Compound

Abstract

To provide a compound required for the formation of a color filter that shows excellent contrast.SOLUTION: For example, the following compound is illustrated.SELECTED DRAWING: None

Description

[Technical field]

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

[0002] Color filters used in displays such as liquid crystal displays, electroluminescent displays, and plasma displays, and solid-state imaging devices such as CCD and CMOS sensors, are manufactured from colored resin compositions. As a colorant contained in such colored resin compositions, a xanthene compound represented by the following formula is known (Patent Document 1).

[0003] [ka] [Prior art documents] [Patent documents]

[0004] [Patent Document 1] JP 2017-226814 A Summary of the Invention [Problem to be solved by the invention]

[0005] However, color filters formed from the above-mentioned conventional colored resin compositions do not provide a fully satisfactory contrast. [Means for solving the problem]

[0006] The gist of the present invention is as follows. [1] A compound represented by formula (I-1), formula (I-2), or formula (I-3). [ka] [In the formula (I-1), formula (I-2), or formula (I-3), L 1 is a divalent linking group, L 2 is a trivalent linking group, L 3 represents a tetravalent linking group. b 11 ~b 19 each independently represents formula (i), a represents L 1 , L 2 , or L 3 Represents a bond with . In formula (i), R 1 , R 2 and R 3 each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a hydrogen atom, and -CH2- contained in the hydrocarbon group is -O-, -CO- or -NR 11 It may be replaced with -. R 1 , R 2 and R 3 At least one of these represents a hydrocarbon group having a carboxy group as a substituent. R 11 represents a hydrocarbon group having 1 to 8 carbon atoms. R 4 ~R 9 each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms. R 10 is a hydrocarbon group with 1 to 10 carbon atoms, -OH, -SO3 - Z + , -CO2 - Z + , -CO2R 12 , -SO3R 12 or -SO2NR 13 R 14 Represents. Z + is a hydron, an alkali metal cation or N + (R 15 )4. R 12 represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms. R 13 and R 14each independently represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group is -O-, -CO- or -NR 11 It may be replaced with -. R 13 and R 14 may be bonded to each other to form a 3- to 10-membered ring containing a nitrogen atom. R 15 represents a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms; R 15 When multiple are present, they may be the same or different. m represents an integer of 0 to 4, and when m is 2 or more, a plurality of R 10 may be the same or different.] [2] A colored resin composition comprising the compound according to [1] and a resin. [3] The colored resin composition according to [2], further comprising a polymerizable compound and a polymerization initiator. [4] A color filter formed from the colored resin composition according to [2] or [3]. [5] A display device comprising the color filter according to [4]. Effect of the Invention

[0007] According to the compound of the present invention and a colored resin composition containing the compound, a color filter having excellent contrast can be formed. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0008] <Compound represented by formula (I-1), formula (I-2), or formula (I-3) (Colorant (A))> The compound of the present invention is a compound represented by formula (I-1), (I-2), or (I-3) (hereinafter, may be referred to as compound (I)). The compound represented by formula (I-1), (I-2), or (I-3) forms a salt within one molecule.

[0009] [ka] [In the formula (I-1), formula (I-2), or formula (I-3), L 1 is a divalent linking group, L 2 is a trivalent linking group, L 3 represents a tetravalent linking group. b 11 ~b 19 each independently represents formula (i), a represents L 1 , L 2 , or L 3 Represents a bond with . In formula (i), R 1 , R 2 and R 3 each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a hydrogen atom, and -CH2- contained in the hydrocarbon group is -O-, -CO- or -NR 11 It may be replaced with -. R 1 , R 2 and R 3 At least one of these represents a hydrocarbon group having a carboxy group as a substituent. R 11 represents a hydrocarbon group having 1 to 8 carbon atoms. R 4 ~R 9 each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms. R 10 is a hydrocarbon group with 1 to 10 carbon atoms, -OH, -SO3 - Z + , -CO2 - Z + , -CO2R 12 , -SO3R 12 or -SO2NR 13 R 14 Represents. Z is a hydron, an alkali metal cation or N + (R 15 )4. R 12 represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms. R 13 and R 14each independently represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group is -O-, -CO-, or -NR 11 It may be replaced with -. R 13 and R 14 may be bonded to each other to form a 3- to 10-membered ring containing a nitrogen atom. R 15 represents a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms; R 15 When multiple are present, they may be the same or different. m represents an integer of 0 to 4, and when m is 2 or more, a plurality of R 10 may be the same or different.]

[0010] L 1 is a divalent linking group, L 2 is a trivalent linking group, L 3 represents a tetravalent linking group. Each of the divalent to tetravalent linking groups is preferably a divalent to tetravalent organic group, more preferably a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and further preferably a hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, and -CH2- contained in these hydrocarbon groups is -O-, -CO-, -SO2-, or -NR 11 -CH2- in the hydrocarbon group may be replaced by -O-, -CO-, -SO2-, or -NR 11 When replaced by -, the number of carbon atoms is the same as the number of carbon atoms before the replacement.

[0011] The divalent linking group is preferably a divalent saturated or unsaturated hydrocarbon group, more preferably a linear or branched alkanediyl group, a monocyclic or polycyclic divalent alicyclic saturated hydrocarbon group, or a divalent aromatic hydrocarbon group. The divalent linking group may be a group formed by combining two or more of these groups.

[0012] Specific examples of such straight-chain alkanediyl groups include methylene, ethylene, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, hexane-1,6-diyl, heptane-1,7-diyl, octane-1,8-diyl, nonane-1,9-diyl, decane-1,10-diyl, undecane-1,11-diyl, dodecane-1,12-diyl, tridecane-1,13-diyl, tetradecane-1,14-diyl, pentadecane-1,15-diyl, hexadecane-1,16-diyl, and heptadecane-1,17-diyl groups; branched alkanediyl groups such as ethane-1,1-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-2,2-diyl, pentane-2,4-diyl, 2-methylpropane-1,3-diyl, 2-methylpropane-1,2-diyl, pentane-1,4-diyl, and 2-methylbutane-1,4-diyl; monocyclic divalent alicyclic saturated hydrocarbon groups such as cycloalkanediyl groups, such as cyclobutane-1,3-diyl, cyclopentane-1,3-diyl, cyclohexane-1,4-diyl, and cyclooctane-1,5-diyl; polycyclic divalent alicyclic saturated hydrocarbon groups, such as norbornane-1,4-diyl group, norbornane-2,5-diyl group, adamantane-1,5-diyl group, and adamantane-2,6-diyl group; Examples of the divalent aromatic hydrocarbon groups include a 1,2-phenylene group, a 1,3-phenylene group, and a 1,4-phenylene group. Examples of groups formed by combining two or more types include divalent groups formed by combining an alkanediyl group with an alicyclic saturated hydrocarbon group (for example, -alkanediyl group-divalent alicyclic hydrocarbon group-), and divalent groups formed by combining an alkanediyl group with an aromatic hydrocarbon group (for example, -alkanediyl group-divalent aromatic hydrocarbon group-alkanediyl group-).

[0013] The -CH2- contained in the hydrocarbon group is -O-, -CO-, -SO2-, or -NR 11 Examples of hydrocarbon groups substituted with - include the following (* represents a bond): [ka]

[0014] Among these, the divalent linking group is preferably a linear or branched alkanediyl group, and particularly preferably a linear alkanediyl group.

