JP7474090B2 - Compound and colored resin composition - Google Patents

Description

The present invention relates to a benzoperylene compound useful as a dye, and a colored resin composition containing the benzoperylene compound.

The colored resin composition is used in the manufacture of color filters for use in displays such as liquid crystal displays, electroluminescent displays, and plasma displays. Such colored resin compositions contain a colorant to obtain a desired color tone, and a perylene compound represented by the following formula (x) is known as a colorant (Non-Patent Document 1).

BASF Technical Report (Lumogen (registered trademark) F), BASF, November 1997, 2-6

However, the above-mentioned conventionally known perylene compounds sometimes do not have sufficient light resistance. Therefore, the present invention aims to provide a colored resin composition capable of forming a color filter having excellent light resistance, and a benzoperylene compound useful as a dye contained in the colored resin composition.

［式（Ｉ）中、
Ｒ¹及びＲ²は、互いに独立に、置換基を有していてもよい炭素数６～２０のアリール基又は置換基を有していてもよい炭素数１～２０のヘテロアリール基を表す。
Ｒ³、Ｒ⁶及びＲ⁸は、互いに独立に、置換基を有してもよい炭素数１～３０の炭化水素基、置換基を有してもよい炭素数１～３０の芳香族複素環基、又はこれらを組み合わせた基を表す。
Ｒ⁴、Ｒ⁵、Ｒ⁷及びＲ⁹は、互いに独立に、水素原子、－Ｒ¹¹、－Ｏ－Ｒ¹¹、－ＣＯ－Ｏ－Ｒ¹¹、ハロゲン原子、ヒドロキシ基、カルボキシ基又はニトロ基を表す。
Ｒ¹¹は、置換基を有してもよい炭素数１～３０の炭化水素基を表し、Ｒ¹¹が複数ある場合、それらは互いに同じでも異なっていてもよい。］
［２］ 着色剤が、さらにペリレン化合物を含む［１］に記載の着色樹脂組成物。
［３］ さらに重合性化合物及び重合開始剤を含む［１］又は［２］に記載の着色樹脂組成物。
［４］ さらに溶剤を含む［１］～［３］のいずれかに記載の着色樹脂組成物。
［５］ ［１］～［４］のいずれかに記載の着色樹脂組成物から形成されるカラーフィルタ。
［６］ ［５］に記載のカラーフィルタを含む表示装置。
［７］ 式（Ｉａ）で表される化合物。

［式（Ｉａ）中、
Ｒ^1a及びＲ^2aは、互いに独立に、オルト位或いはメタ位に炭素数１～２０の炭化水素基を置換基として有するフェニル基、又はパラ位に炭素数５～２０の炭化水素基を置換基として有するフェニル基を表す。
Ｒ^3a、Ｒ^6a及びＲ^8aは、互いに独立に、置換基を有してもよい炭素数１～３０の炭化水素基、置換基を有してもよい炭素数１～３０の芳香族複素環基、又はこれらを組み合わせた基を表す。
Ｒ^4a、Ｒ^5a、Ｒ^7a及びＲ^9aは、互いに独立に、水素原子、－Ｒ^11a、－Ｏ－Ｒ^11a、－ＣＯ－Ｏ－Ｒ^11a、ハロゲン原子、ヒドロキシ基、カルボキシ基又はニトロ基を表す。
Ｒ^11aは、置換基を有してもよい炭素数１～３０の炭化水素基を表し、Ｒ^11aが複数ある場合、それらは互いに同じでも異なっていてもよい。］ The gist of the present invention is as follows.
[1] A composition comprising a colorant and a resin,
A colored resin composition, wherein the colorant comprises a compound represented by formula (I).

[In formula (I),
R ¹ and R ² each independently represent an aryl group having 6 to 20 carbon atoms which may have a substituent, or a heteroaryl group having 1 to 20 carbon atoms which may have a substituent.
^R3 , ^R6 , and ^R8 each independently represent a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, an aromatic heterocyclic group having 1 to 30 carbon atoms which may have a substituent, or a combination thereof.
R ⁴ , R ⁵ , R ⁷ and R ⁹ each independently represent a hydrogen atom, --R ¹¹ , --O--R ¹¹ , --CO--O--R ¹¹ , a halogen atom, a hydroxy group, a carboxy group or a nitro group.
R ¹¹ represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and when there are a plurality of R ¹¹ 's, they may be the same or different.
[2] The colored resin composition according to [1], wherein the colorant further contains a perylene compound.
[3] The colored resin composition according to [1] or [2], further comprising a polymerizable compound and a polymerization initiator.
[4] The colored resin composition according to any one of [1] to [3], further comprising a solvent.
[5] A color filter formed from the colored resin composition according to any one of [1] to [4].
[6] A display device comprising the color filter according to [5].
[7] A compound represented by formula (Ia):

[In the formula (Ia),
R ^1a and R ^2a each independently represent a phenyl group having a hydrocarbon group having 1 to 20 carbon atoms as a substituent at the ortho- or meta-position, or a phenyl group having a hydrocarbon group having 5 to 20 carbon atoms as a substituent at the para-position.
R ^3a , R ^6a and R ^8a each independently represent a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, an aromatic heterocyclic group having 1 to 30 carbon atoms which may have a substituent, or a combination thereof.
R ^4a , R ^5a , R ^7a and R ^9a each independently represent a hydrogen atom, --R ^11a , --O--R ^11a , --CO--O--R ^11a , a halogen atom, a hydroxy group, a carboxy group or a nitro group.
R ^11a represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent, and when there are a plurality of R ^11a , they may be the same or different.]

According to the present invention, it is possible to provide a colored resin composition and a compound that can be used to form a color filter having superior light resistance compared to conventional colored resin compositions containing a perylene compound as a colorant.

<Colored resin composition>
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 may be used alone or in combination of two or more kinds, unless otherwise specified.

<Colorant (A)>
The colorant (A) contains a compound represented by formula (I) (hereinafter, may be referred to as compound (I)).

［式（Ｉ）中、
Ｒ¹及びＲ²は、互いに独立に、置換基（Ａ２）を有していてもよい炭素数６～２０のアリール基又は置換基（Ａ２）を有していてもよい炭素数１～２０のヘテロアリール基を表す。
Ｒ³、Ｒ⁶及びＲ⁸は、互いに独立に、置換基（Ａ１）を有してもよい炭素数１～３０の炭化水素基、置換基（Ａ１）を有してもよい炭素数１～３０の芳香族複素環基、又はこれらを組み合わせた基を表す。
Ｒ⁴、Ｒ⁵、Ｒ⁷及びＲ⁹は、互いに独立に、水素原子、－Ｒ¹¹、－Ｏ－Ｒ¹¹、－ＣＯ－Ｏ－Ｒ¹¹、ハロゲン原子、ヒドロキシ基、カルボキシ基又はニトロ基を表す。
Ｒ¹¹は、置換基（Ａ１）を有してもよい炭素数１～３０の炭化水素基を表し、Ｒ¹¹が複数ある場合、それらは互いに同じでも異なっていてもよい。］ <<Compound (I)>>

[In formula (I),
R ¹ and R ² each independently represent an aryl group having 6 to 20 carbon atoms which may have a substituent (A2) or a heteroaryl group having 1 to 20 carbon atoms which may have a substituent (A2).
^R3 , ^R6 , and ^R8 each independently represent a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent (A1), an aromatic heterocyclic group having 1 to 30 carbon atoms which may have a substituent (A1), or a combination thereof.
R ⁴ , R ⁵ , R ⁷ and R ⁹ each independently represent a hydrogen atom, --R ¹¹ , --O--R ¹¹ , --CO--O--R ¹¹ , a halogen atom, a hydroxy group, a carboxy group or a nitro group.
R ¹¹ represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent (A1), and when there are a plurality of R ¹¹ 's, they may be the same or different from each other.

Examples of the aryl group having 6 to 20 carbon atoms represented by ^R1 and ^R2 include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a phenanthryl group, an anthryl group, a pyrenyl group, etc. The number of carbon atoms of the aryl group is preferably 6 to 15, more preferably 6 to 10, and further preferably a phenyl group.

