl, N,N-ethylmethylsulfamoyl, N,N-diethylsulfamoyl, N,N-propylmethylsulfamoyl, N,N-isopropylmethylsulfamoyl, N,N-tert-butylmethylsulfamoyl, N,N-butylethylsulfamoyl, N,N-bis(1-methyl-1-propyl)sulfamoyl, N,N-heptylmethylsulfamoyl, N,N-bis(2-ethyl-1-hexyl)sulfamoyl;

[0196] N-methylamino, N-ethylamino, N-propylamino, N-isopropylamino, N-butylamino, N-isobutylamino, N-sec-butylamino, N-tert-butylamino, N-pentylamino, N-(1-ethyl-1-propyl)amino, N-(1,1-dimethyl-1-propyl)amino, N-(1,2-dimethyl-1-propyl)amino, N-(2,2-dimethyl-1-propyl)amino, N-(1-methyl-1-butyl)amino, N-(2-methyl-1-butyl)amino, N-(3-methyl-1-butyl)amino, N-cyclopentylamino, N-hexylamino, N-(1,3-dimethyl-1-butyl)amino, N-(3,3-dimethyl-1-butyl)amino, N-heptylamino, N-(1-methyl-1-hexyl)amino, N-(1,4-dimethyl-1-pentyl)amino, N-octylamino, N-(2-ethyl-1-hexyl)amino, N-(1,5-dimethyl-1-hexyl)amino, N-(1,1,2,2-tetramethyl-1-butyl)amino and other N-alkylamino;

[0197] N,N-dimethylamino, N,N-ethylmethylamino, N,N-diethylamino, N,N-propylmethylamino, N,N-isopropylmethylamino, N,N-tert-butylmethylamino, N,N-butylethylamino, N,N-bis(1-methyl-1-propyl)amino, N,N-heptylmethylamino, N,N-bis(2-ethyl-1-hexyl)amino and other N,N-dialkylamino;

[0198] N-methylaminomethyl, N-ethylaminomethyl, N-propylaminomethyl, N-isopropylaminomethyl, N-butylaminomethyl, N-isobutylaminomethyl, N-sec-butylaminomethyl, N-tert-butylaminomethyl, N-pentylaminomethyl, N-(1-ethyl-1-propyl)aminomethyl, N-(1,1-dimethyl-1-propyl)aminomethyl, N-(1,2-dimethyl-1-propyl)aminomethyl, N-(2,2-dimethyl-1-propyl)aminomethyl, N-(1-methyl-1-butyl)aminomethyl, N-(2-methyl-1-butyl)aminomethyl, N-(3-methyl-1-butyl)aminomethyl, N-cyclopentylaminomethyl, N-hexylaminomethyl, N-(1,3-dimethyl-1-butyl)aminomethyl, N-(3,3-dimethyl-1-butyl)aminomethyl, N-heptylaminomethyl, N-(1-methyl-1-hexyl)aminomethyl, N-(1,4-dimethyl-1-pentyl)aminomethyl, N-octylaminomethyl, N-(2-ethyl-1-hexyl)aminomethyl, N-(1,5-dimethyl-1-hexyl)aminomethyl, N-(1,1,2,2-tetramethyl-1-butyl)aminomethyl and other N-alkylaminomethyl;

[0199] N,N-dimethylaminomethyl, N,N-ethylmethylaminomethyl, N,N-diethylaminomethyl, N,N-propylmethylaminomethyl, N,N-isopropylmethylaminomethyl, N,N-tert-butylmethylaminomethyl, N,N-butylethylaminomethyl, N,N-bis(1-methyl-1-propyl)aminomethyl, N,N-heptylmethylaminomethyl, N,N-bis(2-ethyl-1-hexyl)aminomethyl and other N,N-dialkylaminomethyl;

[0200] Trifluoromethyl, perfluoroethyl, perfluoropropyl, perfluoroisopropyl, perfluoroisopropenyl, perfluoro(1-propene) group, perfluoro(2-propene) group, perfluorobutyl, perfluoroisobutyl, perfluoro(sec-butyl) group, perfluoro(tert-butyl) group, perfluoro(2-butene) group, perfluoro(1,3-butadiene) group, perfluoropentyl, perfluoro(isopentyl) group, perfluoro(3-pentyl) group, perfluoroneopentyl, perfluoro(tert-pentyl) group, perfluoro(1-methylpentyl) group, perfluoro(2-methyl-1-pentyl) group, perfluoro(2-pentene) group, perfluorohexyl, perfluoroisohexyl, perfluoro(5-methyl-1-hexyl) group, perfluoro(2-ethyl-1-hexyl) group, perfluoroheptyl, perfluorooctyl, perfluorononyl, perfluorodecyl, perfluoroundecyl, perfluorododecyl, perfluorooctadecyl and other aliphatic hydrocarbon groups having fluorine atoms;

[0201] Perfluorocyclopropyl, perfluorocyclobutyl, perfluorocyclopentyl, perfluorocyclohexyl, perfluorocyclohexenyl, perfluorocycloheptyl, 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-dimethylcyclohexyl) group, perfluoro(2,5-dimethylcyclohexyl) group, perfluoro(2,6-dimethylcyclohexyl) group, perfluoro(3,4-dimethylcyclohexyl) group, perfluoro(3,5-dimethylcyclohexyl) group, perfluoro(2,2-dimethylcyclohexyl) group, perfluoro(3,3-dimethylcyclohexyl) group, perfluoro(4,4-dimethylcyclohexyl) group, perfluoro(2,4,6-trimethylcyclohexyl) group, perfluoro(2,2,6,6-tetramethylcyclohexyl) group, perfluoro(3,3,5,5-tetramethylcyclohexyl) group and other alicyclic hydrocarbon groups having fluorine atoms;

[0202] Perfluorophenyl, perfluoro(o-tolyl) group, perfluoro(m-tolyl) group, perfluoro(p-tolyl) group, perfluoroxylenyl, perfluoro group, perfluoro(o-cumyl) group, perfluoro(m-cumyl) group, perfluoro(p-cumyl) group, perfluorobenzyl, perfluorophenethyl, perfluorobiphenyl group, perfluoro(1-naphthyl) group, perfluoro(2-naphthyl) group, 1-trifluoromethylphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 4-trifluoromethylphenyl and other aromatic hydrocarbon groups having fluorine atoms;