[0015] Examples of the trivalent linking group include a group in which one hydrogen atom has been removed from the divalent linking group, and a group in which the divalent linking group is further bonded to the divalent linking group. Examples of the trivalent linking group include >C(R 100 )-[R 100 is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and the hydrocarbon group is R 1 , R 2 and R 3 The same applies below. ], >C(R 100 )-C(R 100 )2-, >C=C(R 100 )-, a group in which one hydrogen atom has been removed from a divalent alkanediyl group, a group in which one hydrogen atom has been removed from a divalent aromatic hydrocarbon group (preferably a phenylene group), and a group in which one bond of an alkanediyl group is bonded to each bond of the above groups. Other trivalent linking groups include the following (* represents a bond):

[0016] [ka]

[0017] Examples of the tetravalent linking group include a group in which two hydrogen atoms have been removed from the divalent linking group, and a group in which two of the divalent linking groups are further bonded to the divalent linking group. Examples of the tetravalent linking group include >C<, >C(R 200 )-C(R 200 )<[R 200 is a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms, and the hydrocarbon group is R 1 , R 2 and R 3The examples are the same as the hydrocarbon group represented by the formula: ], >C=C<, a group in which two hydrogen atoms have been removed from a divalent alkanediyl group, a group in which two hydrogen atoms have been removed from a divalent aromatic hydrocarbon group (preferably a phenylene group), and a group in which one bond of an alkanediyl group is bonded to each bond of the above groups. Other tetravalent linking groups include the following (* represents a bond):

[0018] [ka]

[0019] The divalent to tetravalent hydrocarbon group may have a substituent, and examples of the substituent include a halogen atom, a hydroxy group, a cyano group, and an alkoxy group having 1 to 12 carbon atoms.

[0020] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0021] Examples of the alkoxy group having 1 to 12 carbon atoms include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, an octyloxy group, a 2-ethylhexyloxy group, a nonyloxy group, a decyloxy group, an undecyloxy group, and a dodecyloxy group.

[0022] b 11 ~b 19 each independently represents formula (i), a represents L 1 , L 2 , or L 3 It represents a bond with L. 1 , L 2 , or L 3 In the above, a may be the same or different, and is preferably the same.

[0023] R 1 , R 2 and R 3each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a hydrogen atom, and -CH2- contained in the hydrocarbon group is -O-, -CO- or -NR 11 - may be replaced, provided that adjacent -CH2- are not simultaneously replaced with the same group, and the terminal -CH2- is not replaced.

[0024] R 1 ~R 3 Examples of the monovalent hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) include a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, a monovalent unsaturated aliphatic hydrocarbon group having 1 to 20 carbon atoms, and a monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms.

[0025] Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, hexadecyl, and icosyl groups; branched alkyl groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl groups; and alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms such as cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, and tricyclodecyl groups. The number of carbon atoms in the saturated hydrocarbon group is preferably 1 to 18, more preferably 1 to 15, and even more preferably 2 to 10.

[0026] Examples of the monovalent unsaturated aliphatic hydrocarbon group having 1 to 20 carbon atoms include alkenyl groups such as vinyl group, allyl group, butenyl group, pentenyl group, hexenyl group, heptenyl group, octenyl group, nonenyl group, decenyl group, undecenyl group, dodecenyl group, hexadecenyl group, octadecenyl group, and icosenyl group; alkynyl groups such as ethynyl group, propynyl group, hexynyl group, decynyl group, and icosenyl group; cycloalkenyl groups such as cyclopentenyl group, cyclohexenyl group, and cycloheptenyl group; etc. The number of carbon atoms in the unsaturated aliphatic hydrocarbon group is preferably 2 to 18, more preferably 2 to 15, and even more preferably 2 to 10.

[0027] Examples of the monovalent aromatic hydrocarbon group having 6 to 20 carbon atoms include a phenyl group, a xylyl group, a trimethylphenyl group, a dipropylphenyl group, a di(2,2-dimethylpropyl)phenyl group, a naphthyl group, a benzyl group, a phenylethyl group, a phenylbutyl group, etc. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 15, and further preferably 6 to 12.

[0028] R 1 ~R 3 The substituents that the monovalent hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) may have include halogen atoms, -OH, -OR b , -SO3 - Y + , -CO2R b , -SR b , -SO2R b , or -SO3R b The above-mentioned R b represents a saturated hydrocarbon group having 1 to 20 carbon atoms. + is H + , Na + , K + , or N + (R g )4, and the four R g may be the same or different. g represents a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms.

[0029] R b The saturated hydrocarbon group having 1 to 20 carbon atoms represented by the above-mentioned R 1 ~R 3 Examples of the hydrocarbon group having 1 to 20 carbon atoms include the groups represented by the following formula: R g The hydrocarbon group having 1 to 8 carbon atoms represented by the above-mentioned R 1 ~R 3 Among the hydrocarbon groups having 1 to 20 carbon atoms represented by the following formula, those having 1 to 8 carbon atoms are exemplified.

[0030] N + (R g) 4 includes tetramethylammonium, tetraethylammonium, tetrapropylammonium, tetrabutylammonium, and the like.

[0031] -OR b Examples of the alkyloxy group include alkyloxy groups such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group, and an icosyloxy group.

[0032] -CO2R b Examples of the alkyloxycarbonyl group include alkyloxycarbonyl groups such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a hexyloxycarbonyl group, and an icosyloxycarbonyl group.

[0033] -SR b Examples of the alkylsulfanyl group include alkylsulfanyl groups such as methylsulfanyl group, ethylsulfanyl group, butylsulfanyl group, hexylsulfanyl group, decylsulfanyl group and icosylsulfanyl group.

[0034] -SO2R b Examples of the sulfonyl group include alkylsulfonyl groups such as a methylsulfonyl group, an ethylsulfonyl group, a butylsulfonyl group, a hexylsulfonyl group, a decylsulfonyl group, and an icosylsulfonyl group.

[0035] -SO3R b Examples of the sulfonyl group include alkyloxysulfonyl groups such as a methoxysulfonyl group, an ethoxysulfonyl group, a propoxysulfonyl group, a tert-butoxysulfonyl group, a hexyloxysulfonyl group, and an icosyloxysulfonyl group.

[0036] R 11 represents a hydrocarbon group having 1 to 8 carbon atoms. R 11 The hydrocarbon group having 1 to 8 carbon atoms represented by the above-mentioned R1 ~R 3 Among the groups represented by the following formula (1) and having 1 to 20 carbon atoms, those having 1 to 8 carbon atoms are exemplified.

[0037] R 1 , R 2 and R 3 At least one of these represents a hydrocarbon group having a carboxy group as a substituent.

