JP7555704B2 - Colored resin composition - Google Patents

Description

The present invention relates to a colored resin composition.

Color filters used in displays such as liquid crystal displays, electroluminescent displays, and plasma displays, and solid-state imaging devices such as CCD and CMOS sensors, are produced from colored curable resin compositions. As such colored curable resin compositions, compositions containing a compound represented by formula (A-X) as a colorant are known (Patent Document 1).

International Publication No. 2014/196464

Conventionally known compositions containing a compound represented by formula (AX) have been used to form color filters that are not satisfactory in terms of chemical resistance.
Therefore, the present invention provides a colored resin composition that is useful for obtaining a color filter having excellent chemical resistance.

［式（Ｉ）中、
Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｒ⁸、Ｒ⁹及びＲ¹⁰は、それぞれ独立に、水素原
子、ヒドロキシ基、ニトロ基、シアノ基、ハロゲン原子、カルボキシ基、スルホ基、スルファモイル基、メタロセニル基、炭素数１～３０の炭化水素基、又は前記炭化水素基中のメチレン基の１つ又は２つ以上が下記群Ｉから選ばれる２価の基で置き換えられた基を表し、ただし、２つ以上のメチレン基が下記群Ｉから選ばれる２価の基で置き換えられている場合、前記２価の基は隣り合わず、
前記炭化水素基に含まれる水素原子は、ハロゲン原子、ニトロ基、シアノ基、ヒドロキシ基、アミノ基、カルボキシ基、スルホ基、ホスホノ基、スルファモイル基、イソシアナト基、複素環で置換されていてもよく、
Ｒ¹¹、Ｒ¹²、Ｒ¹³、Ｒ¹⁴、Ｒ¹⁵及びＲ¹⁶は、それぞれ独立に、水素原子、炭素数１～３０の炭化水素基、又は前記炭化水素基中のメチレン基の１つ又は２つ以上が下記群Ｉから選ばれる２価の基で置き換えられた基を表し、ただし、２つ以上のメチレン基が下記群Ｉから選ばれる２価の基で置き換えられている場合、前記２価の基は隣り合わず、
前記炭化水素基に含まれる水素原子は、複素環又は極性基で置換されていてもよく、
Ｒ¹¹、Ｒ¹²、Ｒ¹³、Ｒ¹⁴、Ｒ¹⁵及びＲ¹⁶のうちの１つ以上が、置換基として極性基を有する基であり、
ｎは、１～３の整数を表し、
Ａ^q-は、ｑ価の陰イオンを表し、
ｑは１～３の整数を表し、
ｐは式（Ｉ）で表される化合物の電荷を中性に保つ係数を表す。
群Ｉ：－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯＳ－、－ＯＣＳ－、－ＳＯ₂－、－ＳＯ₃－、－ＮＨ－、－ＣＯＮＨ－、－ＮＨＣＯ－、－ＳＯ₂ＮＨ－、－ＮＨＳＯ₂－又は－Ｎ＝ＣＨ－］
[２] さらに、重合性化合物及び重合開始剤を含む[１]に記載の着色樹脂組成物。
[３] 着色剤が、さらに顔料（但し、式（Ｉ）で表される化合物を除く。）を含む[１]又は[２]に記載の着色樹脂組成物。
[４] [１]～[３]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。
[５] [４]に記載のカラーフィルタを含む表示装置。
なお本明細書において、各成分として例示する化合物は、特に断りのない限り、単独で又は複数種を組合せて使用することができる。 The present invention is as follows.
[1] A colored resin composition comprising a colorant and a resin, wherein the colorant comprises a compound represented by formula (I).

[In formula (I),
R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ each independently represent a hydrogen atom, a hydroxy group, a nitro group, a cyano group, a halogen atom, a carboxy group, a sulfo group, a sulfamoyl group, a metallocenyl group, a hydrocarbon group having 1 to 30 carbon atoms, or a group in which one or more methylene groups in the hydrocarbon group have been replaced with a divalent group selected from Group I below, with the proviso that when two or more methylene groups have been replaced with a divalent group selected from Group I below, the divalent groups are not adjacent to each other,
a hydrogen atom contained in the hydrocarbon group may be substituted with a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a carboxy group, a sulfo group, a phosphono group, a sulfamoyl group, an isocyanato group, or a heterocycle;
R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ each independently represent a hydrogen atom, a hydrocarbon group having 1 to 30 carbon atoms, or a group in which one or more methylene groups in the hydrocarbon group have been replaced with a divalent group selected from the following group I, with the proviso that when two or more methylene groups have been replaced with a divalent group selected from the following group I, the divalent groups are not adjacent to each other:
A hydrogen atom contained in the hydrocarbon group may be substituted with a heterocyclic ring or a polar group,
one or more of R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ is a group having a polar group as a substituent;
n represents an integer of 1 to 3;
A ^q- represents a q-valent anion;
q represents an integer of 1 to 3;
p represents a coefficient for keeping the charge of the compound represented by formula (I) neutral.
Group I: -O-, -S-, -CO-, -COO-, -OCO-, -COS-, -OCS-, -SO ₂ -, -SO ₃ -, -NH-, -CONH-, -NHCO-, -SO ₂ NH-, -NHSO ₂ - or -N=CH-]
[2] The colored resin composition according to [1], further comprising a polymerizable compound and a polymerization initiator.
[3] The colored resin composition according to [1] or [2], wherein the colorant further comprises a pigment (excluding the compound represented by formula (I)).
[4] A color filter formed from the colored resin composition according to any one of [1] to [3].
[5] A display device comprising the color filter according to [4].
In this specification, the compounds exemplified as each component may be used alone or in combination, unless otherwise specified.

The colored resin composition of the present invention provides a color filter with excellent chemical resistance.

<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)"), and the colorant (A) contains a compound represented by formula (I) (hereinafter, may be referred to as "compound (I)").
The colored resin composition of the present invention preferably further contains a polymerizable compound (hereinafter, sometimes referred to as "polymerizable compound (C)") and a polymerization initiator (hereinafter, sometimes referred to as "polymerization initiator (D)").
The colored resin composition of the present invention may further contain a polymerization initiator aid (D1), a solvent (E) and a leveling agent (F).

<Colorant (A)>
The colored resin composition of the present invention contains the compound (I) as the colorant (A).

<Compound (I)>
Hereinafter, the present invention will be described in detail using formula (I). Compound (I) includes the resonance structure of formula (I), and further includes compounds obtained by rotating each group in formula (I) or its resonance structure around the bond axis of a carbon-carbon single bond or a carbon-nitrogen single bond.