[0203] Perfluoromethoxy, perfluoroethoxy, perfluoropropoxy, perfluoro(isopropoxy), perfluorobutoxy, perfluoro(isobutoxy), perfluoro(sec-butoxy), perfluoro(tert-butoxy), perfluoropentoxy, perfluorophenoxy, perfluorobenzyloxy, 2,2,2-trifluoroethoxy, (perfluoroethyl)methoxy, (perfluoropropyl)methoxy, (perfluoro(isopropyl))methoxy, (perfluoro(isopropenyl))methoxy, (perfluoro(1-propenyl))methoxy, (perfluoro(2-propenyl))methoxy, (perfluorobutyl)methoxy, (perfluoro(isobutyl))methoxy, (perfluoro(sec-butyl))methoxy, (perfluoro(tert-butyl))methoxy, (perfluoro(2-buteneyl))methoxy, (perfluoro(1,3-butadienyl))methoxy, (perfluoropentyl)methoxy, (perfluoro(isopentyl))methoxy, (perfluoro(3-pentyl))methoxy, (perfluoro(neopentyl))methoxy, (perfluoro(tert-pentyl))methoxy, (perfluoro(1-methyl-1-pentyl))methoxy, (perfluoro(2-methylpentyl))methoxy, (perfluoro(2-pentenyl))methoxy, (perfluorohexyl)methoxy, (perfluoro(ishexyl))methoxy, (perfluoro(5-methyl-1-hexyl))methoxy, (perfluoro(2-ethyl-1-hexyl))methoxy, (perfluoroheptyl)methoxy, (perfluorooctyl)methoxy, (perfluorononyl)methoxy, (perfluorodecyl)methoxy, (perfluoroundecyl)methoxy, (perfluorododecyl)methoxy, (perfluorooctadecyl)methoxy and other substituted oxy groups having fluorine atoms;

[0204] 2,3-bis(trifluoromethyl)phenylmethyl, 2,4-bis(trifluoromethyl)phenylmethyl, 2,5-bis(trifluoromethyl)phenylmethyl, 2,6-bis(trifluoromethyl)phenylmethyl, 3,4-bis(trifluoromethyl)phenylmethyl, 3,5-bis(trifluoromethyl)phenylmethyl, etc.

[0205] R 7 ~R 11 and R 13 is preferably a hydrogen atom.

[0206] R 12 is preferably a hydrogen atom, -SO3M or -CO2M, more preferably a hydrogen atom or -SO3M, and particularly preferably a hydrogen atom.

[0207] In formula (A1-4), Z represents a group represented by the following formula (Z1) (in the following formula, * represents a bonding site).

[0208] [Chemical formula 21]

[0209]

[0210] In formula (Z1), R 1An alkyl group having 1 to 20 carbon atoms, wherein the -CH2- constituting the alkyl group may be substituted by an oxygen atom. Examples of the above alkyl group include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, 2-ethyl-1-butyl, pentyl, isopentyl, 3-pentyl, neopentyl, tert-pentyl, 1-methyl-1-pentyl, 2-methyl-1-pentyl, 3-ethyl-1-pentyl, hexyl, isohexyl, 5-methyl-1-hexyl, 2-ethyl-1-hexyl, heptyl, 3-ethyl-1-heptyl, octyl, nonyl, decyl, undecyl, dodecyl, octadecyl, etc. An alkyl group having 1 to 16 carbon atoms is preferred.

[0211] Examples of the group in which -CH2- constituting these alkyl groups is substituted by an oxygen atom include the groups represented by the above formulas (GL-1) to (GL-8).

[0212] L is a divalent hydrocarbon group or a sulfonyl group having 1 to 20 carbon atoms. When Z is a group represented by the formula (Z1), from the viewpoint of the solubility of the compound (A1-4) in a solvent, R in the formula (Z1) 1 is preferably an alkyl group having 1 to 16 carbon atoms or a group represented by any one of the 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 the formulas (GL-1) to (GL-8), still more preferably an alkyl group having 6 to 10 carbon atoms (e.g., 2-ethyl-1-hexyl, 1-octyl, etc.) or a group represented by any one of the formulas (GL-3) to (GL-8), and particularly preferably 1-octyl.

[0213] In the 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, wherein the -CH2- constituting the hydrocarbon group may be substituted by an oxygen atom, a sulfur atom, -N(R 30 )-, a sulfonyl group, or a carbonyl group, and the hydrogen atom contained in the hydrocarbon group may be substituted by a halogen atom, a cyano group, a nitro group, a carbamoyl group, a sulfamoyl group, -SO3M, -CO2M, a hydroxyl group, a formyl group, or an amino group. R 30 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms. When there are a plurality of R 30 , they may be the same or different. M represents a hydrogen atom or an alkali metal atom. When there are a plurality of M, they may be the same or different.

[0214] Examples of R 2 ~R 6 include the same groups as those of the above R 7 ~R 13 . R30 Groups similar to R can also be cited. 14 The same groups can also be cited.

[0215] L is a divalent hydrocarbon group or sulfonyl group having 1 to 20 carbon atoms. When Z is a group represented by the formula (Z1), from the viewpoint of the solubility of the compound (A1-4) in a solvent, R in the formula (Z1) 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, still more preferably a methyl group, an ethyl group or a 2-propyl group, and particularly preferably a methyl group. The color filter formed from the colored curable resin composition containing the coloring agent (A1-4) containing R as these groups has a tendency to have high brightness. 2 The color filter formed from the colored curable resin composition containing the coloring agent (A1-4) containing R as these groups has a tendency to have high brightness.