[0038] That is, the compound represented by formula (I-1), formula (I-2), or formula (I-3) preferably satisfies at least one of the requirements (i) to (vi). (i)R 2 is a saturated hydrocarbon group having 1 to 20 carbon atoms and a carboxy group, and R 1 and R 3 At least one of these is an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent, and one molecule contains one carboxy group. (ii)R 1 and R 3 is an aromatic hydrocarbon group having 6 to 10 carbon atoms and a carboxy group. 1 is an aromatic hydrocarbon group having 6 to 10 carbon atoms and a carboxy group, and R 3 is a saturated hydrocarbon group having 1 to 20 carbon atoms and a carboxy group. (iv) R 1 is a saturated hydrocarbon group having 3 to 20 carbon atoms and a carboxy group, and R 2 is a saturated hydrocarbon group having 1 to 20 carbon atoms and a carboxy group. (v)R 1 is a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R 2 is an aromatic hydrocarbon group having 6 to 10 carbon atoms and a carboxy group. (vi)R 1 and R 2 is a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R 3 is an aromatic hydrocarbon group having 6 to 10 carbon atoms and a carboxy group.

[0039] In requirement (i), R 2 is a saturated hydrocarbon group having 1 to 20 carbon atoms (preferably a saturated hydrocarbon group having 1 to 10 carbon atoms) having a carboxy group as a substituent, and R 1 and R 3 At least one of R is preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent. 2 is a saturated hydrocarbon group having 1 to 20 carbon atoms (preferably a saturated hydrocarbon group having 1 to 10 carbon atoms) having a carboxy group as a substituent, and R 1 and R 3 is more preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent.

[0040] In requirement (ii) or (iii), R 2 is preferably a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and more preferably a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

[0041] In requirement (iv), R 3 is preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent. 2 is preferably a saturated hydrocarbon group having 3 to 20 carbon atoms and having a carboxy group as a substituent, and R 1 and R 2 is more preferably a saturated hydrocarbon group having 3 to 10 carbon atoms and having a carboxy group as a substituent.

[0042] In requirement (v), R 1 is a saturated hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, and R 2 is preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms and having a carboxy group as a substituent.

[0043] R 4 ~R 9 each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms. R 4 ~R 9 The alkyl group having 1 to 6 carbon atoms represented by the above-mentioned R 1 ~R 3 Among the groups represented by the following formula (1) and having 1 to 20 carbon atoms, those having 1 to 6 carbon atoms are preferred. Examples of the halogen atom include a chlorine atom, a fluorine atom, a bromine atom, and an iodine atom.

[0044] R 10 is a hydrocarbon group with 1 to 10 carbon atoms, -OH, -SO3 - Z + , -CO2 - Z + , -CO2R 12 , -SO3R 12 or -SO2NR 13 R 14 Represents. Z + is a hydron, an alkali metal cation (e.g. Na + , K + ) or N + (R 15 )4.

[0045] R 12 represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms. R 12 The saturated hydrocarbon group having 1 to 20 carbon atoms represented by the above-mentioned R 1 ~R 3 Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms include the groups represented by the following formula:

[0046] -CO2R 12 As mentioned above, -CO2R b Examples of the groups include the same groups as those explained in the above. -SO3R 12 As mentioned above, -SO3R b Examples of the groups include the same groups as those explained in the above.

[0047] R 13 and R 14each independently represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group is -O-, -CO-, or -NR 11 It may be replaced with -. R 13 and R 14 may be bonded to each other to form a 3- to 10-membered ring containing a nitrogen atom.

[0048] R 13 and R 14 The hydrocarbon group having 1 to 20 carbon atoms represented by the above-mentioned R 1 ~R 3 Examples of the monovalent hydrocarbon group having 1 to 20 carbon atoms include the groups represented by the following formula:

[0049] -SO2NR 13 R 14 Examples of the alkyl group include a sulfamoyl group; N-Methylsulfamoyl group, N-Ethylsulfamoyl group, N-Propylsulfamoyl group, N-Isopropylsulfamoyl group, N-Butylsulfamoyl group, N-Isobutylsulfamoyl group, N-Sec-Butylsulfamoyl group, N-Tert-Butylsulfamoyl group, N-Pentylsulfamoyl group, N-(1-Ethylpropyl)sulfamoyl group, N-(1,1-Dimethylpropyl)sulfamoyl group, N-(1,2-Dimethylpropyl)sulfamoyl group, N-(2,2-Dimethylpropyl)sulfamoyl group, N-(1-Methylbutyl)sulfamoyl group, N-(2-Methylbutyl)sulfamoyl group, N-1 substituted sulfamoyl groups such as amoyl group, N-(3-methylbutyl)sulfamoyl group, N-cyclopentylsulfamoyl group, N-hexylsulfamoyl group, N-(1,3-dimethylbutyl)sulfamoyl group, N-(3,3-dimethylbutyl)sulfamoyl group, N-heptylsulfamoyl group, N-(1-methylhexyl)sulfamoyl group, N-(1,4-dimethylpentyl)sulfamoyl group, N-octylsulfamoyl group, N-(2-ethylhexyl)sulfamoyl group, N-(1,5-dimethylhexyl)sulfamoyl group, and N-(1,1,2,2-tetramethylbutyl)sulfamoyl group; Examples of N,N-disubstituted sulfamoyl groups include N,N-dimethylsulfamoyl group, N,N-ethylmethylsulfamoyl group, N,N-diethylsulfamoyl group, N,N-propylmethylsulfamoyl group, N,N-isopropylmethylsulfamoyl group, N,N-tert-butylmethylsulfamoyl group, N,N-butylethylsulfamoyl group, N,N-bis(1-methylpropyl)sulfamoyl group, and N,N-heptylmethylsulfamoyl group.

[0050] R 13 and R 14 The 3- to 10-membered ring containing a nitrogen atom that is formed by combining with the above may be a monocyclic ring or a polycyclic ring, and examples thereof include the following: In the formula, * represents a bond.

[0051] [ka]

[0052] R 15 The hydrocarbon group having 1 to 8 carbon atoms represented by the above-mentioned R 1 ~R 3 Among the groups represented by the following formula (1) and having 1 to 20 carbon atoms, those having 1 to 8 carbon atoms are exemplified.

[0053] R 1 ~R 3 are preferably each independently a monovalent saturated hydrocarbon group having 1 to 15 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 15 carbon atoms, or a hydrocarbon group having a carboxy group as a substituent, more preferably a monovalent saturated hydrocarbon group having 1 to 10 carbon atoms, a monovalent aromatic hydrocarbon group having 6 to 12 carbon atoms, or a hydrocarbon group having 1 to 20 carbon atoms and having a carboxy group as a substituent; More preferably, it is a monovalent aromatic hydrocarbon group having 6 to 12 carbon atoms, or a saturated hydrocarbon group having 1 to 10 carbon atoms and having a carboxy group as a substituent. R 4 ~R 9are preferably each independently a hydrogen atom. m represents an integer of 0 to 4, preferably 0 to 3, more preferably 0 to 2, and further preferably 0.

[0054] The compound represented by formula (I-1) is more preferably a compound represented by the following formula (i-1):

[0055] [ka]

[0056] [In formula (i-1), R 1 ~R 3 , L 1 has the same meaning as above.]

[0057] As the compound represented by formula (i-1), as shown in Tables 1-10, there can be mentioned the compounds represented by formulas (i-1-1) to (i-1-240), and the like.

