JP2020024448A - Colored curable resin composition - Google Patents

Abstract

To obtain a color filter excellent in a pattern shape.SOLUTION: There is provided a colored curable resin composition comprising: a coloring agent; a resin; a polymerizable compound; and a polymerization initiator, in which the coloring agent is formed of a dye and a pigment, and the polymerization initiator comprises a compound expressed by the formula (d1).SELECTED DRAWING: None

Description

  The present invention relates to a colored curable resin composition.

The colored curable resin composition is used for producing a color filter used for a display device such as a liquid crystal display device, an electroluminescence display device, and a plasma display. As such a colored curable resin composition, a colored curable resin composition containing N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine as an initiator is known. (Patent Document 1).
An oxime ester derivative of a benzocarbazole compound has been proposed as a highly sensitive photoinitiator in a photopolymerizable composition (Patent Document 2).

JP 2010-32999 A JP 2014-500852 A

  An object of the present invention is to obtain a color filter having an excellent pattern shape.

［式（ｄ１）中、
Ｒ^d1は、置換基を有していてもよい炭素数６〜１８の芳香族炭化水素基、置換基を有していてもよい炭素数３〜３６の複素環基、置換基を有していてもよい炭素数１〜１５のアルキル基、又は置換基を有していてもよい炭素数７〜３３のアラルキル基を表し、前記アルキル基又はアラルキル基に含まれるメチレン基（−ＣＨ₂−）は、−Ｏ−、−ＣＯ−、
−Ｓ−、−ＳＯ₂−又は−Ｎ（Ｒ^d5）−に置き換わっていてもよい。
Ｒ^d2は、炭素数６〜１８の芳香族炭化水素基、炭素数３〜３６の複素環基、又は炭素数１〜１０のアルキル基を表す。
Ｒ^d3は、置換基を有していてもよい炭素数６〜１８の芳香族炭化水素基、又は置換基を
有していてもよい炭素数３〜３６の複素環基を表す。
Ｒ^d4は、置換基を有していてもよい炭素数６〜１８の芳香族炭化水素基、又は置換基を有していてもよい炭素数１〜１５の脂肪族炭化水素基を表し、前記脂肪族炭化水素基に含まれるメチレン基（−ＣＨ₂−）は、−Ｏ−、−ＣＯ−又は−Ｓ−に置き換わっていても
よく、前記脂肪族炭化水素基に含まれるメチン基（−ＣＨ＜）は、−ＰＯ₃＜に置き換わ
っていてもよく、前記脂肪族炭化水素基に含まれる水素原子はＯＨ基で置換されていてもよい。
Ｒ^d5は、炭素数１〜１０のアルキル基を表し、該アルキル基に含まれるメチレン基（−ＣＨ₂−）は、−Ｏ−又は−ＣＯ−に置き換わっていてもよい。］
［２］前記染料が、キサンテン染料、トリアリールメタン染料、式（Ａｂ２）で表される化合物及びクマリン染料からなる群から選ばれる少なくとも一種の染料を含む［１］に記載の着色硬化性樹脂組成物。

［式（Ａｂ２）中、Ｒ⁴¹〜Ｒ⁴⁴は、それぞれ独立して、水素原子、炭素数１〜２０の飽和炭化水素基、置換基を有していてもよい炭素数６〜２０の芳香族炭化水素基又は置換基を有していてもよい炭素数７〜３０のアラルキル基を表し、該炭素数１〜２０の飽和炭化水素基において、該飽和炭化水素基に含まれる水素原子は、置換若しくは非置換のアミノ基又はハロゲン原子に置換されていてもよく、該飽和炭化水素基の炭素数が２〜２０である場合、該飽和炭化水素基に含まれるメチレン基は酸素原子又は−ＣＯ−に置換されていてもよい。Ｒ⁴¹とＲ⁴²とが結合してそれらが結合する窒素原子とともに環を形成してもよく、Ｒ⁴³とＲ⁴⁴とが結合してそれらが結合する窒素原子とともに環を形成してもよい。
Ｒ⁴⁷〜Ｒ⁵⁴は、それぞれ独立して、水素原子、ハロゲン原子、ニトロ基、ヒドロキシ基、又は炭素数１〜８のアルキル基を表し、該アルキル基の炭素数が２〜８である場合、該アルキル基を構成するメチレン基は酸素原子又は−ＣＯ−に置換されていてもよく、Ｒ⁴⁸とＲ⁵²とが互いに結合して、−ＮＨ−、−Ｓ−又はＳＯ₂−を形成していてもよい。
環Ｔ¹は、置換基を有していてもよい炭素数３〜１０の芳香族複素環を表す。
［Ｙ］^m-は、任意のｍ価のアニオンを表す。
ｍは任意の自然数を表す。］
［３］前記着色剤として、フタロシアニン顔料を含む［１］又は［２］に記載の着色硬化性樹脂組成物。
［４］顔料の含有率が、固形分の総量に対して、１質量％以上、５０質量％以下である［１］〜［３］のいずれかに記載の着色硬化性樹脂組成物。
［５］重合開始剤と重合性化合物との含有量比（重合開始剤／重合性化合物）が、質量基準で、４／１０００以上、３５／１００以下である［１］〜［４］のいずれかに記載の着色硬化性樹脂組成物。
［６］［１］〜［５］のいずれかに記載の着色硬化性樹脂組成物から形成されるカラーフィルタ。
［７］［６］に記載のカラーフィルタを含む液晶表示装置。 The present invention includes the following inventions.
[1] containing a colorant, a resin, a polymerizable compound and a polymerization initiator,
Including a dye and a pigment as the colorant,
A colored curable resin composition wherein the polymerization initiator contains a compound represented by the following formula (d1).

[In the formula (d1),
R ^d1 represents an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, a heterocyclic group having 3 to 36 carbon atoms which may have a substituent, or a substituent. Represents an alkyl group having 1 to 15 carbon atoms which may be substituted or an aralkyl group having 7 to 33 carbon atoms which may have a substituent, and a methylene group (—CH ₂ —) included in the alkyl group or the aralkyl group Is -O-, -CO-,
—S—, —SO ₂ — or —N (R ^d5 ) — may be substituted.
R ^d2 represents an aromatic hydrocarbon group having 6 to 18 carbon atoms, a heterocyclic group having 3 to 36 carbon atoms, or an alkyl group having 1 to 10 carbon atoms.
R ^d3 represents an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, or a heterocyclic group having 3 to 36 carbon atoms which may have a substituent.
R ^d4 represents an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, or an aliphatic hydrocarbon group having 1 to 15 carbon atoms which may have a substituent; a methylene group contained in the aliphatic hydrocarbon group (-CH ₂ -) is, -O -, - CO- or -S- may be replaced, a methine group (-CH contained in the aliphatic hydrocarbon group <) May be replaced by —PO ₃ <, and a hydrogen atom contained in the aliphatic hydrocarbon group may be replaced by an OH group.
R ^d5 represents an alkyl group having 1 to 10 carbon atoms, and the methylene group (—CH ₂ —) contained in the alkyl group may be replaced by —O— or —CO—. ]
[2] The colored curable resin composition according to [1], wherein the dye contains at least one dye selected from the group consisting of a xanthene dye, a triarylmethane dye, a compound represented by the formula (Ab2), and a coumarin dye. object.

[In the formula (Ab2), R ^{41 to} R ⁴⁴ each independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aromatic group having 6 to 20 carbon atoms which may have a substituent. Represents a hydrocarbon group or an aralkyl group having 7 to 30 carbon atoms which may have a substituent, and in the saturated hydrocarbon group having 1 to 20 carbon atoms, a hydrogen atom contained in the saturated hydrocarbon group is substituted. Alternatively, it may be substituted with an unsubstituted amino group or a halogen atom, and when the saturated hydrocarbon group has 2 to 20 carbon atoms, the methylene group contained in the saturated hydrocarbon group is an oxygen atom or -CO- May be substituted. R ⁴¹ and R ⁴² may combine to form a ring together with the nitrogen atom to which they bind, or R ⁴³ and R ⁴⁴ may combine to form a ring together with the nitrogen atom to which they bind.
R ^{47 to} R ⁵⁴ each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, or an alkyl group having 1 to 8 carbon atoms, and when the alkyl group has 2 to 8 carbon atoms, methylene group constituting the alkyl group may be substituted by an oxygen atom or a -CO-, linked with R ⁴⁸ and R ⁵² each other, -NH -, - S- or SO ₂ - have the form You may.
Ring T ¹ represents an aromatic heterocyclic ring having 3 to 10 carbon atoms which may have a substituent.
[Y] ^m- represents an arbitrary m-valent anion.
m represents an arbitrary natural number. ]
[3] The colored curable resin composition according to [1] or [2], containing a phthalocyanine pigment as the colorant.
[4] The colored curable resin composition according to any one of [1] to [3], wherein the content of the pigment is 1% by mass or more and 50% by mass or less based on the total amount of solids.
[5] Any one of [1] to [4], wherein the content ratio of the polymerization initiator and the polymerizable compound (polymerization initiator / polymerizable compound) is 4/1000 or more and 35/100 or less on a mass basis. A colored curable resin composition according to any one of the above.
[6] A color filter formed from the colored curable resin composition according to any one of [1] to [5].
[7] A liquid crystal display device including the color filter according to [6].

  According to the colored curable resin composition of the present invention, a color filter having an excellent pattern shape can be formed.

FIG. 1 is a schematic diagram illustrating a cross-sectional shape of a coloring pattern. FIG. 2 is a schematic diagram illustrating a cross-sectional shape of a coloring pattern.

The colored curable resin composition of the present invention contains a colorant (A), a resin (B), a polymerizable compound (C), and a polymerization initiator (D).
In the present specification, compounds exemplified as each component can be used alone or in combination of two or more, unless otherwise specified.

<Colorant (A)>
The colored curable resin composition of the present invention contains a dye and a pigment as the colorant (A).
The dye is at least one dye selected from the group consisting of a xanthene dye (Aa), a triarylmethane dye (Ab), a compound represented by the formula (Ab2), and a coumarin dye (Ac) (hereinafter, “dye (A1) "In some cases), and more preferably contains a xanthene dye (Aa).
In the present specification, a dye refers to a dye that is soluble in a solvent.

  The xanthene dye (Aa) is a dye containing a compound having a xanthene skeleton in the molecule. Examples of the xanthene dye (Aa) include C.I. I. Acid Red 51 (hereinafter, CI Acid Red is omitted, and only the number is described. Others are the same), 52, 87, 92, 94, 289, 388, and the like. I. Acid red dye; C.I. I. Acid Violet 9, 30, 102 and the like. I. Acid violet dye; C.I. I. Basic Red 1 (rhodamine 6G), 2, 3, 4, 8, 10 (rhodamine B), C.I. I. Basic red dye; C.I. I. Basic violet 10, 11, 25 and the like. I. Basic violet dye; C.I. I. Solvent Red 218 and the like. I. Solvent red dye; C.I. I. C. such as Modant Red 27; I. Modant red dye; C.I. I. C. Reactive Red 36 (Rose Bengal B) and the like. I. Reactive red dye; sulforhodamine G; a xanthene dye described in JP-A-2010-32999; and a xanthene dye described in Japanese Patent No. 4492760. As the xanthene dye (Aa), those which dissolve in an organic solvent are preferable.

  Among these, as the xanthene dye (Aa), a dye containing a compound represented by the formula (1a) (hereinafter sometimes referred to as “compound (1a)”) is preferable. Compound (1a) may be a tautomer thereof. When the compound (1a) is used, the content of the compound (1a) in the xanthene dye (Aa) is preferably 50% by mass or more, more preferably 70% by mass or more, and further preferably 90% by mass or more. In particular, it is preferable to use only the compound (1a) as the xanthene dye (Aa).

[In the formula (1a), R ^{1 to} R ⁴ independently represent a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a substituent. Represents a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms which may be a methylene group (—CH ₂ —) contained in the saturated hydrocarbon group.
Is, -O -, - CO- or -N (R ¹¹⁾ - may be replaced by. R ¹ and R ² may together form a ring containing a nitrogen atom, and R ³ and R ⁴ may together form a ring containing a nitrogen atom.
R ^{5 _{is, -OH, -SO 3 -, -SO}} 3 H, -SO 3 - Z +, -CO 2 H, -CO 2 - Z +, -C
O ₂ R ⁸ , —SO ₃ R ⁸ or —SO ₂ N (R ⁹ ) (R ¹⁰ ).
R ⁶ and R ⁷ independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
m represents an integer of 0 to 5. When m is 2 or more, a plurality of R ⁵ may be the same or different.
a represents an integer of 0 or 1.
X represents a halogen atom.
Z ⁺ represents ⁺ N (R ¹¹ ) ₄ , Na ⁺ or K ⁺ , and the four R ¹¹ may be the same or different.
R ⁸ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom.
R ⁹ and R ¹⁰ each independently represent a hydrogen atom or an optionally substituted carbon group having 1 to 2 carbon atoms.
0 represents a monovalent saturated hydrocarbon group, and -CH _2- contained in the saturated aliphatic hydrocarbon group is-
O—, —CO—, —NH— or —N (R ⁸ ) — may be replaced, and R ⁹ and R ¹⁰ are bonded to each other to form a 3- to 10-membered heterocyclic ring containing a nitrogen atom. It may be formed.
R ¹¹ represents a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or an aralkyl group having 7 to 10 carbon atoms. ]

In formula (1a), -SO ₃ ^- if there is, the number is one.

Examples of the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms in R ^{1 to} R ⁴ include a phenyl group, a toluyl group, a xylyl group, a mesityl group, a propylphenyl group and a butylphenyl group.

The aromatic hydrocarbon group substituent which may have a halogen atom, -R ^8, -O
_{^{H, -OR 8, -SO 3 -}} , -SO 3 H, -SO 3 - Z +, -CO 2 H, -CO 2 R 8, -SR 8,
—SO ₂ R ⁸ , —SO ₃ R ⁸ or —SO ₂ N (R ⁹ ) (R ¹⁰ ). These substituents may substitute a hydrogen atom contained in the aromatic hydrocarbon group. preferable. Among them, as the _{^{substituent, -SO 3 -, -SO 3 H}} , -SO 3 - Z +, -SO 3 R 8 and ^{_{-SO 2 N (R 9) (}} R 10) is preferably, -SO ₃ ^- Z ⁺ and ^{_{-SO 2 N (R 9) (}} R 10) is more preferable. -SO ₃ in this case ^- Z ^{+ _{The, -SO 3 - + N (R}} 11) 4 are preferred. Also, -SO ₂ N (R ⁹ )
(R ¹⁰ ) is preferably —SO ₂ NHR ⁹ . When R ^{1 to} R ⁴ are these groups, a color filter with less generation of foreign matters and excellent heat resistance can be formed from the colored curable resin composition of the present invention containing the compound (1a).

Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in R ^{1 to} R ⁴ and R ^{8 to} R ¹¹ include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group and a heptyl group. Linear alkyl groups such as octyl group, nonyl group, decyl group, dodecyl group, hexadecyl group and icosyl group; branched chain alkyl groups such as isopropyl group, isobutyl group, isopentyl group, neopentyl group and 2-ethylhexyl group; Examples thereof include a cyclic alkyl group having 3 to 20 carbon atoms such as a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and a tricyclodecyl group.
The hydrogen atom contained in the saturated hydrocarbon group in R ^{1 to} R ⁴ may be substituted with, for example, an aromatic hydrocarbon group having 6 to 10 carbon atoms or a halogen atom as a substituent. The aromatic hydrocarbon group having 6 to 10 carbon atoms which may substitute a hydrogen atom of the saturated hydrocarbon group for R ^{1 to} R ⁴ includes an aromatic hydrocarbon group having 6 to 10 carbon atoms for R ^{1 to} R ⁴ . The same groups as the groups exemplified as the groups are exemplified.
The hydrogen atom contained in the saturated hydrocarbon group in R ⁹ and R ¹⁰ may be substituted with, for example, a hydroxy group or a halogen atom as a substituent.

The ring formed by R ¹ and R ² together and the ring formed by R ³ and R ⁴ together include, for example, the following, and those containing no double bond are more preferable. .

Examples of -OR ⁸ include alkyloxy groups such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy, and icosyloxy groups. Is mentioned.