［式（Ｉ）中、
Ｒ¹、Ｒ²、Ｒ³、Ｒ⁴、Ｒ⁵、Ｒ⁶、Ｒ⁷、Ｒ⁸、Ｒ⁹及びＲ¹⁰は、それぞれ独立に、水素原子、ヒドロキシ基、ニトロ基、シアノ基、ハロゲン原子、カルボキシ基、スルホ基、スルファモイル基、メタロセニル基、炭素数１～３０の炭化水素基、又は前記炭化水素基中のメチレン基の１つ又は２つ以上が下記群Ｉから選ばれる２価の基で置き換えられた基を表し、ただし、２つ以上のメチレン基が下記群Ｉから選ばれる２価の基で置き換えられている場合、前記２価の基は隣り合わず、
前記炭化水素基に含まれる水素原子は、ハロゲン原子、ニトロ基、シアノ基、ヒドロキシ基、アミノ基、カルボキシ基、スルホ基、ホスホノ基、スルファモイル基、イソシアナト基、複素環で置換されていてもよく、
Ｒ¹¹、Ｒ¹²、Ｒ¹³、Ｒ¹⁴、Ｒ¹⁵及びＲ¹⁶は、それぞれ独立に、水素原子、炭素数１～３０の炭化水素基、又は前記炭化水素基中のメチレン基の１つ又は２つ以上が下記群Ｉから選ばれる２価の基で置き換えられた基を表し、ただし、２つ以上のメチレン基が下記群Ｉから選ばれる２価の基で置き換えられている場合、前記２価の基は隣り合わず、
前記炭化水素基に含まれる水素原子は、複素環又は極性基で置換されていてもよく、
Ｒ¹¹、Ｒ¹²、Ｒ¹³、Ｒ¹⁴、Ｒ¹⁵及びＲ¹⁶のうちの１つ以上が、置換基として極性基を有する基であり、
ｎは、１～３の整数を表し、
Ａ^q-は、ｑ価の陰イオンを表し、
ｑは１～３の整数を表し、
ｐは式（Ｉ）で表される化合物の電荷を中性に保つ係数を表す。
群Ｉ：－Ｏ－、－Ｓ－、－ＣＯ－、－ＣＯＯ－、－ＯＣＯ－、－ＣＯＳ－、－ＯＣＳ－、－ＳＯ₂－、－ＳＯ₃－、－ＮＨ－、－ＣＯＮＨ－、－ＮＨＣＯ－、－ＳＯ₂ＮＨ－、－ＮＨＳＯ₂－又は－Ｎ＝ＣＨ－］

[In formula (I),
R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ each independently represent a hydrogen atom, a hydroxy group, a nitro group, a cyano group, a halogen atom, a carboxy group, a sulfo group, a sulfamoyl group, a metallocenyl group, a hydrocarbon group having 1 to 30 carbon atoms, or a group in which one or more methylene groups in the hydrocarbon group have been replaced with a divalent group selected from Group I below, with the proviso that when two or more methylene groups have been replaced with a divalent group selected from Group I below, the divalent groups are not adjacent to each other,
a hydrogen atom contained in the hydrocarbon group may be substituted with a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a carboxy group, a sulfo group, a phosphono group, a sulfamoyl group, an isocyanato group, or a heterocycle;
R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ each independently represent a hydrogen atom, a hydrocarbon group having 1 to 30 carbon atoms, or a group in which one or more methylene groups in the hydrocarbon group have been replaced with a divalent group selected from the following group I, with the proviso that when two or more methylene groups have been replaced with a divalent group selected from the following group I, the divalent groups are not adjacent to each other:
A hydrogen atom contained in the hydrocarbon group may be substituted with a heterocyclic ring or a polar group,
one or more of R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ is a group having a polar group as a substituent;
n represents an integer of 1 to 3;
A ^q- represents a q-valent anion;
q represents an integer of 1 to 3;
p represents a coefficient for keeping the charge of the compound represented by formula (I) neutral.
Group I: -O-, -S-, -CO-, -COO-, -OCO-, -COS-, -OCS-, -SO ₂ -, -SO ₃ -, -NH-, -CONH-, -NHCO-, -SO ₂ NH-, -NHSO ₂ - or -N=CH-]

Examples of the hydrocarbon group having 1 to 30 carbon atoms represented by R ¹ to R ¹⁶ include an aliphatic hydrocarbon group having 1 to 30 carbon atoms and an aromatic hydrocarbon group having 6 to 30 carbon atoms.

The aliphatic hydrocarbon group having 1 to 30 carbon atoms may be either saturated or unsaturated, and may be linear, branched, or cyclic.

Examples of linear or branched aliphatic hydrocarbon groups having 1 to 30 carbon atoms include linear aliphatic hydrocarbon groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, vinyl, 1-propenyl, and 2-propenyl (allyl) groups; and branched aliphatic hydrocarbon groups such as isopropyl, isobutyl, isopentyl, neopentyl, and 2-ethylhexyl groups. The number of carbon atoms in the linear or branched aliphatic hydrocarbon group is preferably 1 to 15, more preferably 1 to 10, and even more preferably 1 to 8.
The cyclic aliphatic hydrocarbon group may be monocyclic or polycyclic. Examples of the cyclic aliphatic hydrocarbon group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group. The number of carbon atoms in the cyclic aliphatic hydrocarbon group is preferably 3 to 18, more preferably 3 to 15, and even more preferably 4 to 15.

Examples of aromatic hydrocarbon groups having 6 to 30 carbon atoms include phenyl groups, naphthyl groups, phenanthryl groups, and anthryl groups. The number of carbon atoms in the aromatic hydrocarbon group is preferably 6 to 20, more preferably 6 to 18, and even more preferably 6 to 15.

The hydrocarbon group having 1 to 30 carbon atoms may be a group that combines two or more of the above-listed aliphatic hydrocarbon groups and aromatic hydrocarbon groups, so long as the upper limit of the carbon number is 30 or less. Examples of such groups include a xylyl group, a trimethylphenyl group, a dipropylphenyl group, a di(2,2-dimethylpropyl)phenyl group, a benzyl group, a phenethyl group, and a 4-phenylbutyl group. The number of carbon atoms in the group that combines two or more aliphatic hydrocarbon groups and aromatic hydrocarbon groups is preferably 7 to 25, more preferably 8 to 20, and even more preferably 8 to 15.

Examples of the hydrocarbon group represented by R ¹ to R ¹⁶ in which one of the methylene groups has been replaced with a divalent group selected from Group I below include the following.
Group I: -O-, -S-, -CO-, -COO-, -OCO-, -COS-, -OCS-, -SO ₂ -, -SO ₃ -, -NH-, -CONH-, -NHCO-, -SO ₂ NH-, -NHSO ₂ - or -N=CH-

Examples of groups in which one of the methylene groups in a hydrocarbon group has been replaced with -O- include the following (* represents a bond):

Examples of groups in which one of the methylene groups in a hydrocarbon group has been replaced with -S- include the following (* represents a bond):

Examples of hydrocarbon groups in which one of the methylene groups has been replaced with -CO- include the following (* represents a bond):

Examples of groups in which one of the methylene groups in a hydrocarbon group has been replaced with -COO- include the following (* represents a bond):

Examples of groups in which one of the methylene groups in a hydrocarbon group has been replaced with -OCO- include the following (* represents a bond):

Examples of groups in which one of the methylene groups in a hydrocarbon group has been replaced with -COS- include the following (* represents a bond):

Examples of groups in which one of the methylene groups in a hydrocarbon group has been replaced with -OCS- include the following (* represents a bond):

Examples of the hydrocarbon group in which one of the methylene groups is replaced by -SO ₂ - include
The following are included (* represents a bond):

Examples of the hydrocarbon group in which one of the methylene groups is replaced by -SO ₃ - include
The following are included (* represents a bond):

Examples of groups in which one methylene group in a hydrocarbon group has been replaced with -NH- include the following (* represents a bond):

Examples of groups in which one of the methylene groups in a hydrocarbon group has been replaced with -CONH- include the following (* represents a bond):

Examples of groups in which one of the methylene groups in a hydrocarbon group has been replaced with -NHCO- include the following (* represents a bond):

Examples of a hydrocarbon group in which one of the methylene groups has been replaced with --SO ₂ NH-- include the following (* represents a bond):

Examples of a hydrocarbon group in which one of the methylene groups has been replaced with --NHSO ₂ -- include the following (* represents a bond):

Examples of groups in which one methylene group in a hydrocarbon group has been replaced with -N=CH- include the following (* represents a bond):

The group in which two or more methylene groups in the hydrocarbon group represented by R ¹ to R ¹⁶ have been replaced with a divalent group selected from Group I above may be any of the divalent groups in Group I above, provided that the divalent groups are not adjacent to each other, and examples thereof include an appropriate combination of groups in which one methylene group in the hydrocarbon group has been replaced with a divalent group selected from Group I above.

It is preferred that one or more methylene groups in the hydrocarbon groups represented by R ¹¹ to R ¹⁶ do not form a polar group when replaced with a divalent group selected from group I above.

