Colored resin composition, compound, color filter, and display device

Abstract

To provide a compound capable of forming a color filter exhibiting good contrast, and a colored resin composition.SOLUTION: The colored resin composition contains a colorant and a resin, where the colorant comprises a compound represented by formula (I).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to compounds useful as dyes, colored resin compositions, color filters, and display devices. [Background technology]

[0002] Color filters used in display devices such as liquid crystal displays, electroluminescent displays, and plasma displays, as well as in solid-state image sensors such as CCDs and CMOS sensors, are manufactured from colored resin compositions. Perylenetetracarboxylic acid diimide compounds are known as colorants contained in such colored resin compositions (Patent Document 1). [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] Japanese Patent Publication No. 2020-079397 [Overview of the project] [Problems that the invention aims to solve]

[0004] However, color filters formed from colored resin compositions using the above-mentioned perylenetetracarboxylic acid diimide compounds as colorants, which have been known conventionally, have not provided sufficiently satisfactory contrast. Therefore, the object of the present invention is to provide a compound and a colored resin composition that can form a color filter exhibiting good contrast. [Means for solving the problem]

[0005] The gist of this invention is as follows: [1] A colored resin composition containing a coloring agent and a resin, wherein the coloring agent comprises a compound represented by formula (I). [ka] [In formula (I), R 1 and R 2 are, independently of each other, a hydrogen atom, -R 8a , or -SO2-R 8b . R 1 and R 2 may, together with the nitrogen atom to which each is attached, form a ring which may have a substituent, and -CH2- constituting the ring may be replaced by -O-, -CO-, -S-, -S(O)2-, -NH-, or -NR 8g -. R 3 ~R 7 are, independently of each other, a hydrogen atom, -R 8c , -O-R 8d , -CO-O-R 8e , -O-CO-R 8f , a halogen atom, a hydroxy group, a carboxy group, a sulfo group, or a nitro group. R 8a , R 8b , R 8c , R 8d , R 8e , R 8f , and R 8g are, independently of each other, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. R 8a , R 8b , R 8c , R 8d , R 8e , R 8f , and R 8g when there are a plurality of them, they may be the same or different. [2] The colored resin composition according to [1], wherein R 1 in formula (I) is -SO2-R 8b , and R 2 is a hydrogen atom or -R 8a . [3] The colored resin composition according to [1] or [2], further containing a polymerizable compound and a polymerization initiator. [4] A color filter formed from the colored resin composition according to any one of [1] to [3]. A display device including the color filter described in [5] [4]. [6] A compound represented by formula (IA). [ka] [In formula (IA), R 11 This represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. R 2 is a hydrogen atom, -R 8a , or -SO2-R 8b It represents. R 3 ~R 7 These are, independently of each other, hydrogen atoms, -R 8c , -OR 8d , -CO-OR 8e ,-O-CO-R 8f This represents a halogen atom, a hydroxyl group, a carboxyl group, a sulfo group, or a nitro group. R 8a , R 8b , R 8c , R 8d , R 8e , and R 8f Each of these independently represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. R 8c , R 8d , R 8e , and R 8f If multiple instances exist, they may be identical or different. [Effects of the Invention]

[0006] According to the present invention, it is possible to provide a compound capable of forming a color filter that exhibits good contrast, and a colored resin composition. [Modes for carrying out the invention]

[0007] The colored resin composition of the present invention comprises a coloring agent (hereinafter sometimes referred to as coloring agent (A)) and a resin (hereinafter sometimes referred to as resin (B)). The colored resin composition of the present invention may further contain a polymerizable compound (hereinafter sometimes referred to as polymerizable compound (C)) and a polymerization initiator (hereinafter sometimes referred to as polymerization initiator (D)). The colored resin composition of the present invention may further contain a solvent (hereinafter sometimes referred to as solvent (E)). The colored resin composition of the present invention may further contain a polymerization initiator (hereinafter sometimes referred to as polymerization initiator (D1)). The colored resin composition of the present invention may further contain a leveling agent (hereinafter sometimes referred to as leveling agent (F)). In this specification, the compounds exemplified as components may be used individually or in combination, unless otherwise specified.

[0008] <Coloring agent (A)> The coloring agent (A) contains a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)).

[0009] <<Compound (I)>> [ka] [In formula (I), R 1 and R 2 These are, independently of each other, hydrogen atoms, -R 8a , or -SO2-R 8b It represents. R 1 and R 2 Each of these may form a ring with the nitrogen atom to which it is bonded, and the -CH2- constituting the ring may be -O-, -CO-, -S-, -S(O)2-, -NH-, or -NR 8g - may be replaced with this. R 3 ~R 7 These are, independently of each other, hydrogen atoms, -R 8c , -OR 8d , -CO-OR 8e ,-O-CO-R 8frepresents a halogen atom, a hydroxy group, a carboxy group, a sulfo group, or a nitro group. R 8a R 8b R 8c R 8d R 8e R 8f and R 8g each independently represent a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent. R 8a R 8b R 8c R 8d R 8e R 8f and R 8g When there are a plurality of them, they may be the same or different.

[0010] R 8a R 8b R 8c R 8d R 8e R 8f and R 8g Examples of the hydrocarbon group having 1 to 20 carbon atoms represented by R include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or alicyclic.

[0011] R 8a R 8b R 8c R 8d R 8e R 8f and R 8gThe saturated or unsaturated linear hydrocarbon groups represented by include linear alkyl groups of methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, and eicosyl groups; isopropyl, (1-ethyl)propyl, isobutyl, sec-butyl, tert-butyl, (3-methyl)butyl, (1-methyl)butyl, and (1-ethyl)butyl groups. (2-methyl)butyl group, (2-ethyl)butyl group, (1-propyl)butyl group, isopentyl group, neopentyl group, tert-pentyl group, (2-methyl)pentyl group, (3-methyl)pentyl group, (1-ethyl)pentyl group, (2-ethyl)pentyl group, (3-ethyl)pentyl group, (1-propyl)pentyl group, (1-butyl)pentyl group, (2-propyl)pentyl group, isohexyl group, (2-methyl)hexyl group, (5-methyl)hexyl group, (1-ethyl)hexyl group, (2-ethyl)hexyl group, (1-propyl)hexyl group, (2-propyl)hexyl group, (1-butyl)hexyl group, (2-butyl)hexyl group, (1-pentyl)hexyl group, (2-methyl)heptyl group, (2-ethyl)heptyl group, (3-ethyl)heptyl group, (2-propyl)heptyl group, (1-butyl)heptyl group, (2-butyl)heptyl group, (1-pentyl)heptyl group, (2-pentyl)heptyl group, (1-hexyl)heptyl group, (2-methyl)octyl group, (2-ethyl)octyl group, (2-propyl)octyl group, (2-butyl)octyl group, (1-pentyl)octyl group, (2 Branched alkyl groups such as (pentyl)octyl group, (1-hexyl)octyl group, (2-hexyl)octyl group, (1-heptyl)octyl group, (2-ethyl)nonyl group, (2-propyl)nonyl group, (2-butyl)nonyl group, (2-pentyl)nonyl group, (1-hexyl)nonyl group, (2-hexyl)nonyl group, (1-heptyl)nonyl group, (1-octyl)nonyl group, (2-propyl)decyl group, (2-butyl)decyl group, (2-pentyl)decyl group, (2-hexyl)decyl group, (1-heptyl)decyl group, and (2-butyl)undecyl group;Alkenyl groups such as 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, etc.; and the like can be mentioned. The number of carbon atoms of the saturated chain hydrocarbon group is preferably 1 to 18, more preferably 1 to 16, and even more preferably 1 to 15. Also, the number of carbon atoms of the unsaturated chain hydrocarbon group is preferably 2 to 18, more preferably 2 to 16, and even more preferably 2 to 15.;

[0012] R 8a 、R 8b 、R 8c 、R 8d 、R 8e 、R 8f 、及びR 8g Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by R 8a , R 8b , R 8c , R 8d , R 8e , R 8f , and R 8g include cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, etc.; cycloalkenyl groups such as cyclohexenyl group (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl group, cyclooctenyl group, etc.; norbornyl group, adamantyl group, bicyclo[2.2.2]octyl group, etc. The number of carbon atoms of the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 18, more preferably 3 to 16, and even more preferably 3 to 15.

[0013] [[ID=二十一]]二十一 [[ID=二十二]]二十二R 8a 、R 8b 、R 8c 、R 8d 、R 8e 、R 8f 、及びR<000 / / 8g Examples of the aromatic hydrocarbon group represented by R 8a , R 8b , R 8c , R 8d , R 8e , R 8f , and R 8g include phenyl group, 1-naphthyl group, 2-naphthyl group, phenanthryl group, anthryl group, pyrenyl group, etc. The number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 20, more preferably 6 to 18, and even more preferably 6 to 15.

[0014] R 8a 、R 8b 、R 8c 、R 8d, R 8e , R 8f , and R 8g The hydrocarbon group represented by may be a group formed by combining two or more of the chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups listed above, as long as the upper limit of the number of carbon atoms is 20 or less. Such a group may be, for example, a combination of an aromatic hydrocarbon group and at least one group selected from a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group, and in the hydrocarbon group formed by this combination, the chain hydrocarbon group may be combined as a divalent group (for example, an alkanediyl group). Examples of hydrocarbon groups formed by combinations include aralkyl groups such as benzyl group, phenethyl group, 1-methyl-1-phenylethyl group, 1-naphthylmethyl group, 2-naphthylmethyl group, diphenylmethyl group, 2,2-diphenylethyl group, 3,3-diphenylpropyl group, and 4,4-diphenylbutyl group; arylalkenyl groups such as phenylethenyl group (phenylvinyl group); arylalkynyl groups such as phenylethynyl group; o-tolyl group, m-tolyl group, p-tolyl group, 2-ethylphenyl group, 3-ethylphenyl group, 4-ethylphenyl group, 2,3-dimethylphenyl group, 2,4-dimethylphenyl group, 2,5-dimethylphenyl group, 2,6-dimethylphenyl group, 3,4-dimethylphenyl group, 3,5-dimethylphenyl group, 2,4,6-trimethylphenyl group, 4-vinylphenyl group, o-isopropylphenyl group, and m-isopropylphenyl group. Alkylaryl groups such as pyruphenyl group, p-isopropylphenyl group, 2,3-diisopropylphenyl group, 2,4-diisopropylphenyl group, 2,5-diisopropylphenyl group, 2,6-diisopropylphenyl group, 3,5-diisopropylphenyl group, 2,4,6-triisopropylphenyl group, 4-butylphenyl group, o-tert-butylphenyl group, m-tert-butylphenyl group, p-tert-butylphenyl group, 2,6-di(tert-butyl)phenyl group, 3,5-di(tert-butyl)phenyl group, 3,6-di(tert-butyl)phenyl group, 4-tert-butyl-2,6-dimethylphenyl group, 4-pentylphenyl group, 4-octylphenyl group, 4-(2,4,4-trimethyl-2-pentyl)phenyl group, 2-dodecylphenyl group, 3-dodecylphenyl group, and 4-dodecylphenyl group;o-tolylmethyl group, m-tolylmethyl group, p-tolylmethyl group, 2-ethylphenylmethyl group, 3-ethylphenylmethyl group, 4-ethylphenylmethyl group, 2,3-dimethylphenylmethyl group, 2,4-dimethylphenylmethyl group, 2,5-dimethylphenylmethyl group, 2,6-dimethylphenylmethyl group, 3,4-dimethylphenylmethyl group, 3,5-dimethylphenylmethyl group, 2,4,6-trimethylphenylmethyl group, 4-vinylphenylmethyl group, o-isopropylphenylmethyl group, m-isopropylphenylmethyl group, p-isopropylphenylmethyl group, 2,3-diisopropylphenylmethyl group, 2,4-diisopropylphenylmethyl group, 2,5-diisopropylphenylmethyl group, 2,6-diisopropylphenylmethyl group, 3,5-di Examples include alkylaryl alkyl groups such as isopropylphenylmethyl group; aryl groups to which alkanediyl groups are attached, such as 2,3-dihydro-4-indenyl group, 1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 8-methyl-1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 5,6,7,8-tetrahydro-1-naphthyl group, 5,6,7,8-tetrahydro-2-naphthyl group, 3-methyl-5,6,7,8-tetrahydro-2-naphthyl group, and 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl group; aryl groups to which one or more aryl groups are attached, such as biphenylyl group and terphenylyl group; and cyclohexylmethylphenyl group, benzylphenyl group, (dimethyl(phenyl)methyl)phenyl group, etc. Furthermore, the above hydrocarbon group may be a hydrocarbon group formed by a combination of a chain hydrocarbon group and an alicyclic hydrocarbon group, for example, 1-methylcyclopropyl group, 2-methylcyclopentyl group, 3-methylcyclopentyl group, 1-methylcyclohexyl group, 2-methylcyclohexyl group, 3-methylcyclohexyl group, 4-methylcyclohexyl group, 1,2-dimethylcyclohexyl group, 1,3-dimethylcyclohexyl group, 1,4-dimethylcyclohexyl group Chlohexyl group, 2,3-dimethylcyclohexyl group, 2,4-dimethylcyclohexyl group, 2,5-dimethylcyclohexyl group, 2,6-dimethylcyclohexyl group, 3,4-dimethylcyclohexyl group, 3,5-dimethylcyclohexyl group, 2,2-dimethylcyclohexyl group, 3,3-dimethylcyclohexyl group, 4,4-dimethylcyclohexyl group, 2,4,6-trimethylcyclohexyl group, 2,2,6,6-tetramethylcyclohexyl group Examples include alicyclic hydrocarbon groups to which one or more alkyl groups are attached, such as a 3,3,5,5-tetramethylcyclohexyl group, 4-pentylcyclohexyl group, 4-octylcyclohexyl group, and 4-cyclohexylcyclohexyl group; alkyl groups to which one or more alicyclic hydrocarbon groups are attached, such as cyclopropylmethyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, cyclohexylethyl group, and adamantylmethyl group; and alkyl groups to which one or more alkyl groups are attached, such as 2-methylcyclopropylmethyl group, 2-methylcyclobutylmethyl group, 3-methylcyclobutylmethyl group, 2-methylcyclopentylmethyl group, 3-methylcyclopentylmethyl group, 2-methylcyclohexylmethyl group, 3-methylcyclohexylmethyl group, and 4-methylcyclohexylmethyl group. The number of carbon atoms in a group formed by combining two or more chain-like hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups is preferably 4 to 20, more preferably 5 to 18, and even more preferably 6 to 16.