Examples of —CO ₂ R ⁸ include an alkyloxycarbonyl group such as a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a hexyloxycarbonyl group, and an icosyloxycarbonyl group.

Examples of -SR ⁸ include alkylsulfanyl groups such as methylsulfanyl group, ethylsulfanyl group, butylsulfanyl group, hexylsulfanyl group, decylsulfanyl group and icosylsulfanyl group.
Examples of —SO ₂ R ⁸ include an alkylsulfonyl group such as a methylsulfonyl group, an ethylsulfonyl group, a butylsulfonyl group, a hexylsulfonyl group, a decylsulfonyl group, and an icosylsulfonyl group.
Examples of —SO ₃ R ⁸ include an alkyloxysulfonyl group such as a methoxysulfonyl group, an ethoxysulfonyl group, a propoxysulfonyl group, a tert-butoxysulfonyl group, a hexyloxysulfonyl group, and an icosyloxysulfonyl group. −SO ₃
As R ⁸ of R ⁸ , a branched alkyl group having 3 to 20 carbon atoms is preferable, a branched alkyl group having 6 to 12 carbon atoms is more preferable, and a 2-ethylhexyl group is further preferable. It is possible to form a color filter with less generation of foreign matter.

—SO ₂ N (R ⁹ ) (R ¹⁰ ) includes, for example, a sulfamoyl group;
N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N- sec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N- (1-ethylpropyl) sulfamoyl group, N- (1,1-dimethylpropyl) sulfamoyl group, N- (1,2-dimethylpropyl) sulfamoyl group, N- (2,2-dimethylpropyl) sulfamoyl group, N- (1-methylbutyl) sulfamoyl group, N- (2-methylbutyl) sulfamoyl group, N- (3 -Methylbutyl) sulfamoyl group, N-cyclopentylsulfamoyl group, N-hexylsulfamoyl , N- (1,3-dimethylbutyl) sulfamoyl group, N- (3,3-dimethylbutyl) sulfamoyl group, N-heptylsulfamoyl group, N- (1-methylhexyl) sulfamoyl group, N- (1 , 4-Dimethylpentyl) sulfamoyl group, N-octylsulfamoyl group, N- (2-ethylhexyl) sulfamoyl group, N- (1,5-dimethylhexyl) sulfamoyl group, N- (1,1,2,2 N-1-substituted sulfamoyl groups such as -tetramethylbutyl) sulfamoyl group;
N, N-dimethylsulfamoyl, N, N-ethylmethylsulfamoyl, N, N-diethylsulfamoyl, N, N-propylmethylsulfamoyl, N, N-isopropylmethylsulfamo Moyl group, N, N-tert-butylmethylsulfamoyl group, N, N-butylethylsulfamoyl group, N, N-bis (1-methylpropyl) sulfamoyl group, N, N-heptylmethylsulfamoyl And N, N-2-substituted sulfamoyl groups and the like.
In the N-1-substituted sulfamoyl group, R ⁸ is preferably a branched alkyl group having 3 to 20 carbon atoms, more preferably a branched alkyl group having 6 to 12 carbon atoms, and still more preferably a 2-ethylhexyl group. . It is possible to form a color filter with less generation of foreign matter.

The _{^{R 5, -CO 2 H, -CO}} 2 - Z +, -CO 2 R 8, -SO 3 -, -SO 3 - Z +, -SO 3 H or -SO ₂ NHR ⁹ are preferred, -SO ^{_{3 -, -SO 3 - Z +}} , -SO 3 H or -SO ₂ NHR ⁹ is more preferable.
m is preferably 1 to 4, more preferably 1 or 2.

Examples of the alkyl group having 1 to 6 carbon atoms in R ⁶ and R ⁷ include those having 1 to 6 carbon atoms among the above-mentioned alkyl groups. Above all, a hydrogen atom is preferable as R ⁶ and R ⁷ .

The aralkyl group having 7 to 10 carbon atoms in R ^11, benzyl group, phenylethyl group, and a phenyl butyl group.
R ¹¹ is preferably a saturated hydrocarbon group having 1 to 20 carbon atoms or a benzyl group.

Z ⁺ is ⁺ N (R ¹¹ ) ₄ , Na ⁺ or K ⁺ , preferably ⁺ N (R ¹¹ ) ₄ .
As ⁺ N (R ¹¹ ) ₄ , at least two of the four R ¹¹ are preferably a monovalent saturated hydrocarbon group having 5 to 20 carbon atoms. Further, the total carbon number of the four R ¹¹ is preferably 20 to 80, more preferably 20 to 60. When ⁺ N (R ¹¹ ) ₄ is present in compound (1a) and R ¹¹ is one of these groups, the color curable resin composition of the present invention containing compound (1a) contains a color filter containing less foreign matter. Can be formed.
m is preferably 1 to 4, more preferably 1 or 2.

As a combination of R ^{1 to} R ^4, a combination in which R ¹ and R ³ are a hydrogen atom and R ² and R ⁴ are an aromatic hydrocarbon group having a monovalent substituent having 6 to 10 carbon atoms is preferable. . The substituent of the aromatic hydrocarbon _{^{group, -SO 3 -, -SO 3 H}} , -SO 3 - Z +, -SO 3 R 8 or -SO ₂ N
HR ⁹ are preferred, -SO ₃ ^- Z ⁺ or -SO ₂ NHR ⁹ is more preferable. These substituents replace a hydrogen atom contained in the aromatic hydrocarbon group.

As a combination of R ^{1 to} R ^4, a combination in which R ^{1 to} R ⁴ are all monovalent saturated hydrocarbon groups is also preferable. In this case, the saturated hydrocarbon group is preferably a methyl group or an ethyl group.

Further, as a combination of R ^{1 to} R ⁴ , R ¹ and R ³ are a saturated hydrocarbon group having 1 to 10 carbon atoms which may have a substituent, and R ² and R ⁴ have a substituent. Combinations which are optionally phenyl groups are also preferred.
In this case, R ¹ may form a ring with a substituent that substitutes the phenyl group of R ² , and R ³ is
A ring may be formed with a substituent that substitutes the phenyl group of R ⁴ .
Moreover, it is preferable that R1 and R3 have ^{1 to 3} carbon atoms independently of each other. As the substituent of the hydrogen atom contained in the saturated hydrocarbon group of R ¹ and R ³ , an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with an alkoxy group having 1 to 3 carbon atoms, or a halogen atom Atoms are preferred.
Examples of the substituent that the phenyl group of R ² and R ⁴ may have include an alkyl group having 1 to 4 carbon atoms, an alkylsulfanyl group having 1 to 4 carbon atoms, and an alkylsulfonyl group having 1 to 4 carbon atoms. Is preferable, an alkyl group having 1 to 4 carbon atoms is more preferable, and a methyl group is further preferable. The number of substituents for substituting the phenyl group of R ² and R ⁴ is 0 to 5, preferably 0 to 2, and more preferably 0 or 1.
Examples of the alkyl group having 1 to 4 carbon atoms which may substitute the phenyl group for R ² and R ⁴ include a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, a sec-butyl group and a tert group. -Butyl group and the like.
Examples of the alkylsulfanyl group having 1 to 4 carbon atoms which may substitute the phenyl group for R ² and R ⁴ include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, a butylsulfanyl group, and an isopropylsulfanyl group. No.
Examples of the alkylsulfonyl group having 1 to 4 carbon atoms which may substitute the phenyl group for R ² and R ⁴ include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, and an isopropylsulfonyl group. No.

Examples of the compound (1a) include compounds represented by the formulas (1-1) to (1-43). In the formula, R ⁴⁰ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, preferably a branched alkyl group having 6 to 12 carbon atoms, and more preferably a 2-ethylhexyl group.

The xanthene dye (Aa) further includes a compound having a structure in which an aromatic heterocycle having 3 to 9 carbon atoms is bonded to the 9-position carbon of the xanthene ring. The aromatic heterocyclic ring may have a substituent.
Examples of the xanthene dye (Aa) include compounds represented by Formulas (1-1) to (1-8); I. Acid Red 289 quaternary ammonium salt (for example, a compound represented by Formula (1-11) or Formula (1-12)), C.I. I. Acid Violet 102 sulfonamide and C.I. I. A quaternary ammonium salt of Acid Violet 102 is preferable, and compounds represented by the formulas (1-1) to (1-8), and compounds represented by the formulas (1-11) and (1-12) Is preferred.
Further, a compound represented by any of formulas (1-24) to (1-33) is also preferable in terms of excellent solubility in an organic solvent.

  As the xanthene dye (Aa), commercially available xanthene dyes (for example, “Chugai Aminol Fast Pink RH / C” manufactured by Chugai Kasei Co., Ltd. and “Rhodamin 6G” manufactured by Taoka Chemical Industry Co., Ltd.) can be used. it can. Further, it can be synthesized by using a commercially available xanthene dye as a starting material with reference to JP-A-2010-32999.

  The content of the xanthene dye (Aa) is preferably at least 50 parts by mass, more preferably at least 80 parts by mass, further preferably at least 90 parts by mass, particularly preferably at least 99 parts by mass, per 100 parts by mass of the dye (A1). Or more, and preferably 100 parts by mass or less.

The triarylmethane dye (Ab) is a dye containing a compound having a structure in which three aromatic groups are bonded to one carbon atom. Specific examples of the aromatic group include an aromatic hydrocarbon group.
Examples of the triarylmethane dye (Ab) include C.I. I. Solvent Blue 2, 4, 5, 43, 124; I. Basic Violet 3, 14, 25; C.I. I. Basic Blue 1, 5, 7, 11, 26 and the triarylmethane dyes described in Japanese Patent No. 4492760. Those that dissolve in an organic solvent are preferred.

  Among these, as the triarylmethane dye (Ab), a dye containing a compound represented by the formula (Ab1) (hereinafter sometimes referred to as “compound (Ab1)”) is preferable.

[In the formula (Ab1), R ^{1A to} R ^8A each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, or a saturated hydrocarbon group having 1 to 20 carbon atoms. When the number of carbon atoms is 2 to 20, the methylene group constituting the saturated hydrocarbon group may be substituted with an oxygen atom or -CO-.
R ^{9A to} R ^12A each independently have a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent or a substituent. Represents an aralkyl group having 7 to 30 carbon atoms which may be substituted, and a hydrogen atom contained in the saturated hydrocarbon group may be substituted with a substituted or unsubstituted amino group or a halogen atom; When the group has 2 to 20 carbon atoms, the methylene group contained in the saturated hydrocarbon group may be substituted with an oxygen atom or -CO-. R ^9A and R ^10A may be bonded to form a ring together with the nitrogen atom to which they are bonded, or R ^11A and R ^12A may be bonded to form a ring together with the nitrogen atom to which they are bonded.
A represents an optionally substituted aromatic hydrocarbon group having 6 to 20 carbon atoms.
[G] ^g- represents an arbitrary g-valent counter anion. g represents 0 or any natural number. ]
In addition, in Formula (Ab1), when g is a natural number of 2 or more, the cations in Formula (Ab1) may have the same structure or different structures.

The saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^{1A to} R ^12A may be any of linear, branched and cyclic, and is preferably a chain. The saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^1A to R ^12A, include the same groups exemplified as a saturated hydrocarbon group R ^1. The saturated hydrocarbon group represented by R ^{1A to} R ^12A preferably has 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms.

When the saturated hydrocarbon group represented by R ^{1A to} R ^12A has 2 to 20 carbon atoms, the methylene group contained in the saturated hydrocarbon group may be substituted with an oxygen atom or -CO-, Preferably, it may be substituted by an oxygen atom. Further, an oxygen atom may be inserted between methylene groups constituting the saturated hydrocarbon group. The preferred carbon number of the saturated hydrocarbon group in which the methylene group may be substituted with an oxygen atom or -CO- is 2 to 10, more preferably 2 to 8, and further preferably 2 to 6. As the saturated hydrocarbon group in which the methylene group may be substituted by an oxygen atom, a linear or branched saturated hydrocarbon group (that is, a linear or branched alkyl group) is preferable. Saturated hydrocarbon groups (ie linear alkyl groups) are more preferred.

  When the methylene group is substituted with an oxygen atom or -CO-, the number of carbon atoms between the terminal and the oxygen atom or -CO- or between the oxygen atom or -CO- and the oxygen atom or -CO- is 1 ４4 are preferred, and 2-3 are more preferred.

The substituted or unsubstituted amino group which the alkyl group of R ^{9A to} R ^12A may have is an amino group; an N-methylamino group, an N-ethylamino group, an N-phenylamino group, an N, N
-Dimethylamino group, N, N-diethylamino group and the like. Examples of the halogen atom which the saturated hydrocarbon group of R ^{9A to} R ^12A may have include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

The aromatic hydrocarbon group represented by R ^{9A to} R ^12A preferably has 6 to 20 carbon atoms, more preferably has 6 to 15 carbon atoms, and still more preferably has 6 to 12 carbon atoms. Examples of the aromatic hydrocarbon group include a phenyl group, a toluyl group, a xylyl group, a naphthyl group, an anthryl group, a phenanthryl group, a biphenyl group and a terphenyl group. The aromatic hydrocarbon group may have one or more substituents. Examples of the substituent include a halogen atom such as a fluorine atom, a chlorine atom, an iodine atom and a bromine atom; a methoxy group and an ethoxy group. A C1-6 alkoxy group such as a group; a hydroxy group; a sulfamoyl group; a C1-6 alkylsulfonyl group such as a methylsulfonyl group; a C2-6 alkoxycarbonyl such as a methoxycarbonyl group and an ethoxycarbonyl group. Groups; and the like.
Further, the aralkyl group represented by R ^{9A to} R ^12A has 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, and still more preferably 7 to 17 carbon atoms. As the aralkyl group represented by R ^{9A to} R ^12A , an alkanediyl group having 1 to 5 carbon atoms such as a methylene group, an ethylene group or a propylene group may be used as the group described as the aromatic hydrocarbon group for R ^{9A to} R ^12A. And a bonded group.

Among them, R ^{1A to} R ^8A are preferably a hydrogen atom or a saturated hydrocarbon group having 1 to 20 carbon atoms (preferably an alkyl group), more preferably a hydrogen atom or a methyl group, and more preferably a hydrogen atom. Particularly preferred.
R ^{9A to} R ^12A each independently have 1 to 20 carbon atoms which may have a substituent.
Is preferably a saturated hydrocarbon group (preferably an alkyl group), or an aralkyl group having 7 to 30 carbon atoms which may have a substituent.

  Examples of the aromatic hydrocarbon group represented by A include an aromatic hydrocarbon group having 6 to 20 carbon atoms such as a phenyl group, a toluyl group, a xylyl group, a naphthyl group, an anthryl group, a phenanthryl group, a biphenyl group, and a terphenyl group. Is mentioned.

Examples of the substituent which the aromatic hydrocarbon group represented by A may have include, for example, a halogen atom such as a fluorine atom, a chlorine atom and an iodine atom; a substituted or unsubstituted amino group; a hydroxy group; ; -SO ₃ ^-; -SO ₃ J, and the like. Examples of the substituent which may be substituted on the amino group include an alkyl group having 1 to 20 carbon atoms which may be substituted with an amino group or a halogen atom; and a substituent which may be substituted with an alkoxy group having 1 to 10 carbon atoms. Aryl groups such as a good phenyl group; and the like.
Among them, A is preferably an aromatic hydrocarbon group which may have a substituent.

J includes an inorganic cation or an organic cation. Specific examples include the same cation as Z ⁺ in the compound (1a) and the cation of the following formula.

[G] ^g- represents a g-valent anion. g may be 0, usually 1 to 14, preferably 1 to 12, more preferably 1 to 10, further preferably 1 to 6, and particularly preferably 1 to 4. . [G] ^g- includes an anion represented by the formula (y1), the formula (y2) or the formula (y3).

[Wherein, R ^B1 represents a monovalent organic group.
R ^B2 and R ^B3 represents a halogen atom or a halogenated hydrocarbon group, R ^B2 and R ^B3 are -SO ₂ -N bond together ^- may form a ring containing - -SO _2. R ^B4 and R ^B5 are 2
Represents a valent organic group.
M1 represents an aluminum atom or a boron atom. ]

The halogenated hydrocarbon group represented by R ^B2 or R ^B3 is preferably a fluorinated hydrocarbon group, and more preferably a perfluoroalkyl group.
The divalent organic group represented by R ^B4 or R ^B5 is preferably a divalent aromatic hydrocarbon group.