Examples of the halogen atom represented by R ¹ to R ¹⁰ include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, with a chlorine atom being preferred.

Examples of the metallocenyl group represented by R ¹ to R ¹⁰ include a ferrocenyl group, a nickelocenyl group, a cobaltyl group, a ferrocene alkyl group, and a ferrocene alkoxy group.

Examples of the halogen atoms with which the hydrogen atoms contained in the hydrocarbon groups represented by R ¹ to R ¹⁰ may be substituted are the same as the halogen atoms represented by R ¹ to R ¹⁰ .

The number of carbon atoms in the heterocycle in which a hydrogen atom contained in the hydrocarbon group represented by R ¹ to R ¹⁶ may be substituted is preferably 1 to 20. Examples of the heterocycle include heterocycles containing at least one atom selected from a nitrogen atom, an oxygen atom, and a sulfur atom, and specific examples thereof include azetidine, pyrrole, benzoxazole, thiazole, oxetane, furan, thietane, thiophene, etc.

R ¹ to R ¹⁰ are preferably hydrogen atoms or halogen atoms, more preferably 1 to 6 of R ¹ to R ¹⁰ are halogen atoms and the rest are hydrogen atoms, even more preferably 1 to 4 of R ¹ to R ¹⁰ are halogen atoms and the rest are hydrogen atoms, and still more preferably 2 of R ¹ to R ¹⁰ are halogen atoms and the rest are hydrogen atoms.

When two of R ¹ to R ¹⁰ are halogen atoms, the two halogen atoms are preferably any two of R ⁷ to R ¹⁰ , and it is more preferable that R ⁷ and R ⁹ are halogen atoms.

The polar group in which a hydrogen atom contained in the hydrocarbon group represented by R ¹¹ to R ¹⁶ may be substituted refers to a functional group containing at least one heteroatom other than carbon atoms and hydrogen atoms. Examples of the heteroatom include an oxygen atom, a sulfur atom, a phosphorus atom, a nitrogen atom, and a halogen atom. Specific examples of the polar group include a hydroxyl group, a carboxyl group, an epoxy group, an amide group (including an amide group N-substituted with a hydrocarbon group having 1 to 12 carbon atoms, such as an N-methylamide group, an N-isopropylamide group, an N-cyclopropylamide group, and an N-phenylamide group), a nitrile group, an amino group, an imide group, an isocyanato group, a thiol group, an alkoxy group, a sulfo group, a phosphono group, a nitro group, an alkoxycarbonyl group, an acyl group such as an acetyl group, and a halogen atom. Among these, an acid group such as a carboxyl group, an amide group, a sulfo group, or a phosphono group is preferred, a carboxyl group or an amide group is more preferred, and a carboxyl group is even more preferred.

Examples of groups having a polar group as a substituent, in which a hydrogen atom contained in a hydrocarbon group is replaced with a polar group, include groups represented by the following formulas (po-1) to (po-6) in which the polar group is a carboxy group, and groups represented by the following formulas (po-7) to (po-10) in which the polar group is an amide group. In the formulas, * represents a bond.

At least one of R ¹¹ to R ¹⁶ is a group having a polar group as a substituent, in which a hydrogen atom contained in the hydrocarbon group represented by R ¹¹ to R ¹⁶ is substituted with a polar group. If at least one of R ¹¹ to R ¹⁶ is a group having a polar group as a substituent, a color filter having excellent chemical resistance can be formed.

R ¹¹ to R ¹⁶ are preferably a hydrocarbon group having 1 to 30 carbon atoms, more preferably a hydrocarbon group having 1 to 20 carbon atoms, even more preferably an aliphatic hydrocarbon group, and even more preferably a saturated linear aliphatic hydrocarbon group. The number of carbon atoms in the saturated linear aliphatic hydrocarbon group is preferably 1 to 15, more preferably 1 to 10, and even more preferably 1 to 5. In addition, when R ¹¹ to R ¹⁶ are groups having a polar group as a substituent, R ¹¹ to R ¹⁶ are preferably an aliphatic hydrocarbon group or a group combining two or more aliphatic hydrocarbon groups and aromatic hydrocarbon groups, and when R ¹¹ to R ¹⁶ are groups not having a polar group as a substituent, R ¹¹ to R ¹⁶ are preferably an aliphatic hydrocarbon group or an aromatic hydrocarbon group.

In addition, it is preferable that one to four of R ¹¹ to R ¹⁶ are groups having a polar group as a substituent, it is more preferable that two to four of R 11 to R 16 are groups having a polar group as a substituent, and it is even more preferable that two of R ¹¹ to R ¹⁶ are groups having a polar group as a substituent.

n is preferably 1 or 2, and more preferably 1.

The q-valent anion represented by A ^q- is a monovalent to trivalent anion, and may be either an inorganic anion or an organic anion.
Examples of the inorganic anion include hydroxide ion, halide ion (fluoride ion, chloride ion, bromide ion, iodide ion, etc.), nitrate ion, perchlorate ion, chlorate ion, sulfate ion, thiocyanate ion, phosphate ion, phosphotungstate ion, phosphomolybdate ion, phosphotungstate molybdate ion, hexafluorophosphate ion, molybdate ion, tungstate ion, titanate ion, zirconate ion, borate ion, tetrafluoroborate ion, and the like.
Examples of the organic anion include organic carboxylate anions such as acetate ion, trifluoroacetate ion, benzoate ion, palmitate ion, tartrate ion, and ethylenediaminetetraacetate iron ion; methanesulfonate ion, dodecylsulfonate ion, vinylsulfonate ion, benzenesulfonate ion, trifluoromethanesulfonate ion, nonafluorobutanesulfonate ion, 3-(trihydroxysilyl)-1-propanesulfonate ion, toluenesulfonate ion, chlorobenzenesulfonate ion, pentafluorobenzenesulfonate ion, 3-carboxyphenylsulfonate, 3-nitrophenylsulfonate ion, benzenedisulfonate ion, and diphenylamine-4-sulfonate. phosphate ion, 2-amino-4-methyl-5-chlorobenzenesulfonate ion, 2-amino-5-nitrobenzenesulfonate ion, phthalocyanine sulfonate ion, perfluoro-4-ethylcyclohexanesulfonate ion, naphthalene monosulfonate ion, naphthalenedisulfonate ion, naphthalene trisulfonate ion, naphthylamine monosulfonate ion, naphthylamine disulfonate ion, naphthylamine trisulfonate ion, 8-{[3-(trimethoxysilyl)propyl]amino}naphthalene-1-sulfonate ion, 8-{[3-(trimethoxysilyl)propyl]amino}naphthalene-1,5-disulfonate ion, isoquinoline-5-sulfonate ion, naphthol mono organic sulfonate anions such as naphthol disulfonate ion, naphthol trisulfonate ion, and N,N-bis(2-hydroxyethyl)-2-aminoethanesulfonate ion; organic phosphate anions such as octyl phosphate ion, dodecyl phosphate ion, octadecyl phosphate ion, phenyl phosphate ion, nonylphenyl phosphate ion, 2,2'-methylenebis(4,6-di-t-butylphenyl)phosphonate ion, and 3-(trihydroxysilyl)propylmethylphosphonate ion; organic sulfate anions such as lauryl sulfate ion, laureth sulfate ion, polyoxyethylene alkylphenol sulfonate ion, and lauryl sulfate ion; tetraarylborate ion, butyl triphosphate ion, and butyl triphosphate ion. Examples of the anions include organic borate anions such as phenylborate ion; methide ions such as tricyanomethide ion, tris(trifluoromethanesulfonyl)methide ion, and tris(perfluoroethylsulfonyl)methide ion; dicyanamide ion; sulfonamide ions such as trifluoromethanesulfonamide ion and benzenesulfonamide ion; and sulfonimide ions such as N,N-bis(fluorosulfonyl)imide ion, bis(trifluoromethylsulfonyl)imide ion, bis(nonafluorobutanesulfonyl)imide ion, N,N-hexafluoro-1,3-disulfonylimide ion, and 1,1,2,2,3,3-hexafluoropropane-1,3-disulfonimide ion.

