JP7807909B2 - Colored resin composition, color filter, and display device - Google Patents

Description

The present invention relates to a colored resin composition, a color filter, and a display device.

Color filters used in displays such as liquid crystal displays, electroluminescent displays, and plasma displays, as well as solid-state imaging devices such as CCD and CMOS sensors, are manufactured from colored resin compositions. Perylene tetracarboxylic diimide compounds are known as colorants contained in such colored resin compositions (Patent Document 1).

Japanese Patent Application Laid-Open No. 2020-079397

However, color filters formed from conventional colored resin compositions that use the above-mentioned perylene tetracarboxylic acid diimide compounds as colorants have sometimes failed to provide fully satisfactory contrast. Therefore, an object of the present invention is to provide a colored resin composition that can be used to form color filters that exhibit good contrast.

The gist of the present invention is as follows.
[1] A colored resin composition containing a colorant and a resin, wherein the colorant contains a compound represented by formula (I).

[In formula (I),
R ¹ to R ³ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
^R2 and ^R3 may be joined together with the nitrogen atom to which they are bonded to form a ring which may have a substituent.
R ⁴ to R ⁸ each independently represent a hydrogen atom, —R ⁹ , —O—R ⁹ , —CO—O—R ⁹ , —O—CO—R ⁹ , a halogen atom, a hydroxy group, a carboxy group, a sulfo group, or a nitro group.
R ⁹ represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and when there are multiple R ^9s , they may be the same or different.
[2] The colored resin composition according to [1], further comprising a polymerizable compound and a polymerization initiator.
[3] A color filter formed from the colored resin composition according to [1] or [2].
[4] A display device comprising the color filter according to [3].

The present invention provides a colored resin composition that can be used to form a color filter that exhibits good contrast.

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

<Colorant (A)>
The colorant (A) contains a compound represented by formula (I) (hereinafter, may be referred to as compound (I)). Since the colorant (A) contains compound (I), the colored resin composition of the present invention can form a color filter that exhibits good contrast, and preferably can form a color filter that is also excellent in heat resistance and light resistance.

<<Compound (I)>>

[In formula (I),
R ¹ to R ³ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
^R2 and ^R3 may be joined together with the nitrogen atom to which they are bonded to form a ring which may have a substituent.
R ⁴ to R ⁸ each independently represent a hydrogen atom, —R ⁹ , —O—R ⁹ , —CO—O—R ⁹ , —O—CO—R ⁹ , a halogen atom, a hydroxy group, a carboxy group, a sulfo group, or a nitro group.
R ⁹ represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and when there are multiple R ^9s , they may be the same or different.

The hydrocarbon groups having 1 to 20 carbon atoms represented by R ¹ to R ³ and R ⁹ include aliphatic hydrocarbon groups and aromatic hydrocarbon groups. The aliphatic hydrocarbon groups may be saturated or unsaturated, and may be linear or alicyclic.

Examples of the saturated or unsaturated chain hydrocarbon group represented by R ¹ to R ³ and R ⁹ include linear alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, and icosyl groups; isopropyl, (1-ethyl)propyl, isobutyl, sec-butyl, tert-butyl, (3-methyl)butyl, (1-methyl)butyl, (1-ethyl)butyl, (2-methyl)butyl, (2-ethyl)butyl, and (1-propyl)butyl. a methyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a (2-methyl)pentyl group, a (3-methyl)pentyl group, a (1-ethyl)pentyl group, a (2-ethyl)pentyl group, a (3-ethyl)pentyl group, a (1-propyl)pentyl group, a (1-butyl)pentyl group, a (2-propyl)pentyl group, an isohexyl group, a (2-methyl)hexyl group, a (5-methyl)hexyl group, a (1-ethyl)hexyl group, a (2-ethyl)hexyl group, a (1-propyl)hexyl group, a (2-propyl)hexyl group, a (1-butyl)hexyl group, a (2-butyl)hexyl group, a (1-pentyl)hexyl group, a (2-methyl)heptyl group, a (2 (1-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-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, branched alkyl groups such as a (1-hexyl)nonyl group, a (2-hexyl)nonyl group, a (1-heptyl)nonyl group, a (1-octyl)nonyl group, a (2-propyl)decyl group, a (2-butyl)decyl group, a (2-pentyl)decyl group, a (2-hexyl)decyl group, a (1-heptyl)decyl group, and a (2-butyl)undecyl group; and alkenyl groups such as a vinyl group, a 1-propenyl group, a 2-propenyl group (allyl group), a (1-methyl)ethenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1,3-butadienyl group, a (1-(2-propenyl))ethenyl group, a (1,2-dimethyl)propenyl group, and a 2-pentenyl group. The number of carbon atoms in the saturated chain hydrocarbon group is preferably 1 to 18, more preferably 1 to 16, and even more preferably 1 to 15. The number of carbon atoms in the unsaturated chain hydrocarbon group is preferably 2 to 18, more preferably 2 to 16, and even more preferably 2 to 15.

Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by R ¹ to R ³ and R ⁹ include cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl; cycloalkenyl groups such as cyclohexenyl (for example, cyclohex-2-ene and cyclohex-3-ene), cycloheptenyl, and cyclooctenyl; norbornyl, adamantyl, and bicyclo[2.2.2]octyl. The saturated or unsaturated alicyclic hydrocarbon group preferably has 3 to 18 carbon atoms, more preferably 3 to 16, and even more preferably 3 to 15.

Examples of the aromatic hydrocarbon group represented by R ¹ to R ³ and R ⁹ include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a phenanthryl group, an anthryl group, a pyrenyl group, etc. The aromatic hydrocarbon group preferably has 6 to 20 carbon atoms, more preferably 6 to 18 carbon atoms, and even more preferably 6 to 15 carbon atoms.

The hydrocarbon groups represented by R ¹ to R ³ and R ⁹ may be groups in which two or more of the chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups listed above are combined, as long as the upper limit of the number of carbon atoms is 20 or less.
Such a group may be, for example, a group obtained by combining an aromatic hydrocarbon group with at least one group selected from a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group, and in such a hydrocarbon group obtained by combining the chain hydrocarbon group, the chain hydrocarbon group may be combined as a divalent group (for example, an alkanediyl group). Examples of combined hydrocarbon groups include aralkyl groups such as benzyl, phenethyl, 1-methyl-1-phenylethyl, 1-naphthylmethyl, 2-naphthylmethyl, diphenylmethyl, 2,2-diphenylethyl, 3,3-diphenylpropyl, and 4,4-diphenylbutyl; arylalkenyl groups such as phenylethenyl (phenylvinyl); arylalkynyl groups such as phenylethynyl; o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2,4,6-trimethylphenyl, 4-vinylphenyl, and o-isopropyl. propylphenyl group, m-isopropylphenyl 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-dodecyl alkylaryl groups such as a phenyl group and a 4-dodecylphenyl group; an o-tolylmethyl group, an m-tolylmethyl group, a p-tolylmethyl group, a 2-ethylphenylmethyl group, a 3-ethylphenylmethyl group, a 4-ethylphenylmethyl group, a 2,3-dimethylphenylmethyl group, a 2,4-dimethylphenylmethyl group, a 2,5-dimethylphenylmethyl group, a 2,6-dimethylphenylmethyl group, a 3,4-dimethylphenylmethyl group, a 3,5-dimethylphenylmethyl group, a 2,4,6-trimethylphenylmethyl group, a 4-vinylphenylmethyl group, an o-isopropylphenylmethyl group, an m-isopropylphenylmethyl group, a p-isopropylphenylmethyl group, a 2,3-diisopropylphenylmethyl group, a 2,4-diisopropylphenylmethyl group, a 2,5-diisopropylphenylmethyl group, a 2,6-diisopropylphenylmethyl group, alkylarylalkyl groups such as a 2,3-dihydro-4-indenyl group, a 1,2,3,5,6,7-hexahydro-4-s-indacenyl group, a 8-methyl-1,2,3,5,6,7-hexahydro-4-s-indacenyl group, a 5,6,7,8-tetrahydro-1-naphthyl group, a 5,6,7,8-tetrahydro-2-naphthyl group, a 3-methyl-5,6,7,8-tetrahydro-2-naphthyl group, and a 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl group; aryl groups such as a biphenylyl group and a terphenylyl group having one or more aryl groups bonded thereto; a cyclohexylmethylphenyl group, a benzylphenyl group, and a (dimethyl(phenyl)methyl)phenyl group.
The hydrocarbon group may be, for example, a hydrocarbon group formed by combining a chain hydrocarbon group with an alicyclic hydrocarbon group, and examples thereof include a 1-methylcyclopropyl group, a 2-methylcyclopentyl group, a 3-methylcyclopentyl group, a 1-methylcyclohexyl group, a 2-methylcyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 1,2-dimethylcyclohexyl group, a 1,3-dimethylcyclohexyl group, a 1,4-dimethylcyclohexyl group, a 2-methylcyclopent ...2-methylcyclopentyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 1,4-dimethylcyclohexyl group, a 2-methylcyclopentyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 1,2-dimethylcyclohexyl group, a 1,3-dimethylcyclohexyl group, a 2-methylcyclopentyl group, a 3-methylcyclohexyl group, a 4-methylcyclohex cyclohexyl 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 cyclohexyl group, 3,3,5,5-tetramethylcyclohexyl group, 4-pentylcyclohexyl group, 4-octylcyclohexyl group, 4-cyclohexylcyclohexyl group, etc.; alkyl group having one or more alicyclic hydrocarbon groups bonded thereto such as cyclopropylmethyl group, cyclopropylethyl group, cyclobutylmethyl group, cyclobutylethyl group, cyclopentylmethyl group, cyclopentylethyl group, cyclohexylmethyl group, cyclohexylethyl group, adamantylmethyl group, etc.; alkyl group having one or more alicyclic hydrocarbon groups bonded thereto such as 2-methylcyclopropylmethyl group, 2-methylcyclobutylmethyl group, 3-methylcyclobutylmethyl group, 2-methylcyclopentylmethyl group, 3-methylcyclopentylmethyl group, 2-methylcyclohexylmethyl group, 3-methylcyclohexylmethyl group, 4-methylcyclohexylmethyl group, etc.
The number of carbon atoms in the group formed by combining two or more chain 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.