[0015] -SO2-R 8bExamples include methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, butylsulfonyl group, pentylsulfonyl group, hexylsulfonyl group, heptylsulfonyl group, octylsulfonyl group, nonylsulfonyl group, decylsulfonyl group, isopropylsulfonyl group, (1-ethyl)propylsulfonyl group, sec-butylsulfonyl group, isobutylsulfonyl group, tert-butylsulfonyl group, (3-methyl)butylsulfonyl group, (1-methyl)butylsulfonyl group, (1-ethyl)butylsulfonyl group, (2-methyl)butylsulfonyl group Isopentyl group, (2-ethyl)butylsulfonyl group, (1-propyl)butylsulfonyl group, isopentylsulfonyl group, neopentylsulfonyl group, tert-pentylsulfonyl group, (2-methyl)pentylsulfonyl group, (3-methyl)pentylsulfonyl group, (1-ethyl)pentylsulfonyl group, (2-ethyl)pentylsulfonyl group, (3-ethyl)pentylsulfonyl group, (1-propyl)pentylsulfonyl group, (1-butyl)pentylsulfonyl group, (2-propyl)pentylsulfonyl group, (2-ethyl)hexylsulfonyl group, Chlopropylsulfonyl group, cyclobutylsulfonyl group, cyclopentylsulfonyl group, cyclohexylsulfonyl group, cycloheptylsulfonyl group, cyclooctylsulfonyl group, 2-methylcyclopentylsulfonyl group, 3-methylcyclopentylsulfonyl group, 2-methylcyclohexylsulfonyl group, 3-methylcyclohexylsulfonyl group, 4-methylcyclohexylsulfonyl group, cyclopentylmethylsulfonyl group, cyclopentylethylsulfonyl group, cyclohexylmethylsulfonyl group, cyclohexylethylsulfonyl group, 2-methylsulfonyl group Tylcyclopentylmethylsulfonyl group, 3-methylcyclopentylmethylsulfonyl group, 2-methylcyclohexylmethylsulfonyl group, 3-methylcyclohexylmethylsulfonyl group, 4-methylcyclohexylmethylsulfonyl group, phenylsulfonyl group, benzylsulfonyl group, phenethylsulfonyl group, 1-naphthylmethylsulfonyl group, 2-naphthylmethylsulfonyl group, o-tolylsulfonyl group, m-tolylsulfonyl group, p-tolylsulfonyl group, 2,3-dimethylphenylsulfonyl group, 2,4-dimethylphenylsulfonyl group, 2,Examples include 5-dimethylphenylsulfonyl group, 2,6-dimethylphenylsulfonyl group, 3,4-dimethylphenylsulfonyl group, 3,5-dimethylphenylsulfonyl group, o-tolylmethylsulfonyl group, m-tolylmethylsulfonyl group, p-tolylmethylsulfonyl group, 2,3-dimethylphenylmethylsulfonyl group, 2,4-dimethylphenylmethylsulfonyl group, 2,5-dimethylphenylmethylsulfonyl group, 2,6-dimethylphenylmethylsulfonyl group, 3,4-dimethylphenylmethylsulfonyl group, and 3,5-dimethylphenylmethylsulfonyl group.

[0016] -OR 8d Examples of these groups include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, isobutoxy group, sec-butoxy group, tert-butoxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, (2-ethyl)hexyloxy group, eicosyloxy group, 1-phenylethoxy group, 1-methyl-1-phenylethoxy group, phenyloxy group, 2,3-dimethylphenyloxy group, 2,4-dimethylphenyloxy group, 2,5-dimethylphenyloxy group, 2,6-dimethylphenyloxy group, 3,4-dimethylphenyloxy group, and 3,5-dimethylphenyloxy group.

[0017] -CO-OR 8e Examples include methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, tert-butoxycarbonyl group, butoxycarbonyl group, pentyloxycarbonyl group, hexyloxycarbonyl group, (2-ethyl)hexyloxycarbonyl group, heptyloxycarbonyl group, octyloxycarbonyl group, nonyloxycarbonyl group, decyloxycarbonyl group, phenyloxycarbonyl group, eicosyloxycarbonyl group, and the like.

[0018] -O-CO-R 8fExamples of such groups include acetoxy group, propanoyloxy group, butanoyloxy group, 2,2-dimethylpropanoyloxy group, pentanoyloxy group, hexanoyloxy group, (2-ethyl)hexanoyloxy group, heptanyloxy group, octanoyloxy group, nonanoyloxy group, decanoyloxy group, and benzoyloxy group.

[0019] R 8a , R 8b , R 8c , R 8d , R 8e , R 8f , and R 8g The substituents that a C1-C20 hydrocarbon group represented by may have include, for example, halogen atoms; groups combining a monovalent hydrocarbon group with at least one selected from the group consisting of -O-, -CO-, and divalent hydrocarbon groups (provided that at least one is -O- or -CO-); nitrile groups; nitro groups; amino groups; amide groups; sulfonamide groups; hydroxyl groups; thiol groups; C1-C15 alkylthio groups such as methylthio and ethylthio groups; allylthio groups; C6-C20 arylthio groups such as phenylthio, 1-naphthylthio, and 2-naphthylthio groups; sulfoxy groups; C1-C15 alkylsulfoxy groups such as methylsulfoxy and ethylsulfoxy groups; and phenylsulfoxy groups. Examples include aryl sulfoxy groups with 6 to 20 carbon atoms, such as xy group, 1-naphthylsulfoxy group, and 2-naphthylsulfoxy group; silyl group; boryl group; alkylamino groups with 1 to 15 carbon atoms, such as monomethylamino group, dimethylamino group, monoethylamino group, and diethylamino group; arylamino groups with 6 to 20 carbon atoms, such as monophenylamino group and diphenylamino group; aralkylamino groups with 7 to 20 carbon atoms, such as benzylamino group; alkylaminosulfonyl groups with 1 to 15 carbon atoms, such as N-methylaminosulfonyl group, N,N-dimethylaminosulfonyl group, and N-ethylaminosulfonyl group; carboxyl group; carbamoyl group; and heterocyclic groups with 1 to 20 carbon atoms, such as furyl group, pyrrolyl group, and thienyl group.

[0020] Examples of halogen atoms include fluorine, chlorine, bromine, and iodine atoms.

[0021] Examples of groups that combine a monovalent hydrocarbon group with at least one selected from the group consisting of -O-, -CO-, and divalent hydrocarbon groups (provided that at least one is -O- or -CO-) include the groups represented by the following formulas (Sa) and (Sb).

[0022] [ka] [In formula (Sa) and formula (Sb), R S This represents a hydrocarbon group having 1 to 20 carbon atoms, and the methylene group contained in the hydrocarbon group may be replaced by -O- and / or -CO-. * represents a bond.

[0023] R S As a hydrocarbon group having 1 to 20 carbon atoms, the above R 8a , R 8b , R 8c , R 8d , R 8e , R 8f , and R 8g The same example as the hydrocarbon group represented by can be given. R S When a methylene group in a hydrocarbon group represented by is replaced by -O- and / or -CO-, the number of such replacements may be one or two or more. Furthermore, when a methylene group in a hydrocarbon group is replaced by -O- and / or -CO-, the number of carbon atoms before replacement shall be considered the number of carbon atoms in the hydrocarbon group.

[0024] Examples of groups represented by formula (Sa) include alkoxy groups with 1 to 15 carbon atoms, such as methoxy and ethoxy groups; and aryloxy groups with 6 to 20 carbon atoms, such as phenyloxy, 1-naphthyloxy, and 2-naphthyloxy groups. Examples of groups represented by formula (Sb) include alkylcarbonyl groups with 2 to 15 carbon atoms, such as acetyl and propionyl groups; arylcarbonyl groups with 7 to 20 carbon atoms, such as benzoyl, 1-naphthylcarbonyl, and 2-naphthylcarbonyl groups; alkoxycarbonyl groups with 2 to 15 carbon atoms, such as methoxycarbonyl and ethoxycarbonyl groups; and aryloxycarbonyl groups with 7 to 19 carbon atoms, such as phenyloxycarbonyl, 1-naphthyloxycarbonyl, and 2-naphthyloxycarbonyl groups.

[0025] R 8a and R 8c The substituents that the hydrocarbon group having 1 to 20 carbon atoms represented by (Sa) may have are preferably groups that combine a monovalent hydrocarbon group with at least one selected from the group consisting of -O-, -CO-, and divalent hydrocarbon groups (provided that at least one is -O- or -CO-), and carboxyl groups, more preferably groups represented by (Sa) and formula (Sb), and more preferably carboxyl groups, as well as alkoxy groups having 1 to 15 carbon atoms, aryloxy groups having 6 to 20 carbon atoms, carboxyl groups, alkylcarbonyl groups having 2 to 15 carbon atoms, arylcarbonyl groups having 7 to 20 carbon atoms, and carbon Alkoxycarbonyl groups with 2 to 15 prime numbers and aryloxycarbonyl groups with 7 to 19 carbon atoms are more preferred, carboxyl groups, alkylcarbonyl groups with 2 to 15 carbon atoms, arylcarbonyl groups with 7 to 20 carbon atoms, alkoxycarbonyl groups with 2 to 15 carbon atoms, and aryloxycarbonyl groups with 7 to 19 carbon atoms are even more preferred, carboxyl groups and alkoxycarbonyl groups with 2 to 15 carbon atoms are even more preferred, alkoxycarbonyl groups with 2 to 10 carbon atoms are even more preferred, and alkoxycarbonyl groups with 2 to 5 carbon atoms are particularly preferred.

[0026] R 8b The substituents that the hydrocarbon group having 1 to 20 carbon atoms represented by may have are preferably halogen atoms, and more preferably fluorine atoms.8b When the substituents of a hydrocarbon group having 1 to 20 carbon atoms represented by are halogen atoms, it is preferable that all of the hydrogen atoms of the carbon atom to which the halogen atom is bonded are replaced by halogen atoms.

[0027] R 8a , R 8b , R 8c , R 8d , R 8e , R 8f , and R 8g When the hydrocarbon group represented by has substituents, the number of substituents may be one or two or more, and the two or more substituents may be independent of each other, identical or different. 8a , R 8b , R 8c , R 8d , R 8e , R 8f , and R 8g When the hydrocarbon group represented by has two or more halogen atoms as substituents, it is preferable that the two or more substituents are identical. 8a , R 8b , R 8c , R 8d , R 8e , R 8f , and R 8g When the hydrocarbon group represented by has substituents, it is preferable that the number of substituents be one.

[0028] R 1 For example, -R 8a , -SO2-R 8b Preferably, -SO2-R 8b This is preferable.

[0029] R 1 In R 8aPreferably, the group is a saturated linear hydrocarbon group which may have substituents, a saturated alicyclic hydrocarbon group which may have substituents, an aromatic hydrocarbon group which may have substituents, a group which is a combination of an aromatic hydrocarbon group which may have substituents and a linear hydrocarbon group, or a group which is a combination of an aromatic hydrocarbon group which may have substituents and an alicyclic hydrocarbon group; more preferably, the group is a saturated linear hydrocarbon group which may have substituents, a saturated alicyclic hydrocarbon group which may have substituents, a group which is a combination of an aromatic hydrocarbon group which may have substituents and a linear hydrocarbon group, or a group which is a combination of an aromatic hydrocarbon group which may have substituents and an alicyclic hydrocarbon group; even more preferably, the group is a saturated linear hydrocarbon group which may have substituents, a saturated alicyclic hydrocarbon group which may have substituents, or a group which is a combination of an aromatic hydrocarbon group which may have substituents and a linear hydrocarbon group; and even more preferably, the group is a saturated linear hydrocarbon group which may have substituents, a saturated alicyclic hydrocarbon group which may have substituents, or a group which is a combination of an aromatic hydrocarbon group which may have substituents and a linear hydrocarbon group. 1 In R 8a The number of carbon atoms in the saturated chain hydrocarbon group is preferably 1 to 18, more preferably 1 to 16, even more preferably 1 to 15, and even more preferably 2 to 15. 1 In R 8a The number of carbon atoms in the saturated alicyclic hydrocarbon group is preferably 3 to 18, more preferably 3 to 16, even more preferably 3 to 15, and still more preferably 3 to 10. 1 In R 8a The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 18, more preferably 6 to 15, even more preferably 6 to 12, and still more preferably 6 to 10. 1 In R 8a The number of carbon atoms in the group, which is a combination of an aromatic hydrocarbon group and a chain hydrocarbon group, is preferably 4 to 20, more preferably 5 to 18, even more preferably 6 to 16, and still more preferably 7 to 16. Furthermore, from the viewpoint of improving the solubility of compound (I) in solvents and reducing sublimation, R 1 In R 8a The hydrocarbon group represented by preferably has 5 or more carbon atoms, and more preferably 9 or more.

[0030] R 1 In R 8b Preferably, the group is a saturated chain hydrocarbon group which may have substituents, an aromatic hydrocarbon group which may have substituents, or a group which is a combination of an aromatic hydrocarbon group which may have substituents and a chain hydrocarbon group, more preferably a saturated chain hydrocarbon group which may have substituents, or an aromatic hydrocarbon group which may have substituents, and even more preferably a saturated chain hydrocarbon group or an aromatic hydrocarbon group. 1 In R 8b The number of carbon atoms in the saturated chain hydrocarbon group is preferably 1 to 18, more preferably 1 to 16, even more preferably 1 to 15, even more preferably 1 to 10, and particularly preferably 1 to 5. 1 In R 8b The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 20, more preferably 6 to 18, even more preferably 6 to 15, even more preferably 6 to 10, and particularly preferably 6 to 8. 1 In R 8b The number of carbon atoms in the group, which is a combination of an aromatic hydrocarbon group and a chain hydrocarbon group, is preferably 4 to 20, more preferably 5 to 18, even more preferably 6 to 16, and still more preferably 7 to 16.