[0058] [Table 1]

[0059] [Table 2]

[0060] [Table 3]

[0061] [Table 4]

[0062] [Table 5]

[0063] [Table 6]

[0064] [Table 7]

[0065] [Table 8]

[0066] [Table 9]

[0067] [Table 10]

[0068] In Tables 1 to 10, the partial structures represented by (a-1) to (a-10), (b-1) to (b-2), (c-1) to (c-6), (d-1) to (d-3), and (e-1) to (e-3) correspond to the following structures. In the formulas, * represents a bond. In addition, Me represents a methyl group, Et represents an ethyl group, Bu represents a butyl group, and Ph represents a phenyl group.

[0069] [ka]

[0070] The compounds represented by formulas (i-1-85) to (i-1-120) are preferred, the compounds represented by formulas (i-1-85) to (i-1-96) are more preferred, and the compounds represented by formulas (i-1-86) to (i-1-95) are even more preferred.

[0071] The compound represented by formula (I-2) is more preferably a compound represented by the following formula (i-2):

[0072] [ka] [In formula (i-2), R 1 ~R 3 , L 2 has the same meaning as above.]

[0073] As the compound represented by formula (i-2), as shown in Tables 11-12, there can be mentioned the compounds represented by formulas (i-2-1) to (i-2-40), and the like.

[0074] [Table 11]

[0075] [Table 12]

[0076] In Tables 11 and 12, the partial structures represented by (f-1) and (f-2) correspond to the following structures: In the formula, * represents a bond.

[0077] [ka]

[0078] The compound represented by formula (I-3) is more preferably a compound represented by the following formula (i-3):

[0079] [ka] [In formula (i-3), R 1 ~R 3 , L 3 has the same meaning as above.]

[0080] As the compound represented by formula (i-3), as shown in Table 13, there can be mentioned the compounds represented by formulae (i-3-1) to (i-3-20), and the like.

[0081] [Table 13]

[0082] In Table 13, the partial structure represented by (g-1) corresponds to the following structure: In the formula, * represents a bond.

[0083] [ka]

[0084] In the present invention, the compound (I) is included in a colorant (hereinafter, may be referred to as colorant (A)), and the colorant is further included in a colored resin composition. The compound (I) included in the colorant may be one or more of the compounds represented by formula (I-1), formula (I-2), or formula (I-3). Among the compounds represented by formula (I-1), formula (I-2), or formula (I-3), the compound represented by formula (I-1) is preferred, and the compound represented by formula (i-1) is more preferred.

[0085] The content of compound (I) refers to the total content of the compounds represented by formula (I-1), formula (I-2), or formula (I-3), and is, for example, 5 mass% or more, preferably 10 mass% or more, and more preferably 12 mass% or more, relative to the total amount of colorant (A), and for example, 50 mass% or less, preferably 40 mass% or less, and more preferably 30 mass% or less.

[0086] The content of compound (I) is usually 0.1 mass% or more and 50 mass% or less, preferably 1 mass% or more and 40 mass% or less, and more preferably 1 mass% or more and 30 mass% or less, based on the total amount of solids in the colored resin composition.

[0087] The colored resin composition of the present invention may contain a colorant other than the compound (I) (hereinafter, may be referred to as colorant (A2)) as the colorant (A). The colorant (A2) may contain one or more dyes.

[0088] The coloring matter constituting the colorant (A2) may be either a dye or a pigment. Examples of the dye include known dyes described in the Color Index (published by The Society of Dyers and Colourists) and Dyeing Notes (Shikisensha). In addition, examples of the dye include, according to their chemical structure, azo dyes, anthraquinone dyes, triphenylmethane dyes, xanthene dyes (excluding the compounds represented by formulas (I-1) to (I-3)), cyanine dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, and phthalocyanine dyes. Among these, organic solvent-soluble dyes are preferred. These dyes may be used in combination of two or more kinds.

[0089] Specifically, dyes with the following Color Index (CI) numbers are included: CI Solvent Yellow 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162; CI Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251; CI Reactive Yellow 2, 76, 116; CI Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141; CI Disperse Yellow 51, 54, 76; CI Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 99; CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173; CI Reactive Orange 16; CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI Solvent Red 24, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; CI Acid Red 73, 80, 91, 92, 97, 138, 151, 211, 274, 289; CI Acid Violet 34, 102; CI Disperse Violet 26, 27; CI Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; CI Solvent Blue 14, 18, 35, 36, 45, 58, 59, 59:1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; CI Acid Blue 25, 27, 40, 45, 78, 80, 112; CI Direct Blue 40; CI Disperse Blue 1, 14, 56, 60; CI Solvent Green 1, 3, 5, 28, 29, 32, 33; CI Acid Green 3, 5, 9, 25, 27, 28, 41; CI Basic Green 1; CI Bat Green 1st Class.

[0090] As the pigment, known pigments can be used, for example, pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists). Two or more kinds of pigments may be used in combination. Specifically, yellow pigments such as CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214; Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73; Red pigments such as CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 179, 180, 192, 202, 208, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273, brominated diketopyrrolopyrroles; Blue pigments such as CI Pigment Blue 15, 15:3, 15:4, 15:6, 60; Violet pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, 38; Examples of green pigments include CI Pigment Green 7, 36, 58, and 59. Among these, the colorant (A2) is preferably a pigment, and more preferably a blue pigment.

[0091] The dye constituting the colorant (A2) may be subjected to, as necessary, a rosin treatment, a surface treatment using a colorant derivative having an acidic or basic group introduced therein, a grafting treatment to the surface of the pigment using a polymer compound, a microparticulation treatment using a sulfuric acid microparticulation method, a washing treatment using an organic solvent or water to remove impurities, a removal treatment using an ion exchange method for ionic impurities, etc. The particle size of the dye is preferably approximately uniform. The dye (particularly the pigment) is uniformly dispersed in the dispersion by adding a dispersant and carrying out a dispersion treatment.

[0092] Examples of the dispersant include surfactants, which may be cationic, anionic, nonionic, or amphoteric. Specific examples include polyester, polyamine, and acrylic surfactants. These dispersants may be used alone or in combination of two or more. Examples of the dispersant, in terms of trade name, include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLOWRENE (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Co., Ltd.), EFKA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK-Chemie), and BYK (registered trademark) (manufactured by BYK-Chemie). In order to assist in dispersion stabilization, a resin (B) described later may be used in combination.

[0093] When a dispersant is used, the amount of the dispersant used is preferably 100 parts by mass or less, and more preferably 5 parts by mass or more and 50 parts by mass or less, relative to 100 parts by mass of the pigment. When the amount of the dispersant used is within the above range, a pigment-containing liquid in a more uniformly dispersed state tends to be obtained.

[0094] The content of colorant (A2) relative to the total amount of colorant (A) is, for example, 55 mass% or more, preferably 65 mass% or more, and more preferably 75 mass% or more, and for example, 99 mass% or less, preferably 95 mass% or less, and more preferably 90 mass% or less.

[0095] In the present invention, the colored resin composition contains a colorant (A) and a resin (hereinafter, may be referred to as resin (B)). The colored resin composition of the present invention may contain a polymerizable compound (hereinafter, may be referred to as a polymerizable compound (C)) and a polymerization initiator (hereinafter, may be referred to as a polymerization initiator (D)). It is preferable that the colored curable resin composition of the present invention further contains a solvent (hereinafter, sometimes referred to as solvent (E)). The colored curable resin composition of the present invention may contain a leveling agent. In this specification, the compounds exemplified as each component may be used alone or in combination of two or more kinds, unless otherwise specified.

