Compound, colorant, and colored resin composition

Abstract

To provide a colored resin composition capable of forming a color filter excellent in light fastness, a colorant contained in the colored resin composition, and a benzoperylene compound useful as a dye.SOLUTION: The colorant comprises at least two compounds represented by formula (I), where the two compounds represented by formula (I) differ from each other at least in R1 in the formula (I).SELECTED DRAWING: None

Description

[Technical field]

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

[0002] The colored resin composition is used for producing a color filter used in a display device such as a liquid crystal display device, an electroluminescent display device, a plasma display device, etc. Such a colored resin composition contains a colorant to obtain a desired color tone, etc., and a perylene compound represented by the following formula (x) is known as a colorant (Non-Patent Document 1).

[0003] [ka] [Prior art documents] [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 inventors have found that a color filter formed from a colored resin composition using the conventionally known perylene compound as a colorant may not have sufficient light resistance. Therefore, an object of the present invention is to provide a colored resin composition capable of forming a color filter having excellent light resistance, a colorant contained in the colored resin composition, and a benzoperylene compound useful as a dye. [Means for solving the problem]

[0006] The gist of the present invention is as follows. [1] A composition comprising at least two compounds represented by formula (I), Each of the two compounds represented by formula (I) comprises at least one compound represented by formula (I) R 1 Colorants which are compounds different from each other. [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, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -OCO- or -COO-. R 3 and R 8 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 combination thereof, in which -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -OCO- or -COO-. R 4 , R 5 , R 6 , R 7 , R 9 and R 10 are each independently a hydrogen atom, -R 11 , a halogen atom, a hydroxy group, a carboxy group or a nitro group. R 4 and R 5 , R 5 and R 6 and R 6 and R 7 are combined together to form -R 12 -CO-O-CO-R 13 -or-R 12 -CO-N(R 11 )-CO-R 13 - may form a group represented by the formula: R 11R represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -OCO- or -COO-. 11 When there are multiple, they may be the same or different. R 12 and R 13 R each independently represent a single bond or a divalent hydrocarbon group having 1 to 15 carbon atoms which may have a substituent, and -CH2- contained in the divalent hydrocarbon group may be replaced by -O-, -CO-, -OCO- or -COO-. 12 If there are multiple, they may be the same or different, and R 13 When there are multiple, they may be the same or different. [2] At least two compounds selected from the group consisting of compounds represented by formula (Ia), compounds represented by formula (Ib), and compounds represented by formula (Ic) are used as the compound represented by formula (I). (i) a combination of a compound represented by formula (Ia) and a compound represented by formula (Ib); (ii) a combination of a compound represented by formula (Ia) and a compound represented by formula (Ic), or (iii) The colorant according to [1], characterized in that it contains a combination of a compound represented by formula (Ib) and a compound represented by formula (Ic). [ka] [In the formula (Ia), the formula (Ib) and the formula (Ic), R 1a , R 2a , R 1b and R 1c each independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -OCO- or -COO-. 1a and R 2a and are never the same, and R 1b and R 1c will never be the same. R 3 ~R 10 has the same meaning as above.] [3] At least one of the above (i) a combination of a compound represented by formula (Ia) and a compound represented by formula (Ib) and the above (ii) a combination of a compound represented by formula (Ia) and a compound represented by formula (Ic) is satisfied; (i) When a combination of a compound represented by formula (Ia) and a compound represented by formula (Ib) is satisfied, R 1a and R of formula (Ib) 1b is the same as (ii) When a combination of a compound represented by formula (Ia) and a compound represented by formula (Ic) is satisfied, R 2a and R in formula (Ic) 1c The colorant according to [2], wherein [4] A composition comprising at least one of a compound represented by formula (Ia), a compound represented by formula (Ib), and a compound represented by formula (Ic), In the total amount of the compound represented by formula (Ia), the compound represented by formula (Ib) and the compound represented by formula (Ic), The content of the compound represented by formula (Ia) is 35 mol % or more and 65 mol % or less, The content of the compound represented by formula (Ib) is 15 mol % or more and 35 mol % or less, The colorant according to [2] or [3], wherein the content of the compound represented by formula (Ic) is 15 mol % or more and 35 mol % or less. [5] The colorant according to any one of [1] to [4], further comprising a perylene compound. [6] A colored resin composition comprising the colorant and resin according to any one of [1] to [5]. [7] The colored resin composition according to [6], further comprising a polymerizable compound and a polymerization initiator. [8] The colored resin composition according to [6] or [7], further comprising a solvent. [9] A color filter formed from the colored resin composition according to any one of [6] to [8].

[10] A display device comprising the color filter according to [9].

[11] A compound represented by formula (Ia). [ka] [In formula (Ia), R 1a and R 2a each independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -OCO- or -COO-. 1a and R 2a will never be the same. R 3 and R 8 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 formed by combining these, and -CH2- contained in the hydrocarbon group and -CH2- contained in the combined group may be replaced by -O-, -CO-, -OCO- or -COO-. R 4 , R 5 , R 6 , R 7 , R 9 and R 10 are each independently a hydrogen atom, -R 11 , a halogen atom, a hydroxy group, a carboxy group or a nitro group. R 4 and R 5 , R 5 and R 6 and R 6 and R 7 are combined together to form -R 12 -CO-O-CO-R 13 -or-R 12 -CO-N(R 11 )-CO-R 13 - may form a group represented by the formula: R 11 R represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -OCO- or -COO-. 11 When there are multiple, they may be the same or different. R 12 and R 13 R each independently represent a single bond or a divalent hydrocarbon group having 1 to 15 carbon atoms which may have a substituent, and -CH2- contained in the divalent hydrocarbon group may be replaced by -O-, -CO-, -OCO- or -COO-. 12 If there are multiple, they may be the same or different, and R 13 When there are multiple, they may be the same or different. Effect of the Invention

[0007] According to the present invention, there are provided a colored resin composition, a colorant, and a compound that can be used to form a color filter having superior light resistance compared to a colored resin composition containing a conventional perylene compound as a colorant. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0008] The colorant of the present invention (hereinafter, may be referred to as colorant (A)) contains at least two compounds represented by formula (I) (hereinafter, may be referred to as compound (I)). Each of the two compounds (I) contains at least R 1 are different compounds.

[0009] <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), and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -OCO- or -COO-. R 3 and R 8represent, 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 combining these, in which -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -OCO- or -COO-. R 4 , R 5 , R 6 , R 7 , R 9 and R 10 are each independently a hydrogen atom, -R 11 , a halogen atom, a hydroxy group, a carboxy group or a nitro group. R 4 and R 5 , R 5 and R 6 and R 6 and R 7 are combined together to form -R 12 -CO-O-CO-R 13 -or-R 12 -CO-N(R 11 )-CO-R 13 - may form a group represented by the formula: R 11 R represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent (A1), and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -OCO- or -COO-. 11 When there are multiple, they may be the same or different. R 12 and R 13 R each independently represent a single bond or a divalent hydrocarbon group having 1 to 15 carbon atoms which may have a substituent (A1), and -CH2- contained in the divalent hydrocarbon group may be replaced by -O-, -CO-, -OCO- or -COO-. 12 If there are multiple, they may be the same or different, and R 13 When there are multiple, they may be the same or different.

[0010] R 1 , R 2 , R 3 , R8 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.

[0011] R 1 , R 2 , R 3 , R 8 and R 11 Examples 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 (3-methyl)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 (3-methyl)pentyl group, a (1-ethyl)pentyl group, a (2- (ethyl)pentyl group, (3-ethyl)pentyl group, (1-propyl)pentyl group, (1-butyl)pentyl group, isohexyl group, (5-methyl)hexyl group, (1-ethyl)hexyl group, (2-ethyl)hexyl group, (1-butyl)hexyl group, (1-pentyl)hexyl group, (3-ethyl)heptyl group, (1-hexyl)heptyl group, (1-heptyl)octyl group , (1-octyl)nonyl group, and other branched alkyl groups; vinyl group, 1-propenyl group, 2-propenyl group (allyl group), (1-methyl)ethenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1,3-butadienyl group, (1-(2-propenyl))ethenyl group, (1,2-dimethyl)propenyl group, 2-pentenyl group, and other alkenyl groups; etc. 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 15. 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 15.

[0012] R 1 , R 2 , R 3 , R 8 and R 11 Examples 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.

[0013] R 1 , R 2 , R 3 , R 8 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.

[0014] R 1 , R 2 , R 3 , R 8 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, 1-methyl-1-phenylethyl, 1-naphthylmethyl, and 2-naphthylmethyl; 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, 2,4,6-trimethylphenyl, 4-vinylphenyl, o-isopropylphenyl, m-isopropylphenyl, p-isopropylphenyl, 2,3- alkylaryl groups such as a diisopropylphenyl group, a 2,4-diisopropylphenyl group, a 2,5-diisopropylphenyl group, a 2,6-diisopropylphenyl group, a 3,5-diisopropylphenyl group, a 2,4,6-triisopropylphenyl group, a 4-butylphenyl group, an o-tert-butylphenyl group, a m-tert-butylphenyl group, a p-tert-butylphenyl group, a 2,6-di(tert-butyl)phenyl group, a 3,5-di(tert-butyl)phenyl group, a 3,6-di(tert-butyl)phenyl group, a 4-tert-butyl-2,6-dimethylphenyl group, a 4-pentylphenyl group, a 4-octylphenyl group, a 4-(2,4,4-trimethyl-2-pentyl)phenyl group, a 2-dodecylphenyl group, a 3-dodecylphenyl group, and a 4-dodecylphenyl group;Examples of the aryl group include an aryl group having an alkanediyl group bonded thereto, such as a 2,3-dihydro-4-indenyl group, a 1,2,3,5,6,7-hexahydro-4-s-indacenyl group, an 8-methyl-1,2,3,5,6,7-hexahydro-4-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 with an alicyclic hydrocarbon group, and examples thereof include a 1-methylcyclopropyl group, a 2-methylcyclopentyl 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, and a 2,5-dimethylcyclohexyl group. alicyclic hydrocarbon groups to which one or more alkyl groups are bonded, such as a 2,6-dimethylcyclohexyl group, a 3,4-dimethylcyclohexyl group, a 3,5-dimethylcyclohexyl group, a 2,2-dimethylcyclohexyl group, a 3,3-dimethylcyclohexyl group, a 4,4-dimethylcyclohexyl group, a 2,4,6-trimethylcyclohexyl group, a 2,2,6,6-tetramethylcyclohexyl group, a 3,3,5,5-tetramethylcyclohexyl group, a 4-pentylcyclohexyl group, a 4-octylcyclohexyl group, or a 4-cyclohexylcyclohexyl group;Examples of such alkyl groups include alkyl groups having one or more alicyclic hydrocarbon groups bonded thereto, such as a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclobutylethyl group, a cyclopentylmethyl group, a cyclopentylethyl group, a cyclohexylmethyl group, a 2-methylcyclohexylmethyl group, a cyclohexylethyl group, and an adamantylmethyl group. The number of carbon atoms in the group obtained by combining two or more chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups is preferably 4 to 28, more preferably 5 to 25, and even more preferably 6 to 20.

