Benzoperylene compound and colored curable resin composition

Abstract

To provide a compound having high fluorescence intensity as a fluorescent dye, and a colored curable resin composition capable of forming a color filter having excellent fluorescence intensity.SOLUTION: A colored curable resin composition comprises a colorant, a resin, a polymerizable compound, and a polymerization initiator, where the colorant includes a benzoperylene compound.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a benzoperylene compound useful as a colorant, particularly as a dye, and to a colored curable resin composition containing the benzoperylene compound. [Background technology]

[0002] Color filters used in displays such as liquid crystal displays, electroluminescent displays, and plasma displays, and solid-state imaging devices such as CCD and CMOS sensors, are manufactured from colored curable resin compositions. Various colorants are used as the colored curable resin compositions for forming the color filters. Perylene compounds are also known as fluorescent dyes (Non-Patent Document 1), and examples of using perylene compounds in color conversion layers are also known (Patent Document 1). [Prior art documents] [Patent documents]

[0003] [Patent Document 1] JP 2018-124553 A [Non-patent literature]

[0004] [Non-Patent Document 1] BASF Technical Report (Lumogen(R) F), BASF, November 1997, 2-6 Summary of the Invention [Problem to be solved by the invention]

[0005] However, the above-mentioned conventionally known perylene compounds sometimes do not have a sufficient fluorescence intensity. Therefore, the present invention aims to provide a colored curable resin composition containing a colorant, particularly a compound having high fluorescence intensity as a fluorescent dye, and a compound (preferably a dye) capable of forming a color filter having excellent fluorescence intensity. [Means for solving the problem]

[0006] The gist of the present invention is as follows. [1] A composition comprising a colorant, a resin, a polymerizable compound, and a polymerization initiator; The colored curable resin composition, wherein the colorant comprises a benzoperylene compound. [2] The colored curable resin composition according to [1], wherein the benzoperylene compound is a compound represented by formula (I): [ka] [In formula (I), R 1 and R 2 represent, independently of each other, a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, an aromatic heterocyclic group having 1 to 30 carbon atoms which may have a substituent, or a group in which the above-mentioned hydrocarbon group which may have a substituent and the above-mentioned aromatic heterocyclic group which may have a substituent are bonded together. R 3 ~R 10 are, independently of each other, a hydrogen atom, *-R 11 , *-OR 11 , *-CO-OR 11 , a halogen atom, a hydroxy group, a carboxy group or a nitro group. R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 7 and R 8 , R 8 and R 9 and R 9 and R 10 are each independently *-CO-O-CO-* or *-CO-N(R 11 )-CO-* may form a ring. R 11 represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, R 11 When there are multiple, they may be different from each other. * represents a bond.] [3] The colored curable resin composition according to [1] or [2], wherein the colorant further contains a perylene compound. [4] A color filter formed from the colored curable resin composition according to any one of [1] to [3]. [5] A display device comprising the color filter according to [4]. [6] A compound represented by formula (Ia). [ka] [In formula (Ia), R 1a and R 2a each independently represents an optionally substituted aryl group having 6 to 20 carbon atoms or an optionally substituted heteroaryl group having 1 to 20 carbon atoms. R 3a , R 6a , R 7a , R 8a , R 9a and R 10a are, independently of each other, a hydrogen atom, *-R 11a , *-OR 11a , *-CO-OR 11a , a halogen atom, a hydroxy group, a carboxy group or a nitro group. R 11a represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, R 11a When there are multiple, they may be different from each other. R 4a and R 5a are, independently of each other, *-CO-OR 11a or R 4a and R 5a are bonded to form a group represented by formula (a) or formula (b). [ka] [In formulas (a) and (b), R b1 and R b2 each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. Rc1 represents an aryl group having 6 to 20 carbon atoms which may have a substituent.] R 4a and R 5a is a group represented by formula (b), R 1a , R 2a and R c1 The above three do not have the same base. * represents a bond.] Effect of the Invention

[0007] According to the present invention, it is possible to provide a compound capable of forming a color filter having excellent fluorescence intensity, and a colored curable resin composition. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0008] The colored curable resin composition of the present invention contains a colorant (hereinafter, may be referred to as colorant (A)), a resin (hereinafter, may be referred to as resin (B)), a polymerizable compound (hereinafter, may be referred to as polymerizable compound (C)), and a polymerization initiator (hereinafter, may be referred to as polymerization initiator (D)). The colored curable resin composition of the present invention may further contain a solvent (hereinafter, may be referred to as solvent (E)). The colored curable resin composition of the present invention may further contain a polymerization initiation aid (hereinafter, may be referred to as polymerization initiation aid (D1)). The colored curable resin composition of the present invention may further contain a leveling agent (hereinafter, may be referred to as leveling agent (F)). In this specification, the compounds exemplified as each component may be used alone or in combination of two or more kinds, unless otherwise specified.

[0009] <Colorant (A)> The colorant (A) contains a benzoperylene compound. The benzoperylene compound refers to a compound in which any substituent is bonded to 1,12-benzoperylene, and is preferably a compound in which a substituent having a carbonyl group is bonded to the 3rd, 4th and 9th, 10th positions. The carbonyl groups of the substituents at the 3rd and 4th positions are preferably bonded via an oxygen atom to form a lactone ring, or bonded via a nitrogen atom to form an imide ring. The carbonyl groups of the substituents at the 9th and 10th positions are also preferably bonded via an oxygen atom to form a lactone ring, or bonded via a nitrogen atom to form an imide ring. The benzoperylene compound is particularly preferably a compound represented by formula (I) (hereinafter, sometimes referred to as compound (I)).

[0010] <<Compound (I)>> [ka] [In formula (I), R 1 and R 2 represent, independently of each other, a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent (A1), an aromatic heterocyclic group having 1 to 30 carbon atoms which may have a substituent (A1), or a group in which the hydrocarbon group which may have a substituent (A1) and the aromatic heterocyclic group which may have a substituent (A1) are bonded together. R 3 ~R 10 are, independently of each other, a hydrogen atom, *-R 11 , *-OR 11 , *-CO-OR 11 , a halogen atom, a hydroxy group, a carboxy group or a nitro group. R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 7 and R 8 , R 8 and R 9 and R 9 and R 10 are each independently *-CO-O-CO-* or *-CO-N(R 11)-CO-* may form a ring. R 11 represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent (A1), R 11 When there are multiple, they may be different from each other. * represents a bond.]

[0011] R 1 , R 2 and R 11 Examples of the hydrocarbon group having 1 to 30 carbon atoms represented by the formula (1) include an aliphatic hydrocarbon group and an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or alicyclic.

[0012] R 1 , R 2 and R 11Examples of the saturated or unsaturated chain hydrocarbon group represented by the formula (I) include linear alkyl groups such as a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, a tetradecyl group, a pentadecyl group, a hexadecyl group, a heptadecyl group, an octadecyl group, a nonadecyl group, and an icosyl group; an isopropyl group, a (1-ethyl)propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a (1-ethyl)butyl group, a (2-ethyl)butyl group, a (1-propyl)butyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a (2-methyl)pentyl group, a (1-ethyl)pentyl group, a (3-ethyl)pentyl group, a (1-propyl)pentyl group, a (1-butyl)pentyl group, and the like. hexyl, isohexyl, (2-methyl)hexyl, (5-methyl)hexyl, (2-ethyl)hexyl, (1-butyl)hexyl, (1-pentyl)hexyl, (2-methyl)heptyl, (2-ethyl)heptyl, (3-ethyl)heptyl, (1-hexyl)heptyl, (2-methyl)octyl, (2-ethyl)octyl, (1-heptyl)octyl Examples of the branched alkyl groups include vinyl, 1-propenyl, 2-propenyl (allyl), (1-methyl)ethenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, (1-(2-propenyl))ethenyl, (1,2-dimethyl)propenyl, and 2-pentenyl. The number of carbon atoms in the saturated chain hydrocarbon group is preferably 1 to 25, more preferably 1 to 20, and even more preferably 1 to 18. The number of carbon atoms in the unsaturated chain hydrocarbon group is preferably 2 to 25, more preferably 2 to 20, and even more preferably 2 to 18.

[0013] R 1 , R 2 and R 11Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by the formula (1) include cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, and cyclooctyl group; cycloalkenyl groups such as cyclohexenyl group (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl group, and cyclooctenyl group; norbornyl group, adamantyl group, and bicyclo[2.2.2]octyl group. The number of carbon atoms in the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 25, more preferably 3 to 20, and even more preferably 3 to 15.

[0014] R 1 , R 2 and R 11 Examples of the aromatic hydrocarbon group represented by the formula (I) include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a phenanthryl group, an anthryl group, a pyrenyl group, etc. The aromatic hydrocarbon group preferably has 6 to 25 carbon atoms, more preferably 6 to 20 carbon atoms, and further preferably 6 to 15 carbon atoms.

[0015] R 1 , R 2 and R 11The hydrocarbon group represented by the formula (I) may be a group obtained by combining two or more of the chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups listed above, so long as the upper limit of the carbon number is not more than 30. Such a group may be, for example, a group obtained by combining an aromatic hydrocarbon group with at least one group selected from a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group, and in such a combined hydrocarbon group, the chain hydrocarbon group may be combined as a divalent group (for example, an alkanediyl group).Examples of the combined hydrocarbon groups include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl; arylalkenyl groups such as phenylethenyl (phenylvinyl); arylalkynyl groups such as phenylethynyl; o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 4,6-dimethylphenyl, 5,7-dimethylphenyl, 6,8-dimethylphenyl, 7,9-dimethylphenyl, 8,10-dimethylphenyl, 9,11-dimethylphenyl, 9,12-dimethylphenyl, 9,13-dimethylphenyl, 9,14-dimethylphenyl, 9,15-dimethylphenyl, 9,16-dimethylphenyl, 9,17-dimethylphenyl, 9,18-dimethylphenyl, 9,19-dimethylphenyl, 10,11-dimethylphenyl, 10,12-dimethylphenyl, 10,13-dimethylphenyl, 14,14-dimethylphenyl, 15,15-dimethylphenyl, 16,16-dimethylphenyl, 17,17-dimethylphenyl, 18,18-dimethylphenyl, 19,19-dimethylphenyl, 19,19-dimethylphenyl, 20,11-dimethylphenyl, 21,21-dimethylphenyl, 22,22-dimethylphenyl, 23,23-dimethylphenyl, 24,25-dimethylphenyl, 26,26-dimethylphenyl, 27,28-dimethylphenyl, 29,29-dimethylphenyl, 30,21-dimethylphenyl, 31,22-dimethylphenyl, 32,23-dimethylphenyl, 33,24-dimethylphenyl, 34,25-dimethylphenyl, 35,26-dimethylphenyl, ,5-dimethylphenyl group, 4-vinylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, 2,3-diisopropylphenyl group, 2,4-diisopropylphenyl group, 2,5-diisopropylphenyl group, 2,6-diisopropylphenyl group, 2,4,6-triisopropylphenyl group, 4-butylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, 2,6-di(tert-butyl)phenyl group, 3,5- Alkylaryl groups such as di(tert-butyl)phenyl group, 3,6-di(tert-butyl)phenyl group, 4-tert-butyl-2,6-dimethylphenyl group, 4-pentylphenyl group, 4-octylphenyl group, 4-(2,4,4-trimethyl-2-pentyl)phenyl group, 2-dodecylphenyl group, 3-dodecylphenyl group, and 4-dodecylphenyl group; 2,3-dihydro-4-indenyl group, 1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 8-methyl-1,2,3,5,6,7-hexahydro-4- Examples of the aryl group include an aryl group having an alkanediyl group bonded thereto, such as an s-indacenyl group, a 5,6,7,8-tetrahydro-1-naphthyl group, a 5,6,7,8-tetrahydro-2-naphthyl group, a 3-methyl-5,6,7,8-tetrahydro-2-naphthyl group, or a 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl group; an aryl group having one or more aryl groups bonded thereto, such as a biphenylyl group or a terphenylyl group; a cyclohexylmethylphenyl group, a benzylphenyl group, or a (dimethyl(phenyl)methyl)phenyl group.The hydrocarbon group may be, for example, a hydrocarbon group formed by combining a chain hydrocarbon group and an alicyclic hydrocarbon group, and examples thereof include a 1-methylcyclopropyl group, a 1-methylcyclohexyl group, a 2-methylcyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 1,2-dimethylcyclohexyl group, a 1,3-dimethylcyclohexyl group, a 1,4-dimethylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 2,4-dimethylcyclohexyl group, a 2,5-dimethylcyclohexyl group, a 2,6-dimethylcyclohexyl group, a 3,4-dimethylcyclohexyl group, a 3,5-dimethylcyclohexyl group, a 2,2-dimethylcyclohexyl group, a 3,3-dimethyl ...5-methylcyclohexyl group, a 6-methylcyclohexyl group, a 7-methylcyclohexyl group, a 8-methylcyclohexyl group, a 9-methylcyclohexyl group, a 10-methylcyclohexyl group, a 11-methylcyclopropyl group, a 12-methylcyclohexyl group, a 13-methylcyclohexyl group, a 14-methylcyclohexyl group, a 15-methylcyclohexyl group, a 16-methylcyclohexyl group, a 17-methylcyclohexyl group, a 18-methylcyclohexyl group cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane, cyclohexane,

[0016] R 1 and R 2 Examples of the aromatic heterocyclic group having 1 to 30 carbon atoms and represented by the formula (I) include aromatic heterocyclic groups containing at least one heteroatom such as a nitrogen atom, an oxygen atom, a sulfur atom, etc. Specific examples of the aromatic heterocyclic group include a furyl group, a pyrrolyl group, a thienyl group, an oxazolyl group, a pyridyl group, a quinolinyl group, a thiazolyl group, a benzothiazolyl group, a carbazolyl group, etc., and the number of carbon atoms is preferably 2 to 20, and more preferably 3 to 15.

[0017] R1 and R 2 The group formed by bonding the hydrocarbon group represented by the formula (I) and the aromatic heterocyclic group may be a group formed by bonding two or more of the above-listed hydrocarbon groups and aromatic heterocyclic groups, for example, a group formed by bonding at least one selected from a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group to an aromatic heterocyclic group, and in the group formed by bonding, the chain hydrocarbon group may be bonded as a divalent group (for example, an alkanediyl group). Examples of the group formed by bonding the hydrocarbon group and the aromatic heterocyclic group include a 2-methylpyridinyl group, a 4-ethyl-2-methylpyridinyl group, an indole group, a benzimidazole group, a benzofuran group, and a benzothiophene group. The number of carbon atoms in the group formed by bonding the hydrocarbon group and the aromatic heterocyclic group is preferably 7 to 30, more preferably 8 to 30, and even more preferably 10 to 30.

[0018] R 1 , R 2 and R 11 and R 1 and R 2Examples of the substituent (A1) which the aromatic heterocyclic group having 1 to 30 carbon atoms represented by the formula (1) may have include a halogen atom, a nitrile group, a nitro group, an amino group, a hydroxy group, an alkoxy group having 1 to 20 carbon atoms, such as a methoxy group or an ethoxy group, an aryloxy group having 6 to 20 carbon atoms, such as a phenyloxy group, a 1-naphthyloxy group or a 2-naphthyloxy group, a thiol group, an alkylthio group having 1 to 20 carbon atoms, such as a methylthio group or an ethylthio group, an allylthio group, an arylthio group having 6 to 20 carbon atoms, such as a phenylthio group, a 1-naphthylthio group or a 2-naphthylthio group, a sulfoxy group, an alkylsulfoxy group having 1 to 20 carbon atoms, such as a methylsulfoxy group or an ethylsulfoxy group, an arylsulfoxy group having 6 to 20 carbon atoms, such as a phenylsulfoxy group, a 1-naphthylsulfoxy group or a 2-naphthylsulfoxy group, a silyl group, a boryl group, a monomethylamino group, alkylamino groups having 1 to 20 carbon atoms, such as a dimethylamino group, a trimethylamino group, a monoethylamino group, a diethylamino group, or a triethylamino group; arylamino groups having 6 to 20 carbon atoms, such as a monophenylamino group, a diphenylamino group, or a triphenylamino group; aralkylamino groups having 7 to 20 carbon atoms, such as a benzylamino group; a carboxy group; a carbamoyl group; alkylcarbonyl groups having 2 to 20 carbon atoms, such as an acetyl group, or a propionyl group; arylcarbonyl groups having 7 to 20 carbon atoms, such as a benzoyl group, a 1-naphthylcarbonyl group, or a 2-naphthylcarbonyl group; alkoxycarbonyl groups having 2 to 20 carbon atoms, such as a methoxycarbonyl group, or an ethoxycarbonyl group; and aryloxycarbonyl groups having 7 to 20 carbon atoms, such as a phenyloxycarbonyl group, a 1-naphthyloxycarbonyl group, or a 2-naphthyloxycarbonyl group.