[0096] <Resin (B)> Resin (B) is not particularly limited, but is preferably an alkali-soluble resin, and more preferably a resin having a structural unit derived from at least one type (a) (hereinafter sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides. Resin (B) further preferably has at least one structural unit selected from the group consisting of a structural unit derived from a monomer (b) (hereinafter sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond, a structural unit derived from a monomer (c) (however, different from (a) and (b)) (hereinafter sometimes referred to as "(c)") copolymerizable with (a), and a structural unit having an ethylenically unsaturated bond in a side chain.

[0097] Specific examples of (a) include acrylic acid, methacrylic acid, maleic anhydride, itaconic anhydride, and 3,4,5,6-tetrahydrophthalic anhydride; Examples of the monomer include mono[2-(meth)acryloyloxyethyl] succinate, and preferred are acrylic acid, methacrylic acid, and maleic anhydride. In this specification, the term "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" have the same meaning.

[0098] (b) is preferably a monomer having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring) and a (meth)acryloyloxy group. Examples of (b) include glycidyl (meth)acrylate, vinylbenzyl glycidyl ether, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl(meth)acrylate, 3-ethyl-3-(meth)acryloyloxymethyloxetane, tetrahydrofurfuryl(meth)acrylate, etc., and preferably, glycidyl(meth)acrylate, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate, 3-ethyl-3-(meth)acryloyloxymethyloxetane.

[0099] Examples of (c) include methyl (meth)acrylate, butyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]Decan-8-yl (meth)acrylate benzyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, styrene, vinyltoluene, etc., with styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, 2-hydroxyethyl (meth)acrylate, etc. being preferred.

[0100] The resin having a structural unit having an ethylenically unsaturated bond in the side chain can be produced by adding (b) to a copolymer of (a) and (c), or by adding (a) to a copolymer of (b) and (c). The resin may be a resin obtained by adding (a) to a copolymer of (b) and (c) and then reacting with a carboxylic acid anhydride.

[0101] The polystyrene-equivalent weight average molecular weight of resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 5,000 to 30,000. The dispersity of the resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1.1-6, and more preferably 1.2-4.

[0102] The acid value of the resin (B) is preferably 50 to 170 mg-KOH / g, more preferably 60 to 150 mg-KOH / g, and further preferably 70 to 135 mg-KOH / g, calculated as solid content. The acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be determined, for example, by titration with an aqueous potassium hydroxide solution.

[0103] The content of the resin (B) is preferably from 10 to 70% by mass, more preferably from 15 to 65% by mass, and further preferably from 20 to 60% by mass, based on the total solid content.

[0104] <Polymerizable compound (C)> The polymerizable compound (C) is a compound that can be polymerized by active radicals and / or acids generated from the polymerization initiator (D), and examples thereof include compounds having a polymerizable ethylenically unsaturated bond, and are preferably (meth)acrylic acid ester compounds.

[0105] Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, and dipentaerythritol hexa(meth)acrylate.

[0106] The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, and more preferably 250 or more and 1,500 or less.

[0107] The content of the polymerizable compound (C) is preferably from 10 to 70% by mass, more preferably from 15 to 65% by mass, and further preferably from 20 to 60% by mass, based on the total solid content.

[0108] <Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that generates active radicals, acids, etc. by the action of light or heat and can initiate polymerization, and known polymerization initiators can be used. Examples of polymerization initiators that generate active radicals include N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, 2-methyl-2-morpholino-1-(4-methylsulfonylphenyl)-2-methylsulfonylphenyl, and the like. Examples of such amines include 2-dimethylamino-1-(4-morpholinophenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 1-hydroxycyclohexyl phenyl ketone 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, and 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole.

[0109] The polymerization initiator is preferably a polymerization initiator containing at least one selected from the group consisting of a triazine compound, an acylphosphine oxide compound, an alkylphenone compound, an O-acyloxime compound, and a biimidazole compound, and more preferably a polymerization initiator containing an O-acyloxime compound.

[0110] The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the content of the polymerization initiator (D) is within the above range, the sensitivity is increased and the exposure time tends to be shortened, thereby improving the productivity of the color filter.

[0111] The content of the O-acyloxime compound is preferably 50% by mass or more, more preferably 80% by mass or more, even more preferably 90% by mass or more, and particularly preferably 95% by mass or more, based on the total amount of the polymerization initiator (D). When the content of the O-acyloxime compound is within the above range, there is a tendency that the sensitivity and developability when forming a colored pattern, and a color filter with high brightness even when the colorant content is high, can be produced.

[0112] The colored curable resin composition of the present invention may contain a polymerization initiator aid.

[0113] <Polymerization initiator aid (D1)> The polymerization initiation aid (D1) is a compound used to promote the polymerization of a polymerizable compound whose polymerization has been initiated by a polymerization initiator, or a sensitizer. When the polymerization initiation aid (D1) is contained, it is usually used in combination with the polymerization initiator (D). Examples of the polymerization initiator aid (D1) include 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, 9,10-dimethoxyanthracene, 2,4-diethylthioxanthone, N-phenylglycine, and the like.

[0114] When these polymerization initiation aids (D1) are used, the content thereof is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with higher sensitivity, and the productivity of the color filter tends to improve.

[0115] The colored curable resin composition of the present invention preferably contains a solvent.

[0116] <Solvent (E)> The solvent (E) is not particularly limited, and a solvent commonly used in the field can be used. For example, ester solvent (solvent containing -COO- in the molecule and not containing -O-), ether solvent (solvent containing -O- in the molecule and not containing -COO-), ether ester solvent (solvent containing -COO- and -O- in the molecule), ketone solvent (solvent containing -CO- in the molecule and not containing -COO-), alcohol solvent (solvent containing OH in the molecule and not containing -O-, -CO- and -COO-), aromatic hydrocarbon solvent, amide solvent, dimethyl sulfoxide, etc. can be mentioned.

[0117] Examples of the solvent include ester solvents (solvents that contain -COO- and do not contain -O- in the molecule) such as ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, methyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone; ether solvents (solvents that contain -O- and do not contain -COO- in the molecule) such as ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, 3-methoxy-1-butanol, diethylene glycol dimethyl ether, and diethylene glycol methyl ethyl ether; Ether ester solvents (solvents containing -COO- and -O- in the molecule) such as methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, 3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, and diethylene glycol monoethyl ether acetate; Ketone solvents such as 4-hydroxy-4-methyl-2-pentanone, heptanone, 4-methyl-2-pentanone, and cyclohexanone (solvents that contain -CO- but not -COO- in the molecule); Alcohol solvents such as butanol, cyclohexanol, and propylene glycol (solvents that contain OH in the molecule but do not contain -O-, -CO-, or -COO-); Examples of the solvent include aromatic hydrocarbon solvents such as toluene and xylene, and amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0118] More preferred solvents are propylene glycol monomethyl ether acetate, 4-hydroxy-4-methyl-2-pentanone, propylene glycol monomethyl ether, ethyl lactate, cyclohexanone, N-methylpyrrolidone and ethyl 3-ethoxypropionate.