Examples of —O—R ⁹ include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a nonyloxy group, a decyloxy group, a (2-ethyl)hexyloxy group, an icosyloxy group, a 1-phenylethoxy group, a 1-methyl-1-phenylethoxy group, a phenyloxy group, a 2,3-dimethylphenyloxy group, a 2,4-dimethylphenyloxy group, a 2,5-dimethylphenyloxy group, a 2,6-dimethylphenyloxy group, a 3,4-dimethylphenyloxy group, and a 3,5-dimethylphenyloxy group.

Examples of —CO—O—R ⁹ include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, a hexyloxycarbonyl group, a (2-ethyl)hexyloxycarbonyl group, a heptyloxycarbonyl group, an octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, a phenyloxycarbonyl group, and an icosyloxycarbonyl group.

Examples of —O—CO—R ⁹ include an acetoxy group, a propanoyloxy group, a butanoyloxy group, a 2,2-dimethylpropanoyloxy group, a pentanoyloxy group, a hexanoyloxy group, a (2-ethyl)hexanoyloxy group, a heptanoyloxy group, an octanoyloxy group, a nonanoyloxy group, a decanoyloxy group, and a benzoyloxy group.

Examples of substituents that the hydrocarbon group having 1 to 20 carbon atoms represented by R ¹ to R ³ and R ⁹ may have include: a halogen atom; a group 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 of -O- or -CO- is included); a nitrile group; a nitro group; an amino group; an amido group; a sulfonamido group; a hydroxy group; a thiol group; an alkylthio group having 1 to 15 carbon atoms, such as a methylthio group or an ethylthio group; an allylthio group; an arylthio group having 6 to 20 carbon atoms, such as a phenylthio group, a 1-naphthylthio group, or a 2-naphthylthio group; a sulfoxy group; an alkylsulfoxy group having 1 to 15 carbon atoms, such as a methylsulfoxy group or an ethylsulfoxy group; arylsulfoxy groups having 6 to 20 carbon atoms such as an oxy group, a 1-naphthylsulfoxy group, or a 2-naphthylsulfoxy group; a silyl group; a boryl group; alkylamino groups having 1 to 15 carbon atoms such as a monomethylamino group, a dimethylamino group, a monoethylamino group, or a diethylamino group; arylamino groups having 6 to 20 carbon atoms such as a monophenylamino group or a diphenylamino group; aralkylamino groups having 7 to 20 carbon atoms such as a benzylamino group; alkylaminosulfonyl groups having 1 to 15 carbon atoms such as an N-methylaminosulfonyl group, an N,N-dimethylaminosulfonyl group, or an N-ethylaminosulfonyl group; a carboxy group; a carbamoyl group; and heterocyclic groups having 1 to 20 carbon atoms such as a furyl group, a pyrrolyl group, or a thienyl group.

Examples of the group combining at least one selected from the group consisting of -O-, -CO-, and divalent hydrocarbon groups (including at least one -O- or -CO-) with a monovalent hydrocarbon group include groups represented by the following formulas (Sa) and (Sb).

[In formula (Sa), formula (Sb),
R ^S represents a hydrocarbon group having 1 to 20 carbon atoms, and the methylene groups contained in the hydrocarbon group may be replaced with —O— and/or —CO—.
* represents a bond.

Examples of the hydrocarbon group having 1 to 20 carbon atoms represented by R ^S include the same examples as those of the hydrocarbon groups represented by R ¹ to R ³ and R ⁹ above.
When a methylene group contained in the hydrocarbon group represented by R ^S is replaced with -O- and/or -CO-, the number of such groups may be 1 or 2 or more. When a methylene group contained in the hydrocarbon group is replaced with -O- and/or -CO-, the number of carbon atoms before replacement is defined as the number of carbon atoms in the hydrocarbon group.

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

When the hydrocarbon groups represented by R ¹ to R ³ and R ⁹ have substituents, the number of the substituents may be one or two or more, and the two or more substituents may be independently the same or different.

Halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms.

R ¹ is preferably a methyl group, an ethyl group, or a hydrogen atom, more preferably an ethyl group or a hydrogen atom, and even more preferably a hydrogen atom.

The hydrocarbon group having 1 to 20 carbon atoms represented by ^R2 and ^R3 is preferably a saturated chain hydrocarbon group, a saturated alicyclic hydrocarbon group, a group in which an aromatic hydrocarbon group and a chain hydrocarbon group are combined, or a group in which a chain hydrocarbon group and an alicyclic hydrocarbon group are combined; more preferably a saturated chain hydrocarbon group, a saturated alicyclic hydrocarbon group, or a group in which an aromatic hydrocarbon group and a chain hydrocarbon group are combined; even more preferably a saturated chain hydrocarbon group or a group in which an aromatic hydrocarbon group and a chain hydrocarbon group are combined; still more preferably a saturated chain hydrocarbon group, a saturated chain hydrocarbon group having 2 to 15 carbon atoms, even more preferably a saturated chain hydrocarbon group having 4 to 12 carbon atoms, and even more preferably a saturated chain hydrocarbon group having 4 to 10 carbon atoms.
The hydrocarbon groups represented by ^R2 and ^R3 may have a substituent, but preferably do not have a substituent.

The hydrocarbon group having 1 to 20 carbon atoms which may have a substituent represented by ^R2 and ^R3 is specifically preferably a group represented by the following formulae (D-1) to (D-69) and (G-1) to (G-31), more preferably a group represented by formulae (D-1) to (D-69) and (G-1) to (G-19), still more preferably a group represented by formulae (D-1) to (D-69), still more preferably a group represented by formulae (D-1) to (D-18) and (D-40) to (D-52), still more preferably a group represented by formulae (D-1) to (D-18), and still more preferably a group represented by formulae (D-2) to (D-15). In the formulae, * represents a bond.

The ring formed by ^R2 and ^R3 together with the nitrogen atom to which they are bonded may be saturated or unsaturated, and may be monocyclic or polycyclic.