[0216] L is a divalent hydrocarbon group or sulfonyl group having 1 to 20 carbon atoms. When Z is a group represented by the formula (Z1), from the viewpoint of the solubility of the compound (A1-4) in a solvent, R in the formula (Z1) 4 is preferably a hydrogen atom, -SO3M, -CO2M or an alkyl group having 1 to 8 carbon atoms (for example, methyl group, ethyl group, 1-propyl group, 2-propyl group, 1-butyl group, tert-butyl group, 1-hexyl group, 2-ethyl-1-hexyl group, 1-octyl group, etc.), more preferably a hydrogen atom, -SO3M, -CO2M or an alkyl group having 1 to 4 carbon atoms, and still more preferably a methyl group.

[0217] L is a divalent hydrocarbon group or sulfonyl group having 1 to 20 carbon atoms. When Z is a group represented by the 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.

[0218] L is a divalent hydrocarbon group or sulfonyl group having 1 to 20 carbon atoms. When Z is a group represented by the formula (Z1), R 3 and R 5 are preferably hydrogen atoms.

[0219] From the viewpoint of light resistance, the coumarin dye is preferably one or both of the compound represented by the formula (A1-3) and the compound represented by the formula (A1-4). From the viewpoint of further improving the light resistance, it is more preferably the compound represented by the formula (A1-4).

[0220] The content rate of the coumarin dye is, for example, 10% by mass or more, preferably 20% by mass or more, more preferably 30% by mass or more, for example, 95% by mass or less, preferably 90% by mass or less, and more preferably 80% by mass or less with respect to the total amount of the coloring agent (A).

[0221] In addition, the content rate of the coumarin dye is, for example, 2% by mass or more, preferably 4% by mass or more, more preferably 6% by mass or more, for example, 60% by mass or less, preferably 50% by mass or less, and more preferably 40% by mass or less, relative to the solid component of the colored curable resin composition.

[0222] The content ratio of the squarylium dye and the coumarin dye / anthraquinone dye is preferably 0.5 or more, more preferably 1 or more, further preferably 1.5 or more, still more preferably 1.7 or more, preferably 10 or less, more preferably 7 or less, and further preferably 5 or less.

[0223] The colored curable resin composition of the present invention may contain a colorant other than an anthraquinone dye, a squarylium dye, and a coumarin dye having a carboxyl group (hereinafter, sometimes referred to as colorant (A2)) as colorant (A). The colorant (A2) may contain one or more than two kinds of colorants.

[0224] The colorant (A2) may be a dye or a pigment. As the dye, known dyes described in the Color Index (published by The Society of Dyers and Colourists) and the Dyeing Manual (Color Dyeing Society) can be cited. In addition, according to the chemical structure, azo dyes, anthraquinone dyes (excluding the compound represented by formula (A1)), triphenylmethane dyes, cyanine dyes, naphthoquinone dyes, quinoneimine dyes, methylene 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, phthalocyanine dyes, etc. can be cited. Among them, an organic solvent-soluble dye is preferred. Two or more of these dyes can be used in combination.

[0225] Specifically, dyes with the following Color Index (C.I.) numbers can be cited.

[0226] C.I. Solvent Yellow 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162;

[0227] C.I. 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;

[0228] C.I. Reactive Yellow 2, 76, 116;

[0229] C.I. 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;

[0230] C.I. Disperse Yellow 51, 54, 76;

[0231] C.I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 99;

[0232] C.I. 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;

[0233] C.I. Reactive Orange 16;

[0234] C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;

[0235] C.I. 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;

[0236] C.I. Acid Red 73, 80, 91, 92, 97, 138, 151, 211, 274, 289;

[0237] C.I. Acid Violet 34, 102;

[0238] C.I. Disperse Violet 26, 27;

[0239] C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;

[0240] C.I. 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;

[0241] C.I. Acid Blue 25, 27, 40, 45, 78, 80, 112;

[0242] C.I. Direct Blue 40;

[0243] C.I. Disperse Blue 1, 14, 56, 60;

[0244] C.I. Solvent Green 1, 3, 5, 28, 29, 32, 33;

[0245] C.I. Acid Green 3, 5, 9, 25, 27, 28, 41;

[0246] C.I. Basic Green 1;

[0247] C.I. Vat Green 1 etc.

[0248] 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) can be cited. Two or more kinds can be combined.

[0249] Specifically, the following can be cited:

[0250] C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214 etc. yellow pigments;

[0251] C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 etc. orange pigments;

[0252] C.I. 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, red pigments such as diketopyrrolopyrrole dibromide;

[0253] C.I. Pigment Green 15, 15:3, 15:4, 15:6, 60 and other blue pigments;

[0254] C.I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other purple pigments;

[0255] C.I. Pigment Green 7, 36, 58, 59 and other green pigments.

[0256] The colorant (A2) can be treated as follows according to needs: rosin treatment, surface treatment using a colorant derivative into which an acidic group or a basic group is introduced, graft treatment of the pigment surface using a polymer compound, etc., micronization treatment using a sulfuric acid micronization method, etc., cleaning treatment using an organic solvent or water for removing impurities, ion impurity removal treatment using an ion exchange method, etc. The particle diameters of the pigments, etc. are preferably each substantially uniform. The colorant (A2) is subjected to a dispersion treatment by adding a dispersant to form a state of being uniformly dispersed in the dispersion liquid.

[0257] As the dispersant, surfactants, etc. can be cited, and it can be any one of cationic, anionic, nonionic and amphoteric surfactants. Specifically, surfactants such as polyester-based, polyamine-based and acrylic-based can be cited. As other dispersants, the resin (B) described later can be used. These dispersants can be used alone or in combination of two or more. As the dispersant, those represented by trade names such as KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF Corporation), Ajispur (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK Chemie GmbH), BYK (registered trademark) (manufactured by BYK Chemie GmbH), etc. can be cited.

[0258] When using a dispersant, the usage amount of the dispersant is preferably 100 parts by mass or less, more preferably 5 parts by mass or more and 50 parts by mass or less with respect to 100 parts by mass of the colorant (A2). If the usage amount of the dispersant is within the above range, there is a tendency to obtain a liquid containing the colorant (A2) in a more uniform dispersion state.

[0259] When the coloring curable resin composition contains a colorant (A2), its content is usually 0.1% by mass or more and 50% by mass or less, preferably 1% by mass or more and 40% by mass or less, more preferably 1% by mass or more and 30% by mass or less in the total amount of solid components.