[0031] R 1Specifically, groups represented by the following formulas (D-1) to (D-69), (E-1) to (E-25), (G-1) to (G-31), and (H-1) to (H-53) are preferred, as are formulas (D-1) to (D-18), (D-40) to (D-69), (E-2) to (E-4), (E-6) to (E-8), (E-10) to (E-12), (E-14) to (E-16), and (E-18) to ( Groups represented by formulas (E-20), (G-2) to (G-27), and (H-1) to (H-53) are more preferred, groups represented by formulas (H-1) to (H-53) are even more preferred, groups represented by formulas (H-1) to (H-5), (H-19) to (H-30), and (H-39) to (H-53) are even more preferred, and groups represented by formulas (H-1) to (H-5) and (H-19) to (H-30) are even more preferred. In the formulas, * represents a bond.

[0032] [ka]

[0033] [ka]

[0034] [ka]

[0035] [ka]

[0036] [ka]

[0037] [ka]

[0038] [ka]

[0039] [ka]

[0040] R 2 For example, hydrogen atoms, -R 8a A hydrogen atom is preferred, and a hydrogen atom is more preferred. R 2 In R 8a The group is preferably a saturated chain hydrocarbon group which may have substituents, more preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms, and even more preferably a saturated chain hydrocarbon group having 1 to 5 carbon atoms.

[0041] R 1 and R 2 The rings formed by these atoms together with the nitrogen atoms to which they are bonded may be saturated or unsaturated, and may be monocyclic or polycyclic.

[0042] R 1 and R 2 The number of ring members in the ring formed by each of these together with the nitrogen atom to which they are bonded is preferably 3 to 15, more preferably 4 to 12, and even more preferably 5 to 10.

[0043] R 1 and R 2 Specifically, the rings formed by these atoms together with the nitrogen atoms to which they are bonded are represented by the following formulas (J-1) to (J-9). In the formulas, * represents a bond.

[0044] [ka]

[0045] R 1 and R 2Specifically, rings in which the -CH2- groups that constitute the ring formed by each nitrogen atom to which they are bonded are replaced by -O- groups include the rings represented by the following formulas (Ja-1) to (Ja-6). In the formulas, * represents a bond.

[0046] [ka]

[0047] R 1 and R 2 However, rings in which the -CH2- groups that constitute the ring formed by each nitrogen atom being bonded together are replaced with -CO- groups can be specifically exemplified by the following formulas (Jb-1) to (Jb-6). In the formulas, * represents a bond.

[0048] [ka]

[0049] R 1 and R 2 Specifically, rings in which the -CH2- groups that constitute the ring formed by each nitrogen atom to which they are bonded are replaced by -S- groups include the rings represented by the following formulas (Jc-1) to (Jc-6). In the formulas, * represents a bond.

[0050] [ka]

[0051] R 1 and R 2 Specifically, rings in which the -CH2- groups that constitute the ring formed by the nitrogen atoms to which each of these groups are bonded are replaced by -S(O)2- groups, and these rings are represented by the following formulas (Jd-1) to (Jd-6). In the formulas, * represents a bond.

[0052] [ka]

[0053] R 1 and R 2 Specifically, rings in which the -CH2- groups that constitute the ring formed by the nitrogen atoms to which each of these groups are bonded are replaced with -NH- groups include the rings represented by the following formulas (Je-1) to (Je-6). In the formulas, * represents a bond.

[0054] [ka]

[0055] R 1 and R 2 The -CH2- groups, which form a ring together with the nitrogen atoms to which each is bonded, are -NR 8g Specifically, the rings that have been replaced by - are those represented by the following equations (Jf-1) to (Jf-6). In the equations, * represents a bond.

[0056] [ka]

[0057] R 8g Preferably, the group is a saturated chain hydrocarbon group which may have substituents, an aromatic hydrocarbon group which may have substituents, or a group which is a combination of an aromatic hydrocarbon group which may have substituents and a chain hydrocarbon group, more preferably a saturated chain hydrocarbon group which may have substituents, or an aromatic hydrocarbon group which may have substituents, and even more preferably a saturated chain hydrocarbon group or an aromatic hydrocarbon group. 8g The number of carbon atoms in the saturated chain hydrocarbon group is preferably 1 to 18, more preferably 1 to 16, even more preferably 1 to 15, even more preferably 1 to 10, and particularly preferably 1 to 5. 8g The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 20, more preferably 6 to 18, even more preferably 6 to 15, even more preferably 6 to 10, and particularly preferably 6 to 8. 8gThe number of carbon atoms in the group, which is a combination of an aromatic hydrocarbon group and a chain hydrocarbon group, is preferably 4 to 20, more preferably 5 to 18, even more preferably 6 to 16, and still more preferably 7 to 16.

[0058] The rings represented by the above formula (Jf-3) include, specifically, the rings represented by the following formulas (Jf-3-1) to (Jf-3-6). In the formulas, * represents a bond.

[0059] [ka]

[0060] R 1 and R 2 The ring formed by these atoms together with the nitrogen atoms to which they are bonded is the ring represented by formula (J-4), where the -CH2- constituting the ring represented by formula (J-4) is -O-, -CO-, -S-, -S(O)2-, -NH-, or -NR 8g A ring in which the - symbol is replaced is preferred, and the rings represented by formulas (J-4), (Jc-3), (Je-3), and (Jf-3) above are more preferred.

[0061] R 1 and R 2 The substituents that may be present in the ring formed by these atoms together with the nitrogen atoms to which they are bonded are: 8a , R 8b , R 8c , R 8d , R 8e , R 8f , and R 8g Examples of substituents that may be present in R are given. 1 and R 2 If the ring formed by the nitrogen atoms to which each atom is bonded has substituents, the number of substituents may be one or two or more, and the two or more substituents may be independent of each other, identical or different.

[0062] R 3 ~R 7 For example, hydrogen atoms, -R 8cA hydrogen atom is preferred, and a hydrogen atom is more preferred. R 8c The group is preferably a saturated chain hydrocarbon group which may have substituents, and more preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms.

[0063] As for compound (I), for example, in the compound represented by the following formula (Ii), R 1 and R 2 Compounds whose combination is one of those in Tables 1 to 9 below, and compounds represented by the following formula (III), R 12 (R in equation (I)) 1 and R 2 Examples of compounds include those in which the ring formed by the combination of each nitrogen atom to which it is bonded is one of those shown in Table 10 below. In Tables 1 to 10, H represents a hydrogen atom, Me represents a methyl group, Et represents an ethyl group, IBu represents an isobutyl group, and D-1 to D-69, E-1 to E-25, G-1 to G-31, and H-1 to H-53 are represented by the above formulas (D-1) to (D-69), (E-1) to (E-25), (G-1) to (G-31), and (H-1) to (H-53), respectively. The groups J-4, J-7, J-9, Ja-3, Jb-3, Jc-3, Jd-3, Je-3, and Jf-3-1 to Jf-3-6 represent the rings expressed by the above formulas (J-4), (J-7), (J-9), (Ja-3), (Jb-3), (Jc-3), (Jd-3), (Je-3), and (Jf-3-1) to (Jf-3-6), respectively.

[0064] [ka]

[0065] [Table 1]

[0066] [Table 2]

[0067] [Table 3]

[0068] [Table 4]

[0069] [Table 5]

[0070] [Table 6]

[0071] [Table 7]

[0072] [Table 8]

[0073] [Table 9]

[0074] [ka] [In formula (III), R 12 R 1 and R 2 [Each represents a ring formed by the nitrogen atom to which it is bonded.]

[0075] [Table 10]

[0076] As for compound (I), compounds (I-1) to (I-326) are preferred, compounds (I-1) to (I-163) are more preferred, compounds (I-1) to (I-18), compounds (I-40) to (I-69), compounds (I-71) to (I-73), compounds (I-75) to (I-77), compounds (I-79) to (I-81), and compounds (I-8 3) Compounds (I-85), (I-87) (I-89), (I-96) (I-121), and (I-126) (I-163) are more preferred, compound (I-126) (I-163) is even more preferred, and compound (I-126) (I-130) and compound (I-144) (I-155) are even more preferred.

[0077] Furthermore, as compound (I), Compounds (I-1) to (I-726) are preferred. Compounds (I-1) to (I-163), compound (I-327) to (I-667), and compound (I-713) to (I-726) are more preferred. Compound (I-1)~Compound (I-18), Compound (I-40)~Compound (I-69), Compound (I-71)~Compound (I-73), Compound (I-75)~ Compound (I-77), Compound (I-79) ~ Compound (I-81), Compound (I-83) ~ Compound (I-85), Compound (I-87) ~ Compound (I-89), Compound Compound (I-95) ~ Compound (I-121), Compound (I-126) ~ Compound (I-163), Compound (I-327) ~ Compound (I-344), Compound (I-3) 66) ~ Compound (I-395), Compound (I-397) ~ Compound (I-399), Compound (I-401) ~ Compound (I-403), Compound (I-405) ~ Compound (I-407), compound (I-409) to compound (I-411), compound (I-413) to compound (I-415), compound (I-421) to compound (I-447), compound (I-452) to compound (I-507), compound (I-529) to compound (I-558), compound (I-560) to compound (I-562), compound (I-564) to compound (I-566), compound (I-568) to compound (I-570), compound (I-572) to compound (I-574), compound (I-576) to compound (I-578), compound (I-584) to compound (I-610), compound (I-615) to compound (I-726) are more preferably, Compounds (I-126) to (I-163) and (I-653) to (I-667) are more preferably, Compounds (I-126) to (I-130), (I-144) to (I-155), and (I-653) to (I-661) are even more preferred.

[0078] Furthermore, in one aspect of the present invention, R in formula (I) 1 ga-SO2-R 8b According to the compound represented by the following formula (IA) (hereinafter sometimes referred to as compound (IA)), a color filter formed from a colored resin composition containing the novel compound can achieve good contrast.

[0079] [ka] [In formula (IA), R 11 This represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. R 2 ~R 7 This expresses the same meaning as above.

[0080] R 11 As a hydrocarbon group having 1 to 20 carbon atoms, R 8a , R 8b , R 8c , R 8d , R 8e , R 8f , and R 8g The same example can be given for the hydrocarbon group represented by , and the preferred range of carbon atoms is also similar.

[0081] R 11 A substituent that may be present on a hydrocarbon group having 1 to 20 carbon atoms represented by R 8a , R 8b , R 8c , R 8d , R 8e , R 8f , and R 8g Examples of substituents that may be present on a hydrocarbon group having 1 to 20 carbon atoms, represented by R, are also given. 11 The substituents that the hydrocarbon group having 1 to 20 carbon atoms represented by may have are preferably halogen atoms, and more preferably fluorine atoms. 11 When the substituents of a hydrocarbon group having 1 to 20 carbon atoms represented by are halogen atoms, it is preferable that all of the hydrogen atoms of the carbon atom to which the halogen atom is bonded are replaced by halogen atoms.

[0082] R 11Preferably, the group is a saturated linear hydrocarbon group which may have substituents, an aromatic hydrocarbon group which may have substituents, or a group which is a combination of an aromatic hydrocarbon group which may have substituents and a linear hydrocarbon group. More preferably, the group is a saturated linear hydrocarbon group which may have substituents or an aromatic hydrocarbon group which may have substituents. Even more preferably, the group is a saturated linear hydrocarbon group which may have substituents or an aromatic hydrocarbon group. Even more preferably, the group is a saturated linear hydrocarbon group which has 1 to 10 carbon atoms or an aromatic hydrocarbon group which has 6 to 10 carbon atoms. Particularly preferred is a saturated linear hydrocarbon group which has 1 to 5 carbon atoms or an aromatic hydrocarbon group which has 6 to 8 carbon atoms.

[0083] Compound (I) can be produced, for example, by reacting a compound represented by the following formula (pt1) (hereinafter sometimes referred to as compound (pt1)) with malononitrile in a solvent to produce a compound represented by the following formula (pt2) (hereinafter sometimes referred to as compound (pt2)), then by condensing compound (pt2) in a solvent using a catalyst to produce a compound represented by the following formula (pt3) (hereinafter sometimes referred to as compound (pt3)), and further by reacting compound (pt3) with a compound represented by the following formula (MA1) (hereinafter sometimes referred to as compound (MA1)) in a solvent.

[0084] [ka]

[0085] [ka] [In the formula, R 1 ~R 7 This is the same as the definition above. A This represents a hydrogen atom or a halogen atom.

[0086] R A Examples of halogen atoms represented by R include fluorine, chlorine, bromine, and iodine atoms. APreferably, the atom is a bromine atom or a hydrogen atom, and more preferably a hydrogen atom.

[0087] Examples of compounds (pt1) include acenaphthenequinone and 6-bromoacenaphthenequinone.

[0088] The amount of malononitrile used is typically 0.1 moles to 500 moles per mole of compound (pt1), preferably 0.3 moles to 400 moles, more preferably 0.5 moles to 300 moles, and even more preferably 0.8 moles to 200 moles.

[0089] In the reaction between compound (pt1) and malononitrile, it is preferable to use a solvent (especially an organic solvent) that has been thoroughly deoxygenated and / or dehydrated to suppress side reactions, and dehydrated acetonitrile is more preferable.

[0090] The amount of solvent used in the reaction between compound (pt1) and malononitrile is typically 0.1 to 1000 parts by mass per 1 part by mass of compound (pt1).

[0091] The reaction temperature when compound (pt1) reacts with malononitrile is typically between -100°C and 300°C. The reaction time when compound (pt1) reacts with malononitrile is typically between 0.5 hours and 300 hours.

[0092] Examples of compounds (pt2) include 2-(2-oxo-2H-acenaphthylene-1-ylidene)-malononitrile and 2-(6-bromo-2-oxo-2H-acenaphthylene-1-ylidene)-malononitrile.