Examples of the heteroaryl group having 1 to 20 carbon atoms represented by ^R1 and ^R2 include a furyl group, a pyrrolyl group, a thienyl group, an oxazolyl group, a pyridyl group, a quinolinyl group, a thiazolyl group, a benzothiazolyl group, a carbazolyl group, etc. The number of carbon atoms in the heteroaryl group is preferably 2 to 20, more preferably 3 to 15, and even more preferably 3 to 12.

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

The above halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. From the viewpoint of synthesis, chlorine atoms and bromine atoms are preferred, and chlorine atoms are more preferred.

From the viewpoint of improving the light resistance of the obtained color filter, the aryl group having 6 to 20 carbon atoms or the heteroaryl group having 1 to 20 carbon atoms represented by R ¹ and R ² preferably has a substituent (A2). The substituent (A2) is preferably a halogen atom, an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an alkenyl group having 2 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, an aralkyl group having 7 to 20 carbon atoms, or an arylalkenyl group having 8 to 20 carbon atoms, more preferably a halogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, even more preferably a halogen atom, an alkyl group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 20 carbon atoms, even more preferably a chlorine atom, a bromine atom, an alkyl group having 1 to 10 carbon atoms, or an aralkyl group having 7 to 15 carbon atoms, and even more preferably a chlorine atom, an alkyl group having 1 to 5 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms.

When the aryl group having 6 to 20 carbon atoms or the heteroaryl group having 1 to 20 carbon atoms represented by R ¹ and R ² has a substituent (A2), the number of the substituents (A2) is not limited and may be 1 or 2 or more, preferably 1 or 2, and more preferably 1. When multiple substituents (A2) are present, they may be the same or different.

It is preferable that R ¹ and R ² each independently represent an aryl group which may have a substituent (A2).

When the aryl group having 6 to 20 carbon atoms represented by ^R1 and ^R2 is a phenyl group, the substituent (A2) may be located at any of the ortho-, para-, or meta-positions, and is preferably located at the ortho- or para-position.

Specific examples of the aryl group having 6 to 20 carbon atoms which may have a substituent (A2) represented by ^R1 and ^R2 include groups represented by the following formulae (F-1) to (F-15), in which * represents a bond.

From the viewpoint of improving the light resistance of the obtained color filter, R ¹ and R ² are preferably, independently, a group represented by any one of the above formulas (F-1) to (F-15), and more preferably a group represented by any one of formulas (F-5), (F-9) and (F-13).
From the viewpoint of improving the solubility of compound (I) in a solvent, R ¹ and R ² are preferably groups that can cause steric hindrance, and are each independently preferably a phenyl group having at least one branched alkyl group, such as an isopropyl group, a (1-ethyl)propyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group, or an aralkyl group having a branched structure, such as an α-methylbenzyl group, an α,α-dimethylbenzyl group, an α-methylphenethyl group, or an α,α-dimethylphenethyl group, as a substituent (A2), and are further preferably a group represented by any of the above formulas (F-5), (F-6), (F-12), (F-13), or (F-15).
It is also preferable that R ¹ and R ² are the same group.

The hydrocarbon group having 1 to 30 carbon atoms represented by R ³ , R ⁶ , R ⁸ and R ¹¹ includes an aliphatic hydrocarbon group and an aromatic hydrocarbon group. The aliphatic hydrocarbon group may be saturated or unsaturated, and may be linear or alicyclic.

Examples of the saturated or unsaturated chain hydrocarbon group represented by R ³ , R ⁶ , R ⁸ and R ¹¹ include straight-chain 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, (1-ethyl)butyl, (2-ethyl)butyl, (1-propyl)butyl, isopentyl, neopentyl, tert-pentyl, (2-methyl)pentyl, (1-ethyl)pentyl, branched alkyl groups such as a (3-ethyl)pentyl group, a (1-propyl)pentyl group, a (1-butyl)pentyl group, an isohexyl group, a (5-methyl)hexyl group, a (2-ethyl)hexyl group, a (1-butyl)hexyl group, a (1-pentyl)hexyl group, a (3-ethyl)heptyl group, a (1-hexyl)heptyl group, a (1-heptyl)octyl group, and a (1-octyl)nonyl group; alkenyl groups such as a vinyl group, a 1-propenyl group, a 2-propenyl group (allyl group), a (1-methyl)ethenyl 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 25, more preferably 1 to 20, and even more preferably 1 to 15. The number of carbon atoms in the unsaturated chain hydrocarbon group is preferably 2 to 25, more preferably 2 to 20, and even more preferably 2 to 15.

Examples of the saturated or unsaturated alicyclic hydrocarbon group represented by R ³ , R ⁶ , R ⁸ , and R ¹¹ include cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, and cyclooctyl group; cycloalkenyl groups such as cyclohexenyl group (e.g., cyclohex-2-ene, cyclohex-3-ene), cycloheptenyl group, and cyclooctenyl group; norbornyl group, adamantyl group, and bicyclo[2.2.2]octyl group. The number of carbon atoms in the saturated or unsaturated alicyclic hydrocarbon group is preferably 3 to 25, more preferably 3 to 20, and even more preferably 3 to 15.

Examples of the aromatic hydrocarbon group represented by ^R3 , ^R6 , ^R8 , and ^R11 include a phenyl group, a 1-naphthyl group, a 2-naphthyl group, a phenanthryl group, an anthryl group, a pyrenyl group, etc. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 25, more preferably 6 to 20, and even more preferably 6 to 15.

The hydrocarbon groups represented by ^R3 , ^R6 , ^R8 , and ^R11 may be groups in which two or more of the chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups listed above are combined, so long as the upper limit of the carbon number is not more than 30. Such groups may be, for example, groups in which an aromatic hydrocarbon group is combined with at least one group selected from a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group, and in such a combined hydrocarbon group, the chain hydrocarbon group may be combined as a divalent group (for example, an alkanediyl group). Examples of the combined hydrocarbon groups include aralkyl groups such as benzyl, phenethyl, and 1-methyl-1-phenylethyl; arylalkenyl groups such as phenylethenyl (phenylvinyl); arylalkynyl groups such as phenylethynyl; o-tolyl, m-tolyl, p-tolyl, 2-ethylphenyl, 3-ethylphenyl, 4-ethylphenyl, 2,3-dimethylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, and 3,5-dimethylphenyl. nyl group, 2,4,6-trimethylphenyl group, 4-vinylphenyl group, o-isopropylphenyl group, m-isopropylphenyl group, p-isopropylphenyl group, 2,3-diisopropylphenyl group, 2,4-diisopropylphenyl group, 2,5-diisopropylphenyl group, 2,6-diisopropylphenyl group, 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(te alkylaryl groups such as 2,3-dihydro-4-indenyl group, 1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 8-methyl-1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 9-methyl-1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 10-methyl-1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 11-methyl-1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 12-methyl-1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 13-methyl-1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 14-methyl-1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 15-methyl-1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 16-methyl-1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 17-methyl-1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 18-methyl-1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 19-methyl-1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 20-methyl-1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 21-methyl-1,2,3,5,6,7-hexahydro-4-s-indacenyl group, 22-methyl-1,2,3,5,6,7- Examples of such aryl groups include aryl groups having an alkanediyl group bonded thereto, such as a hexahydro-4-s-indacenyl group, a 5,6,7,8-tetrahydro-1-naphthyl group, a 5,6,7,8-tetrahydro-2-naphthyl group, a 3-methyl-5,6,7,8-tetrahydro-2-naphthyl group, or a 3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl group; an aryl group having one or more aryl groups bonded thereto, such as a biphenylyl group or a terphenylyl group; a cyclohexylmethylphenyl group, a benzylphenyl group, or a (dimethyl(phenyl)methyl)phenyl group. The hydrocarbon group may be, for example, a hydrocarbon group formed by combining a chain hydrocarbon group and an alicyclic hydrocarbon group, and examples thereof include a 1-methylcyclopropyl group, a 1-methylcyclohexyl group, a 2-methylcyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 1,2-dimethylcyclohexyl group, a 1,3-dimethylcyclohexyl group, a 1,4-dimethylcyclohexyl group, a 2,3-dimethylcyclohexyl group, a 2,4-dimethylcyclohexyl group, a 2,5-dimethylcyclohexyl group, a 2,6-dimethylcyclohexyl group, a 3,4-dimethylcyclohexyl group, a 3,5-dimethylcyclohexyl group, a 2,2-dimethylcyclohexyl group, a 3,3-dimethylcyclohexyl group, and the like. and alkyl groups having one or more alicyclic hydrocarbon groups bonded thereto, such as a cyclopropylmethyl group, a cyclopropylethyl group, a cyclobutylmethyl group, a cyclobutylethyl group, a cyclopentylmethyl group, a cyclopentylethyl group, a cyclohexylmethyl group, a 2-methylcyclohexylmethyl group, a cyclohexylethyl group, and an adamantylmethyl group. The number of carbon atoms in the group consisting of two or more chain hydrocarbon groups, alicyclic hydrocarbon groups, and aromatic hydrocarbon groups is preferably 4 to 28, more preferably 6 to 25, and even more preferably 8 to 20. Among these, a group in which an aromatic hydrocarbon group and a chain hydrocarbon group are combined is preferred, and an alkylaryl group is more preferred.