  Examples of the anion represented by the formula (y1) include a methanesulfonic acid anion, a toluenesulfonic acid anion, a dodecylbenzenesulfonic acid anion, a trifluoromethanesulfonic acid anion, and a perfluorobutanesulfonic acid anion.

  Examples of the anion represented by the formula (y2) include an anion represented by the following formula.

  Examples of the anion represented by the formula (y3) include an anion represented by the following formula.

[G] ^g- further includes, for example, a halide ion, a resin having a sulfonate anion, and a trisperfluoroalkylsulfonylmethide anion.

  Examples of the compound represented by the formula (Ab1) include a compound represented by the following formula. In the following formula, J has the same meaning as described above.

  When a triarylmethane dye (Ab) is contained, its content is preferably 1 part by mass or more and 99 parts by mass or less based on 100 parts by mass of the dye (A1).

  The compound represented by the formula (Ab2) (hereinafter, sometimes referred to as compound (Ab2)) also includes a tautomer thereof.

[In the formula (Ab2), R ^{41 to} R ⁴⁴ each independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aromatic group having 6 to 20 carbon atoms which may have a substituent. Represents a hydrocarbon group or an aralkyl group having 7 to 30 carbon atoms which may have a substituent, and in the saturated hydrocarbon group having 1 to 20 carbon atoms, a hydrogen atom contained in the saturated hydrocarbon group is substituted. Alternatively, it may be substituted with an unsubstituted amino group or a halogen atom, and when the saturated hydrocarbon group has 2 to 20 carbon atoms, the methylene group contained in the saturated hydrocarbon group is an oxygen atom or -CO- May be substituted. R ⁴¹ and R ⁴² may combine to form a ring together with the nitrogen atom to which they bind, or R ⁴³ and R ⁴⁴ may combine to form a ring together with the nitrogen atom to which they bind.
R ^{47 to} R ⁵⁴ each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, or an alkyl group having 1 to 8 carbon atoms, and when the alkyl group has 2 to 8 carbon atoms, methylene group constituting the alkyl group may be substituted by an oxygen atom or a -CO-, linked with R ⁴⁸ and R ⁵² each other, -NH -, - S- or SO ₂ - have the form You may.
Ring T ¹ represents an aromatic heterocyclic ring having 3 to 10 carbon atoms which may have a substituent.
[Y] ^m- represents an arbitrary m-valent anion.
m represents an arbitrary natural number. ]
In Formula (Ab2), when m is 2 or more, the cations in Formula (Ab2) may have the same structure or different structures.

The aromatic heterocyclic ring of the ring T ¹ may be a single ring or a condensed ring. The aromatic heterocyclic ring represented by ring T ¹ has 3 to 10 carbon atoms, and preferably 3 to 8 carbon atoms. Further, the aromatic heterocycle is preferably a 5- to 10-membered ring, and more preferably a 5- to 9-membered ring. Examples of the monocyclic aromatic heterocycle include a 5-membered ring containing a nitrogen atom such as a pyrrole ring, an oxazole ring, a pyrazole ring, an imidazole ring, and a thiazole ring; a 5-membered ring containing no nitrogen atom such as a furan ring and a thiophene ring. And a 6-membered ring containing a nitrogen atom such as a pyridine ring, a pyrimidine ring, a pyridazine ring, and a pyrazine ring; and the like, and the aromatic heterocyclic ring of the condensed ring includes an indole ring, a benzimidazole ring, a benzothiazole ring, and a quinoline. Condensed rings containing nitrogen atoms such as rings; rings containing no nitrogen atoms such as benzofuran rings; and the like.
As the substituent which the aromatic heterocyclic ring of the ring T ¹ may have, a halogen atom, a cyano group,
A saturated hydrocarbon group having 1 to 20 carbon atoms (preferably an alkyl group having 1 to 20 carbon atoms) which may have a substituent, and an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent A hydrogen group or a substituted or unsubstituted amino group; and the like, preferably a saturated hydrocarbon group having 1 to 20 carbon atoms (preferably an alkyl group having 1 to 20 carbon atoms), a substituted or unsubstituted amino group, or An aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent is exemplified.
Among them, as the aromatic heterocyclic ring T ^1, an aromatic heterocyclic ring is preferred containing a nitrogen atom, an aromatic heterocyclic 5-membered ring containing a nitrogen atom is more preferable.

Further, the ring T ¹ is more preferably a ring represented by the formula (Ab2-x1).

［式（Ａｂ２−ｘ１）中、
環Ｔ²は、炭素数３〜１０の芳香族複素環を表す。
Ｒ⁴⁵及びＲ⁴⁶は、それぞれ独立して、水素原子、炭素数１〜２０の飽和炭化水素基、置換基を有していてもよい炭素数６〜２０の芳香族炭化水素基又は置換基を有していてもよい炭素数７〜３０のアラルキル基を表し、該炭素数１〜２０の飽和炭化水素基において、該飽和炭化水素基に含まれる水素原子は、置換若しくは非置換のアミノ基又はハロゲン原子に置換されていてもよく、該飽和炭化水素基の炭素数が２〜２０である場合、該飽和炭化水素基に含まれるメチレン基は酸素原子又は−ＣＯ−に置換されていてもよい。Ｒ⁴⁵とＲ⁴⁶とが結合してそれらが結合する窒素原子とともに環を形成してもよい。
Ｒ⁵⁵は、炭素数１〜２０の飽和炭化水素基、又は置換基を有していてもよい炭素数６〜
２０の芳香族炭化水素基を表す。
ｋ１は、０又は１を表す。
＊は、カルボカチオンとの結合手を表す。］

[In the formula (Ab2-x1),
Ring T ² represents an aromatic heterocyclic ring having 3 to 10 carbon atoms.
R ⁴⁵ and R ⁴⁶ each independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent or a substituent. Represents an aralkyl group having 7 to 30 carbon atoms which may have, and in the saturated hydrocarbon group having 1 to 20 carbon atoms, a hydrogen atom contained in the saturated hydrocarbon group is a substituted or unsubstituted amino group or It may be substituted by a halogen atom, and when the saturated hydrocarbon group has 2 to 20 carbon atoms, the methylene group contained in the saturated hydrocarbon group may be substituted by an oxygen atom or -CO- . R ⁴⁵ and R ⁴⁶ may combine to form a ring together with the nitrogen atom to which they are attached.
R ⁵⁵ is a saturated hydrocarbon group having 1 to 20 carbon atoms or 6 to 6 carbon atoms which may have a substituent.
And 20 aromatic hydrocarbon groups.
k1 represents 0 or 1.
* Represents a bond to a carbocation. ]

［式（Ａｂ２−ｙ１）中、
Ｒ⁵⁶は、水素原子、炭素数１〜２０の飽和炭化水素基、又は置換基を有していてもよい炭素数６〜２０の芳香族炭化水素基を表す。
Ｘ２は、酸素原子、−Ｎ（Ｒ⁵⁷）−又は硫黄原子を表す。
Ｒ⁵⁷は、水素原子又は炭素数１〜１０のアルキル基を表す。
Ｒ⁴⁵及びＲ⁴⁶は、上記と同義である。
＊は、カルボカチオンとの結合手を表す。］ Further, the ring T ¹ is particularly preferably a ring represented by the formula (Ab2-y1).

[In the formula (Ab2-y1),
R ⁵⁶ represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent.
X2 represents an oxygen atom, -N ( ^R57 )-or a sulfur atom.
R ⁵⁷ represents a hydrogen atom or an alkyl group having 1 to 10 carbon atoms.
R ⁴⁵ and R ⁴⁶ are as defined above.
* Represents a bond to a carbocation. ]

In the above formula, aromatic heterocyclic rings T ² are, include the same rings as exemplified aromatic heterocycle in ring T ^1.

Further, the ring T ¹ is also preferably a ring represented by the formula (Ab2-x2).

［式（Ａｂ２−ｘ２）中、
環Ｔ³は、窒素原子を有する炭素数３〜１０の芳香族複素環を表す。
Ｒ⁵⁸は、炭素数１〜２０の飽和炭化水素基、又は置換基を有していてもよい炭素数６〜２０の芳香族炭化水素基を表す。
Ｒ⁵⁹は、水素原子、置換基を有していてもよい炭素数１〜２０の飽和炭化水素基、置換基を有していてもよい炭素数６〜２０の芳香族炭化水素基又は置換基を有していてもよい炭素数７〜３０のアラルキル基を表す。
ｋ２は、０又は１を表す。
＊は、カルボカチオンとの結合手を表す。］

[In the formula (Ab2-x2),
Ring T ³ represents a C 3-10 aromatic heterocyclic ring having a nitrogen atom.
R ⁵⁸ represents a saturated hydrocarbon group having 1 to 20 carbon atoms or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent.
R ⁵⁹ is a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent or a substituent. Represents an aralkyl group having 7 to 30 carbon atoms which may have
k2 represents 0 or 1.
* Represents a bond to a carbocation. ]

Further preferably, the ring T ¹ is a ring represented by the formula (Ab2-y2).

［式（Ａｂ２−ｙ２）中、
Ｒ⁶⁰は、水素原子、炭素数１〜２０の飽和炭化水素基、又は置換基を有していてもよい炭素数６〜２０の芳香族炭化水素基を表す。
Ｒ⁵⁹は、上記と同義である。
＊は、カルボカチオンとの結合手を表す。］

[In the formula (Ab2-y2),
R ⁶⁰ represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aromatic hydrocarbon group having 6 to 20 carbon atoms which may have a substituent.
R ⁵⁹ has the same meaning as described above.
* Represents a bond to a carbocation. ]

The saturated hydrocarbon groups represented by R ^{41 to} R ⁴⁶ , R ⁵⁵ , R ⁵⁶ and R ^{58 to} R ⁶⁰ may be any of linear, branched and cyclic. Further, the carbon number of the saturated hydrocarbon group is preferably 1 to 10, more preferably 1 to 8, further preferably 1 to 6, and particularly preferably 1 to 4. The saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^{41 to} R ⁴⁶ , R ⁵⁵ , R ⁵⁶ and R ^{58 to} R ⁶⁰ is the same as the group exemplified as the saturated hydrocarbon group represented by R ¹ The group of is mentioned. The chain saturated hydrocarbon group (alkyl group) preferably has 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms, and still more preferably 1 to 4 carbon atoms. The number of carbon atoms in the cyclic saturated hydrocarbon group (alicyclic saturated hydrocarbon group) is preferably 3 to 10, more preferably 6 to 10.

When the saturated hydrocarbon group represented by R ^{41 to} R ⁴⁶ has 2 to 20 carbon atoms, the methylene group contained in the saturated hydrocarbon group may be substituted with an oxygen atom or —CO—. , Preferably an oxygen atom. Further, an oxygen atom may be inserted between methylene groups constituting the saturated hydrocarbon group. In this case, as the saturated hydrocarbon group, a linear or branched saturated hydrocarbon group (that is, a linear or branched alkyl group) is preferable, and a linear saturated hydrocarbon group (that is, a linear Alkyl group) is more preferred. The preferred carbon number of the saturated hydrocarbon group in which the methylene group may be substituted by an oxygen atom or -CO- is 2 to 10, more preferably 2 to 8. When the methylene group is substituted with an oxygen atom or -CO-, the number of carbon atoms between the terminal and the oxygen atom or -CO- or between the oxygen atom or -CO- and the oxygen atom or -CO- is 1 ４4 are preferred, and 2-3 are more preferred.
The saturated hydrocarbon groups represented by R ^{41 to} R ⁴⁶ , R ⁵⁵ , R ⁵⁶ and R ^{58 to} R ⁶⁰ may be substituted with a substituted or unsubstituted amino group or a halogen atom. Examples of the substituted amino group include an alkylamino group such as a dimethylamino group and a diethylamino group. Examples of the halogen atom include fluorine, chlorine, bromine, and iodine. When the halogen atom is a fluorine atom, the saturated hydrocarbon group substituted by a halogen atom (fluorine atom) represented by R ^{41 to} R ⁴⁶ , R ⁵⁵ , R ⁵⁶ and R ^{58 to} R ⁶⁰ is a trifluoromethyl group And a perfluoroalkyl group such as pentafluoroethyl group and heptafluoropropyl group.
Examples of the substituent which the alkyl group represented by R ⁵⁹ may have include a halogen atom and a cyano group.
Examples of the optionally substituted aromatic hydrocarbon group represented by R ^{41 to} R ⁴⁶ , R ⁵⁵ , R ⁵⁶ , and R ^{58 to} R ⁶⁰ include an optionally substituted aromatic group represented by R ^9A. The same groups as the group hydrocarbon groups can be mentioned. The aromatic hydrocarbon group preferably has 6 to 20 carbon atoms, more preferably 6 to 10 carbon atoms. As the aromatic hydrocarbon group, a phenyl group, a toluyl group, a xylyl group, and a naphthyl group are preferable. The aromatic hydrocarbon group may have one or more substituents.
Examples of the optionally substituted aralkyl group represented by R ^{41 to} R ⁴⁶ and R ⁵⁹ include the same groups as the optionally substituted aralkyl group represented by R ^9A .
Examples of the alkyl group having 1 to 10 carbon atoms represented by R ^57, groups such as 1 to 10 carbon atoms of straight-chain or branched-chain alkyl groups exemplified in R ^9A are exemplified.
Among the groups represented by R ^{41 to} R ⁴⁶ , R ⁵⁵ , R ⁵⁶ , and R ^{58 to} R ⁶⁰ , the substituent in the aromatic hydrocarbon group and the aralkyl group includes a fluorine atom, a chlorine atom, an iodine atom and the like. A C1-6 alkoxy group such as a halogen atom, a methoxy group or an ethoxy group; a hydroxy group; a C1-6 alkyl group such as a methyl group or an ethyl group; a sulfamoyl group; a carbon atom 1 such as a methylsulfonyl group And C6 alkylsulfonyl groups; and a C1-6 alkoxycarbonyl group such as a methoxycarbonyl group and an ethoxycarbonyl group.

Straight alkyl group having 1 to 8 carbon atoms represented by R ⁴⁷ to R ⁵⁴ may be linear, may be any of branched and cyclic, preferably a linear, exemplified for R ¹ Examples thereof include groups having 1 to 8 carbon atoms among chain branched and cyclic alkyl groups.

When the alkyl group represented by R ^{47 to} R ⁵⁴ has 2 to 8 carbon atoms, a methylene group constituting the alkyl group is substituted with an oxygen atom or —CO— (preferably, As a substituted group), a group in which a methylene group constituting an alkyl group having 2 to 20 carbon atoms represented by R ^{41 to} R ⁴⁶ is substituted with an oxygen atom or —CO— from a group having 8 carbon atoms. Groups selected from the following are listed. In the group, an oxygen atom may be inserted between methylene groups constituting the saturated hydrocarbon group.

Among them, as R ^{41 to} R ⁴⁴ , R ⁵⁵ , R ⁵⁶ , R ⁵⁸ and R ⁵⁹ , an aliphatic hydrocarbon group having 1 to 20 carbon atoms (preferably an alkyl group) and a carbon atom which may have a substituent An aromatic hydrocarbon group having the number of 6 to 20 is preferable.
Further, as R ^{47 to} R ⁵⁴ , each independently is preferably a hydrogen atom, a halogen atom or an alkyl group having 1 to 8 carbon atoms, and particularly preferably independently a hydrogen atom, a methyl group, a fluorine atom or a chlorine atom.
Furthermore, as the R ^56, it is preferably a saturated hydrocarbon group (preferably an alkyl group), or optionally substituted aromatic hydrocarbon group having 1 to 10 carbon atoms, more preferably, 1 carbon atoms 8 saturated hydrocarbon groups (preferably alkyl groups), or halogen atoms, haloalkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, hydroxy groups, alkyl groups having 1 to 4 carbon atoms, or methylsulfonyl An aromatic hydrocarbon group which may be substituted with a group.
As R ⁵⁷ , a hydrogen atom or an alkyl group having 1 to 8 carbon atoms is preferable.