The q-valent anion represented by A ^q- is preferably a hexafluorophosphate ion, a tungstate ion, a monovalent organic carboxylate anion, a monovalent or divalent organic sulfonate anion, a monovalent organic phosphate anion, a monovalent organic borate anion, a monovalent methide ion, a dicyanamide ion, a monovalent sulfonamide ion, or a monovalent sulfonimide ion, more preferably a tungstate ion, a monovalent organic carboxylate anion, a monovalent or divalent organic sulfonate anion, a monovalent organic phosphate anion, a monovalent methide ion, a dicyanamide ion, or a monovalent sulfonimide ion, and more preferably a tungstate ion, a monovalent organic carboxylate anion, a monovalent or divalent organic sulfonate anion, a monovalent organic phosphate anion, a monovalent methide ion, a dicyanamide ion, or a monovalent sulfonimide ion. More preferred are acid anions, monovalent organic phosphate anions, monovalent methide ions, and monovalent sulfonimide ions; even more preferred are tungstate ions, monovalent organic carboxylate anions, monovalent or divalent organic sulfonate anions, monovalent organic phosphate anions, and monovalent sulfonimide ions; still more preferred are tungstate ions, monovalent organic carboxylate anions, monovalent or divalent organic sulfonate anions, and monovalent sulfonimide ions; still more preferred are monovalent organic sulfonate anions and monovalent sulfonimide ions; and particularly preferred are 3-carboxyphenylsulfonic acid and bis(trifluoromethylsulfonyl)imide ions.

Examples of compound (I) include compounds represented by formulas (I-1) to (I-146) shown in Tables 1 to 4.
Compound (I) is preferably a compound represented by formulas (I-25) to (I-48), (I-73), (I-74), (I-77) to (I-80), (I-87), (I-88), or (I-109) to (I-127).

In Tables 1 to 4, Et represents an ethyl group, Pr represents a propyl group, and Ph represents a phenyl group; po-2 to po-4, po-6, po-7, and po-9 represent groups represented by the above formulas (po-2) to (po-4), (po-6), (po-7), and (po-9), respectively; and an-1 to an-21 represent groups represented by the following formulas (an-1) to (an-21), respectively.

The method for synthesizing compound (I) is not particularly limited, but it can be synthesized by referring to the method described in WO 2014/196464.

The content of compound (I) is preferably 0.05 to 100 parts by mass, more preferably 0.1 to 80 parts by mass, even more preferably 0.5 to 50 parts by mass, and even more preferably 0.5 to 30 parts by mass, relative to 100 parts by mass of resin (B).

The content of compound (I) in the total amount of colorant (A) is preferably 1% by mass or more, and more preferably 5% by mass or more.

In addition to compound (I), colorant (A) may contain a colorant different from compound (I). The colorant different from compound (I) may be either a dye (hereinafter, sometimes referred to as dye (A1)) or a pigment (hereinafter, sometimes referred to as pigment (A2)). The colorant different from compound (I) may contain one or both of these dyes (A1) and pigments (A2).

As long as the dye (A1) does not contain compound (I), it is not particularly limited and known dyes can be used, such as solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified as having hues other than pigments in the Color Index (published by The Society of Dyers and Colourists) and known dyes described in Dyeing Notes (Shikisensha). In addition, examples of dyes that can be used according to chemical structure include azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, coumarin dyes, quinoline dyes, and nitro dyes. Of these, organic solvent-soluble dyes are preferred.

The pigment (A2) is not particularly limited and any known pigment can be used. For example, pigments classified as pigments in the Color Index (published by The Society of Dyers and Colourists) can be used.
Examples of pigments include yellow pigments such as C.I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, and 214;
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, 123, 144, 149, 166, 168, 176, 177, 180, 192, 202, 209, 215, 216, 224, 242, 254, 255, 264, 265, 269, 291;
blue pigments such as C.I. Pigment Blue 15, 15:3, 15:4, 15:6, 60;
Violet pigments such as C.I. Pigment Violet 1, 19, 23, 29, 32, 36, 38;
green pigments such as C.I. Pigment Green 7, 36, 58;
Brown pigments such as C.I. Pigment Brown 23 and 25;
Examples of the black pigment include black pigments such as C.I. Pigment Black 1 and 7.

As the pigment (A2), preferred are yellow pigments such as C.I. Pigment Yellow 185; red pigments such as C.I. Pigment Red 177, 202, 264, 269, and 291; and blue pigments such as C.I. Pigment Blue 15:6.

It is preferable that the pigment has a uniform particle size, and by adding a pigment dispersant and carrying out a dispersion process, a pigment dispersion liquid in which the pigment is uniformly dispersed in the solution can be obtained.

Examples of the pigment dispersant include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants.
When a pigment dispersant is used, the amount thereof is preferably 1% by mass or more and 100% by mass or less, more preferably 5% by mass or more and 50% by mass or less, based on the total amount of the pigment (A2). When the amount of the pigment dispersant used is within the above range, a pigment dispersion in a uniformly dispersed state tends to be obtained.

The content of colorant (A) is preferably 0.5 to 60 mass%, more preferably 1 to 50 mass%, and even more preferably 3 to 45 mass%, based on the total amount of solids in the colored resin composition. Here, the "total amount of solids" in this specification refers to the amount obtained by excluding the solvent content from the total amount of the colored resin composition. The total amount of solids and the content of each component relative to the total amount of solids can be measured by known analytical means such as liquid chromatography or gas chromatography.

<Resin (B)>
Resin (B) is not particularly limited, but is preferably an alkali-soluble resin, and more preferably a resin having a structural unit derived from at least one type (a) (hereinafter, sometimes referred to as "(a)") selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides. Resin (B) further preferably has at least one structural unit selected from the group consisting of a structural unit derived from a monomer (b) (hereinafter, sometimes referred to as "(b)") having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond, a structural unit derived from a monomer (c) (however different from (a) and (b)) (hereinafter, sometimes referred to as "(c)") copolymerizable with (a), and a structural unit having an ethylenically unsaturated bond in a side chain.

Specific examples of (a) include acrylic acid, methacrylic acid, maleic anhydride, itaconic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, and mono[2-(meth)acryloyloxyethyl]succinate, with acrylic acid, methacrylic acid, and maleic anhydride being preferred.

(b) is preferably a monomer 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) and a (meth)acryloyloxy group.
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.
Examples of (b) include glycidyl (meth)acrylate, vinylbenzyl glycidyl ether, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate, 3-ethyl-3-(meth)acryloyloxymethyloxetane, and tetrahydrofurfuryl (meth)acrylate, and preferred are glycidyl (meth)acrylate, 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]decyl (meth)acrylate, and 3-ethyl-3-(meth)acryloyloxymethyloxetane.

Examples of (c) include methyl (meth)acrylate, butyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-methylcyclohexyl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ] decan-8-yl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ] decan-9-yl (meth)acrylate, benzyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, styrene, and vinyltoluene. Preferred are styrene, vinyltoluene, 2-hydroxyethyl (meth)acrylate, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, tricyclo[5.2.1.0 ^2,6 ] decan-8-yl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]Decan-9-yl (meth)acrylate and the like are preferred.

A resin having a structural unit with an ethylenically unsaturated bond in the side chain can be produced by adding (b) to a copolymer of (a) and (c), or by adding (a) to a copolymer of (b) and (c). The resin may be a resin obtained by adding (a) to a copolymer of (b) and (c) and then reacting with a carboxylic acid anhydride.