Examples of the aromatic heterocyclic group having 1 to 30 carbon atoms represented by ^R3 , ^R6 , and ^R8 include aromatic heterocyclic groups containing at least one heteroatom such as a nitrogen atom, an oxygen atom, or a sulfur atom. Specific examples of the aromatic heterocyclic group include a furyl group, a pyrrolyl group, a thienyl group, an oxazolyl group, a pyridyl group, a quinolinyl group, a thiazolyl group, a benzothiazolyl group, and a carbazolyl group. The number of carbon atoms in the aromatic heterocyclic group is preferably 2 to 25, more preferably 3 to 20, and even more preferably 3 to 15.

The combined group formed by the combination of the hydrocarbon group represented by R ³ , R ⁶ and R ⁸ with the aromatic heterocyclic group may be a group in which two or more of the above-mentioned hydrocarbon groups and aromatic heterocyclic groups are combined, for example, a group in which at least one selected from a chain hydrocarbon group, an alicyclic hydrocarbon group and an aromatic hydrocarbon group is combined with an aromatic heterocyclic group, and in the group formed by the combination, the chain hydrocarbon group may be combined as a divalent group (for example, an alkanediyl group). Examples of the group formed by the combination of the hydrocarbon group and the aromatic heterocyclic group include a 2-methylpyridinyl group, a 4-ethyl-2-methylpyridinyl group, an indole group, a benzimidazole group, a benzofuran group, and a benzothiophene group. The number of carbon atoms in the group formed by the combination of the hydrocarbon group and the aromatic heterocyclic group is preferably 4 to 30, more preferably 6 to 30, and even more preferably 10 to 30.

Hydrocarbon groups having 1 to 30 carbon ^atoms represented by R ³ , R ⁶ , R ⁸ and R ^{11 , and} Examples of the substituent (A1) which the aromatic heterocyclic group having 1 to 30 carbon atoms represented by formula ( ⁸ ) may have include, for example, a halogen atom; a nitrile group; a nitro group; an amino group; a hydroxy group; an alkoxy group having 1 to 20 carbon atoms, such as a methoxy group or an ethoxy group; an aryloxy group having 6 to 20 carbon atoms, such as a phenyloxy group, a 1-naphthyloxy group or a 2-naphthyloxy group; a thiol group; an alkylthio group having 1 to 20 carbon atoms, such as a methylthio group or an ethylthio group; an allylthio group; an arylthio group having 6 to 20 carbon atoms, such as a phenylthio group, a 1-naphthylthio group or a 2-naphthylthio group; a sulfoxy group; an alkylsulfoxy group having 1 to 20 carbon atoms, such as a methylsulfoxy group or an ethylsulfoxy group; an arylsulfoxy group having 6 to 20 carbon atoms, such as a phenylsulfoxy group, a 1-naphthylsulfoxy group or a 2-naphthylsulfoxy group; a silyl group; a boryl group; and a monomethylamino group. arylamino groups having 6 to 20 carbon atoms, such as a monophenylamino group, a diphenylamino group, or a triphenylamino group; aralkylamino groups having 7 to 20 carbon atoms, such as a benzylamino group; a carboxy group; a carbamoyl group; alkylcarbonyl groups having 2 to 20 carbon atoms, such as an acetyl group or a propionyl group; arylcarbonyl groups having 7 to 20 carbon atoms, such as a benzoyl group, a 1-naphthylcarbonyl group, or a 2-naphthylcarbonyl group; alkoxycarbonyl groups having 2 to 20 carbon atoms, such as a methoxycarbonyl group or an ethoxycarbonyl group; and aryloxycarbonyl groups having 7 to 20 carbon atoms, such as a phenyloxycarbonyl group, a 1-naphthyloxycarbonyl group, or a 2-naphthyloxycarbonyl group.

The above halogen atoms include fluorine atoms, chlorine atoms, bromine atoms, and iodine atoms. From the viewpoint of synthesis, chlorine atoms and bromine atoms are preferred.

Specific examples of the hydrocarbon group having 1 to 30 carbon atoms which may have a substituent (A1) represented by R ³ , R ⁶ , R ⁸ and R ¹¹ include groups represented by the following formulae (D-1) to (D-14) and (G-1) to (G-24), in which * represents a bond.

From the viewpoint of improving the light resistance of the obtained color filter, it is preferable that R ³ , R ⁶ and R ⁸ are each independently an aromatic hydrocarbon group which may have a substituent (A1), or a group which combines an aromatic hydrocarbon group which may have a substituent (A1) with a chain-like hydrocarbon group, more preferably a group which combines an aromatic hydrocarbon group which may have a substituent (A1) with a chain-like hydrocarbon group, even more preferably a group which combines an aromatic hydrocarbon group with a chain-like hydrocarbon group, still more preferably a group which combines an aromatic hydrocarbon group with a saturated chain-like hydrocarbon group, and even more preferably a group which combines an aromatic hydrocarbon group having 6 to 12 carbon atoms with a saturated chain-like hydrocarbon group having 1 to 8 carbon atoms. Specifically, R ³ , R ⁶ and R ⁸ are each preferably, independently, a group represented by any one of the above formulas (G-1) to (G-24), more preferably a group represented by any one of the formulas (G-1) to (G-15), even more preferably a group represented by any one of the formulas (G-5) to (G-15), still more preferably a group represented by any one of the formulas (G-5) to (G-9), (G-12) or (G-14), and particularly preferably a group represented by formula (G-8).
Furthermore, it is preferable that two or more of R ³ , R ⁶ and R ⁸ are the same group, it is more preferable that R ³ and R ⁶ are the same group, and it is even more preferable that all three are the same group.

Examples of -O- ^R11 represented by ^R4 , ^R5 , ^R7 , and ^R9 include oxy groups having the above-mentioned ^R11 , such as alkoxy groups having 1 to 30 carbon atoms and aryloxy groups having 1 to 30 carbon atoms. Specific examples include methoxy groups, ethoxy groups, propoxy groups, butoxy groups, pentyloxy groups, phenoxy groups, and naphthyloxy groups.

Examples of -CO-O- ^R11 represented by ^R4 , ^R5 , ^R7 and ^R9 include oxycarbonyl groups having the above-mentioned ^R11 , such as alkoxycarbonyl groups having 1 to 30 carbon atoms and aryloxycarbonyl groups having 1 to 30 carbon atoms. Specific examples thereof include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a sec-butoxycarbonyl group, a tert-butoxycarbonyl group, a butoxycarbonyl group, a pentyloxycarbonyl group, a (1-ethyl)pentyloxycarbonyl group, a hexyloxycarbonyl group, a (2-ethyl)hexyloxycarbonyl group, a heptyloxycarbonyl group, a (1-butyl)heptyloxycarbonyl group, an octyloxycarbonyl group, a (1-heptyl)octyloxycarbonyl group, a nonyloxycarbonyl group, a decyloxycarbonyl group, an undecyloxycarbonyl group, a dodecyloxycarbonyl group, a phenyloxycarbonyl group, and an icosyloxycarbonyl group.