[0019] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of synthesis, a chlorine atom and a bromine atom are preferred, and a bromine atom is more preferred.

[0020] R 1 , R 2 and R 11 Examples of the group include groups represented by the following formulae (D-1) to (D-47) and (G-1) to (G-22), in which * represents a bond.

[0021] [ka]

[0022] [ka]

[0023] R 1 and R 2 are preferably, independently of each other, a saturated chain hydrocarbon group which may have a substituent (A1), an aromatic hydrocarbon group which may have a substituent (A1), or a group in which an aromatic hydrocarbon group which may have a substituent (A1) and a chain hydrocarbon group are combined. From the viewpoint of improving the solubility of compound (I) in a solvent, the saturated chain hydrocarbon group is preferably a saturated branched chain hydrocarbon group. The saturated chain hydrocarbon group (preferably a saturated branched chain hydrocarbon group) may have a carbon number of 1 to 30, preferably 1 to 20, and more preferably 3 to 15. The aromatic hydrocarbon group or the group in which an aromatic hydrocarbon group and a chain hydrocarbon group are combined preferably has a carbon number of 6 to 20, more preferably 6 to 15, and even more preferably 8 to 15. From the viewpoint of improving the fluorescence intensity of the obtained color filter, R 1 and R 2 is more preferably a group represented by the above formulas (D-4) to (D-14) or (G-5) to (G-22), further preferably a group represented by any of formulas (D-4) to (D-14), (G-5), (G-7), (G-8), (G-11) to (G-13), (G-15), (G-16), (G-19), (G-21), or (G-22), and particularly preferably a group represented by any of formulas (D-4) to (D-14), (G-7), (G-11), (G-13), (G-15), or (G-16). Also, R 1 and R 2 are preferably the same group.

[0024] R 11The carbon number of the saturated chain hydrocarbon group may be 1 to 30, preferably 1 to 25, more preferably 1 to 20, even more preferably 1 to 18, and even more preferably 3 to 15. The carbon number of the saturated chain hydrocarbon group or the group combining the alicyclic hydrocarbon group and the chain hydrocarbon group is preferably 3 to 20, more preferably 6 to 20, and even more preferably 6 to 15. The carbon number of the aromatic hydrocarbon group or the group combining the aromatic hydrocarbon group and the chain hydrocarbon group is preferably 6 to 20, more preferably 7 to 20, even more preferably 8 to 20, and even more preferably 10 to 20. The carbon number of the aromatic hydrocarbon group or the group combining the aromatic hydrocarbon group and the chain hydrocarbon group is preferably 6 to 20, more preferably 7 to 20, even more preferably 8 to 20, and even more preferably 10 to 20. From the viewpoint of improving the solubility of compound (I) in a solvent, R 11 is preferably a group represented by the above formulae (D-4) to (D-31), (D-34) to (D-46), (G-1), or (G-5) to (G-22), more preferably a group represented by the formulae (D-4) to (D-14), or (G-5) to (G-22), still more preferably a group represented by any of the formulae (D-4) to (D-14), (G-5), (G-7), (G-8), (G-11) to (G-13), (G-15), (G-16), (G-19), (G-21), or (G-22), and particularly preferably a group represented by any of the formulae (D-4) to (D-14), (G-7), (G-11), (G-13), (G-15), or (G-16). Also, R 1 and R 2 are the same group, R 11 is R 1 and R 2 It is preferable that the group is different from the group.

[0025] R 3 ~R 10Represented by *-OR 11 As for the above R 11 Examples of the oxy group include an alkoxy group having 1 to 30 carbon atoms and an aryloxy group having 1 to 30 carbon atoms. 11 Specific examples of the aryl group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a phenoxy group, and a naphthyloxy group.

[0026] R 3 ~R 10 Represented by *-CO-OR 11 As for the above R 11 Examples of the alkyl group include an alkoxycarbonyl group having 1 to 30 carbon atoms and an aryloxycarbonyl group having 1 to 30 carbon atoms. 11 R has 11 is preferably a saturated chain hydrocarbon group, a saturated alicyclic hydrocarbon group, a group combining an alicyclic hydrocarbon group with a chain hydrocarbon group, an aromatic hydrocarbon group, or a group combining an aromatic hydrocarbon group with a chain hydrocarbon group, more preferably a saturated chain hydrocarbon group having 1 to 20 carbon atoms, a saturated alicyclic hydrocarbon group having 3 to 15 carbon atoms, a group combining an alicyclic hydrocarbon group having 4 to 15 carbon atoms with a chain hydrocarbon group, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a group combining an aromatic hydrocarbon group having 7 to 20 carbon atoms with a chain hydrocarbon group, and even more preferably a saturated chain hydrocarbon group having 3 to 18 carbon atoms, a group combining an alicyclic hydrocarbon group having 4 to 10 carbon atoms with a chain hydrocarbon group, or a group combining an aromatic hydrocarbon group having 7 to 15 carbon atoms with a chain hydrocarbon group. 11Specific examples of the aryloxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a sec-butoxycarbonyl group, a tert-butoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, a (1-ethyl)pentyloxycarbonyl group, a hexyloxycarbonyl group, a (2-ethyl)hexyloxycarbonyl group, a heptyloxycarbonyl group, a (1-butyl)heptyloxycarbonyl group, an octyloxycarbonyl group, a (1-heptyl)octyloxycarbonyl group, a nonyloxycarbonyl group, and the like. Examples of the alkyl group include an oxycarbonyl group, a decyloxycarbonyl group, an undecyloxycarbonyl group, a dodecyloxycarbonyl group, a tridecyloxycarbonyl group, a tetradecyloxycarbonyl group, a pentadecyloxycarbonyl group, a hexadecyloxycarbonyl group, a heptadecyloxycarbonyl group, an octadecyloxycarbonyl group, a phenyloxycarbonyl group, a benzyloxycarbonyl group, a cyclohexyloxycarbonyl group, a cyclohexylmethoxycarbonyl group, and an icosyloxycarbonyl group.

[0027] R 3 ~R 10 Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0028] R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 7 and R 8 , R 8 and R 9 and R 9 and R 10 respectively form *-CO-O-CO-* or *-CO-N(R 11 Examples of rings containing -CO-* (where * represents a bond) include R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 7 and R 8 , R 8and R 9 and R 9 and R 10 are each independently a divalent group represented by the following formulae (H-1) to (H-16). In formulae (H-1) to (H-16), * represents R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 7 and R 8 , R 8 and R 9 or R 9 and R 10 represents a bond to the benzoperylene skeleton.

[0029] [ka]

[0030] Note that the above *-CO-N(R 11 )-CO-* containing ring has R 11 As the substituent (A1), it is preferable that it is a saturated chain hydrocarbon group which may have a substituent (A1), an aromatic hydrocarbon group which may have a substituent (A1), or a group in which an aromatic hydrocarbon group which may have a substituent (A1) and a chain hydrocarbon group are combined, it is more preferable that it is a saturated chain hydrocarbon group having 3 to 20 carbon atoms which may have a substituent (A1), an aromatic hydrocarbon group having 6 to 15 carbon atoms which may have a substituent (A1), or a group in which an aromatic hydrocarbon group having 7 to 20 carbon atoms which may have a substituent (A1) and a chain hydrocarbon group are combined, it is even more preferable that it is a saturated chain hydrocarbon group having 6 to 18 carbon atoms, or a group in which an aromatic hydrocarbon group having 7 to 18 carbon atoms which may have a substituent (A1) and a chain hydrocarbon group are combined, and from the viewpoint of improving the solubility of the compound (I) in a solvent, it is preferable that the saturated chain hydrocarbon group is a saturated branched chain hydrocarbon group. In addition, the substituent (A1) is preferably a halogen atom (particularly a bromine atom).

[0031] Specific examples of the group represented by formula (H-9) include groups represented by the following formulae (H-9-1) to (H-9-16). In formulae (H-9-1) to (H-9-16), * represents R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 7 and R 8 , R 8 and R 9 or R 9 and R 10 represents a bond to the benzoperylene skeleton.

[0032] [ka]

[0033] R 3 and R 6 ~R 10 is preferably a hydrogen atom. 3 and R 6 ~R 10 may be appropriately combined to form a compound having a desired absorption wavelength or fluorescence wavelength.

[0034] R 4 and R 5 As for the, independently, *-OR 11 OR*-CO-OR 11 or R 4 and R 5 *-CO-O-CO-* or *-CO-N(R 11 It is preferable that the ring contains -CO-*. 11 OR*-CO-OR 11From the viewpoint of improving the solubility of compound (I) in a solvent and improving the fluorescence intensity of the resulting color filter, R is more preferably an alkoxy group having 1 to 20 carbon atoms, an alkoxycarbonyl group having 1 to 20 carbon atoms, or an aryloxycarbonyl group having 6 to 20 carbon atoms, even more preferably an alkoxy group having 1 to 15 carbon atoms, an alkoxycarbonyl group having 1 to 15 carbon atoms, or an aryloxycarbonyl group having 7 to 15 carbon atoms, even more preferably an alkoxy group having 1 to 10 carbon atoms or an alkoxycarbonyl group having 1 to 10 carbon atoms, and particularly preferably an alkoxycarbonyl group having 1 to 10 carbon atoms. 4 and R 5 *-CO-O-CO-* or *-CO-N(R 11 )-CO-*, R 4 and R 5 More preferably, the group represented by the above formula (H-1) to (H-3) or (H-9) to (H-11) is formed, and further preferably, the group represented by the above formula (H-1) to (H-3) or (H-9-1) to (H-9-16) is formed. From the viewpoint of improving the solubility of compound (I) in a solvent and improving the fluorescence intensity of the resulting color filter, it is particularly preferable that the group represented by any one of formulas (H-1), (H-9-5), (H-9-6), (H-9-9), (H-9-11), (H-9-12) and (H-9-14) to (H-9-16) is formed.

[0035] Specific examples of compound (I) include compounds (I-1) to (I-87) shown in Tables 1 to 3 below.

[0036] [Table 1]

[0037] [Table 2]

[0038] [Table 3]

[0039] In Tables 1 to 3, H represents a hydrogen atom, D-6, D-13, G-7, H-1, H-9-6, H-9-9, H-9-11, H-9-12, H-9-14, H-9-15, and H-9-16 represent groups represented by the above formulas (D-6), (D-13), (G-7), (H-1), (H-9-6), (H-9-9), (H-9-11), (H-9-12), (H-9-14), (H-9-15), and (H-9-16), respectively, and F-1 to F-21 represent groups represented by the following formulas (F-1) to (F-21), respectively. In the formulas, * represents a bond.

[0040] [ka]

[0041] As the compound (I), from the viewpoint of improving the solubility of the compound (I) in a solvent and improving the fluorescence intensity of the resulting color filter, the compounds (I-2), (I-3), (I-9), (I-10), (I-12), (I-13), (I-19) to (I-31), (I-34) to (I-50), (I-53) to (I-69), or (I-72) to (I-87) are preferred. Compounds (I-3), (I-9), (I-12), (I-13), (I-21) to (I-30), (I-69), or (I-72) to (I-87) are more preferred, and compounds (I-3), (I-9), (I-12), (I-13), (I-21) to (I-30), (I-69), (I-72) to (I-83), (I-85), or (I-87) are even more preferred.

[0042] Compound (I) is preferably a compound represented by formula (Ia).

[0043] <<Compound represented by formula (Ia)>> [ka] [In formula (Ia), R 1a and R 2aeach independently represents an aryl group having 6 to 20 carbon atoms which may have a substituent (A2) or a heteroaryl group having 1 to 20 carbon atoms which may have a substituent (A2). R 3a , R 6a , R 7a , R 8a , R 9a and R 10a are each independently a hydrogen atom, *-R 11a , *-OR 11a , *-CO-OR 11a , a halogen atom, a hydroxy group, a carboxy group or a nitro group. R 11a represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (A1), R 11a When there are multiple, they may be different from each other. R 4a and R 5a are, independently of each other, *-CO-OR 11a or R 4a and R 5a are bonded to form a group represented by formula (a) or formula (b). [ka] [In formulas (a) and (b), R b1 and R b2 each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (A1). R c1 represents an aryl group having 6 to 20 carbon atoms and having a substituent (A2).] R 4a and R 5a is a group represented by formula (b), R 1a , R 2a and R c1 The above three do not have the same base. * represents a bond.]

[0044] R 1a , R 2a and R c1Examples of the aryl group having 6 to 20 carbon atoms represented by the formula (I) include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a phenanthryl group, an anthryl group, and a pyrenyl group. The aryl group having 6 to 18 carbon atoms is preferable, and the number of carbon atoms is more preferably 6 to 15.

[0045] R 1a and R 2a Examples of the heteroaryl group having 1 to 20 carbon atoms represented by the formula (I) include a furyl group, a pyrrolyl group, a thienyl group, an oxazolyl group, a pyridyl group, a quinolinyl group, a thiazolyl group, a benzothiazolyl group, and a carbazolyl group, and the number of carbon atoms is preferably 2 to 20, and more preferably 3 to 15.

[0046] R 1a , R 2a and R c1 and an aryl group having 6 to 20 carbon atoms represented by the formula: 1a and R 2aExamples of the substituent (A2) which the heteroaryl group having 1 to 20 carbon atoms represented by the formula (1) may have include a halogen atom, a nitrile group, a nitro group, an amino group, a hydroxy group, an alkyl group having 1 to 20 carbon atoms, such as a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, etc., a cycloalkyl group having 3 to 20 carbon atoms, such as a cyclopropyl group, a cyclobutyl group, etc., an alkenyl group having 2 to 20 carbon atoms, such as a vinyl group, a 1-propenyl group, etc., an aryl group having 6 to 20 carbon atoms, such as a phenyl group, a 1-naphthyl group, etc., an aralkyl group having 7 to 20 carbon atoms, such as a benzyl group, a phenethyl group, etc. Arylalkenyl groups having 8 to 20 carbon atoms, such as a phenylethenyl group (phenylvinyl group); alkoxy groups having 1 to 20 carbon atoms, such as a methoxy group and an ethoxy group; aryloxy groups having 6 to 20 carbon atoms, such as a phenyloxy group, a 1-naphthyloxy group and a 2-naphthyloxy group; thiol groups; alkylthio groups having 1 to 20 carbon atoms, such as a methylthio group and an ethylthio group; allylthio groups; arylthio groups having 6 to 20 carbon atoms, such as a phenylthio group, a 1-naphthylthio group and a 2-naphthylthio group; sulfoxy groups; alkylsulfoxy groups; arylsulfoxy groups having 6 to 20 carbon atoms, such as a phenylsulfoxy group, a 1-naphthylsulfoxy group, or a 2-naphthylsulfoxy group; silyl groups; boryl groups; alkylamino groups having 1 to 20 carbon atoms, such as a monomethylamino group, a dimethylamino group, a trimethylamino group, a monoethylamino group, a diethylamino group, or a triethylamino group; arylamino groups having 6 to 20 carbon atoms, such as a monophenylamino group, a diphenylamino group, or a triphenylamino group; aralkylamino groups having 7 to 20 carbon atoms, such as a benzylamino group; a carboxy group; moyl group; alkylcarbonyl groups having 2 to 20 carbon atoms, such as an acetyl group or a propionyl group; arylcarbonyl groups having 7 to 20 carbon atoms, such as a benzoyl group, a 1-naphthylcarbonyl group or a 2-naphthylcarbonyl group; alkoxycarbonyl groups having 2 to 20 carbon atoms, such as a methoxycarbonyl group or an ethoxycarbonyl group; aryloxycarbonyl groups having 7 to 20 carbon atoms, such as a phenyloxycarbonyl group, a 1-naphthyloxycarbonyl group or a 2-naphthyloxycarbonyl group; heterocyclic groups having 1 to 20 carbon atoms, such as a furyl group, a pyrrolyl group or a thienyl group; an acetylene group;and an alkanediyl group having 1 to 20 carbon atoms which forms a ring together with at least two carbon atoms in the aryl group.