[0093] Catalysts used in the production of compound (pt3) include palladium compounds such as tris(dibenzylideneacetone)dipalladium(O), bis(dibenzylideneacetone)palladium(O), palladium(II) acetate, palladium(II) chloride, sodium tetrachloropalladium(II)ate, palladium(II)(π-cinnamyl) chloride (dimer), allylpalladium(II) chloride (dimer), bis(benzonitrile)palladium(II) dichloride, and bis(acetonitrile)palladium(II) dichloride; triethylamine, 4-(N,N-dimethylamino)pyridine, pyridine, piperidine, and N,N-diiso Examples include organic bases such as propylethylamine, 1,4-diazabicyclo[2.2.2]octane, 1,5-diazabicyclo[4.3.0]-5-nonene, and 1,8-diazabicyclo[5.4.0]-7-undecene; metal alkoxides such as sodium methoxide, sodium ethoxide, sodium tert-butoxide, and potassium tert-butoxide; and inorganic bases such as sodium acetate, potassium phosphate, lithium hydroxide, sodium hydroxide, potassium hydroxide, cesium hydroxide, lithium carbonate, sodium carbonate, potassium carbonate, cesium carbonate, lithium bicarbonate, sodium bicarbonate, potassium bicarbonate, and cesium bicarbonate. Preferably, the substances are cesium carbonate, potassium carbonate, potassium phosphate, triethylamine, 4-(N,N-dimethylamino)pyridine, N,N-diisopropylethylamine, 1,4-diazabicyclo[2.2.2]octane, tris(dibenzylideneacetone)dipalladium(0), and palladium(II) acetate.

[0094] The amount of catalyst used in the condensation reaction of compound (pt2) can be any amount that is catalytic, for example, 0.1 moles to 50 moles per 100 moles of compound (pt2), preferably 0.5 moles to 40 moles, and more preferably 1.0 mole to 30 moles.

[0095] When using a metal catalyst such as a palladium compound as a catalyst in the condensation reaction of compound (pt2), a specific ligand may be coordinated to the metal catalyst. Examples of ligands include trimethylphosphine, triethylphosphine, tri(n-butyl)phosphine, tri(isopropyl)phosphine, tri(tert-butyl)phosphine, tricyclohexylphosphine, diphenyl(methyl)phosphine, triphenylphosphine, 2-dicyclohexylphosphinobiphenyl, 2-dicyclohexylphosphino-2'-methylbiphenyl, 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl, 2-dicyclohexylphosphino-2'-(N,N'-dimethylamino)biphenyl, and 2-diphenylphosphino-2'-(N,N'-dimethylamino)biphenyl.

[0096] The amount of ligand used in the condensation reaction of compound (pt2) is, for example, 0.05 moles to 100 moles per mole of metal catalyst, preferably 0.1 moles to 80 moles, more preferably 0.5 moles to 50 moles, and even more preferably 0.8 moles to 30 moles.

[0097] In the condensation reaction of compound (pt2) in the presence of a catalyst, the following solvents are used: 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, tetrahydrofuran, ethylene glycol dimethyl ether, and diethylene glycol dimethyl ether; ketone solvents such as acetone and methyl isobutyl ketone; and ester solvents such as ethyl acetate. Examples include: aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1,2-dichlorobenzene; amide solvents such as N,N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid; and imidazole. Water, nitrile solvents, and ether solvents are preferred, with water, acetonitrile, ethylene glycol dimethyl ether, and diethylene glycol dimethyl ether being more preferred, and water and acetonitrile being even more preferred.

[0098] In the condensation reaction of compound (pt2) in the presence of a catalyst, the amount of solvent used is typically 0.1 to 1000 parts by mass per 1 part by mass of compound (pt2).

[0099] The reaction temperature for the condensation reaction of compound (pt2) in the presence of a catalyst is typically between -100°C and 300°C. Furthermore, the reaction time for the condensation reaction of compound (pt2) in the presence of a catalyst is typically between 0.5 hours and 300 hours.

[0100] Examples of compounds (pt3) include 1-oxo-1H-phenalene-2,3-dicarbonitric and 6-bromo-1-oxo-1H-phenalene-2,3-dicarbonitric.

[0101] Examples of compounds (MA1) include 1-butylamine, isobutylamine, 2-ethylhexylamine, 1-hexylheptylamine, 1-dodecylamine, 1-tetradecylamine, 3,3-diphenylpropylamine, 1-hexylamine, cyclopentylamine, cyclohexylamine, 4-methylbenzylamine, 4-(tert-butyl)benzylamine, 4-ethyl aminobutyrate, 1-octylamine, diisobutylamine, piperidine, 1-methylpiperazine, 1-phenylpiperazine, thiomorpholine, aniline, N-ethylaniline, methylsulfonamide, phenylsulfonamide, trifluoromethylsulfonamide, tert-butylsulfonamide, benzylsulfonamide, and 4-fluorophenylsulfonamide.

[0102] The amount of compound (MA1) used is typically 0.4 moles to 20 moles per mole of compound (pt3), preferably 0.5 moles to 15 moles, and more preferably 0.6 moles to 10 moles.

[0103] A catalyst may be used in the reaction between compound (pt3) and compound (MA1). Examples of catalysts used in the reaction between compound (pt3) and compound (MA1) are the same as those used in the production of compound (pt3), and the preferred form of the catalyst is also the same.

[0104] The amount of catalyst used in the reaction between compound (pt3) and compound (MA1) can be any amount that is catalytic, for example, 0.1 moles to 50 moles per 100 moles of compound (pt3), preferably 0.5 moles to 40 moles, and more preferably 1.0 mole to 30 moles.

[0105] When a metal catalyst is used in the reaction between compound (pt3) and compound (MA1), a specific ligand may be coordinated to the metal catalyst. Examples of ligands include those used in the production of compound (pt3).

[0106] The amount of ligand used in the reaction between compound (pt3) and compound (MA1) is, for example, 0.05 moles to 100 moles per mole of metal catalyst, preferably 0.1 moles to 80 moles, more preferably 0.5 moles to 50 moles, and even more preferably 0.8 moles to 30 moles.

[0107] In the reaction between compound (pt3) and compound (MA1), water, nitrile solvents, and ether solvents are preferred as solvents, and water, acetonitrile, ethylene glycol dimethyl ether, and diethylene glycol dimethyl ether are more preferred. Furthermore, in order to suppress side reactions, it is preferable to use solvents (especially organic solvents) that have been sufficiently deoxygenated and / or dehydrated, with dehydrated acetonitrile and dehydrated ethylene glycol dimethyl ether being more preferred, and dehydrated acetonitrile being even more preferred.

[0108] The amount of solvent used in the reaction between compound (pt3) and compound (MA1) is typically 0.1 to 1000 parts by mass per 1 part by mass of compound (pt3).

[0109] In the reaction between compound (pt3) and compound (MA1), a base may be present to ensure the reaction proceeds efficiently. The base may be an organic or inorganic base, with organic bases being preferred. Tertiary amines such as trimethylamine, triethylamine, tri-n-propylamine, tri-n-butylamine, diisopropylethylamine, tri-n-octylamine, tri-n-decylamine, triphenylamine, N,N-dimethylaniline, N,N,N',N'-tetramethylethylenediamine, N-methylpyrrolidine, and 4-dimethylaminopyridine are more preferred.

[0110] When a base is used in the reaction between compound (pt3) and compound (MA1), the amount of base used is usually 0.1 moles to 50 moles per mole of compound (pt3), preferably 0.5 moles to 30 moles.

[0111] The reaction temperature when compound (pt3) and compound (MA1) are reacted is typically between -100°C and 300°C. The reaction time when compound (pt3) and compound (MA1) are reacted is typically between 0.5 hours and 300 hours.

[0112] After each of the above reactions is complete, the method for extracting the target compound is not particularly limited and 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 are not particularly limited, but examples include X-ray crystallography, mass spectrometry (LC), NMR analysis, and elemental analysis. X-ray crystallography can be performed, for example, in accordance with Chemistry of Materials, 2012, Vol. 24, pp. 4647-4652.

[0113] Compound (IA) can be produced by using the following compound (MA1-1) as compound (MA1) in the manufacturing process of compound (I) described above.

[0114] [ka] [In the formula, R 2 and R 11 This is the same as the definition above.

[0115] The content of compound (I) may be 100% by mass relative to the total amount of colorant (A), and the lower limit may be, for example, 0.1% by mass or more, 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.

[0116] <<Coloring agent (A1)>> The colorant (A) of the present invention may contain dyes other than the compound (I) (hereinafter sometimes referred to as dye (A1-1)) and / or pigments (hereinafter sometimes referred to as pigment (A1-2)) (hereinafter, dye (A1-1) and pigment (A1-2) may be collectively referred to as colorant (A1)). These may be used alone or in combination of two or more.

[0117] As long as the compound (I) is not included, known dyes can be used as the dye (A1-1), and examples thereof include solvent dyes, acid dyes, direct dyes, mordant dyes, etc. 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 the Dyeing Notes (Color Dyeing Co., Ltd.). Also, according to the chemical structure, 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, phthalocyanine dyes, perylene dyes, quinophthalone dyes, isoindoline dyes, etc. can be mentioned. Among these, organic solvent-soluble dyes are preferred.

[0118] Specifically, dyes with the following Color Index (C.I.) numbers can be mentioned. C.I. Solvent Yellow 4, 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 117, 162, 163, 167, 189; C.I. Solvent Red 24, 45, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 218, 222, 227, 230, 245, 247; C.I. Solvent Orange 2, 7, 11, 15, 26, 41, 54, 56, 77, 86, 99; C.I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60; C.I. Solvent Blue 4, 5, 14, 18, 35, 36, 37, 38, 44, 45, 58, 59, 59:1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139; C.I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35; etc. C.I. Solvent Dyes, C.I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;<00,00909>C.I. Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 15, 160, 172, 176, 182, 183, 195, 198, 206, 211, 215, 216, 217, 227, 228, 249, 252, 257, 258, 260, 261, 266, 268, 270, 274, 277, 280, 281, 289, 308, 312, 315, 316, 339, 3, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426; CI Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173; CI Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102; CI Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 18, 22, 23, 24, 25, 26, 27, 29, 34, 38, 40, 41, 42, 43, 45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90:1, 91, 92, 93, 93:1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123 ,126,127,129,130,131,138,140,142,143,147,150,151,154,158,161,166,167,168,170,171,175,182,183,184,187,192,199,203,204,205,210,213,229,234,236,242,243,249,256,259,267,269,278,280,285,290,296,315,324:1,335,340; CI Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50:1, 58, 63, 65, 80, 104, 105, 106, 109; and other CI Acid dyes. CI Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141; CI Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 232, 233, 234, 241, 243, 246, 250; CI Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107; CI Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104; CI Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 87, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 16 6, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293; CI Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82; and other CI Direct dyes. CI Disperse Yellow 51, 54, 76; CI Disperse Violet 26, 27; CI Disperse Blue 1, 14, 56, 6; and other CI disperse dyes. CI Basic Red 1, 10; CI Basic Blue 1, 3, 5, 7, 9, 19, 21, 22, 24, 25, 26, 28, 29, 40, 41, 45, 47, 54, 58, 59, 60, 64, 65, 66, 67, 68, 81, 83, 88, 89; CI Basic Violet 2; CI Basic Red 9; CI Basic Green 1; and other CI Basic dyes, CI Reactive Yellow 2, 76, 116; CI Reactive Orange 16; CI Reactive Red 36; and other CI reactive dyes, CI Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65; CI Modant Red 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38, 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95; CI Modern Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; CI Mordant Violet 1, 1:1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28, 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58; CI Modern Blue 1, 2, 3, 7, 8, 9, 12, 13, 15, 16, 19, 20, 21, 22, 23, 24, 26, 30, 31, 32, 39, 40, 41, 43, 44, 48, 49, 53, 61, 74, 77, 83, 84; CI Modant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53; and other CI Modant dyes. CI Bat Green 1; and other CI Bat dyes, etc.

[0119] As for the pigment (A1-2), any known pigment can be used, as long as it does not contain compound (I). Examples include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists).

[0120] Pigments classified as pigments include, specifically, yellow pigments such as CI Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, and 231; CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73, and other orange pigments; CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 178, 179, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273, and other red pigments; CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60, and other blue pigments; CI Pigment Violet 1, 19, 23, 32, 36, 38, and other violet color pigments; Green pigments such as CI Pigment Green 7, 36, 58, 59, 62, 63; CI Pigment Brown 23, 25, and other brown pigments; Examples include black pigments such as CI Pigment Black 1, 7, 31, and 32; and so on.

[0121] When coloring agent (A) contains coloring agent (A1), the content of coloring agent (A1) in coloring agent (A) is, for example, 0.1% by mass or more and 99.9% by mass or less, preferably 1% by mass or more and 50% by mass or less, relative to the total amount of coloring agent (A).

[0122] If the colored resin composition contains a solvent (E), a colored composition containing a colorant (A) and solvent (E) (hereinafter sometimes referred to as a colorant-containing liquid) may be prepared in advance, and then the colored resin composition may be prepared using this colored composition. If the colorant (A) does not dissolve in solvent (E), for example, if the colorant (A) contains pigments (A1-2), the colored composition can be prepared by dispersing the colorant (A) in solvent (E) and mixing it. The colored composition may contain some or all of the solvent (E) contained in the colored resin composition.

[0123] The solid content in the colored composition is less than 100% by mass of the total amount of the colored composition, preferably 0.01% by mass or more and 99.99% by mass or less, more preferably 0.1% by mass or more and 99.9% by mass or less, even more preferably 0.1% by mass or more and 99% by mass or less, even more preferably 1% by mass or more and 90% by mass or less, particularly preferably 1% by mass or more and 80% by mass or less, even more preferably 1% by mass or more and 70% by mass or less, especially preferably 1% by mass or more and 60% by mass or less, and most preferably 1% by mass or more and 50% by mass or less.