Examples of the halogen atom represented by R ⁴ , R ⁵ , R ⁷ and R ⁹ include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

From the viewpoint of synthesis, R ⁴ , R ⁵ , R ⁷ and R ⁹ are preferably hydrogen atoms. R ⁴ , R ⁵ , R ⁷ and R ⁹ may be appropriately combined to provide a compound having a desired absorption wavelength or fluorescence wavelength.

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

In Table 1, H represents a hydrogen atom, and F-1, F-4, F-5, F-9, F-10, F-13, G-5, G-8, and G-14 represent groups represented by the above formulas (F-1), (F-4), (F-5), (F-9), (F-10), (F-13), (G-5), (G-8), and (G-14), respectively.

From the viewpoint of improving the light resistance of the resulting color filter, as compound (I), compounds (I-1) to (I-18) are preferred, compounds (I-7) to (I-12) are more preferred, and compounds (I-9), (I-10) and (I-12) are even more preferred.

Compound (I) is preferably a compound represented by formula (Ia) (hereinafter, sometimes referred to as compound (Ia)).

［式（Ｉａ）中、
Ｒ^1a及びＲ^2aは、互いに独立に、オルト位或いはメタ位に炭素数１～２０の炭化水素基を置換基として有するフェニル基、又はパラ位に炭素数５～２０の炭化水素基を置換基として有するフェニル基を表す。
Ｒ^3a、Ｒ^6a及びＲ^8aは、互いに独立に、置換基（Ａ５）を有してもよい炭素数１～３０の炭化水素基、置換基（Ａ５）を有してもよい炭素数１～３０の芳香族複素環基、又はこれらを組み合わせた基を表す。
Ｒ^4a、Ｒ^5a、Ｒ^7a及びＲ^9aは、互いに独立に、水素原子、－Ｒ^11a、－Ｏ－Ｒ^11a、－ＣＯ－Ｏ－Ｒ^11a、ハロゲン原子、ヒドロキシ基、カルボキシ基又はニトロ基を表す。
Ｒ^11aは、置換基（Ａ５）を有してもよい炭素数１～３０の炭化水素基を表し、Ｒ^11aが複数ある場合、それらは互いに同じでも異なっていてもよい。］ <<Compound (Ia)>>

[In formula (Ia),
R ^1a and R ^2a each independently represent a phenyl group having a hydrocarbon group having 1 to 20 carbon atoms as a substituent at the ortho- or meta-position, or a phenyl group having a hydrocarbon group having 5 to 20 carbon atoms as a substituent at the para-position.
R ^3a , R ^6a and R ^8a each independently represent a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent (A5), an aromatic heterocyclic group having 1 to 30 carbon atoms which may have a substituent (A5), or a combination thereof.
R ^4a , R ^5a , R ^7a and R ^9a each independently represent a hydrogen atom, --R ^11a , --O--R ^11a , --CO--O--R ^11a , a halogen atom, a hydroxy group, a carboxy group or a nitro group.
R ^11a represents a hydrocarbon group having 1 to 30 carbon atoms which may have a substituent (A5), and when there are a plurality of R ^11a , they may be the same or different.]

Examples of the hydrocarbon group having 1 to 20 carbon atoms which the phenyl group represented by R ^1a and R ^2a has as a substituent at the ortho or meta position include the same examples as the hydrocarbon group represented by R ³ , R ⁶ , R ⁸ and R ¹¹ , except that examples having 21 or more carbon atoms are not included. The number of carbon atoms in the hydrocarbon group is preferably 1 to 15, more preferably 1 to 10, even more preferably 1 to 7, and even more preferably 1 to 5. From the viewpoint of improving the light resistance and solubility in solvents of the resulting color filter, the hydrocarbon group is preferably a saturated or unsaturated chain hydrocarbon group, more preferably a saturated chain hydrocarbon group, and even more preferably a branched alkyl group such as an isopropyl group, a (1-ethyl)propyl group, an isobutyl group, a sec-butyl group or a tert-butyl group.

Examples of the hydrocarbon group having 5 to 20 carbon atoms which the phenyl group represented by R ^1a and R ^2a has as a substituent at the para position include the same examples as the hydrocarbon groups represented by R ³ , R ⁶ , R ⁸ and R ¹¹ , except that examples having 4 or less carbon atoms or 21 or more carbon atoms are not included. The number of carbon atoms in the hydrocarbon group is preferably 5 to 15, more preferably 7 to 15, and even more preferably 7 to 13. From the viewpoint of improving the light resistance and solubility in a solvent of the resulting color filter, the hydrocarbon group is preferably a group in which two or more of a chain hydrocarbon group, an alicyclic hydrocarbon group, and an aromatic hydrocarbon group are combined, more preferably a group in which a chain hydrocarbon group and an aromatic hydrocarbon group are combined, still more preferably an aralkyl group such as a benzyl group, a phenethyl group, an α-methylbenzyl group, an α,α-dimethylbenzyl group, an α-methylphenethyl group, or an α,α-dimethylphenethyl group, and even more preferably an aralkyl group having a branched chain structure such as an α-methylbenzyl group, an α,α-dimethylbenzyl group, an α-methylphenethyl group, or an α,α-dimethylphenethyl group.

The number of substituents possessed by the phenyl group represented by R ^1a and R ^2a is not limited, and may be 1 or 2 or more, preferably 1 to 2, and more preferably 1. When multiple substituents are possessed, they may be the same as or different from each other, and as long as the phenyl group has a hydrocarbon group having 1 to 20 carbon atoms as a substituent at the ortho-position or the meta-position or a hydrocarbon group having 5 to 20 carbon atoms as a substituent at the para-position, examples of the other substituents that may be possessed include the same examples as those of the above-mentioned substituent (A2).

It is preferable that R ^1a and R ^2a are the same group.

Examples of the hydrocarbon group having 1 to 30 carbon atoms represented by R ^3a , R ^6a , R ^8a and R ^11a include the same as the hydrocarbon groups represented by R ³ , R ⁶ , R ⁸ and R ¹¹ , and the preferred range of the number of carbon atoms is also the same.

Examples of the aromatic heterocyclic group having 1 to 30 carbon atoms represented by R ^3a , R ^6a and R ^8a include the same as those of the aromatic heterocyclic group represented by R ³ , R ⁶ and R ⁸ , and the preferred range of the number of carbon atoms is also the same.

Examples of the groups formed by combining the hydrocarbon groups represented by ^R3a , ^R6a , and ^R8a with the aromatic heterocyclic groups include the same examples as the groups formed by combining the hydrocarbon groups represented by ^R3 , ^R6 , and ^R8 with the aromatic heterocyclic groups, and the preferred range of carbon numbers is also the same.

Examples of the substituent (A5) which may be possessed by the hydrocarbon group having 1 to 30 carbon atoms represented by R ^3a , R ^6a , R ^8a , and R ^11a , and the aromatic heterocyclic group having 1 to 30 carbon atoms represented by R ^3a , R ^6a , and R ^8a , include the same examples as those of the substituent (A1).

From the viewpoint of improving the light fastness of the obtained color filter, it is preferable that R ^3a , R ^6a and R ^8a are each independently an aromatic hydrocarbon group which may have a substituent (A5), or a group which combines an aromatic hydrocarbon group which may have a substituent (A5) with a chain-like hydrocarbon group, it is more preferable that they are a group which combines an aromatic hydrocarbon group which may have a substituent (A5) with a chain-like hydrocarbon group, it is even more preferable that they are a group which combines an aromatic hydrocarbon group with a chain-like hydrocarbon group, it is even more preferable that they are a group which combines an aromatic hydrocarbon group with a saturated chain-like hydrocarbon group, it is even more preferable that they are a group which combines an aromatic hydrocarbon group having 6 to 12 carbon atoms with a saturated chain-like hydrocarbon group having 1 to 8 carbon atoms, and it is particularly preferable that they are an alkylaryl group having 8 to 20 carbon atoms. Specifically, R ^3a , R ^6a , and R ^8a are each preferably, independently, a group represented by any one of the above formulas (G-1) to (G-24), more preferably a group represented by any one of the formulas (G-1) to (G-15), even more preferably a group represented by any one of the formulas (G-5) to (G-15), still more preferably a group represented by any one of the formulas (G-5) to (G-9), (G-12) or (G-14), and particularly preferably a group represented by formula (G-8).
It is preferable that two or more of R ^3a , R ^6a and R ^8a are the same group, it is more preferable that R ^3a and R ^6a are the same group, and it is even more preferable that all three are the same group.