[0119] The solvent is preferably a mixed solvent containing propylene glycol monomethyl ether acetate.As the solvent to be combined with propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, 3-ethoxypropionate ethyl, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, dipropylene glycol methyl ether acetate, 3-methoxybutyl acetate, 3-methoxy-1-butanol, N-methylpyrrolidone and 4-hydroxy-4-methyl-2-pentanone are preferred, propylene glycol monomethyl ether, dipropylene glycol methyl ether acetate, ethyl lactate, 3-methoxybutyl acetate, 3-methoxy-1-butanol, N-methylpyrrolidone, 4-hydroxy-4-methyl-2-pentanone and 3-ethoxypropionate ethyl are more preferred, and ethyl lactate, 4-hydroxy-4-methyl-2-pentanone, N-methylpyrrolidone and propylene glycol monomethyl ether are even more preferred.

[0120] The content of the solvent to be combined with propylene glycol monomethyl ether acetate is preferably 1% by mass or more and 90% by mass or less, more preferably 3% by mass or more and 85% by mass or less, and even more preferably 5% by mass or more and 80% by mass or less, based on the total amount of the solvent.

[0121] When the solvent (E) is contained, the content of the solvent (E) is preferably 20 to 90 mass%, more preferably 25 to 85 mass%, based on the total amount of the colored resin composition of the present invention. In other words, the total amount of solids in the colored resin composition is preferably 10 to 80 mass%, more preferably 15 to 75 mass%. When the content of the solvent (E) is within the above range, the flatness during application is good, and the color density is not insufficient when a color filter is formed, so that the display characteristics tend to be good.

[0122] <Other ingredients> The colored resin composition of the present invention may contain additives known in the art, such as leveling agents, fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, and chain transfer agents, as necessary.

[0123] <Method of producing colored resin composition> The colored resin composition of the present invention can be prepared by mixing the colorant (A), the resin (B), and, if necessary, the polymerizable compound (C), the polymerization initiator (D), the solvent (E) and other components.

[0124] <Manufacturing method of color filters> Methods for producing a colored pattern from the colored resin composition of the present invention include photolithography, inkjet, and printing. Among them, photolithography is preferred. In the photolithography, a colored coating film, which is a cured product of the colored resin composition layer, can be formed by not using a photomask during exposure and / or not developing. The colored pattern or colored coating film thus formed is the color filter of the present invention.

[0125] The colored resin composition can be used to prepare a color filter having excellent contrast. The color filter is useful as a color filter for use in display devices (e.g., liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging devices. EXAMPLES

[0126] The present invention will now be described in more detail with reference to examples. In the examples, % and parts indicating the content or amount used are by weight unless otherwise specified.

[0127] In the following examples, the structures of the compounds were identified by mass spectrometry (LC; Agilent 1200 model, MASS; Agilent LC / MSD model).

[0128] Example 1 In a flask equipped with a condenser and a stirrer, 3.0 parts of the compound represented by formula (X) (Pink Base (manufactured by Chugai Chemical Industry)), 21 parts of N-methylpyrrolidone, and 1.7 parts of potassium t-butoxide (content 85%) were added and stirred at room temperature for 45 minutes, and then 0.6 parts of 1,6-dibromohexane was added and stirred at the same temperature for 2.5 hours. The resulting reaction liquid was added to 63 parts of 2N hydrochloric acid and stirred at room temperature for 1 hour, whereby crystals were precipitated. The precipitated crystals were filtered off, washed thoroughly with ion-exchanged water, and dried under reduced pressure at 60°C to obtain 13.3 parts of a crude product. This was purified by silica gel column chromatography (solvent: chloroform / methanol 100 / 1 to 20 / 1), and the obtained fraction was concentrated under reduced pressure and dried under reduced pressure at 60°C to obtain 1.2 parts of a compound represented by formula (A-1-IM).

[0129] [ka]

[0130] [ka]

[0131] Identification of the compound represented by formula (A-1-IM) (Mass spectrometry) Ionization mode = ESI + : m / z= [M+H] + 1231.5 Exact Mass: 1230.5

[0132] In a flask equipped with a cooling tube and a stirrer, 1.2 parts of the compound represented by formula (A-1-IM), 8.2 parts of N-methylpyrrolidone, 0.9 parts of potassium carbonate, and 1.1 parts of ethyl 4-bromobutyrate were added and stirred at 100 ° C. for 3.5 hours. After cooling, 7 parts of N-methylpyrrolidone and 12.0 parts of 4% aqueous sodium hydroxide solution were added to the resulting reaction liquid and stirred at room temperature for 7.5 hours. When the resulting reaction liquid was added to 30 parts of 2N hydrochloric acid and stirred at room temperature for 30 minutes, crystals were precipitated. The precipitated crystals were filtered, washed thoroughly with ion-exchanged water, and dried under reduced pressure at 60 ° C. to obtain 1.2 parts of the compound represented by formula (i-1-93) (hereinafter sometimes referred to as "compound (A-1)").

[0133] [ka]

[0134] Identification of the compound represented by formula (A-1) (Mass spectrometry) Ionization mode = ESI + : m / z= [M+H] + 1403.5 Exact Mass: 1402.5

[0135] Example 2 In a flask equipped with a condenser and a stirrer, 3.0 parts of the compound represented by formula (X), 21 parts of N-methylpyrrolidone, and 1.3 parts of sodium t-butoxide were added and stirred at room temperature for 40 minutes, and then 0.6 parts of 1,7-dibromoheptane was added and stirred at the same temperature for 4.5 hours. The resulting reaction solution was added to 63 parts of 2N hydrochloric acid and stirred at room temperature for 30 minutes, whereby crystals were precipitated. The precipitated crystals were filtered off, washed thoroughly with ion-exchanged water, and dried under reduced pressure at 60°C to obtain 12.0 parts of a crude product. This was purified by silica gel column chromatography (solvent: chloroform / methanol 100 / 1 to 10 / 1), and the obtained fraction was concentrated under reduced pressure and dried under reduced pressure at 60°C to obtain 1.0 part of a compound represented by formula (A-2-IM).

[0136] [ka]

[0137] Identification of the compound represented by formula (A-2-IM) (Mass spectrometry) Ionization mode = ESI + : m / z= [M+H] + 1245.3 Exact Mass: 1244.5

[0138] In a flask equipped with a cooling tube and a stirrer, 1.0 part of the compound represented by formula (A-2-IM), 7.2 parts of N-methylpyrrolidone, 0.8 parts of potassium carbonate, and 1.0 parts of ethyl 4-bromobutyrate were added and stirred at 100°C for 6 hours. After cooling, 6.1 parts of N-methylpyrrolidone and 10.4 parts of 4% aqueous sodium hydroxide solution were added to the resulting reaction liquid and stirred at room temperature for 5.5 hours. When the resulting reaction liquid was added to 30 parts of 2N hydrochloric acid and stirred at room temperature for 1 hour, crystals were precipitated. The precipitated crystals were filtered, washed thoroughly with ion-exchanged water, and dried under reduced pressure at 60°C to obtain 1.1 parts of the compound represented by formula (i-1-94) (hereinafter sometimes referred to as "compound (A-2)").