  Examples of the cation in the formula (Ab2) include cations represented by the formula (Ab2-I), and cations 1 to 12 having a substituent shown in Table 1. In the table, * represents a bond.

  In Table 1, Ph1 to Ph9 mean a group represented by the following formula. In the formula, * represents a bond.

  Examples of the cation in the formula (Ab2) include cations represented by the formula (Ab2-II), and cations 13 to 16 having a substituent shown in Table 2. In the table, * represents a bond.

  In Table 2, Ph1, Ph10, and Ph11 mean groups represented by the following formula. In the formula, * represents a bond.

  As the cation of the formula (Ab2), cation 1 to cation 6, cation 11, or cation 12 are preferable, and cation 1, cation 2, or cation 12 is more preferable.

[Y] ^m- represents a m-valent anion. m may be 0, preferably 1 to 14, more preferably 1 to 12, still more preferably 1 to 10, and even more preferably 1 to 6. , 1 to 4. Examples of [Y] ^m- include the anions exemplified as [G] ^g- , and further include anions represented by the formulas (y4), (y5) and (y6).

［式中、Ｒ^B6は、２価の有機基を表す。Ｒ^B7は、３価の芳香族炭化水素基を表す。ｎは、自然数を表す。］

[Wherein, R ^B6 represents a divalent organic group. R ^B7 represents a trivalent aromatic hydrocarbon group. n represents a natural number. ]

Examples of the anion represented by the formula (y4) include a methane disulfonic acid anion, a propane disulfonic acid anion, a toluene disulfonic acid anion, a naphthalenedisulfonic acid anion, and an anion represented by the following formula.

  Examples of the anion represented by the formula (y6) include an anion represented by the following formula. In the formula, n represents a natural number.

式（Ａｂ２）におけるアニオンとして、上記例示したアニオンのうち、耐熱性の点から、含ホウ素アニオン、含アルミニウムアニオン、及び、含フッ素アニオンを選択することが好ましい。

As the anion in the formula (Ab2), among the anions exemplified above, it is preferable to select a boron-containing anion, an aluminum-containing anion, and a fluorine-containing anion from the viewpoint of heat resistance.

  Examples of the compound (Ab2) include a compound represented by the following formula.

  When the compound represented by the formula (Ab2) is contained, its content is preferably from 1 part by mass to 99 parts by mass based on 100 parts by mass of the dye (A1).

  Coumarin dye (Ac) is a dye containing a compound having a coumarin skeleton in the molecule. Examples of the coumarin dye (Ac) include C.I. I. Acid Yellow 227, 250; I. Disperse Yellow 82, 184; I. Solvent Orange 112; C.I. I. Solvent Yellow 160, 172; coumarin dyes described in Japanese Patent No. 1299948; and the like. Those that dissolve in an organic solvent are preferred.

  Among them, as the coumarin dye, for example, a compound represented by the formula (Ac1) (hereinafter sometimes referred to as “compound (Ac1)”) is preferable.

[In the formula (Ac1), X ^C represents an oxygen atom or a sulfur atom.
R ^1C independently represents a saturated hydrocarbon group having 1 to 20 carbon atoms. When the saturated hydrocarbon group has 2 to 20 carbon atoms, the methylene group constituting the saturated hydrocarbon group is replaced with an oxygen atom. It may be substituted.
R ^{2C to} R ^13C each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, a carbamoyl group, a sulfamoyl group, —SO ₃ M, —CO ₂ M, a hydroxy group, a formyl group, an amino group, Represents a monovalent hydrocarbon group of 1 to 20, and the methylene group constituting the hydrocarbon group may be replaced by an oxygen atom, a sulfur atom, -N ( ^R14C )-, a sulfonyl group or a carbonyl group; hydrogen atoms contained in the hydrocarbon group, a halogen atom, a cyano group, a nitro group, a carbamoyl group, a sulfamoyl _{group, -SO 3 M, -CO 2 M} , hydroxy groups, be substituted by a formyl group or an amino group Good.
R ^14C represents a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms, and when there are a plurality of R ^{14C s} , they may be the same or different.
M represents a hydrogen atom or an alkali metal atom.
L ^C represents a divalent hydrocarbon group or a sulfonyl group having 1 to 20 carbon atoms. ]

The saturated hydrocarbon group having 1 to 20 carbon atoms of R ^1C may be linear, branched, or cyclic, and is preferably a chain. Specific examples include the same groups as the groups exemplified as the saturated hydrocarbon group having 1 to 20 carbon atoms for R ¹ .
When the saturated hydrocarbon group represented by R ^1C has 2 to 20 carbon atoms, the methylene group contained in the saturated hydrocarbon group may be substituted with an oxygen atom. Further, an oxygen atom may be inserted between methylene groups constituting the saturated hydrocarbon group.
Examples of the monovalent hydrocarbon group having 1 to 20 carbon atoms R ^2C to R ^14C, monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, a monovalent unsaturated aliphatic hydrocarbon having 1 to 20 carbon atoms And monovalent aromatic hydrocarbon groups having 6 to 10 carbon atoms. Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms include the same groups as the groups exemplified as the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in R ¹ . Examples of the monovalent unsaturated hydrocarbon group having 1 to 20 carbon atoms include a vinyl group, a propenyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a nonenyl group, a decenyl group, an undecenyl group, Linear alkenyl groups such as dodecenyl group, hexadecenyl group, octadecenyl group and icosenyl group; cycloalkenyl groups such as cyclopentenyl group, cyclohexenyl group and cycloheptenyl group; and the like. Examples of the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms include the same groups as the groups exemplified as the aromatic hydrocarbon groups having 6 to 10 carbon atoms in R ¹ .
Examples of the divalent hydrocarbon group having 1 to 20 carbon atoms of L ^C include divalent saturated hydrocarbon groups having 1 to 20 carbon atoms, divalent unsaturated hydrocarbon groups having 1 to 20 carbon atoms, and 6 carbon atoms. And a divalent aromatic hydrocarbon group of 10 to 10, such as a group in which one hydrogen atom contained in a monovalent hydrocarbon group having 1 to 20 carbon atoms in R ^2C is a bond.
Further, a plurality of R ^{1C to} R ^13C are preferably the same groups.

Above all, as R ^1C , a chain alkyl group having 1 to 20 carbon atoms is preferable, and a chain alkyl group having 1 to 10 carbon atoms is more preferable.
As R ^{2C to} R ^6C , a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms is preferable, a hydrogen atom or a saturated hydrocarbon group having 1 to 10 carbon atoms is more preferable, and a hydrogen atom or a carbon atom is preferable. A chain alkyl group of the formulas 1 to 5 is more preferable.
As R ^{7C to} R ^13C , a hydrogen atom or a monovalent hydrocarbon group having 1 to 20 carbon atoms is preferable, and a hydrogen atom is particularly preferable.
As L ^C , a saturated hydrocarbon group having 1 to 20 carbon atoms such as a sulfonyl group, a methylene group, and a propanediyl group is preferable. Further, the divalent hydrocarbon group of L ^C preferably has 1 to 10 carbon atoms, and more preferably 1 to 5 carbon atoms.
X ^C is particularly preferably an oxygen atom.

  Examples of the compound (Ac1) include a compound represented by the following formula.

  When the coumarin dye (Ac) is contained, its content is preferably 1 part by mass or more and 99 parts by mass or less based on 100 parts by mass of the dye (A1).

Dyes other than dye (A1) include, for example, compounds classified as those having a hue other than pigment in the Color Index (published by The Society of Dyers and Colorists), and dyes described in Dyeing Note (Shikisensha). Dyes. Further, according to the chemical structure, azo dyes, cyanine dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinone imine dyes, methine dyes, azomethine dyes, squarylium dyes, acridine dyes, styryl dyes, quinoline dyes, nitro dyes and the like can be mentioned. . Among these, those soluble in organic solvents are preferred.

Specifically, C.I. I. Solvent Yellow 4, 14, 15, 23, 24, 25, 38, 62, 63, 68, 79, 81, 82, 83, 89, 94, 98, 99, 162;
C. I. Solvent orange 2, 7, 11, 15, 26, 41, 54, 56, 99;
C. I. Solvent Red 24, 49, 90, 91, 111, 118, 119, 122, 124, 125, 127, 130, 132, 143, 145, 146, 150, 151, 155, 160, 168, 169, 172, 175, 181, 207, 222, 227, 230, 245, 247;
C. I. Solvent violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;
C. I. Solvent Blue 14, 18, 35, 36, 45, 58, 59, 59: 1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;
C. I. Solvent Green 1, 3, 5, 28, 29, 32, 33; I. Solvent dye,
C. I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;
C. I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 149, 162, 169, 173;
C. I. Acid Red 73, 80, 91, 97, 138, 151, 211, 274;
C. I. Acid green 3, 5, 9, 25, 27, 28, 41;
C. I. Acid Violet 34, 120;
C. I. Acid Blue 25, 27, 40, 45, 78, 80, 112; I. Acid dyes,

  C. I. Basic Green 1; I. Basic dyes,

C. I. Reactive yellow 2, 76, 116;
C. I. C. Reactive Orange 16; I. Reactive dyes,

C. I. Direct Yellow 2, 4, 28, 33, 34, 35, 38, 39, 43, 44, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 132, 136, 138, 141;
C. I. Direct orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
C. I. Direct blue 40; I. Direct dye,

C. I. Disperse Yellow 51, 54, 76;
C. I. Disperse violet 26, 27;
C. I. C. Disperse Blue 1, 14, 56, 60; I. Disperse dye,

C. I. As a modant dye, C.I. I. Modant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;
C. I. Modant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48; . I. Modant dye,

  C. I. Bat green 1 etc. I. Vat dyes and the like.

  In the dye, the content of the dye (A1) is preferably 70% by mass or more and 100% by mass or less, more preferably 80% by mass or more and 100% by mass or less, and further preferably 85% by mass or less based on the total amount of the dye. It is not less than 100% by mass and not less than 100% by mass.

The coloring agent (A) further contains a pigment (A2). The pigment (A2) is not particularly limited, and known pigments can be used. For example, pigments classified into pigments by a color index (published by The Society of Dyers and Colorists) can be used. Or a combination of two or more.
Examples of the pigment include C.I. 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, Yellow pigments such as 139, 147, 148, 150, 153, 154, 166, 173, 194, 214;
C. I. Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;
C. I. Red pigments such as CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265;
C. I. Blue pigments such as CI Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60;
C. I. Violet color pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, 38;
C. I. Green pigments such as Pigment Green 7, 36, 58;
C. I. Brown pigments such as Pigment Brown 23 and 25;
C. I. And black pigments such as CI Pigment Black 1 and 7.

Among them, phthalocyanine pigments are preferred, more preferably copper phthalocyanine pigments and zinc phthalocyanine pigments, further preferably halogenated copper phthalocyanine pigments and halogenated zinc phthalocyanine pigments, and particularly preferably halogenated copper phthalocyanine pigments. is there.
As the pigment, a blue pigment and a green pigment are preferable, and a blue pigment is more preferable.
Specifically, C.I. I. And blue pigments such as CI Pigment Blue 15, 15: 3, 15: 4, 15: 6, and 60. I. Pigment Blue 15, 15: 3, 15: 4, 15: 6 and the like are preferred, and halogenated copper phthalocyanine blue pigments are preferred. I. Pigment Blue 15: 6 is particularly preferred. By including the pigment, the transmission spectrum can be easily optimized, and the light resistance and chemical resistance of the color filter can be improved.

If necessary, the pigment may be treated with rosin, surface treatment using a pigment derivative having an acidic or basic group introduced, graft treatment on the pigment surface with a polymer compound, etc., atomization by sulfuric acid atomization, etc. A treatment, a cleaning treatment with an organic solvent, water, or the like for removing impurities, a treatment for removing ionic impurities by an ion exchange method, or the like may be performed.
The pigment preferably has a uniform particle size. By performing a dispersion treatment by adding a pigment dispersant, a pigment dispersion in which the pigment is uniformly dispersed in the solution can be obtained.

The pigment dispersant includes, for example, a surfactant, and may be any of a cationic, anionic, nonionic, and amphoteric surfactant. Specific examples include polyester-based, polyamine-based, and acrylic-based surfactants. These pigment dispersants may be used alone or in combination of two or more. Examples of the pigment dispersant include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (registered trademark) (manufactured by Zeneca Corporation), EFKA (manufactured by BASF), Addispar (registered trademark) (manufactured by Ajinomoto Fine Techno Co., Ltd.), Disperbyk (registered trademark) (manufactured by Big Chemie) and the like.
When the pigment dispersant contains a pigment dispersant, its content is preferably from 1% by mass to 500% by mass, more preferably from 5% by mass to 300% by mass, based on the total amount of the pigment (A2). It is as follows. When the content of the pigment dispersant is within the above range, a pigment dispersion having a uniform dispersion state tends to be obtained.

The content ratio of the dye (A1) to the pigment (A2) (dye (A1): pigment (A2)) is 1:99 to 89:11, preferably 1:99 to 70:30 on a mass basis. And more preferably 1:99 to 50:50, and still more preferably 5:95 to 50:50.
Further, the content of the pigment is preferably 1% by mass or more, more preferably 1.5% by mass or more, and preferably 50% by mass or less, based on the total amount of the solid components. It is more preferably at most 30 mass%, more preferably at most 30 mass%. When the pigment content is within the above range, a color filter having good chromaticity can be obtained.

In the colorant (A), examples of the combination of the dye (A1) and the pigment (A2) include the following combinations.
As a combination when the colored curable resin composition of the present invention is prepared as a red colored curable resin composition, a coumarin dye (Ac) and a red pigment are exemplified.
A combination for preparing the colored curable resin composition of the present invention as a green colored curable resin composition includes a combination of a coumarin dye (Ac) and a green pigment; a coumarin dye (Ac) and a triarylmethane dye (Ab). And a green pigment; a combination of a coumarin dye (Ac) with a compound represented by the formula (Ab2) and a green pigment.
When the colored curable resin composition of the present invention is prepared as a blue colored curable resin composition, a combination of a xanthene dye (Aa), a triarylmethane dye (Ab) and a blue pigment; a xanthene dye (Aa) And a combination of a compound represented by the formula (Ab2) and a blue pigment; a combination of a xanthene dye (Aa) and a blue pigment; a combination of a xanthene dye (Aa) and a blue pigment and a violet pigment; a triarylmethane dye (Ab); A combination of a violet color pigment; a combination of a compound represented by the formula (Ab2) and a violet color pigment; In this case, the dye preferably contains at least one selected from the group consisting of a triarylmethane dye (Ab) and a compound represented by the formula (Ab2). The triarylmethane dye (Ab) and the formula (Ab2) More preferably, the composition further contains at least one selected from the group consisting of compounds represented by the formula (I) and a xanthene dye (Aa). The content of at least one selected from the group consisting of the triarylmethane dye (Ab) and the compound represented by the formula (Ab2) is preferably 40% by mass or more, more preferably 50% by mass, in the dye (A1). % Or more.

  The content of the coloring agent (A) is preferably 1% by mass or more and 60% by mass or less, more preferably 3% by mass or more and 55% by mass or less, more preferably 1% by mass or less, based on the total amount of solids. 5 mass% or more and 50 mass% or less. When the content of the colorant (A) is within the above range, the color density of the color filter is sufficient, and the resin and the polymerizable compound can be contained in a required amount in the composition. A colored pattern having a sufficient mechanical strength can be formed. Here, the “total amount of solid content” in the present specification refers to an amount obtained by removing the content of the solvent from the total amount of the colored curable resin composition. The total amount of the solid content and the content of each component with respect to the solid content can be measured by a known analytical means such as liquid chromatography or gas chromatography.