The polystyrene-equivalent weight average molecular weight of resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and even more preferably 5,000 to 30,000.
The polydispersity of the resin (B) [weight average molecular weight (Mw)/number average molecular weight (Mn)] is preferably 1.1-6, and more preferably 1.2-4.

The acid value of resin (B) is preferably 20 to 170 mg-KOH/g, more preferably 30 to 150 mg-KOH/g, and even more preferably 40 to 135 mg-KOH/g, calculated as solid content. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of resin (B), and can be determined, for example, by titration with an aqueous potassium hydroxide solution.

The content of resin (B) is preferably 10 to 90% by mass, more preferably 20 to 80% by mass, and even more preferably 25 to 70% by mass, based on the total amount of solids in the colored resin composition.

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

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, and dipentaerythritol hexa(meth)acrylate.

The weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, more preferably 250 or more and 1,500 or less.

When the polymerizable compound (C) is contained, the content of the polymerizable compound (C) is preferably 5 to 60 mass % relative to the total amount of solids in the colored resin composition, more preferably 10 to 50 mass %, and even more preferably 15 to 40 mass %.

<Polymerization initiator (D)>
The polymerization initiator (D) is not particularly limited as long as it is a compound that generates active radicals, acids, etc. by the action of light or heat and can initiate polymerization, and known polymerization initiators can be used. Examples of polymerization initiators that generate active radicals 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-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine, and N-acetyloxy-1-(4-phenylsulfanylphenyl)-3-cyclohexylpropan-1-one-2-imine. amine, 2-methyl-2-morpholino-1-(4-methylsulfanylphenyl)propan-1-one, 2-dimethylamino-1-(4-morpholinophenyl)-2-benzylbutan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2,4-bis(trichloromethyl)-6-piperonyl-1,3,5-triazine, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenylbiimidazole, and the like.

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

When a polymerization initiator (D) is included, the content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, and more preferably 1 to 20 parts by mass, per 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). 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 a polymerizable compound whose polymerization has been initiated by a polymerization initiator, 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 4,4'-bis(dimethylamino)benzophenone (commonly known as Michler's ketone), 4,4'-bis(diethylamino)benzophenone, 9,10-dimethoxyanthracene, 2,4-diethylthioxanthone, and N-phenylglycine.

When these polymerization initiation aids (D1) are used, the content is preferably 0.1 to 30 parts by mass, and more preferably 1 to 20 parts by mass, per 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). When the amount of the polymerization initiation aid (D1) is within this range, a colored pattern can be formed with even higher sensitivity, and the productivity of the color filter tends to improve.

<Solvent (E)>
The solvent (E) is not particularly limited, and a solvent normally used in the relevant field can be used. Examples thereof include ester solvents (solvents containing -COO- and not containing -O- in the molecule), ether solvents (solvents containing -O- and not containing -COO- in the molecule), ether ester solvents (solvents containing -COO- and -O- in the molecule), ketone solvents (solvents containing -CO- and not containing -COO- in the molecule), alcohol solvents (solvents containing OH in the molecule and not containing -O-, -CO- and -COO-), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, etc.

As a solvent,
Ester solvents (solvents containing -COO- but not -O- in the molecule) such as ethyl lactate, butyl lactate, methyl 2-hydroxyisobutanoate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, methyl acetoacetate, cyclohexanol acetate, and γ-butyrolactone;
Ether solvents (solvents containing -O- but not -COO- in the molecule), such as ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, 3-methoxy-1-butanol, diethylene glycol dimethyl ether, and diethylene glycol methyl ethyl ether;
Ether ester solvents (solvents containing -COO- and -O- in the molecule), such as methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, 3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, and diethylene glycol monoethyl ether acetate;
Ketone solvents (solvents containing —CO— but not —COO— in the molecule), such as 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), heptanone, 4-methyl-2-pentanone, and cyclohexanone;
Alcohol solvents (solvents containing OH in the molecule but not containing —O—, —CO— or —COO—) such as butanol, cyclohexanol, propylene glycol, etc.;
Amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone; and the like.
More preferred solvents are propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, 4-hydroxy-4-methyl-2-pentanone (diacetone alcohol), ethyl lactate and ethyl 3-ethoxypropionate.

When the solvent (E) is contained, the content of the solvent (E) is preferably 60 to 95% by mass, more preferably 65 to 92% by mass, based on the total amount of the colored resin composition of the present invention. In other words, the total amount of solids in the colored resin composition is preferably 5 to 40% by mass, more preferably 8 to 35% by mass. When the content of the solvent (E) is within the above range, the flatness during application is good, and the color density is not insufficient when a color filter is formed, so that the display characteristics tend to be good.

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

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 the fluorosurfactant 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 the silicone surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain 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 included, the content of the leveling agent (F) is preferably 0.001 to 0.2 mass % relative to the total amount of the colored resin composition, and more preferably 0.002 to 0.1 mass %. 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 of the present invention may contain additives known in the art, such as a filler, a polymer compound, an adhesion promoter, an antioxidant, a light stabilizer, and a chain transfer agent, as necessary.

<Method of producing colored resin composition>
The colored resin composition of the present invention can be prepared by mixing the colorant (A) and the resin (B), as well as the polymerizable compound (C), polymerization initiator (D), polymerization initiator assistant (D1), solvent (E), leveling agent (F) and other components that are used as needed.

<Color Filter Manufacturing Method>
Methods for producing a colored pattern from the colored resin composition of the present invention include photolithography, inkjet printing, etc. Among these, photolithography is preferred.

The colored resin composition contains a colorant and a resin, and the colorant contains compound (I), so that a color filter with excellent chemical resistance can be produced. The color filter is useful as a color filter for use in display devices (e.g., liquid crystal display devices, organic EL devices, electronic paper, etc.) and solid-state imaging devices.

The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. In the examples, percentages and parts indicating the content or amount used are based on mass unless otherwise specified.

Synthesis Example 1
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, 141 parts of ethyl lactate and 178 parts of propylene glycol monomethyl ether acetate were added, and the mixture was heated to 85°C while stirring. Next, a mixed solution of 38 parts of acrylic acid, 25 parts of a mixture of 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]dec-8-yl acrylate and 3,4-epoxytricyclo[5.2.1.0 ^2,6 ]dec-9-yl acrylate (content ratio 1:1), 137 parts of cyclohexylmaleimide, 50 parts of 2-hydroxyethyl methacrylate, and 338 parts of propylene glycol monomethyl ether acetate was added dropwise over 5 hours. Meanwhile, a mixed solution of 5 parts of 2,2-azobisisobutyronitrile dissolved in 88 parts of propylene glycol monomethyl ether acetate was added dropwise over 6 hours. After the dropwise addition, the mixture was kept at the same temperature for 4 hours and then cooled to room temperature to obtain a copolymer (resin (B-1)) solution with a solid content of 25.6%. The weight average molecular weight Mw of the copolymer produced was 8000, the dispersity was 2.1, and the acid value calculated as the solid content was 111 mg-KOH/g. Resin (B-1) has the following structural units.

Synthesis Example 2
A suitable amount of nitrogen was flowed into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to create a nitrogen atmosphere, 280 parts of propylene glycol monomethyl ether acetate was placed in the flask and heated to 80°C with stirring. Next, a 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) dissolved in 125 parts of propylene glycol monomethyl ether acetate was dropped into the flask using a dropping pump over about 5 hours. Meanwhile, a solution of 33 parts of the polymerization initiator 2,2-azobis(2,4-dimethylvaleronitrile) dissolved in 235 parts of propylene glycol monomethyl ether acetate was dropped into the flask using another dropping pump over about 6 hours. After the dropwise addition, the mixture was kept at the same temperature for 4 hours and then cooled to room temperature to obtain a copolymer (resin (B-2)) solution with a solid content of 35.1%. The weight average molecular weight Mw of the copolymer produced was 9,200, the dispersity was 2.08, and the acid value calculated as the solid content was 77 mg-KOH/g. Resin (B-2) has the following structural units.