[0015] R 1 , R 2 , R 3 , R 8 and R 11 When -CH2- in the hydrocarbon group represented by the formula (I) is replaced with -O-, -CO-, -OCO-, or -COO-, the number of such replacements may be one or more. When -CH2- in the hydrocarbon group is replaced with -O-, -CO-, -OCO-, or -COO-, the number of carbon atoms before replacement is the number of carbon atoms in the hydrocarbon group. R 1 , R 2 , R 3 , R 8 and R 11 Specific examples of the group in which -CH2- in the hydrocarbon group represented by the formula (Y-1) to (Y-25) are replaced with -O-, -CO-, -OCO- or -COO- include groups represented by the formulas (Y-1) to (Y-25) below. * represents a bond.

[0016] [ka]

[0017] R 12 and R 13 As the divalent hydrocarbon group having 1 to 15 carbon atoms represented by the formula: 1 , R 2 , R 3 , R 8 and R 11 (However, this does not include examples of a hydrocarbon group having 16 or more carbon atoms.) and the like, in which one hydrogen atom contained in the formula (I) serves as a bond. The number of carbon atoms in the divalent hydrocarbon group is preferably 1 to 10, more preferably 1 to 8, and even more preferably 1 to 5. The divalent hydrocarbon group is preferably a divalent saturated chain hydrocarbon group, and more preferably a linear or branched alkanediyl group. Examples of the divalent hydrocarbon group include alkanediyl groups such as a methylene group, an ethylene group, a propylene group, and a butylene group.

[0018] R 12 and R 13 When -CH2- contained in the divalent hydrocarbon group represented by the formula (I) is replaced with -O-, -CO-, -OCO- or -COO-, the number of the -CH2- may be 1 or 2 or more. When -CH2- contained in the hydrocarbon group is replaced with -O-, -CO-, -OCO- or -COO-, the number of carbon atoms before the replacement is regarded as the number of carbon atoms of the divalent hydrocarbon group. R 12 and R 13 Specific examples of the divalent hydrocarbon group represented by the formula (Y-1) to (Y-25) in which -CH2- is replaced with -O-, -CO-, -OCO- or -COO- include groups in which one hydrogen atom in the group represented by the formula (Y-1) to (Y-25) is bonded.

[0019] R 3 and R 8 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, or a sulfur atom. 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, and a carbazolyl group. The number of carbon atoms in the aromatic heterocyclic group is preferably 2 to 25, more preferably 3 to 20, and further preferably 3 to 15.

[0020] R 3 and R 8The combined group formed by the bonding of the hydrocarbon group and the aromatic heterocyclic group represented by the formula (I) may be a group in which two or more of the above-listed hydrocarbon groups and aromatic heterocyclic groups are bonded together, for example, a group in which at least one selected from a chain-like hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group is bonded to an aromatic heterocyclic group, and in the group formed by the bonding, the chain-like hydrocarbon group may be bonded as a divalent group (for example, an alkanediyl group). Examples of the group formed by the bonding of 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 the combination of the hydrocarbon group and the aromatic heterocyclic group is preferably 4 to 30, more preferably 6 to 30, and even more preferably 10 to 30.

[0021] R 1 , R 2 , R 3 , R 8 and R 11 A hydrocarbon group having 1 to 30 carbon atoms represented by the formula: 3 and R 8 and an aromatic heterocyclic group having 1 to 30 carbon atoms represented by the following formula: 12 and R 13Examples of the substituent (A1) which the divalent hydrocarbon group having 1 to 15 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; 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; a phenylsulfoxy group, a 1-naphthylthio group, arylsulfoxy groups having 6 to 20 carbon atoms, such as a 2-naphthylsulfoxy group, and the like; 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, and a triethylamino group; arylamino groups having 6 to 20 carbon atoms, such as a monophenylamino group, a diphenylamino group, and a triphenylamino group; aralkylamino groups having 7 to 20 carbon atoms, such as a benzylamino group; carboxy groups; and carbamoyl groups.

[0022] The halogen atom includes a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, etc. From the viewpoint of synthesis, a chlorine atom and a bromine atom are preferred.

[0023] R 1 , R 2 , R 3 , R 8 and R 11 Specific examples of the hydrocarbon group having 1 to 30 carbon atoms which may have a substituent (A1) represented by the following formulae (D-1) to (D-37) and (G-1) to (G-24) are given below. * represents a bond.

[0024] [ka]

[0025] [ka]

[0026] From the viewpoint of improving the light resistance of the resulting color filter, R 1 and R 2 R is preferably, independently of each other, a saturated chain hydrocarbon group which may have a substituent (A1), a group in which an aromatic hydrocarbon group which may have a substituent (A1) is combined with a chain hydrocarbon group, or a group in which a chain hydrocarbon group which may have a substituent (A1) is combined with an alicyclic hydrocarbon group, and in any of these groups, it is preferable that -CH2- contained in the hydrocarbon group is not replaced with -O-, -CO-, -OCO- or -COO-. 1 and R 2 are more preferably, independently of each other, a saturated chain hydrocarbon group having 1 to 15 carbon atoms, a group in which an aromatic hydrocarbon group having 6 to 12 carbon atoms is combined with a chain hydrocarbon group having 1 to 10 carbon atoms, or a group in which a chain hydrocarbon group having 1 to 10 carbon atoms is combined with an alicyclic hydrocarbon group having 3 to 12 carbon atoms, and even more preferably, a saturated chain hydrocarbon group having 3 to 13 carbon atoms, a group in which an aromatic hydrocarbon group having 6 to 10 carbon atoms is combined with a chain hydrocarbon group having 1 to 5 carbon atoms, or a group in which a chain hydrocarbon group having 1 to 5 carbon atoms is combined with an alicyclic hydrocarbon group having 5 to 10 carbon atoms. 1 and R 2 are preferably, independently of one another, a group represented by any one of the above formulas (D-1) to (D-37), more preferably a group represented by any one of the formulas (D-3) to (D-10), or (D-12) to (D-37), even more preferably a group represented by any one of the formulas (D-4) to (D-9), or (D-22) to (D-37), and even more preferably a group represented by any one of the formulas (D-5) to (D-8), (D-28) to (D-33), or (D-36). From the viewpoint of improving the solubility of compound (I) in a solvent, R 1 and R 2 are each independently preferably a saturated chain hydrocarbon group having 1 to 15 carbon atoms, more preferably a saturated chain hydrocarbon group having 3 to 13 carbon atoms, and further preferably a linear alkyl group having 3 to 13 carbon atoms. R 1 and R 2may be the same or different, but is preferably different.

[0027] From the viewpoint of improving the light resistance of the resulting color filter, R 3 and R 8 are preferably, independently of each other, an aromatic hydrocarbon group which may have a substituent (A1), or a group combining an aromatic hydrocarbon group which may have a substituent (A1) with a chain-like hydrocarbon group, more preferably a group combining an aromatic hydrocarbon group which may have a substituent (A1) with a chain-like hydrocarbon group, even more preferably a group combining an aromatic hydrocarbon group with a chain-like hydrocarbon group, still more preferably a group combining an aromatic hydrocarbon group with a saturated chain-like hydrocarbon group, still more preferably a group combining an aromatic hydrocarbon group having 6 to 12 carbon atoms with a saturated chain-like hydrocarbon group having 1 to 8 carbon atoms, and particularly preferably a group in which a saturated chain-like hydrocarbon group is bonded to each of the two ortho positions of a phenyl group. 3 and R 8 are preferably, independently of each other, a group represented by any one of the above formulas (G-1) to (G-24), more preferably a group represented by any one of the formulas (G-1) to (G-15), even more preferably a group represented by any one of the formulas (G-5) to (G-15), still more preferably a group represented by any one of the formulas (G-5) to (G-9), (G-12) or (G-14), and particularly preferably a group represented by formula (G-8). Also, R 3 and R 8 may be the same or different, but is preferably the same.

[0028] R 4 , R 5 , R 6 , R 7 , R 9 and 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.

[0029] R4 and R 5 , R 5 and R 6 and R 6 and R 7 are bonded together to form -R 12 -CO-O-CO-R 13 Specific examples of the group represented by - include divalent groups represented by the following formulae (H-1) to (H-8). * represents R 4 and R 5 , R 5 and R 6 or R 6 and R 7 represents a bond to the benzoperylene skeleton.

[0030] [ka]

[0031] R 4 and R 5 , R 5 and R 6 and R 6 and R 7 are bonded together to form -R 12 -CO-N(R 11 )-CO-R 13 Specific examples of the group represented by - include divalent groups represented by the following formulae (H-9) to (H-16). * represents R 4 and R 5 , R 5 and R 6 or R 6 and R 7 represents a bond to the benzoperylene skeleton.

[0032] [ka]

[0033] More specifically, the group represented by formula (H-9) includes groups represented by the following formulae (H-9-1) to (H-9-16). * represents R 4 and R 5 , R 5 and R6 or R 6 and R 7 represents a bond to the benzoperylene skeleton.

[0034] [ka]

[0035] R 4 , R 5 , R 6 , R 7 , R 9 and R 10 is preferably a hydrogen atom. 4 , R 5 , R 6 , R 7 , R 9 and R 10 may be appropriately combined to form a compound having a desired absorption wavelength or fluorescence wavelength.

[0036] Specific examples of compound (I) include the compounds shown in Table 1 below.

[0037] [Table 1]

[0038] In Table 1, H represents a hydrogen atom, and D-5, D-6, D-7, D-8, D-29, D-30, D-31, D-33, D-36, and G-8 represent groups represented by the above formulae (D-5), (D-6), (D-7), (D-8), (D-29), (D-30), (D-31), (D-33), (D-36), and (G-8), respectively.