<Resin (B)>
The resin (B) is preferably an alkali-soluble resin, and is at least one type (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic anhydrides (hereinafter sometimes referred to as “(a)”). It is preferably a polymer having a structural unit derived from
The copolymer having a structural unit derived from (a) is a monomer (b) having a cyclic ether structure having 2 to 4 carbon atoms and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b)”). It is preferable that the copolymer be a copolymer having at least one selected from the group consisting of a structural unit derived from (a) and a structural unit having an ethylenically unsaturated bond. The copolymer may further have other structural units. As other structural units, structural units derived from the monomer (c) copolymerizable with (a) (however, different from (a) and (b), hereinafter sometimes referred to as “(c)”) Is mentioned. The structural unit having an ethylenically unsaturated bond is preferably a structural unit having a (meth) acryloyl group in a side chain. The resin having such a structural unit has a polymer having a structural unit derived from (a) or (b) and a group capable of reacting with a group contained in (a) or (b) and an ethylenically unsaturated bond. It is obtained by adding a monomer having the same.
Examples of such a structural unit include a structural unit obtained by adding (b) to a structural unit derived from (a), and a structural unit obtained by adding (a) to a structural unit derived from (b). When these structural units have a hydroxy group, structural units further added with a carboxylic acid anhydride are also exemplified as structural units having an ethylenically unsaturated bond.

Examples of (a) include unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, o-, m-, and p-vinylbenzoic acid;
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, dimethyl Unsaturated dicarboxylic acids such as tetrahydrophthalic acid and 1,4-cyclohexene dicarboxylic acid;
Methyl-5-norbornene-2,3-dicarboxylic acid, 5-carboxybicyclo [2.2.1] hept-2-ene, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene, Bicyclo unsaturated compounds containing a carboxy group such as 5-carboxymethylbicyclo [2.2.1] hept-2-ene and 5-carboxyethylbicyclo [2.2.1] hept-2-ene;
Carboxylic anhydrides such as anhydrides of the above-mentioned unsaturated dicarboxylic acids except fumaric acid and mesaconic acid;
Unsaturated mono [(meth) acryloyloxyalkyl] esters of di- or higher-valent polycarboxylic acids such as mono [2- (meth) acryloyloxyethyl] succinate and mono [2- (meth) acryloyloxyethyl] phthalate Kind;
Examples include unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α- (hydroxymethyl) acrylic acid.
Among these, acrylic acid, methacrylic acid, maleic anhydride and the like are preferred from the viewpoint of copolymerization reactivity and the solubility of the obtained resin in an aqueous alkali solution.

  (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) and an ethylenically unsaturated bond. (B) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloyloxy group.

  Examples of (b) include a monomer (b1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b1)”) and a monomer having an oxetanyl group and an ethylenically unsaturated bond. Monomer (b2) (hereinafter sometimes referred to as “(b2)”), monomer (b3) having a tetrahydrofuryl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b3)”) and the like. No.

  As (b1), for example, a monomer (b1-1) having a structure in which a linear or branched aliphatic unsaturated hydrocarbon is epoxidized (hereinafter referred to as “(b1-1)”) And a monomer (b1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as “(b1-2)”).

As (b1-1), a monomer having a glycidyl group and an ethylenically unsaturated bond is preferable. As (b1-1), specifically, glycidyl (meth) acrylate, β-methyl glycidyl (meth) acrylate, β-ethyl glycidyl (meth) acrylate, glycidyl vinyl ether, vinyl benzyl glycidyl ether, α-methyl vinyl benzyl Glycidyl ether, 2,3-bis (glycidyloxymethyl) styrene, 2,4-bis (glycidyloxymethyl) styrene, 2,5-bis (glycidyloxymethyl) styrene, 2,6-bis (glycidyloxymethyl) styrene 2,3,4-tris (glycidyloxymethyl) styrene, 2,3,5-tris (glycidyloxymethyl) styrene, 2,3,6-tris (glycidyloxymethyl) styrene, 3,4,5-tris (Glycidyloxymethyl) styrene, 2,4 6- tris (glycidyloxy) styrene, and the like.
As (b1-2), vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (for example, Celloxide (registered trademark) 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth) Acrylate (for example, Cyclomer (registered trademark) A400; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth) acrylate (for example, Cyclomer (registered trademark) M100; manufactured by Daicel Corporation), formula ( And a compound represented by formula (BII).

[In the formulas (BI) and (BII), R ^b1 and R ^b2 each independently represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group is a hydroxy group May be substituted.
X ^b1 and X ^b2 represents a single ^{bond, * - R b3 -, *} - R b3 -O -, * - R b3 -S- or * -R ^b3 represents a -NH-.
R ^b3 represents an alkanediyl group having 1 to 6 carbon atoms.
* Represents a bond with O. ]

Examples of the alkyl group having 1 to 4 carbon atoms for R ^b1 and R ^b2 include a methyl group and an ethyl group.
^Examples of the alkyl group in which the hydrogen atom of R ^b1 and R ^b2 is substituted with hydroxy include a hydroxymethyl group and a hydroxyethyl group.
As R ^b1 and R ^b2 , a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a hydroxyalkyl group having 1 to 4 carbon atoms is preferable, and a hydrogen atom or an alkyl group having 1 to 4 carbon atoms is more preferable. And more preferably a hydrogen atom and a methyl group.

^Examples of the alkanediyl group for R ^b3 include a linear or branched alkanediyl group, and specific examples include a methylene group and an ethylene group.
The X ^b1 and X ^b2, a single bond, * - R ^b3 -, or * -R ^b3 -O-, more preferably a single bond, or * -R ^b3 -O-, and further preferably a single bond , * - CH ₂ -O
- and * -CH ₂ CH ₂ -O- and the like, particularly preferably a single bond, * - CH ₂ CH ₂ -O- and the like (* represents a bond to O).

  Examples of the compound represented by the formula (BI) include compounds represented by any of the formulas (BI-1) to (BI-15). Among them, the formula (BI-1), the formula (BI-3), the formula (BI-5), the formula (BI-7), the formula (BI-9), or the formulas (BI-11) to (BI-15) The compound represented by Formula (BI-1), Formula (BI-7), Formula (BI-9) or Formula (BI-15) is more preferable.

  Examples of the compound represented by the formula (BII) include compounds represented by any of the formulas (BII-1) to (BII-15). Among them, Formula (BII-1), Formula (BII-3), Formula (BII-5), Formula (BII-7), Formula (BII-9) or Formula (BII-11) to Formula (BII-15) The compound represented by Formula (BII-1), Formula (BII-7), Formula (BII-9) or Formula (BII-15) is more preferable.

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

  As (b2), a monomer having an oxetanyl group and a (meth) acryloyloxy group is more preferable. (B2) includes 3-methyl-3- (meth) acryloyloxymethyloxetane, 3-ethyl-3- (meth) acryloyloxymethyloxetane, 3-methyl-3- (meth) acryloyloxyethyloxetane, Ethyl-3- (meth) acryloyloxyethyl oxetane and the like.

As (c), for example, 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, tricyclo [5.2.1.0 ^2,6 ] decane-8-
Yl (meth) acrylate (in the art, it is commonly used as "dicyclopentanyl (meth) acrylate" and sometimes as "tricyclodecyl (meth) acrylate"), tricyclo [5 2.2.1.0 ^2,6 ] decane-9-yl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decen-8-yl (meth) acrylate (common names in the art) Is referred to as "dicyclopentenyl (meth) acrylate"), tricyclo [5.2.1.0 ^2,6 ] decene-9-yl (meth) acrylate, dicyclopentanyloxyethyl (meth) acrylate , Isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, Sulfonyl (meth) acrylate, naphthyl (meth) acrylate, (meth) acrylic acid esters such as benzyl (meth) acrylate;
Hydroxy group-containing (meth) acrylates such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate;
Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate and diethyl itaconate;
Bicyclo [2.2.1] hept-2-ene, 5-methylbicyclo [2.2.1] hept-2-ene, 5-ethylbicyclo [2.2.1] hept-2-ene, 5- Hydroxybicyclo [2.2.1] hept-2-ene, 5-hydroxymethylbicyclo [2.2.1] hept-2-ene, 5- (2′-hydroxyethyl) bicyclo [2.2.1] Hept-2-ene, 5-methoxybicyclo [2.2.1] hept-2-ene, 5-ethoxybicyclo [
2.2.1] Hept-2-ene, 5,6-dihydroxybicyclo [2.2.1] hept-2-ene, 5,6-di (hydroxymethyl) bicyclo [2.2.1] hept- 2-ene, 5,6-di (2'-hydroxyethyl) bicyclo [2.2.1] hept-2-ene, 5,6-dimethoxybicyclo [2.2.1] hept-2-ene, 5 , 6-Diethoxybicyclo [2.2.1] hept-2-ene, 5-hydroxy-5-methylbicyclo [2.2.1] hept-2-ene, 5-hydroxy-5-ethylbicyclo [2 2.2.1] Hept-2-ene, 5-hydroxymethyl-5-methylbicyclo [2.2.1] hept-2-ene, 5-tert-butoxycarbonylbicyclo [2.2.1] hept-2 -Ene, 5-cyclohexyloxycarbonylbicycle B [2.2.1] hept-2-ene, 5-phenoxycarbonylbicyclo [2.2.1] hept-2-ene, 5,6-bis (tert-butoxycarbonyl) bicyclo [2.2.1] Bicyclo unsaturated compounds such as hept-2-ene and 5,6-bis (cyclohexyloxycarbonyl) bicyclo [2.2.1] hept-2-ene;
N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3 Dicarbonylimide derivatives such as -maleimidopropionate, N- (9-acridinyl) maleimide;
Vinyl group-containing aromatic compounds such as styrene, α-methylstyrene, vinyltoluene, and p-methoxystyrene; vinyl group-containing nitriles such as (meth) acrylonitrile; halogenated hydrocarbons such as vinyl chloride and vinylidene chloride; (meth) acrylamide Amides such as vinyl acetate; esters such as vinyl acetate; diene such as 1,3-butadiene, isoprene and 2,3-dimethyl-1,3-butadiene;
Among them, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo [2.2.1] hept-2-ene and the like are preferred from the viewpoint of copolymerization reactivity and heat resistance. preferable.

  The reaction order is not limited, and the monomer (a) and at least one of the monomers (b) and (c) may be copolymerized at one time. When any of the monomers (a) to (c) is used, the monomer (c) may be reacted after copolymerizing the monomer (a) and the monomer (b). Alternatively, the monomer (b) may be reacted after copolymerizing the monomer (a) and the monomer (c). Further, the copolymer of the monomers (b) and (c) may be reacted with the monomer (a), and further reacted with a carboxylic anhydride.

  The polymerization initiator, the solvent, and the like are not particularly limited, and those commonly used in the art can be used. For example, as the polymerization initiator, azo compounds (2,2′-azobisisobutyronitrile, 2,2′-azobis (2,4-dimethylvaleronitrile) and the like) and organic peroxides (benzoyl peroxide and the like) Any solvent may be used as long as it can dissolve each monomer, and examples of the solvent (E) for the colored curable resin composition of the present invention include the solvents described below.

The obtained copolymer may be used as a solution after the reaction, may be used as a concentrated or diluted solution, or may be taken out as a solid (powder) by a method such as reprecipitation. A thing may be used. In particular, by using the solvent contained in the colored curable resin composition of the present invention as a solvent during this polymerization, the solution after the reaction can be used as it is for the preparation of the colored curable resin composition of the present invention. Therefore, the production process of the colored curable resin composition of the present invention can be simplified.
Further, if necessary, a reaction catalyst (for example, tris (dimethylaminomethyl) phenol or the like) of a carboxylic acid or a carboxylic anhydride with a cyclic ether, a polymerization inhibitor (for example, hydroquinone) or the like may be used.
Examples of the carboxylic anhydride include maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1 , 2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride and the like. The amount of the carboxylic anhydride to be used is preferably 0.5 to 1 mol per 1 mol of the (a) used.

Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymer and 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] Copolymers having structural units derived from (a) and (b) such as decyl acrylate / (meth) acrylic acid copolymer; glycidyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer Polymer, glycidyl (meth) acrylate / styrene / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl acrylate / (meth) acrylic acid / N- (A) and (b) such as cyclohexylmaleimide copolymer and 3-methyl-3- (meth) acryloyloxymethyloxetane / (meth) acrylic acid / styrene copolymer And copolymers having structural units derived from (c); (a) and (c) such as benzyl (meth) acrylate / (meth) acrylic acid copolymer and styrene / (meth) acrylic acid copolymer; Copolymer having structural units derived from it; resin obtained by adding glycidyl (meth) acrylate to benzyl (meth) acrylate / (meth) acrylic acid copolymer; tricyclodecyl (meth) acrylate / styrene / (meth) acryl Resin obtained by adding glycidyl (meth) acrylate to acid copolymer, resin obtained by adding glycidyl (meth) acrylate to tricyclodecyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer, etc. A polymer having a structural unit obtained by adding (b) to a structural unit derived from (a); tricyclodecyl (meth) a Resin obtained by reacting (meth) acrylic acid with a copolymer of acrylate / glycidyl (meth) acrylate, and reacting (meth) acrylic acid with a copolymer of tricyclodecyl (meth) acrylate / styrene / glycidyl (meth) acrylate Having a structural unit obtained by adding (a) to a structural unit derived from (b), such as a cured resin; and a copolymer of tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate with (meth) acrylic (A) is added to a structural unit derived from (b), such as a resin obtained by reacting tetrahydrophthalic anhydride with a resin obtained by reacting an acid, and a structural unit obtained by further adding a carboxylic acid anhydride to (c) And a copolymer having a structural unit derived from the above.
Above all, as the resin (B), a copolymer having a structural unit derived from (a) and (b) and a copolymer having a structural unit derived from (a), (b) and (c) are preferable. .

The weight average molecular weight in terms of polystyrene of the resin (B) is preferably from 3,000 to 100,000, more preferably from 5,000 to 50,000, and still more preferably from 5,000 to 30,000. . When the molecular weight is within the above range, the hardness of the color filter is improved, the residual film ratio is high, the solubility of the unexposed portion in the developing solution is good, and the resolution of the colored pattern tends to be improved.
The molecular weight distribution [weight average molecular weight (Mw) / number average molecular weight (Mn)] of the resin (B) is preferably from 1.1 to 6, and more preferably from 1.2 to 4.

  The solid content acid value of the resin (B) is preferably from 50 to 170 mg-KOH / g, more preferably from 60 to 150 mg-KOH / g, and still more preferably from 70 to 135 mg-KOH / g. Here, the solid content acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be determined by, for example, titration using an aqueous solution of potassium hydroxide. Can be.

The content of the resin (B) is preferably from 7 to 65% by mass, more preferably from 13 to 60% by mass, and still more preferably from 17 to 55% by mass, based on the total amount of the solid content. When the content of the resin (B) is within the above range, a colored pattern can be formed, and the resolution and the residual film ratio of the colored pattern tend to be improved.

<Polymerizable compound (C)>
The polymerizable compound (C) is a compound that can be polymerized by an active radical and / or an acid generated from the polymerization initiator (D), and examples thereof include a compound having a polymerizable ethylenically unsaturated bond and the like. Is a (meth) acrylate compound.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such a polymerizable compound include nonylphenyl carbitol acrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-ethylhexyl carbitol acrylate, 2-hydroxyethyl acrylate, N-vinylpyrrolidone, and the above-mentioned (Ba) Compounds having one ethylenically unsaturated bond, such as the compounds exemplified as (Bb) and (Bc);
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 A compound having two ethylenically unsaturated bonds, such as 3-methylpentanediol di (meth) acrylate;
Compounds having three ethylenically unsaturated bonds such as trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, tris (2- (meth) acryloyloxyethyl) isocyanurate;
It has four ethylenically unsaturated bonds such as pentaerythritol tetra (meth) acrylate, ethylene glycol-modified pentaerythritol tetra (meth) acrylate, propylene glycol-modified pentaerythritol tetra (meth) acrylate, and caprolactone-modified pentaerythritol tetra (meth) acrylate. Compound;
Compounds having five ethylenically unsaturated bonds, such as dipentaerythritol penta (meth) acrylate;
Ethylenic unsaturated bonds such as dipentaerythritol hexa (meth) acrylate, ethylene glycol-modified dipentaerythritol hexa (meth) acrylate, propylene glycol-modified dipentaerythritol hexa (meth) acrylate, and caprolactone-modified dipentaerythritol hexa (meth) acrylate A compound having six;
Compounds having seven or more ethylenically unsaturated bonds, such as tripentaerythritol hepta (meth) acrylate, tripentaerythritol octa (meth) acrylate, tetrapentaerythritol nona (meth) acrylate, tetrapentaerythritol deca (meth) acrylate; etc. Is mentioned.
Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds, and more preferably a polymerizable compound having five to six ethylenically unsaturated bonds. . Specifically, dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate are preferred.
Typical polymerizable compounds (C) in the present invention include KAYARAD (registered trademark) DPHA (Nippon Kayaku Co., Ltd.), A-TMM-3LM-N (Shin-Nakamura Chemical Co., Ltd.) and A9550 (Shin-Nakamura) Chemical Industry Co., Ltd.).