The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by GPC under the following conditions.
Apparatus: HLC-8120GPC (manufactured by Tosoh Corporation)
Column: TSK-GELG2000HXL
Column temperature: 40°C
Solvent: THF
Flow rate: 1.0mL/min
Test liquid solid content concentration: 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 3
4 parts of N,N-diethylamino-3-phenol, 0.5 parts of a compound represented by the following formula (B-1), and 7.4 parts of trifluorosulfonic acid were mixed and stirred at 100 ° C. for 3 hours to obtain a reaction solution. After cooling the reaction solution to room temperature, 50 parts of water was added to the reaction solution, extracted with chloroform and ethyl acetate, and each organic layer was washed with water. The washed organic layers were combined and the solvent was distilled off. 0.9 parts of p-chloranil and 50 parts of acetonitrile were added to the residue and stirred at room temperature for 12 hours. After distilling off the solvent from the reaction solution, 50 parts of chloroform were added and the precipitated solid was filtered off. After concentrating the filtrate, 50 parts of a 4% aqueous sodium hydroxide solution was added to the concentrated filtrate and stirred at room temperature for 12 hours. The reaction solution was neutralized to pH 4 with 2N hydrochloric acid, and the precipitated solid was filtered off. The obtained solid was dispersed and washed with a mixed solution of ethyl acetate-hexane (3:1) for 3 hours, dried, and dissolved in 5 parts of concentrated hydrochloric acid to obtain a solution. The obtained solution was filtered, and the filtrate was crystallized with 20% saline and neutralized with 25% aqueous sodium hydroxide solution until the pH became 4. The precipitated solid was collected by filtration and dried in a reduced pressure oven at 60° C. to obtain 0.21 parts (yield 24%) of a compound represented by formula (A-Y).

0.77 parts of the compound represented by formula (A-Y), 0.5 parts of bis(trifluoromethanesulfonyl)lithium, and 12.3 parts of N,N-dimethylsulfoxide were mixed and stirred at 50°C for 3 hours to obtain a reaction solution. The obtained reaction solution was dropped into 40 parts of 20% saline, and the precipitated solid was collected by filtration. The solid was dissolved in chloroform, the organic layer was washed with water, and then sodium sulfate was added and dried, followed by distillation of the solvent, and the mixture was dried in a reduced pressure oven at 60°C to obtain 0.73 parts (yield 76%) of the compound represented by formula (A-2). The mass analysis result of the obtained compound was m/z = 654 [M] ⁺ . In addition, mass analysis was performed using an Agilent 1200 model LC and an Agilent LC/MSD6130 model MASS (the same applies to the following mass analysis).

Synthesis Example 4
3 parts of the compound represented by formula (A-2), 5 parts of ethyl 4-aminobenzoate, 6 parts of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 0.5 parts of 4-dimethylaminopyridine, 0.4 parts of (+)-10-camphorsulfonic acid, and 156 parts of dimethylsulfoxide were mixed and stirred at room temperature for 3 hours. The reaction product was crystallized in saturated saline, and the precipitated solid was collected by filtration and washed three times with 100 parts of water. The mixture was dried in a reduced pressure oven at 60°C to obtain 1.6 parts (yield 34%) of the compound represented by formula (A-6). The mass spectrometry result of the obtained compound was m/z = 892 [M] ⁺ .

Synthesis Example 5
Except for changing ethyl 4-aminobenzoate to aniline, 2.0 parts (yield 42%) of a compound represented by formula (A-7) was obtained in the same manner as in Synthesis Example 4. The mass spectrometry result of the obtained compound was m/z = 804 [M] ⁺ .

Synthesis Example 6
0.6 parts of 3-hydroxydiphenylamine, 0.6 parts of the compound represented by the above formula (B-1), and 8.8 parts of trifluoromethanesulfonic acid were mixed and stirred at 100°C for 4 hours to obtain a reaction solution. After cooling the reaction solution to room temperature, 50 parts of water were added to the reaction solution, extracted with chloroform and ethyl acetate, and each organic layer was washed with water. The washed organic layers were combined and the solvent was distilled off. 0.6 parts of p-chloranil and 11 parts of acetonitrile were added to the residue and stirred at room temperature for 10 hours. After distilling off the solvent from the reaction solution, 30 parts of chloroform were added and the precipitated solid was filtered off. After concentrating the filtrate, 20 parts of a 4% aqueous sodium hydroxide solution was added to the concentrated filtrate and stirred at room temperature for 12 hours. The reaction solution was neutralized to pH 4 with 2N hydrochloric acid, and the precipitated solid was filtered off. The obtained solid was dispersed and washed with a mixed solution of ethyl acetate-hexane (3:1) for 5 hours, dried, and dissolved in 5 parts of concentrated hydrochloric acid to obtain a solution. The resulting solution was filtered, the filtrate was crystallized with 20% saline, and neutralized with 25% aqueous sodium hydroxide until the pH was 4. The precipitated solid was collected by filtration, mixed with 7.6 parts of ethyl iodide, 4.1 parts of potassium carbonate, and 5 parts of N-methyl-2-pyrrolidone, and stirred at 75°C for 17 hours. After cooling the reaction solution to room temperature, 70 parts of 2N hydrochloric acid was added to the reaction solution, extracted with chloroform, the organic layer was washed with water, and the solvent was distilled off. The mixture was dried in a reduced pressure oven at 60°C to obtain 0.2 parts (yield 15%) of the compound represented by formula (B-2). The mass spectrometry result of the obtained compound was m/z = 750 [M] ⁺ .
Next, 0.2 parts of the compound represented by formula (B-2), 0.1 parts of bis(trifluoromethanesulfonyl)lithium, and 2.7 parts of N,N-dimethylsulfoxide were mixed and stirred at 50° C. for 5 hours to obtain a reaction solution. The obtained reaction solution was added dropwise to 40 parts of 20% saline, and the precipitated solid was collected by filtration. The solid was dissolved in chloroform, and the organic layer was washed with water, and then sodium sulfate was added thereto and dried, followed by distilling off the solvent, and drying in a reduced pressure oven at 60° C. to obtain 0.2 parts of the compound represented by formula (A-8) (yield 90%).

Synthesis Example 7
15.0 parts of 3,5-dichloroaniline, 19.9 parts of ethyl 4-bromobutyrate, 35.9 parts of N,N-diisopropylethylamine, and 52.5 parts of N,N-dimethylformamide were mixed and heated and stirred at 120°C for 2 hours. Subsequently, 28.9 parts of ethyl iodide were added to the reaction solution, and the mixture was heated and stirred at 70°C for 24 hours. After cooling to room temperature, the reaction product was extracted with ethyl acetate, and the extracted reaction product was washed with water. The organic layer was distilled off, and the residue was purified by silica gel column chromatography (developing solvent: ethyl acetate:hexane = 1:5). Furthermore, 28.4 parts of phosphoryl chloride and 52.5 parts of N,N-dimethylformamide were mixed with the compound obtained at 0°C, and the mixture was heated and stirred at 60°C for 6 hours. The reaction product was crystallized in a 4% aqueous sodium hydroxide solution, and the precipitated solid was collected by filtration and washed with 100 parts of methanol. The precipitate was dried in a vacuum oven at 60° C. to obtain 5.0 parts (yield: 16%) of the compound represented by formula (B-3). The mass spectrometry result of the compound thus obtained was m/z=333[M+H] ⁺ .