[0124] The content of coloring agent (A) in the colored composition is 100% by mass or less, preferably 0.001% by mass or more and 99.999% by mass or less, more preferably 0.01% by mass or more and 99% by mass or less, even more preferably 0.1% by mass or more and 95% by mass or less, even more preferably 0.5% by mass or more and 90% by mass or less, and particularly preferably 1.0% by mass or more and 80% by mass or less, based on the total amount of solids in the colored composition.

[0125] The coloring agent (A) may be subjected to rosin treatment, surface treatment using derivatives into which acidic or basic groups have been introduced, grafting treatment of the surface of the coloring agent (A) with polymer compounds, atomization treatment by sulfuric acid atomization method, salt milling method, etc., washing treatment with organic solvents or water to remove impurities, removal treatment of ionic impurities by ion exchange method, etc. The particle size of the coloring agent (A) is preferably substantially uniform.

[0126] By performing a dispersion treatment on the colorant (A) while containing a dispersant, the colorant (A) can be uniformly dispersed in the solution. When two or more kinds of the colorant (A) are used in combination, each may be dispersed separately, or a plurality of kinds may be mixed and dispersed.

[0127] Examples of the dispersant include surfactants, and any of cationic, anionic, nonionic, and amphoteric surfactants may be used. Specifically, surfactants such as polyester-based, polyamine-based, and acrylic-based surfactants are included. These dispersants may be used alone or in combination of two or more. Examples of the dispersant represented by the trade name include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Ltd.), EFKA (registered trademark) (manufactured by BASF), Ajisper (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Inc.), Disperbyk (registered trademark) (manufactured by BYK Chemie GmbH), BYK (registered trademark) (manufactured by BYK Chemie GmbH), etc.

[0128] When using a dispersant, 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 still more preferably 15 parts by mass or more and 1,000 parts by mass or less, based on 100 parts by mass of the colorant (A) in the coloring composition. When the amount of the dispersant used is within the above range, a coloring composition with a more uniform dispersion state tends to be obtained.

[0129] When preparing a colored resin composition using a coloring composition containing the colorant (A) and the solvent (E) in advance, the coloring composition may contain a part or all, preferably a part, of the resin (B) contained in the colored resin composition in advance. By including the resin (B) in advance, the dispersion stability of the coloring composition can be further improved.

[0130] If the coloring composition contains resin (B), the content of resin (B) is, for example, 0.01 parts by mass or more and 10,000 parts by mass or less, preferably 0.01 parts by mass or more and 8,000 parts by mass or less, more preferably 0.01 parts by mass or more and 5,000 parts by mass or less, and even more preferably 0.1 parts by mass or more and 3,000 parts by mass or less, based on 100 parts by mass of colorant (A) in the coloring composition.

[0131] The content of the coloring agent (A) is preferably 0.1% to 50% by mass, more preferably 0.5% to 40% by mass, even more preferably 1.0% to 30% by mass, and even more preferably 1.5% to 20% by mass, based on the total amount of solids in the colored resin composition. When the content of the coloring agent (A) is within the above range, the color density when used as a color filter is sufficient, and the required amount of resin (B) can be included in the composition, so it is preferable that a pattern with sufficient mechanical strength can be formed. Herein, "total amount of solids" as used herein refers to the amount obtained by subtracting the solvent content from the total amount of the colored resin composition. The total amount of solids and the content of each component therein can be measured by known analytical means such as liquid chromatography or gas chromatography.

[0132] The content ratio of colorant (A) to resin (B) described later in the colored resin composition (resin (B) / colorant (A)) is preferably 2.0 or more by mass, more preferably 3.0 or more, even more preferably 4.0 or more, preferably 12 or less, more preferably 10 or less, and even more preferably 8.0 or less.

[0133] <Resin (B)> Unlike thermoplastic resins, resin (B) is not particularly limited as long as it is used for forming photoresists, but it is preferably an alkali-soluble resin, and preferably an alkali-soluble resin containing a carboxylic acid.

[0134] Examples of resin (B) include the following resins [K1] to [K6]. Resin [K1]; a copolymer having structural units derived from at least one monomer (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter sometimes referred to as "(a)" or "monomer (a)") and structural units derived from monomer (b) having a cyclic ether structure with 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b)" or "monomer (b)"); Resin [K2]; a copolymer having structural units derived from (a) and structural units derived from (b) and a monomer (c) copolymerizable with (a) (however different from (a) and (b)) (hereinafter sometimes referred to as "(c)" or "monomer (c)"); Resin [K3]; a copolymer having structural units derived from (a) and structural units derived from (c); Resin [K4]; a copolymer having structural units derived from (a) to which (b) is added and structural units derived from (c); Resin [K5]; a copolymer having structural units derived from (b) to which (a) is added and structural units derived from (c); A copolymer having a structural unit obtained by adding (a) to a resin [K6] and further adding a carboxylic acid anhydride, and a structural unit obtained by adding (c).

[0135] Examples of monomers (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, 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 carboxyl groups, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene; Carboxylic acid anhydrides such as the anhydrides of the above unsaturated dicarboxylic acids, excluding fumaric acid and mesaconic acid; Unsaturated mono(meth)acryloyloxyalkyl) esters of divalent or higher polycarboxylic acids such as mono(2-(meth)acryloyloxyethyl) succinate and mono(2-(meth)acryloyloxyethyl) phthalate; Examples include unsaturated acrylates containing both a hydroxyl group and a carboxyl group in the same molecule, such as α-(hydroxymethyl)acrylic acid. Of these, acrylic acid, methacrylic acid, and maleic anhydride are preferred in terms of copolymerization reactivity and the solubility of the resulting resin in alkaline aqueous solutions. In this specification, "(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.

[0136] Monomer (b) refers to a polymerizable compound having a cyclic ether structure with 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. Preferably, monomer (b) is a monomer having a cyclic ether with 2 to 4 carbon atoms and a (meth)acryloyloxy group.

[0137] Examples of monomer (b) include monomers having an oxyranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b1)" or "monomer (b1)"), monomers having an oxetanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b2)" or "monomer (b2)"), and monomers having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as "(b3)" or "monomer (b3)").

[0138] Examples of monomers (b1) include monomers having a structure in which unsaturated aliphatic hydrocarbons are epoxidized (hereinafter sometimes referred to as "(b1-1)" or "monomer (b1-1)") and monomers having a structure in which unsaturated alicyclic hydrocarbons are epoxidized (hereinafter sometimes referred to as "(b1-2)" or "monomer (b1-2)").

[0139] As monomer (b1-1), monomers having a glycidyl group and an ethylenically unsaturated bond are preferred. Specifically as monomer (b1-1), glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzylglycidyl ether, m-vinylbenzylglycidyl ether, p-vinylbenzylglycidyl ether, α-methyl-o-vinylbenzylglycidyl ether, α-methyl-m-vinylbenzylglycidyl ether, α-methyl-p-vinylbenzylglycidyl ether, 2,3-bis( Examples include glycidyloxymethyl)styrene, 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.

[0140] Examples of monomers (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (e.g., Celoxide® 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer® A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth)acrylate (e.g., Cyclomer® M100; manufactured by Daicel Corporation), compounds represented by formula (BI), and compounds represented by formula (BII).

[0141] [ka]

[0142] [In formulas (BI) and (BII), R a and R b Each of these 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 hydroxyl group. X a and X b These are independent of each other, single bonds, *-R c -, *-R c -O-, *-R c -S- or *-R c Represents -NH- R c This represents an alkanediyl group with 1 to 6 carbon atoms. * represents a bond with O.

[0143] Examples of alkyl groups having 1 to 4 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, and tert-butyl groups.

[0144] Examples of alkyl groups in which a hydrogen atom is substituted with hydroxyl include hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1-hydroxy-1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, and 4-hydroxybutyl group.

[0145] R a and R b Preferably, the group can be a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group, or a 2-hydroxyethyl group, and more preferably a hydrogen atom or a methyl group.

[0146] Examples of alkanediyl groups include methylene, ethylene, propane-1,2-diyl, propane-1,3-diyl, butane-1,4-diyl, pentane-1,5-diyl, and hexane-1,6-diyl.

[0147] X a and X b Preferably, the bonds include single bonds, methylene groups, ethylene groups, *-CH2-O- (* represents a bond with O) groups, and *-CH2CH2-O- groups, and more preferably, single bonds and *-CH2CH2-O- groups (* represents a bond with O).

[0148] Compounds represented by formula (BI) include those represented by any of formulas (BI-1) to (BI-15). Among these, 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.

[0149] [ka]

[0150] Compounds represented by formula (BII) include compounds represented by any of formulas (BII-1) to (BII-15), among which compounds represented by formulas (BII-1), (BII-3), (BII-5), (BII-7), (BII-9), and (BII-11) to (BII-15) are preferred, and compounds represented by formulas (BII-1), (BII-7), (BII-9), and (BII-15) are more preferred.

[0151] [ka]

[0152] The compound represented by formula (BI) and the compound represented by formula (BII) may be used individually, or the compound represented by formula (BI) and the compound represented by formula (BII) may be used in combination. When used in combination, the content ratio of the compound represented by formula (BI) and the compound represented by formula (BII) is preferably 5:95 to 95:5 on a molar basis, more preferably 10:90 to 90:10, and even more preferably 20:80 to 80:20.

[0153] 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 preferred. Examples of monomer (b2) include 3-methyl-3-(meth)acryloyloxymethyl oxetane, 3-ethyl-3-(meth)acryloyloxymethyl oxetane, 3-methyl-3-(meth)acryloyloxyethyl oxetane, and 3-ethyl-3-(meth)acryloyloxyethyl oxetane.

[0154] As the monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond, a monomer having a tetrahydrofuryl group and a (meth)acryloyloxy group is more preferred. Examples of monomer (b3) include tetrahydrofuryl acrylate (e.g., Viscoat V#150, manufactured by Osaka Organic Chemical Industry Co., Ltd.) and tetrahydrofuryl methacrylate.

[0155] Examples of monomers (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 ] Decane-8-yl(meth)acrylate (in the relevant technical field, it is commonly called "dicyclopentanyl(meth)acrylate". It is also sometimes called "tricyclodecyl(meth)acrylate"), tricyclo[5.2.1.0 2,6 Decane-9-yl (meth)acrylate, tricyclo[5.2.1.0 2,6 ] Decen-8-yl(meth)acrylate (commonly known as "dicyclopentenyl(meth)acrylate" in the relevant art), tricyclo[5.2.1.0 2,6 (meth)acrylic acid esters such as decen-9-yl (meth)acrylate, dicyclopentanyloxyethyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, allyl (meth)acrylate, propargyl (meth)acrylate, phenyl (meth)acrylate, naphthyl (meth)acrylate, and benzyl (meth)acrylate; Hydroxy group-containing (meth)acrylic acid esters such as 2-hydroxyethyl (meth)acrylate and 2-hydroxypropyl (meth)acrylate; Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate; Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybic Chlo[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 -2-ene, 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; Dicarbonylimide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimide benzoate, N-succinimidyl-4-maleimide butyrate, N-succinimidyl-6-maleimide caproate, N-succinimidyl-3-maleimide propionate, and N-(9-acridinyl)maleimide; Examples include vinyl group-containing aromatic compounds such as styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, and p-methoxystyrene; vinyl group-containing nitriles such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; vinyl group-containing amides such as (meth)acrylamide; esters such as vinyl acetate; and dienes such as 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene. Of these, styrene, vinyltoluene, and tricyclotoluene were selected based on their copolymerization reactivity and heat resistance. [5.2.1.0 2,6 Decane-8-yl(meth)acrylate, tricyclo[5.2.1.0 2,6 Decane-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]hepto-2-ene, and benzyl (meth)acrylate are preferred.

[0156] In resin [K1], the ratio of structural units derived from each is, among all structural units constituting resin [K1], (a) Structural units derived from (a); 2-60 mol% (b) Structural units derived from (b); 40-98 mol% It is preferable that this be the case. (a) Structural units derived from (a); 10-50 mol% (b) Structural units derived from (b); 50-90 mol% It is preferable that it be so. When the ratio of structural units of resin [K1] falls within the above range, the storage stability of the colored resin composition, the developability when forming a colored pattern, and the solvent resistance of the resulting optical filter tend to be excellent.

[0157] The resin [K1] can be manufactured, for example, by referring to the method described in the literature "Experimental Methods for Polymer Synthesis" (by Takayuki Otsu, published by Kagaku Dojin Co., Ltd., 1st edition, 1st printing, March 1, 1972) and the cited literature.

[0158] Specifically, a method involves placing predetermined amounts of (a) and (b), a polymerization initiator, and a solvent into a reaction vessel, creating a deoxygenated atmosphere by, for example, replacing oxygen with nitrogen, and heating and maintaining the temperature while stirring. The polymerization initiator and solvent used here are not particularly limited and can be those commonly used in the field. For example, examples of polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.), and the solvent can be any solvent that dissolves each monomer. Examples of solvents (E) in the colored resin composition of the present invention include the solvents described later.

[0159] The resulting copolymer may be used as is after the reaction, or after being concentrated or diluted, or after being extracted as a solid (powder) by methods such as reprecipitation. In particular, by using the solvent contained in the colored resin composition of the present invention as the solvent during polymerization, the solution after the reaction can be used directly in the preparation of the colored resin composition of the present invention, thereby simplifying the manufacturing process of the colored resin composition of the present invention.

[0160] In resin [K2], the ratio of structural units derived from each is, among all structural units constituting resin [K2], (a) Structural units derived from (a); 2-45 mol% (b) Structural units derived from (b); 2-95 mol% (c) Structural units derived from (c); 1-65 mol% It is preferable that this be the case. (a) Structural units derived from (a); 5-40 mol% (b) Structural units derived from (b); 5-80 mol% (c) Structural units derived from (c); 5-60 mol% It is preferable that it be so. When the ratio of structural units of resin [K2] is within the above range, the colored resin composition tends to have excellent storage stability, developability when forming colored patterns, and solvent resistance, heat resistance, and mechanical strength of the resulting optical filter.

[0161] Resin [K2] can be manufactured, for example, in the same manner as described as the method for manufacturing resin [K1].