[0039] From the viewpoint of improving the light resistance of the obtained color filter, the compounds (I) are preferably the compounds (I-1) to (I-45), and more preferably the compounds (I-2) to (I-9), the compounds (I-11) to (I-17), the compounds (I-19) to (I-24), the compounds (I-26) to (I-30), the compounds (I-32) to (I-35), the compounds (I-37) to (I-39), the compounds (I-41), the compounds (I-42) and the compounds (I-44).

[0040] <Colorant (A)> The colorant (A) contains at least two compounds (I), and each of the two compounds (I) is at least one of R 1 The R of the formula (I) of the two types of compounds (I) are different from each other. 2 may be the same or different. 3 ~R 10 may be the same or different, R 3 ~R 10 It is preferable that 4 to 8 of R are the same. 3 ~R 10 More preferably, 6 to 8 of R 3 ~R 10 The number of types of the compounds (I) contained as the colorant (A) is preferably 2 or more and 6 or less, more preferably 2 or more and 5 or less, and even more preferably 2 or more and 4 or less.

[0041] The two or more compounds (I) contained as the colorant (A) are at least two compounds selected from the group consisting of a compound represented by the following formula (Ia) (hereinafter, may be referred to as compound (Ia)), a compound represented by the following formula (Ib) (hereinafter, may be referred to as compound (Ib)), and a compound represented by the following formula (Ic) (hereinafter, may be referred to as compound (Ic)). (i) a combination of a compound represented by formula (Ia) and a compound represented by formula (Ib) (hereinafter, sometimes referred to as combination (i)), (ii) a combination of a compound represented by formula (Ia) and a compound represented by formula (Ic) (hereinafter, sometimes referred to as combination (ii)); or (iii) It is preferable that the compound represented by formula (Ib) and the compound represented by formula (Ic) are contained in a combination (hereinafter, sometimes referred to as combination (iii)).

[0042] <<Compound (Ia), Compound (Ib), Compound (Ic)>> [ka] [In the formula (Ia), the formula (Ib) and the formula (Ic), R 1a , R 2a , R 1b and R 1c each independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent (A5), and -CH2- contained in the hydrocarbon group may be replaced by -O-, -CO-, -OCO- or -COO-. 1a and R 2a and are never the same, and R 1b and R 1c will never be the same. R 3 ~R 10 has the same meaning as above.]

[0043] In addition, the two R 1b are the same group, and the two R 1c are the same group.

[0044] R 1a , R 2a , R 1b and R 1c As the hydrocarbon group having 1 to 30 carbon atoms represented by the formula: 1 , R 2 , R 3 , R 8 and R11 The preferred range of the carbon number is also the same as that of the hydrocarbon group represented by the formula:

[0045] R 1a , R 2a , R 1b and R 1c When -CH2- in the hydrocarbon group represented by the formula (I) is replaced with -O-, -CO-, -OCO-, or -COO-, the number of such replacements may be one or more. When -CH2- in the hydrocarbon group is replaced with -O-, -CO-, -OCO-, or -COO-, the number of carbon atoms before replacement is the number of carbon atoms in the hydrocarbon group. R 1a , R 2a , R 1b and R 1c Examples of the hydrocarbon group represented by the formula (I) in which -CH2- is replaced by -O-, -CO-, -OCO- or -COO- include R 1 , R 2 , R 3 , R 8 and R 11 Examples thereof include the same as those in which -CH2- in the hydrocarbon group represented by the following formula is replaced with -O-, -CO-, -OCO- or -COO-.

[0046] R 1a , R 2a , R 1b and R 1c The substituent (A5) which may be possessed by the hydrocarbon group having 1 to 30 carbon atoms represented by the formula: 1 , R 2 , R 3 , R 8 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:

[0047] From the viewpoint of improving the light resistance of the resulting color filter, R 1a , R 2a , R 1b and R 1cR is preferably, independently of each other, a saturated chain hydrocarbon group which may have a substituent (A5), a group in which an aromatic hydrocarbon group which may have a substituent (A5) is combined with a chain hydrocarbon group, or a group in which a chain hydrocarbon group which may have a substituent (A5) is combined with an alicyclic hydrocarbon group, and in any of these groups, it is preferable that -CH2- contained in the hydrocarbon group is not replaced with -O-, -CO-, -OCO- or -COO-. 1a , R 2a , R 1b and R 1c are preferably, independently, a saturated chain hydrocarbon group having 1 to 15 carbon atoms, a group in which an aromatic hydrocarbon group having 6 to 12 carbon atoms is combined with a chain hydrocarbon group having 1 to 10 carbon atoms, or a group in which a chain hydrocarbon group having 1 to 10 carbon atoms is combined with an alicyclic hydrocarbon group having 3 to 12 carbon atoms, and more preferably, a saturated chain hydrocarbon group having 3 to 13 carbon atoms, a group in which an aromatic hydrocarbon group having 6 to 10 carbon atoms is combined with a chain hydrocarbon group having 1 to 5 carbon atoms, or a group in which a chain hydrocarbon group having 1 to 5 carbon atoms is combined with an alicyclic hydrocarbon group having 5 to 10 carbon atoms. From the viewpoint of improving the solubility of compound (I) in solvents, R 1a , R 2a , R 1b and R 1c are each independently preferably a saturated chain hydrocarbon group having 1 to 15 carbon atoms, more preferably a saturated chain hydrocarbon group having 3 to 13 carbon atoms, and further preferably a linear alkyl group having 3 to 13 carbon atoms. 1a , R 2a , R 1b and R 1c are preferably, independently of one another, a group represented by any one of the above formulas (D-1) to (D-37), more preferably a group represented by any one of the formulas (D-3) to (D-10), or (D-12) to (D-37), even more preferably a group represented by any one of the formulas (D-4) to (D-9), or (D-22) to (D-37), and even more preferably a group represented by any one of the formulas (D-5) to (D-8), (D-28) to (D-33), or (D-36).

[0048] R in formula (Ia) 1a and R 2a The distinction is determined by the following criteria: First priority discrimination criterion: The larger the formula weight, the higher the R 1a Let's say Second priority discrimination criterion: The one with the larger number of -CH2- is R 1a Let's say Third priority discrimination criterion: -The one with the larger number of CH3 is R 1a Let's say For example, in the case of the above compound (I-2), the pentyl group represented by formula (D-5) is R 2a and the hexyl group represented by formula (D-6) is R 1a Let us assume that.

[0049] R in formula (Ib) and formula (Ic) 1b and R 1c The distinction is determined by the following criteria: First priority discrimination criterion: The larger the formula weight, the higher the R 1b Let's say Second priority discrimination criterion: The one with the larger number of -CH2- is R 1b Let's say Third priority discrimination criterion: -The one with the larger number of CH3 is R 1b Let's say For example, in the case of the above-mentioned compounds (I-1) and (I-10), the pentyl group represented by formula (D-5) of compound (I-1) is R 1c (i.e., compound (I-1) corresponds to compound (Ic)), and the hexyl group represented by formula (D-6) of compound (I-10) corresponds to R 1b (i.e., compound (I-10) corresponds to compound (Ib)).

[0050] When the colorant (A) contains at least two compounds selected from the group consisting of the compound (Ia), the compound (Ib), and the compound (Ic) so as to satisfy at least one of the combination (i) and the combination (ii) above, when the colorant (A) contains at least two compounds selected from the group consisting of the compound (Ia), the compound (Ib), and the compound (Ic) above ... 1aand R of formula (Ib) 1b and are preferably the same, and when the combination of (ii) is contained in a satisfactory manner, R 2a and R in formula (Ic) 1c It is preferable that the above formula is the same as the formula. For example, when compound (Ia) is the above-mentioned compound (I-2), if colorant (A) includes a combination of (i) compound (Ia) and compound (Ib), compound (Ib) is preferably the above-mentioned compound (I-10).Also, when compound (Ia) is the above-mentioned compound (I-2), if colorant (A) includes a combination of (ii) compound (Ia) and compound (Ic), compound (Ic) is preferably the above-mentioned compound (I-1).

[0051] When the colorant (A) contains at least two compounds selected from the group consisting of compound (Ia), compound (Ib), and compound (Ic) so as to satisfy the combination (i) above, the content of compound (Ia) in the total amount of compound (Ia) and compound (Ib) is preferably 45 mol % or more and 85 mol % or less, more preferably 50 mol % or more and 80 mol % or less, and even more preferably 55 mol % or more and 75 mol % or less. When the colorant (A) contains at least two compounds selected from the group consisting of compound (Ia), compound (Ib), and compound (Ic) so as to satisfy the combination (ii) above, the content of compound (Ia) in the total amount of compound (Ia) and compound (Ic) is preferably 45 mol % or more and 85 mol % or less, more preferably 50 mol % or more and 80 mol % or less, and even more preferably 55 mol % or more and 75 mol % or less. When the colorant (A) contains at least two compounds selected from the group consisting of compound (Ia), compound (Ib), and compound (Ic) so as to satisfy the combination (iii) above, the content of compound (Ib) in the total amount of compound (Ib) and compound (Ic) is preferably 35 mol % or more and 65 mol % or less, more preferably 40 mol % or more and 60 mol % or less, and even more preferably 45 mol % or more and 55 mol % or less.

[0052] The colorant (A) may be any of the following compounds represented by formula (I): 1 From the viewpoint of easily producing the colorant (A) containing at least two kinds of compounds (I) each having different R 1a and R of formula (Ib) 1b and R of formula (Ia) is the same as 2a and R in formula (Ic) 1c It is more preferable that the compound (Ia), the compound (Ib) and the compound (Ic) are contained at least one kind each so that the above-mentioned formula (Ia), the formula (Ib) and the compound (Ic) are the same as each other. From the viewpoint of easily controlling the content of each compound (I) in the colorant (A), it is preferable that the colorant (A) does not contain compound (Ia) and contains at least one type each of compound (Ib) and compound (Ic).

[0053] When the colorant (A) contains one or more of each of compound (Ia), compound (Ib), and compound (Ic), the content of compound (Ia) in the total amount of compound (Ia), compound (Ib), and compound (Ic) is preferably 35 mol % or more and 65 mol % or less, more preferably 40 mol % or more and 60 mol % or less, and even more preferably 45 mol % or more and 55 mol % or less.