The number of members in the ring formed by ^R2 and ^R3 together with the nitrogen atom to which they are bonded is preferably 3 to 15, more preferably 4 to 12, even more preferably 5 to 10, and still more preferably 5 to 7.

Examples of the ring formed by ^R2 and ^R3 together with the nitrogen atom to which they are bonded include a pyrrolidine ring, a morpholine ring, a piperidine ring, and a piperazine ring, and rings having only one nitrogen atom as a heteroatom, such as a pyrrolidine ring and a piperidine ring, are preferred.

Specific examples of the ring formed by ^R2 and ^R3 together with the nitrogen atom to which they are bonded include rings represented by the following formulae (J-1) to (J-9), in which * represents a bond.

The ring formed by ^R2 and ^R3 together with the nitrogen atom to which they are bonded is preferably a ring represented by the above formula (J-1) to formula (J-9), more preferably a ring represented by formula (J-1) to formula (J-7), still more preferably a ring represented by formula (J-1) to formula (J-6), and still more preferably a ring represented by formula (J-3) to formula (J-5).

Examples of the substituent that may be possessed by the ring formed ^{by R2} and ^R3 together with the nitrogen atom to which they are bonded include the same examples as the substituent that may be possessed by the hydrocarbon group having 1 to 20 carbon atoms represented by ^R1 to ^R3 and ^R9 . When the ring formed by ^R2 and ^R3 together with the nitrogen atom to which they are bonded has a substituent, the number of the substituent may be one or two or more, and the two or more substituents may be independently the same or different.

It is particularly preferred that one of ^R2 and ^R3 is a hydrogen atom and the other is a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.

R ⁴ to R ⁸ are preferably a hydrogen atom or —R ⁹ , and more preferably a hydrogen atom.
R ⁹ is preferably a saturated chain hydrocarbon group which may have a substituent, and more preferably a saturated chain hydrocarbon group having 1 to 10 carbon atoms.

Examples of compound (I) include compounds represented by the following formula (Ii) in which the combination of R ¹ , R ² and R ³ is any of those shown in Tables 1 to 4 below, and compounds represented by the following formula (Iii) in which the combination of R ²³ (the ring formed by R ² and R ³ in formula (I) together with the nitrogen atom to which they are bonded) and R ¹ is any of those shown in Table 5 below. In Tables 1 to 5, H represents a hydrogen atom, Et represents an ethyl group, IBu represents an isobutyl group, D-1 to D-15, D-19 to D-34, D-40 to D-67, G-1 to G-6, G-9 to G-14, and G-20 to G-27 represent groups represented by the above formulas (D-1) to (D-15), (D-19) to (D-34), (D-40) to (D-67), (G-1) to (G-6), (G-9) to (G-14), and (G-20) to (G-27), respectively, and J-1 to J-9 represent rings represented by the above formulas (J-1) to (J-9).

[In formula (III), ^R23 represents a ring formed by ^R2 and ^R3 together with the nitrogen atom to which they are bonded.]

As compound (I), compounds (Ii-1) to (Ii-15) are preferred, and compounds (Ii-2) to (Ii-15) are more preferred.

Compound (I) may be:
Compounds (Ii-1) to (Ii-334) are preferred,
Compound (Ii-1) to compound (Ii-237) and compound (Ii-317) to compound (Ii-334) are more preferable,
Compounds (Ii-1) to (Ii-15), compounds (Ii-32) to (Ii-71), compounds (Ii-80) to (Ii-94), compounds (Ii-111) to (Ii-150), compounds (Ii-159) to (Ii-173), compounds (Ii-190) to (Ii-229), compounds (Ii-318) to (Ii-322), and compounds (Ii-327) to (Ii-331) are more preferred,
Compound (Ii-2) to compound (Ii-14), compound (Ii-32) to compound (Ii-44), compound (Ii-60) to compound (Ii-71), compound (Ii-81) to compound (Ii-93), compound (Ii-111) to compound (Ii-123), compound (Ii-139) to compound (Ii-150), compound (Ii-160) to compound (Ii-172), compound (Ii-190) to compound (Ii-202), compound (Ii-319) to compound (Ii-321), and compound (Ii-328) to compound (Ii-330) are even more preferred.

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)); by subjecting compound (pt2) to a condensation reaction in a solvent using a catalyst to produce a compound represented by the following formula (pt3) (hereinafter sometimes referred to as compound (pt3)); by treating compound (pt3) with concentrated sulfuric acid to produce a compound represented by the following formula (pt4) (hereinafter sometimes referred to as compound (pt4)); by reacting compound (pt4) with a compound represented by the following formula (MA1) (hereinafter sometimes referred to as compound (MA1)) in a solvent to produce a compound represented by the following formula (pt5) (hereinafter sometimes referred to as compound (pt5)); and by further reacting compound (pt5) with a compound represented by the following formula (MA2) (hereinafter sometimes referred to as compound (MA2)) in a solvent.

[In the formula, R ¹ to R ⁸ are the same as defined above. R ^A represents a hydrogen atom or a halogen atom, and R ^B represents a halogen atom or a p-toluenesulfonyl group.]

Examples of compound (pt1) include acenaphthenequinone.

Examples of the halogen atom represented by R ^A include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. ^{R A} is preferably a hydrogen atom.

The amount of malononitrile used is typically 0.1 mol or more and 500 mol or less, preferably 0.3 mol or more and 400 mol or less, more preferably 0.5 mol or more and 300 mol or less, and even more preferably 0.8 mol or more and 200 mol or less, per 1 mol of compound (pt1).

As a solvent for the reaction of compound (pt1) with malononitrile, it is preferable to use a solvent (especially an organic solvent) that has been thoroughly deoxidized and/or dehydrated in order to suppress side reactions, and dehydrated acetonitrile is more preferred.

The amount of solvent used in the reaction of compound (pt1) with malononitrile is typically 0.1 to 1,000 parts by mass per part by mass of compound (pt1).

The reaction temperature when reacting compound (pt1) with malononitrile is typically -100°C or higher and 300°C or lower. The reaction time when reacting compound (pt1) with malononitrile is typically 0.5 hours to 300 hours.

Examples of compound (pt2) include 2-(2-oxo-2H-acenaphthylene-1-ylidene)-malononitrile.

Catalysts used in the production of compound (pt3) include palladium compounds such as tris(dibenzylideneacetone)dipalladium(0), bis(dibenzylideneacetone)palladium(0), palladium(II) acetate, palladium(II) chloride, sodium tetrachloropalladium(II), 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-diisopropyl ether. Examples of suitable bases 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. Preferred are cesium carbonate, potassium carbonate, potassium phosphate, triethylamine, 4-(N,N-dimethylamino)pyridine, N,N-diisopropylethylamine, and 1,4-diazabicyclo[2.2.2]octane.

The amount of catalyst used may be any catalytic amount, for example, 0.1 to 50 moles, preferably 0.5 to 40 moles, and more preferably 1.0 to 30 moles, per 100 moles of compound (pt2).

Solvents used in the condensation reaction of compound (pt2) in the presence of a catalyst include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; ether solvents such as diethyl ether and tetrahydrofuran; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1,2-dichlorobenzene; amide solvents such as N,N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid; and imidazole. Water and nitrile solvents are preferred, and water and acetonitrile are more preferred.

The amount of solvent used in the condensation reaction of compound (pt2) in the presence of a catalyst is typically 0.1 to 1,000 parts by mass per part by mass of compound (pt2).

The reaction temperature for the condensation reaction of compound (pt2) in the presence of a catalyst is typically -100°C or higher and 300°C or lower. The reaction time for the condensation reaction of compound (pt2) in the presence of a catalyst is typically 0.5 hours to 300 hours.

Examples of compound (pt3) include 1-oxo-1H-phenalene-2,3-dicarbonitrile.

The reaction temperature when compound (pt3) is treated with concentrated sulfuric acid is typically 0°C or higher and 300°C or lower. The reaction time when compound (pt3) is treated with concentrated sulfuric acid is typically 0.5 hours to 300 hours.

Examples of compound (pt4) include 1-oxo-1H-phenalene-2,3-dicarboximide.