[0047] Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. From the viewpoint of synthesis, a chlorine atom and a bromine atom are preferred, and a bromine atom is more preferred.

[0048] R 1a and R 2a are preferably, each independently, an aryl group which may have a substituent (A2). The number of carbon atoms in the aryl group is preferably 6 to 15, more preferably 6 to 10, and the aryl group is particularly preferably a phenyl group. Also, R 1a and R 2a are preferably the same group.

[0049] R 1a and R 2a The aryl group having 6 to 20 carbon atoms and the heteroaryl group having 1 to 20 carbon atoms represented by the following formula (I) preferably have a substituent (A2). The substituent (A2) is preferably an alkyl group having 1 to 20 carbon atoms or a halogen atom, more preferably an alkyl group having 1 to 10 carbon atoms or a halogen atom, still more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably an alkyl group having 1 to 4 carbon atoms.

[0050] R 1a and R 2a When the aryl group having 6 to 20 carbon atoms and the heteroaryl group having 1 to 20 carbon atoms represented by the formula (I) have a substituent (A2), the number of the substituents (A2) is not limited and may be one or more, preferably two to four, and more preferably two from the viewpoint of improving the fluorescence intensity of the obtained color filter. The substituent (A2) is preferably located at at least one ortho position, and more preferably located at two ortho positions.

[0051] R 1a and R 2aWhen the aryl group having 6 to 20 carbon atoms and the heteroaryl group having 1 to 20 carbon atoms represented by the following formula (I) have a plurality of substituents (A2), they may be the same group or different groups.

[0052] R c1 The number of carbon atoms in the aryl group which may have a substituent (A2) represented by the following formula is preferably 6 to 15, more preferably 6 to 10, and the aryl group is particularly preferably a phenyl group.

[0053] R c1 The aryl group having 6 to 20 carbon atoms and represented by the formula (I) preferably has a substituent (A2). The substituent (A2) is preferably an alkyl group having 1 to 20 carbon atoms, a halogen atom, or an alkanediyl group having 1 to 20 carbon atoms which forms a ring together with at least two carbon atoms in the aryl group, and more preferably an alkyl group having 1 to 10 carbon atoms, a halogen atom, or an alkanediyl group having 1 to 10 carbon atoms which forms a ring together with at least two carbon atoms in the aryl group. Also, R c1 The aryl group having 6 to 20 carbon atoms, represented by the formula (I), preferably has at least one substituent (A2) which is either an alkyl group having 4 to 20 carbon atoms, a halogen atom, or an alkanediyl group having 1 to 20 carbon atoms forming a ring together with at least two carbon atoms in the aryl group.

[0054] R c1 When the aryl group having 6 to 20 carbon atoms represented by the following formula (1) has a substituent (A2), the number of the substituents (A2) is not limited and may be one or more, and is preferably one to three.

[0055] R c1 When the aryl group having 6 to 20 carbon atoms represented by the following formula (1) has a plurality of substituents (A2), they may be the same group or different groups.

[0056] R 11a , R b1 and R b2The hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) is, except that the hydrocarbon group having 21 or more carbon atoms is not included. 1 , R 2 and R 11 Examples of the hydrocarbon group include the same as those of the hydrocarbon group represented by the following formula:

[0057] R 11a , R b1 and R b2 The substituent (A1) which may be possessed by the hydrocarbon group having 1 to 20 carbon atoms represented by the formula: 1 , R 2 and R 11 Examples of the substituents are the same as those of the substituent (A1) which may be possessed by the hydrocarbon group having 1 to 30 carbon atoms and represented by the following formula:

[0058] R 11a As the alkyl group, a saturated aliphatic hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (A1), an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent (A1), or a group in which an aromatic hydrocarbon group having 7 to 20 carbon atoms which may have a substituent (A1) and a chain-like hydrocarbon group are preferred, a saturated chain-like hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (A1), a group in which a saturated alicyclic hydrocarbon group having 4 to 20 carbon atoms which may have a substituent (A1) and a chain-like hydrocarbon group, or a group in which an aromatic hydrocarbon group having 7 to 20 carbon atoms which may have a substituent (A1) and a chain-like hydrocarbon group are more preferred, and a saturated chain-like hydrocarbon group having 3 to 18 carbon atoms which may have a substituent (A1) is more preferred. R is more preferably a chain hydrocarbon group, a group in which a saturated alicyclic hydrocarbon group having 4 to 15 carbon atoms which may have a substituent (A1) is combined with a chain hydrocarbon group, or a group in which an aromatic hydrocarbon group having 7 to 15 carbon atoms which may have a substituent (A1) is combined with a chain hydrocarbon group, and even more preferably a branched alkyl group having 3 to 15 carbon atoms which may have a substituent (A1), a straight-chain alkyl group having 4 to 18 carbon atoms which may have a substituent (A1), a group in which a saturated alicyclic hydrocarbon group having 6 to 15 carbon atoms which may have a substituent (A1) is combined with a chain hydrocarbon group, or a group in which an aromatic hydrocarbon group having 7 to 15 carbon atoms which may have a substituent (A1) is combined with a chain hydrocarbon group.11a Specifically, the groups represented by the above formulas (D-4) to (D-31) or (D-34) to (D-46) are preferred.

[0059] R b1 and R b2 are preferably each independently a saturated chain hydrocarbon group which may have a substituent (A1), a saturated alicyclic hydrocarbon group which may have a substituent (A1), or a group which combines a chain hydrocarbon group which may have a substituent (A1) and an alicyclic hydrocarbon group, and more preferably a saturated chain hydrocarbon group which may have a substituent (A1). The saturated chain hydrocarbon group is preferably a saturated straight chain hydrocarbon group, and the number of carbon atoms in the saturated chain hydrocarbon group (preferably a saturated straight chain hydrocarbon group) may be 1 to 20, preferably 3 to 20, more preferably 3 to 15, and even more preferably 3 to 10. Also, R b1 and R b2 is preferably a group in which the total number of carbon atoms contained in the two groups is 6 or more.

[0060] R b1 and R b2 are preferably the same group.

[0061] R 3a , R 6a , R 7a , R 8a , R 9a and R 10a Represented by *-OR 11a As for R 3 ~R 10 Represented by *-OR 11 The same example can be given.

[0062] R 3a ~R 10a Represented by *-CO-OR 11a As for R 3 ~R 10 Represented by *-CO-OR 11 The same example can be given.

[0063] R 3a , R 6a , R 7a , R 8a , R 9a and R 10a The halogen atom represented by the formula R 3 ~R 10 Examples are the same as those of halogen atoms represented by the following formula:

[0064] R 3a , R 6a , R 7a , R 8a , R 9a and R 10a From the viewpoint of synthesis, R is preferably a hydrogen atom. 3a , R 6a , R 7a , R 8a , R 9a and R 10a may be appropriately combined to form a compound having a desired absorption wavelength or fluorescence wavelength.

[0065] R 4a and R 5a Specific examples of the group represented by formula (a) to which is bonded include groups represented by the above formulae (H-9-5) and (H-9-6).

[0066] R 4a and R 5a Specific examples of the group represented by formula (b) to which is bonded include the groups represented by the above formulae (H-9-10) to (H-9-16).

[0067] Among the compounds (Ia), the compounds represented by formulas (Ii) to (I-iii) are preferred from the viewpoints of improving the fluorescence intensity of the resulting color filter and improving the solubility of the compound (I) in a solvent.

[0068] <<<Compound represented by formula (Ii)>>> [ka] [In formula (Ii), R1i ~R 4i , R 11i , and R 12i each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (A1). R 5i ~R 10i , R 3ai , R 6ai , R 7ai , R 8ai , R 9ai and R 10ai each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (A1), a halogen atom, a hydroxy group, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, a carboxy group, an alkoxycarbonyl group having 2 to 20 carbon atoms, or a nitro group.]

[0069] <<<Compound represented by formula (I-ii)>>> [ka] [In formula (I-ii), R 1i ~R 4i , R b1i , and R b2i each independently represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (A1). R 5i ~R 10i , R 3ai , R 6ai , R 7ai , R 8ai , R 9ai and R 10ai each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (A1), a halogen atom, a hydroxy group, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, a carboxy group, an alkoxycarbonyl group having 2 to 20 carbon atoms, or a nitro group.]

[0070] <<<Compound represented by formula (I-iii)>>> [ka] [In formula (I-iii), Ar 7i ~Ar 9i each independently represents an aryl group having 6 to 20 carbon atoms which may have a substituent (A2), provided that Ar 7 ~Ar 9 The three above cannot all have the same base. R 3ai , R 6ai , R 7ai , R 8ai , R 9ai and R 10ai each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (A1), a halogen atom, a hydroxy group, an alkoxy group having 1 to 20 carbon atoms, an aryloxy group having 6 to 20 carbon atoms, a carboxy group, an alkoxycarbonyl group having 2 to 20 carbon atoms, or a nitro group.]

[0071] In formulae (Ii) to (I-iii), R 1i ~R 12i , R 3ai , R 6ai ~R 10ai , R b1i , and R b2i The hydrocarbon group having 1 to 20 carbon atoms represented by the formula (I) is, except that the hydrocarbon group having 21 or more carbon atoms is not included. 1 , R 2 and R 11 Examples of the hydrocarbon group include the same as those of the hydrocarbon group represented by the following formula:

[0072] R 1i ~R 12i , R 3ai , R 6ai ~R 10ai , R b1i , and R b2i The substituent (A1) which may be possessed by the hydrocarbon group having 1 to 20 carbon atoms represented by the formula: 1 , R 2 and R 11 Examples of the substituents are the same as those of the substituent (A1) which may be possessed by the hydrocarbon group having 1 to 30 carbon atoms and represented by the following formula:

[0073] Ar7i ~Ar 9i The aryl group having 6 to 20 carbon atoms represented by the formula: 1a , R 2a and R c1 Examples of the aryl group include the same as those of the aryl group having 6 to 20 carbon atoms represented by the following formula:

[0074] Ar 7i ~Ar 9i The substituent (A2) which may be possessed by the aryl group having 6 to 20 carbon atoms represented by the following formula (1) is R 1a , R 2a and R c1 Examples of the substituent (A2) that may be possessed by the aryl group having 6 to 20 carbon atoms represented by the following formula are mentioned.

[0075] R 5i ~R 10i , R 3ai , R 6ai , R 7ai , R 8ai , R 9ai and R 10ai The halogen atom represented by the formula R 3 ~R 10 Among them, from the viewpoint of synthesis, a chlorine atom or a bromine atom is preferable.

[0076] R 5i ~R 10i , R 3ai , R 6ai , R 7ai , R 8ai , R 9ai and R 10ai Examples of the alkoxy group having 1 to 20 carbon atoms represented by the formula (I) include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a pentyloxy group.

[0077] R 5i ~R 10i , R 3ai , R 6ai , R 7ai , R 8ai , R 9ai and R 10aiExamples of the aryloxy group having 6 to 20 carbon atoms represented by the following formula include a phenoxy group, a 1-naphthyloxy group, and a 2-naphthyloxy group.

[0078] R 5i ~R 10i , R 3ai , R 6ai , R 7ai , R 8ai , R 9ai and R 10ai Examples of the alkoxycarbonyl group having 2 to 20 carbon atoms represented by the formula (I) include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a sec-butoxycarbonyl group, a tert-butoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, a (1-ethyl)pentyloxycarbonyl group, a hexyloxycarbonyl group, and a (2-ethyl)hexyloxycarbonyl group.

[0079] R 1i ~R 4i are each independently preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms, even more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably an alkyl group having 1 to 4 carbon atoms. R 5i ~R 10i are each preferably, independently, a hydrogen atom or a halogen atom, and more preferably a hydrogen atom. R 3ai , R 6ai ~R 10ai is preferably a hydrogen atom. R 11i , and R 12iare preferably, independently of each other, a saturated aliphatic hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms, or a group in which an aromatic hydrocarbon group having 7 to 20 carbon atoms and a chain hydrocarbon group are combined, more preferably a saturated chain hydrocarbon group having 1 to 20 carbon atoms, a group in which a saturated alicyclic hydrocarbon group having 4 to 20 carbon atoms and a chain hydrocarbon group are combined, or a group in which an aromatic hydrocarbon group having 7 to 20 carbon atoms and a chain hydrocarbon group are combined, a saturated chain hydrocarbon group having 3 to 18 carbon atoms, a group in which a saturated alicyclic hydrocarbon group having 4 to 15 carbon atoms and a chain hydrocarbon group are combined, or More preferably, it is a group in which an aromatic hydrocarbon group having 7 to 15 carbon atoms is combined with a chain-like hydrocarbon group, even more preferably, it is a branched chain alkyl group having 3 to 15 carbon atoms, a linear alkyl group having 4 to 18 carbon atoms, a group in which a saturated alicyclic hydrocarbon group having 6 to 15 carbon atoms is combined with a chain-like hydrocarbon group, or a group in which an aromatic hydrocarbon group having 7 to 15 carbon atoms is combined with a chain-like hydrocarbon group, and particularly preferably, it is a branched chain alkyl group having 3 to 12 carbon atoms, a linear alkyl group having 5 to 18 carbon atoms, or a group in which an aromatic hydrocarbon group having 7 to 12 carbon atoms is combined with a chain-like hydrocarbon group. 11i and R 12i are preferably the same group. R b1i , and R b2i are preferably, independently of each other, a saturated chain hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (A1), a saturated alicyclic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent (A1), or a group combining a chain hydrocarbon group having 4 to 20 carbon atoms and an alicyclic hydrocarbon group which may have a substituent (A1), more preferably a saturated chain hydrocarbon group having 3 to 20 carbon atoms, even more preferably a saturated straight-chain hydrocarbon group having 3 to 20 carbon atoms, even more preferably a saturated straight-chain hydrocarbon group having 3 to 15 carbon atoms, and particularly preferably a saturated straight-chain hydrocarbon group having 3 to 10 carbon atoms. b1i , and R b2i is preferably a group having a total of 6 or more carbon atoms contained in the two groups. b1i , and R b2i are preferably the same group. Ar 7i , and Ar 8i are preferably, independently of each other, an aryl group having 6 to 15 carbon atoms which may have a substituent (A2), more preferably an aryl group having 6 to 10 carbon atoms which may have a substituent (A2), even more preferably a phenyl group which may have a substituent (A2), and even more preferably a phenyl group having a substituent (A2). The substituent (A2) is preferably an alkyl group having 1 to 20 carbon atoms or a halogen atom, more preferably an alkyl group having 1 to 10 carbon atoms or a halogen atom, even more preferably an alkyl group having 1 to 6 carbon atoms, and even more preferably an alkyl group having 1 to 4 carbon atoms. The number of the substituents (A2) is not particularly limited, but is preferably 2 to 4, more preferably 2, and particularly preferably two substituents (A2) are at the ortho position. Also, Ar 7i , and Ar 8i are preferably the same group. Ar 9i is preferably an aryl group having 6 to 15 carbon atoms which may have a substituent (A2), more preferably an aryl group having 6 to 10 carbon atoms which may have a substituent (A2), even more preferably a phenyl group which may have a substituent (A2), and even more preferably a phenyl group having a substituent (A2). The substituent (A2) is preferably an alkyl group having 1 to 20 carbon atoms, a halogen atom, or an alkanediyl group having 1 to 20 carbon atoms which forms a ring together with at least two carbon atoms in the aryl group, and more preferably an alkyl group having 1 to 10 carbon atoms, a halogen atom, or an alkanediyl group having 1 to 10 carbon atoms which forms a ring together with at least two carbon atoms in the aryl group. The number of the substituents (A2) is not particularly limited, but is preferably 1 to 3.