Examples of --O--R ^11a represented by R ^4a , R ^5a , R ^7a and R ^9a include the same as those of --O--R ¹¹ represented by R ⁴ , R ⁵ , R ⁷ and R ⁹ .

Examples of --CO--O--R ^11a represented by R ^4a , R ^5a , R ^7a and R ^9a include the same as those of --CO--O--R ¹¹ represented by R ⁴ , R ⁵ , R ⁷ and R ⁹ .

Examples of the halogen atoms represented by R ^4a , R ^5a , R ^7a and R ^9a include the same as those of the halogen atoms represented by R ⁴ , R ⁵ , R ⁷ and R ⁹ .

From the viewpoint of synthesis, R ^4a , R ^5a , R ^7a and R ^9a are preferably hydrogen atoms. R ^4a , R ^5a , R ^7a and R ^9a may be appropriately combined to form a compound having a desired absorption wavelength or fluorescence wavelength.

Compound (I) can be produced, for example, by reacting a compound represented by the following formula (pt1) with a chlorinating agent to produce a compound represented by the following formula (pt2), reacting the compound represented by formula (pt2) with compounds represented by the following formulas (MA1), (MA2) and (MA3) in a solvent to produce a compound represented by the following formula (pt3), and further reacting the compound represented by formula (pt3) with compounds represented by the following formulas (MA4) and (MA5) in a solvent.

［式中、Ｒ¹～Ｒ⁹は、上述の定義と同一である。］

[wherein R ¹ to R ⁹ are the same as defined above.]

Examples of compounds represented by formula (pt1) include benzo[ghi]perylene-1,2,4,5,10,11-hexacarboxylic acid trianhydride.

The chlorinating agent is an agent that substitutes hydrogen atoms of a six-membered ring compound with chlorine atoms. Preferred chlorinating agents are chlorine, N-chlorosuccinimide, cyanuric acid chloride, N-chlorophthalimide, 1,3-dichloro-5,5-dimethylhydantoin, trichloroisocyanuric acid, and chlorosulfonic acid, more preferred are chlorine and chlorosulfonic acid, and even more preferred is chlorosulfonic acid.

The amount of the chlorinating agent used is usually 1 mole or more and 1,000 moles or less, preferably 1 mole or more and 600 moles or less, more preferably 1 mole or more and 400 moles or less, and even more preferably 1 mole or more and 200 moles or less, relative to 1 mole of the compound represented by formula (pt1).

Examples of the compounds represented by formula (MA1), formula (MA2) and formula (MA3) include 2,6-diisopropylaniline.
The total amount of the compounds represented by formula (MA1), formula (MA2) and formula (MA3) used is usually 3 mol or more and 20 mol or less, preferably 3 mol or more and 10 mol or less, and more preferably 3 mol or more and 8 mol or less, relative to 1 mol of the compound represented by formula (pt2).

Examples of the compounds represented by formula (MA4) and formula (MA5) include 4-chlorophenol, 2-isopropylphenol, and 4-α-cumylphenol.
The total amount of the compounds represented by formula (MA4) and formula (MA5) used is usually 1 mole or more and 20 moles or less, preferably 1 mole or more and 15 moles or less, and more preferably 1 mole or more and 10 moles or less, relative to 1 mole of the compound represented by formula (pt3). There is no limitation on the order in which the compounds represented by formula (MA4) and formula (MA5) are reacted with the compound represented by formula (pt3), and they may be reacted simultaneously.

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

The amount of the solvent used is usually 1 to 1000 parts by mass per part by mass of the compound represented by formula (pt2) when the compound represented by formula (pt2) is reacted with the compounds represented by formula (MA1), formula (MA2) and formula (MA3), and is usually 1 to 1000 parts by mass per part by mass of the compound represented by formula (pt3) when the compound represented by formula (pt3) is reacted with the compounds represented by formula (MA4) and formula (MA5).

The reaction of the compound represented by formula (pt1) with a chlorinating agent may be carried out in the presence of a catalyst.
The catalyst includes, for example, bromine, iodine, etc., with iodine being preferred.
When the reaction is carried out in the presence of a catalyst, the amount of the catalyst used is usually 0.01 mol or more and 0.99 mol or less, and preferably 0.1 mol or more and 0.5 mol or less, relative to 1 mol of the compound represented by formula (pt1).

The reaction of the compound represented by formula (pt3) with the compounds represented by formula (MA4) and formula (MA5) may be carried out in the presence of a base.
The base may be an organic base or an inorganic base, preferably an inorganic base, such as sodium hydrogen carbonate, potassium hydrogen carbonate, sodium carbonate, potassium carbonate, lithium hydroxide, sodium hydroxide, potassium hydroxide, etc., preferably potassium carbonate.
When the reaction is carried out in the presence of a base, the amount of the base used is usually 0.1 mol or more and 100 mol or less, and preferably 1 mol or more and 40 mol or less, relative to 1 mol of the compound represented by formula (pt2).

The reaction time when reacting the compound represented by formula (pt1) with the chlorinating agent is usually 0.25 hours to 500 hours, the reaction time when reacting the compound represented by formula (pt2) with the compounds represented by formulas (MA1), (MA2) and (MA3) is usually 0.5 hours to 500 hours, and the reaction time when reacting the compound represented by formula (pt3) with the compounds represented by formulas (MA4) and (MA5) is usually 0.5 hours to 500 hours.

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

Compound (I) has high solubility in solvents such as propylene glycol monomethyl ether acetate and cyclohexane (particularly propylene glycol monomethyl ether acetate), and has good solubility. The solubility can be calculated by weighing about 50 mg of the compound to be measured for solubility (hereinafter, sometimes referred to as solute) in a 20 mL screw tube, adding about 500 mg of solvent thereto, weighing the total amount of solute and solvent, stirring with a mix rotor for 30 minutes, and when dissolution is confirmed by visual observation, the mass of solute relative to the total mass of solute and solvent can be calculated from the following formula (i). When dissolution is not confirmed by visual observation, the solvent is added in 500 mg increments until dissolution occurs, stirring with a mix rotor for 30 minutes each time, and the mass of solute relative to the total mass of solute and solvent when dissolution is confirmed by visual observation can be calculated from the following formula (i).
Solubility (%) = (mass of solute) / (total mass of solute and solvent) × 100 (i)

The solubility of compound (I) in propylene glycol monomethyl ether acetate at 20°C is preferably 1.0% by mass or more, more preferably 2.0% by mass or more, even more preferably 2.5% by mass or more, and even more preferably 3.0% by mass or more, and may be 10% by mass or less.

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

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

［式（ＩＩ）中、
Ａｒ²¹～Ａｒ²⁶は、互いに独立に、置換基（Ａ３）を有していてもよい炭素数６～２０のアリール基を表す。
Ｒ²¹～Ｒ²⁴は、互いに独立に、水素原子、置換基（Ａ４）を有していてもよい炭素数１～２０の炭化水素基、ハロゲン原子又はニトロ基を表す。] <<Compound (II)>>

[In the formula (II),
Ar ²¹ to Ar ²⁶ each independently represent an aryl group having 6 to 20 carbon atoms which may have a substituent (A3).
R ²¹ to R ²⁴ each independently represent a hydrogen atom, a hydrocarbon group having 1 to 20 carbon atoms which may have a substituent (A4), a halogen atom, or a nitro group.

The aryl groups represented by Ar ²¹ to Ar ²⁶ each independently include a phenyl group, a naphthyl group, etc., with a phenyl group being preferred.

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

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

The aryl groups represented by Ar ²¹ to Ar ²⁶ may or may not have one or more kinds of substituents (A3).