Examples of compound (MA1) include alkyl halides (specifically, ethyl iodide, etc.), alkyl tosylates, etc.

The amount of compound (MA1) used is typically 0.4 mol or more and 20 mol or less, preferably 0.5 mol or more and 15 mol or less, and more preferably 0.6 mol or more and 10 mol or less, per 1 mol of compound (pt4).

Solvents for the reaction of compound (pt4) with compound (MA1) include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; ether solvents such as diethyl ether and tetrahydrofuran; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1,2-dichlorobenzene; amide solvents such as N,N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid; and imidazole. Water and nitrile solvents are preferred, and water and acetonitrile are more preferred.

The amount of solvent used in the reaction between compound (pt4) and compound (MA1) is typically 0.1 to 1,000 parts by mass per part by mass of compound (pt4).

The reaction between compound (pt4) and compound (MA1) may be carried out in the presence of an alkali to neutralize the hydrogen halide or tosylic acid generated by the reaction. Examples of such alkali include sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, and triethylamine.

When an alkali is used in the reaction of compound (pt4) with compound (MA1), the amount of the alkali used is typically 0.1 mol or more and 50 mol or less, and preferably 0.5 mol or more and 30 mol or less, per 1 mol of compound (pt4).

Examples of compound (pt5) include N-ethyl-1-oxo-1H-phenalene-2,3-dicarboximide.

Examples of compound (MA2) include 1-hexylamine, n-butylamine, benzylamine, diisobutylamine, and piperidine.

The amount of compound (MA2) used is typically 0.05 mol or more and 20 mol or less, preferably 0.1 mol or more and 15 mol or less, and more preferably 0.2 mol or more and 10 mol or less, per 1 mol of compound (pt5).

Solvents for use in the reaction of compound (pt5) with compound (MA2) include water; nitrile solvents such as acetonitrile; alcohol solvents such as methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 1-pentanol, 1-hexanol, 1-heptanol, 2-ethyl-1-hexanol, 1-octanol, and phenol; ether solvents such as diethyl ether and tetrahydrofuran; ketone solvents such as acetone and methyl isobutyl ketone; ester solvents such as ethyl acetate; aliphatic hydrocarbon solvents such as hexane; aromatic hydrocarbon solvents such as toluene; halogenated hydrocarbon solvents such as methylene chloride, chloroform, and 1,2-dichlorobenzene; amide solvents such as N,N-dimethylformamide and N-methylpyrrolidone; sulfoxide solvents such as dimethyl sulfoxide; carboxylic acid solvents such as acetic acid, propionic acid, and butyric acid; and imidazole.

The amount of solvent used in the reaction between compound (pt5) and compound (MA2) is typically 0.1 to 1,000 parts by mass per part by mass of compound (pt5).

In the reaction between compound (pt5) and compound (MA2), a base may be present to ensure efficient reaction. The base may be an organic or inorganic base, with organic bases being preferred, and 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 being more preferred.

When a base is used in the reaction of compound (pt5) with compound (MA2), the amount of base used is typically 0.1 mol or more and 50 mol or less, and preferably 0.5 mol or more and 30 mol or less, per 1 mol of compound (pt5).

The reaction temperature when reacting compound (pt5) with compound (MA2) is typically -100°C or higher and 300°C or lower. The reaction time when reacting compound (pt5) with compound (MA2) is typically 0.5 hours to 300 hours.

When ^R1 is a hydrogen atom, compound (I) can be produced by reacting compound (pt4) with compound (MA2) instead of compound (pt5), without reacting compound (pt4) with compound (MA1).

After completion of each of the above reactions, the method for extracting the target compound is not particularly limited, and various known methods can be used. After extraction, the resulting residue may be purified by column chromatography, recrystallization, or the like. The chemical structure of the resulting compound can be analyzed using known analytical methods and their conditions. Such analytical methods include, but are not limited to, 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.

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.

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

As long as the dye (A1-1) does not contain compound (I), known dyes can be used, including solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified as dyes in the Color Index (published by The Society of Dyers and Colourists) and known dyes listed in Dyeing Notes (Shikisensha). In addition, examples of dyes that can be used based on their chemical structure include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, phthalocyanine dyes, perylene dyes, quinophthalone dyes, and isoindoline dyes. Among these, organic solvent-soluble dyes are preferred.

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 dyes such as C.I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35;
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, 1 57, 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;
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, 158, 160, 172, 176, 18 2, 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, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426;
C.I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;
C.I. Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;
C.I. 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, 335, 340;
C. I. Acid dyes such as C. I. 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;
C.I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;
C.I. 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;
C.I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
C.I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;
C.I. 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, 166 , 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;
C.I. Direct Dyes such as C.I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 79, 82;
C.I. Disperse Yellow 51, 54, 76;
C.I. Disperse Violet 26, 27;
C.I. Disperse dyes such as C.I. Disperse Blue 1, 14, 56, 6;
C.I. Basic Red 1, 10;
C.I. 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;
C.I. Basic Violet 2;
C.I. Basic Red 9;
C.I. Basic dyes such as C.I. Basic Green 1;
C.I. Reactive Yellow 2, 76, 116;
C.I. Reactive Orange 16;
C.I. Reactive dyes such as C.I. Reactive Red 36;
C.I. Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;
C. I. Mordant 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;
C.I. Mordant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;
C. I. 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;
C.I. Mordant 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;
C. I. Mordant dyes such as C. I. Mordant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53;
C.I. Vat dyes such as C.I. Vat Green 1;

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

Specific examples of pigments classified as C.I. pigments include yellow pigments such as C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214, and 231;
Orange pigments such as C.I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, and 73;
red pigments such as C.I. 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, and 273;
blue pigments such as C.I. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, and 60;
Violet pigments such as C.I. Pigment Violet 1, 19, 23, 32, 36, and 38;
green pigments such as C.I. Pigment Green 7, 36, 58, 59, 62, and 63;
Brown pigments such as C.I. Pigment Brown 23 and 25;
black pigments such as C.I. Pigment Black 1, 7, 31, and 32;

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

When the colored resin composition contains a solvent (E), a colored composition containing the colorant (A) and the 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 the colored composition. When the colorant (A) is not soluble in the solvent (E), for example, when the colorant (A) contains a pigment (A1-2), the colored composition can be prepared by dispersing the colorant (A) in the solvent (E) and mixing them. The colored composition may contain some or all of the solvent (E) contained in the colored resin composition.

The solids content in the coloring composition is less than 100% by mass, preferably 0.01% by mass to 99.99% by mass, more preferably 0.1% by mass to 99.9% by mass, even more preferably 0.1% by mass to 99% by mass, still more preferably 1% by mass to 90% by mass, particularly preferably 1% by mass to 80% by mass, even more preferably 1% by mass to 70% by mass, particularly preferably 1% by mass to 60% by mass, and most preferably 1% by mass to 50% by mass, based on the total amount of the coloring composition.

The content of colorant (A) in the coloring 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, still 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 coloring composition.

If necessary, colorant (A) may be subjected to a variety of treatments, including rosin treatment, surface treatment using a derivative having an acidic or basic group introduced therein, grafting of a polymer compound onto the surface of colorant (A), atomization using a sulfuric acid atomization method or a salt milling method, washing with an organic solvent or water to remove impurities, and removal of ionic impurities using an ion exchange method. It is preferable that the particle size of colorant (A) is approximately uniform.

By adding a dispersant and carrying out a dispersion treatment on the colorant (A), the colorant (A) can be uniformly dispersed in the solution. When two or more types of colorant (A) are used in combination, each may be dispersed individually, or multiple types may be mixed and dispersed.

Examples of dispersants include surfactants, which may be cationic, anionic, nonionic, or amphoteric. Specific examples include polyester, polyamine, and acrylic surfactants. These dispersants may be used alone or in combination of two or more. Examples of dispersants by trade name include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), FLORENE (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Corporation), EFKA (registered trademark) (manufactured by BASF), Ajisper (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK), and BYK (registered trademark) (manufactured by BYK).