Except for changing the compound represented by formula (B-1) to the compound represented by formula (B-3) and changing 3-hydroxydiphenylamine to N,N-diethylaminophenol, the same procedure as in Synthesis Example 6 was repeated to obtain 1.3 parts (yield 31%) of the compound represented by formula (B-4). The mass spectrometry result of the obtained compound was m/z = 596 [M] ⁺ .

Subsequently, 0.4 parts (yield 64%) of the compound represented by formula (A-9) was obtained in the same manner as in Synthesis Example 6, except that the compound represented by formula (B-2) was replaced with the compound represented by formula (B-4).

[Synthesis Example 8]
The same procedure as in Synthesis Example 7 was repeated except that bis(trifluoromethanesulfonyl)lithium was changed to monosodium 3-sulfobenzoate, to obtain 0.3 parts (yield 45%) of the compound represented by formula (A-10).

[Synthesis Example 9]
The same procedure as in Synthesis Example 3 was repeated except that bis(trifluoromethanesulfonyl)lithium was changed to lithium bis(fluorosulfonyl)imide, to obtain 0.88 parts (yield 91%) of the compound represented by formula (A-11).

Synthesis Example 10
The same procedure as in Synthesis Example 3 was conducted except that bis(trifluoromethanesulfonyl)lithium was changed to lithium trifluoromethanesulfonate, to obtain 0.77 parts (yield 71%) of the compound represented by formula (A-12).

Synthesis Example 11
The same procedure as in Synthesis Example 3 was repeated except that bis(trifluoromethanesulfonyl)lithium was changed to lithium nonafluoro-1-butanesulfonate, to obtain 0.5 parts of the compound represented by formula (A-13) (yield 72%).

Synthesis Example 12
The same procedure as in Synthesis Example 3 was repeated except that bis(trifluoromethanesulfonyl)lithium was changed to sodium tetraphenylborate, to obtain 0.93 parts (yield 83%) of the compound represented by formula (A-14).

Synthesis Example 13
The same procedure as in Synthesis Example 3 was repeated except that bis(trifluoromethanesulfonyl)lithium was changed to sodium dicyanamide, to obtain 0.78 parts (yield 93%) of the xanthene compound represented by formula (A-15).

Synthesis Example 14
The same procedure as in Synthesis Example 3 was repeated except that bis(trifluoromethanesulfonyl)lithium was changed to lithium hexafluorophosphate, to obtain 0.58 parts (yield 63%) of the compound represented by formula (A-16).

Synthesis Example 15
The same procedure as in Synthesis Example 3 was repeated except that bis(trifluoromethanesulfonyl)lithium was changed to sodium 3-nitrobenzenesulfonate, to obtain 0.74 parts (yield 75%) of the compound represented by formula (A-17).

Synthesis Example 16
The same procedure as in Synthesis Example 3 was repeated except that bis(trifluoromethanesulfonyl)lithium was changed to sodium isoquinoline-5-sulfonate, to obtain 0.65 parts (yield 63%) of the compound represented by formula (A-18).

Synthesis Example 17
The same procedure as in Synthesis Example 3 was conducted except that bis(trifluoromethanesulfonyl)lithium was changed to trifluoromethanesulfonamide, to obtain 0.74 parts (yield 75%) of the compound represented by formula (A-19).

[Synthesis Example 18]
The same procedure as in Synthesis Example 3 was conducted except that bis(trifluoromethanesulfonyl)lithium was changed to N,N-bis(2-hydroxyethyl)-2-aminoethanesulfonic acid, to obtain 0.87 parts (yield 87%) of the compound represented by formula (A-20).

Synthesis Example 19
The same procedure as in Synthesis example 3 was conducted except that bis(trifluoromethanesulfonyl)lithium was changed to monosodium iron(III) ethylenediaminetetraacetate hydrate, to obtain 0.65 parts (yield 60%) of the compound represented by formula (A-21).

[Synthesis Example 20]
The same procedure as in Synthesis Example 3 was repeated except that bis(trifluoromethanesulfonyl)lithium was changed to sodium vinylsulfonate, to obtain 0.65 parts (yield 74%) of the compound represented by formula (A-22).

[Synthesis Example 21]
The same procedure as in Synthesis example 3 was repeated except that bis(trifluoromethanesulfonyl)lithium was changed to a 3-(trihydroxysilyl)propylmethylphosphonate monosodium salt solution, to obtain 0.47 parts (yield 46%) of the compound represented by formula (A-23).

Synthesis Example 22
The same procedure as in Synthesis Example 3 was repeated except that bis(trifluoromethanesulfonyl)lithium was changed to 3-(trihydroxysilyl)propane-1-sulfonic acid, to obtain 0.32 parts (yield 36%) of the xanthene compound represented by formula (A-24).

Synthesis Example 23
0.2 parts of 1,8-naphthosultone, 0.2 parts of 3-aminopropyltriethoxysilane, and 8.5 parts of dimethyl sulfoxide were mixed and stirred at room temperature for 3 hours to obtain a compound represented by formula (B-5). Then, 0.78 parts of a compound represented by formula (A-25) (yield 93%) was obtained in the same manner as in Synthesis Example 3, except that bis(trifluoromethanesulfonyl)lithium was replaced with the compound represented by formula (B-5).

Synthesis Example 24
The same procedure as in Synthesis Example 23 was conducted except that 1,8-naphthosultone was changed to sodium 1,8-naphthosultone-4-sulfonate, to obtain 0.5 parts of the compound represented by formula (A-26) (yield 44%).

Synthesis Example 25
The same procedure as in Synthesis Example 3 was conducted except that bis(trifluoromethanesulfonyl)lithium was changed to phosphotungstic acid hydrate, to obtain 0.5 parts of the compound represented by the formula (A-27) (yield 72%).

Synthesis Example 26
The same procedure as in Synthesis Example 3 was repeated except that bis(trifluoromethanesulfonyl)lithium was changed to 1,1,2,2,3,3-hexafluoropropane-1,3-disulfonimide lithium, to obtain 0.69 parts (yield 63%) of the xanthene compound represented by formula (A-28).

Synthesis Example 27
The same procedure as in Synthesis Example 3 was repeated except that bis(trifluoromethanesulfonyl)lithium was changed to potassium tris(trifluoromethanesulfonyl)methanide, to obtain 0.63 parts (yield 58%) of the compound represented by formula (A-29).

[Preparation of Dispersion 1]
10.0 parts of C.I. Pigment Red 291 (pigment), 3.3 parts of dispersant (BYK BYKLPN-6919; propylene glycol monomethyl ether acetate 60% solution), 4.0 parts of resin (B-2) (solid content equivalent), 12.7 parts of propylene glycol monomethyl ether were mixed, 41.3 parts of propylene glycol monomethyl ether acetate was mixed, 600 parts of 0.4 μm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (LAU). The zirconia beads were then removed by filtration to obtain dispersion 1.

[Preparation of Dispersion 2]
10.0 parts of C.I. Pigment Red 177 (pigment), 4.3 parts of dispersant (BYK BYKLPN-6919; propylene glycol monomethyl ether acetate 60% solution), 4.0 parts of resin (B-2) (solid content equivalent), and 59.2 parts of propylene glycol monomethyl ether acetate were mixed, 600 parts of 0.4 μm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (LAU). The zirconia beads were then removed by filtration to obtain dispersion 2.

[Preparation of Dispersion 3]
10.0 parts of C.I. Pigment Red 202 (pigment), 7.5 parts of dispersant (BYK BYKLPN-6919; propylene glycol monomethyl ether acetate 60% solution), 3.5 parts of resin (B-2) (solid content equivalent), 8.5 parts of propylene glycol monomethyl ether, and 202 parts of propylene glycol monomethyl ether acetate were mixed, and 600 parts of 0.4 μm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (LAU). Thereafter, the zirconia beads were removed by filtration to obtain dispersion 3.