[0054] When the colorant (A) contains one or more of each of compound (Ia), compound (Ib), and compound (Ic), the contents of compound (Ib) and compound (Ic) are each independently preferably from 15 mol % to 35 mol %, more preferably from 18 mol % to 32 mol %, and even more preferably from 20 mol % to 30 mol %, of the total amount of compound (Ia), compound (Ib), and compound (Ic). Furthermore, when the colorant (A) contains one or more of each of compound (Ia), compound (Ib), and compound (Ic), the content ratio of compound (Ib) to compound (Ic) (compound (Ib) / compound (Ic)) is preferably 0.80 or more and 1.20 or less, more preferably 0.85 or more and 1.15 or less, and even more preferably 0.87 or more and 1.13 or less, on a molar basis.

[0055] As compound (I), compound (Ia) is particularly preferred.

[0056] Compound (I) can be produced, for example, by reacting a compound represented by the following formula (pt1) with maleic anhydride in the presence of a dehydrogenating agent to produce a compound represented by the following formula (pt1-1), and then reacting the compound represented by formula (pt1-1) with compounds represented by the following formulas (MA1-1), (MA1-2), (MA2-1) and (MA2-2) in a solvent in the presence of a base. 1 and R 2 and R are different, it is possible to simultaneously produce the compound represented by formula (I)' and the compound represented by formula (I)'' together with the compound represented by formula (I). For example, R 1 The mass of R 2 When the formula weight is greater than the above, the compound represented by formula (I) corresponds to the above-mentioned compound (Ia), the compound represented by formula (I)' corresponds to the above-mentioned compound (Ib), and the compound represented by formula (I)'' corresponds to the above-mentioned compound (Ic).

[0057] [ka] [In the formula, R 1 ~R 10 is the same as defined above. 1 and X 2 each independently represents a halogen atom.

[0058] The compound represented by formula (pt1) is, for example, N 1 ,N 2-bis(2,6-diisopropylphenyl)perylene-3,4,9,10-tetracarboxylic diimide and the like.

[0059] The amount of maleic anhydride used is usually 1 mole or more and 1,000 moles or less, preferably 1 mole or more and 800 moles or less, more preferably 1 mole or more and 600 moles or less, and even more preferably 1 mole or more and 400 moles or less, relative to 1 mole of the compound represented by formula (pt1).

[0060] The dehydrogenation agent is a dehydrogenation agent that removes hydrogen from a 6-membered ring compound to aromaticize the compound. As the dehydrogenation agent, p-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 p-chloranil and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone are more preferred.

[0061] The reaction temperature when reacting the compound represented by formula (pt1) with maleic anhydride is usually −100° C. or higher and 300° C. or lower. The reaction time when reacting the compound represented by formula (pt1) with maleic anhydride is usually 0.5 hours to 500 hours.

[0062] X 1 and X 2 Examples of the halogen atom represented by the formula (I) include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, and a bromine atom or an iodine atom is preferred.

[0063] Examples of the compounds represented by formula (MA1-1) and formula (MA2-1) include 1-pentanol, 1-hexanol, 2-ethylhexanol, 1-heptanol, 1-octanol, benzyl alcohol, and cyclohexanemethanol.

[0064] Examples of the compounds represented by formula (MA1-2) and formula (MA2-2) include 1-bromopentane, 1-iodopentane, 1-bromohexane, 1-iodohexane, 1-bromo-2-ethylhexane, 1-iodo-2-ethylhexane, 1-bromoheptane, 1-iodoheptane, 1-bromooctane, 1-iodooctane, benzyl bromide, benzyl iodide, cyclohexylmethyl bromide, and cyclohexylmethyl iodide.

[0065] The amount of the compounds represented by formula (MA1-1), formula (MA1-2), formula (MA2-1) and formula (MA2-2) used is, independently of each other, usually 1 mol to 20 mol, preferably 1 mol to 10 mol, relative to 1 mol of the compound represented by formula (pt1-1). The total amount of the compounds represented by formula (MA1-1), formula (MA1-2), formula (MA2-1) and formula (MA2-2) used is usually 5 mol to 50 mol, preferably 10 mol to 35 mol, relative to 1 mol of the compound represented by formula (pt1-1).

[0066] Examples of the base in the reaction of the compound represented by formula (pt1-1) with the compounds represented by formulae (MA1-1), (MA1-2), (MA2-1) and (MA2-2) include organic bases such as triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine, piperidine, 1,8-diazabicyclo[5.4.0]undecene and 1,5-diazabicyclo[4.3.0]nonene; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide and potassium tert-butoxide; organometallic compounds such as methyllithium, butyllithium, tert-butyllithium and phenyllithium; and inorganic bases such as sodium hydrogencarbonate, potassium hydrogencarbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide and potassium hydroxide, with organic bases being preferred.

[0067] The amount of the base used is usually 0.1 mole or more and 100 moles or less, and preferably 1 mole or more and 40 moles or less, relative to 1 mole of the compound represented by formula (pt1-1).

[0068] Examples of the solvent used in the reaction of the compound represented by formula (pt1-1) with the compounds represented by formulae (MA1-1), (MA1-2), (MA2-1) and (MA2-2) 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; and acetone. aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride, chloroform, 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, butyric acid, imidazole, etc., among which amide solvents are preferred, and N,N-dimethylformamide is more preferred.

[0069] The amount of the solvent used is usually 0.1 to 1000 parts by mass relative to 1 part by mass of the compound represented by formula (pt1-1).

[0070] The reaction temperature when reacting the compound represented by formula (pt1-1) with the compounds represented by formulae (MA1-1), (MA1-2), (MA2-1) and (MA2-2) is usually from −100° C. to 300° C. The reaction time when reacting the compound represented by formula (pt1-1) with the compounds represented by formulae (MA1-1), (MA1-2), (MA2-1) and (MA2-2) is usually from 0.5 hours to 500 hours.

[0071] After the reaction is completed, the method for extracting compound (I) is not particularly limited, and it can be extracted by various known methods. After extraction, the obtained residue may be purified by column chromatography or recrystallization. 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.

[0072] Compound (I), in particular R of formula (I) 1 A mixture of compounds (I) containing two or more compounds (I) having different ions has high solubility in solvents such as propylene glycol monomethyl ether acetate and cyclohexanone (particularly propylene glycol monomethyl ether acetate), and has good solubility. The solubility can be calculated by weighing about 50 mg of the compound or mixture of compounds (hereinafter sometimes referred to as solute) to be measured in a 20 mL screw tube, adding about 500 mg of solvent thereto, weighing the total amount of the solute and the 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 the 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 the 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)

[0073] The solubility of compound (I) in propylene glycol monomethyl ether acetate at 20° C. is preferably 0.5% by mass or more, more preferably 1.0% by mass or more, and even more preferably 1.5% by mass or more, and may be 15% by mass or less. When two or more types of compound (I) are contained as a colorant, it is preferable that the solubility of the contained compounds (I) in a mixture state is within the above range.

[0074] The content of compound (I) in the total amount of colorant (A) may be 100% by mass, and the lower limit may be, for example, 0.1% by mass or more, and is preferably 5% by mass or more, more preferably 10% by mass or more, even more preferably 20% by mass or more, even more preferably 30% by mass or more, and even more preferably 50% by mass or more.

[0075] The colorant (A) may further contain one or more perylene compounds. 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, the perylene compound is particularly preferably a compound represented by formula (II) (hereinafter, sometimes referred to as compound (II)).

[0076] <<Compound (II)>> [ka] [In formula (II), Ar 21 ~Ar 26each 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.]

[0077] Ar 21 ~Ar 26 The aryl groups represented by the following formula (1) are each independently exemplified by a phenyl group, a naphthyl group, etc., with a phenyl group being preferred.

[0078] 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.

[0079] 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.

[0080] Ar 21 ~Ar 26 The aryl group represented by the following formula (I) may or may not have one or more kinds of substituents (A3).

[0081] Ar 21 ~Ar 26 Examples of the group include groups represented by the following formulae (E-1) to (E-27), in which * represents a bond.

[0082] [ka]

[0083] From the viewpoint of improving solubility in solvents, Ar 21 and Ar 22 Preferred as Ar are groups represented by any one of formulas (E-5), (E-7), (E-8) and (E-11). From the viewpoint of improving solubility in a solvent, Ar 23 ~Ar 26 Preferred is a group represented by any one of formula (E-1), formula (E-4), formula (E-9), formula (E-10), formula (E-17) and formula (E-18).

[0084] Ar 21 ~Ar 26may all be the same or may be different. Ar 21 and Ar 22 are preferably the same.

[0085] 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. 3 , R 6 , R 8 and R 11 Examples of the hydrocarbon group include the same as those of the hydrocarbon group represented by the following formula:

[0086] R 21 ~R 24 Examples of the substituent (A4) which the hydrocarbon group having 1 to 20 carbon atoms represented by the following formula may have include the same examples as the substituent (A1) above.

[0087] 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.

[0088] R 21 ~R 24 is preferably a hydrogen atom.

[0089] Specific examples of compound (II) include the compounds shown in Table 2 below.

[0090] [Table 2]

[0091] In Table 2, 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.

[0092] As compound (II), compounds (II-1) to (II-24) are preferred, compounds (II-1) to (II-6), compounds (II-9), compounds (II-10), compounds (II-15), compounds (II-16), compounds (II-21) and compounds (II-22) are more preferred, and compounds (II-3), compounds (II-4), compounds (II-9), compounds (II-10), compounds (II-15) and compounds (II-16) are even more preferred.

[0093] Compound (II) can be produced, for example, by reacting a compound represented by the following formula (pt3), a compound represented by the following formula (AR1), and a compound represented by the following formula (AR2) in a solvent.

[0094] [ka] [In the formula, R 21 ~R 24 is the same as defined above.]

[0095] 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

[0096] An example of the compound represented by formula (pt3) is 1,6,7,12-tetrachloroperylene tetracarboxylic dianhydride.

[0097] 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.

[0098] 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.

[0099] 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 (pt3).

[0100] 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, or propionic acid is preferable.

[0101] 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 (pt3).

[0102] 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. The reaction time is usually 0.5 to 500 hours.

[0103] 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.

[0104] 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.

[0105] Furthermore, when colorant (A) contains a perylene compound, the content of the perylene compound in the total amount of compound (I) 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.

[0106] When the colorant (A) contains the compound (I) and a perylene compound, the compound (I) can also serve as a sensitizer for the perylene compound.