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

The content of the polymerizable compound (C) is preferably from 7 to 65% by mass, more preferably from 13 to 60% by mass, and still more preferably from 17 to 55% by mass, based on the total amount of solids. is there. When the content of the polymerizable compound (C) is within the above range, the residual film ratio at the time of forming a colored pattern and the chemical resistance of the color filter tend to be improved.

  The content ratio of the resin (B) to the polymerizable compound (C) [resin (B): polymerizable compound (C)] is preferably 20:80 to 80:20 on a mass basis, and Preferably it is 35: 65-80: 20.

<Polymerization initiator (D)>
The polymerization initiator (D) is a compound that generates an active radical under the action of light or heat and can initiate polymerization. The colored curable resin composition of the present invention contains a compound represented by the following formula (d1) (hereinafter, may be referred to as “compound (d1)”) as a polymerization initiator.

[In the formula (d1),
R ^d1 represents an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, a heterocyclic group having 3 to 36 carbon atoms which may have a substituent, or a substituent. Represents an alkyl group having 1 to 15 carbon atoms which may be substituted or an aralkyl group having 7 to 33 carbon atoms which may have a substituent, and a methylene group (—CH ₂ —) included in the alkyl group or the aralkyl group Is -O-, -CO-,
—S—, —SO ₂ — or —N (R ^d5 ) — may be substituted.
R ^d2 represents an aromatic hydrocarbon group having 6 to 18 carbon atoms, a heterocyclic group having 3 to 36 carbon atoms, or an alkyl group having 1 to 10 carbon atoms.
R ^d3 represents an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, or a heterocyclic group having 3 to 36 carbon atoms which may have a substituent.
R ^d4 represents an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, or an aliphatic hydrocarbon group having 1 to 15 carbon atoms which may have a substituent; a methylene group contained in the aliphatic hydrocarbon group (-CH ₂ -) is, -O -, - CO- or -S- may be replaced, a methine group (-CH contained in the aliphatic hydrocarbon group <) May be replaced by —PO ₃ <, and a hydrogen atom contained in the aliphatic hydrocarbon group may be replaced by an OH group.
R ^d5 represents an alkyl group having 1 to 10 carbon atoms, and the methylene group (—CH ₂ —) contained in the alkyl group may be replaced by —O— or —CO—. ]

The aromatic hydrocarbon group represented by R ^d1 preferably has 6 to 15 carbon atoms, more preferably 6 to 12, and further preferably 6 to 10 carbon atoms. Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a biphenyl group, and a terphenyl group. A phenyl group and a naphthyl group are more preferable, and a phenyl group is particularly preferable.
The aromatic hydrocarbon group represented by R ^d1 may have one or more substituents. The substituent is preferably substituted at the α-position or γ-position of the aromatic hydrocarbon group, more preferably at the γ-position. Examples of the substituent include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, butadecyl, and pentadecyl. 1 to 15 carbon atoms such as
An alkyl group; a halogen atom such as a fluorine atom, a chlorine atom, an iodine atom, and a bromine atom;
The alkyl group as the substituent preferably has 1 to 10 carbon atoms, and more preferably 1 to 7 carbon atoms. The alkyl group as the substituent may be linear, branched, or cyclic, and may be a combination of a chain and a cyclic group. The methylene group contained in the alkyl group as a substituent (-CH ₂ -) is, -O-, or may be replaced by -S-. Further, the hydrogen atom contained in the alkyl group may be substituted with a halogen atom such as a fluorine atom, a chlorine atom, an iodine atom and a bromine atom, and is preferably substituted with a fluorine atom.

Examples of the alkyl group as a substituent of the aromatic hydrocarbon group represented by R ^d1 include a group represented by the following formula. In the formula, * represents a bond.

Examples of the aromatic hydrocarbon group which may have a substituent represented by R ^d1 include a group represented by the following formula. In the formula, * represents a bond.

As the aromatic hydrocarbon group which may have a substituent represented by R ^d1 , a group represented by the following formula is preferable.

[In the formula, R ^d6 represents an alkyl group having 1 to 10 carbon atoms, and a hydrogen atom contained in the alkyl group may be substituted with a halogen atom. m2 represents an integer of 1 to 5. ]

Examples of the alkyl group represented by R ^d6 include the same groups as the alkyl groups exemplified as the substituent for the aromatic hydrocarbon group represented by R ^d1 . The carbon number of the alkyl group represented by R ^d6 is preferably 2 or more and 7 or less, more preferably 2 or more and 5 or less. The alkyl group represented by R ^d6 may be linear, branched, or cyclic, and is preferably a chain.
Examples of the halogen atom which may substitute a hydrogen atom contained in R ^d6 include a fluorine atom, a chlorine atom, an iodine atom and a bromine atom, and fluorine is particularly preferable. Further, it is preferable that 2 to 10 hydrogen atoms contained in R ^d6 are substituted with halogen atoms, and it is preferable that 3 to 6 hydrogen atoms are substituted with halogen atoms. The substitution position of the R ^d6 O- group is preferably an ortho position or a para position, and particularly preferably a para position.
M2 is preferably 1 to 2, and particularly preferably 1.

The number of carbon atoms of the heterocyclic group represented by R ^d1 is preferably 3 to 20, more preferably 3 to 10, and even more preferably 3 to 5. Examples of the heterocyclic group include a pyrrolyl group, a furyl group, a thienyl group, an indolyl group, a benzofuryl group, and a carbazolyl group.
Further, the heterocyclic group represented by R ^d1 may have one or more substituents. Examples of the substituent include the same groups as the groups exemplified as the substituent that the aromatic hydrocarbon group represented by R ^d1 may have.

The alkyl group represented by R ^d1 preferably has 1 to 12 carbon atoms. ^Examples of the alkyl group represented by R ^d1 include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, a tridecyl group, Butadecyl group, pentadecyl group and the like. These alkyl groups may be linear, branched, or cyclic, and may be a combination of a chain and a cyclic group. In the alkyl group represented by R ^d1 , a methylene group (—CH ₂ —
) ^May be replaced by —O—, —CO—, —S—, —SO ₂ — or —N (R ^d5 ) —, and the hydrogen atom may be replaced by an OH group or an SH group. Good.

R ^d5 represents an alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 1 to 5 carbon atoms, and more preferably an alkyl group having 1 to 3 carbon atoms. The alkyl group may be linear (linear or branched), cyclic, linear, branched, or cyclic. And a group combining a cyclic group. In the alkyl group represented by R ^d5 , a methylene group (—CH ₂ —) is —O— or —CO—
May be replaced by

Specific examples of the alkyl group which may have a substituent represented by R ^d1 include a group represented by the following formula. * Represents a bond.

Further, aralkyl group which may have a substituent represented by R ^d1 is a bivalent group derived from an alkyl group represented by an aromatic hydrocarbon group and the R ^d1 represented by R ^d1 Is preferably a group obtained by combining The aralkyl group preferably has 7 to 33 carbon atoms, more preferably 7 to 18 carbon atoms, and still more preferably 7 to 12 carbon atoms. The aralkyl group may have one or more substituents, examples of the substituent, the aromatic hydrocarbon group represented by R ^d1, and the alkyl group represented by R ^d1 Yes The same groups as the groups exemplified as the substituent which may be used are exemplified. The group formed by combining a divalent group derived from an alkyl group represented by an aromatic hydrocarbon group and the R ^d1 represented by the R ^d1, specifically, a group represented by the following formula Can be mentioned. In the formula, * represents a bond.

R ^d1 is preferably an aromatic hydrocarbon group which may have a substituent, or an alkyl group which may have a substituent, and an aromatic hydrocarbon group which may have a substituent Is more preferable, and a phenyl group which may have a substituent is further more preferable. Examples of the substituent in the aromatic hydrocarbon group and the phenyl group include an alkoxy group having 4 to 9 carbon atoms, an alkoxy group having 4 to 9 carbon atoms having a halogen (preferably a fluorine atom), and 1 to 3 methylene groups. An alkoxy group having 5 to 9 carbon atoms in which the group is substituted by an ether bond is preferred. Each of these substituents preferably has a branched structure.

The aromatic hydrocarbon group represented by R ^d2 preferably has 6 to 15 carbon atoms, more preferably 6 to 12 carbon atoms, and still more preferably 6 to 10 carbon atoms. Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a biphenyl group, a terphenyl group and the like.
The carbon number of the heterocyclic group represented by R ^d2 is preferably 3 to 20, more preferably 3 to 10, and still more preferably 3 to 5. Examples of the heterocyclic group include a pyrrolyl group, a furyl group, a thienyl group, an indolyl group, a benzofuryl group, and a carbazolyl group.
The alkyl group represented by R ^d2 preferably has 1 to 7 carbon atoms, more preferably 1 to 5 carbon atoms, and particularly preferably 1 to 3 carbon atoms. Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group. The alkyl group may be linear, branched, or cyclic, and may be a combination of a chain and a cyclic group.

R ^d2 is preferably a chain alkyl group, more preferably a chain alkyl group having 1 to 5 carbon atoms, still more preferably a chain alkyl group having 1 to 3 carbon atoms, and a methyl group. Particularly preferred.

The carbon number of the aromatic hydrocarbon group represented by R ^d3 is preferably 6 to 15, more preferably 6 to 12, and still more preferably 6 to 10. Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a biphenyl group and a terphenyl group, and a phenyl group and a naphthyl group are more preferred.
Further, the aromatic hydrocarbon group represented by R ^d3 may have one or more substituents. The substituent is preferably substituted at the α-position or γ-position of the aromatic hydrocarbon group. As the substituent, an aliphatic hydrocarbon group having 1 to 15 carbon atoms is preferable, and specifically, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group An alkyl group having 1 to 15 carbon atoms such as a group or a decyl group; an alkenyl group having 1 to 15 carbon atoms such as an ethenyl group, a propenyl group, a butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, a nonenyl group, a decenyl group; Is mentioned.
The aliphatic hydrocarbon group as the substituent preferably has 1 to 7 carbon atoms. Further, the aliphatic hydrocarbon group as the substituent may be any of linear, branched, and cyclic, and may be a combination of a chain and a cyclic group. Further, the aliphatic hydrocarbon group for the substituent, a methylene group (-CH ₂ -) is, -O -, - CO -, - S-
And the methine group (-CH <) may be replaced by -N <.

Examples of the aliphatic hydrocarbon group as a substituent of the aromatic hydrocarbon group represented by R ^d3 include a group represented by the following formula. In the formula, * represents a bond.

Examples of the aromatic hydrocarbon group which may have a substituent represented by R ^d3 include a group represented by the following formula. In the formula, * represents a bond.

The carbon number of the heterocyclic group represented by R ^d3 is preferably from 3 to 20, more preferably from 3 to 10, and even more preferably from 3 to 5. Examples of the heterocyclic group include a pyrrolyl group, a furyl group, a thienyl group, an indolyl group, a benzofuryl group, and a carbazolyl group.
Further, the heterocyclic group represented by R ^d3 may have one or more substituents, and the substituent is an aromatic hydrocarbon group represented by R ^d1. The same groups as the groups exemplified as the preferable substituents are exemplified.

R ^d3 is preferably an aromatic hydrocarbon group having a substituent, and more preferably a phenyl group having a substituent.
As the substituent, a chain alkyl group having 1 to 7 carbon atoms (more preferably 1 to 3 carbon atoms) is preferable, and the number of substituents is preferably 2 or more and 5 or less.

The number of carbon atoms of the aromatic hydrocarbon group represented by R ^d4 is preferably 6 to 15, more preferably 6 to 12, and still more preferably 6 to 10. Examples of the aromatic hydrocarbon group include a phenyl group, a naphthyl group, an anthryl group, a phenanthryl group, a biphenyl group, and a terphenyl group. A phenyl group and a naphthyl group are more preferable, and a phenyl group is particularly preferable.
The aromatic hydrocarbon group represented by R ^d4 may have one or more substituents. Examples of the substituent include the same groups as the substituents that the aromatic hydrocarbon group represented by R ^d1 may have.

The aliphatic hydrocarbon group represented by R ^d4 preferably has 1 to 13 carbon atoms, more preferably 2 to 10 carbon atoms, and still more preferably 4 to 9 carbon atoms. Examples of the aliphatic hydrocarbon group represented by R ^d4 include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, an undecyl group, a dodecyl group, Alkyl groups such as tridecyl, butadecyl, and pentadecyl groups; ethenyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl, dodecenyl, tridecenyl, butadecenyl Group, alkenyl group such as pentadecenyl group; and the like. These aliphatic hydrocarbon groups may be chain-like (straight-chain or branched-chain) or cyclic, or may be a combination of a chain-like group and a cyclic group. In the aliphatic hydrocarbon group represented by R ^d4 , a methylene group (—CH ₂
-) is -O -, - CO -, - may be replaced in S-, methine group (-CH <) may be replaced by -PO ₃ <. The hydrogen atom contained in the aliphatic hydrocarbon group is O
It may be substituted with an H group.

Examples of the aliphatic hydrocarbon group ^optionally having a substituent represented by R ^d4 include a group represented by the following formula. In the formula, * represents a bond.

R ^d4 is preferably a chain aliphatic hydrocarbon group which may have a substituent, more preferably a chain alkyl group, further preferably a branched chain alkyl group having 4 to 9 carbon atoms. Group.

  Examples of the compound (d1) include compounds (d1-1) to (d1-67) having a substituent shown in Tables 3 to 9. In the table, * represents a bond.

  Among them, compounds (d1-3) to (d1-6), (d1-18) to (d1-52), (d1-55), (d1-56), (d1-60), and (d1-61) And more preferably compounds (d1-3) to (d1-6) and (d1-18) to (d1-41), and further preferably compounds (d1-24) and (d1-36) to (d1-36). d1-40), and particularly preferably compound (d1-40).

  The content of the compound (d1) is preferably 30 parts by mass or more and 100 parts by mass or less, more preferably 50 parts by mass or more, and still more preferably 80 parts by mass or more in 100 parts by mass of the polymerization initiator (D). And still more preferably 90 parts by mass or more.

  Compound (d1) can be produced by the production method described in JP-T-2014-500852.

Further, the polymerization initiator (D) may further contain a polymerization initiator other than the compound (d1). These are not particularly limited, and known polymerization initiators can be used.
Examples of the polymerization initiator that generates an active radical include O-acyl oxime compounds, biimidazole compounds, alkylphenone compounds, triazine compounds, and acylphosphine oxide compounds other than the compound (d1).

The O-acyl oxime compound is N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-. On-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropan-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-di) Oxacyclopentanylmethyloxy) benzoyl {-9H-carbazol-3-yl] ethane-1-imine, N-acetoxy-1- [9-ethyl- -(2-Methylbenzoyl) -9H-carbazol-3-yl] -3-cyclopentylpropane-1-imine, N-benzoyloxy-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazole -3-yl] -3-cyclopentylpropan-1-one-2-imine and the like. Commercial products such as Irgacure (registered trademark) OXE01, OXE02 (all manufactured by BASF) and N-1919 (made by ADEKA) may be used. Among them, O-acyl oxime compounds include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1. -On-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropan-1-one-2-imine and N-acetyloxy-1- [4- {4- (2 -Hydroxyethoxy) phenyl {sulfanylphenyl] -propan-1-one-2-imine is preferred, and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one is preferred. -2-imine and N-acetyloxy-1- [4- {4- (2-hydroxyethoxy) ) Phenyl} sulfanyl phenyl] - at least one member selected from the group consisting of propan-1-one-2-imine is more preferable. With these O-acyl oxime compounds, a color filter with high brightness tends to be obtained.