[0080] Compound (I) can be produced, for example, by reacting a compound represented by the following formula (pt1) with maleic anhydride or maleic anhydride imide in the presence of a dehydrogenating agent. 4 and R 5A compound that forms a ring containing *-CO-O-CO-* (* represents a bond) is called compound (I)', and R in compound (I) 4 and R 5 So, *-CO-N(R 11 A compound forming a ring containing -CO-* (* represents a bond) is referred to as compound (I)'''.

[0081] [ka] [In the formula, R 1 ~R 3 and R 6 ~R 11 is the same as defined above.]

[0082] The compound represented by formula (pt1) is, for example, N 1 ,N 2 -Bis(2,6-diisopropylphenyl)perylene-3,4,9,10-tetracarboxylic diimide, N 1 ,N 2 -Bis(3-pentyl)perylene-3,4,9,10-tetracarboxylic diimide, N 1 ,N 2 -bis(3-pentyl)perylene-3,4,9,10-tetracarboxylic diimide and the like.

[0083] The amount of maleic anhydride or maleic anhydride imide used is usually 1 mol or more and 1,000 mol or less, preferably 1 mol or more and 800 mol or less, more preferably 1 mol or more and 600 mol or less, and even more preferably 1 mol or more and 400 mol or less, relative to 1 mol of the compound represented by formula (pt1).

[0084] The dehydrogenation agent is a dehydrogenation agent that removes hydrogen from a 6-membered ring compound to aromaticize the compound. As the dehydrogenation agent, chloranil, p-benzoquinone, 2,5-dichloro-p-quinone, 2,3-dichloro-5,6-dicyano-1,4-benzoquinone, tetramethyl-p-quinone, 2,5-diphenyl-p-quinone, and bromanil are preferred, and chloranil and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone are more preferred.

[0085] The reaction temperature is usually from -100°C to 300°C.

[0086] In addition, R in compound (I) 4 and R 5 However, independently of each other, *-CO-OR 11a The compound represented by (* represents a bond) (hereinafter, sometimes referred to as compound (I)'') can be produced, for example, by reacting compound (I)' with compounds represented by formulae (MA1-1) and (MA1-2) in a solvent.

[0087] In addition to the above-mentioned production method, compound (I)''' can be produced, for example, by reacting compound (I)' with a compound represented by formula (MA2) in a solvent.

[0088] X in the compound represented by formula (MA1-1) represents a halogen atom, preferably a chlorine atom or a bromine atom. The compound represented by formula (MA1-1) may be used alone or in combination of two or more kinds, and the compound represented by formula (MA1-2) may be used alone or in combination of two or more kinds.

[0089] The total amount of the compounds represented by formula (MA1-1) and formula (MA1-2) used is usually 1 mol or more and 20 mol or less, preferably 1 mol or more and 15 mol or less, and more preferably 1 mol or more and 10 mol or less, per mol of compound (I)'.

[0090] The amount of the compound represented by formula (MA2) used is usually 1 mol or more and 10 mol or less, preferably 1 mol or more and 8 mol or less, more preferably 1 mol or more and 6 mol or less, and even more preferably 1 mol or more and 4 mol or less, relative to 1 mol of compound (I)'.

[0091] Examples of the solvent include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; ether solvents such as diethyl ether and tetrahydrofuran; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1,2-dichlorobenzene; amide solvents such as N,N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid; and imidazole.

[0092] The amount of the solvent used is usually 1 to 1,000 parts by mass per part by mass of compound (I)', whether compound (I)'' or compound (I)''' is produced.

[0093] The reaction temperature is usually from -100°C to 300°C, whether compound (I)'' or compound (I)''' is produced.

[0094] After the reaction is completed, the method for extracting compound (I)', compound (I)'', or compound (I)''', is not particularly limited, and can be extracted by various known methods. After extraction, the resulting residue may be purified by column chromatography, recrystallization, or the like. The chemical structure of the obtained compound can be analyzed by known analytical methods and conditions. Such analytical methods include, but are not limited to, X-ray crystal structure analysis, mass spectrometry (LC), NMR analysis, and elemental analysis. X-ray crystal structure analysis can be performed, for example, in accordance with Chemistry of Materials, 2012, Vol. 24, p. 4647-4652.

[0095] Benzoperylene compounds have high solubility in solvents such as propylene glycol monomethyl ether acetate and cyclohexanone (particularly propylene glycol monomethyl ether acetate), and have good solubility. The solubility can be calculated by weighing out about 50 mg of the compound to be measured for solubility (hereinafter sometimes referred to as solute) in a 20 mL screw tube, adding about 500 mg of solvent thereto, weighing the total amount of solute and solvent, and stirring with a mix rotor for 30 minutes. If dissolution is confirmed by visual observation, the solubility can be calculated from the mass of the solute relative to the total mass of the solute and solvent according to the following formula (h). If dissolution is not confirmed by visual observation, the solvent is added in 500 mg increments until dissolution occurs, and each time it is added, the mixture is stirred with a mix rotor for 30 minutes. The solubility can be calculated from the mass of the solute relative to the total mass of the solute and solvent when dissolution is confirmed by visual observation according to the following formula (h). Solubility (%) = (mass of solute) / (total mass of solute and solvent) x 100 (h)

[0096] The solubility of the benzoperylene compound in propylene glycol monomethyl ether acetate at 20°C is preferably 0.5% by mass or more, more preferably 0.8% by mass or more, and even more preferably 1.0% by mass or more, and may be 15% by mass or less.

[0097] From the viewpoint of improving the fluorescence intensity of the resulting color filter, the content of the benzoperylene compound may be 100 mass% in the total amount of the colorant (A), and the lower limit may be, for example, 0.1 mass% or more, preferably 5 mass% or more, more preferably 10 mass% or more, even more preferably 15 mass% or more, and even more preferably 20 mass% or more.

[0098] The benzoperylene compound is superior in fluorescence intensity and the retention rate of the fluorescence intensity after a heat resistance test, compared with the perylene compound used in the conventional colored curable resin composition. Therefore, the color filter formed from the colored curable resin composition containing the benzoperylene compound tends to have high fluorescence intensity and excellent brightness. The retention rate of the fluorescence intensity after a heat resistance test can be measured by subjecting the color filter formed from the colored curable resin composition to a heating test, and measuring the retention rate of the fluorescence intensity before and after the test. As the measurement condition, for example, a method of holding the color filter at about 200 to 250°C for 2 to 6 hours can be mentioned.

[0099] The colorant (A) may further contain a perylene compound. The perylene compound is preferably a compound having a substituent having a carbonyl group bonded to the 3rd, 4th and 9th, 10th positions. The carbonyl groups of the substituents at the 3rd and 4th positions are preferably bonded via an oxygen atom to form a lactone ring, or bonded via a nitrogen atom to form an imide ring. The carbonyl groups of the substituents at the 9th and 10th positions are preferably bonded via an oxygen atom to form a lactone ring, or bonded via a nitrogen atom to form an imide ring. Furthermore, the perylene compound is preferably a compound having a substituent having an oxy group bonded independently to the 1st, 6th, 7th and 12th positions. The perylene compound is preferably a red fluorescent dye. From the viewpoint of improving solubility in a solvent and improving the fluorescence intensity of the resulting color filter, the perylene compound is particularly preferably a compound represented by formula (II) (hereinafter, sometimes referred to as compound (II)).

[0100] <<Compound (II)>> [ka] [In formula (II), Ar 21 ~Ar 26 each independently represents an aryl group having 6 to 20 carbon atoms which may have a substituent (A3). R 21 ~R 24 each independently represents a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (A4), a halogen atom or a nitro group.]

[0101] Ar 21 ~Ar 26 Examples of the aryl group represented by the formula (I) include a phenyl group and a naphthyl group, and the phenyl group is preferred.

[0102] Ar 21 ~Ar 26Examples of the substituent (A3) which the aryl group represented by the formula (1) may have include a halogen atom, a nitrile group, a nitro group, an amino group, an amide group, a sulfonamide group, a hydroxy group, an alkyl group having 1 to 10 carbon atoms, such as a methyl group, an ethyl group, an isopropyl group, or a tert-butyl group, a cycloalkyl group having 1 to 20 carbon atoms, such as a cyclopropyl group or a cyclobutyl group, an alkenyl group having 2 to 10 carbon atoms, such as a vinyl group or a 1-propenyl group, an aryl group having 6 to 10 carbon atoms, such as a phenyl group or a 1-naphthyl group, an aralkyl group having 7 to 10 carbon atoms, such as a benzyl group or a phenethyl group, aryl groups; arylalkenyl groups having 8 to 10 carbon atoms, such as a phenylethenyl group (phenylvinyl group); alkoxy groups having 1 to 10 carbon atoms, such as a methoxy group and an ethoxy group; aryloxy groups having 6 to 10 carbon atoms, such as a phenyloxy group, a 1-naphthyloxy group and a 2-naphthyloxy group; thiol groups; alkylthio groups having 1 to 10 carbon atoms, such as a methylthio group and an ethylthio group; allylthio groups; arylthio groups having 6 to 10 carbon atoms, such as a phenylthio group, a 1-naphthylthio group and a 2-naphthylthio group; sulfoxy groups; carbonyl groups such as a methylsulfoxy group and an ethylsulfoxy group. alkylsulfoxy groups having 1 to 10 carbon atoms; arylsulfoxy groups having 6 to 10 carbon atoms, such as a phenylsulfoxy group, a 1-naphthylsulfoxy group, or a 2-naphthylsulfoxy group; a silyl group; a boryl group; alkylamino groups having 1 to 10 carbon atoms, such as a monomethylamino group, a dimethylamino group, a trimethylamino group, a monoethylamino group, a diethylamino group, or a triethylamino group; arylamino groups having 6 to 10 carbon atoms, such as a monophenylamino group; aralkylamino groups having 7 to 10 carbon atoms, such as a benzylamino group; an N-methylaminosulfonyl group, an N,N-diamino group, or alkylaminosulfonyl groups having 1 to 10 carbon atoms, such as a methylaminosulfonyl group and an N-ethylaminosulfonyl group, a carboxy group; a carbamoyl group; alkylcarbonyl groups having 2 to 10 carbon atoms, such as an acetyl group and a propionyl group; arylcarbonyl groups having 7 to 10 carbon atoms, such as a benzoyl group; alkoxycarbonyl groups having 2 to 10 carbon atoms, such as a methoxycarbonyl group and an ethoxycarbonyl group; aryloxycarbonyl groups having 7 to 20 carbon atoms, such as a phenyloxycarbonyl group; heterocyclic groups having 1 to 20 carbon atoms, such as a furyl group, a pyrrolyl group and a thienyl group;Examples of the alkyl group include a chloromethyl group, a dichloromethyl group, a fluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, and other alkyl groups having 1 to 10 carbon atoms in which some or all of the hydrogen atoms have been substituted with halogen atoms; a pentafluorosulfanyl group; and an acetylene group. Among these, an alkyl group having 1 to 10 carbon atoms and a halogen atom are preferred.

[0103] The halogen atom includes a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. From the viewpoint of synthesis, a fluorine atom and a chlorine atom are preferred. The alkyl group having 1 to 10 carbon atoms is preferably an alkyl group having 1 to 6 carbon atoms, and more preferably an alkyl group having 1 to 4 carbon atoms.

[0104] Ar 21 ~Ar 26 The aryl group represented by the following formula may or may not have one or more kinds of substituents (A3).

[0105] Ar 21 ~Ar 26 Examples of the group include groups represented by the following formulas (E-1) to (E-27), in which * represents a bond.

[0106] [ka]

[0107] Ar 21 and Ar 22 From the viewpoints of improving the solubility of compound (II) in a solvent and improving the fluorescence intensity of the resulting color filter, preferred is any of the groups represented by formulas (E-5), (E-7), (E-8) and (E-11). 23 ~Ar 26 From the viewpoints of improving the solubility of compound (II) in a solvent and improving the fluorescence intensity of the resulting color filter, preferred is any of the groups represented by formulas (E-1), (E-4), (E-9), (E-10), (E-17) and (E-18).

[0108] Ar21 ~Ar 26 may all be the same group or may be different groups. Ar 21 and Ar 22 are preferably the same group.

[0109] R 21 ~R 24 The hydrocarbon group having 1 to 20 carbon atoms represented by the above R is not limited to those having 21 or more carbon atoms. 1 , R 2 and R 11 Examples of the hydrocarbon group include the same as those of the hydrocarbon group represented by the following formula:

[0110] R 21 ~R 24 The substituent (A4) which may be possessed by the hydrocarbon group having 1 to 20 carbon atoms represented by the above R 1 , R 2 and R 11 Examples of the substituents are the same as those of the substituent (A1) which may be possessed by the hydrocarbon group having 1 to 30 carbon atoms and represented by the following formula:

[0111] R 21 ~R 24 Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

[0112] R 21 ~R 24 is preferably a hydrogen atom.

[0113] Specific examples of compound (II) include the compounds shown in Table 4 below.

[0114] [Table 4]

[0115] In Table 4, H represents a hydrogen atom, and E-1, E-6, E-7, E-10, E-17, E-18, and E-19 represent groups represented by the above formulas (E-1), (E-6), (E-7), (E-10), (E-17), (E-18), and (E-19), respectively.

[0116] Compound (II) is preferably compound (II-1) to (II-6), (II-9), (II-10), (II-15), (II-16), (II-21), or (II-22), and more preferably compound (II-3), (II-4), (II-9), (II-10), (II-15), or (II-16).

[0117] Compound (II) can be produced, for example, by reacting a compound represented by the following formula (pt2), a compound represented by the following formula (AR1), and a compound represented by the following formula (AR2) in a solvent.

[0118] [ka] [In the formula, R 21 ~R 24 is the same as defined above.]

[0119] Ar X -NH2(AR1) Ar X -OH (AR2) [In the formula, Ar X is the above-mentioned Ar 21 ~Ar 26 This is the same as the definition of

[0120] An example of the compound represented by formula (pt2) is 1,6,7,12-tetrachloroperylene tetracarboxylic dianhydride.

[0121] Examples of the compound represented by formula (AR1) include 2,6-diisopropylaniline, aniline, 3,5-dimethylaniline, 3,5-di-tert-butylaniline, etc. The compound represented by formula (AR1) may be used alone or in combination of two or more kinds.

[0122] Examples of the compound represented by formula (AR2) include phenol, 4-fluorophenol, 4-chlorophenol, 4-bromophenol, etc. The compound represented by formula (AR2) may be used alone or in combination of two or more.

[0123] The total amount of the compound represented by formula (AR1) and the compound represented by formula (AR2) used is usually 1 mol or more and 10 mol or less, preferably 1 mol or more and 8 mol or less, more preferably 1 mol or more and 6 mol or less, and even more preferably 1 mol or more and 4 mol or less, relative to 1 mol of the compound represented by formula (pt2).