[0107] <<Colorant (A1)>> The colorant (A) of the present invention may contain a dye (hereinafter, sometimes referred to as dye (A1-1)) and / or a pigment (hereinafter, sometimes referred to as pigment (A1-2)) other than the compound (I) and the perylene compound (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.

[0108] The dye (A1-1) is not particularly limited, and known dyes can be used as long as it does not include the compound (I) and the perylene compound, 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.

[0109] The pigment (A1-2) is not particularly limited, and any known pigment can be used as long as it does not contain 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, 7; Examples include:

[0110] When the colorant (A) further contains a colorant (A1), the lower limit of the total content of the compound (I) 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 compound (I) and the perylene compound in the colorant (A) is, for example, less than 100 mass% based on the total amount of the colorant (A).

[0111] The colorant (A) may be subjected, as necessary, 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 (A) using a polymer compound, etc., a microparticulation treatment using a sulfuric acid microparticulation 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 (A) is preferably approximately uniform.

[0112] <Colored resin composition> The colored resin composition of the present invention contains a colorant (A) and a resin (hereinafter, may be referred to as resin (B)). The colored resin composition of the present invention may further contain a polymerizable compound (hereinafter, may be referred to as a polymerizable compound (C)) and a polymerization initiator (hereinafter, may be referred to as a polymerization initiator (D)). The colored resin composition of the present invention may further contain a solvent (hereinafter, may be referred to as solvent (E)). The colored 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 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.

[0113] When the colored resin composition contains a solvent (E), a colored composition (sometimes called a colorant-containing liquid) containing a colorant (A) and a solvent (E) may be prepared in advance, and then the colored resin composition may be prepared using the colored composition. When the colorant (A) is not soluble in the solvent (E), for example, when the colorant (A) contains a pigment (A1-2), the colored composition can be prepared by dispersing the colorant (A) in the solvent (E) and mixing them. The colored composition may contain a part or all of the solvent (E) contained in the colored resin composition.

[0114] The content of the colorant (A) in the coloring composition is preferably from 0.001% by mass to 99% by mass, more preferably from 0.01% by mass to 95% by mass, even more preferably from 0.1% by mass to 90% by mass, and still more preferably from 0.1% by mass to 50% by mass, based on the total amount of the coloring composition.

[0115] 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.

[0116] 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.

[0117] 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 3,000 parts by mass or less, and even more preferably 20 parts by mass or more and 1,000 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 colored composition in a more uniformly dispersed state tends to be obtained.

[0118] 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 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 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.

[0119] <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 / or 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.

[0120] 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-5-ethylbicyclo[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.

[0121] When the resin (B) is a copolymer having structural units derived from the monomer (a), the ratio of the structural units derived from the monomer (a) in the copolymer is preferably 2 to 60 mol % of all the structural units of the copolymer.

[0122] 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. The monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0123] 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)").

[0124] Examples of the monomer (b1) include a monomer having a structure in which a linear or branched unsaturated aliphatic hydrocarbon has been epoxidized (hereinafter, may be referred to as "monomer (b1-1)") and a monomer having a structure in which an unsaturated alicyclic hydrocarbon has been epoxidized (hereinafter, may be referred to as "monomer (b1-2)").

[0125] The monomer (b1-1) is preferably a monomer having a glycidyl group and an ethylenically unsaturated bond. 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(glycidyl ether), 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.

[0126] 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).

[0127] [ka] [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.]

[0128] 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.

[0129] 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.

[0130] 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.

[0131] 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.

[0132] X a and X b Preferred examples of the group include a single bond, a methylene group, an ethylene group, *-CH2-O-, and *-CH2CH2-O-, and more preferred examples include a single bond and *-CH2CH2-O- (* represents a bond to O).

[0133] 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.

[0134] [ka]

[0135] 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).

[0136] [ka]

[0137] The compound represented by formula (BI) and the compound represented by formula (BII) may be used alone or in combination of two or more. The compound represented by formula (BI) and the compound represented by formula (BII) may be used in combination. When the compound represented by formula (BI) and the compound represented by formula (BII) are used in combination, the content ratio of these [compound represented by formula (BI): compound represented by formula (BII)] is preferably 5:95 to 95:5, more preferably 10:90 to 90:10, and even more preferably 20:80 to 80:20 on a molar basis.

[0138] 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.

[0139] The monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond is more preferably a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group. Examples of the monomer (b3) include tetrahydrofurfuryl acrylate (eg, Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate, and the like.

[0140] When the resin (B) is a copolymer having structural units derived from the monomer (b), the ratio of the structural units derived from the monomer (b) in the copolymer is preferably 2 to 98 mol % of all the structural units of the copolymer.

[0141] 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; Halogen-containing (meth)acrylic acid esters such as 2,2,3,3,4,4,5,5-octafluoropentyl (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, 9-vinylcarbazole, 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.

[0142] When the resin (B) is a copolymer having structural units derived from the monomer (c), the ratio of the structural units derived from the monomer (c) in the copolymer is preferably 1 to 98 mol % of all the structural units of the copolymer.

[0143] 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[5.2.1.02,6 ]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). In a copolymer containing structural units derived from monomer (a) and structural units derived from monomer (b), it is preferable that the ratio of the structural units derived from each monomer is within the following range among all structural units constituting the copolymer. Structural units derived from monomer (a): 2 to 60 mol % (more preferably 10 to 50 mol %) Structural units derived from monomer (b): 40 to 98 mol % (more preferably 50 to 90 mol %) When the ratio of the structural units derived from the monomers (a) and (b) is within the above range, the colored resin composition tends to have excellent storage stability, developability when forming a colored pattern, and solvent resistance of the resulting color filter.

[0144] 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.

[0145] 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.

[0146] 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 or more and 5 or less, and further preferably 1 or more and 4 or less.

[0147] The acid value (solid content equivalent value) of the resin (B) is preferably 10 mg-KOH / g to 300 mg-KOH / g, more preferably 20 mg-KOH / g to 250 mg-KOH / g, even more preferably 25 mg-KOH / g to 200 mg-KOH / g, even more preferably 30 mg-KOH / g to 150 mg-KOH / g, and particularly preferably 40 mg-KOH / g to 135 mg-KOH / g. The acid value here 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.

[0148] The content of the resin (B) is preferably 5 to 80 mass%, more preferably 10 to 60 mass%, further preferably 15 to 50 mass%, and even more preferably 15 to 45 mass% in 100 mass% of the solid content of the colored resin composition. When the content of the resin (B) is within the above range, the solubility of the unexposed area in the developer tends to be high.

[0149] <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.

[0150] 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).

[0151] 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.

[0152] 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.

[0153] The weight average molecular weight of the polymerizable compound (C) is preferably 50 or more and 4000 or less, more preferably 70 or more and 3500 or less, even more preferably 100 or more and 3000 or less, still more preferably 150 or more and 2900 or less, and particularly preferably 250 or more and 1500 or less.

[0154] When the polymerizable compound (C) is contained, 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, in the total amount of the solid content of the colored resin composition.

[0155] <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.

[0156] Examples of the polymerization initiator (D) include an oxime compound (for example, an O-acyloxime compound), an alkylphenone compound, a biimidazole compound, a triazine compound, and an acylphosphine oxide compound.

[0157] 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.

[0158] 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.

[0159] 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).

[0160] 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.

[0161] 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.

[0162] 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) described below, particularly amines.

[0163] 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 oxime compound, and a biimidazole compound, more preferably a polymerization initiator containing an oxime compound, and even more preferably a polymerization initiator containing an O-acyloxime compound.

[0164] When the polymerization initiator (D) is contained, the content of the polymerization initiator (D) is preferably 0.01 parts by mass or more and 30 parts by mass or less, more preferably 0.1 parts 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 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.

[0165] <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). Examples of the polymerization initiator aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0166] 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.

[0167] 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.

[0168] Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0169] 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.

[0170] When these polymerization initiation aids (D1) are used, the content thereof is preferably 0.01 parts by mass or more and 30 parts by mass or less, more preferably 0.1 parts by mass or more and 20 parts by mass or less, relative to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C) contained in the colored resin composition.

[0171] <Solvent (E)> The solvent (E) is not particularly limited, and any solvent commonly used in the relevant field can be used. Examples of the solvent (E) include ester solvents (solvents containing -CO-O- but not -O- in the molecule), ether solvents (solvents containing -O- but not -CO-O- in the molecule), ether ester solvents (solvents containing -CO-O- and -O- in the molecule), ketone solvents (solvents containing -CO- but not -CO-O- in the molecule), alcohol solvents (solvents containing OH in the molecule and not containing -O-, -CO- and -CO-O-), hydrocarbon solvents, amide solvents, dimethyl sulfoxide and the like.

[0172] 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.

[0173] 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.

[0174] 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.

[0175] 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.

[0176] Examples of the alcohol solvent include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0177] Examples of the hydrocarbon solvent include benzene, toluene, xylene, cyclohexane, methylcyclohexane, ethylcyclohexane, normal hexane, styrene, and mesitylene.

[0178] Examples of the amide solvent include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0179] These solvents may be used in combination of two or more kinds.

[0180] As the solvent, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, diacetone alcohol, and cyclohexanone are preferred, propylene glycol monomethyl ether acetate and cyclohexanone are more preferred, and propylene glycol monomethyl ether acetate is even more preferred.

[0181] When the solvent (E) is contained, the content of the solvent (E) is usually less than 100% by mass, preferably 99.99% by mass or less, more preferably 1% by mass or more and 99.9% by mass or less, even more preferably 10% by mass or more and 99% by mass or less, even more preferably 20% by mass or more and 97% by mass or less, particularly preferably 30% by mass or more and 95% by mass or less, even more preferably 40% by mass or more and 95% by mass or less, and particularly preferably 50% by mass or more and 95% 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.

[0182] <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.

[0183] 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).

[0184] 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.).

[0185] 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).

[0186] When the leveling agent (F) is contained, the content of the leveling agent (F) is preferably 0.0005% by mass or more and 3% by mass or less, more preferably 0.001% by mass or more and 1% by mass or less, and even more preferably 0.005% by mass or more and 0.5% by mass or less, based on the total amount of the colored 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.

[0187] <Other ingredients> The colored resin composition may contain additives known in the art, such as fillers, other polymer compounds, adhesion promoters, quenchers, antioxidants, light stabilizers, and chain transfer agents, as necessary.