[0260] <Resin (B)>

[0261] The resin (B) is not particularly limited, preferably an alkali-soluble resin, more preferably a resin having a structural unit derived from at least one (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter sometimes referred to as "(a)"). The resin (B) is further preferably a resin having at least one structural unit selected from the group consisting of the following structural units: a structural unit derived from a monomer (b) having a cyclic ether structure with 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b)"); a structural unit derived from a monomer (c) capable of copolymerizing with (a) (but different from (a) and (b)) (hereinafter sometimes referred to as "(c)"); and a structural unit having an ethylenically unsaturated bond in the side chain.

[0262] Specific examples of (a) include, for example, acrylic acid, methacrylic acid, maleic anhydride, itaconic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, succinic acid mono[2-(meth)acryloyloxyethyl] ester, etc., and acrylic acid, methacrylic acid, and maleic anhydride are preferred.

[0263] It should be noted that in this specification, "(meth)acrylic acid" means at least one selected from the group consisting of acrylic acid and methacrylic acid. Expressions such as "(meth)acryloyl" and "(meth)acrylate" have the same meaning.

[0264] (b) is preferably a monomer having a cyclic ether structure with 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an ethylene oxide ring, an oxetane ring, and a tetrahydrofuran ring) and a (meth)acryloyloxy group.

[0265] Examples of (b) include glycidyl (meth)acrylate, vinylbenzyl glycidyl ether, (meth)acrylic acid-3,4-epoxytricyclo[5.2.1.0 2,6 decyl ester, 3-ethyl-3-(meth)acryloyloxymethyloxetane, tetrahydrofurfuryl (meth)acrylate, etc., and glycidyl (meth)acrylate, (meth)acrylic acid-3,4-epoxytricyclo[5.2.1.0 2,6 decyl ester, 3-ethyl-3-(meth)acryloyloxymethyloxetane are preferred.

[0266] As (c), for example, methyl (meth)acrylate, butyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 decane-8-yl (meth)acrylate, benzyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, styrene, vinyltoluene, etc. are mentioned. Preferred are styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, 2-hydroxyethyl (meth)acrylate, etc.

[0267] The resin having a structural unit with an ethylenically unsaturated bond in the side chain can be produced by adding (b) to the copolymer of (a) and (c), or adding (a) to the copolymer of (b) and (c). The resin can also be a resin obtained by further reacting a carboxylic anhydride with the copolymer of adding (a) to (b) and (c).

[0268] The polystyrene-reduced weight-average molecular weight of resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and still more preferably 5,000 to 30,000.

[0269] The dispersity [weight-average molecular weight (Mw) / number-average molecular weight (Mn)] of resin (B) is preferably 1.1 to 6, more preferably 1.2 to 4.

[0270] The acid value of resin (B) in terms of solid content is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150 mg-KOH / g, and still more preferably 70 to 135 mg-KOH / g. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin (B), and can be obtained by titration with, for example, an aqueous potassium hydroxide solution.

[0271] The content rate of resin (B) relative to the total amount of solid components is preferably 10 to 70 mass%, more preferably 15 to 65 mass%, and still more preferably 20 to 60 mass%.

[0272] <Polymerizable compound (C)>

[0273] The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated from a polymerization initiator (D). For example, compounds having a polymerizable ethylenically unsaturated bond, etc. are mentioned. Preferred are (meth)acrylate compounds.

[0274] 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, dipentaerythritol hexa(meth)acrylate, and the like.

[0275] The weight-average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, more preferably 250 or more and 1,500 or less.

[0276] The content of the polymerizable compound (C) is preferably 10 to 70% by mass, more preferably 15 to 65% by mass, and further preferably 20 to 60% by mass with respect to the total solid content.

[0277] <Polymerization initiator (D)>

[0278] The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light or heat to initiate polymerization, and known polymerization initiators can be used. Examples of the polymerization initiator that generates active radicals include N-benzoyloxy-1-(4-phenylthiophenyl)butane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine, N-benzoyloxy-1-(4-phenylthiophenyl)-3-cyclopentylpropane-1-one-2-imine, 2-methyl-2-morpholino-1-(4-methylthiophenyl)propane-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutane-1-one, 1-hydroxycyclohexyl phenyl ketone, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4,6-trimethylbenzoyl diphenylphosphine oxide, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl benzimidazole, and the like.

[0279] The polymerization initiator is preferably a polymerization initiator containing at least one selected from the group consisting of triazine compounds, acylphosphine oxide compounds, alkylbenzene ketone compounds, O-acyl oxime compounds, and benzimidazole compounds, and more preferably a polymerization initiator containing O-acyl oxime compounds.

[0280] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). If the content of the polymerization initiator (D) is within the above range, there is a tendency to increase the sensitivity and shorten the exposure time, so the productivity of the color filter is improved.

[0281] The content rate of the O-acyl oxime compound is preferably 50% by mass or more, more preferably 80% by mass or more, still more preferably 90% by mass or more, and particularly preferably 95% by mass or more, relative to the total amount of the polymerization initiator (D). When the content rate of the O-acyl oxime compound is within the above range, there is a tendency to be able to produce a color filter that has excellent sensitivity and developability when forming a colored pattern and has high brightness even when the colorant content rate is high.

[0282] The colored curable resin composition of the present invention may contain a polymerization initiator assistant.

[0283] <Polymerization initiator assistant (D1)>

[0284] The polymerization initiator assistant (D1) is a compound or a sensitizer that promotes the polymerization of a polymerizable compound initiated by a polymerization initiator. When the polymerization initiator assistant (D1) is included, it is usually used in combination with the polymerization initiator (D).

[0285] Examples of the polymerization initiator assistant (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.

[0286] When using these polymerization initiator assistants (D1), the content is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the amount of the polymerization initiator assistant (D1) is within the above range, a colored pattern can be formed with higher sensitivity, and there is a tendency to improve the productivity of the color filter.

[0287] The colored curable resin composition of the present invention preferably contains a solvent.