[0124] Examples of the solvent include water, nitrile solvents such as acetonitrile, alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol, ether solvents such as diethyl ether and tetrahydrofuran, ketone solvents such as acetone and methyl isobutyl ketone, ester solvents such as ethyl acetate, aliphatic hydrocarbon solvents such as hexane, aromatic hydrocarbon solvents such as toluene, halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1,2-dichlorobenzene, amide solvents such as N,N-dimethylformamide and N-methylpyrrolidone, sulfoxide solvents such as dimethylsulfoxide, carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid, and imidazole. N-methylpyrrolidone, imidazole, and propionic acid are preferred.

[0125] The amount of the solvent used is usually 1 to 1000 parts by mass relative to 1 part by mass of the compound represented by formula (pt2).

[0126] The reaction temperature is usually from -100°C to 300°C, preferably from -90°C to 200°C, and more preferably from -10°C to 150°C.

[0127] After the reaction is completed, the method of extracting compound (II) is not particularly limited, and can be extracted by various known methods. For example, compound (II) can be extracted by distilling off the solvent. After the solvent is distilled off, the residue obtained may be purified by column chromatography or recrystallization. After the reaction is completed, compound (II) can be extracted by filtration. After the filtration, the residue obtained may be purified by column chromatography or recrystallization. The chemical structure of the obtained compound (II) can be analyzed by known analytical methods and their conditions. Examples of such analytical methods include, but are not limited to, X-ray crystal structure analysis, mass spectrometry (LC), NMR analysis, and elemental analysis. X-ray crystal structure analysis can be performed, for example, in accordance with Chemistry of Materials, 2012, Vol. 24, p. 4647-4652.

[0128] The compound (II-3) can be produced by reacting 1,6,7,12-tetrachloroperylenetetracarboxylic dianhydride with 2,6-diisopropylaniline and phenol in a solvent.

[0129] Representative commercially available products of compound (II-3) include Lumogen (registered trademark) F RED305 and the like.

[0130] When the colorant (A) contains a perylene compound, the content of the perylene compound in the total amount of the colorant (A) is, for example, 0.1 mass% or more, preferably 1 mass% or more, more preferably 3 mass% or more, even more preferably 5 mass% or more, still more preferably 10 mass% or more, and for example, 95 mass% or less, preferably 90 mass% or less, more preferably 85 mass% or less, even more preferably 80 mass% or less, and still more preferably 75 mass% or less.

[0131] Furthermore, when the colorant (A) contains a perylene compound, the content of the perylene compound, relative to the total amount of the benzoperylene compound and the perylene compound, is, for example, 3 mass% or more, preferably 5 mass% or more, and more preferably 10 mass% or more, and for example, 95 mass% or less, preferably 90 mass% or less, and more preferably 85 mass% or less.

[0132] When the colorant (A) contains a benzoperylene compound and a perylene compound, the benzoperylene compound can also serve as a sensitizer for the perylene compound.

[0133] <<Colorant (A1)>> The colored curable resin composition of the present invention may contain, as the colorant (A), a dye other than the benzoperylene compound and the perylene compound (hereinafter, sometimes referred to as dye (A1-1)) and / or a pigment (hereinafter, sometimes referred to as pigment (A1-2)) (hereinafter, the dye (A1-1) and the pigment (A1-2) may be collectively referred to as colorant (A1)). These may be used alone or in combination of two or more kinds.

[0134] The dye (A1-1) is not particularly limited, and known dyes can be used as long as they do not include benzoperylene compounds and perylene compounds, and examples thereof include solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified as dyes in the Color Index (published by The Society of Dyers and Colourists) and known dyes described in Dyeing Notes (Shikisensha). In addition, examples of dyes that can be used according to chemical structure include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone 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.

[0135] The pigment (A1-2) is not particularly limited, and any known pigment can be used, so long as it does not include a benzoperylene compound or a perylene compound. Examples of the pigment include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists). Examples of pigments classified as pigments include 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, and 231; 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, 144, 166, 168, 176, 177, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273; Blue pigments such as CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60; Violet pigments such as CI Pigment Violet 1, 19, 23, 32, 36, 38; Green pigments such as CI Pigment Green 7, 36, 58, 59, 62, 63; Brown pigments such as CI Pigment Brown 23, 25; Black pigments such as CI Pigment Black 1 and 7;

[0136] As the colorant (A1), red or green dyes and pigments are preferred.

[0137] If necessary, the colorant (A1) may be subjected to a rosin treatment, a surface treatment using a derivative having an acidic or basic group introduced therein, a graft treatment onto the surface of the colorant (A1) using a polymer compound, etc., a particle size reduction treatment using a sulfuric acid atomization method, etc., a washing treatment using an organic solvent or water to remove impurities, a removal treatment of ionic impurities using an ion exchange method, etc. The particle size of the colorant (A1) is preferably approximately uniform.

[0138] When the colorant (A) further contains a colorant (A1), the lower limit of the total content of the benzoperylene compound and the perylene compound in the colorant (A) is, for example, 1 mass% or more, preferably 2 mass% or more, more preferably 10 mass% or more, even more preferably 25 mass% or more, and particularly preferably 50 mass% or more, based on the total amount of the colorant (A). On the other hand, when the colorant (A) further contains a colorant (A1), the upper limit of the total content of the benzoperylene compound and the perylene compound in the colorant (A) is, for example, less than 100 mass% based on the total amount of the colorant (A).

[0139] When the colored curable resin composition contains a solvent (E), a colorant-containing liquid (sometimes called a colored composition) containing a colorant (A) and a solvent (E) may be prepared in advance, and then the colored curable resin composition may be prepared using the colorant-containing liquid. When the colorant (A) is not soluble in the solvent (E), for example, when the colorant (A) contains a pigment (A1-2), the colorant-containing liquid can be prepared by dispersing the colorant (A) in the solvent (E) and mixing. The colorant-containing liquid may contain a part or all of the solvent (E) contained in the colored curable resin composition.

[0140] The solid content in the colorant-containing liquid is preferably 0.01% by mass or more and 99.99% by mass or less, more preferably 0.1% by mass or more and 99.9% by mass or less, even more preferably 0.1% by mass or more and 99% by mass or less, still more preferably 0.5% by mass or more and 90% by mass or less, and particularly preferably 1% by mass or more and 50% by mass or less, based on the total amount of the colorant-containing liquid.

[0141] The colorant (A) can be made uniformly dispersed in the solution by adding a dispersant and carrying out a dispersion treatment. When two or more types of colorant (A) are used in combination, each may be dispersed alone, or a mixture of multiple types may be dispersed.

[0142] 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 Co., Ltd.), and BYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.). Resin (B) described later may be used as the dispersant.

[0143] When a dispersant is used, the amount of the dispersant (solid content) used is usually 1 part by mass or more and 10,000 parts by mass or less, preferably 5 parts by mass or more and 5,000 parts by mass or less, more preferably 10 parts by mass or more and 1,000 parts by mass or less, and even more preferably 15 parts by mass or more and 800 parts by mass or less, relative to 100 parts by mass of the colorant (A). When the amount of the dispersant used is within the above range, a colorant-containing liquid in a more uniformly dispersed state tends to be obtained.

[0144] The content of the colorant (A) is preferably 0.1% by mass or more and 50% by mass or less, more preferably 0.5% by mass or more and 40% by mass or less, and even more preferably 1% by mass or more and 30% by mass or less, based on the total amount of solids in the colored curable resin composition. When the content of the colorant (A) is within the above range, the color density when made into a color filter is sufficient, and since the necessary amount of the resin (B) can be contained in the composition, a pattern with sufficient mechanical strength can be formed, which is preferable. Here, the "total amount of solids" in this specification refers to the amount obtained by subtracting the content of the solvent from the total amount of the colored curable resin composition. The total amount of solids and the content of each component relative thereto can be measured by a known analytical means such as liquid chromatography or gas chromatography.

[0145] <Resin (B)> The resin (B) is not particularly limited, but is preferably an alkali-soluble resin, and more preferably a polymer having a structural unit derived from at least one monomer (hereinafter sometimes referred to as "monomer (a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides. Resin (B) is preferably a copolymer having a structural unit derived from a monomer having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as "monomer (b)"), and other structural units. Examples of other structural units include structural units derived from a monomer copolymerizable with monomer (a) (however, different from monomer (a) and monomer (b) (hereinafter, sometimes referred to as "monomer (c)"), structural units having an ethylenically unsaturated bond, etc.

[0146] Examples of the monomer (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, and p-vinylbenzoic acid; Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid; Bicyclounsaturated compounds containing a carboxy group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; carboxylic acid anhydrides such as the anhydrides of the above unsaturated dicarboxylic acids except fumaric acid and mesaconic acid; Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids, such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate; Unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid; and the like. Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferred from the standpoint of copolymerization reactivity and solubility of the resulting resin in an aqueous alkaline solution. 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.

[0147] Monomer (b) refers to a polymerizable compound 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 (oxolane ring)) and an ethylenically unsaturated bond. Monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0148] Examples of the monomer (b) include a monomer having an oxiranyl group and an ethylenically unsaturated bond (hereinafter, may be referred to as "monomer (b1)"), a monomer having an oxetanyl group and an ethylenically unsaturated bond (hereinafter, may be referred to as "monomer (b2)"), and a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter, may be referred to as "monomer (b3)").

[0149] Examples of the monomer (b1) include a monomer having a structure obtained by epoxidizing an unsaturated aliphatic hydrocarbon (hereinafter, may be referred to as "monomer (b1-1)") and a monomer having a structure obtained by epoxidizing an unsaturated alicyclic hydrocarbon (hereinafter, may be referred to as "monomer (b1-2)").

[0150] As the monomer (b1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferable. Specific examples of the monomer (b1-1) include glycidyl (meth)acrylate, β-methyl glycidyl (meth)acrylate, β-ethyl glycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis( Examples of such styrene include 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.

[0151] Examples of the monomer (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celloxide (registered trademark) 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer (registered trademark) A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer (registered trademark) M100; manufactured by Daicel Corporation), compounds represented by formula (BI) and compounds represented by formula (BII).

[0152] [ka]

[0153] [In formula (BI) and formula (BII), R a and R b each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group may be substituted with a hydroxy group. X a and X b are, independently of each other, a single bond, *-R c -, *-R c -O-, *-R c -S- or *-R c -NH-. R c represents an alkanediyl group having 1 to 6 carbon atoms. * represents a bond to O.]

[0154] Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, and a tert-butyl group.

[0155] Examples of the alkyl group in which a hydrogen atom is substituted with a hydroxy group include a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 1-hydroxypropyl group, a 2-hydroxypropyl group, a 3-hydroxypropyl group, a 1-hydroxy-1-methylethyl group, a 2-hydroxy-1-methylethyl group, a 1-hydroxybutyl group, a 2-hydroxybutyl group, a 3-hydroxybutyl group, and a 4-hydroxybutyl group.

[0156] R a and R b Preferred examples of the alkyl group include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, and a 2-hydroxyethyl group, and more preferred examples include a hydrogen atom and a methyl group.

[0157] Examples of the alkanediyl group include a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-1,6-diyl group.

[0158] X a and X b Preferred examples of the alkyl group include a single bond, a methylene group, an ethylene group, a -CH2-O- (* represents a bond to O) group, and a -CH2CH2-O- group, and more preferred examples include a single bond and a -CH2CH2-O- group (* represents a bond to O).

[0159] The compound represented by formula (BI) includes compounds represented by any one of formulas (BI-1) to (BI-15), etc. Among them, compounds represented by formulas (BI-1), (BI-3), (BI-5), (BI-7), (BI-9) and (BI-11) to (BI-15) are preferred, and compounds represented by formulas (BI-1), (BI-7), (BI-9) and (BI-15) are more preferred.

[0160] [ka]

[0161] Examples of the compound represented by formula (BII) include compounds represented by any of formulas (BII-1) to (BII-15), and among these, preferred are compounds represented by formulas (BII-1), (BII-3), (BII-5), (BII-7), (BII-9) and (BII-11) to (BII-15), and more preferred are compounds represented by formulas (BII-1), (BII-7), (BII-9) and (BII-15).

[0162] [ka]

[0163] The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone, or the compound represented by formula (BI) and the compound represented by formula (BII) may be used in combination. When these are used in combination, the content ratio of the compound represented by formula (BI) and the compound represented by formula (BII) is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, and further preferably 20:80 to 80:20 on a molar basis.

[0164] As the monomer (b2) having an oxetanyl group and an ethylenically unsaturated bond, a monomer having an oxetanyl group and a (meth)acryloyloxy group is more preferable. Examples of the monomer (b2) include 3-methyl-3-(meth)acryloyloxymethyloxetane, 3-ethyl-3-(meth)acryloyloxymethyloxetane, 3-methyl-3-(meth)acryloyloxyethyloxetane, and 3-ethyl-3-(meth)acryloyloxyethyloxetane.

[0165] The monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond is preferably a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group. Examples of the monomer (b3) include tetrahydrofurfuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, etc.

[0166] Examples of the monomer (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decan-8-yl(meth)acrylate (commonly known in the art as "dicyclopentanyl(meth)acrylate" and sometimes called "tricyclodecyl(meth)acrylate"), tricyclo[5.2.1.0 2,6 ]Decan-9-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decene-8-yl(meth)acrylate (known in the art as the common name "dicyclopentenyl(meth)acrylate"), tricyclo[5.2.1.0 2,6 ](meth)acrylic acid esters such as decene-9-yl (meth)acrylate, dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate; hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate; Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene chloro[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept bicyclounsaturated compounds such as 5,6-diethoxybicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-hydroxy-5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxymethyl-5-methylbicyclo[2.2.1]hept-2-ene, 5-tert-butoxycarbonylbicyclo[2.2.1]hept-2-ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene; dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate and N-(9-acridinyl)maleimide; Examples of the vinyl group-containing aromatic compounds include styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, and p-methoxystyrene; vinyl group-containing nitriles such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; vinyl group-containing amides such as (meth)acrylamide; esters such as vinyl acetate; and dienes such as 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene. Among these, styrene, vinyltoluene, tricyclo[5.2.1.0] and cyclopentadiene are preferred from the viewpoints of copolymerization reactivity and heat resistance. 2,6 ]Decan-8-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]Decan-9-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]Decen-8-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ]decen-9-yl(meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, and benzyl(meth)acrylate are preferred.

[0167] The structural unit having an ethylenically unsaturated bond is preferably a structural unit having a (meth)acryloyl group. A resin having such a structural unit can be obtained by adding a monomer having an ethylenically unsaturated bond and a group capable of reacting with the group possessed by the monomer (a) or the monomer (b) to a polymer having a structural unit derived from the monomer (a) or the monomer (b). Examples of such structural units include a structural unit in which glycidyl (meth)acrylate is added to a (meth)acrylic acid unit, a structural unit in which 2-hydroxyethyl (meth)acrylate is added to a maleic anhydride unit, and a structural unit in which (meth)acrylic acid is added to a glycidyl (meth)acrylate unit, etc. In addition, when these structural units have a hydroxy group, structural units in which a carboxylic acid anhydride is further added can also be mentioned as structural units having an ethylenically unsaturated bond.

[0168] A polymer having a structural unit derived from the monomer (a) can be produced, for example, by polymerizing a monomer constituting a structural unit of the polymer in a solvent in the presence of a polymerization initiator. The polymerization initiator and the solvent are not particularly limited, and those usually used in the relevant field can be used. For example, the polymerization initiator can be an azo compound (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) or an organic peroxide (benzoyl peroxide, etc.), and the solvent can be any one that dissolves each monomer, such as the solvent (E) described below.