[0188] <Method of producing colored resin composition> The colored resin composition can be prepared by mixing the colorant (A) and the resin (B), as well as the polymerizable compound (C), polymerization initiator (D), polymerization initiator aid (D1), solvent (E), leveling agent (F) and / or other components that are used as needed. The mixing can be carried out 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 in a bead mill or the like until the average particle size becomes about 0.2 μm or less. In this case, the dispersant and a part or all of the resin (B) may be added as necessary. The colorant (A) may be used in a state in which it is dissolved in advance in a part or whole of the solvent (E). The remaining components are mixed with the colored composition (color-containing liquid) obtained as described above to give a predetermined concentration, whereby the desired colored resin composition can be prepared.

[0189] <Manufacturing method for color filters> A color filter, which may be a color conversion layer, can be formed from the colored resin composition. A colored coating film can be formed by applying the colored resin composition to a substrate, removing volatile components such as a solvent, and drying the resulting coating. The colored coating film thus formed is included in the color filter of the present invention. 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 resin composition is applied to a substrate, dried to form a colored composition layer, and the colored composition layer is exposed through a photomask and developed. In the photolithography, a colored coating film, which is a cured product of the colored 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.

[0190] The film thickness of the color filter to be produced is not particularly limited and can be adjusted appropriately depending on the purpose, use, etc., and is, for example, preferably 30 μm or less, more preferably 20 μm or less, even more preferably 6 μm or less, and even more preferably 3 μm or less, and although there is no particular lower limit, it is usually 0.1 μm or more.

[0191] 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.

[0192] 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, a colored resin composition is applied onto a substrate, and then dried by heating and drying (pre-baking) and / or drying under reduced pressure to remove volatile components such as a solvent, thereby obtaining a smooth colored 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 composition layer is not particularly limited, and may be appropriately selected depending on the intended thickness of the color filter.

[0193] Next, the colored 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. As the light source used for exposure, a light source that generates light with a wavelength of 250 nm or more and 450 nm or less is preferable. For example, light less than 350 nm may be cut using a filter that cuts this wavelength range, or light near 436 nm, near 408 nm, and near 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, halogen lamps, and the like. In addition, it is preferable to use an exposure device (mask aligner) such as a stepper (reduced projection exposure machine) or a proximity exposure machine, since it is possible to uniformly irradiate the entire exposed surface with parallel light rays and to accurately align the photomask with the substrate on which the colored composition layer is formed.

[0194] The colored 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 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.

[0195] Furthermore, it is preferable to perform post-baking on the obtained colored pattern. The post-baking temperature is preferably 100° C. or higher, more preferably 150° C. or higher, even more preferably 160° C. or higher, and preferably 250° C. or lower, more preferably 240° C. or lower. The post-baking time is preferably 1 minute or longer, more preferably 2 minutes or longer, even more preferably 10 minutes or longer, preferably 120 minutes or lower, and more preferably 60 minutes or lower. The color filter, which is a colored pattern or colored coating film thus obtained, may be further subjected to a surface coating treatment in order to impart various properties.

[0196] <Display device> The color filter is useful as a color filter used in display devices (e.g., liquid crystal display devices, organic EL display devices, electronic paper, etc.) and solid-state imaging devices, particularly as a color filter used in organic EL display devices using OLEDs (Organic Light Emitting Diodes), etc. Organic EL display devices do not require a backlight, and therefore can be made lighter and thinner than liquid crystal display devices, etc., can achieve high image quality such as a fast response speed and high contrast, are power-saving, and can be bent, and therefore are used in various fields such as mobile phones, portable information terminals, and televisions.

[0197] According to the colored resin composition containing the colorant (A) of the present invention, it is possible to form a color filter having excellent light resistance. In the present invention, good light resistance means that the color change before and after a light irradiation test is small, or the change in fluorescence intensity before and after a light irradiation test is small (i.e., the maintenance rate of fluorescence intensity is high). In addition, according to the colored resin composition containing the colorant (A) of the present invention, it is possible to form a color filter having high fluorescence intensity and excellent brightness compared to a colored resin composition containing a conventional perylene compound as a colorant. Furthermore, according to the colored resin composition containing the colorant (A) of the present invention, it is possible to form a color filter having excellent heat resistance. In the present invention, good heat resistance means that the color change before and after a heating test is small, or the change in fluorescence intensity before and after a heating test is small (i.e., the maintenance rate of fluorescence intensity is high). The fluorescence intensity can be measured using, for example, a fluorescence spectrophotometer (FluoroMAX-3; manufactured by Horiba, Ltd.). EXAMPLES

[0198] 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".

[0199] In the following examples, the structures of the compounds were confirmed by mass spectrometry (LC; Agilent 1200 model, MASS; Agilent LC / MSD6130 model).

[0200] 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.

[0201] (Synthesis Example 1) <Preparation of Compound (IV)> 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 tetrahydrofuran represented by formula (IV). 1 ,N 2 15 parts of -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 (IV)) were obtained (yield 75%).

[0202] [ka]

[0203] <Identification of compound (IV)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 805 Exact Mass: 804

[0204] Example 1 <Preparation of Compound (I-27), Compound (I-25), and Compound (I-36); Colorant 1> 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-acid anhydride 5.0 parts, 2-ethylhexanol (Tokyo Chemical Industry Co., Ltd.) 3.5 parts, 1-bromo-2-ethylhexane (Tokyo Chemical Industry Co., Ltd.) 4.3 parts, 1-octanol (Tokyo Chemical Industry Co., Ltd.) 3.5 parts, 1-bromooctane (Tokyo Chemical Industry Co., Ltd.) 4.3 parts, 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 dropped and stirred at 70 ° C. for 6 hours. The resulting mixture was concentrated, and 30 parts of methanol was added, resulting in the formation of a yellow precipitate. The mixture containing the 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), to obtain 4.3 parts of a mixture (colorant 1) of compounds represented by formula (I-27), formula (I-25) and formula (I-36) (hereinafter, the compound represented by formula (I-27) may be referred to as compound (I-27), the compound represented by formula (I-25) may be referred to as compound (I-25), and the compound represented by formula (I-36) may be referred to as compound (I-36)) (yield 66%). 1 From the H NMR spectrum, the ratio of compound (I-27), compound (I-25), and compound (I-36) was 53:23:24. In Colorant 1, compound (I-27) corresponds to compound (Ia) of the present invention, compound (I-25) corresponds to compound (Ib) of the present invention, and compound (I-36) corresponds to compound (Ic) of the present invention.

[0205] [ka]

[0206] <Identification of compound (I-27)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1047 Exact Mass: 1046 <Identification of compound (I-25)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1047 Exact Mass: 1046 <Identification of compound (I-36)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1047 Exact Mass: 1046

[0207] Example 2 <Preparation of Compound (I-14), Compound (I-36), and Compound (I-10); Colorant 2> Except for replacing 3.5 parts of 1-octanol with 2.7 parts of 1-hexanol (manufactured by Tokyo Chemical Industry Co., Ltd.) and 4.3 parts of 1-bromooctane with 3.7 parts of 1-bromohexane (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Example 1 was performed to obtain 5.1 parts of a mixture (colorant 2) of compounds represented by formulas (I-14), (I-36), and (I-10) (hereinafter, the compound represented by formula (I-14) may be referred to as compound (I-14), and the compound represented by formula (I-10) may be referred to as compound (I-10)) (yield 81%). 1 From the H NMR spectrum, the ratio of compound (I-14), compound (I-36), and compound (I-10) was 47:28:25. In Colorant 2, compound (I-14) corresponds to compound (Ia) of the present invention, compound (I-36) corresponds to compound (Ib) of the present invention, and compound (I-10) corresponds to compound (Ic) of the present invention.

[0208] [ka]

[0209] <Identification of compound (I-14)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1019 Exact Mass: 1018

[0210] <Identification of compound (I-36)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1047 Exact Mass: 1046

[0211] <Identification of compound (I-10)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 991 Exact Mass: 990

[0212] Example 3 <Preparation of Compound (I-3), Compound (I-18), and Compound (I-1); Colorant 3> Except for replacing 3.5 parts of 2-ethylhexanol with 3.1 parts of 1-heptanol (manufactured by Tokyo Chemical Industry Co., Ltd.), 4.3 parts of 1-bromo-2-ethylhexane with 3.9 parts of 1-bromoheptane (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.5 parts of 1-octanol with 2.4 parts of 1-pentanol (manufactured by Tokyo Chemical Industry Co., Ltd.), and 4.3 parts of 1-bromooctane with 3.4 parts of 1-bromopentane (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Example 1 was used to obtain 5.1 parts of a mixture (colorant 3) of compounds represented by formulas (I-3), (I-18) and (I-1) (hereinafter, the compound represented by formula (I-3) may be referred to as compound (I-3), the compound represented by formula (I-18) may be referred to as compound (I-18), and the compound represented by formula (I-1) may be referred to as compound (I-1)). (Yield 83%) 1 From the H NMR spectrum, the ratio of compound (I-3), compound (I-18), and compound (I-1) was 49:27:24. In colorant 3, compound (I-3) corresponds to compound (Ia) of the present invention, and compound (I-18) corresponds to compound (Ib) of the present invention. Compound (I-1) corresponds to compound (Ic) of the present invention.

[0213] [ka]

[0214] <Identification of compound (I-3)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 991 Exact Mass: 990

[0215] <Identification of compound (I-18)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1019 Exact Mass: 1018

[0216] <Identification of compound (I-1)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 963 Exact Mass: 962

[0217] Example 4 <Preparation of Compound (I-4), Compound (I-25), and Compound (I-1); Colorant 4> Except for replacing 3.5 parts of 2-ethylhexanol with 3.8 parts of 1-octanol (manufactured by Tokyo Chemical Industry Co., Ltd.), 4.3 parts of 1-bromo-2-ethylhexane with 4.3 parts of 1-bromooctane (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.5 parts of 1-octanol with 2.4 parts of 1-pentanol (manufactured by Tokyo Chemical Industry Co., Ltd.), and 4.3 parts of 1-bromooctane with 3.4 parts of 1-bromopentane (manufactured by Tokyo Chemical Industry Co., Ltd.), 5.1 parts of a mixture (colorant 4) of compounds represented by formula (I-4), formula (I-25) and formula (I-1) (hereinafter, the compound represented by formula (I-4) may be referred to as compound (I-4)) was obtained in the same manner as in Example 1 (yield 85%). 1From the H NMR spectrum, the ratio of compound (I-4), compound (I-25), and compound (I-1) was 50:25:25. In Colorant 4, compound (I-4) corresponds to compound (Ia) of the present invention, compound (I-25) corresponds to compound (Ib) of the present invention, and compound (I-1) corresponds to compound (Ic) of the present invention.