[0288] <Solvent (E)>

[0289] The solvent (E) is not particularly limited, and solvents commonly used in the art can be used. For example, ester solvents (solvents containing -COO- in the molecule but not containing -O-), ether solvents (solvents containing -O- in the molecule but not containing -COO-), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule but not containing -COO-), alcohol solvents (solvents containing OH in the molecule but not containing -O-, -CO-, and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like can be mentioned.

[0290] Examples of the solvent include:

[0291] Ester solvents such as ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, methyl acetoacetate, cyclohexyl acetate, and γ-butyrolactone (solvents containing -COO- but not -O- in the molecule);

[0292] Ether solvents 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 (solvents containing -O- but not -COO- in the molecule);

[0293] Ether ester solvents 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 (solvents containing both -COO- and -O- in the molecule);

[0294] Ketone solvents such as 4-hydroxy-4-methyl-2-pentanone, heptanone, 4-methyl-2-pentanone, and cyclohexanone (solvents containing -CO- but not -COO- in the molecule);

[0295] Alcohol solvents such as butanol, cyclohexanol, and propylene glycol (solvents containing OH but not -O-, -CO-, and -COO- in the molecule), etc.

[0296] Aromatic hydrocarbon solvents such as toluene and xylene can be cited. Amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone can be cited.

[0297] As the solvent, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, cyclohexanone, N-methylpyrrolidone, and ethyl 3-ethoxypropionate are more preferred.

[0298] The solvent is preferably a mixed solvent containing propylene glycol monomethyl ether acetate. As the solvent combined with propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, 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 are preferred, ethyl lactate, dipropylene glycol methyl ether acetate, propylene glycol monomethyl ether, 3-methoxybutyl acetate, 3-methoxy-1-butanol, N-methylpyrrolidone, and ethyl 3-ethoxypropionate are more preferred, and ethyl lactate, 4-hydroxy-4-methyl-2-pentanone, N-methylpyrrolidone, and propylene glycol monomethyl ether are further preferred.

[0299] The content rate of the solvent 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 still more preferably 5% by mass or more and 80% by mass or less, relative to the total amount of the solvent.

[0300] In the case of containing the solvent (E), the content rate of the solvent (E) is preferably 20 to 90% by mass, more preferably 25 to 85% by mass, relative to the total amount of the colored curable resin composition of the present invention. In other words, the total content rate of the solid components of the colored curable resin composition is preferably 10 to 80% by mass, more preferably 15 to 75% by mass. If the content rate of the solvent (E) is within the above range, there is a tendency that the flatness during coating becomes good, and the display characteristics become good because the color density is not insufficient when forming the color filter.

[0301] <Other components>

[0302] The colored curable resin composition of the present invention may contain additives known in the art, such as a leveling agent, a filler, other polymer compounds, an adhesion promoter, an antioxidant, a light stabilizer, a chain transfer agent, etc., as needed.

[0303] <Method for manufacturing the colored curable resin composition>

[0304] The colored curable resin composition of the present invention can be prepared by mixing a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and, as needed, a solvent (E) and other components.

[0305] <Method for manufacturing the color filter>

[0306] As a method for manufacturing a colored pattern from the colored curable resin composition of the present invention, a photolithography method, an inkjet method, a printing method, etc. can be mentioned. Among them, the photolithography method is preferred. In the photolithography method, a colored coating film, which is a cured product of the colored curable resin composition layer, can be formed without using a photomask and / or without developing during exposure. The colored pattern and the colored coating film thus formed are the color filters of the present invention.

[0307] The colored curable resin composition can produce a color filter with excellent light resistance. The color filter is useful as a color filter used in a display device (for example, a liquid crystal display device, an organic EL device, an electronic paper, etc.) and a solid-state imaging element.

[0308] [Examples]

[0309] Hereinafter, examples are given to more specifically illustrate the present invention. In the examples, unless otherwise specified, % and parts representing the content or the amount used are based on mass.

[0310] In the following examples, the structures of the compounds were identified by mass spectrometry (LC: Agilent 1200 series, MASS: Agilent LC / MSD) or NMR (JNM-EX-270; manufactured by JEOL Ltd.).

[0311] [Synthesis Example 1]

[0312] [Chemical Formula 22]

[0313]

[0314] In a flask equipped with a condenser and a stirrer, 66.9 parts of chlorosulfonic acid was added and cooled to 10°C or lower. With stirring, 3.6 parts of C.I. Solvent Blue 104 (Compound (X-1)) was slowly added. Thereafter, the reaction solution was allowed to warm up to room temperature naturally and stirred at the same temperature for 6 hours. The resulting reaction solution was dropped into 108 parts of ice water to form a suspension, and the precipitated crystals were filtered out, washed thoroughly with ion-exchanged water, and dried under reduced pressure at 60°C overnight to obtain 4.9 parts of a crude product of the compound represented by the formula (A-1-IM1). It was purified by silica gel column chromatography (solvent: chloroform) to obtain 3.4 parts of the compound represented by the formula (A-1-IM1).

[0315] [Chemical Formula 23]

[0316]

[0317] In a flask equipped with a condenser 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 lower. With stirring, a solution prepared by dissolving 2.4 parts of the compound represented by the formula (A-1-IM1) in 16.5 parts of chloroform and 2.2 parts of pyridine were successively added dropwise. Thereafter, the reaction solution was allowed to warm up to room temperature naturally and stirred at the same temperature for 5 hours. To the resulting reaction solution, 150 parts of chloroform and 50 parts of 2N hydrochloric acid were added for liquid separation, and the organic layer was washed twice with 50 parts of 2N hydrochloric acid. The resulting organic layer was dried with an excessive amount of sodium sulfate, and the filtered solution was evaporated to obtain 3.4 parts of a crude product of the compound represented by the formula (A-1-IM2). It was purified by silica gel column chromatography (solvent: chloroform) to obtain 2.8 parts of the compound represented by the formula (A-1-IM2).