When a dispersant is used, the amount of the dispersant (solid content) used is typically 1 part by mass or more and 10,000 parts by mass or less, preferably 5 parts by mass or more and 5,000 parts by mass or less, more preferably 10 parts by mass or more and 3,000 parts by mass or less, and even more preferably 15 parts by mass or more and 1,000 parts by mass or less, per 100 parts by mass of colorant (A) in the coloring composition. When the amount of the dispersant used is within the above range, a coloring composition in a more uniformly dispersed state tends to be obtained.

When a coloring composition containing colorant (A) and solvent (E) is prepared in advance and then used to prepare a colored resin composition, the coloring composition may already contain some or all, preferably some, of the resin (B) contained in the colored resin composition. By including resin (B) in advance, the dispersion stability of the coloring composition can be further improved.

When 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, relative to 100 parts by mass of colorant (A) in the coloring composition.

The content of the colorant (A) is preferably 0.1% by mass or more and 50% by mass or less, more preferably 0.5% by mass or more and 40% by mass or less, even more preferably 1.0% by mass or more and 30% by mass or less, and even more preferably 1.5% by mass or more and 20% by mass or less, based on the total amount of solids in the colored resin composition. When the content of the colorant (A) is within the above range, the color density when made into a color filter is sufficient, and since the necessary amount of resin (B) can be contained in the composition, a pattern with sufficient mechanical strength can be formed, which is preferable.
Here, the "total amount of solids" in this specification refers to the amount obtained by subtracting the content of the solvent from the total amount of the colored resin composition. The total amount of solids and the content of each component relative to the total amount of solids can be measured by known analytical means such as liquid chromatography or gas chromatography.

The content ratio of colorant (A) to resin (B) (described below) in the colored resin composition (resin (B)/colorant (A)) is, for example, preferably 2.0 or more by mass, more preferably 3.0 or more, and even more preferably 4.0 or more, and is preferably 20 or less, more preferably 15 or less, and even more preferably 13 or less.

<Resin (B)>
Resin (B) is not particularly limited as long as it is different from a thermoplastic resin and can be used to form a photoresist, but is preferably an alkali-soluble resin, and more preferably an alkali-soluble resin having a carboxylic acid.

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

Examples of the monomer (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, and o-, m-, and p-vinylbenzoic acid;
Unsaturated dicarboxylic acids such as maleic acid, fumaric acid, citraconic acid, mesaconic acid, itaconic acid, 3-vinylphthalic acid, 4-vinylphthalic acid, 3,4,5,6-tetrahydrophthalic acid, 1,2,3,6-tetrahydrophthalic acid, dimethyltetrahydrophthalic acid, and 1,4-cyclohexenedicarboxylic acid;
bicyclounsaturated compounds containing a carboxy group, such as methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo[2.2.1]hept-2-ene, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene, 5-carboxy-5-methylbicyclo[2.2.1]hept-2-ene, 5-carboxy-6-methylbicyclo[2.2.1]hept-2-ene, and 5-carboxy-6-ethylbicyclo[2.2.1]hept-2-ene;
carboxylic acid anhydrides such as the anhydrides of the above unsaturated dicarboxylic acids excluding fumaric acid and mesaconic acid;
Unsaturated mono[(meth)acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids, such as mono[2-(meth)acryloyloxyethyl] succinate and mono[2-(meth)acryloyloxyethyl] phthalate;
Unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α-(hydroxymethyl)acrylic acid; and the like.
Among these, acrylic acid, methacrylic acid, maleic anhydride, etc. are preferred from the viewpoint of copolymerization reactivity and solubility of the resulting resin in an alkaline aqueous solution.
In this specification, the term "(meth)acrylic acid" refers to at least one selected from the group consisting of acrylic acid and methacrylic acid. The terms "(meth)acryloyl" and "(meth)acrylate" also have the same meaning.

Monomer (b) refers to a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring, and a tetrahydrofuran ring (oxolane ring)) and an ethylenically unsaturated bond. Monomer (b) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth)acryloyloxy group.

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

Examples of monomer (b1) include a monomer having a structure in which an unsaturated aliphatic hydrocarbon has been epoxidized (hereinafter, sometimes referred to as "(b1-1)" or "monomer (b1-1)"), and a monomer having a structure in which an unsaturated alicyclic hydrocarbon has been epoxidized (hereinafter, sometimes referred to as "(b1-2)" or "monomer (b1-2)").

Monomer (b1-1) is preferably a monomer having a glycidyl group and an ethylenically unsaturated bond. Specific examples of monomer (b1-1) include glycidyl (meth)acrylate, β-methylglycidyl (meth)acrylate, β-ethylglycidyl (meth)acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis( Examples include 2,4-bis(glycidyloxymethyl)styrene, 2,5-bis(glycidyloxymethyl)styrene, 2,6-bis(glycidyloxymethyl)styrene, 2,3,4-tris(glycidyloxymethyl)styrene, 2,3,5-tris(glycidyloxymethyl)styrene, 2,3,6-tris(glycidyloxymethyl)styrene, 3,4,5-tris(glycidyloxymethyl)styrene, and 2,4,6-tris(glycidyloxymethyl)styrene.

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

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

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

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

R ^a and R ^b are preferably 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.

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 groups.

^Xa and ^Xb are preferably a single bond, a methylene group, an ethylene group, a * _-CH2 -O- (* represents a bond to O) group, or a * _-CH2CH2 - _O- group, and more preferably a single bond or a * _{-CH2CH2 -} O- group (* represents a bond to O).

Examples of compounds represented by formula (BI) include compounds 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.

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

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

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)acryloyloxymethyloxetane, 3-ethyl-3-(meth)acryloyloxymethyloxetane, 3-methyl-3-(meth)acryloyloxyethyloxetane, and 3-ethyl-3-(meth)acryloyloxyethyloxetane.

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

Examples of the monomer (c) include methyl(meth)acrylate, ethyl(meth)acrylate, n-butyl(meth)acrylate, sec-butyl(meth)acrylate, tert-butyl(meth)acrylate, 2-ethylhexyl(meth)acrylate, dodecyl(meth)acrylate, lauryl(meth)acrylate, stearyl(meth)acrylate, cyclopentyl(meth)acrylate, cyclohexyl(meth)acrylate, 2-methylcyclohexyl(meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decan-8-yl(meth)acrylate (commonly known as "dicyclopentanyl(meth)acrylate" in the technical field, and sometimes referred to as "tricyclodecyl(meth)acrylate"), tricyclo[5.2.1.0 ^2,6 ]decan-9-yl(meth)acrylate, tricyclo[5.2.1.0 (meth)acrylic acid esters such as tricyclo[ ^{5.2.1.0 2,6} ]decen-8-yl(meth)acrylate (commonly known in the technical field as "dicyclopentenyl(meth)acrylate"), tricyclo[5.2.1.0 ^2,6 ]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-methoxybicyclo[2.2.1]hept-2-ene chloro[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept -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 bicyclounsaturated compounds such as ene, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene;
dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide;
Examples 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, from the viewpoints of copolymerization reactivity and heat resistance, styrene, vinyltoluene, tricyclo[5.2.1.0 ^2,6 ]decan-8-yl(meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decan-9-yl(meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decen-8-yl(meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decen-9-yl(meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo[2.2.1]hept-2-ene, benzyl(meth)acrylate, and the like are preferred.

In the resin [K1], the ratio of the structural units derived from each of these to all the structural units constituting the resin [K1] is as follows:
Structural units derived from (a): 2 to 60 mol %
Structural units derived from (b): 40 to 98 mol%
It is preferred that
Structural units derived from (a): 10 to 50 mol %
Structural units derived from (b): 50 to 90 mol %
It is more preferable that:
When the ratio of the structural units of the resin [K1] is within the above range, the colored resin composition tends to have excellent storage stability, developability when forming a colored pattern, and solvent resistance of the obtained optical filter.