[0162] In resin [K3], the ratio of structural units derived from each is, out of the total structural units constituting resin [K3], (a) Structural units derived from (a); 2-60 mol% (c) Structural units derived from this structure; 40-98 mol% It is preferable that this be the case. (a) Structural units derived from (a); 10-50 mol% (c) Structural units derived from (c); 50-90 mol% It is preferable that it be so. Resin [K3] can be manufactured, for example, in the same manner as described as the method for manufacturing resin [K1].

[0163] The resin [K4] can be produced by obtaining a copolymer of (a) and (c), and adding the cyclic ether having 2 to 4 carbon atoms of (b) to the carboxylic acid and / or carboxylic acid anhydride of (a). First, a copolymer of (a) and (c) is produced in the same manner as described for the production of resin [K1]. In this case, it is preferable that the ratio of structural units derived from each is the same as that given for resin [K3].

[0164] Next, a portion of the carboxylic acid and / or carboxylic acid anhydride derived from (a) in the copolymer is reacted with a cyclic ether having 2 to 4 carbon atoms that (b) possesses. Following the production of the copolymer of (a) and (c), the atmosphere inside the flask is replaced from nitrogen to air, and (b), a reaction catalyst for the reaction between a carboxylic acid or carboxylic acid anhydride and a cyclic ether (e.g., tris(dimethylaminomethyl)phenol) and a polymerization inhibitor (e.g., hydroquinone) are added to the flask and the mixture is reacted at, for example, 60 to 130°C for 1 to 10 hours to produce resin [K4]. The amount of (b) used is preferably 5 to 80 moles, more preferably 10 to 75 moles, per 100 moles of (a). This range tends to result in a good balance of storage stability of the colored resin composition, developability when forming patterns, and solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting patterns. Since the cyclic ether is highly reactive and unreacted (b) is less likely to remain, (b1) is preferred as the (b) used in the resin [K4], and (b1-1) is even more preferred. The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b), and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total amount of (a), (b), and (c). The reaction conditions, such as the preparation method, reaction temperature, and time, can be adjusted as appropriate, taking into account the manufacturing equipment and the amount of heat generated by polymerization. Similarly, the preparation method and reaction temperature can be adjusted as appropriate, taking into account the manufacturing equipment and the amount of heat generated by polymerization.

[0165] As a first step, resin [K5] is produced in the same manner as the production method for resin [K1] described above to obtain a copolymer of (b) and (c). As described above, the obtained copolymer may be used as is after the reaction, or a concentrated or diluted solution may be used, or it may be used after being extracted as a solid (powder) by methods such as reprecipitation. The ratios of structural units derived from (b) and (c) are, in relation to the total number of moles of all structural units constituting the copolymer, respectively: (b) Structural units derived from (b); 5-95 mol% (c) Structural units derived from (c); 5-95 mol% It is preferable that this be the case. (b) Structural units derived from (b); 10-90 mol% (c) Structural units derived from (c); 10-90 mol% It is preferable that it be so.

[0166] Furthermore, resin [K5] can be obtained by reacting a cyclic ether derived from (b) in the copolymer of (b) and (c) with a carboxylic acid or carboxylic acid anhydride from (a) under the same conditions as for the production of resin [K4]. The amount of (a) used to react with the copolymer is preferably 5 to 80 moles per 100 moles of (b). Since the cyclic ether is highly reactive and unreacted (b) is less likely to remain, (b1) is preferred as the (b) used in the resin [K5], and (b1-1) is even more preferred.

[0167] Resin [K6] is a resin obtained by further reacting resin [K5] with a carboxylic acid anhydride. The hydroxyl group generated by the reaction of a cyclic ether with a carboxylic acid or carboxylic acid anhydride is reacted with the carboxylic acid anhydride. Examples of carboxylic acid anhydrides include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, and 5,6-dicarboxybicyclo[2.2.1]hepto-2-ene anhydride. The amount of carboxylic acid anhydride used is preferably 0.5 to 1 mole per mole of (a).

[0168] Specific resins (B) include 3,4-epoxycyclohexylmethyl(meth)acrylate / (meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 ] Resins such as decyl acrylate / (meth)acrylic acid copolymer [K1]; glycidyl (meth)acrylate / benzyl (meth)acrylate / (meth)acrylic acid copolymer, glycidyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, 3,4-epoxy tricyclo[5.2.1.02,6 Decyl acrylate / (meth)acrylic acid / N-cyclohexyl maleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 2,6 Resins such as decyl acrylate / (meth)acrylic acid / N-cyclohexyl maleimide / 2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyl oxetane / (meth)acrylic acid / styrene copolymer [K2]; resins such as benzyl (meth)acrylate / (meth)acrylic acid copolymer, styrene / (meth)acrylic acid copolymer [K3]; resins obtained by adding glycidyl (meth)acrylate to benzyl (meth)acrylate / (meth)acrylic acid copolymer, resins obtained by adding glycidyl (meth)acrylate to tricyclodecyl (meth)acrylate / styrene / (meth)acrylic acid copolymer, tricyclodecyl Examples of resins include those obtained by adding glycidyl(meth)acrylate to a (meth)acrylate / benzyl(meth)acrylate / (meth)acrylic acid copolymer [K4]; resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl(meth)acrylate / glycidyl(meth)acrylate, resins obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl(meth)acrylate / styrene / glycidyl(meth)acrylate [K5]; and resins obtained by reacting tetrahydrophthalic anhydride with a resin obtained by reacting (meth)acrylic acid with a copolymer of tricyclodecyl(meth)acrylate / glycidyl(meth)acrylate [K6].

[0169] The resin (B) is more preferably resin [K1] or resin [K2], and is particularly preferably resin [K1].

[0170] The weight-average molecular weight (Mw) of resin (B) in terms of polystyrene is preferably 1,000 to 100,000, more preferably 2,000 to 50,000, and even more preferably 3,000 to 30,000. When the weight-average molecular weight is within the above range, the solubility of the unexposed areas in the developer is high, and the residual film rate and hardness of the resulting pattern tend to be high. The degree of dispersion of resin (B) [weight-average molecular weight (Mw) / number-average molecular weight (Mn)] is preferably 1 or more and 6 or less, more preferably 1.001 or more and 5 or less, and even more preferably 1.01 or more and 4 or less.

[0171] The acid value (solid content equivalent) of resin (B) is preferably 10 mg-KOH / g or more and 300 mg-KOH / g or less, more preferably 20 mg-KOH / g or more and 250 mg-KOH / g or less, even more preferably 25 mg-KOH / g or more and 200 mg-KOH / g or less, even more preferably 30 mg-KOH / g or more and 150 mg-KOH / g or less, and particularly preferably 60 mg-KOH / g or more and 135 mg-KOH / g or less. Here, the acid value is measured as the amount of potassium hydroxide (mg) required to neutralize 1 g of resin, and can be determined, for example, by titration using an aqueous potassium hydroxide solution.

[0172] The content of resin (B) is preferably 5 to 90% by mass, more preferably 5 to 50% by mass, even more preferably 10 to 40% by mass, and even more preferably 15 to 35% by mass, based on 100% by mass of the solid content of the colored resin composition. When the content of resin (B) is within the above range, the solubility of the unexposed areas in the developer tends to be high.

[0173] <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 include compounds having polymerizable ethylenically unsaturated bonds, and is preferably a (meth)acrylic acid ester compound.

[0174] Examples of polymerizable compounds having one ethylenically unsaturated bond include nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, and monomers (a), (b), and (c) mentioned above.

[0175] Examples of polymerizable compounds 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.

[0176] In particular, 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, and Examples 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, with dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate being preferred.

[0177] The weight-average molecular weight of the polymerizable compound (C) is preferably 50 to 4,000, more preferably 70 to 3,500, even more preferably 100 to 3,000, even more preferably 150 to 2,900, and particularly preferably 250 to 1,500.

[0178] The content of polymerizable compound (C) may be, for example, 1% by mass or more and 99% by mass or less, preferably 5% by mass or more and 90% by mass or less, more preferably 10% by mass or more and 80% by mass or less, and even more preferably 20% by mass or more and 70% by mass or less, based on the total amount of solids in the colored resin composition.

[0179] <Polymerization initiator (D)> The polymerization initiator (D) is not particularly limited as long as it is a compound that generates active radicals, acids, etc., upon the action of light or heat and can initiate polymerization; any known polymerization initiator can be used.

[0180] Examples of polymerization initiators (D) include O-acyloxime compounds, alkylphenone compounds, biimidazole compounds, triazine compounds, and acylphosphine oxide compounds.

[0181] Examples of O-acyloxime compounds 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-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropane-1-one-2-imine, N-acetoxy-1-[ Examples include 9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-{2-methyl-4-(3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy)benzoyl}-9H-carbazole-3-yl]ethane-1-imine, N-acetoxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-imine, and N-benzoyloxy-1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazole-3-yl]-3-cyclopentylpropane-1-one-2-imine. Furthermore, commercially available O-acyloxime compounds such as Irgacure® OXE01, OXE02 (both manufactured by BASF) and N-1919 (manufactured by ADEKA Corporation) may be used. Among these, 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-cyclopentylpropane-1-one-2-imine is preferred as the O-acyloxime compound, with N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine being more preferred.

[0182] Examples of alkylphenone compounds 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. Commercial alkylphenone compounds such as Irgacure® 369, 907, and 379 (all manufactured by BASF) may also be used. Examples of alkylphenone compounds include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexylphenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyldimethyl ketal.

[0183] Examples of biimidazole compounds 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, Japanese Patent Publication No. 6-75372, Japanese Patent Publication No. 6-75373, etc.), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, and 2,2'-bis(2-chlorophenyl) Examples include (-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, Japanese Patent Publication No. 48-38403, Japanese Patent Application Publication No. 62-174204, etc.), and biimidazole compounds in which the phenyl group at the 4,4',5,5'-position is substituted with a carboalkoxy group (see, for example, Japanese Patent Application Publication No. 7-10913, etc.).

[0184] Examples of 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-( Examples include 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.

[0185] Examples of acylphosphine oxide compounds include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. Commercially available products such as Irgacure® 819 (manufactured by BASF) may also be used.

[0186] Furthermore, examples of polymerization initiators (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, o-benzoyl methyl benzoate, 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; and 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, and titanocene compounds. These are preferably used in combination with polymerization initiators (D1) (especially amines) as described later.

[0187] The polymerization initiator (D) is preferably a polymerization initiator comprising at least one selected from the group consisting of alkylphenone compounds, triazine compounds, acylphosphine oxide compounds, O-acyloxime compounds, and biimidazole compounds, and more preferably a polymerization initiator comprising an O-acyloxime compound.

[0188] The content of the polymerization initiator (D) is preferably 0.1 parts by mass to 30 parts by mass, and more preferably 1 part by mass to 20 parts by mass, based on 100 parts by mass of the total amount of the total resin (B) and polymerizable compound (C) contained in the colored resin composition. When the content of the polymerization initiator (D) is within the above range, sensitivity tends to increase and exposure time is shortened, thus improving the productivity of color filters.

[0189] <Polymerization initiator (D1)> A polymerization initiator (D1) is a compound or sensitizer used to promote the polymerization of a polymerizable compound (C) whose polymerization has been initiated by a polymerization initiator (D). When a polymerization initiator (D1) is included, it is usually used in combination with the polymerization initiator (D).

[0190] Examples of polymerization initiators (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

[0191] Examples of amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, N,N-dimethylparatoluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michla's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone, with 4,4'-bis(diethylamino)benzophenone being preferred. Alternatively, commercially available amine compounds such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used.

[0192] Examples of alkoxyanthracene compounds 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.

[0193] Examples of thioxanthone compounds include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, and 1-chloro-4-propoxythioxanthone.

[0194] Examples of carboxylic acid compounds 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.

[0195] When these polymerization initiators (D1) are used, their content is preferably 0.1 parts by mass or more and 30 parts by mass or less, and more preferably 1 part by mass or more and 20 parts by mass or less, based on 100 parts by mass of the total amount of the total resin (B) and polymerizable compound (C) contained in the colored resin composition.

[0196] <Solvent (E)> The solvent (E) is not particularly limited, and any solvent commonly used in the art may be used. Examples of solvent (E) include ester solvents (solvents containing -COO- but not -O- in the molecule), ether solvents (solvents containing -O- but not -COO- in the molecule), ether ester solvents (solvents containing both -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- but not -COO- in the molecule), alcohol solvents (solvents containing OH in the molecule but not -O-, -CO-, and -COO- in the molecule), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxides, etc. Two or more of these solvents may be used in combination.

[0197] 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.

[0198] Examples of ether solvents 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, phenethole, and methylanisole.

[0199] 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-methylpropionate, methyl 2-ethoxy-2-methylpropionate Examples 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.

[0200] 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.

[0201] Examples of alcoholic solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

[0202] Examples of aromatic hydrocarbon solvents include benzene, toluene, xylene, and mesitylene.

[0203] Examples of amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

[0204] Preferred solvents (E) include propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, and cyclohexanone.

[0205] When solvent (E) is included, the solvent (E) content is usually 99.99% by mass or less, preferably 40% to 99% by mass, more preferably 50% to 95% by mass, even more preferably 70% to 95% by mass, and even more preferably 75% to 90% by mass, relative to the total amount of the colored resin composition. In other words, the total amount of solids in the colored resin composition is usually 0.01% by mass or more, preferably 1% to 60% by mass, more preferably 5% to 50% by mass, even more preferably 5% to 30% by mass, and even more preferably 10% to 25% by mass. When the solvent (E) content is within the above range, the flatness during coating tends to be good, and the display characteristics tend to be good because there is no shortage of color density when a color filter is formed.

[0206] <Leveling agent (F)> Examples of leveling agents (F) include silicone-based surfactants, fluorine-based surfactants, and silicone-based surfactants containing fluorine atoms. These may have polymerizable groups in their side chains.

[0207] Examples of silicone-based surfactants include surfactants that have siloxane bonds in their molecules. Specifically, examples include Toray Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (product name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324, KP326, KP340, 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).