[0169] The resulting copolymer may be used as it is in the form of a solution after the reaction, or may be a concentrated or diluted solution, or may be extracted as a solid (powder) by a method such as reprecipitation. In particular, by using a solvent (E) described below as a solvent during the polymerization, the solution after the reaction can be used as it is, and the production process can be simplified. If necessary, a reaction catalyst for the reaction of a carboxylic acid or a carboxylic acid anhydride with a cyclic ether (eg, tris(dimethylaminomethyl)phenol, etc.) and a polymerization inhibitor (eg, hydroquinone, etc.) may be used. Examples of the carboxylic acid anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride.

[0170] Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl(meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]Decyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth) Acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / (meth)acrylic acid / vinyl toluene copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / (meth)acrylic acid / benzyl (meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / (meth)acrylic acid / 2-ethylhexyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ]Decyl (meth)acrylate / Tricyclo[5.2.1.0 2,6 ]Decenyl (meth)acrylate / (meth)acrylic acid / N-cyclohexylmaleimide copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane / (meth)acrylic acid / styrene copolymer, benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer, and resins described in JP-A-9-106071, JP-A-2004-29518, and JP-A-2004-361455 are examples thereof. Among these, the resin (B) is preferably a copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b).

[0171] Resin (B) may be a combination of two or more kinds. In this case, resin (B) is at least It is preferable that the composition contains at least one copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b), More preferably, the copolymer contains at least one copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b1), It is more preferable that the copolymer contains at least one copolymer containing a structural unit derived from the monomer (a) and a structural unit derived from the monomer (b1-2), 3,4-Epoxytricyclo[5.2.1.0 2,6 ] decyl (meth) acrylate / (meth) acrylic acid copolymer, 3,4-epoxy tricyclo[5.2.1.0 2,6 ]decyl (meth)acrylate / (meth)acrylic acid / N-cyclohexylmaleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Decyl (meth)acrylate / (meth)acrylic acid / vinyl toluene copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] It is even more preferable that the copolymer contains one or more selected from the group consisting of decyl (meth)acrylate / (meth)acrylic acid / 2-ethylhexyl (meth)acrylate copolymers.

[0172] The polystyrene-equivalent weight average molecular weight (Mw) of the resin (B) is preferably from 1,000 to 100,000, more preferably from 2,000 to 50,000, and even more preferably from 3,000 to 30,000. When the weight average molecular weight is within the above range, the solubility of the unexposed area in a developer is high, and the residual film rate and hardness of the obtained pattern also tend to be high. The dispersity of the resin (B) [weight average molecular weight (Mw) / number average molecular weight (Mn)] is preferably 1 or more and 6 or less, more preferably 1.001 or more and 4 or less, and further preferably 1.01 or more and 4 or less.

[0173] The acid value (solid content equivalent value) of the resin (B) is preferably 10 mg-KOH / g or more and 300 mg-KOH / g or less, more preferably 20 mg-KOH / g or more and 250 mg-KOH / g or less, even more preferably 25 mg-KOH / g or more and 200 mg-KOH / g or less, even more preferably 30 mg-KOH / g or more and 150 mg-KOH / g or less, and particularly preferably 60 mg-KOH / g or more and 135 mg-KOH / g or less. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin, and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

[0174] The content of the resin (B) is preferably 5 to 50 mass%, more preferably 10 to 40 mass%, and further preferably 15 to 30 mass%, based on 100 mass% of the solid content of the colored curable resin composition. When the content of the resin (B) is within the above range, the solubility of the unexposed area in a developer tends to be high.

[0175] <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.

[0176] Examples of the polymerizable compound having one ethylenically unsaturated bond include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, and the like, as well as the above-mentioned monomers (a), (b) and (c).

[0177] Examples of the polymerizable compound having two ethylenically unsaturated bonds include 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bis(acryloyloxyethyl)ether of bisphenol A, and 3-methylpentanediol di(meth)acrylate.

[0178] 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, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris(2-(meth)acryloyloxyethyl)isocyanurate, ethylenediaminetetraacet ... Examples of the polyvinyl chloride-modified acrylate include ethylene glycol-modified pentaerythritol tetra(meth)acrylate, ethylene glycol-modified dipentaerythritol hexa(meth)acrylate, propylene glycol-modified pentaerythritol tetra(meth)acrylate, propylene glycol-modified dipentaerythritol hexa(meth)acrylate, caprolactone-modified pentaerythritol tetra(meth)acrylate, and caprolactone-modified dipentaerythritol hexa(meth)acrylate, and preferably dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

[0179] The weight average molecular weight of the polymerizable compound (C) is preferably 50 or more and 4,000 or less, more preferably 70 or more and 3,500 or less, even more preferably 100 or more and 3,000 or less, still more preferably 150 or more and 2,900 or less, and particularly preferably 250 or more and 1,500 or less.

[0180] The content of the polymerizable compound (C) may be, for example, 1 mass % or more and 99 mass % or less, preferably 5 mass % or more and 90 mass % or less, more preferably 10 mass % or more and 80 mass % or less, and even more preferably 20 mass % or more and 70 mass % or less, based on the total amount of solids in the colored curable resin composition.

[0181] <Polymerization initiator (D)> 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 and initiate polymerization, and any known polymerization initiator can be used.

[0182] Examples of the polymerization initiator (D) include O-acyloxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds.

[0183] Examples of the O-acyloxime compound 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, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, and N-acetoxy-1-[ 9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazol-3-yl]ethan-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-imine, and N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-3-cyclopentylpropan-1-one-2-imine. In addition, as the O-acyloxime compound, commercially available products such as Irgacure (registered trademark) OXE01, OXE02 (both manufactured by BASF) and N-1919 (manufactured by ADEKA Co., Ltd.) may be used. Among them, as the O-acyloxime compound, at least one selected from the group consisting of N-benzoyloxy-1-(4-phenylsulfanylphenyl)butan-1-one-2-imine, N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine and N-benzoyloxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropan-1-one-2-imine is preferred, and N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine is more preferred.

[0184] Examples of the alkylphenone compound include 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, and 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholinyl)phenyl]butan-1-one. Commercially available alkylphenone compounds such as Irgacure (registered trademark) 369, 907, and 379 (all manufactured by BASF) may also be used. Alkylphenone compounds also include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyl dimethyl ketal.

[0185] Examples of the biimidazole compound include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, 2,2'-bis(2,3-dichlorophenyl)-4,4',5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, and 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole. 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B-48-38403 and JP-A-62-174204), and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted by carboalkoxy groups (see, for example, JP-A-7-10913).

[0186] The triazine compounds include 2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxynaphthyl)-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-(4-methoxystyryl)-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[2-( 5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine.

[0187] Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide, etc. Commercially available products such as Irgacure (registered trademark) 819 (manufactured by BASF) may also be used.

[0188] Further examples of the polymerization initiator (D) include benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether; benzophenone compounds such as benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, and 2,4,6-trimethylbenzophenone; quinone compounds such as 9,10-phenanthrenequinone, 2-ethylanthraquinone, and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with a polymerization initiator aid (D1) (particularly amines) described below.

[0189] The polymerization initiator (D) is preferably a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound, and a biimidazole compound, and more preferably a polymerization initiator containing an O-acyloxime compound.

[0190] The content of the polymerization initiator (D) is preferably 0.1 parts by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 20 parts by mass or less, based on 100 parts by mass of the total amount of all the resins (B) and the polymerizable compound (C) contained in the colored curable resin composition. 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.

[0191] <Polymerization initiator aid (D1)> The polymerization initiation aid (D1) is a compound used to promote the polymerization of the polymerizable compound (C) whose polymerization has been initiated by the polymerization initiator (D), or a sensitizer. When the polymerization initiation aid (D1) is contained, it is usually used in combination with the polymerization initiator (D).

[0192] Examples of the polymerization initiator aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0193] Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone, and preferably 4,4'-bis(diethylamino)benzophenone. In addition, commercially available products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used as the amine compound.

[0194] Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxyanthracene, and 2-ethyl-9,10-dibutoxyanthracene.

[0195] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0196] Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

[0197] When these polymerization initiation aids (D1) are used, the content thereof is preferably 0.1 parts by mass or more and 30 parts by mass or less, more preferably 1 part by mass or more and 20 parts by mass or less, relative to 100 parts by mass of the total amount of all the resins (B) and the polymerizable compounds (C) contained in the colored curable resin composition.

[0198] <Solvent (E)> The solvent (E) is not particularly limited, and any solvent commonly used in the art can be used. Examples of the solvent (E) include ester solvents (solvents containing -COO- in the molecule and not containing -O-), ether solvents (solvents containing -O- in the molecule and not containing -COO-), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- in the molecule and not containing -COO-), alcohol solvents (solvents containing OH in the molecule and not containing -O-, -CO- and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc. Two or more of these solvents may be used in combination.

[0199] Examples of ester solvents include methyl lactate, ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, ethyl acetate, n-butyl acetate, isobutyl acetate, pentyl formate, isopentyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone.

[0200] Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetole, and methylanisole.

[0201] Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methyl ...2-ethoxy-2-methylpropionate, and methyl 2-ethoxy-2-methylpropionate. Examples of the monomer units include ethyl acetate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate.

[0202] Examples of ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone, and isophorone.

[0203] Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0204] Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0205] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0206] As the solvent (E), propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate and cyclohexanone are preferred.

[0207] When the solvent (E) is included, the content of the solvent (E) is usually 99.99% by mass or less, preferably 40% by mass or more and 99% by mass or less, more preferably 50% by mass or more and 95% by mass or less, even more preferably 70% by mass or more and 95% by mass or less, and even more preferably 75% by mass or more and 90% by mass or less, based on the total amount of the colored curable resin composition. In other words, the total amount of solids in the colored curable resin composition is usually 0.01% by mass or more, preferably 1% by mass or more and 60% by mass or less, more preferably 5% by mass or more and 50% by mass or less, even more preferably 5% by mass or more and 30% by mass or less, and even more preferably 10% by mass or more and 25% by mass or less. 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.

[0208] <Leveling agent (F)> Examples of the leveling agent (F) include silicone surfactants, fluorine surfactants, and silicone surfactants having fluorine atoms, which may have a polymerizable group in the side chain.

[0209] Examples of silicone surfactants include surfactants having a siloxane bond in the molecule.Specific examples include Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, and SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, and KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF4446, TSF4452, and TSF4460 (manufactured by Momentive Performance Materials Japan LLC).

[0210] Examples of fluorine-based surfactants include surfactants having a fluorocarbon chain in the molecule.Specific examples include Fluorad (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, R30, RS-718-K (manufactured by DIC Corporation), F-top (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon (registered trademark) S381, S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.), and E5844 (manufactured by Daikin Fine Chemicals Research Institute Co., Ltd.).

[0211] Examples of silicone surfactants having fluorine atoms include surfactants having a siloxane bond and a fluorocarbon chain in the molecule, such as Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

[0212] When the leveling agent (F) is contained, the content of the leveling agent (F) is preferably 0.0005% by mass or more and 1% by mass or less, more preferably 0.001% by mass or more and 0.5% by mass or less, and even more preferably 0.005% by mass or more and 0.1% by mass or less, based on the total amount of the colored curable resin composition. This content does not include the content of the pigment dispersant. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

[0213] <Other ingredients> The colored curable resin composition may contain additives known in the technical field, such as a filler, another polymer compound, an adhesion promoter, a quencher, an antioxidant, a light stabilizer, and a chain transfer agent, as necessary.

[0214] <Method for producing colored curable resin composition> The colored curable resin composition can be prepared by mixing the colorant (A), the resin (B), the polymerizable compound (C), and the polymerization initiator (D), as well as the solvent (E), the leveling agent (F), and other components that are used as needed. The mixing can be performed using known or conventional equipment and conditions. The colorant (A) may be mixed in advance with a part or all of the solvent (E) and dispersed using a bead mill or the like until the average particle size is about 0.2 μm or less, and is preferably used in a dispersed state. In this case, the dispersant and a part or all of the resin (B) may be mixed as necessary. The colorant (A) may also be used in a state in which it is dissolved in a part or all of the solvent (E) in advance. The remaining components are mixed into the colorant-containing liquid obtained in this way to a predetermined concentration, thereby preparing the desired colored curable resin composition.

[0215] <Manufacturing method of color filters> A color filter, which may be a color conversion layer, can be formed from the colored curable resin composition. Examples of methods for forming a colored pattern include photolithography, inkjet, and printing. Among them, photolithography is preferred. The photolithography is a method in which the colored curable resin composition is applied to a substrate, dried to form a colored curable resin composition layer, and the colored curable resin composition layer is exposed through a photomask and developed. In the photolithography method, a colored coating film, which is a cured product of the colored curable resin composition layer, can be formed by not using a photomask during exposure and / or not developing. The colored pattern or colored coating film thus formed is the color filter of the present invention.

[0216] The film thickness of the color filter to be produced is not particularly limited and can be appropriately adjusted depending on the purpose or use, and is, for example, 0.1 μm to 30 μm, preferably 0.1 μm to 20 μm, and more preferably 0.5 μm to 6 μm.

[0217] The substrate may be a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, or soda lime glass with a silica-coated surface, a resin plate such as polycarbonate, polymethylmethacrylate, or polyethylene terephthalate, silicon, or a substrate having a thin film of aluminum, silver, or a silver / copper / palladium alloy formed thereon. On these substrates, other color filter layers, resin layers, transistors, circuits, etc. may be formed.

[0218] The formation of each color pixel by photolithography can be carried out using known or conventional equipment and conditions. For example, the pixel can be produced as follows. First, the colored curable resin composition is applied onto a substrate, and then dried by heating and drying (prebaking) and / or drying under reduced pressure to remove volatile components such as solvents, thereby obtaining a smooth colored curable resin composition layer. Examples of the coating method include spin coating, slit coating, and slit and spin coating. The temperature when drying by heating is preferably from 30° C. to 120° C., and more preferably from 50° C. to 110° C. The heating time is preferably from 10 seconds to 60 minutes, and more preferably from 30 seconds to 30 minutes. When drying under reduced pressure is performed, it is preferable to perform the drying under a pressure of 50 Pa or more and 150 Pa or less at a temperature range of 20° C. or more and 25° C. or less. The thickness of the colored curable resin composition layer is not particularly limited, and may be appropriately selected depending on the intended thickness of the color filter.

[0219] Next, the colored curable resin composition layer is exposed through a photomask for forming a desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern according to the intended use is used. In addition, it is preferable to use an exposure device such as a mask aligner or a stepper, since it is possible to uniformly irradiate the entire exposed surface with parallel light and to accurately align the photomask with the substrate on which the colored curable resin composition layer is formed.

[0220] The light source used for exposure is preferably a light source that generates light with a wavelength of 250 nm or more and 450 nm or less. For example, light less than 350 nm may be cut using a filter that cuts this wavelength range, or light around 436 nm, around 408 nm, and around 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specific examples include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps.

[0221] The colored curable resin composition layer after exposure is brought into contact with a developer and developed to form a colored pattern on the substrate. The unexposed portion of the colored curable resin composition layer is dissolved in the developer and removed by development. The developer is preferably an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.03% by mass or more and 5% by mass or less. Furthermore, the developer may contain a surfactant. The developing method may be any of a puddle method, a dipping method, a spray method, etc. Furthermore, the substrate may be inclined at an arbitrary angle during the developing. After development, the substrate is preferably washed with water.

[0222] Furthermore, it is preferable to perform post-baking on the obtained colored pattern. The post-baking temperature is preferably from 150° C. to 250° C., more preferably from 160° C. to 240° C. The post-baking time is preferably from 1 minute to 120 minutes, more preferably from 10 minutes to 60 minutes.

[0223] <Display device> The color filter is useful as a color filter for use in display devices (for example, liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging devices, particularly as a color filter for use in organic EL devices.