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

From the viewpoint of solubility in a solvent, Ar ²¹ and Ar ²² are preferably groups represented by any one of formulas (E-5), (E-7), (E-8) and (E-11). From the viewpoint of solubility in a solvent, Ar ²³ to Ar ²⁶ are preferably groups represented by any one of formulas (E-1), (E-4), (E-9), (E-10), (E-17) and (E-18).

Ar ²¹ to Ar ²⁶ may all be the same group or different groups.
It is preferable that Ar ²¹ and Ar ²² are the same group.

Examples of the hydrocarbon groups having 1 to 20 carbon atoms represented by R ²¹ to R ²⁴ include the same examples as the hydrocarbon groups represented by R ³ , R ⁶ , R ⁸ and R ¹¹ above, except that they do not include examples having 21 or more carbon atoms.

Examples of the substituent (A4) which the hydrocarbon group having 1 to 20 carbon atoms represented by R ²¹ to R ²⁴ may have include the same examples as the above-mentioned substituent (A1).

Examples of the halogen atom represented by R ²¹ to R ²⁴ include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

R ²¹ to R ²⁴ are preferably hydrogen atoms.

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

In Table 2, H represents a hydrogen atom, and E-1, E-6, E-7, E-10, E-17, E-18, and E-19 represent groups represented by the above formulas (E-1), (E-6), (E-7), (E-10), (E-17), (E-18), and (E-19), respectively.

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

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

［式中、Ｒ²¹～Ｒ²⁴は、上述の定義と同一である。］

[In the formula, R ²¹ to R ²⁴ are the same as defined above.]

Arx _- ^NH2 (AR1)
^Arx -OH (AR2)
[In the formula, Ar ^x is the same as the definition of Ar ²¹ to Ar ²⁶ above.]

Examples of compounds represented by formula (pt3) include 1,6,7,12-tetrachloroperylene tetracarboxylic dianhydride.

Examples of compounds represented by formula (AR1) include 2,6-diisopropylaniline, aniline, 3,5-dimethylaniline, and 3,5-di-tert-butylaniline. Compounds represented by formula (AR1) may be used alone or in combination of two or more.

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

The total amount of the compound represented by formula (AR1) and the compound represented by formula (AR2) used is usually 1 mole or more and 10 moles or less, preferably 1 mole or more and 8 moles or less, more preferably 1 mole or more and 6 moles or less, and even more preferably 1 mole or more and 4 moles or less, relative to 1 mole of the compound represented by formula (pt3).

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

The amount of the solvent used is usually 1 to 1,000 parts by mass per part by mass of the compound represented by formula (pt3).

The reaction temperature is usually -100°C or higher and 300°C or lower, preferably -90°C or higher and 200°C or lower, and more preferably -10°C or higher and 150°C or lower. The reaction time is usually 0.5 hours to 500 hours.

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

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

When colorant (A) contains a perylene compound, the content of the perylene compound is, for example, 3% by mass or more, preferably 5% by mass or more, more preferably 10% by mass or more, and for example, 95% by mass or less, preferably 90% by mass or less, more preferably 85% by mass or less, based on the total amount of compound (I) and the perylene compound.

When the colorant (A) contains compound (I) and a perylene compound, compound (I) can also be used as a sensitizer for the perylene compound.

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

As long as the dye (A1-1) does not include the compound (I) and the perylene compound, it is not particularly limited and any known dye can be used, such as a solvent dye, an acid dye, a direct dye, or a mordant dye. Examples of the dye include compounds classified as dyes in the Color Index (published by The Society of Dyers and Colourists) and known dyes described in Dyeing Notes (Irosensha). In addition, examples of the dye, based on the chemical structure, include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, nitro dyes, and phthalocyanine dyes. Of these, organic solvent-soluble dyes are preferred.

The pigment (A1-2) is not particularly limited, and any known pigment can be used as long as it does not contain a perylene compound. Examples of the pigment include pigments classified as pigments in the Color Index (published by the Society of Dyers and Colourists).
Examples of pigments classified as C.I. Pigment 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, 73;
red pigments such as C.I. Pigment Red 9, 97, 105, 122, 144, 166, 168, 176, 177, 180, 190, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265, 266, 268, 269, 273;
blue pigments such as C.I. Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 60;
Violet pigments such as C.I. Pigment Violet 1, 19, 23, 32, 36, 38;
green pigments such as C.I. Pigment Green 7, 36, 58, 59, 62, 63;
Brown pigments such as C.I. Pigment Brown 23 and 25;
Black pigments such as C.I. Pigment Black 1 and 7;
Examples include:

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

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

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

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

Colorant (A) can be made to be uniformly dispersed in the solution by adding a dispersant and carrying out a dispersion treatment. When two or more types of colorant (A) are used in combination, each may be dispersed alone, or 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 Co., Ltd.), EFKA (registered trademark) (manufactured by BASF), AJISPER (registered trademark) (manufactured by Ajinomoto Fine-Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by BYK-Chemie Co., Ltd.), and BYK (registered trademark) (manufactured by BYK-Chemie Co., Ltd.). Resin (B), which will be described later, may be used as the dispersant.

When a dispersant is used, the amount of the dispersant (solid content) used is usually 1 part by mass or more and 10,000 parts by mass or less, preferably 5 parts by mass or more and 5,000 parts by mass or less, more preferably 10 parts by mass or more and 3,000 parts by mass or less, and even more preferably 20 parts by mass or more and 1,000 parts by mass or less, per 100 parts by mass of colorant (A). 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.

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

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

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

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

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

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

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

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).

［式（ＢＩ）及び式（ＢＩＩ）中、Ｒ^a及びＲ^bは、互いに独立に、水素原子、又は炭素数１～４のアルキル基を表し、該アルキル基に含まれる水素原子は、ヒドロキシ基で置換されていてもよい。
Ｘ^a及びＸ^bは、互いに独立に、単結合、＊－Ｒ^c－、＊－Ｒ^c－Ｏ－、＊－Ｒ^c－Ｓ－又は＊－Ｒ^c－ＮＨ－を表す。
Ｒ^cは、炭素数１～６のアルカンジイル基を表す。
＊は、Ｏとの結合手を表す。］

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 hydrogen atoms are replaced with hydroxy 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, *-CH ₂ -O-, *-CH ₂ CH ₂ -O-, and more preferably a single bond or *-CH ₂ CH ₂ -O- (* 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 them, compounds represented by formulas (BI-1), (BI-3), (BI-5), (BI-7), (BI-9) and (BI-11) to (BI-15) are preferred, and compounds represented by formulas (BI-1), (BI-7), (BI-9) and (BI-15) are more preferred.

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

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

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

Examples of the monomer (c) include methyl (meth)acrylate, ethyl (meth)acrylate, n-butyl (meth)acrylate, sec-butyl (meth)acrylate, tert-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, dodecyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, cyclopentyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decan-8-yl (meth)acrylate (commonly known in the art as "dicyclopentanyl (meth)acrylate" and sometimes referred to as "tricyclodecyl (meth)acrylate"), tricyclo[5.2.1.0 ^2,6 ]decan-9-yl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 (meth)acrylic acid esters such as 5.2.1.0 ^2,6 ]decen-8-yl(meth)acrylate (commonly known in the art 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;
Halogen atom-containing (meth)acrylic acid esters such as 2,2,3,3,4,4,5,5-octafluoropentyl (meth)acrylate;
dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, and diethyl itaconate;
Bicyclo[2.2.1]hept-2-ene, 5-methylbicyclo[2.2.1]hept-2-ene, 5-ethylbicyclo[2.2.1]hept-2-ene, 5-hydroxybicyclo[2.2.1]hept-2-ene, 5-hydroxymethylbicyclo[2.2.1]hept-2-ene, 5-(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5-methoxybicyclo[2.2.1]hept-2-ene, chloro[2.2.1]hept-2-ene, 5-ethoxybicyclo[2.2.1]hept-2-ene, 5,6-dihydroxybicyclo[2.2.1]hept-2-ene, 5,6-di(hydroxymethyl)bicyclo[2.2.1]hept-2-ene, 5,6-di(2'-hydroxyethyl)bicyclo[2.2.1]hept-2-ene, 5,6-dimethoxybicyclo[2.2.1]hept bicyclounsaturated compounds such as 5-(tert-butoxycarbonyl)bicyclo[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, 5-cyclohexyloxycarbonylbicyclo[2.2.1]hept-2-ene, 5-phenoxycarbonylbicyclo[2.2.1]hept-2-ene, 5,6-bis(tert-butoxycarbonyl)bicyclo[2.2.1]hept-2-ene and 5,6-bis(cyclohexyloxycarbonyl)bicyclo[2.2.1]hept-2-ene;
dicarbonyl imide derivatives such as N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate, and N-(9-acridinyl)maleimide;
Examples of the vinyl group-containing aromatic compounds include styrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, 9-vinylcarbazole, and p-methoxystyrene; vinyl group-containing nitriles such as (meth)acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; vinyl group-containing amides such as (meth)acrylamide; esters such as vinyl acetate; and dienes such as 1,3-butadiene, isoprene, and 2,3-dimethyl-1,3-butadiene.
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.