[0218] [ka]

[0219] <Identification of compound (I-4)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1005 Exact Mass: 1004

[0220] <Identification of compound (I-25)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1047 Exact Mass: 1046

[0221] <Identification of compound (I-1)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 963 Exact Mass: 962

[0222] Example 5 <Preparation of Compound (I-39), Compound (I-36) and Compound (I-45); Colorant 5> Except for changing 3.5 parts of 1-octanol to 2.9 parts of benzyl alcohol (manufactured by Aldrich Co., Ltd.) and changing 4.3 parts of 1-bromooctane to 3.8 parts of benzyl bromide (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Example 1 was carried out to obtain 4.2 parts of a mixture (colorant 5) of compounds represented by formulas (I-39), (I-36), and (I-45) (hereinafter, the compound represented by formula (I-39) may be referred to as compound (I-39), and the compound represented by formula (I-45) may be referred to as compound (I-45)) (yield 66%). 1From the H NMR spectrum, the ratio of compound (I-39), compound (I-36), and compound (I-45) was 47:28:25. In Colorant 5, compound (I-39) corresponds to compound (Ia) of the present invention, compound (I-36) corresponds to compound (Ib) of the present invention, and compound (I-45) corresponds to compound (Ic) of the present invention.

[0223] [ka]

[0224] <Identification of compound (I-39)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1025 Exact Mass: 1024

[0225] <Identification of compound (I-36)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1047 Exact Mass: 1046

[0226] <Identification of compound (I-45)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1003 Exact Mass: 1002

[0227] Example 6 <Preparation of Compound (I-16), Compound (I-43), and Compound (I-10); Colorant 6> Except for replacing 3.5 parts of 2-ethylhexanol with 3.0 parts of cyclohexanemethanol (manufactured by Tokyo Chemical Industry Co., Ltd.), 4.3 parts of 1-bromo-2-ethylhexane with 3.9 parts of (bromomethyl)cyclohexane (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.5 parts of 1-octanol with 2.7 parts of 1-hexanol (manufactured by Tokyo Chemical Industry Co., Ltd.), and 4.3 parts of 1-bromooctane with 3.7 parts of 1-bromohexane (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Example 1 was followed to obtain 4.6 parts of a mixture (colorant 6) of compounds represented by formulas (I-16), (I-43) and (I-10) (hereinafter, the compound represented by formula (I-16) may be referred to as compound (I-16), and the compound represented by formula (I-43) may be referred to as compound (I-43)). (Yield 74%) 1 From the H NMR spectrum, the ratio of compound (I-16), compound (I-43), and compound (I-10) was 50:24:26. ​​In Colorant 6, compound (I-16) corresponds to compound (Ia) of the present invention, compound (I-43) corresponds to compound (Ib) of the present invention, and compound (I-10) corresponds to compound (Ic) of the present invention.

[0228] [ka]

[0229] <Identification of compound (I-16)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1003 Exact Mass: 1002

[0230] <Identification of compound (I-43)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1015 Exact Mass: 1014

[0231] <Identification of compound (I-10)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 991 Exact Mass: 990

[0232] Example 7 <Preparation of Compound (I-43) and Compound (I-10); Colorant 7> N obtained in Synthesis Example 1 1 ,N 2 -bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexacarboxylic acid-2,3,8,9-bisimide-11,12-anhydride 5.0 parts, cyclohexylmethyl bromide (Tokyo Chemical Industry Co., Ltd.) 7.8 parts, cyclohexylmethanol (Tokyo Chemical Industry Co., Ltd.) 6.1 parts, N,N-dimethylformamide (Kanto Chemical Co., Ltd.) 70 parts were added, and the mixture was 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 the mixture was stirred at 60 ° C. for 6 hours. The obtained mixture was concentrated, and 30 parts of methanol were added, resulting in 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 4.1 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(cyclohexylmethyl ester) were obtained (yield 66%).

[0233] N obtained in Synthesis Example 1 1 ,N 2-bis(2,6-diisopropylphenyl)benzo[ghi]perylene-2,3,8,9,11,12-hexacarboxylic acid-2,3,8,9-bisimide-11,12-anhydride 5.0 parts, 1-bromohexane (Tokyo Chemical Industry Co., Ltd.) 7.3 parts, 1-hexanol (Tokyo Chemical Industry Co., Ltd.) 4.0 parts, N,N-dimethylformamide (Kanto Chemical Co., Ltd.) 70 parts were added, and the mixture was 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 the mixture was 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 using a silica gel column (solvent: chloroform), yielding N 1 ,N 2 4.3 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-hexyl ester) were obtained (yield 70%).

[0234] 10 parts of compound (I-43), 10 parts of compound (I-10), and 200 parts of dichloromethane (Kanto Chemical Co., Ltd.) were added and stirred at 23° C. for 1 hour. The resulting solution was concentrated to obtain 20 parts of a mixture of compound (I-43) and compound (I-10) (colorant 7). In colorant 7, compound (I-43) corresponds to compound (Ib) of the present invention, and compound (I-10) corresponds to compound (Ic) of the present invention.

[0235] [ka]

[0236] <Identification of compound (I-43)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1015 Exact Mass: 1014

[0237] <Identification of Compound (I-10)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 991 Exact Mass: 990

[0238] (Synthesis Example 2) <Preparation of Lumogen® F Yellow 083> Lumogen® F Yellow 083 represented by the following formula (x) was synthesized according to the description in JP-A-60-203650.

[0239]

Chemical formula

[0240] (Synthesis Example 3) <Preparation of Compound INT>

[0241]

Chemical formula

[0242] 10 parts of 1,6,7,12-tetrachloro-3,4,9,10-perylene dianhydride (manufactured by CombiChem Co., Ltd.), 13 parts of 2,6-diisopropyl aniline (manufactured by Tokyo Chemical Industry Co., Ltd.), and 188 parts of propionic acid were added, and the mixture was stirred for 20 hours under reflux. While maintaining the obtained mixture at 20°C or lower, 50 parts of water was added, and an orange precipitate was formed. 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 Compound INT) (yield 75%).

[0243] <Identification of Compound INT> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 847 Exact Mass: 846

[0244] (Synthesis Example 4) <Preparation of compound (II-16)> 5.0 parts of the produced compound 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%).

[0245] [ka]

[0246] <Identification of compound (II-16)> (Mass spectrometry) Ionization mode = ESI+: m / z = [M+H] + 1237 Exact Mass: 1236

[0247] (Synthesis Example 5) 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.

[0248] [ka]

[0249] (Synthesis Example 6) <Preparation of Resin B1> A suitable amount of nitrogen was poured into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the atmosphere with nitrogen, 280 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80°C with stirring. Next, 38 parts of acrylic acid, 3,4-epoxytricyclo[5.2.1.0 2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 A 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.

[0250] [ka]

[0251] <Example 8> (1) Solubility test of colorants in solvents (propylene glycol monomethyl ether acetate; hereinafter sometimes referred to as PGMEA) About 50 mg of solute (colorant 1; a mixture of compound (I-27), compound (I-25) and compound (I-36)) was weighed and placed in a 20 mL screw tube. About 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 3.

[0252] (2) Preparation of Coloring Composition The components were mixed in the following ratio to obtain colored composition 1. (A) Colorant: 2.6 parts of colorant 1 (B) Resin: 58 parts of resin B1 solution (E) Solvent: 420 parts of propylene glycol monomethyl ether acetate

[0253] (3) Preparation of Colored Resin Composition Next, the components were mixed in the following proportions to obtain a colored 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

[0254] (4) Preparation of colored coating film (color filter) A colored 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 1.9 to 2.1 μm, and then pre-baked at 100° C. for 3 minutes to form a colored composition layer. After cooling, the colored 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. The chromaticity of the colored coating film was evaluated by measuring the spectrum using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation) and measuring the xy chromaticity coordinates (x, y) and Y in the CIE XYZ color system using the characteristic function of the C light source.

[0255] (5) Fluorescence intensity measurement The fluorescence spectrum of the obtained colored coating film was measured using a fluorescence spectrophotometer (FluoroMAX-3; manufactured by Horiba, Ltd.) (excitation side slit 5 nm, fluorescence side slit 10 nm, excitation wavelength 460 nm), and the fluorescence intensity at the fluorescence wavelength was determined. Note that the fluorescence wavelength here is the wavelength when 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 in this test was evaluated with the fluorescence intensity of Comparative Example 1 set to 100. A fluorescence intensity of more than 100 means that the fluorescence intensity is higher than that of the colored coating film of Comparative Example 1. The results are shown in Table 3.

[0256] (6) Heat resistance test The obtained colored coating film was heated in an oven under an atmospheric atmosphere at 230°C for 180 minutes. The color difference ΔE was calculated from the xy chromaticity coordinates (x, y) and Y measured values ​​before and after the test according to the method described in JIS Z 8730:2009 (7. Calculation method of color difference). * ab was calculated. Color difference ΔE * The smaller the value of ab, the smaller the color change, and ΔE *If ab is 3 or less, the colored coating film can be said to have no practical problems as a color filter. In addition, before and after the heat resistance test, the fluorescence spectrum was measured using a fluorescence spectrophotometer (FluoroMAX-3; manufactured by Horiba, Ltd.) (excitation side slit 5 nm, fluorescence side slit 10 nm, excitation wavelength 460 nm) to determine the fluorescence intensity maintenance rate at the fluorescence wavelength. In this test, the fluorescence intensity maintenance rate is a value obtained by taking the fluorescence intensity of the colored coating film before the heat resistance test as 100%. The higher the fluorescence intensity maintenance rate, the better the heat resistance. In addition, if the heat resistance of the colored coating film is good, it can be said that the heat resistance of a colored pattern made from the same colored resin composition is also good. The results are shown in Table 3.