[0224] A color filter formed from the benzoperylene compound and colored curable resin composition of the present invention has high fluorescent intensity, and therefore can be a color filter with excellent brightness. The fluorescence intensity can be measured, for example, using a fluorescence spectrophotometer (FluoroMAX-3; manufactured by Horiba, Ltd.).

[0225] In addition, the benzoperylene compound of the present invention has high solubility in solvents (such as propylene glycol monomethyl ether acetate). Furthermore, a color filter formed from the benzoperylene compound and the colored curable resin composition of the present invention not only has high fluorescent intensity and excellent brightness, but also tends to have excellent heat resistance and light resistance. EXAMPLES

[0226] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to the following examples, and can be modified as long as it satisfies the spirit of the invention, and all such modifications are included in the technical scope of the present invention. In the following, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass".

[0227] In the following examples, the structures of the compounds were confirmed by mass spectrometry (LC; Agilent 1200 model, MASS; Agilent LC / MSD6130 model).

[0228] The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by GPC under the following conditions. Equipment: HLC-8120GPC (Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40℃ y: Tetrahydrofuran Flow rate: 1.0mL / min Solid concentration of the analytical sample: 0.001 to 0.01% by mass Injection volume: 50μL Detector: RI Calibration standard materials: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation) The ratio of the weight average molecular weight and the number average molecular weight (Mw / Mn) calculated in terms of polystyrene obtained above was taken as the dispersity.

[0229] (Synthesis Example 1) <Preparation of compound (I-21)> N 1 ,N 2 20 parts of 2,6-bis(2,6-diisopropylphenyl)perylene-3,4,9,10-tetracarboxylic diimide (manufactured by Tokyo Chemical Industry Co., Ltd.), 788 parts of maleic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), and 12 parts of p-chloranil (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at 170°C for 25 hours. While the obtained mixture was kept at 70°C or less, 800 parts of 1 mol / L hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) and 300 parts of acetone (manufactured by Kanto Chemical Co., Ltd.) that had been prepared in advance were added, and a yellow precipitate was generated. The mixture containing this yellow precipitate was filtered, and the residue after filtration was washed with 400 parts of water and 200 parts of methanol. The obtained residue was dried under reduced pressure at 60°C to obtain N-type 1-methyl-2-phenyl-2-propanediol represented by formula (I-21). 1 ,N 2 -Bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-acid anhydride (hereinafter sometimes referred to as compound (I-21)) was obtained in an amount of 15 parts (yield 75%).

[0230] [ka]

[0231] <Identification of compound (I-21)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 805 Exact Mass: 804

[0232] (Synthesis Example 2) <Preparation of compound (I-23)> N obtained in Synthesis Example 1 1 ,N 22.0 parts of 2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-anhydride, 0.88 parts of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.), and 120 parts of propionic acid (manufactured by Tokyo Chemical Industry Co., Ltd.) were added and stirred at 140°C for 6 hours. The mixture obtained was concentrated, and 5 parts of methanol were added, resulting in the formation of a yellow precipitate. The mixture containing this yellow precipitate was filtered, and the residue after filtration was washed with 2 parts of methanol. The residue obtained was dried under reduced pressure at 60°C and purified by a silica gel column (solvent: chloroform), resulting in the formation of N-(2-methyl-2-phenylpropane)-2,3,8,9-bisimide-11,12-anhydride represented by the formula (I-23). 1 ,N 2 ,N 3 As a result, 1.7 parts of -tris(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter sometimes referred to as compound (I-23)) was obtained (yield 68%).

[0233] [ka]

[0234] <Identification of compound (I-23)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 965 Exact Mass: 964

[0235] (Synthesis Example 3) <Preparation of Compound (I-1)> N 1 ,N 21.6 parts of 1-bis(3-pentyl)perylene-3,4,9,10-tetracarboxylic diimide (manufactured by Aldrich), 84 parts of maleic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.), and 1.3 parts of p-chloranil (manufactured by Tokyo Chemical Industry Co., Ltd.) were added, and the mixture was stirred at 220°C for 30 hours. While the obtained mixture was kept at 70°C or less, 256 parts of 1 mol / L hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) and 96 parts of acetone (manufactured by Kanto Chemical Co., Ltd.) that had been prepared in advance were added, and a yellow precipitate was generated. The mixture containing this yellow precipitate was filtered, and the residue after filtration was washed with 400 parts of water and 200 parts of methanol. The obtained residue was dried under reduced pressure at 60°C to obtain N-type tetrahydrofuran represented by formula (I-1). 1 ,N 2 As a result, 1.4 parts of -bis(3-pentyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-acid anhydride (hereinafter sometimes referred to as compound (I-1)) was obtained (yield 75%).

[0236] [ka]

[0237] <Identification of compound (I-1)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 625 Exact Mass: 624

[0238] <Preparation of Compound (I-3)> N 1 ,N 2 The same procedure as in Synthesis Example 2 was repeated to obtain N-bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-anhydride, except that 2.0 parts of the compound (I-1) was replaced with 2.5 parts of the compound (I-1) and 0.88 parts of 2,6-diisopropylaniline was replaced with 1.4 parts. 1 ,N 2 -Bis(3-pentyl)-N 31.8 parts of -(2,6-diisopropylphenyl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter sometimes referred to as compound (I-3)) was obtained (yield 85%).

[0239] [ka]

[0240] <Identification of compound (I-3)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 784 Exact Mass: 783

[0241] (Synthesis Example 4) <Preparation of compound (I-22)> The same procedure as in Synthesis Example 2 was repeated to prepare N-type 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) represented by the formula (I-22), except that 0.88 parts of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 1.0 parts of 7-tridecaamine. 1 ,N 2 -Bis(2,6-diisopropylphenyl)-N 3 1.4 parts of -(7-tridecyl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter sometimes referred to as compound (I-22)) were obtained (yield 58%).

[0242] [ka]

[0243] <Identification of compound (I-22)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 987 Exact Mass: 986

[0244] (Synthesis Example 5) <Preparation of compound (I-24)> The same procedure as in Synthesis Example 2 was repeated to prepare N-phenylene ether represented by the formula (I-24), except that 0.88 parts of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 1.0 parts of 2,5-di-tert-butylaniline. 1 ,N 2 -Bis(2,6-diisopropylphenyl)-N 3 2.0 parts of -(2,5-di-tert-butylphenyl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter sometimes referred to as compound (I-24)) was obtained (yield 81%).

[0245] [ka]

[0246] <Identification of compound (I-24)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 993 Exact Mass: 992

[0247] (Synthesis Example 6) <Preparation of compound (I-25)> The same procedure as in Synthesis Example 2 was repeated to prepare N-phenylenediamine represented by formula (I-25), except that 0.88 parts of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 0.88 parts of 4-tert-butyl-2,6-dimethylaniline (manufactured by Aldrich Co., Ltd.). 1 ,N 2 -Bis(2,6-diisopropylphenyl)-N 3 2.4 parts of -(4-tert-butyl-2,6-dimethylphenyl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter sometimes referred to as compound (I-25)) were obtained (yield 77%).

[0248] [ka]

[0249] <Identification of compound (I-25)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 964 Exact Mass: 963

[0250] (Synthesis Example 7) <Preparation of compound (I-26)> The same procedure as in Synthesis Example 2 was repeated to prepare N-phenylene ether represented by the formula (I-26), except that 0.88 parts of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 1.1 parts of 4-bromo-2,6-diisopropylaniline (manufactured by Aldrich Co., Ltd.). 1 ,N 2 -Bis(2,6-diisopropylphenyl)-N 3 1.7 parts of -(4-bromo-2,6-diisopropylphenyl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter sometimes referred to as compound (I-26)) was obtained (yield 70%).

[0251] [ka]

[0252] <Identification of compound (I-26)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1043 Exact Mass: 1041

[0253] (Synthesis Example 8) <Preparation of compound (I-27)> The same procedure as in Synthesis Example 2 was repeated to prepare N-phenylene ether represented by the formula (I-27), except that 0.88 parts of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 0.92 parts of 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalene-2-amine (manufactured by AmBeed). 1 ,N 2 -Bis(2,6-diisopropylphenyl)-N 31.7 parts of -(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter sometimes referred to as compound (I-27)) was obtained (yield 70%).

[0254] [ka]

[0255] <Identification of compound (I-27)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1004 Exact Mass: 1003

[0256] (Synthesis Example 9) <Preparation of compound (I-28)> The same procedure as in Synthesis Example 2 was repeated to prepare N-phenylenediamine represented by the formula (I-28), except that 0.88 parts of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.) was replaced with 0.74 parts of 1,2,3,5,6,7-hexahydro-s-indacen-4-amine (manufactured by AChemBlock). 1 ,N 2 -Bis(2,6-diisopropylphenyl)-N 3 1.6 parts of -(1,2,3,5,6,7-hexahydro-s-indacen-4-yl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter sometimes referred to as compound (I-28)) was obtained (yield 66%).

[0257] [ka]

[0258] <Identification of compound (I-28)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 960 Exact Mass: 959

[0259] (Synthesis Example 10) <Preparation of compound (I-11)> N 1 ,N 2 -Bis(3-pentyl)perylene-3,4,9,10-tetracarboxylic diimide 1 ,N 2 The same procedure as in Synthesis Example 3 was repeated except that 1,2,3,4,5,6,7-tridecylperylene-3,4,9,10-tetracarboxylic diimide was used instead of 1,2,3,4,5,6,7-tridecylperylene-3,4,9,10-tetracarboxylic diimide, and N 1 ,N 2 2.1 parts of -bis(7-tridecyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-acid anhydride (hereinafter sometimes referred to as compound (I-11)) were obtained (yield 74%).

[0260] [ka]

[0261] <Identification of compound (I-11)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 849 Exact Mass: 848

[0262] <Preparation of compound (I-12)> N 1 ,N 2 The same procedure as in Synthesis Example 2 was repeated to obtain N-bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-acid anhydride, except that 2.0 parts were replaced with 3.0 parts of the above compound (I-11) and 0.88 parts of 2,6-diisopropylaniline were replaced with 1.2 parts of 7-tridecylamine (manufactured by Tokyo Chemical Industry Co., Ltd.). 1 ,N 2 ,N 3As a result, 2.7 parts of -tris(7-tridecyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter sometimes referred to as compound (I-12)) was obtained (yield 75%).

[0263] [ka]

[0264] <Identification of compound (I-12)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1031 Exact Mass: 1030

[0265] (Synthesis Example 11) <Preparation of compound (I-13)> N 1 ,N 2 The same procedure as in Synthesis Example 2 was repeated to obtain N-bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-anhydride, except that 2.0 parts of the compound (I-11) and 0.88 parts of 2,6-diisopropylaniline were replaced with 1.1 parts. 1 ,N 2 -Bis(7-tridecyl)-N 3 2.9 parts of -(2,6-diisopropylphenyl)-benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid triimide (hereinafter sometimes referred to as compound (I-13)) were obtained (yield 80%).

[0266] [ka]

[0267] <Identification of compound (I-13)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1009 Exact Mass: 1008

[0268] (Synthesis Example 12) <Preparation of compound (I-29)> N obtained in Synthesis Example 1 1 ,N 2 -Bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-anhydride (5.0 parts), 2-bromobutane (Tokyo Chemical Industry Co., Ltd.) (6.1 parts), 2-butanol (Tokyo Chemical Industry Co., Ltd.) (4.0 parts), and N,N-dimethylformamide (Kanto Chemical Co., Ltd.) (70 parts) were added and stirred at 23°C for 1 hour. Furthermore, 1,8-diazabicyclo[5.4.0]-7-undecene (Tokyo Chemical Industry Co., Ltd.) (4.6 parts) was added dropwise and stirred at 60°C for 6 hours. The resulting mixture was concentrated, and 30 parts of methanol were added, resulting in the formation of a yellow precipitate. The mixture containing this yellow precipitate was filtered, and the residue after filtration was washed with 5 parts of methanol. The resulting residue was dried under reduced pressure at 60°C and purified with a silica gel column (solvent: chloroform), yielding N 1 ,N 2 As a result, 5.0 parts of -bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-bis(2-butyl ester) (hereinafter, sometimes referred to as compound (I-29)) were obtained (yield 86%).

[0269] [ka]

[0270] <Identification of compound (I-29)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 935 Exact Mass: 934

[0271] (Synthesis Example 13) <Preparation of compound (I-30)> The same procedure as in Synthesis Example 12 was repeated to obtain N-bromo-2-ethylhexane (manufactured by Tokyo Chemical Industry Co., Ltd.) represented by the formula (I-30), except that 6.1 parts of 2-bromobutane were replaced with 8.2 parts of 1-bromo-2-ethylhexane (manufactured by Tokyo Chemical Industry Co., Ltd.) and 4.0 parts of 2-butanol were replaced with 6.7 parts of 2-ethylhexyl alcohol (manufactured by Tokyo Chemical Industry Co., Ltd.). 1 ,N 2 As a result, 4.9 parts of bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-bis(2-ethylhexyl ester) (hereinafter sometimes referred to as compound (I-30)) were obtained (yield 75%).

[0272] [ka]

[0273] <Identification of compound (I-30)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1048 Exact Mass: 1047

[0274] (Synthesis Example 14) <Preparation of compound (I-9)> N obtained in Synthesis Example 3 1 ,N 2-bis(3-pentyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-anhydride 4.0 parts, 2-bromobutane (Tokyo Chemical Industry Co., Ltd.) 6.3 parts, 2-butanol (Tokyo Chemical Industry Co., Ltd.) 4.1 parts, N,N-dimethylformamide (Kanto Chemical Co., Ltd.) 56 parts were added and stirred at 23 ° C. for 1 hour. 1,8-diazabicyclo[5.4.0]-7-undecene (Tokyo Chemical Industry Co., Ltd.) 4.7 parts was added dropwise and stirred at 60 ° C. for 9 hours. The resulting mixture was concentrated, and 31 parts of methanol were added, resulting in the formation of a yellow precipitate. The mixture containing this yellow precipitate was filtered, and the residue after filtration was washed with 4 parts of methanol. The resulting residue was dried under reduced pressure at 60°C and purified with a silica gel column (solvent: chloroform), yielding N 1 ,N 2 As a result, 4.1 parts of bis(3-pentyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-bis(2-butyl ester) (hereinafter sometimes referred to as compound (I-9)) were obtained (yield 84%).

[0275] [ka]

[0276] <Identification of compound (I-9)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 755 Exact Mass: 754

[0277] (Synthesis Example 15) <Preparation of compound (I-75)> The same procedure as in Synthesis Example 12 was repeated to prepare N-bromohexane represented by the formula (I-75), except that 6.1 parts of 2-bromobutane were replaced with 7.3 parts of 1-bromohexane (manufactured by Tokyo Chemical Industry Co., Ltd.) and 4.0 parts of 2-butanol were replaced with 5.4 parts of 1-hexanol (manufactured by Tokyo Chemical Industry Co., Ltd.). 1 ,N 2-Bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-bis(1-hexyl ester) (hereinafter sometimes referred to as compound (I-75)) was obtained in an amount of 4.3 parts (yield 70%).

[0278] [ka]

[0279] <Identification of compound (I-75)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 991 Exact Mass: 990

[0280] (Synthesis Example 16) <Preparation of compound (I-81)> The same procedure as in Synthesis Example 12 was repeated to obtain N-bromotetradecane represented by the formula (I-81), except that 6.1 parts of 2-bromobutane were replaced with 12 parts of 1-bromotetradecane (manufactured by Tokyo Chemical Industry Co., Ltd.) and 4.0 parts of 2-butanol were replaced with 11 parts of 1-tetradecanol (manufactured by Tokyo Chemical Industry Co., Ltd.). 1 ,N 2 -Bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-bis(1-tetradecyl ester) (hereinafter sometimes referred to as compound (I-81)) was obtained in an amount of 5.6 parts (yield 75%).