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

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

The polystyrene-equivalent weight average molecular weight (Mw) of resin (B) is preferably 1,000 to 100,000, more preferably 2,000 to 50,000, and even more preferably 3,000 to 30,000. When the weight average molecular weight is within the above range, the solubility of the unexposed portion in the developer is high, and the resulting pattern tends to have a high residual film rate and hardness.

The dispersity of resin (B) [weight average molecular weight (Mw)/number average molecular weight (Mn)] is preferably 1 or more and 6 or less, more preferably 1 or more and 5 or less, and even more preferably 1 or more and 4 or less.

The acid value (solid content 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 40 mg-KOH/g to 135 mg-KOH/g. Here, the acid value is a value 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 80% by mass, more preferably 10 to 60% by mass, even more preferably 15 to 50% by mass, and even more preferably 15 to 45% by mass, based on 100% by mass of the solid content of the colored resin composition. When the content of resin (B) is within the above range, the unexposed portion tends 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 nonylphenylcarbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexylcarbitol 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 them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, tripentaerythritol octa(meth)acrylate, tripentaerythritol hepta(meth)acrylate, tetrapentaerythritol deca(meth)acrylate, tetrapentaerythritol nona(meth)acrylate, tris(2-(meth)acryloyloxyethyl)isocyanurate, ethyl Examples of the dipentaerythritol hexa(meth)acrylate include ethylene glycol modified pentaerythritol tetra(meth)acrylate, ethylene glycol modified dipentaerythritol hexa(meth)acrylate, propylene glycol modified pentaerythritol tetra(meth)acrylate, propylene glycol modified dipentaerythritol hexa(meth)acrylate, caprolactone modified pentaerythritol tetra(meth)acrylate, and caprolactone modified dipentaerythritol hexa(meth)acrylate, and preferably dipentaerythritol penta(meth)acrylate and dipentaerythritol hexa(meth)acrylate.

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

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

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

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

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 Corporation) may also be used.
Alkylphenone compounds also include 2-hydroxy-2-methyl-1-phenylpropan-1-one, 2-hydroxy-2-methyl-1-[4-(2-hydroxyethoxy)phenyl]propan-1-one, 1-hydroxycyclohexyl phenyl ketone, oligomers of 2-hydroxy-2-methyl-1-(4-isopropenylphenyl)propan-1-one, α,α-diethoxyacetophenone, and benzyl dimethyl ketal.

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, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(alkoxyphenyl)biimidazole, phenyl)-4,4',5,5'-tetra(dialkoxyphenyl)biimidazole, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetra(trialkoxyphenyl)biimidazole (see, for example, JP-B-48-38403 and JP-A-62-174204), and biimidazole compounds in which the phenyl groups at the 4,4',5,5'-positions are substituted with carboalkoxy groups (see, for example, JP-A-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) described below, particularly amines.

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

When the polymerization initiator (D) is contained, the content of the polymerization initiator (D) is preferably 0.01 parts by mass or more and 30 parts by mass or less, and more preferably 0.1 parts by mass or more and 20 parts by mass or less, relative to 100 parts by mass of the total amount of all the resins (B) and the polymerizable compounds (C) contained in the colored resin composition. When the content of the polymerization initiator (D) is within the above range, the sensitivity tends to be increased and the exposure time tends to be shortened, thereby improving the productivity of the color filter.

<Polymerization Initiator Auxiliary Agent (D1)>
The polymerization initiation aid (D1) is a compound used to promote the polymerization of the polymerizable compound (C) whose polymerization has been initiated by the polymerization initiator (D), or a sensitizer. When the polymerization initiation aid (D1) is contained, it is usually used in combination with the polymerization initiator (D).
Examples of the polymerization initiator aid (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds, and carboxylic acid compounds.

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

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.

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

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

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

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, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, 2-ethoxy-2-methylpropionate, Examples of such ether acetates include ethyl acetate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, and dipropylene glycol methyl ether acetate.

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.

Examples of alcohol solvents include methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, and glycerin.

Hydrocarbon solvents include benzene, toluene, xylene, cyclohexane, methylcyclohexane, ethylcyclohexane, normal hexane, styrene, and mesitylene.

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

Two or more of these solvents may be used in combination.

As the solvent, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, cyclohexanone and cyclohexane are preferred, propylene glycol monomethyl ether acetate and cyclohexane are more preferred, and propylene glycol monomethyl ether acetate is more preferred.

When the solvent (E) is contained, the content of the solvent (E) is usually less than 100% by mass, preferably 99.99% by mass or less, more preferably 1% by mass or more and 99.9% by mass or less, even more preferably 10% by mass or more and 99% by mass or less, even more preferably 20% by mass or more and 97% by mass or less, particularly preferably 30% by mass or more and 95% by mass or less, even more preferably 40% by mass or more and 95% by mass or less, and particularly preferably 50% by mass or more and 95% by mass or less. When the content of the solvent (E) is within the above range, the flatness during application is good, and when a color filter is formed, the color density is not insufficient, so that the display characteristics tend to be good.

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

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

Examples of fluorosurfactants include surfactants having a fluorocarbon chain in the molecule. Specific examples include Fluorad (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), EF-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 Asahi Glass Co., Ltd.), and E5844 (manufactured by Daikin Fine Chemicals Research Institute, Ltd.).

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

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

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

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

The film thickness of the color filter to be produced is not particularly limited and can be adjusted as appropriate depending on the purpose and use, and is, for example, preferably 30 μm or less, more preferably 20 μm or less, even more preferably 6 μm or less, and even more preferably 3 μm or less, with no particular lower limit, but usually 0.1 μm or more.

As the substrate, glass plates such as quartz glass, borosilicate glass, alumina silicate glass, and soda lime glass with a silica-coated surface, resin plates such as polycarbonate, polymethylmethacrylate, and polyethylene terephthalate, silicon, and the above substrates on which thin films of aluminum, silver, silver/copper/palladium alloy, etc. are formed can be used. On these substrates, other color filter layers, resin layers, transistors, circuits, etc. may be formed.

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

Next, the colored resin composition layer is exposed through a photomask for forming a desired colored pattern. The pattern on the photomask is not particularly limited, and a pattern according to the intended use is used. As a light source used for exposure, a light source that generates light with a wavelength of 250 nm or more and 450 nm or less is preferable. For example, light less than 350 nm may be cut using a filter that cuts this wavelength range, or light near 436 nm, near 408 nm, and near 365 nm may be selectively extracted using a bandpass filter that extracts these wavelength ranges. Specific examples include mercury lamps, light-emitting diodes, metal halide lamps, halogen lamps, and the like. In addition, it is preferable to use an exposure device (mask aligner) such as a stepper (reduced projection exposure machine) or a proximity exposure machine, since it is possible to uniformly irradiate the entire exposure surface with parallel light rays and to accurately align the photomask with the substrate on which the colored resin composition layer is formed.

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

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

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

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

The present invention will be explained in more detail below with reference to examples. However, the present invention is not limited to the following examples, and it is of course possible to carry out the invention with appropriate modifications within the scope of the above and below-mentioned aims, all of which are included in the technical scope of the present invention. In the following, unless otherwise specified, "parts" means "parts by mass" and "%" means "% by mass."