[0318] [Chemical Formula 24]

[0319]

[0320] Identification of the compound represented by the formula (A-1-IM2)

[0321] (Mass spectrometry) Ionization mode = ESI +: m / z = [M+H] + 929.2

[0322] Exact Mass: 928.3

[0323] In a flask equipped with a condenser and a stirring device, 2.5 parts of the compound represented by the formula (A-1-IM2), 35 parts of N-methylpyrrolidone, and 17 parts of an 8% aqueous sodium hydroxide solution were added, and the mixture was stirred at 50 °C for 5 hours. The resulting reaction solution was added to 175 parts of 2N hydrochloric acid to form a suspension, and the precipitated crystals were filtered out, washed thoroughly with ion-exchanged water, and dried under reduced pressure at 60 °C overnight to obtain 2.1 parts of the compound represented by the formula (A-1) (hereinafter, sometimes referred to as "dye (A-1)").

[0324] [Chemical formula 25]

[0325]

[0326] Identification of the compound represented by the formula (A-1)

[0327] (Mass analysis) Ionization mode = ESI + : m / z = [M+H] + 901.2

[0328] Exact mass: 900.3

[0329] [Synthesis Example 2]

[0330] 10.0 parts of 2,4-dimethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.), 17.0 parts of 2-ethyl bromohexane (manufactured by Tokyo Chemical Industry Co., Ltd.), and 44.0 parts of tetrabutylammonium bromide (manufactured by Fujifilm Wako Pure Chemical Corporation) were mixed. The resulting mixture was stirred at 90 °C for 8 hours. After the reaction was completed, 50 parts of 10% aqueous sodium bicarbonate was added, then 100 parts of ethyl acetate was added, and the aqueous layer was discarded. After repeating the operations of washing with water and 10% hydrochloric acid twice, the solvent was distilled off. The resulting oil was dried under reduced pressure at 60 °C for 24 hours to obtain 9.3 parts of the compound represented by the formula (d-1).

[0331] [Chemical formula 26]

[0332]

[0333] Of the compound represented by the formula (d-1) 1H-NMR (270 MHz, δ value (ppm, TMS reference), 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)

[0334] 3.0 parts of the compound represented by the 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 tert-butoxysodium (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.055 parts of tri-tert-butylphosphine (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 column 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 the formula (d-2).

[0335] [Chemistry 27]

[0336]

[0337] The compound represented by formula (d-2) 1 H-NMR (270 MHz, δ value (ppm, TMS reference), DMSO-d6) 0.85 (m, 6H), 1.23-1.42 (br, 8H), 1.55 (br, 1H), 1.94 (s, 3H), 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)

[0338] 4.4 parts of the compound represented by the 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 resulting mixture was stirred at 125°C for 3 hours while removing the generated water 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 solution, and the precipitated solid was collected by filtration. The solid collected by filtration 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)".

[0339] [Chemical formula 28]

[0340]

[0341] Of the compound represented by formula (AII-8) 1 H-NMR (270 MHz, 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)

[0342] [Synthesis Example 3]

[0343] In Synthesis Example 2, the compound represented by formula (d-3) was used instead of the compound represented by formula (d-1), and the compound represented by formula (d-4) was used instead of the compound represented by formula (d-2). Otherwise, the procedure was carried out in the same manner as in Synthesis Example 2 to obtain the following compound represented by formula (AII-X).

[0344] [Chemical formula 29]

[0345]

[0346] [Chemical formula 30]

[0347]

[0348] [Chemical formula 31]

[0349]

[0350] [Synthesis Example 4]

[0351] Based on Examples 1 and 2 of International Publication No. 2014 / 208767, the following compound represented by formula (AII-Y) was prepared.

[0352] [Chemical formula 32]

[0353]

[0354] [Synthesis Example 5]

[0355] In a flask equipped with a reflux condenser, a dropping funnel, and a stirrer, an appropriate amount of nitrogen was introduced to displace the atmosphere with nitrogen. 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were added, and the mixture was heated to 85 °C while stirring. Then, a mixed solution of 38 parts of acrylic acid, 25 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 2,6 decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 decane-9-yl acrylate (containing a molar ratio of 1:1), 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. On the other hand, a solution prepared by dissolving 5 parts of 2,2-azobisisobutyronitrile in 88 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the addition was completed, the mixture was maintained at 85 °C for 4 hours and then cooled to room temperature to obtain a copolymer (resin B-1) solution having a viscosity of 23 mPas measured by a B-type viscometer (23 °C) and a solid content of 25.6%. The weight-average molecular weight Mw of the resulting copolymer was 8.0×10 3 , the dispersity was 2.1, and the acid value in terms of solid content was 109 mg-KOH / g. Resin B-1 has the following structural units.

[0356] [Chemical formula 33]

[0357]

[0358] For the measurement of the weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the above resin, the GPC method was used under the following conditions.

[0359] Apparatus: K2479 (manufactured by Shimadzu Corporation)

[0360] Column: SHIMADZU Shim-pack GPC-80M

[0361] Column temperature: 40 °C

[0362] Solvent: THF (tetrahydrofuran)

[0363] Concentration of the test solution: 25 mg / mL (solvent: THF)

[0364] Flow rate: 1.0 mL / min

[0365] Detector: RI

[0366] Standard substance for calibration: TSK standard polystyrene (STANDARD POLYSTYRENE) F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)

[0367] The ratio of the polystyrene-equivalent weight average molecular weight and the number average molecular weight obtained above is defined as the dispersion degree (Mw / Mn).

[0368] Example 1

[0369] <Preparation of Colored Curable Resin Composition>

[0370] (A) Colorant: Dye (AII-8) 10 parts

[0371] (A) Colorant: Dye (A-1) 5 parts

[0372] (B) Resin: Resin (B-1) (solid content conversion) 50 parts

[0373] (C) Polymerizable compound: dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts

[0374] (D) Polymerization initiator: 7 parts of N-benzoyloxy-1-(4-phenylthiophenyl)octan-1-one-2-imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF)

[0375] (F) Leveling agent: polyether modified silicone oil (Toray Silicone SH8400; manufactured by Dow Corning Toray Corporation)

[0376] 0.1 part

[0377] (E) Solvent: 596 parts of propylene glycol monomethyl ether acetate

[0378] (E) Solvent: 95 parts of N-methylpyrrolidone

[0379] The mixture is mixed to obtain a colored curable resin composition.