[0257] (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.). From the xy chromaticity coordinates (x, y) and Y measured values ​​before and after the test, the color difference ΔE was calculated according to the method described in JIS Z 8730:2009 (7. Calculation method of color difference). * ab was calculated. Color difference ΔE * The smaller the value of ab, the smaller the color change, and ΔE * If ab is 3 or less, the coating film can be said to have no practical problems as a color filter. In addition, before and after the light fastness test, the fluorescence spectrum was measured using a fluorescence spectrophotometer (FluoroMAX-3; manufactured by Horiba, Ltd.) (excitation side slit 5 nm, fluorescence side slit 10 nm, excitation wavelength 460 nm) to determine the fluorescence intensity maintenance rate at the fluorescence wavelength. In this test, the fluorescence intensity maintenance rate is a value obtained by taking the fluorescence intensity of the colored coating film before the light fastness test as 100%. The higher the fluorescence intensity maintenance rate, the better the light fastness. In addition, if the light fastness of the colored coating film is good, it can be said that the colored pattern made from the same colored resin composition also has good light fastness. The results are shown in Table 3.

[0258] <Examples 9 to 14 and Comparative Example 1> Instead of 2.6 parts of Colorant 1, 2.6 parts of Colorant 2 (Example 9), 2.6 parts of Colorant 3 (Example 10), 2.6 parts of Colorant 4 (Example 11), 2.6 parts of Colorant 5 (Example 12), 2.6 parts of Colorant 6 (Example 13), 2.6 parts of Colorant 7 (Example 14), or 2.6 parts of Lumogen® F Yellow 083 (Comparative Example 1) A colored resin composition was obtained and a colored coating film was produced in the same manner as in Example 8, except that the above was used as the colorant. Table 3 shows the solubility in PGMEA of the mixture of compounds used as the colorant in each Example or the compound used in Comparative Example 1, as well as the results of the measurement of the fluorescence intensity, the results of the heat resistance test, and the results of the light resistance test for each colored coating film.

[0259] [Table 3]

[0260] <Comparative Example 2> An attempt was made to prepare a colored resin composition and a colored coating film by using 2.6 parts of compound (I-43) as a colorant instead of 2.6 parts of colorant 1 in Example 8. However, compound (I-43) was poorly soluble in PGMEA, and its solubility in PGMEA could not be evaluated. Also, since compound (I-43) was poorly soluble in PGMEA, a colored coating film could not be obtained.

[0261] <Comparative Example 3> A colored resin composition was obtained and a colored coating film was produced in the same manner as in Example 8, except that 2.6 parts of compound (I-10) was used as the colorant instead of 2.6 parts of colorant 1. The solubility of compound (I-10) in PGMEA and the light resistance test results of the obtained colored coating film are shown in Table 4 together with the results of Example 14 and Comparative Example 2.

[0262] [Table 4]

[0263] From the results of Example 14 and Comparative Examples 2 and 3, it is clear that when a colorant containing one type of compound (I) is used, a colored coating film having excellent light resistance cannot be obtained. 1 It has been found that by using a colorant (A) containing at least two kinds of compounds (I) having mutually different groups, a colored coating film having excellent light resistance can be obtained.

[0264] <Example 15> The components were mixed in the following ratio to obtain colored composition 1-2. (A) Colorant: 1.3 parts of Colorant 1 Compound (II-16) 2.6 parts (B) Resin: 54 parts of resin B1 solution (E) Solvent: 420 parts of propylene glycol monomethyl ether acetate A colored resin composition was obtained and a colored coating film was produced in the same manner as in Example 8, except that the colored composition 1-2 was used instead of the colored composition 1. The results of the fluorescence intensity measurement, heat resistance test, and light resistance test for the obtained colored coating film are shown in Table 5.

[0265] <Examples 16 to 21 and Comparative Example 4> Instead of 1.3 parts of colorant 1, 1.3 parts of Colorant 2 (Example 16), 1.3 parts of Colorant 3 (Example 17), 1.3 parts of Colorant 4 (Example 18), 1.3 parts of Colorant 5 (Example 19), 1.3 parts of Colorant 6 (Example 20), 1.3 parts of Colorant 7 (Example 21), or 1.3 parts of Lumogen® F Yellow 083 (Comparative Example 4) A colored resin composition was obtained and a colored coating film was produced in the same manner as in Example 15, except that the above was used. The results of the fluorescence intensity measurement, the heat resistance test, and the light resistance test for each colored coating film are shown in Table 5.

[0266] <Example 22> The components were mixed in the following ratio to obtain colored composition 1-3. (A) Colorant: 1.3 parts of Colorant 1 Compound (II-3) 2.6 parts (B) Resin: 54 parts of resin B1 solution (E) Solvent: 420 parts of propylene glycol monomethyl ether acetate A colored resin composition was obtained and a colored coating film was produced in the same manner as in Example 8, except that the colored composition 1-3 was used instead of the colored composition 1. The results of the fluorescence intensity measurement, heat resistance test, and light resistance test for the obtained colored coating film are shown in Table 5.

[0267] <Examples 23 to 24 and Comparative Example 5> Instead of 1.3 parts of colorant 1, 1.3 parts of Colorant 6 (Example 23), 1.3 parts of Colorant 7 (Example 24), or 1.3 parts of Lumogen® F Yellow 083 (Comparative Example 5) A colored resin composition was obtained and a colored coating film was produced in the same manner as in Example 22, except that the above was used. The results of the fluorescence intensity measurement, the heat resistance test, and the light resistance test for each colored coating film are shown in Table 5.

[0268] [Table 5]

[0269] From the above results, it was found that the colored coating film formed from the colored resin composition containing the compound (Ia) or colorant (A) of the present invention has excellent light resistance. It was also found that the compound (Ia) and colorant (A) of the present invention have high solubility in the solvent (PGMEA) and good solubility. Furthermore, it was found that the colored coating film formed from the colored resin composition containing the compound (Ia) or colorant (A) of the present invention has high fluorescence intensity and excellent heat resistance.

Claims

1. Contains at least two compounds represented by formula (I), Each of the two compounds represented by formula (I) comprises at least one of R 1 Colorants which are compounds different from each other. 【Chemistry 1】 [In formula (I), R 1 and R 2 each independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and —CH 2 - may be replaced by -O-, -CO-, -OCO- or -COO-. R 3 and R 8 each independently represents 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 combination thereof, and -CH 2 - may be replaced by -O-, -CO-, -OCO- or -COO-. R 4 , R 5 , R 6 , R 7 , R 9 and R 10 are each independently a hydrogen atom, -R 11 , a halogen atom, a hydroxy group, a carboxy group or a nitro group. R 4 and R 5 , R 5 and R 6 and R 6 and R 7 are bonded to each other to form -R 12 -CO-O-CO-R 13 -or-R 12 -CO-N(R 11 )-CO-R 13 A group represented by - may be formed. R 11 represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and the —CH 2 - may be replaced by -O-, -CO-, -OCO- or -COO-. 11 When there are multiple, they may be the same or different. R 12 and R 13 each independently represents a single bond or a divalent hydrocarbon group having 1 to 15 carbon atoms which may have a substituent, and -CH 2 - may be replaced by -O-, -CO-, -OCO- or -COO-. 12 When there are a plurality of R 13 When there are multiple, they may be the same or different.

2. As the compound represented by formula (I), at least two compounds selected from the group consisting of a compound represented by formula (Ia), a compound represented by formula (Ib), and a compound represented by formula (Ic) are (i) a combination of a compound represented by formula (Ia) and a compound represented by formula (Ib); (ii) a combination of a compound represented by formula (Ia) and a compound represented by formula (Ic), or (iii) The colorant according to claim 1, characterized in that it contains a combination of a compound represented by formula (Ib) and a compound represented by formula (Ic). 【Chemistry 2】 [In formula (Ia), formula (Ib) and formula (Ic), R 1a , R 2a , R 1b and R 1c each independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and —CH 2 - may be replaced by -O-, -CO-, -OCO- or -COO-. 1a and R 2a and are never the same, and R 1b and R 1c will never be the same. R 3 ~R 10 represents the same meaning as above.

3. At least one of the following conditions is satisfied: (i) a combination of a compound represented by formula (Ia) and a compound represented by formula (Ib); and (ii) a combination of a compound represented by formula (Ia) and a compound represented by formula (Ic), (i) In the case where a combination of a compound represented by formula (Ia) and a compound represented by formula (Ib) is satisfied, R 1a and R of formula (Ib) 1b is the same as (ii) In the case where a combination of a compound represented by formula (Ia) and a compound represented by formula (Ic) is satisfied, R 2a and R of formula (Ic) 1c 3. The colorant according to claim 2, wherein

4. The composition includes at least one compound represented by formula (Ia), at least one compound represented by formula (Ib), and at least one compound represented by formula (Ic), In the total amount of the compound represented by formula (Ia), the compound represented by formula (Ib) and the compound represented by formula (Ic), The content of the compound represented by formula (Ia) is 35 mol % or more and 65 mol % or less, The content of the compound represented by formula (Ib) is 15 mol % or more and 35 mol % or less, 4. The colorant according to claim 2, wherein the content of the compound represented by formula (Ic) is from 15 mol % to 35 mol %.

5. The colorant according to any one of claims 1 to 4, further comprising a perylene compound.

6. A colored resin composition comprising the colorant according to any one of claims 1 to 5 and a resin.

7. The colored resin composition according to claim 6, further comprising a polymerizable compound and a polymerization initiator.

8. The colored resin composition according to claim 6 or 7, further comprising a solvent.

9. A color filter formed from the colored resin composition according to any one of claims 6 to 8.

10. A display device comprising the color filter according to claim 9.

11. A compound represented by formula (Ia). 【Chemistry 3】 [In formula (Ia), R 1a and R 2a each independently represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and —CH 2 - may be replaced by -O-, -CO-, -OCO- or -COO-. 1a and R 2a will never be the same. R 3 and R 8 each independently represents 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 combination thereof, and -CH 2 - and -CH contained in the combined group 2 - may be replaced by -O-, -CO-, -OCO- or -COO-. R 4 , R 5 , R 6 , R 7 , R 9 and R 10 are each independently a hydrogen atom, -R 11 , a halogen atom, a hydroxy group, a carboxy group or a nitro group. R 4 and R 5 , R 5 and R 6 and R 6 and R 7 are bonded to each other to form -R 12 -CO-O-CO-R 13 -or-R 12 -CO-N(R 11 )-CO-R 13 A group represented by - may be formed. R 11 represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and the —CH 2 - may be replaced by -O-, -CO-, -OCO- or -COO-. 11 When there are multiple, they may be the same or different. R 12 and R 13 each independently represents a single bond or a divalent hydrocarbon group having 1 to 15 carbon atoms which may have a substituent, and -CH 2 - may be replaced by -O-, -CO-, -OCO- or -COO-. 12 When there are a plurality of R 13 When there are multiple, they may be the same or different.

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