[0208] Examples of fluorine-based surfactants include surfactants having fluorocarbon chains in their molecules. Specifically, these include Florard® FC430, FC431 (manufactured by Sumitomo 3M Co., Ltd.), Megafac® F142D, F171, F172, F173, F177, F183, F554, R30, RS-718-K (manufactured by DIC Corporation), F-Top® EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Surflon® S381, S382, SC101, SC105 (manufactured by AGC Inc.), and E5844 (manufactured by Daikin Fine Chemical Laboratories, Inc.).

[0209] Examples of silicone-based surfactants containing fluorine atoms include surfactants having siloxane bonds and fluorocarbon chains in their molecules. Specifically, examples include Megafac® R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

[0210] When a leveling agent (F) is included, the content of the leveling agent (F) is preferably 0.0005% by mass or more and 1% by mass or less, more preferably 0.001% by mass or more and 0.5% by mass or less, and even more preferably 0.005% by mass or more and 0.1% by mass or less, relative to 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.

[0211] <Other ingredients> The colored resin composition may optionally contain additives known in the art, such as fillers, other polymer compounds, adhesion promoters, quenchers, antioxidants, light stabilizers, and chain transfer agents.

[0212] <Method for producing colored resin composition> Colored resin compositions can be prepared by mixing a colorant (A), a resin (B), a polymerizable compound (C) used as needed, a polymerization initiator (D), a solvent (E), a leveling agent (F), and other components. Mixing can be carried out using known or conventional equipment and conditions. The coloring agent (A) may be used in a dispersed state after being mixed with part or all of the solvent (E) in advance and dispersed using a bead mill or the like until the average particle size is about 0.2 μm or less. It is preferable to use it in a dispersed state. In this case, part or all of the dispersant and resin (B) may be added as needed. Alternatively, the coloring agent (A) may be used after being dissolved in part or all of the solvent (E) in advance. The desired colored resin composition can be prepared by mixing the remaining components to the coloring agent-containing liquid obtained in this way to a predetermined concentration.

[0213] <How to manufacture color filters> A color filter, which may also be a color conversion layer, can be formed from a colored resin composition. Methods for forming a colored pattern include photolithography, inkjet printing, and printing. Among these, photolithography is preferred. Photolithography is a method in which the colored resin composition is applied to a substrate, dried to form a colored resin composition layer, and then exposed to light through a photomask for development. In photolithography, by not using a photomask during exposure and / or by not developing, a colored coating film, which is a cured product of the colored resin composition layer, can be formed. The colored pattern or colored coating film formed in this way is the color filter of the present invention.

[0214] The film thickness of the color filter to be manufactured is not particularly limited and can be adjusted as appropriate depending on the purpose and application. For example, it is 0.1 μm or more and 30 μm or less, preferably 0.1 μm or more and 20 μm or less, and more preferably 0.5 μm or more and 6 μm or less.

[0215] As substrates, glass plates such as quartz glass, borosilicate glass, aluminasilate glass, and soda-lime glass with a silica coating on the surface are used; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate are used; silicon is used; and aluminum, silver, silver / copper / palladium alloy thin films are formed on the substrate. Other color filter layers, resin layers, transistors, circuits, etc. may be formed on these substrates.

[0216] The formation of each color pixel by photolithography can be carried out using known or conventional equipment and conditions. For example, it can be manufactured as follows. First, a colored resin composition is applied to a substrate, and volatile components such as solvents are removed by heat drying (pre-baking) and / or vacuum drying, and then dried to obtain a smooth colored resin composition layer. Coating methods include spin coating, slit coating, and slit and spin coating. When performing heat drying, the temperature is preferably between 30°C and 120°C, and more preferably between 50°C and 110°C. The heating time is preferably between 10 seconds and 60 minutes, and more preferably between 30 seconds and 30 minutes. When performing vacuum drying, it is preferable to do so under a pressure of 50 Pa to 150 Pa and at a temperature range of 20°C to 25°C. The thickness of the colored resin composition layer is not particularly limited and can be appropriately selected according to the desired thickness of the color filter.

[0217] Next, the colored resin composition layer is exposed via a photomask to form the desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern appropriate to the intended application is used. Furthermore, it is preferable to use an exposure apparatus such as a mask aligner and a stepper, as this allows for uniform irradiation of the entire exposure surface with parallel light rays and precise alignment between the photomask and the substrate on which the colored resin composition layer is formed.

[0218] For exposure, a light source that generates light with a wavelength between 250 nm and 450 nm is preferred. For example, light below 350 nm can be filtered out using a filter that cuts out this wavelength range, or light around 436 nm, 408 nm, and 365 nm can be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specific examples include mercury lamps, light-emitting diodes, metal halide lamps, and halogen lamps.

[0219] A colored pattern is formed on the substrate by developing the colored resin composition layer after exposure by contacting it with a developer. During development, the unexposed parts of the colored resin composition layer are dissolved and removed by the developer. As the developer, aqueous solutions of alkaline compounds such as potassium hydroxide, sodium bicarbonate, sodium carbonate, and tetramethylammonium hydroxide are preferred. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01% by mass or more and 10% by mass or less, and more preferably 0.03% by mass or more and 5% by mass or less. Furthermore, the developer may also contain a surfactant. The development method can be any of the following: paddle method, dipping method, or spray method. Furthermore, the substrate may be tilted to any angle during development. It is preferable to wash the substrate with water after development.

[0220] Furthermore, it is preferable to perform post-baking on the obtained coloring pattern. The post-baking temperature is preferably 150°C to 250°C, and more preferably 160°C to 240°C. The post-baking time is preferably 1 minute to 120 minutes, and more preferably 10 minutes to 60 minutes.

[0221] <Display device> The aforementioned color filter is useful as a color filter for display devices (e.g., liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state image sensors, and is particularly useful as a color filter for organic EL devices. [Examples]

[0222] The present invention will be described in more detail below with reference to examples, but the present invention is not limited by the following examples, and it is certainly possible to implement it with appropriate modifications within the scope that is consistent with the spirit of the preceding and following descriptions, and all such modifications are included within the technical scope of the present invention. In the following, unless otherwise specified, "parts" means "parts by mass" and "%" means "percent mass".

[0223] In the following examples, the structure of the compounds was confirmed by mass spectrometry (LC: Agilent 1200; MASS: Agilent LC / MSD6130).

[0224] The weight-average molecular weight (Mw) and number-average molecular weight (Mn) of the resin, calculated on a polystyrene basis, were measured using the GPC method under the following conditions. Equipment: HLC-8120GPC (manufactured by Tosoh Corporation) Column: TSK-GELG2000HXL Column temperature: 40℃ Solvent: Tetrahydrofuran Flow rate: 1.0mL / min Solid content concentration of the analytical sample: 0.001~0.01% by mass Injection volume: 50μL Detector: RI Calibration standards: 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 to the number-average molecular weight (Mw / Mn) obtained above in polystyrene terms was defined as the degree of dispersion.

[0225] (Synthesis Example 1) 42 parts of acenaphthenequinone (manufactured by Tokyo Chemical Industry Co., Ltd.), 15 parts of malononitrile (manufactured by Tokyo Chemical Industry Co., Ltd.), and 672 parts of dehydrated acetonitrile (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 82°C for 6 hours. When the resulting mixture was cooled to 0°C, an orange-red precipitate was formed. The mixture containing this orange-red precipitate was filtered, and the residue after filtering was washed with 200 parts of acetonitrile and 400 parts of water. The resulting residue was dried under reduced pressure at 60°C to obtain 48 parts of the compound represented by formula (pt2-1) (hereinafter sometimes referred to as compound (pt2-1)) (yield 90%).

[0226] [ka]

[0227] <Identification of compound (pt2-1)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 231 Exact Mass: 230

[0228] (Synthesis Example 2) 25 parts of compound (pt2-1) obtained in Synthesis Example 1, 1.5 parts of potassium carbonate (manufactured by Kanto Chemical Co., Ltd.), 312 parts of acetonitrile (manufactured by Kanto Chemical Co., Ltd.), and 2 parts of water were mixed and stirred at 80°C for 5 hours. When cooled to 0°C, a brown precipitate was formed. The mixture containing this brown precipitate was filtered, and the residue after filtration was washed with 400 parts of water and 50 parts of acetonitrile. The obtained residue was dried under reduced pressure at 60°C and purified using a silica gel column (solvent: chloroform / ethyl acetate = 10 / 1, vol / vol) to obtain 17 parts of the yellowish-brown compound represented by formula (pt3-1) (hereinafter sometimes referred to as compound (pt3-1)) (yield 68%).

[0229] [ka]

[0230] <Identification of compound (pt3-1)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 231 Exact Mass: 230

[0231] (Synthesis Example 3) Three parts of compound (pt3-1) obtained in Synthesis Example 2, one part of 1-butylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), and 21 parts of dehydrated acetonitrile (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 25°C for 4 hours. The reaction mixture was concentrated, and the resulting residue was dried under reduced pressure at 60°C. Purification by neutral alumina column (solvent: gradient from chloroform to acetonitrile) yielded 1.3 parts of a metallic-lustered brown compound represented by formula (I-4) (hereinafter sometimes referred to as compound (I-4)) (yield 33%).

[0232] [ka]

[0233] <Identification of compound (I-4)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 302 Exact Mass: 301

[0234] (Synthesis Example 4) Except for substituting 1.0 part of 1-butylamine with 1.0 part of isobutylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.6 parts of the compound represented by formula (I-40) (hereinafter sometimes referred to as compound (I-40)) were obtained in the same manner as in Synthesis Example 3 (yield 41%).

[0235] [ka]

[0236] <Identification of compound (I-40)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 302 Exact Mass: 301

[0237] (Synthesis Example 5) Except for substituting 1.0 part of 1-butylamine with 1.9 parts of 2-ethylhexylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Synthesis Example 3 was used to obtain 1.7 parts of the compound represented by formula (I-48) (hereinafter sometimes referred to as compound (I-48)) (yield 37%).

[0238] [ka]

[0239] <Identification of compound (I-48)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 358 Exact Mass: 357

[0240] (Synthesis Example 6) Except for substituting 1.0 part of 1-butylamine with 2.9 parts of 1-hexylheptylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.40 parts of the compound represented by formula (I-34) (hereinafter sometimes referred to as compound (I-34)) were obtained in the same manner as in Synthesis Example 3 (yield 7%).

[0241] [ka]

[0242] <Identification of compound (I-34)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 428 Exact Mass: 427

[0243] (Synthesis Example 7) Except for substituting 1.0 part of 1-butylamine with 2.7 parts of 1-dodecylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), the compound represented by formula (I-12) (hereinafter sometimes referred to as compound (I-12)) was obtained in the same manner as in Synthesis Example 3 (yield 19%).

[0244] [ka]

[0245] <Identification of compound (I-12)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 414 Exact Mass: 413

[0246] (Synthesis Example 8) Except for substituting 1.0 part of 1-butylamine with 3.1 parts of 1-tetradecylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.5 parts of the compound represented by formula (I-14) (hereinafter sometimes referred to as compound (I-14)) were obtained in the same manner as in Synthesis Example 3 (yield 26%).

[0247] [ka]

[0248] <Identification of compound (I-14)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 442 Exact Mass: 441

[0249] (Synthesis Example 9) Except for substituting 1.0 part of 1-butylamine with 3.0 parts of 3,3-diphenylpropylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.55 parts of the compound represented by formula (I-112) (hereinafter sometimes referred to as compound (I-112)) were obtained in the same manner as in Synthesis Example 3 (yield 10%).

[0250] [ka]

[0251] <Identification of compound (I-112)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 440 Exact Mass: 439

[0252] (Synthesis Example 10) Except for substituting 1.0 part of 1-butylamine with 1.0 part of 1-hexylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Synthesis Example 3 was used to obtain 0.09 parts of the compound represented by formula (I-6) (hereinafter sometimes referred to as compound (I-6)) (yield 2%).

[0253] [ka]

[0254] <Identification of compound (I-6)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 330 Exact Mass: 329

[0255] (Synthesis Example 11) Except for substituting 1.0 part of 1-butylamine with 1.2 parts of cyclopentylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Synthesis Example 3 was used to obtain 1.3 parts of the compound represented by formula (I-114) (hereinafter sometimes referred to as compound (I-114)) (yield 32%).

[0256] [ka]

[0257] <Identification of compound (I-114)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 314 Exact Mass: 313

[0258] (Synthesis Example 12) Except for substituting 1.0 part of 1-butylamine with 1.4 parts of cyclohexylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Synthesis Example 3 was used to obtain 1.1 parts of the compound represented by formula (I-118) (hereinafter sometimes referred to as compound (I-118)) (yield 26%).

[0259] [ka]

[0260] <Identification of compound (I-118)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 328 Exact Mass: 327

[0261] (Synthesis Example 13) Except for substituting 1.0 part of 1-butylamine with 1.7 parts of 4-methylbenzylamine (Aldrich), the compound represented by formula (I-104) (hereinafter sometimes referred to as compound (I-104)) was obtained in the same manner as in Synthesis Example 3 (yield 29%).

[0262] [ka]

[0263] <Identification of compound (I-104)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 350 Exact Mass: 349

[0264] (Synthesis Example 14) Except for substituting 1.0 part of 1-butylamine with 2.3 parts of 4-(tert-butyl)benzylamine (Aldrich), the same procedure as in Synthesis Example 3 was used to obtain 0.45 parts of the compound represented by formula (I-109) (hereinafter sometimes referred to as compound (I-109)) (yield 9%).

[0265] [ka]

[0266] <Identification of compound (I-109)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 392 Exact Mass: 391

[0267] (Synthesis Example 15) Except for substituting 1.0 part of 1-butylamine with 1.9 parts of ethyl 4-aminobutyrate (manufactured by Tokyo Chemical Industry Co., Ltd.), 1.1 parts of the compound represented by formula (I-80) (hereinafter sometimes referred to as compound (I-80)) were obtained in the same manner as in Synthesis Example 3 (yield 24%).

[0268] [ka]

[0269] <Identification of compound (I-80)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H]+ 360 Exact Mass: 359

[0270] (Synthesis Example 16) Except for substituting 1.0 part of 1-butylamine with 1.8 parts of 1-octylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Synthesis Example 3 was used to obtain 3.3 parts of the compound represented by formula (I-8) (hereinafter sometimes referred to as compound (I-8)) (yield 71%).