[0380] Comparative Example 1

[0381] <Preparation of Colored Curable Resin Composition>

[0382] (A) Colorant: Dye (AII-8) 9 parts

[0383] (B) Resin: Resin (B-1) (solid content conversion) 50 parts

[0384] (C) Polymerizable compound: dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts

[0385] (D) Polymerization initiator: 7 parts of N-benzoyloxy-1-(4-phenylthiophenyl)octan-1-one-2-imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF)

[0386] (F) Leveling agent: Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.)

[0387] 0.1 part

[0388] (E) Solvent: Propylene glycol monomethyl ether acetate 659 parts

[0389] They are mixed to obtain a colored curable resin composition.

[0390] Example 2

[0391] <Preparation of Colored Curable Resin Composition>

[0392] (A) Colorant: C.I. Disperse Yellow 82 (coumarin dye) 10 parts

[0393] (A) Colorant: Dye (A-1) 5 parts

[0394] (B) Resin: Resin (B-1) (in terms of solid content) 50 parts

[0395] (C) Polymerizable compound: Dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts

[0396] (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF) 7 parts

[0397] (F) Leveling agent: Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.)

[0398] 0.1 part

[0399] (E) Solvent: Propylene glycol monomethyl ether acetate 145 parts

[0400] (E) Solvent: N-methylpyrrolidone 546 parts

[0401] They are mixed to obtain a colored curable resin composition.

[0402] Comparative Example 2

[0403] <Preparation of Colored Curable Resin Composition>

[0404] (A) Colorant: C.I. Disperse Yellow 82 9 parts

[0405] (B) Resin: Resin (B-1) (in terms of solid content) 50 parts

[0406] (C) Polymerizable compound: Dipentaerythritol hexaacrylate (KAYARAD® DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts

[0407] (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine (IRGACURE® OXE 01; manufactured by BASF) 7 parts

[0408] (F) Levelling agent: Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.)

[0409] 0.1 part

[0410] (E) Solvent: Propylene glycol monomethyl ether acetate 145 parts

[0411] (E) Solvent: N-methylpyrrolidone 515 parts

[0412] They are mixed to obtain a colored curable resin composition.

[0413] Example 3

[0414] <Preparation of colored curable resin composition>

[0415] The following components are mixed: (A) Colorant: Dye (AII-8) 9.5 parts

[0416] (A) Colorant: Dye (A-1) 1.6 parts

[0417] (B) Resin: Resin (B-1) (in terms of solid content) 50 parts

[0418] (C) Polymerizable compound: Dipentaerythritol hexaacrylate (KAYARAD® DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts

[0419] (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine (IRGACURE® OXE 01; manufactured by BASF) 7 parts

[0420] (F) Levelling agent: Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.)

[0421] 0.1 part

[0422] (E) Solvent: Propylene glycol monomethyl ether acetate 639 parts

[0423] (E) Solvent: N-methylpyrrolidone 30 parts

[0424] Mix to obtain a colored curable resin composition.

[0425] Example 4

[0426] <Preparation of Colored Curable Resin Composition>

[0427] Mix (A) colorant: 9.4 parts of dye (AII-8)

[0428] (A) colorant: 1 part of dye (A-1)

[0429] (B) resin: 50 parts of resin (B-1) (in terms of solid content)

[0430] (C) polymerizable compound: 50 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.)

[0431] (D) polymerization initiator: 7 parts of N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF)

[0432] (F) leveling agent: 0.1 part of polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.)

[0433] (E) solvent: 646 parts of propylene glycol monomethyl ether acetate

[0434] (E) solvent: 20 parts of N-methylpyrrolidone

[0435] Mix to obtain a colored curable resin composition.

[0436] Example 5

[0437] <Preparation of Colored Curable Resin Composition>

[0438] Mix (A) colorant: 9.5 parts of C.I. Disperse Yellow 82

[0439] (A) colorant: 1.6 parts of dye (A-1)

[0440] (B) resin: 50 parts of resin (B-1) (in terms of solid content)

[0441] (C) polymerizable compound: 50 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.)

[0442] (D) polymerization initiator: 7 parts of N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF)

[0443] (F) Leveling agent: Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.)

[0444] 0.1 part

[0445] (E) Solvent: Propylene glycol monomethyl ether acetate 145 parts

[0446] (E) Solvent: N-Methylpyrrolidone 525 parts

[0447] Mix to obtain a colored curable resin composition.

[0448] Example 6

[0449] <Preparation of Colored Curable Resin Composition>

[0450] Mix (A) Colorant: C.I. Disperse Yellow 82 9.4 parts

[0451] (A) Colorant: Dye (A-1) 1 part

[0452] (B) Resin: Resin (B-1) (in terms of solid content) 50 parts

[0453] (C) Polymerizable compound: Dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts

[0454] (D) Polymerization initiator: N-Benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF) 7 parts

[0455] (F) Leveling agent: Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.)

[0456] 0.1 part

[0457] (E) Solvent: Propylene glycol monomethyl ether acetate 145 parts

[0458] (E) Solvent: N-Methylpyrrolidone 521 parts Mix to obtain a colored curable resin composition.

[0459] Example 7

[0460] <Preparation of Colored Curable Resin Composition>

[0461] Mix (A) Colorant: Dye (AII-8) 4.9 parts

[0462] (A) Colorant: C.I. Disperse Yellow 82 4.9 parts

[0463] (A) Colorant: Dye (A-1) 4.9 parts

[0464] (B) Resin: Resin (B-1) (in terms of solid content) 50 parts

[0465] (C) Polymerizable compound: Dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts

[0466] (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF) 7 parts

[0467] (F) Levelling agent: Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.)

[0468] 0.1 part

[0469] (E) Solvent: Propylene glycol monomethyl ether acetate 237 parts

[0470] (E) Solvent: N-methylpyrrolidone 452 parts

[0471] These are mixed to obtain a colored curable resin composition.

[0472] Example 8

[0473] <Preparation of Colored Curable Resin Composition>

[0474] (A) Colorant: Dye (AII-X) 9.8 parts

[0475] (A) Colorant: Dye (A-1) 5 parts

[0476] (B) Resin: Resin (B-1) (in terms of solid content) 50 parts

[0477] (C) Polymerizable compound: Dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts

[0478] (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF) 7 parts

[0479] (F) Levelling agent: Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.)