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
y: tetrahydrofuran Flow rate: 1.0 mL/min Solid content concentration of analytical sample: 0.001 to 0.01% by mass
Injection volume: 50 μL
Detector: RI
Calibration standard material: TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corporation)
The ratio of the weight average molecular weight and the number average molecular weight (Mw/Mn) calculated in terms of polystyrene obtained above was taken as the dispersity.

(Synthesis Example 1)
<Preparation of compound (III)>
The compound represented by the following formula (III) (hereinafter sometimes referred to as compound (III)) was synthesized in accordance with the description in Dyes and Pigments, 2019, Vol. 167, pp. 83-88.

<Identification of Compound (III)>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 1032
Exact Mass: 1031

(Synthesis Example 2)
<Preparation of compound (I-10)>
2.5 parts of compound (III) produced in Synthesis Example 1, 1.7 parts of 4-chlorophenol (manufactured by Tokyo Chemical Industry Co., Ltd.), 2.2 parts of potassium carbonate (manufactured by Kanto Chemical Co., Ltd.), and 100 parts of N-methylpyrrolidone (manufactured by Kanto Chemical Co., Ltd.) were added and stirred at 120°C for 5 hours. While keeping the obtained mixture at 20°C or less, 14 parts of 37% hydrochloric acid (manufactured by Kanto Chemical Co., Ltd.) and 71 parts of water prepared in advance were added, resulting in the formation of a dark red precipitate. The mixture containing this dark red precipitate was filtered, and the residue after filtration was washed with 300 parts of water and 150 parts of methanol. The obtained residue was dried under reduced pressure at 60°C and purified with a silica gel column (solvent: chloroform), to obtain 1.5 parts of a compound represented by formula (I-10) (hereinafter, sometimes referred to as compound (I-10)) (yield 50%).

<Identification of compound (I-10)>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 1216
Exact Mass: 1215

Example 1
<Preparation of compound (I-9)>
Except for changing 1.7 parts of 4-chlorophenol to 1.8 parts of 2-isopropylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Synthesis Example 2 was repeated to obtain 0.66 parts of a compound represented by formula (I-9) (hereinafter, sometimes referred to as compound (I-9)) (yield 22%).

<Identification of compound (I-9)>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 1232
Exact Mass: 1231

Example 2
<Preparation of compound (I-12)>
Except for changing 1.7 parts of 4-chlorophenol to 2.9 parts of 4-cumylphenol (manufactured by Tokyo Chemical Industry Co., Ltd.), the same procedure as in Synthesis Example 2 was repeated to obtain 2.0 parts of a compound represented by formula (I-12) (hereinafter, sometimes referred to as compound (I-12)) (yield 66%).

<Identification of compound (I-12)>
(Mass spectrometry) Ionization mode = ESI+: m/z = [M+H] ⁺ 1384
Exact Mass: 1383

(Synthesis Example 3)
<Preparation of Lumogen® F Yellow 083>
Lumogen (registered trademark) F Yellow 083 represented by the following formula (x) was synthesized according to the description in JP-A-60-203650.

(Synthesis Example 4)
<Preparation of Resin B1>
A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace the atmosphere with nitrogen, 280 parts of propylene glycol monomethyl ether acetate was added, and the mixture was heated to 80°C while 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 having a solid content of 35.1% and a viscosity of 125 mPa·s measured with a Brookfield viscometer (23°C). The weight average molecular weight Mw of the copolymer produced was 9.2×10 ³ , the degree of dispersion was 2.08, and the acid value calculated as solid content was 77 mg-KOH/g. Resin B1 has the following structural units.

Example 3
(1) Solubility test of compound in solvent (propylene glycol monomethyl ether acetate; hereinafter, sometimes referred to as PGMEA) About 50 mg of solute (compound represented by formula (I-10)) was weighed and placed in a 20 mL screw tube. About 500 mg of solvent (PGMEA) was added to this, and the total amount of solute and solvent was weighed. After stirring for 30 minutes with a mix rotor in a thermostatic bath at 20 ° C., if dissolution was confirmed by visual observation, the value calculated from the mass of the solute relative to the total mass of the solute and solvent was taken as the solubility. If dissolution was not confirmed, 500 mg of solvent was added at a time until dissolution occurred, and each time it was added, stirring was continued for 30 minutes with a mix rotor in a thermostatic bath at 20 ° C., and the value calculated from the mass of the solute relative to the total mass of the solute and solvent when dissolution was confirmed by visual observation was taken as the solubility. The results are shown in Table 3.

(2) Preparation of Colored Composition Colored composition 1 was obtained by mixing the components in the following ratio.
(A) Colorant: Compound represented by formula (I-10) 2.6 parts (B) Resin: Resin B1 solution 58 parts (E) Solvent: Propylene glycol monomethyl ether acetate 420 parts

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

(4) Preparation of colored coating film A colored resin composition was applied by spin coating onto a 5 cm square glass substrate (Eagle XG; Corning) so that the film thickness after post-baking was 1.9 to 2.1 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; Topcon Corporation) at an exposure dose of 80 mJ / cm ² (based on 365 nm) in an air atmosphere. After light irradiation, the layer was post-baked in an oven at 230 ° C. for 30 minutes to obtain a colored coating film.

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

(6) Lightfastness test An ultraviolet ray cut filter (COLORED OPTICAL GLASS L38; manufactured by Hoya Co., Ltd.; cuts light of 380 nm or less) was placed on the obtained colored coating film, and xenon lamp light was irradiated for 48 hours using a lightfastness tester (SUNTEST CPS+; manufactured by Toyo Seiki Co., Ltd.). Before and after the lightfastness test, the color difference ΔE ^* ab of the colored coating film was measured using a colorimeter (OSP-SP-200; manufactured by OLYMPUS Co., Ltd.). The smaller the color difference ΔE ^* ab, the smaller the color change. In addition, before and after the lightfastness test, the fluorescence spectrum was measured using a fluorescence spectrophotometer (FluoroMAX-3; manufactured by Horiba, Ltd.) (excitation side slit 5 nm, fluorescence side slit 10 nm, excitation wavelength 460 nm), and the fluorescence intensity maintenance rate at the fluorescence wavelength was obtained. In this test, the fluorescence intensity maintenance rate is a value obtained by taking the fluorescence intensity of the colored coating film before the light resistance test as 100%. A higher fluorescence intensity maintenance rate means better light resistance. The results are shown in Table 3.

<Examples 4 and 5 and Comparative Example 1>
Instead of 2.6 parts of compound (I-10),
2.6 parts of compound (I-9) (Example 4),
2.6 parts of compound (I-12) (Example 5), or 2.6 parts of Lumogen® F Yellow 083 (Comparative Example 1)
A colored resin composition was obtained and a colored coating film was prepared in the same manner as in Example 3, except that the above was used as a colorant. The solubility of the compound used as a colorant in each Example in PGMEA, the fluorescence intensity measurement results for each colored coating film, and the light resistance test results are shown in Table 3.

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

Claims (7)

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

[In formula (I),
R ¹ and R ² each independently represent a group represented by formula (F-5) or formula (F-13) .

(* represents a bond.)
R ³ , R ⁶ and R ⁸ each represent a group represented by formula (G-8) .

(* represents a bond.)
R ⁴ , R ⁵ , R ⁷ and R ⁹ each represent a hydrogen atom . The colored resin composition according to claim 1, wherein the colorant further contains a perylene compound. The colored resin composition according to claim 1 or 2, further comprising a polymerizable compound and a polymerization initiator. The colored resin composition according to any one of claims 1 to 3, further comprising a solvent. A color filter formed from the colored resin composition according to any one of claims 1 to 4. A display device including the color filter according to claim 5. A compound represented by formula (Ia).

[In formula (Ia),
R ^1a and R ^2a each independently represent a group represented by formula (F-5) or formula (F-13) .

(* represents a bond.)
R ^3a , R ^6a and R ^8a each represent a group represented by formula (G-8) .

(* represents a bond.)
R ^4a , R ^5a , R ^7a and R ^9a each represent a hydrogen atom .