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

Specifically, one method involves placing predetermined amounts of (a) and (b), a polymerization initiator, a solvent, and the like in a reaction vessel, replacing oxygen with nitrogen, for example, to create a deoxygenated atmosphere, and then heating and maintaining the temperature while stirring. The polymerization initiators and solvents used here are not particularly limited, and those commonly used in the relevant field can be used. For example, polymerization initiators include azo compounds (2,2'-azobisisobutyronitrile, 2,2'-azobis(2,4-dimethylvaleronitrile), etc.) and organic peroxides (benzoyl peroxide, etc.). Solvents that dissolve the respective monomers are sufficient, and examples of the solvents that will be described later as solvent (E) for the colored resin composition of the present invention include the solvents described below.

The resulting copolymer may be used as a solution after the reaction as is, or as a concentrated or diluted solution, or as a solid (powder) obtained by reprecipitation or other methods. 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 as is to prepare the colored resin composition of the present invention, thereby simplifying the production process for the colored resin composition of the present invention.

In the resin [K2], the ratio of the structural units derived from each of these to all the structural units constituting the resin [K2] is as follows:
Structural units derived from (a): 2 to 45 mol %
Structural units derived from (b): 2 to 95 mol %
Structural units derived from (c): 1 to 65 mol%
It is preferred that
Structural units derived from (a): 5 to 40 mol %
Structural units derived from (b): 5 to 80 mol %
Structural units derived from (c): 5 to 60 mol %
It is more preferable that:
When the ratio of the structural units of the resin [K2] is within the above range, the colored resin composition has good storage stability, and the developability when forming a colored pattern, and the obtained optical filter tends to have excellent solvent resistance, heat resistance, and mechanical strength.

Resin [K2] can be produced, for example, in the same manner as described for producing resin [K1].

In the resin [K3], the ratio of the structural units derived from each of these to all the structural units constituting the resin [K3] is as follows:
Structural units derived from (a): 2 to 60 mol %
Structural units derived from (c): 40 to 98 mol%
It is preferred that
Structural units derived from (a): 10 to 50 mol %
Structural units derived from (c): 50 to 90 mol %
It is more preferable that:
Resin [K3] can be produced, for example, in the same manner as described above for producing resin [K1].

Resin [K4] can be produced by obtaining a copolymer of (a) and (c), and then adding the cyclic ether having 2 to 4 carbon atoms contained in (b) to the carboxylic acid and/or carboxylic acid anhydride contained in (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, the ratio of the structural units derived from each of the components is preferably the same as that described for resin [K3].

Next, a part 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 contained in (b).
Following the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced with air from nitrogen, and (b) a catalyst for the reaction of a carboxylic acid or a carboxylic acid anhydride with a cyclic ether (e.g., tris(dimethylaminomethyl)phenol, etc.), a polymerization inhibitor (e.g., hydroquinone, etc.), etc. are placed in the flask, and the mixture is reacted, for example, at 60 to 130°C for 1 to 10 hours, thereby producing resin [K4].
The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, per 100 mol of (a). By using this range, the storage stability of the colored resin composition, the developability when forming a pattern, and the balance of the solvent resistance, heat resistance, mechanical strength, and sensitivity of the resulting pattern tend to be good. Because the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b1) is preferred as (b) used in resin [K4], and (b1-1) is 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 of (a), (b), and (c), and the amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass per 100 parts by mass of the total of (a), (b), and (c).
The reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc. As with the polymerization conditions, the charging method and reaction temperature can be appropriately adjusted in consideration of the production equipment, the amount of heat generated by the polymerization, etc.

Resin [K5] is obtained in the first step by the same method as in the production of Resin [K1] described above, to obtain a copolymer of (b) and (c). As in the above, the obtained copolymer may be used as a solution after the reaction as is, a concentrated or diluted solution, or a solid (powder) obtained by a method such as reprecipitation.
The ratios of the structural units derived from (b) and (c) to the total number of moles of all structural units constituting the copolymer are as follows:
Structural units derived from (b): 5 to 95 mol %
Structural units derived from (c): 5 to 95 mol%
It is preferred that
Structural units derived from (b): 10 to 90 mol %
Structural units derived from (c): 10 to 90 mol%
It is more preferable that:

Furthermore, under the same conditions as in the production method of resin [K4], resin [K5] can be obtained by reacting a cyclic ether derived from (b) contained in a copolymer of (b) and (c) with a carboxylic acid or carboxylic anhydride contained in (a).
The amount of (a) used to react with the copolymer is preferably 5 to 80 moles per 100 moles of (b). Because the reactivity of cyclic ethers is high and unreacted (b) is unlikely to remain, (b1) is preferred as (b) used in resin [K5], and (b1-1) is more preferred.

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 a carboxylic acid anhydride is reacted with the carboxylic acid anhydride.
Examples of the carboxylic acid anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo[2.2.1]hept-2-ene anhydride, etc. The amount of the carboxylic acid anhydride used is preferably 0.5 to 1 mole per mole of the amount of (a) used.

Specific examples of the resin (B) include resins [K1] such as 3,4-epoxycyclohexylmethyl (meth)acrylate/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl acrylate/(meth)acrylic acid copolymer, glycidyl (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer, glycidyl (meth)acrylate/styrene/(meth)acrylic acid copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl acrylate/(meth)acrylic acid/N-cyclohexylmaleimide copolymer, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl acrylate/(meth)acrylic acid/N-cyclohexylmaleimide/2-hydroxyethyl (meth)acrylate copolymer, 3-methyl-3-(meth)acryloyloxymethyloxetane/(meth)acrylic acid/styrene copolymer, and other resins [K2]; benzyl (meth)acrylate/(meth)acrylic acid copolymer, styrene/(meth)acrylic acid copolymer, and other resins [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 Resins [K4] such as a resin obtained by adding glycidyl (meth)acrylate to a (meth)acrylate/benzyl (meth)acrylate/(meth)acrylic acid copolymer; resins [K5] such as a resin obtained by reacting a tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate copolymer with (meth)acrylic acid, or a resin obtained by reacting a tricyclodecyl (meth)acrylate/styrene/glycidyl (meth)acrylate copolymer with (meth)acrylic acid; and resins [K6] such as a resin obtained by reacting a tricyclodecyl (meth)acrylate/glycidyl (meth)acrylate copolymer with (meth)acrylic acid and further reacting the resulting resin with tetrahydrophthalic anhydride.

Resin (B) is more preferably resin [K1] or resin [K2], and especially preferably resin [K1].

The polystyrene-equivalent weight average molecular weight (Mw) of resin (B) is preferably from 1,000 to 100,000, more preferably from 2,000 to 50,000, and even more preferably from 3,000 to 30,000. When the weight average molecular weight is within the above range, the solubility of the unexposed area in a developer is high, and the resulting pattern tends to have high film retention and hardness.
The polydispersity [weight average molecular weight (Mw)/number average molecular weight (Mn)] of the resin (B) 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.

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

The content of resin (B) is preferably 5 to 98% by mass, more preferably 10 to 95% by mass, and even more preferably 15 to 93% by mass, based on 100% by mass of the solids content of the colored resin composition. Furthermore, when the colored resin composition contains polymerizable compound (C) and polymerization initiator (D), 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 solids content of the colored resin composition. When the content of resin (B) is within the above range, the unexposed areas tend to have high solubility in the developer.

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

Examples of polymerizable compounds having one ethylenically unsaturated bond include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, and the above-mentioned monomers (a), (b), and (c).

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.

Among these, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris(2-(meth)acryloyloxyethyl)isocyanurate, ethylenediaminetetraacetic acid ester ... Examples of suitable acrylates 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.

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

The content of the polymerizable compound (C) may be, for example, from 1% by mass to 99% by mass, preferably from 5% by mass to 90% by mass, more preferably from 10% by mass to 80% by mass, and even more preferably from 20% by mass to 70% by mass, relative to the total amount of solids in the colored resin composition.

<Polymerization initiator (D)>
The polymerization initiator (D) is not particularly limited as long as it is a compound that can generate active radicals, acids, etc. by the action of light or heat and initiate polymerization, and known polymerization initiators can be used.

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

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

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

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, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, and 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole. Examples of such compounds include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B No. 48-38403 and JP-A No. 62-174204), and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboalkoxy groups (see, for example, JP-A No. 7-10913).