[0480] 0.1 part

[0481] (E) Solvent: 145 parts of propylene glycol monomethyl ether acetate

[0482] (E) Solvent: 546 parts of N-methylpyrrolidone

[0483] They are mixed to obtain a colored curable resin composition.

[0484] Example 9

[0485] <Preparation of Colored Curable Resin Composition>

[0486] (A) Colorant: 9.8 parts of dye (AII-Y)

[0487] (A) Colorant: 5 parts of dye (A-1)

[0488] (B) Resin: 50 parts of resin (B-1) (in terms of solid content)

[0489] (C) Polymerizable compound: 50 parts of dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.)

[0490] (D) Polymerization initiator: 7 parts of N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF)

[0491] (F) Levelling agent: Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.)

[0492] 0.1 part

[0493] (E) Solvent: 145 parts of propylene glycol monomethyl ether acetate

[0494] (E) Solvent: 546 parts of N-methylpyrrolidone

[0495] They are mixed to obtain a colored curable resin composition.

[0496] Comparative Example 3

[0497] <Preparation of Colored Curable Resin Composition>

[0498] (A) Colorant: 9.3 parts of dye (AII-Y)

[0499] (B) Resin: 50 parts of resin (B-1) (in terms of solid content)

[0500] (C) Polymerizable compound: Dipentaerythritol hexaacrylate (KAYARAD® DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts

[0501] (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylthiophenyl)octane-1-one-2-imine (IRGACURE® OXE 01; manufactured by BASF) 7 parts

[0502] (F) Leveling agent: Polyether-modified silicone oil (Toray Silicone SH8400; manufactured by Toray Dow Corning Co., Ltd.)

[0503] 0.1 part

[0504] (E) Solvent: Propylene glycol monomethyl ether acetate 145 parts

[0505] (E) Solvent: N-methylpyrrolidone 515 parts

[0506] These are mixed to obtain a colored curable resin composition.

[0507] <Chromaticity evaluation>

[0508] For the obtained colored pattern, a colorimeter (OSP-SP-200; manufactured by Olympus Corporation) is used to measure the spectrum, and the xy chromaticity coordinates (x, y) and the stimulus value Y in the CIE XYZ colorimetric system are measured using the characteristic function of the C light source.

[0509] <Lightfastness evaluation>

[0510] An ultraviolet cut-off filter (Colored Optical Glass L38; manufactured by Hoya; cuts off light of 380 nm or less) is placed on the obtained colored pattern, and xenon light is irradiated for 48 hours using a lightfastness tester (SUNTEST GPS+; manufactured by Toyo Seiki Seisaku-sho, Ltd.).

[0511] The xy chromaticity coordinates (x, y) and Y are measured before and after irradiation, and the color difference ΔEAb* is calculated according to the measured values using the method described in JIS Z 8730:2009 (7. Method for calculating color difference). The results are shown in Table 4. The smaller ΔEAb* is, the smaller the color change means.

[0512] [Table 4]

[0513] ΔEab* Example 1 19 Comparative Example 1 44 Example 2 11 Comparative Example 2 51 Example 3 9 Example 4 12 Example 5 21 Example 6 26 Example 7 7 Example 8 12 Example 9 5 Comparative Example 3 44

[0514] With the colored curable resin composition according to the example, it can be confirmed that the obtained color filter exhibits excellent lightfastness.

Claims

1. A colored curable resin composition, characterized in that, Containing a colorant, a resin, a polymerizable compound, and a polymerization initiator, The colorant includes at least one selected from the group consisting of squarylium dyes and coumarin dyes, and an anthraquinone dye having a carboxyl group, The anthraquinone dye having a carboxyl group is a compound represented by formula (A1), The squarylium dye is a compound represented by formula (A1-2), The coumarin dye is either a compound represented by formula (A1-3) or a compound represented by formula (A1-4), In formula (A1), A 1a and A 2a each independently represents a phenylene group which may have substituents, 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 may be replaced by -O-, -SO2- or -NR 11a -, provided that adjacent -CH2- is not simultaneously replaced by the same group, R 1a ~R 6a each independently represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 8 carbon atoms, and R 11a represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms. In formula (A1-2), R 1 to R 4 each independently represents a hydrogen atom, a halogen atom, a hydroxyl group, or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, wherein the hydrogen atoms 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-, provided that adjacent -CH2- groups are not simultaneously substituted with the same group, and there is no case where the terminal -CH2- group is substituted. R 5 ~R 8 each independently represents a hydrogen atom or a hydroxyl group R 9 and R 10 each independently represents a phenyl group which may be substituted by 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, wherein the hydrogen atoms 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 substituted with -O- or -S-, provided that adjacent -CH2- is not simultaneously substituted with the same group, and further, there is no case where the terminal -CH2- is substituted. In formula (A1-3), R 71 represents a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have substituents, 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 from 0 to 3. When s is an integer of 2 or more, multiple Rs 72 may be the same or different, t represents an integer from 0 to 4. When t is an integer of 2 or more, multiple Rs 73 can be the same or different, 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-), X represents an oxygen atom or a sulfur atom, R 7 to 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 may be replaced by 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 (-CONH2), a sulfamoyl group (-SO2NH2), -SO3M, -CO2M, a hydroxyl 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. When there are multiple Rs, 14 they may be the same or different. M represents a hydrogen atom or an alkali metal atom. When there are multiple M's, they may be the same or different, Z is formula (Z1), In formula (Z1), R 1 represents an alkyl group having 1 to 20 carbon atoms, and -CH2- constituting the alkyl group may be substituted by an oxygen atom. 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 may be replaced by 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 hydroxyl group, a formyl group or an amino group, R 30 represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms. When there are a plurality of Rs, 30 they may be the same or different. M represents a hydrogen atom or an alkali metal atom. When there are multiple M's, they may be the same or different.

2. A color filter formed from the colorant-curable resin composition according to claim 1.

3. A display device comprising the color filter according to claim 2.

Images