As the biimidazole compound, specifically, 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenylbiimidazole, 2,2′-bis (2,3-dichlorophenyl) ) -4,4 ', 5,5'-Tetraphenylbiimidazole (for example, see JP-A-6-75372 and JP-A-6-75373), 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (alkoxyphenyl) biimidazole, 2,2 ' -Bis (2-chlorophenyl) -4,4 ', 5,5'-tetra (dialkoxyphenyl) biimidazole, 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetra (Trialkoxyphenyl) biimida (For example, see JP-B-48-38403, JP-A-62-174204, etc.), and imidazole in which the phenyl group at the 4,4 ', 5,5'-position is substituted by a carboalkoxy group. Compounds (for example, see JP-A-7-10913).
Among them, the compound represented by the formula (d4) is preferable.

[In the formula (d4), R ^{d13 to} R ^d16 each independently represent a hydrogen atom or an alkoxy group (preferably an alkoxy group having 1 to 4 carbon atoms, more preferably a methoxy group). R ^d17 and R ^d18 each independently represent a hydrogen atom or a halogen atom (preferably a chlorine atom). ]

  The alkylphenone compound is a compound having a partial structure represented by the formula (d5) or a partial structure represented by the formula (d6). In these partial structures, the benzene ring may have a substituent.

Examples of the compound having a partial structure represented by the formula (d5) include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one and 2-dimethylamino-1- (4 -Morpholinophenyl) -2-benzylbutan-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] butan-1-one And the like. Commercial products such as Irgacure 369, 907, and 379 (all manufactured by BASF) may be used.
Examples of the compound having a partial structure represented by the formula (d6) include 2-hydroxy-2-methyl-1-phenylpropan-1-one and 2-hydroxy-2-methyl-1- [4- (2 -Hydroxyethoxy) phenyl] propan-1-one, 1-hydroxycyclohexylphenyl ketone, oligomers of 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) propan-1-one, α, α-diethoxy Examples include acetophenone and benzyldimethyl ketal.
From the viewpoint of sensitivity, a compound having a partial structure represented by the formula (d5) is preferable as the alkylphenone compound.

  Examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine and 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-methoxy (Styryl) -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-methylpheni ) Ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine.

  Examples of the acylphosphine oxide compound include 2,4,6-trimethylbenzoyldiphenylphosphine oxide. A commercially available product such as Irgacure (registered trademark) 819 (manufactured by BASF) may be used.

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, methyl o-benzoylbenzoate, 4-phenylbenzophenone, and 4-benzoyl- Benzophenone compounds such as 4'-methyldiphenylsulfide, 3,3 ', 4,4'-tetra (tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone; 9,10-phenanthrenequinone; Quinone compounds such as 2-ethylanthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, titanocene compounds and the like. These are preferably used in combination with the later-described polymerization initiator (D1) (particularly amines).

  Among them, when two or more polymerization initiators are used, a combination of the compound (d1) and the biimidazole compound, a combination of the compound (d1) and the biimidazole compound and a thiol compound described below, or a combination of the compound (d1) and the alkylphenone compound Combinations and the like are preferred.

  The content of the polymerization initiator (D) is preferably at least 0.1 part by mass, more preferably 3 parts by mass, based on 100 parts by mass of the resin (B) and the polymerizable compound (C) in total. Or more, more preferably 5 or more parts by mass, and preferably 40 or less by mass, more preferably 30 or less by mass, still more preferably 27 or less by mass, even more preferably 25 or less by mass, and even more. Preferably it is 20 parts by mass or less. When the content of the polymerization initiator (D) is within the above range, the sensitivity is increased and the exposure time tends to be shortened, so that the productivity of the color filter is improved.

  Further, the content ratio of the polymerization initiator (D) and the polymerizable compound (C) (polymerization initiator (D) / polymerizable compound (C)) is preferably 1/1000 or more on a mass basis. , More preferably 4/1000 or more, preferably 40/100 or less, and more preferably 35/100 or less. When the content ratio (polymerization initiator (D) / polymerizable compound (C)) is within the above range, a color filter having excellent lightness (luminance) can be obtained.

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

  Examples of the amine compound include alkanolamines such as triethanolamine, methyldiethanolamine and triisopropanolamine; methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, and 2-dimethylbenzoate. Aminobenzoic acid esters such as aminoethyl and 2-dimethylhexyl 4-dimethylaminobenzoate; N, N-dimethylparatoluidine; 4,4′-bis (dimethylamino) benzophenone (commonly known as Michler's ketone), 4,4′-bis ( Alkylaminobenzophenones such as diethylamino) benzophenone and 4,4′-bis (ethylmethylamino) benzophenone; and the like, with alkylaminobenzophenone being preferred, and 4,4′-bis (diethylamino) benzyl Zofenon is preferable. A commercially available product such as EAB-F (manufactured by Hodogaya Chemical Industry Co., Ltd.) may be used.

  Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, and 9,10-diene. Butoxyanthracene, 2-ethyl-9,10-dibutoxyanthracene and the like.

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

Examples of the carboxylic acid compound include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid,
Examples include dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanylacetic acid, dichlorophenylsulfanylacetic acid, N-phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, and naphthoxyacetic acid.

As the polymerization initiation assistant (D1), a thioxanthone compound is preferable.
When using these polymerization initiation assistants (D1), the content thereof is preferably 0.1 to 30 parts by mass, based on 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). Preferably it is 1 to 20 parts by mass. When the polymerization initiator (D1) is used, its content is preferably from 5 to 80 parts by mass, more preferably from 10 to 60 parts by mass, based on 100 parts by mass of the total amount of the polymerization initiator (D). And more preferably 15 to 55 parts by mass. When the amount of the polymerization initiation assistant (D1) is within this range, a colored pattern can be formed with higher sensitivity, and the productivity of the color filter tends to be improved.

<Thiol compound (T)>
The colored curable resin composition of the present invention preferably further contains a thiol compound (T).
The thiol compound (T) is a compound having a sulfanyl group (-SH) in the molecule.
Examples of the compound having one sulfanyl group in the molecule include, for example, 2-sulfanyloxazole, 2-sulfanylthiazole, 2-sulfanylbenzimidazole, 2-sulfanylbenzothiazole, 2-sulfanylbenzoxazole, 2-sulfanylnicotinic acid, -Sulfanylpyridine, 2-sulfanylpyridin-3-ol, 2-sulfanylpyridine-N-oxide, 4-amino-6-hydroxy-2-sulfanylpyrimidine, 4-amino-6-hydroxy-2-sulfanylpyrimidine, 4- Amino-2-sulfanylpyrimidine, 6-amino-5-nitroso-2-thiouracil, 4,5-diamino-6-hydroxy-2-sulfanylpyrimidine, 4,6-diamino-2-sulfanylpyrimidine, 2,4 Diamino-6-sulfanylpyrimidine, 4,6-dihydroxy-2-sulfanylpyrimidine, 4,6-dimethyl-2-sulfanylpyrimidine, 4-hydroxy-2-sulfanyl-6-methylpyrimidine, 4-hydroxy-2-sulfanyl- 6-propylpyrimidine, 2-sulfanyl-4-methylpyrimidine, 2-sulfanylpyrimidine, 2-thiouracil, 3,4,5,6-tetrahydropyrimidine-2-thiol, 4,5-diphenylimidazole-2-thiol, -Sulfanilimidazole, 2-sulfanyl-1-methylimidazole, 4-amino-3-hydrazino-5-sulfanyl-1,2,4-triazole, 3-amino-5-sulfanyl-1,2,4-triazole, 2 -Methyl-4H-1,2,4- Riazol-3-thiol, 4-methyl-4H-1,2,4-triazole-3-thiol, 3-sulfanyl 1H-1,2,4-triazol-3-thiol, 2-amino-5-sulfanyl-1 , 3,4-thiadiazole, 5-amino-1,3,4-thiadiazole-2-thiol, 2,5-disulfanyl-1,3,4-thiadiazole, (furan-2-yl) methanethiol, 2- Sulfanyl-5-thiazolidone, 2-sulfanylthiazoline, 2-sulfanyl-4 (3H) -quinazolinone, 1-phenyl-1H-tetrazol-5-thiol, 2-quinolinethiol, 2-sulfanyl-5-methylbenzimidazole, 2 -Sulfanyl-5-nitrobenzimidazole, 6-amino-2-sulfanylbenzothiazole, 5 Chloro-2-sulfanylbenzothiazole, 6-ethoxy-2-sulfanylbenzothiazole, 6-nitro-2-sulfanylbenzothiazole, 2-sulfanylnaphthoimidazole, 2-sulfanylnaphthoxazole, 3-sulfanyl-1,2,4- Triazole, 4-amino-6-sulfanylpyrazolo [2,4-d] pyridine, 2-amino-6-purinthiol, 6-sulfanylpurine, 4-sulfanyl-1H-pyrazolo [2,4-d] pyrimidine and the like Is mentioned.

  Compounds having two or more sulfanyl groups in the molecule include hexanedithiol, decanedithiol, 1,4-bis (methylsulfanyl) benzene, butanediol bis (3-sulfanylpropionate), butanediol bis (3-sulfanyl) Acetate), ethylene glycol bis (3-sulfanyl acetate), trimethylolpropane tris (3-sulfanyl acetate), butanediol bis (3-sulfanyl propionate), trimethylolpropane tris (3-sulfanyl propionate), trimethylolpropane Methylolpropane tris (3-sulfanyl acetate), pentaerythritol tetrakis (3-sulfanyl propionate), pentaerythritol tetrakis (3-sulfanyl acetate), Tris Mud carboxyethyl tris (3-sulfanyl propionate), pentaerythritol tetrakis (3-sulfanyl butyrate), 1,4-bis (3-sulfanyl-butyloxy) include butane and the like.

As the thiol compound (T), a compound having one sulfanyl group in the molecule is preferable, and 2-sulfanylbenzthiazole is particularly preferable.
The content of the thiol compound (T) is preferably 0.5 to 20 parts by mass, more preferably 1 to 15 parts by mass, based on 100 parts by mass of the polymerization initiator (D). When the content of the thiol compound (T) is within this range, the sensitivity tends to be high and the developability tends to be good.

<Solvent (E)>
The colored curable resin composition of the present invention preferably further contains a solvent (E).
The solvent (E) is not particularly limited, and a solvent usually used in the art can be used. For example, an ester solvent (a solvent containing -COO- in the molecule but not containing -O-), an ether solvent (a solvent containing -O- in the molecule but not containing -COO-), and an ether ester solvent (a solvent containing -COO- in the molecule) , A solvent containing -COO- and -O-), a ketone solvent (a solvent containing -CO- in the molecule and not containing -COO-), an alcohol solvent (containing OH in the molecule, -O-,- Solvents that do not contain CO— and —COO—), aromatic hydrocarbon solvents, amide solvents, dimethyl sulfoxide, and the like.

  As ester solvents, 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.

  Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, and 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, diethyl Glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, and the like phenetol and methyl anisole.

Examples of ether ester solvents include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, and 3-ethoxy. Ethyl propionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, Ethyl 2-ethoxy-2-methylpropionate, 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, and the like diethylene glycol monobutyl ether acetate and dipropylene glycol methyl ether acetate.

  Examples of the ketone solvent include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, diacetone alcohol, and cyclopentanone. , Cyclohexanone and isophorone.

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

  Examples of the aromatic hydrocarbon solvent include benzene, toluene, xylene and mesitylene.

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

  Among the above-mentioned solvents, an organic solvent having a boiling point of 120 ° C. or more and 180 ° C. or less at 1 atm is preferable from the viewpoint of coating properties and drying properties. As the solvent, propylene glycol monomethyl ether acetate, ethyl lactate, propylene glycol monomethyl ether, ethyl 3-ethoxypropionate, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diacetone alcohol, 4-hydroxy-4-methyl -2-pentanone and N, N-dimethylformamide are preferred, and propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate, diacetone alcohol and ethyl 3-ethoxypropionate are more preferred.

  The content of the solvent (E) is preferably from 35 to 95% by mass, more preferably from 40 to 92% by mass, based on the total amount of the colored curable resin composition of the present invention. In other words, the total amount of the solid content of the colored curable resin composition is preferably 5 to 65% by mass, more preferably 8 to 60% by mass. When the content of the solvent (E) is within the above range, the flatness at the time of coating becomes good, and the display characteristics tend to be good because the color density is not insufficient when a color filter is formed. .

<Leveling agent (F)>
The colored curable resin composition of the present invention may contain a leveling agent (F).
Examples of the leveling agent (F) include a silicone-based surfactant and a fluorine-based surfactant. These may have a polymerizable group in the side chain.
Examples of the silicone-based surfactant include a surfactant having a siloxane bond in a molecule. Specifically, Toray silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: manufactured by Dow Corning Toray), KP321, KP322, KP323, KP
324, KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452 and TSF4460 (manufactured by Momentive Performance Materials Japan GK), etc. Is mentioned.

  Examples of the fluorine-based surfactant include a surfactant having a fluorocarbon chain in a molecule. Specifically, Florado (registered trademark) FC430 and FC431 (manufactured by Sumitomo 3M Limited), Megafac (registered trademark) F142D, F171, F172, F173, F177, F183, F554, and F554 R30, RS-718-K (manufactured by DIC Corporation), EFTOP (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronic Chemicals, Inc.), Surflon (registered trademark) S381, S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.), and E5844 (manufactured by Daikin Fine Chemical Laboratory Co., Ltd.).

  The silicone surfactant further includes the above-mentioned silicone surfactant having a fluorine atom. Examples of the silicone-based surfactant having a fluorine atom include Megafac (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

The content of the leveling agent (F) is preferably from 0.001% by mass to 0.2% by mass, and more preferably from 0.002% by mass to 0.1% by mass, based on the total amount of the colored curable resin composition. %, More preferably 0.01 to 0.05% by mass. The 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 curable resin composition of the present invention, if necessary, fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents, and other additives known in the art. May be included.

<Method for producing colored curable resin composition>
The colored curable resin composition of the present invention includes, for example, a colorant (A), a resin (B), a polymerizable compound (C), a polymerization initiator (D), and a solvent (E) used as needed. It can be prepared by mixing a leveling agent (F), a polymerization initiation assistant (D1), a thiol compound (T) and other components.
When the pigment (A2) is used, it is preferable that the pigment (A2) is previously mixed with part or all of the solvent (E) and dispersed using a bead mill or the like until the average particle diameter of the pigment becomes about 0.2 μm or less. At this time, if necessary, a part or all of the pigment dispersant and the resin (B) may be blended. The desired colored curable resin composition can be prepared by mixing the remaining components with the pigment dispersion obtained in this manner so as to have a predetermined concentration.
The dye (A1) may be dissolved in part or all of the solvent (E) in advance to prepare a solution. The solution is preferably filtered with a filter having a pore size of about 0.01 to 1 μm.
It is preferable to filter the colored curable resin composition after mixing with a filter having a pore size of about 0.01 to 10 μm.

<Method for Manufacturing Color Filter and Liquid Crystal Display>
Examples of a method for forming a color filter using the colored curable resin composition of the present invention include a photolithographic method and a method using an inkjet device. The photolithographic method is, for example, a colored curable resin composition of the present invention is applied on a substrate, and dried by removing volatile components such as a solvent to form a colored composition layer. And exposing the colored composition layer to develop. After development, a colored pattern can be formed by heating if necessary. In the method for forming a colored pattern, a colored coating film that is a cured product of the colored composition layer can be formed by not using and / or developing a photomask during exposure. The color pattern and the color coating film thus obtained can be used as a color filter.

As the substrate, a glass plate, a resin plate, silicon, or a substrate on which aluminum, silver, a silver / copper / palladium alloy thin film is formed, or the like is used. On these substrates, another color filter layer, a resin layer, a transistor, a circuit, and the like may be formed.
The thickness of the color filter to be produced is not particularly limited and can be appropriately adjusted depending on the intended use and the like, and is, for example, 0.1 to 30 μm, preferably 1 to 20 μm, and more preferably 1 to 6 μm. .

The formation of each color pixel by the photolithographic method can be performed by a known or commonly used device or condition. For example, it can be manufactured as follows.
First, a colored curable resin composition is applied on a substrate, dried by heating (pre-baking) and / or drying under reduced pressure to remove volatile components such as a solvent and dried to obtain a smooth colored composition layer.
Examples of the coating method include a spin coating method, a slit coating method, a slit and spin coating method, and the like.