[0271] [ka]

[0272] <Identification of compound (I-8)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 358 Exact Mass: 357

[0273] (Synthesis Example 17) Except for substituting 1.0 part of 1-butylamine with 1.9 parts of diisobutylamine (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Synthesis Example 3 was used to obtain 0.08 parts of the compound represented by formula (I-529) (hereinafter sometimes referred to as compound (I-529)) (yield 1.7%).

[0274] [ka]

[0275] <Identification of compound (I-529)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 358 Exact Mass: 357

[0276] (Synthesis Example 18) Except for substituting 1.0 part of 1-butylamine with 1.2 parts of piperidine (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.75 parts of the compound represented by formula (I-713) (hereinafter sometimes referred to as compound (I-713)) were obtained in the same manner as in Synthesis Example 3 (yield 18%).

[0277] [ka]

[0278] <Identification of compound (I-713)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 314 Exact Mass: 313

[0279] (Synthesis Example 19) Except for substituting 1.0 part of 1-butylamine with 1.4 parts of 1-methylpiperazine (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Synthesis Example 3 was used to obtain 0.62 parts of the compound represented by formula (I-721) (hereinafter sometimes referred to as compound (I-721)) (yield 15%).

[0280] [ka]

[0281] <Identification of compound (I-721)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 329 Exact Mass: 328

[0282] (Synthesis Example 20) Except for substituting 1.0 part of 1-butylamine with 2.5 parts of 1-phenylpiperazine (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Synthesis Example 3 was used to obtain 0.62 parts of the compound represented by formula (I-724) (hereinafter sometimes referred to as compound (I-724)) (yield 12%).

[0283] [ka]

[0284] <Identification of compound (I-724)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 391 Exact Mass: 390

[0285] (Synthesis Example 21) Except for substituting 1.0 part of 1-butylamine with 1.5 parts of thiomorpholine (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Synthesis Example 3 was used to obtain 0.92 parts of the compound represented by formula (I-718) (hereinafter sometimes referred to as compound (I-718)) (yield 23%).

[0286] [ka]

[0287] <Identification of compound (I-718)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 332 Exact Mass: 331

[0288] (Synthesis Example 22) Twenty parts of acenaphthenequinone (manufactured by Tokyo Chemical Industry Co., Ltd.) and seventy-eight parts of bromine (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were mixed and stirred under reflux for two hours. The resulting mixture was cooled to 20°C, and 300 parts of 2M sodium sulfite aqueous solution were added, resulting in the formation of a brownish-yellow precipitate. The mixture containing this brownish-yellow precipitate was filtered, and the residue after filtration was washed with 500 parts of water. The resulting residue was dried under reduced pressure at 60°C to obtain 26 parts of the compound represented by formula (pt1-2) (hereinafter sometimes referred to as compound (pt1-2)) (yield 90%).

[0289] [ka]

[0290] <Identification of compounds (pt1-2)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 261 Exact Mass: 260

[0291] (Synthesis Example 23) Except for substituting 42 parts of acenaphthenequinone with 60 parts of compound (pt1-2) obtained in Synthesis Example 22, 41 parts of the compound represented by formula (pt2-2) (hereinafter sometimes referred to as compound (pt2-2)) were obtained in the same manner as in Synthesis Example 1 (yield 58%).

[0292] [ka]

[0293] <Identification of compound (pt2-2)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 309 Exact Mass: 308

[0294] (Synthesis Example 24) Except for replacing 25 parts of compound (pt2-1) with 34 parts of compound (pt2-2) obtained in Synthesis Example 23, 17 parts of the compound represented by formula (pt3-2) (hereinafter sometimes referred to as compound (pt3-2)) were obtained in the same manner as in Synthesis Example 2 (yield 50%).

[0295] [ka]

[0296] <Identification of compound (pt3-2)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 309 Exact Mass: 308

[0297] (Synthesis Example 25) 18 parts of compound (pt3-2) obtained in Synthesis Example 24, 12 parts of aniline (manufactured by Tokyo Chemical Industry Co., Ltd.), 0.65 parts of palladium acetate (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.0 parts of 2-dicyclohexylphosphino-2',6'-dimethoxybiphenyl (manufactured by Tokyo Chemical Industry Co., Ltd.), 28 parts of tert-butoxysodium (manufactured by Tokyo Chemical Industry Co., Ltd.), and 396 parts of dehydrated ethylene glycol dimethyl ether (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 70°C for 6 hours. After filtering the reaction mixture through Celite, the filtrate was concentrated, and the resulting residue was dried under reduced pressure at 60°C. Purification by neutral alumina column (solvent: gradient from chloroform to acetonitrile) yielded 11 parts of a metallic-lustered brown compound represented by formula (I-95) (hereinafter sometimes referred to as compound (I-95)) (yield 59%).

[0298] [ka]

[0299] <Identification of compound (I-95)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 322 Exact Mass: 321

[0300] (Synthesis Example 26) Except for substituting 12 parts of aniline with 16 parts of N-ethylaniline (manufactured by Tokyo Chemical Industry Co., Ltd.), 14 parts of the compound represented by formula (I-421) (hereinafter sometimes referred to as compound (I-421)) were obtained in the same manner as in Synthesis Example 25 (yield 70%).

[0301] [ka]

[0302] <Identification of compound (I-421)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 350 Exact Mass: 349

[0303] (Example 1) Ten parts of compound (pt3-1) obtained in Synthesis Example 2, 4.5 parts of methanesulfonamide (manufactured by Tokyo Chemical Industry Co., Ltd.), 5.6 parts of N,N,N',N'-tetramethylethylenediamine (manufactured by Tokyo Chemical Industry Co., Ltd.), and 21 parts of dehydrated acetonitrile (manufactured by Kanto Chemical Co., Ltd.) were mixed and stirred at 35°C for 18 hours. The reaction mixture was concentrated, and the resulting residue was dried under reduced pressure at 60°C. Purification by a neutral alumina column (solvent: gradient from chloroform to acetonitrile) yielded 3.0 parts of the compound represented by the blue-violet formula (I-126) (hereinafter sometimes referred to as compound (I-126)) (yield 21%).

[0304] [ka]

[0305] <Identification of compound (I-126)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 324 Exact Mass: 323

[0306] (Example 2) Except for substituting 4.5 parts of methanesulfonamide with 7.5 parts of phenylsulfonamide (manufactured by Tokyo Chemical Industry Co., Ltd.), 3.1 parts of the compound represented by formula (I-144) (hereinafter sometimes referred to as compound (I-144)) were obtained in the same manner as in Example 1 (yield 19%).

[0307] [ka]

[0308] <Identification of compound (I-144)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 386 Exact Mass: 385

[0309] (Example 3) Except for substituting 4.5 parts of methanesulfonamide with 7.1 parts of trifluoromethylsulfonamide (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Example 1 was used to obtain 1.4 parts of the compound represented by formula (I-656) (hereinafter sometimes referred to as compound (I-656)) (yield 9%).

[0310] [ka]

[0311] <Identification of compound (I-656)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 378 Exact Mass: 377

[0312] (Example 4) Except for substituting 4.5 parts of methanesulfonamide with 7.1 parts of tert-butylsulfonamide (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Example 1 was used to obtain 2.2 parts of the compound represented by formula (I-653) (hereinafter sometimes referred to as compound (I-653)) (yield 14%).

[0313] [ka]

[0314] <Identification of compound (I-653)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 366 Exact Mass: 365

[0315] (Example 5) Except for substituting 4.5 parts of methanesulfonamide with 8.2 parts of benzylsulfonamide (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Example 1 was used to obtain 2.4 parts of the compound represented by formula (I-150) (hereinafter sometimes referred to as compound (I-150)) (yield 14%).

[0316] [ka]

[0317] <Identification of compound (I-150)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 400 Exact Mass: 399

[0318] (Example 6) Except for substituting 4.5 parts of methanesulfonamide with 8.4 parts of 4-fluorophenylsulfonamide (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Example 1 was used to obtain 0.90 parts of the compound represented by formula (I-659) (hereinafter sometimes referred to as compound (I-659)) (yield 5%).

[0319] [ka]

[0320] <Identification of compound (I-659)> (Mass Spectrometry) Ionization Mode = ESI+: m / z = [M+H] + 404 Exact Mass: 403

[0321] (Synthesis Example 27) The compound represented by the following formula (x) (hereinafter sometimes referred to as compound (x)) was synthesized in accordance with the description in Synthesis Example 2 of Japanese Patent Publication No. 2020-079397.

[0322] [ka]

[0323] (Synthesis Example 28) A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, dropping funnel, and stirrer to replace the atmosphere with nitrogen. 280 parts of propylene glycol monomethyl ether acetate were added, and the mixture was heated to 80°C while stirring. Then, 38 parts of acrylic acid and 3,4-epoxytricyclo[5.2.1.02,6 ] Decane-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 2,6 A mixture of 289 parts of decane-9-yl acrylate (with a molar ratio of 1:1) 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 the addition was complete, the mixture was held at 80°C for 4 hours, 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 B-type viscometer (23°C). The weight-average molecular weight Mw of the resulting copolymer was 9.2 × 10⁻⁶. 3 The dispersion was 2.08, and the acid value on a solid content basis was 77 mg-KOH / g. Resin B1 has the following structural units.

[0324] [ka]

[0325] <Example 7> (1) Preparation of coloring composition The following components were mixed to obtain colored composition 1. (A) Coloring agent: Compound (I-4) 2.6 parts (B) Resin: 54 parts of resin B1 solution (E) Solvent: Propylene glycol monomethyl ether acetate 420 parts (2) Preparation of colored resin composition Next, the following components were mixed to obtain colored resin composition 1. Coloring composition 1 478 parts (C) Polymerizable compound: Dipentaerythritol hexaacrylate (Kayalad® DPHA; manufactured by Nippon Kayaku Co., Ltd.) 40 copies (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure® 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

[0326] (3) Preparation of colored coating film (color filter) A colored resin composition was applied to a 5cm square glass substrate (Eagle XG; Corning Corporation) by spin coating to a post-baking thickness of 2μm. The substrate was then pre-baked at 100°C for 3 minutes to form a colored resin composition layer. After cooling, the colored resin composition layer formed on the substrate was exposed to air at 80mJ / cm² using an exposure unit (TME-150RSK; Topcon Corporation) in an atmospheric environment. 2 The sample was irradiated with light at the specified exposure level (based on 365 nm). After light irradiation, post-baking was performed in an oven at 230°C for 30 minutes to obtain a colored coating. The film thickness of the colored coating was measured using DEKTAK3 (manufactured by Nippon Vacuum Technology Co., Ltd.). The results are shown in Table 11.

[0327] (4) Contrast evaluation The contrast of the obtained colored coatings was measured using a contrast meter (CT-1: manufactured by Tsubosaka Electric Co., Ltd., color difference meter BM-5A: manufactured by Topcon Corporation, light source: F-10, polarizing film: manufactured by Tsubosaka Electric Co., Ltd.). The blank value during measurement was 30,000. If the contrast of the colored coating is good, it can be said that the colored pattern made from the same colored resin composition will also have good contrast. The results are shown in Table 11.

[0328] <Examples 8-22, Comparative Example 1> A colored composition and a colored resin composition were prepared in the same manner as in Example 7, except that compound (I-4) from Example 7 was replaced with a compound listed in Table 11. A colored coating film was then prepared and its contrast was evaluated. The results are shown in Table 11.

[0329] Except for substituting compound (I-4) of Example 7 with compound (I-529), compound (I-713), compound (I-721), compound (I-724), compound (I-718), compound (I-95), compound (I-421), compound (I-656), compound (I-653), compound (I-150), or compound (I-659), a colored composition and a colored resin composition were prepared in the same manner as in Example 7, and a colored coating film was prepared. When the contrast was evaluated, it showed good contrast.

[0330] [Table 11]

Claims

1. A colored resin composition containing a coloring agent and a resin, wherein the coloring agent comprises a compound represented by formula (I). 【Chemistry 1】 [In formula (I), R 1 and R 2 These are, independently of each other, hydrogen atoms, -R 8a , or -SO 2 -R 8b It represents. R 1 and R 2 each together with the nitrogen atom to which it is attached may form a ring which may have substituents, and the -CH 2 - in the ring may be replaced by -O-, -CO-, -S-, -S(O) 2 -, -NH-, or -NR 8g -. R 3 ~R 7 These are, independently of each other, hydrogen atoms, -R 8c , -O-R 8d , -CO-O-R 8e , -O-CO-R 8f This represents a halogen atom, a hydroxyl group, a carboxyl group, a sulfo group, or a nitro group. R 8a , R 8b , R 8c , R 8d , R 8e , R 8f , and R 8g Each of these independently represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. R 8a , R 8b , R 8c , R 8d , R 8e , R 8f , and R 8g If multiple instances exist, they may be identical or different.

2. R in equation (I) 1 ga-SO 2 -R 8b and R 2 is a hydrogen atom, or -R 8a The colored resin composition according to claim 1.

3. The colored resin composition according to claim 1 or 2, further comprising a polymerizable compound and a polymerization initiator.

4. A color filter formed from a colored resin composition according to any one of claims 1 to 3.

5. A display device comprising the color filter described in claim 4.

6. A compound represented by formula (IA). 【Chemistry 2】 [In formula (IA), R 11 This represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. R 2 This is a hydrogen atom, -R 8a , or -SO 2 -R 8b It represents. R 3 ~R 7 These are, independently of each other, hydrogen atoms, -R 8c , -O-R 8d , -CO-O-R 8e , -O-CO-R 8f This represents a halogen atom, a hydroxyl group, a carboxyl group, a sulfo group, or a nitro group. R 8a , R 8b , R 8c , R 8d , R 8e , and R 8f Each of these independently represents a hydrocarbon group having 1 to 20 carbon atoms, which may have substituents. R 8c , R 8d , R 8e , and R 8f If multiple instances exist, they may be identical or different.

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