[0281] [ka]

[0282] <Identification of compound (I-81)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1215 Exact Mass: 1214

[0283] (Synthesis Example 17) <Preparation of compound (I-82)> The same procedure as in Synthesis Example 12 was repeated to prepare N-bromohexadecane represented by the formula (I-82), except that 6.1 parts of 2-bromobutane were replaced with 13 parts of 1-bromohexadecane (manufactured by Tokyo Chemical Industry Co., Ltd.) and 4.0 parts of 2-butanol were replaced with 13 parts of 1-hexadecanol (manufactured by Tokyo Chemical Industry Co., Ltd.). 1 ,N 2 As a result, 5.6 parts of bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-bis(1-hexadecyl ester) (hereinafter, sometimes referred to as compound (I-82)) were obtained (yield 71%).

[0284] [ka]

[0285] <Identification of compound (I-82)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1271 Exact Mass: 1270

[0286] (Synthesis Example 18) <Preparation of compound (I-87)> The same procedure as in Synthesis Example 12 was repeated to obtain N-(1-methylphenyl)-N-phenyl-2-propanediol represented by the formula (I-87), except that 6.1 parts of 2-bromobutane were replaced with 7.5 parts of benzyl bromide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 4.0 parts of 2-butanol were replaced with 5.7 parts of benzyl alcohol (manufactured by Tokyo Chemical Industry Co., Ltd.). 1 ,N 2 As a result, 5.0 parts of -bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-bis(dibenzyl ester) (hereinafter sometimes referred to as compound (I-87)) were obtained (yield 80%).

[0287] [ka]

[0288] <Identification of compound (I-87)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1003 Exact Mass: 1002

[0289] (Synthesis Example 19) <Preparation of compound (I-85)> The same procedure as in Synthesis Example 12 was repeated to obtain N-methyl-N-cyclohexylmethyl bromide represented by the formula (I-85), except that 6.1 parts of 2-bromobutane were replaced with 7.8 parts of cyclohexylmethyl bromide (manufactured by Tokyo Chemical Industry Co., Ltd.) and 4.0 parts of 2-butanol were replaced with 6.1 parts of cyclohexylmethanol (manufactured by Tokyo Chemical Industry Co., Ltd.). 1 ,N 2 -bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexanecarboxylic acid-2,3,8,9-bisimide-11,12-bis(dicyclohexylmethyl ester) (hereinafter sometimes referred to as compound (I-85)) was obtained in an amount of 4.1 parts (yield 66%).

[0290] [ka]

[0291] <Identification of compound (I-85)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1015 Exact Mass: 1014

[0292] (Synthesis Example 20) <Preparation of Compound INT>

[0293] [ka]

[0294] 10 parts of 1,6,7,12-tetrachloro-3,4,9,10-perylene dianhydride (manufactured by CombiChem Co., Ltd.), 13 parts of 2,6-diisopropylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.), and 188 parts of propionic acid were added and stirred under reflux for 20 hours. When 50 parts of water were added while keeping the obtained mixture at 20°C or less, an orange precipitate was generated. The mixture containing this orange precipitate was filtered, and the residue after filtration was washed with 200 parts of water and 100 parts of methanol. The obtained residue was dried under reduced pressure at 60°C to obtain 12 parts of an intermediate compound (hereinafter sometimes referred to as INT) (yield 75%).

[0295] <Identification of compound INT> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 847 Exact Mass: 846

[0296] (Synthesis Example 21) <Preparation of compound (II-16)> 5.0 parts of the produced INT, 1.5 parts of 4-chlorophenol (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.1 parts of 4-tert-butylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.), 11 parts of potassium carbonate (manufactured by Kanto Chemical Co., Ltd.), and 295 parts of N-methylpyrrolidone (manufactured by Kanto Chemical Co., Ltd.) were added and stirred at 130°C for 13 hours. While keeping the obtained mixture at 20°C or less, 29 parts of 37% hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) and 142 parts of water prepared in advance were added, resulting in the formation of a dark red precipitate. The mixture containing this dark red precipitate was filtered, and the residue after filtration was washed with 300 parts of water and 150 parts of methanol. The obtained residue was dried under reduced pressure at 60°C to obtain 6.1 parts of a compound represented by formula (II-16) (hereinafter sometimes referred to as compound (II-16)) (yield 81%).

[0297] [ka]

[0298] <Identification of compound (II-16)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H]+ 1237 Exact Mass: 1236

[0299] (Synthesis Example 22) <Preparation of Lumogen (registered trademark) F Yellow 083> Lumogen (registered trademark) F Yellow 083 represented by the following formula (x) was synthesized according to the description in JP-A-60-203650.

[0300] [Chemical formula]

[0301] The compound represented by the following formula (II-3) (hereinafter sometimes referred to as compound (II-3)) was obtained from Tokyo Chemical Industry Co., Ltd.

[0302] [Chemical formula]

[0303] (Synthesis Example 23) <Preparation of Resin B1> An appropriate amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel, and a stirrer and replaced with a nitrogen atmosphere. 280 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80 °C while stirring. Then, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 2,6 dec-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6A mixed solution of 289 parts of a mixture of decan-9-yl acrylate (content ratio 1:1 by molar ratio) and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a solution of 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After completion of the dropwise addition, the mixture was kept at 80°C for 4 hours and then cooled to room temperature to obtain a copolymer (resin B1) solution with a solid content of 35.1% and a viscosity of 125 mPa s measured with a Brookfield viscometer (23°C). The weight average molecular weight Mw of the resulting copolymer was 9.2×10 3 The resin B1 had a polydispersity of 2.08 and an acid value calculated as a solid content of 77 mg-KOH / g.

[0304] [ka]

[0305] <Example 1> (1) Solubility test of the compound in a solvent (propylene glycol monomethyl ether acetate; hereinafter sometimes referred to as PGMEA) Approximately 50 mg of solute (compound represented by formula (I-23)) was weighed and placed in a 20 mL screw tube. Approximately 500 mg of solvent (PGMEA) was added to this, and the total amount of solute and solvent was weighed. After stirring for 30 minutes with a mix rotor in a thermostatic bath at 20 ° C, if dissolution was confirmed visually, the value calculated from the mass of the solute relative to the total mass of the solute and solvent was taken as the solubility. If the solute did not dissolve, 500 mg of solvent was added at a time until dissolution occurred, and each time the solvent was added, stirring was continued for 30 minutes with a mix rotor in a thermostatic bath at 20 ° C., and the value calculated from the mass of the solute relative to the total mass of the solute and solvent when dissolution was confirmed visually was taken as the solubility. The results are shown in Table 5. (2) Preparation of Coloring Composition The components were mixed in the following ratio to obtain colored composition 1. (A) Colorant: 2.6 parts of a compound represented by formula (I-23) (B) Resin: 58 parts of resin B1 solution (E) Solvent: 420 parts of propylene glycol monomethyl ether acetate

[0306] (3) Preparation of Colored Curable Resin Composition Next, the components were mixed in the following ratio to obtain a colored curable resin composition 1. Coloring composition 1 480.6 parts (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 40 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 2 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.15 parts

[0307] (4) Preparation of colored coating film The colored curable resin composition was applied by spin coating onto a 5 cm square glass substrate (Eagle XG; Corning Incorporated) so that the film thickness after post-baking would be 1.7 to 2 μm, and then pre-baked at 100° C. for 3 minutes to form a colored curable resin composition layer. After cooling, the colored curable resin composition layer formed on the substrate was exposed to light at 80 mJ / cm 2 in the air using an exposure machine (TME-150RSK; Topcon Corporation). 2 After the light irradiation, the coating was post-baked in an oven at 230° C. for 30 minutes to obtain a colored coating film.

[0308] (5) Fluorescence intensity measurement The fluorescence spectrum of the resulting colored coating film was measured using a fluorescence spectrophotometer (FluoroMAX-3; Horiba, Ltd.) (excitation slit 5, fluorescence slit 10, excitation wavelength 460 nm). The fluorescence intensity at the fluorescence wavelength was determined. The fluorescence wavelength here refers to the wavelength at which the intensity of the fluorescence spectrum is maximum (peak top of the fluorescence spectrum). The fluorescence intensity means relative fluorescence intensity, and the fluorescence intensity observed here was evaluated with the maximum fluorescence intensity of Comparative Example 4 set to 1000. A maximum fluorescence intensity of more than 1000 means that the fluorescence intensity is higher than that of the colored coating film of Comparative Example 1. The results are shown in Table 5.

[0309] (6) Heat resistance test The resulting colored coating film was heated in an oven in an air atmosphere at 230°C for 180 minutes. The color difference ΔE of the colored coating film before and after the heat resistance test * ab was measured using a colorimeter (OSP-SP-200; manufactured by OLYMPUS). * The smaller the value of ab, the smaller the color change. The results are shown in Table 5.

[0310] (7) Light fastness test An ultraviolet ray cut filter (COLORED OPTICAL GLASS L38; manufactured by Hoya Co., Ltd.; cuts light of 380 nm or less) was placed on the obtained colored coating film, and the film was irradiated with xenon lamp light for 48 hours using a light resistance tester (SUNTEST CPS+; manufactured by Toyo Seiki Co., Ltd.). The color difference ΔE of the colored coating film before and after the light resistance test was * ab was measured using a colorimeter (OSP-SP-200; manufactured by OLYMPUS). * The smaller the value of ab, the smaller the color change.

[0311] <Examples 2 to 18 and Comparative Example 1> Instead of 2.6 parts of compound (I-23), 2.6 parts of compound (I-3) (Example 2), 2.6 parts of compound (I-22) (Example 3), 2.6 parts of compound (I-24) (Example 4), 2.6 parts of compound (I-25) (Example 5), 2.6 parts of compound (I-26) (Example 6), 2.6 parts of compound (I-27) (Example 7), 2.6 parts of compound (I-28) (Example 8), 2.6 parts of compound (I-12) (Example 9), 2.6 parts of compound (I-13) (Example 10), 2.6 parts of compound (I-29) (Example 11), 2.6 parts of compound (I-30) (Example 12), 2.6 parts of compound (I-9) (Example 13), 2.6 parts of compound (I-21) (Example 14), 2.6 parts of compound (I-75) (Example 15), 2.6 parts of compound (I-81) (Example 16), 2.6 parts of compound (I-82) (Example 17), 2.6 parts of compound (I-90) (Example 18), or 2.6 parts of Lumogen® F Yellow 083 (Comparative Example 1) A colored curable resin composition was obtained and a colored coating film was produced in the same manner as in Example 1, except that the above was used as the colorant. Table 5 shows the solubility in PGMEA of the compound used as the colorant in each Example, the fluorescence measurement results (maximum fluorescence intensity, fluorescence wavelength) of each colored coating film, and the heat resistance test results.

[0312] <Example 19> The components were mixed in the following ratio to obtain colored composition 19. (A) Colorant: 1.3 parts of a compound represented by formula (I-23) 2.6 parts of compound represented by formula (II-16) (B) Resin: 54 parts of resin B1 solution (E) Solvent: 420 parts of propylene glycol monomethyl ether acetate A colored curable resin composition was obtained and a colored coating film was produced in the same manner as in Example 1, except that the colored composition 19 was used instead of the colored composition 1. The fluorescence measurement results (maximum fluorescence intensity, fluorescence wavelength) and the light resistance test results for each colored coating film are shown in Table 6.

[0313] <Examples 20 to 36 and Comparative Example 2> Instead of 1.3 parts of compound (I-23), 1.3 parts of compound (I-3) (Example 20), 1.3 parts of compound (I-22) (Example 21), 1.3 parts of compound (I-24) (Example 22), 1.3 parts of compound (I-25) (Example 23), 1.3 parts of compound (I-26) (Example 24), 1.3 parts of compound (I-27) (Example 25), 1.3 parts of compound (I-28) (Example 26), 1.3 parts of compound (I-12) (Example 27), 1.3 parts of compound (I-13) (Example 28), 1.3 parts of compound (I-29) (Example 29), 1.3 parts of compound (I-30) (Example 30), 1.3 parts of compound (I-9) (Example 31), 1.3 parts of compound (I-21) (Example 32), 1.3 parts of compound (I-75) (Example 33), 1.3 parts of compound (I-81) (Example 34), 1.3 parts of compound (I-85) (Example 35), 1.3 parts of compound (I-87) (Example 36), or 1.3 parts of compound Lumogen® F Yellow 083 (Comparative Example 2) A colored curable resin composition was obtained and a colored coating film was produced in the same manner as in Example 19, except that the above was used as the colorant. The fluorescence measurement results (maximum fluorescence intensity, fluorescence wavelength) and light resistance test results for each colored coating film are shown in Table 6.

[0314] <Example 37> The components were mixed in the following proportions to obtain colored composition 37. (A) Colorant: 1.3 parts of a compound represented by formula (I-23) 2.6 parts of compound represented by formula (II-3) (B) Resin: 54 parts of resin B1 solution (E) Solvent: 420 parts of propylene glycol monomethyl ether acetate A colored curable resin composition was obtained and a colored coating film was produced in the same manner as in Example 1, except that the colored composition 37 was used instead of the colored composition 1. The fluorescence measurement results (maximum fluorescence intensity, fluorescence wavelength) and the light resistance test results for each colored coating film are shown in Table 6.

[0315] <Examples 38 to 40 and Comparative Example 3> Instead of 1.3 parts of compound (I-23), 1.3 parts of compound (I-30) (Example 38), 1.3 parts of compound (I-75) (Example 39), 1.3 parts of compound (I-82) (Example 40), or 1.3 parts of compound Lumogen® F Yellow 083 (Comparative Example 3) A colored curable resin composition was obtained and a colored coating film was produced in the same manner as in Example 37, except that the colored coating film was produced using the above-mentioned compound as the colorant. The fluorescence measurement results (maximum fluorescence intensity, fluorescence wavelength) and the light resistance test results for each colored coating film are shown in Table 6.

[0316] <Comparative Example 4> Instead of 2.6 parts of compound (I-23), Compound (II-16) of part 2.6 As a colorant, a colored curable resin composition was obtained and a colored coating film was produced in the same manner as in Example 1. The fluorescence measurement results (maximum fluorescence intensity, fluorescence wavelength) and the light resistance test results for each colored coating film are shown in Table 6.

[0317] [Table 5]

[0318] [Table 6]

[0319] From the above results, it was found that the colored coating film formed from the benzoperylene compound and the colored curable resin composition of the present invention has excellent fluorescence intensity. It was also found that the benzoperylene compound of the present invention has high solubility in a solvent (PGMEA) and good solubility. It was also found that the colored coating film formed from the colored curable resin composition of the present invention has excellent heat resistance and light resistance.

Claims

1. Contains a colorant, a resin, a polymerizable compound, and a polymerization initiator, the colorant contains a benzoperylene compound and further contains a perylene compound represented by formula (II-16) or formula (II-3), The colored curable resin composition is a copolymer having a structural unit derived from at least one monomer (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides, and a structural unit derived from a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond. 【Chemistry 1】 【Chemistry 2】

2. The colored curable resin composition according to claim 1 , wherein the benzoperylene compound is a compound represented by formula (I): 【Chemistry 3】 [In formula (I), R 1 and R 2 represent, independently of each other, a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, an aromatic heterocyclic group having 1 to 30 carbon atoms which may have a substituent, or a group in which the above-mentioned hydrocarbon group which may have a substituent and the above-mentioned aromatic heterocyclic group which may have a substituent are bonded together. R 3 ~R 10 are each independently a hydrogen atom, *-R 11 , *-O-R 11 , *-CO-O-R 11 , a halogen atom, a hydroxy group, a carboxy group or a nitro group. R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 7 and R 8 , R 8 and R 9 and R 9 and R 10 are each independently *-CO-O-CO-* or *-CO-N(R 11 ) may form a ring containing --CO--*. R 11 represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent; R 11 When there are multiple, they may be different from each other. * represents a bond.

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

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

Images