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, 2,4-bis(trichloromethyl)-6-[2-( 5-methylfuran-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(furan-2-yl)ethenyl]-1,3,5-triazine, 2,4-bis(trichloromethyl)-6-[2-(4-diethylamino-2-methylphenyl)ethenyl]-1,3,5-triazine, and 2,4-bis(trichloromethyl)-6-[2-(3,4-dimethoxyphenyl)ethenyl]-1,3,5-triazine.

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

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

Polymerization initiator (D) is preferably a polymerization initiator containing 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 containing an O-acyloxime compound.

The content of polymerization initiator (D) is preferably 0.1 to 30 parts by mass, and more preferably 1 to 20 parts by mass, relative to 100 parts by mass of the total amount of all resins (B) and polymerizable compounds (C) contained in the colored resin composition. When the content of polymerization initiator (D) is within this range, sensitivity tends to be increased and exposure time tends to be shortened, thereby improving the productivity of color filters.

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

Examples of the polymerization initiation aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

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-dimethyl-p-toluidine, 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, and 4,4'-bis(ethylmethylamino)benzophenone, with 4,4'-bis(diethylamino)benzophenone being preferred. Commercially available amine compounds, such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.), may also be used.

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.

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

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.

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

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

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 gamma-butyrolactone.

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, phenetole, and methylanisole.

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, and 2-ethoxy-2-methylpropionate. Examples of such esters include ethyl phosphate, 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.

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.

Alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

Aromatic hydrocarbon solvents include benzene, toluene, xylene, mesitylene, etc.

Amide solvents include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.

Preferred solvents (E) are propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, N-methylpyrrolidone, ethyl lactate, and cyclohexanone.

When solvent (E) is contained, the content of solvent (E) is typically 99.99% by mass or less, preferably 40% by mass or more and 99% by mass or less, more preferably 50% by mass or more and 97% by mass or less, even more preferably 70% by mass or more and 95% by mass or less, and even more preferably 75% by mass or more and 95% by mass or less, based on the total amount of the colored resin composition. In other words, the total amount of solids in the colored resin composition is typically 0.01% by mass or more, preferably 1% by mass or more and 60% by mass or less, more preferably 3% by mass or more and 50% by mass or less, even more preferably 5% by mass or more and 30% by mass or less, and even more preferably 5% by mass or more and 25% by mass or less. When the content of solvent (E) is within the above range, good flatness is achieved during application, and the color density is sufficient when a color filter is formed, tending to result in good display characteristics.

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

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

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

Examples of silicone surfactants containing fluorine atoms include surfactants containing siloxane bonds and fluorocarbon chains within the molecule. Specific examples include Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

When a leveling agent (F) is contained, the content of the leveling agent (F) is preferably 0.0005% by mass or more and 1% by mass or less, more preferably 0.001% by mass or more and 0.5% by mass or less, and even more preferably 0.005% by mass or more and 0.1% by mass or less, relative to the total amount of the colored resin composition. Note that 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.

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

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

<Color filter manufacturing method>
A color filter, which may be a color conversion layer, can be formed from the colored resin composition. Methods for forming a colored pattern include photolithography, inkjet printing, and printing. Among these, photolithography is preferred. The photolithography method involves applying the colored resin composition to a substrate, drying the composition to form a colored resin composition layer, and then exposing and developing the colored resin composition layer through a photomask. In the photolithography method, a colored coating film, which is a cured product of the colored resin composition layer, can be formed by not using a photomask during exposure and/or not developing the layer. Alternatively, the colored resin composition can be applied to a substrate, dried to form a colored resin composition layer, and then post-baked to form a colored coating film. The colored pattern or colored coating film thus formed is the color filter of the present invention.

The film thickness of the color filter to be produced is not particularly limited and can be adjusted appropriately 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.

Substrates that can be used include glass plates such as quartz glass, borosilicate glass, alumina silicate glass, and silica-coated soda lime glass; resin plates such as polycarbonate, polymethyl methacrylate, and polyethylene terephthalate; silicon; and substrates with aluminum, silver, or silver/copper/palladium alloy thin films formed thereon. These substrates may also have other color filter layers, resin layers, transistors, circuits, etc. formed on them.

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

Next, the colored resin composition layer is exposed through a photomask to form the desired colored pattern. There are no particular restrictions on the pattern on the photomask, and a pattern appropriate for the intended application can be used. Furthermore, it is preferable to use exposure equipment such as a mask aligner or stepper, as this allows for uniform irradiation of the entire exposure surface with parallel light and allows for accurate alignment of the photomask with the substrate on which the colored resin composition layer is formed.

The light source used for exposure is preferably one that emits light with a wavelength of 250 nm or more and 450 nm or less. For example, light below 350 nm can be cut using a filter that cuts 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.

A colored pattern is formed on the substrate by contacting the exposed colored resin composition layer with a developer and developing it. The unexposed portions of the colored resin composition layer are dissolved in the developer and removed by development. The developer is preferably, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium bicarbonate, sodium carbonate, or tetramethylammonium hydroxide. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01% by mass or more and 10% by mass or less, more preferably 0.03% by mass or more and 5% by mass or less. Furthermore, the developer may contain a surfactant.
The developing method may be any of a puddle method, a dipping method, a spray method, etc. Furthermore, the substrate may be tilted at any angle during development.
After development, the substrate is preferably washed with water.

Furthermore, it is preferable to post-bake the obtained colored pattern. The post-bake temperature is preferably 150°C or higher and 250°C or lower, and more preferably 160°C or higher and 240°C or lower. The post-bake time is preferably 1 minute or higher and 120 minutes or lower, and more preferably 10 minutes or higher and 60 minutes or lower.

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

The present invention will be explained in more detail below using examples, but the present invention is not limited to the examples below, and it is of course possible to make appropriate modifications within the scope of the intent described above and below, all of which are within the technical scope of the present invention. In the following, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass."

In the following examples, the structures of the compounds were confirmed by mass spectrometry (LC: Agilent Model 1200, MASS: Agilent Model LC/MSD6130).

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

(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 filtration 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) (yield 90%).

<Identification of compound (pt2)>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 231
Exact Mass: 230

(Synthesis Example 2)
25 parts of the compound (pt2) obtained in Synthesis Example 1, 1.5 parts of potassium carbonate (Kanto Chemical Co., Ltd.), 312 parts of acetonitrile (Kanto Chemical Co., Ltd.), and 2 parts of water were mixed and stirred at 80°C for 5 hours. When the mixture was 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 resulting residue was dried under reduced pressure at 60°C and purified using a silica gel column (solvent: chloroform/ethyl acetate = 10/1, vol/vol), yielding 17 parts of a yellow-brown compound represented by formula (pt3) (yield 68%).

<Identification of compound (pt3)>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 231
Exact Mass: 230

(Synthesis Example 3)
To 1.0 part of the compound (pt3) obtained in Synthesis Example 2, 5.6 parts of 98% sulfuric acid (Kanto Chemical Co., Inc.) was added, and the mixture was stirred at 50°C for 10 hours. The reaction solution was added dropwise to ice water, and the resulting residue was filtered. The resulting solid was washed with water, then washed with methanol, and dried under reduced pressure at 60°C to obtain 0.90 parts of the compound represented by formula (pt4) (yield 83%).

<Identification of compound (pt4)>
(Mass spectrometry) Ionization mode = ESI-: m/z = [M-H] ^- 248
Exact Mass: 249

(Synthesis Example 4)
1.0 part of compound (pt4) obtained in Synthesis Example 3 was dissolved in 50 parts of N,N-dimethylformamide, and 0.5 parts of 1-hexylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) was added, followed by stirring at room temperature for 5 hours. The reaction solution was added dropwise to a mixed solvent of hexane and chloroform, and the resulting residue was filtered. The resulting solid was purified using an alumina column (solvent: tetrahydrofuran/water=1/1, vol/vol) and dried under reduced pressure at 60°C, yielding 0.20 part of a compound represented by formula (Ii-6) (hereinafter, sometimes referred to as compound (Ii-6)) (yield: 16%).