[Preparation of Dispersion 4]
10.0 parts of C.I. Pigment Red 264 (pigment), 7.6 parts of dispersant (BYK BYKLPN-6919; propylene glycol monomethyl ether acetate 60% solution), 3.6 parts of resin (B-2) (solid content equivalent), 6.7 parts of propylene glycol monomethyl ether, and 55.4 parts of propylene glycol monomethyl ether acetate were mixed, and 600 parts of 0.4 μm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (LAU). The zirconia beads were then removed by filtration to obtain dispersion 4.

[Preparation of Dispersion 5]
10.0 parts of C.I. Pigment Red 269 (pigment), 5.0 parts of dispersant (BYK BYKLPN-6919; propylene glycol monomethyl ether acetate 60% solution), 3.0 parts of resin (B-2) (solid content equivalent), 5.5 parts of propylene glycol monomethyl ether, and 47.7 parts of propylene glycol monomethyl ether acetate were mixed, and 600 parts of 0.4 μm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (LAU). Thereafter, the zirconia beads were removed by filtration to obtain dispersion 5.

[Preparation of Dispersion 6]
10.0 parts of C.I. Pigment Yellow 185 (pigment), 10.8 parts of dispersant (BYK BYKLPN-6919; propylene glycol monomethyl ether acetate 60% solution), 3.5 parts of resin (B-2) (solid content equivalent), 4.2 parts of propylene glycol monomethyl ether, and 96.5 parts of propylene glycol monomethyl ether acetate were mixed, and 600 parts of 0.4 μm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (LAU). The zirconia beads were then removed by filtration to obtain dispersion 6.

[Preparation of Dispersion 7]
10.0 parts of C.I. Pigment Blue 15:6 (pigment), 5.8 parts of dispersant (BYK BYKLPN-6919; propylene glycol monomethyl ether acetate 60% solution), 4.0 parts of resin (B-2) (solid content equivalent), 7.6 parts of ethyl lactate, and 96.5 parts of propylene glycol monomethyl ether acetate were mixed, and 600 parts of 0.4 μm zirconia beads were added, and the mixture was shaken for 1 hour using a paint conditioner (LAU). The zirconia beads were then removed by filtration to obtain dispersion 7.

<Examples 1 to 36, Comparative Examples 1 and 2>
[Preparation of Colored Resin Composition]
The components shown in Tables 5 to 7 were mixed to obtain each colored resin composition.

- Colorant 1: Compound represented by formula (A-1)

Colorant 2: Compound represented by formula (A-2)

Colorant 3: Compound represented by formula (A-3)

- Colorant 4: Compound represented by formula (A-4)

Colorant 5: Compound represented by formula (A-X)

Colorant 6: Compound represented by formula (A-6) Colorant 7: Compound represented by formula (A-7) Colorant 8: Compound represented by formula (A-8) Colorant 9: Compound represented by formula (A-9) Colorant 10: Compound represented by formula (A-10) Colorant 11: Compound represented by formula (A-11) Colorant 12: Compound represented by formula (A-12) Colorant 13: Compound represented by formula (A-13) Colorant 14: Compound represented by formula (A-14) Colorant 15: Compound represented by formula (A-15) Colorant 16: Compound represented by formula (A-16) Colorant 17: Compound represented by formula (A-17) Colorant 1 Colorant 8: Compound represented by formula (A-18) Colorant 19: Compound represented by formula (A-19) Colorant 20: Compound represented by formula (A-20) Colorant 21: Compound represented by formula (A-21) Colorant 22: Compound represented by formula (A-22) Colorant 23: Compound represented by formula (A-23) Colorant 24: Compound represented by formula (A-24) Colorant 25: Compound represented by formula (A-25) Colorant 26: Compound represented by formula (A-26) Colorant 27: Compound represented by formula (A-27) Colorant 28: Compound represented by formula (A-28) Colorant 29: Compound represented by formula (A-29)

Resin (B): Resin (B-1) (solid content equivalent)
Polymerizable compound (C): dipentaerythritol hexaacrylate (KAYARAD (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.)
・Polymerization initiator (D): TR-PBG327 (registered trademark) (manufactured by Changzhou Strong Electronics New Materials Co., Ltd.; oxime compound)
Solvent (E): Solvent (E-1): Ethyl lactate
Solvent (E-2): Diacetone alcohol
Solvent (E-3): Propylene glycol monomethyl ether acetate Leveling agent (F): Polyether modified silicone oil (solid content equivalent) (TORAY SILICONE SH8400; manufactured by Dow Corning Toray Co., Ltd.)

[Preparation of color filters (colored coating films)]
The colored resin composition was applied by spin coating onto a 5 cm square glass substrate (Eagle 2000; Corning Incorporated), and then prebaked at 100°C for 3 minutes to form a colored resin composition layer. After cooling, the substrate was irradiated with light at an exposure dose of 60 mJ/ ^cm2 (based on 365 nm) in an air atmosphere using an exposure machine (TME-150RSK; Topcon Corporation). Then, the substrate was postbaked in an oven at 230°C for 20 minutes to obtain a color filter.

[Chemical resistance test]
The obtained color filter was immersed in N-methylpyrrolidone adjusted to 40° C. for 10 minutes. The color filter before and after immersion was measured for spectroscopy using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and the xy chromaticity coordinates (x, y) and stimulus value Y in the CIE XYZ color system were calculated using the characteristic function of the C light source. From the measured values, the color difference ΔE*ab was calculated according to the method described in JIS Z 8730:2009 (7. Calculation method of color difference), and the results are shown in Tables 8 to 9. The smaller ΔE*ab means the smaller the color change.

Claims (5)

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

[In formula (I),
R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R ⁷ , R ⁸ , R ⁹ and R ¹⁰ each independently represent a hydrogen atom, a hydroxy group, a nitro group, a cyano group, a halogen atom, a carboxy group, a sulfo group, a sulfamoyl group, a metallocenyl group, a hydrocarbon group having 1 to 30 carbon atoms, or a group in which one or more methylene groups in the hydrocarbon group have been replaced with a divalent group selected from Group I below, with the proviso that when two or more methylene groups have been replaced with a divalent group selected from Group I below, the divalent groups are not adjacent to each other,
a hydrogen atom contained in the hydrocarbon group may be substituted with a halogen atom, a nitro group, a cyano group, a hydroxy group, an amino group, a carboxy group, a sulfo group, a phosphono group, a sulfamoyl group, an isocyanato group, or a heterocycle;
R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ each independently represent a hydrogen atom, a hydrocarbon group having 1 to 30 carbon atoms, or a group in which one or more methylene groups in the hydrocarbon group have been replaced with a divalent group selected from the following group I, with the proviso that when two or more methylene groups have been replaced with a divalent group selected from the following group I, the divalent groups are not adjacent to each other:
A hydrogen atom contained in the hydrocarbon group may be substituted with a heterocyclic ring or a polar group,
one or more of R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ¹⁵ and R ¹⁶ is a group having a polar group as a substituent;
The group having a polar group as a substituent is one or more of groups represented by the following formulas (po-1) to (po-10) :

n represents an integer of 1 to 3;
A ^q- represents a q-valent anion;
q represents an integer of 1 to 3;
p represents a coefficient for keeping the charge of the compound represented by formula (I) neutral.
Group I: -O-, -S-, -CO-, -COO-, -OCO-, -COS-, -OCS-, -SO ₂ -, -SO ₃ -, -NH-, -CONH-, -NHCO-, -SO ₂ NH-, -NHSO ₂ - or -N=CH-] The colored resin composition according to claim 1, further comprising a polymerizable compound and a polymerization initiator. The colored resin composition according to claim 1 or 2, wherein the colorant further comprises a pigment (excluding the compound represented by formula (I)). A color filter formed from the colored resin composition according to any one of claims 1 to 3. A display device including the color filter according to claim 4.