[0139] [ka]

[0140] Identification of the compound represented by formula (A-2) (Mass spectrometry) Ionization mode = ESI + : m / z= [M+H] + 1417.8 Exact Mass: 1416.6

[0141] Example 3 In a flask equipped with a condenser and a stirrer, 3.0 parts of the compound represented by formula (X), 21 parts of N-methylpyrrolidone, and 1.3 parts of sodium t-butoxide were added and stirred at room temperature for 50 minutes, and then 0.6 parts of 1,5-dibromopentane was added and stirred at the same temperature for 4 hours. The resulting reaction liquid was added to 63 parts of 2N hydrochloric acid and stirred at room temperature for 30 minutes, whereby crystals were precipitated. The precipitated crystals were filtered off, washed thoroughly with ion-exchanged water, and dried under reduced pressure at 60°C to obtain 15.2 parts of a crude product. This was purified by silica gel column chromatography (solvent: chloroform / methanol 100 / 1 to 10 / 1), and the obtained fraction was concentrated under reduced pressure and dried under reduced pressure at 60°C to obtain 3.0 parts of the compound represented by formula (A-3-IM).

[0142] [ka]

[0143] Identification of the compound represented by formula (A-3-IM) (Mass spectrometry) Ionization mode = ESI + : m / z= [M+H] + 1217.8 Exact Mass: 1216.5

[0144] In a flask equipped with a cooling tube and a stirrer, 1.0 part of the compound represented by formula (A-3-IM), 7 parts of N-methylpyrrolidone, 0.8 parts of potassium carbonate, and 1.0 part of ethyl 4-bromobutyrate were added and stirred at 100°C for 5.5 hours. After cooling, 6 parts of N-methylpyrrolidone and 10.4 parts of 4% aqueous sodium hydroxide solution were added to the resulting reaction liquid and stirred at room temperature for 6 hours. When the resulting reaction liquid was added to 30 parts of 2N hydrochloric acid and stirred at room temperature for 40 minutes, crystals were precipitated. The precipitated crystals were filtered, washed thoroughly with ion-exchanged water, and dried under reduced pressure at 60°C to obtain 1.0 part of the compound represented by formula (i-1-92) (hereinafter sometimes referred to as "compound (A-3)").

[0145] [ka]

[0146] Identification of the compound represented by formula (A-3) (Mass spectrometry) Ionization mode = ESI + : m / z= [M+H] + 1389.8 Exact Mass: 1388.5

[0147] Example 4 In a flask equipped with a condenser and a stirrer, 3.0 parts of the compound represented by formula (X), 21 parts of N-methylpyrrolidone, and 1.3 parts of sodium t-butoxide were added and stirred at room temperature for 1 hour, and then 0.7 parts of 1,8-dibromooctane was added and stirred at the same temperature for 3 hours. The resulting reaction liquid was added to 63 parts of 2N hydrochloric acid and stirred at room temperature for 45 minutes, whereby crystals were precipitated. The precipitated crystals were filtered off, washed thoroughly with ion-exchanged water, and dried under reduced pressure at 60°C to obtain 15.0 parts of a crude product. This was purified by silica gel column chromatography (solvent: chloroform / methanol 100 / 1 to 10 / 1), and the obtained fraction was concentrated under reduced pressure and dried under reduced pressure at 60°C to obtain 1.2 parts of the compound represented by formula (A-4-IM).

[0148] [ka]

[0149] Identification of the compound represented by formula (A-4-IM) (Mass spectrometry) Ionization mode = ESI + : m / z= [M+H] + 1259.8 Exact Mass: 1258.5

[0150] In a flask equipped with a cooling tube and a stirrer, 1.0 part of the compound represented by formula (A-4-IM), 7 parts of N-methylpyrrolidone, 0.8 parts of potassium carbonate, and 0.9 parts of ethyl 4-bromobutyrate were added and stirred at 100°C for 7.5 hours. After cooling, 5.9 parts of N-methylpyrrolidone and 10.0 parts of 4% aqueous sodium hydroxide solution were added to the resulting reaction liquid and stirred at room temperature for 7 hours. When the resulting reaction liquid was added to 30 parts of 2N hydrochloric acid and stirred at room temperature for 1 hour, crystals were precipitated. The precipitated crystals were filtered, washed thoroughly with ion-exchanged water, and dried under reduced pressure at 60°C to obtain 1.1 parts of the compound represented by formula (i-1-95) (hereinafter sometimes referred to as "compound (A-4)").

[0151] [ka]

[0152] Identification of the compound represented by formula (A-4) (Mass spectrometry) Ionization mode = ESI + : m / z= [M+H] + 1431.8 Exact Mass: 1430.6

[0153] [Synthesis Example 1] In a flask equipped with a condenser and a stirrer, 1 part of the compound represented by formula (X), 7 parts of N-methylpyrrolidone, 1.0 part of potassium carbonate, and 2.0 parts of ethyl 4-bromobutyrate were added and stirred at 100°C for 7.5 hours. After cooling, 20 parts of 2N hydrochloric acid were added to the resulting reaction liquid, which was extracted twice with 45 parts of chloroform. The chloroform layers were combined, washed with saturated saline, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the mixture was dried under reduced pressure at 60°C to obtain 4.1 parts of the crude compound represented by formula (A-5-IM).

[0154] [ka]

[0155] Identification of the compound represented by formula (A-5-IM) (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 803.5 Exact Mass: 802.3

[0156] In a flask equipped with a condenser and a stirrer, 4.1 parts of the compound represented by formula (A-5-IM), 9.8 parts of methanol, and 3.5 parts of an 8% aqueous sodium hydroxide solution were added and stirred at room temperature for 6 hours. The resulting reaction solution was added to 30 parts of 2N hydrochloric acid and stirred at room temperature for 30 minutes, resulting in the precipitation of crystals. The precipitated crystals were filtered off, thoroughly washed with ion-exchanged water, and dried under reduced pressure at 60°C to obtain 1.0 part of the compound represented by formula (A-5).

[0157] [ka]

[0158] Identification of the compound represented by formula (A-5) (Mass spectrometry) Ionization mode = ESI + : m / z= [M+H] + 747.5 Exact Mass: 746.3

[0159] [Synthesis Example 2] A suitable amount of nitrogen was poured into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer to replace the atmosphere with nitrogen, and 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were added and heated to 85°C with stirring. Next, 38 parts of acrylic acid and 3,4-epoxytricyclo[5.2.1.0 2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6A mixture of 25 parts of a mixture of decan-9-yl acrylate (content ratio 1:1 by molar ratio), 137 parts of N-cyclohexylmaleimide, 50 parts of 2-hydroxyethyl methacrylate, and 338 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a solution of 5 parts of 2,2-azobisisobutyronitrile dissolved in 88 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the completion of the dropwise addition, the mixture was kept at 85°C for 4 hours and then cooled to room temperature to obtain a copolymer (resin (B-1)) solution with a viscosity of 23 mPas measured with a B-type viscometer (23°C) and a solid content of 25.6%. The weight average molecular weight Mw of the resulting copolymer was 8.0 x 10 3 The resin (B-1) had the following structural units: a polydispersity of 2.1, and an acid value calculated as solid content of 109 mg-KOH / g.

[0160] [ka]

[0161] The weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by GPC under the following conditions. Equipment: K2479 (Shimadzu Corporation) Column: SHIMADZU Shim-pack GPC-80M Column temperature: 40°C Solvent: THF (tetrahydrofuran) Test solution concentration: 25mg / mL (solvent: THF) Flow rate; 1.0mL / min Detector: RI Calibration standard material: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation) The ratio of the weight average molecular weight and the number average molecular weight calculated in terms of polystyrene obtained above was defined as the dispersity (Mw / Mn).