<Identification of Compound (Ii-6)>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 349
Exact Mass: 348

(Synthesis Example 5)
1.0 part of the compound (pt4) obtained in Synthesis Example 3, 3.1 parts of iodoethane (manufactured by Tokyo Chemical Industry Co., Ltd.), 2.4 parts of potassium carbonate (manufactured by Kanto Chemical Co., Inc.), and 50 parts of acetonitrile were mixed and stirred for 12 hours at 40° C. The reaction liquid was filtered through Celite, the filtrate was concentrated, and the resulting solid was purified on an alumina column (solvent: gradient from chloroform to acetonitrile) and dried under reduced pressure at 60° C. to obtain 0.56 parts of the compound represented by formula (pt5) (yield: 47%).

<Identification of compound (pt5)>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 278
Exact Mass: 277

(Synthesis Example 6)
0.20 parts of a compound represented by formula (Ii-83) (hereinafter may be referred to as compound (Ii-83)) was obtained in the same manner as in Synthesis example 4, except for changing 1.0 part of compound (pt4) with 1.1 parts of compound (pt5) obtained in Synthesis example 5, and changing 1.0 part of 1-hexylamine with 0.9 parts of n-butylamine (yield 18%).

<Identification of Compound (Ii-83)>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 349
Exact Mass: 348

(Synthesis Example 7)
0.2 parts of a compound represented by formula (Ii-66) (hereinafter may be referred to as compound (Ii-66)) was obtained (yield 21%) in the same manner as in Synthesis example 4, except for changing 1.0 parts of 1-hexylamine to 1.1 parts of benzylamine.

<Identification of Compound (Ii-66)>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 355
Exact Mass: 354

(Synthesis Example 8)
0.1 part of a compound represented by formula (Ii-190) (hereinafter, may be referred to as compound (Ii-190)) was obtained in the same manner as in Synthesis example 4, except for changing 1.0 part of 1-hexylamine to 1.2 parts of diisobutylamine (yield 9%).

<Identification of Compound (Ii-190)>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 377
Exact Mass: 376

(Synthesis Example 9)
0.3 parts of a compound represented by formula (Ii-320) (hereinafter, may be referred to as compound (Ii-320)) was obtained in the same manner as in Synthesis example 4, except for changing 1.0 parts of 1-hexylamine to 1.1 parts of piperidine (yield 28%).

<Identification of Compound (Ii-320)>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 333
Exact Mass: 332

(Synthesis Example 10)
The compound represented by the following formula (x) (hereinafter sometimes referred to as compound (x)) was synthesized in accordance with the description of Synthesis Example 2 of JP-A-2020-079397.

(Synthesis Example 11)
A flask equipped with a reflux condenser, a dropping funnel, and a stirrer was purged with nitrogen by flowing an appropriate amount of nitrogen, and 280 parts of propylene glycol monomethyl ether acetate was added and heated to 80°C with stirring. Next, a mixed solution of 38 parts of acrylic acid, 289 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decan-9-yl acrylate (content ratio: 1:1 by molar ratio), and 125 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a solution of 33 parts of 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the dropwise addition was completed, the mixture was kept at 80°C for 4 hours and then cooled to room temperature to obtain a copolymer (Resin B1) solution with a solids content of 35.1% and a viscosity of 125 mPa·s measured with a Brookfield viscometer (23°C). The weight-average molecular weight Mw of the produced copolymer was 9.2 × 10 ³ , a polydispersity of 2.08, and an acid value converted to solids of 77 mg-KOH/g. Resin B1 has the following structural units.

Example 1
(1) Preparation of Colored Composition The following components were mixed to obtain Colored Composition 1.
(A) Colorant: Compound (Ii-6) 2.6 parts (B) Resin: Resin B1 solution 54 parts (E) Solvent: Propylene glycol monomethyl ether acetate 420 parts (2) Preparation of Colored Resin Composition Next, the following components were mixed to obtain a colored resin composition 1.
Coloring composition 1 478 parts (C) Polymerizable compound: Dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 40 parts (D) Polymerization initiator: N-benzoyloxy-1-(4-phenylsulfanylphenyl)octan-1-one-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 2 parts (F) Leveling agent: Polyether-modified silicone oil (Toray Silicone SH8400: manufactured by Dow Corning Toray Co., Ltd.) 0.15 parts

(3) Preparation of colored coating film (color filter) A colored resin composition was applied by spin coating onto a 5 cm square glass substrate (Eagle XG; manufactured by Corning Incorporated) so that the film thickness after post-baking would be 2 μm, and 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 irradiated with light using an exposure machine (TME-150RSK; manufactured by Topcon Corporation) in an air atmosphere at an exposure dose of 80 mJ / cm ² (365 nm standard). After light irradiation, the layer was post-baked in an oven at 230 ° C. for 30 minutes to obtain a colored coating film.
The thickness of the colored coating film was measured using DEKTAK3 (manufactured by Japan Vacuum Technology Co., Ltd.). The results are shown in Table 6.

(4) Contrast Evaluation The contrast of the obtained colored coating film was measured using a contrast meter (CT-1: manufactured by Tsubosaka Electric Co., Ltd., color difference meter BM-5A: manufactured by Topcon Corporation, light source: F-10, polarizing film: manufactured by Tsubosaka Electric Co., Ltd.). The blank value at the time of measurement was 30,000. If the contrast of the colored coating film is good, it can be said that the contrast of a colored pattern produced from the same colored resin composition is also good. The results are shown in Table 6.

(5) Heat Resistance Test The obtained colored coating film was heated in an oven under atmospheric pressure at 230°C for 120 minutes. The color difference ΔE*ab was calculated from the xy chromaticity coordinates (x, y) and Y measured values before and after the test using the method described in JIS Z 8730:2009 (7. Method for calculating color difference). The smaller the color difference ΔE*ab, the smaller the color change. If ΔE*ab is 10 or less, the colored coating film can be said to have no practical problems as a color filter. Furthermore, if the heat resistance of the colored coating film is good, it can be said that a colored pattern made from the same colored resin composition also has good heat resistance. The results are shown in Table 7.

(6) Lightfastness Test An ultraviolet cut filter (COLORED OPTICAL GLASS L38; manufactured by Hoya Co., Ltd.; cuts light below 380 nm) was placed on the obtained colored coating film, and xenon lamp light was irradiated for 48 hours using a lightfastness tester (SUNTEST CPS+; manufactured by Toyo Seiki Co., Ltd.). The color difference ΔE*ab was calculated from the xy chromaticity coordinates (x, y) and Y measured values before and after the test using the method described in JIS Z 8730:2009 (7. Method for calculating color difference). The smaller the color difference ΔE*ab, the smaller the color change. If ΔE*ab is 10 or less, it can be said that the colored coating film is practically satisfactory as a color filter. Furthermore, if the lightfastness of the colored coating film is good, it can be said that a colored pattern produced from the same colored resin composition also has good lightfastness. The results are shown in Table 7.

<Comparative Example 1>
A colored resin composition was prepared in the same manner as in Example 1, except that compound (Ii-6) in Example 1 was replaced with compound (x), and a colored coating film was produced and evaluated for contrast. The results are shown in Table 6.

The colored coating films obtained from the colored resin compositions prepared in the same manner as in Example 1, except that the compound represented by formula (Ii-83), formula (Ii-66), formula (Ii-190), or formula (Ii-320) was used instead of the compound represented by formula (Ii-6), all exhibited high contrast and excellent heat and light resistance, similar to Example 1.

Claims (4)

A colored resin composition comprising a colorant and a resin, wherein the colorant comprises a compound represented by formula (I).

[In formula (I),
R ¹ to R ³ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent.
^R2 and ^R3 may be joined together with the nitrogen atom to which they are bonded to form a ring which may have a substituent.
R ⁴ to R ⁸ each independently represent a hydrogen atom, —R ⁹ , —O—R ⁹ , —CO—O—R ⁹ , —O—CO—R ⁹ , a halogen atom, a hydroxy group, a carboxy group, a sulfo group, or a nitro group.
R ⁹ represents a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and when there are multiple R ^9s , they may be the same or different. The colored resin composition according to claim 1, further comprising a polymerizable compound and a polymerization initiator. A color filter formed from the colored resin composition according to claim 1 or 2. A display device including the color filter described in claim 3.