Next, the coloring composition layer is exposed through a photomask for forming a target coloring pattern.
Use of an exposure apparatus such as a mask aligner and a stepper can uniformly irradiate a parallel light beam on the entire exposure surface and perform accurate alignment between the photomask and the substrate on which the coloring composition layer is formed. Is preferred.

A colored pattern is formed on the substrate by developing the exposed colored composition layer by contacting it with a developer. By the development, the unexposed portions of the colored composition layer are dissolved in the developer and removed. As the developer, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogencarbonate, sodium carbonate, tetramethylammonium hydroxide or the like is preferable.
The developing method may be any of a paddle method, a dipping method, a spray method and the like. Further, the substrate may be inclined at an arbitrary angle during development.
After development, it is preferable to wash with water.

  Further, it is preferable to perform post-baking on the obtained colored pattern.

  According to the colored curable resin composition of the present invention, a color filter having particularly excellent pattern shape can be produced. The color filter is useful as a color filter used in a display device (for example, a liquid crystal display device, an organic EL device, electronic paper, or the like) and a solid-state imaging device.

  Hereinafter, the present invention will be described more specifically with reference to Examples. However, the present invention is not limited to the following Examples, and may be appropriately modified within a range that can conform to the purpose of the preceding and the following. It is, of course, possible to implement them, and all of them are included in the technical scope of the present invention. In the following, “parts” means “parts by mass” and “%” means “% by mass” unless otherwise specified.

[Synthesis Example 1]
A mixture of a compound represented by the formula (A0-1) and a compound represented by the formula (A0-2) (trade name: Chugai Aminol Fast Pink R; manufactured by Chugai Chemical Co., Ltd.) was placed in a flask equipped with a condenser and a stirrer. , 150 parts of chloroform and 8.9 parts of N, N-dimethylformamide were added, and 10.9 parts of thionyl chloride was added dropwise while stirring at 20 ° C or lower. After the completion of the dropwise addition, the temperature was raised to 50 ° C., the reaction was maintained at the same temperature for 5 hours, and then cooled to 20 ° C. A mixture of 12.5 parts of 2-ethylhexylamine and 22.1 parts of triethylamine was added dropwise to the cooled reaction solution while maintaining the temperature at 20 ° C. or lower with stirring. Thereafter, the mixture was reacted by stirring at the same temperature for 5 hours. Next, the solvent was distilled off from the obtained reaction mixture using a rotary evaporator, and a small amount of methanol was added to the reaction mixture from which the solvent had been distilled off, followed by vigorous stirring. The resulting mixture was added to a mixed solution of 375 parts of ion-exchanged water with stirring to precipitate crystals. The precipitated crystals are separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C. to obtain a dye (Aa-1) (of a compound represented by the formulas (A1-1) to (A1-8)). Mixture) 11.3 parts were obtained.

[Synthesis Example 2]
In a flask equipped with a reflux condenser, a dropping funnel and a stirrer, nitrogen was flowed at 0.02 L / min to form a nitrogen atmosphere, and 200 parts by mass of 3-methoxy-1-butanol and 105 parts by mass of 3-methoxybutyl acetate were put therein. Heat to 70 ° C. with stirring. Then, 60 parts by mass of methacrylic acid, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl acrylate (compound represented by formula (BI-1) and represented by formula (BII-1)) A mixture was prepared by dissolving 240 parts by mass of 140 parts by mass of 3-methoxybutyl acetate to prepare a solution. The solution was added using a dropping funnel over 4 hours. , And dropped into a flask kept at 70 ° C. On the other hand, a solution prepared by dissolving 30 parts by mass of a polymerization initiator 2,2′-azobis (2,4-dimethylvaleronitrile) in 225 parts by mass of 3-methoxybutyl acetate was added to another flask for 4 hours using another dropping funnel. It was dropped inside. After completion of the dropwise addition of the polymerization initiator solution, the mixture was maintained at 70 ° C. for 4 hours, and then cooled to room temperature to obtain a resin having a solid content of 32.6 mass% and an acid value of 110 mg-KOH / g (solid content). A B′1 solution was obtained. The weight average molecular weight Mw of the obtained resin Aa was 13,400, and the molecular weight distribution was 2.50.

The measurement of the weight average molecular weight (Mw) and the number average molecular weight (Mn) of the resin obtained in the synthesis example was performed using the GPC method under the following conditions.
Apparatus: K2479 (manufactured by Shimadzu Corporation)
Column: SHIMADZU Shim-pack GPC-80M
Column temperature; 40 ° C
Solvent; THF (tetrahydrofuran)
Flow rate: 1.0 mL / min
Detector; RI
Standard material for calibration; TSK STANDARD POLYSTYRENE F-40, F-4, F-228, A-2500, A-500 (manufactured by Tosoh Corporation)
The ratio of the weight average molecular weight and the number average molecular weight in terms of polystyrene (Mw / Mn) obtained above was defined as the molecular weight distribution.

Examples 1 to 7, Comparative Examples 1 to 6
(Preparation of colored curable resin composition)
Each component was mixed to obtain the composition shown in Table 10 to obtain a colored curable resin composition.

In Table 10, "P1-1" used was an acrylic pigment dispersant mixed with the amount of propylene glycol monomethyl ether acetate described in "E-1 (Note 2)" and dispersed in advance.
The column “E-1 (Note 1)” represents the total content of propylene glycol monomethyl ether acetate including (Note 2).

重合開始剤（Ｄ）：Ｄ−２：１，２−オクタジオン，１−［４−（フェニルチオ）フェニル］−，２−（Ｏ−ベンゾイルオキシム）（商品名イルガキュアＯＸＥ０１、チバ・スペシャルティー・ケミカルズ社製）
溶剤（Ｅ−１）：プロピレングリコールモノメチルエーテルアセテート
レベリング剤（Ｆ）：ポリエーテル変性シリコーンオイル
（トーレシリコーンＳＨ８４００：東レ・ダウコーニング（株）製） Colorant (A): Aa-1: Dye (Aa-1)
Colorant (A): P1-1: C.I. I. Pigment Blue 15: 6 (pigment) Resin (B): Resin B'1 (solid content conversion)
Polymerizable compound (C): C-1: KAYARAD (registered trademark) DPHA (manufactured by Nippon Kayaku Co., Ltd.)
Polymerizable compound (C): C-2: NK ester A-TMM-3LM-N (manufactured by Shin-Nakamura Chemical Co., Ltd.)
Polymerizable compound (C): C-3: NK ester A-9550 (manufactured by Shin-Nakamura Chemical Co., Ltd.) Polymerization initiator (D): D-1: Compound represented by formula (d1-40)

Polymerization initiator (D): D-2: 1,2-octadione, 1- [4- (phenylthio) phenyl]-, 2- (O-benzoyl oxime) (trade name Irgacure OXE01, Ciba Specialty Chemicals) Made)
Solvent (E-1): Propylene glycol monomethyl ether acetate leveling agent (F): Polyether-modified silicone oil (Toray Silicone SH8400: manufactured by Dow Corning Toray)

  According to the method described in JP-T-2014-500852, the compound represented by the above formula (d1-40) was prepared.

[Formation of coating film 1]
A 2-inch square glass substrate (Eagle XG; manufactured by Corning Incorporated) was washed with a neutral detergent, water and alcohol sequentially, and then dried. On this glass substrate, the colored curable resin compositions of Examples 1 and 2 and Comparative Example 1 obtained above were spin-coated so that the film thickness after post-baking was 3.0 μm, respectively. Was prebaked at 190 ° C. for 3 minutes in a clean oven. Then, it heated at 230 degreeC for 20 minutes, and obtained the coating film.
[Formation of coating film 2]
A 2-inch square glass substrate (Eagle XG; manufactured by Corning Incorporated) was washed with a neutral detergent, water and alcohol sequentially, and then dried. On this glass substrate, the colored curable resin compositions of Examples 1 to 7 and Comparative Examples 1 to 6 obtained above were spin-coated, respectively, so that the film thickness after post-baking was 2.5 μm. And then in a clean oven at 190 ° C. for 3 minutes. Then, it heated at 230 degreeC for 20 minutes, and obtained the coating film.

[Production of pattern 1]
The colored curable resin compositions of Examples 1 and 2 and Comparative Example 1 were each placed on a 2-inch square glass substrate (Eagle 2000; manufactured by Corning Incorporated) so that the film thickness after post-baking was 2.0 μm. And then pre-baked at 100 ° C. for 3 minutes to form a composition layer. After cooling, the distance between the substrate on which the composition layer was formed and the quartz glass photomask was set to 80 μm, and exposure was performed at 40 mJ / cm ^{2 in} an air atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). It was irradiated with light in an amount (based on 365 nm). Incidentally, a photomask on which a 50 μm line and space pattern was formed was used. The composition layer after light irradiation is developed by immersing in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 ° C. for 60 seconds, washed with water, and washed in an oven at 230 ° C. A pattern was obtained by performing post-baking at 20 ° C. for 20 minutes. When the film thickness of the obtained pattern was measured using a film thickness measurement device (DEKTAK3; manufactured by Japan Vacuum Engineering Co., Ltd.), it was confirmed to be 2.0 μm.
[Production of pattern 2]
Each of the colored curable resin compositions of Examples 1 to 7 and Comparative Examples 1 to 6 was formed on a 2-inch square glass substrate (Eagle 2000; manufactured by Corning Incorporated) to a thickness of 2.5 μm after post-baking. After being applied by a spin coating method, the composition was prebaked at 100 ° C. for 3 minutes to form a composition layer. After cooling, the distance between the substrate on which the composition layer was formed and the quartz glass photomask was set to 80 μm, and exposure was performed at 40 mJ / cm ^{2 in} an air atmosphere using an exposure machine (TME-150RSK; manufactured by Topcon Corporation). It was irradiated with light in an amount (based on 365 nm). Incidentally, a photomask on which a 50 μm line and space pattern was formed was used. The composition layer after light irradiation is developed by immersing in an aqueous solution containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide at 25 ° C. for 60 seconds, washed with water, and washed in an oven at 230 ° C. A pattern was obtained by performing post-baking at 20 ° C. for 20 minutes. About the obtained pattern, the film thickness was measured using the film thickness measuring device (DEKTAK3; manufactured by Japan Vacuum Engineering Co., Ltd.).

[Colored pattern shape evaluation 1]
The colored patterns of Examples 1 and 2 and Comparative Example 1 obtained in Pattern Production 1 were shaped using a scanning electron microscope (S-4000; manufactured by Hitachi High-Technologies Corporation, magnification 10000 times). Observed. In FIG. 1, when the shape (○) is indicated by (p1), when the inorganic film is laminated on the colored pattern, the inorganic film tends not to crack or peel. Table 11 shows the results.
[Colored pattern shape evaluation 2]
For the colored patterns obtained from each of the compositions of Examples 1 to 7 and Comparative Examples 1 to 6 obtained in Pattern Production 2, a scanning electron microscope (S-4000; manufactured by Hitachi High-Technologies Corporation, magnification: (10000 times) to observe the shape. In FIG. 2, when the shape (形状) is indicated by (p3), when the inorganic film is laminated on the colored pattern, the inorganic film tends not to crack or peel. Table 12 shows the results.
<Chromaticity evaluation>
The color patterns obtained from the compositions of Examples 5 to 7 were measured for spectroscopy using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation) and CIE using the characteristic function of the C light source. The xy chromaticity coordinates (x, y) and the tristimulus value Y in the XYZ color system were measured. The higher the value of Y, the higher the brightness. Table 12 shows the results.

From the above results, it was confirmed that the pattern formed by the colored curable resin composition of the present invention was excellent in pattern shape. From this, it is understood that according to the present invention, a colored curable resin composition capable of producing a display device having excellent display characteristics was provided.

ADVANTAGE OF THE INVENTION According to this invention, it becomes possible to provide the coloring curable resin composition which can form a favorable coloring pattern.
The pattern and the coating film obtained from the colored curable resin composition of the present invention are a transparent film, a pattern, a photo spacer, an overcoat, an insulating film, and a liquid crystal alignment control which constitute a part of a color filter substrate and / or an array substrate. It is useful as a projection, a microlens, a coating layer, and the like, and is provided with a color filter substrate, an array substrate, or the like including these coating films or patterns as a part of its component parts, and further includes the color filter substrate and / or the array substrate. For example, a liquid crystal display device, an organic EL device, and electronic paper.

Claims (7)

Contains colorant, resin, polymerizable compound and polymerization initiator,
Including a dye and a pigment as the colorant,
A colored curable resin composition containing a compound represented by the following formula (d1) as the polymerization initiator.

[In the formula (d1),
R ^d1 represents an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, a heterocyclic group having 3 to 36 carbon atoms which may have a substituent, or a substituent. Represents an alkyl group having 1 to 15 carbon atoms which may be substituted or an aralkyl group having 7 to 33 carbon atoms which may have a substituent, and a methylene group (—CH ₂ —) included in the alkyl group or the aralkyl group Is -O-, -CO-,
—S—, —SO ₂ — or —N (R ^d5 ) — may be substituted.
R ^d2 represents an aromatic hydrocarbon group having 6 to 18 carbon atoms, a heterocyclic group having 3 to 36 carbon atoms, or an alkyl group having 1 to 10 carbon atoms.
R ^d3 represents an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, or a heterocyclic group having 3 to 36 carbon atoms which may have a substituent.
R ^d4 represents an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, or an aliphatic hydrocarbon group having 1 to 15 carbon atoms which may have a substituent; a methylene group contained in the aliphatic hydrocarbon group (-CH ₂ -) is, -O -, - CO- or -S- may be replaced, a methine group (-CH contained in the aliphatic hydrocarbon group <) May be replaced by —PO ₃ <, and a hydrogen atom contained in the aliphatic hydrocarbon group may be replaced by an OH group.
R ^d5 represents an alkyl group having 1 to 10 carbon atoms, and the methylene group (—CH ₂ —) contained in the alkyl group may be replaced by —O— or —CO—. ] The colored curable resin composition according to claim 1, wherein the dye contains at least one dye selected from the group consisting of a xanthene dye, a triarylmethane dye, a compound represented by the formula (Ab2), and a coumarin dye.

[In the formula (Ab2), R ^{41 to} R ⁴⁴ each independently represent a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aromatic group having 6 to 20 carbon atoms which may have a substituent. Represents a hydrocarbon group or an aralkyl group having 7 to 30 carbon atoms which may have a substituent, and in the saturated hydrocarbon group having 1 to 20 carbon atoms, a hydrogen atom contained in the saturated hydrocarbon group is substituted. Alternatively, it may be substituted with an unsubstituted amino group or a halogen atom, and when the saturated hydrocarbon group has 2 to 20 carbon atoms, the methylene group contained in the saturated hydrocarbon group is an oxygen atom or -CO- May be substituted. R ⁴¹ and R ⁴² may combine to form a ring together with the nitrogen atom to which they bind, or R ⁴³ and R ⁴⁴ may combine to form a ring together with the nitrogen atom to which they bind.
R ^{47 to} R ⁵⁴ each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxy group, or an alkyl group having 1 to 8 carbon atoms, and when the alkyl group has 2 to 8 carbon atoms, methylene group constituting the alkyl group may be substituted by an oxygen atom or a -CO-, linked with R ⁴⁸ and R ⁵² each other, -NH -, - S- or SO ₂ - have the form You may.
Ring T ¹ represents an aromatic heterocyclic ring having 3 to 10 carbon atoms which may have a substituent.
[Y] ^m- represents an arbitrary m-valent anion.
m represents an arbitrary natural number. ]   The colored curable resin composition according to claim 1, wherein the colorant includes a phthalocyanine pigment.   The colored curable resin composition according to any one of claims 1 to 3, wherein the content of the pigment is 1% by mass or more and 50% by mass or less based on the total amount of the solid content.   The content ratio between the polymerization initiator and the polymerizable compound (polymerization initiator / polymerizable compound) is 4/1000 or more and 35/100 or less on a mass basis. Colored curable resin composition.   A color filter formed from the colored curable resin composition according to claim 1.   A liquid crystal display device including the color filter according to claim 6.

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