[0162] [Example 5] (A) Colorant: CI Pigment Blue 15:6 (pigment) 17 parts Acrylic pigment dispersant 6 parts Propylene glycol monomethyl ether acetate 143 parts The pigment is thoroughly dispersed using a bead mill, and then (A) Colorant: Compound (A-1) 3 parts (B) Resin: Resin (B-1) (solid content equivalent) 50 parts (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 9 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.14 parts (E) Solvent: 567 parts of propylene glycol monomethyl ether acetate (E) Solvent: 4-hydroxy-4-methyl-2-pentanone 58 parts The above were mixed to obtain a colored resin composition.

[0163] [Example 6] A colored resin composition was obtained by carrying out the same procedure as in Example 5, except that the compound (A-2) was used instead of the compound (A-1).

[0164] [Example 7] A colored resin composition was obtained by carrying out the same procedure as in Example 5, except that the compound (A-3) was used instead of the compound (A-1).

[0165] [Example 8] A colored resin composition was obtained by carrying out the same procedure as in Example 5, except that the compound (A-4) was used instead of the compound (A-1).

[0166] [Comparative Example 1] (A) Colorant: CI Pigment Blue 15:6 (pigment) 17 parts Acrylic pigment dispersant 6 parts Propylene glycol monomethyl ether acetate 143 parts The pigment is thoroughly dispersed using a bead mill, and then (A) Colorant: Compound (A-5) 3 parts (B) Resin: Resin (B-1) (solid content equivalent) 50 parts (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 9 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.14 parts (E) Solvent: 582 parts of propylene glycol monomethyl ether acetate (E) Solvent: 4-hydroxy-4-methyl-2-pentanone 43 parts The above were mixed to obtain a colored resin composition.

[0167] [Example 9] (A) Colorant: CI Pigment Blue 15:6 (pigment) 18.1 parts Acrylic pigment dispersant 6 parts Propylene glycol monomethyl ether acetate 150 parts The pigment is thoroughly dispersed using a bead mill, and then (A) Colorant: Compound (A-1) 2.2 parts (B) Resin: Resin (B-1) (solid content equivalent) 50 parts (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 9 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.14 parts (E) Solvent: 577 parts of propylene glycol monomethyl ether acetate (E) Solvent: 4-hydroxy-4-methyl-2-pentanone 43 parts The above were mixed to obtain a colored resin composition.

[0168] [Example 10] (A) Colorant: CI Pigment Blue 15:6 (pigment) 18.8 parts Acrylic pigment dispersant 7 parts Propylene glycol monomethyl ether acetate 155 parts The pigment is thoroughly dispersed using a bead mill, and then (A) Colorant: Compound (A-1) 1.6 parts (B) Resin: Resin (B-1) (solid content equivalent) 50 parts (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 9 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.14 parts (E) Solvent: 585 parts of propylene glycol monomethyl ether acetate (E) Solvent: 4-hydroxy-4-methyl-2-pentanone 31 parts The above were mixed to obtain a colored resin composition.

[0169] <Preparation of colored patterns> The colored resin composition was applied by spin coating onto a 5 cm square glass substrate (Eagle 2000; Corning Incorporated), and then prebaked at 100°C for 3 minutes to obtain a colored composition layer. After cooling, the substrate on which the colored composition layer was formed was exposed to a quartz glass photomask at a distance of 100 μm, and the substrate was exposed to an exposure machine (TME-150RSK; Topcon Corporation) at 150 mJ / cm under atmospheric conditions. 2 The photomask was irradiated with light at an exposure dose of 100 μm (based on 365 nm). A photomask with a 100 μm line and space pattern was used. The colored composition layer after the light irradiation was developed by immersion in an aqueous developer containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 24° C. for 60 seconds, washed with water, and then post-baked in an oven at 230° C. for 20 minutes to obtain a colored pattern. From the colored resin compositions of Examples 5 to 10, colored patterns with good shapes were formed.

[0170] <Film thickness measurement> The film thickness of the resulting colored pattern was measured using a film thickness measuring device (DEKTAK3; manufactured by Nippon Shinku Gijutsu Co., Ltd.).

[0171] <Color evaluation> The resulting colored pattern was measured for spectroscopy using a colorimeter (OSP-SP-200; Olympus Corporation), and the xy chromaticity coordinates (x, y) and stimulus value Y in the CIE XYZ color system were measured using the characteristic function of Illuminant C. A larger Y value indicates a higher lightness.

[0172] <Contrast evaluation> A colored coating film having a thickness of 2 μm was prepared by the same procedure as in the preparation of the colored pattern, except that no photomask was used during exposure. The contrast of the obtained colored coating film was measured using a contrast meter (CT-1; manufactured by Tsubosaka Electric Co., Ltd., color difference meter BM-5A; manufactured by Topcon, light source; F-10, polarizing film; manufactured by Tsubosaka Electric Co., Ltd.) with a blank value of 30,000. If the contrast of the colored coating film is high, it can be said that the contrast of the colored pattern is also high. The results are shown in Table 14.

[0173] [Table 14]

[0174] From the examples, it was confirmed that the color filter obtained from the composition containing the compound of the present invention exhibits high contrast. From this, it is understood that the display device including the color filter obtained from the colored resin composition containing the compound of the present invention has excellent display characteristics.

Claims

1. A compound represented by formula (I-1), formula (I-2), or formula (I-3). 【Chemistry 1】 [In formula (I-1), formula (I-2), or formula (I-3), L 1 is a divalent linking group, L 2 is a trivalent linking group, L 3 represents a tetravalent linking group. b 11 ~b 19 each independently represents formula (i), a represents L 1 , L 2 , or L 3 Represents a bond with . In formula (i), R 1 , R 2 and R 3 each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a hydrogen atom, and —CH 2 - is -O-, -CO- or -NR 11 It may be replaced by -. R 1 , R 2 and R 3 At least one of the groups represents a hydrocarbon group having a carboxy group as a substituent. R 11 represents a hydrocarbon group having 1 to 8 carbon atoms. R 4 ~R 9 each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms. R 10 represents a hydrocarbon group having 1 to 10 carbon atoms, -OH, -SO 3 - Z + , -CO 2 - Z + , -CO 2 R 12 , -SO 3 R 12 Or -SO 2 N.R. 13 R 14 Represents. Z + is a hydron, an alkali metal cation or N + (R 15 ) 4 Represents. R 12 represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms. R 13 and R 14 each independently represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and -CH 2 - is -O-, -CO- or -NR 11 It may be replaced with -. R 13 and R 14 may be bonded to each other to form a 3- to 10-membered ring containing a nitrogen atom. R 15 represents a hydrogen atom or a hydrocarbon group having 1 to 8 carbon atoms; R 15 When multiple are present, they may be the same or different. m represents an integer of 0 to 4, and when m is 2 or more, a plurality of R 10 may be the same or different.

2. A colored resin composition comprising the compound of claim 1 and a resin.

3. The colored resin composition according to claim 2 , further comprising a polymerizable compound and a polymerization initiator.

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

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

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