JP6518436B2 - Colored curable resin composition - Google Patents

Description

  The present invention relates to a colored curable resin composition.

A color filter formed from a colored curable resin composition is used in a display device such as a liquid crystal display panel, an electroluminescence panel, and a plasma display panel, and a color filter having good brightness, good contrast and good resolution is required. It was being done. In order to realize a color filter having good lightness, good contrast, and good resolution, a colored curable resin composition containing a dye as a coloring agent has been studied, but the heat resistance, by containing the dye, It has been a problem that the chemical resistance and the like decrease.
Patent Document 1 describes C.I. I. Pigment blue 15: 6 and C.I. I. A colored curable resin composition comprising Acid Red 52 and a dye represented by the following formula, which is C.I. I. The content of Acid Red 52 is C.I. I. The pigmented curable resin composition which is 14.7 mass parts with respect to 100 mass parts of pigment blue 15: 6 is described.

JP, 2013-144724, A

  The color filter formed from the above-mentioned colored curable resin composition can not always satisfy both the heat resistance and the lightness.

［式中、ｋ１、ｋ２、ｋ３及びｋ４は、それぞれ独立して、０〜４の整数を表し、１≦ｋ１＋ｋ２＋ｋ３＋ｋ４≦１６である。
Ｘ_ａ ⁻、Ｘ_ｂ ⁻、Ｘ_ｃ ⁻及びＸ_ｄ ⁻、は、それぞれ独立して、−ＣＯ_３ ⁻又は−ＳＯ_３ ⁻を表す。
Ａ_ａ ^＋、Ａ_ｂ ^＋、Ａ_ｃ ^＋及びＡ_ｄ ^＋は、それぞれ独立して、ナトリウムイオン、カリウムイオン又は式（ｂ）で表されるカチオンを表す。

式（ｂ）中、Ｒ^１００、Ｒ^１０１、Ｒ^１０２及びＲ^１０３は、それぞれ独立して、水素原子又は炭素数１〜３０の炭化水素基を表す。］
［２］キサンテン染料が、Ｃ．Ｉ．アシッド５２又は下記式（Ｉ）で表される化合物である［１］に記載の着色硬化性樹脂組成物。

［式（Ｉ）中、Ｒ^１、Ｒ^２、Ｒ^３及びＲ^４は、それぞれ独立に、置換基を有していてもよい炭素数２〜１０の１価の飽和炭化水素基又は置換基を有していてもよいアリール基を表す。
Ｒ^５１、Ｒ^５２及びＲ^５３は、それぞれ独立して、水素原子、−ＳＯ_３ ⁻、−ＳＯ_３Ｈ又は−ＳＯ_３ ⁻Ｚ^＋を表す。
Ｘ^＋およびＺ^＋は、それぞれ独立に、^＋Ｎ（Ｒ^１３）_４、Ｎａ^＋又はＫ^＋を表し、Ｒ^１３は、水素原子又は炭素数１〜２０の１価の飽和炭化水素基を表す。Ｒ^１３は、同一であってもよいし異なっていてもよい。
ａは、１〜４の整数を表す。］
［３］着色剤（Ａ）が、青色又は紫色染料（Ａ２）をさらに含む［１］又は［２］に記載の着色硬化性樹脂組成物。 The present invention includes the following inventions.
[1] A colored curable resin composition comprising a colorant (A), a resin (B), a polymerizable compound (C) and a polymerization initiator (D),
A compound represented by the formula (a):
Colored curable resin composition comprising at least one selected from the group consisting of xanthene dyes and salts of xanthene dyes and cyanine dyes.

[Wherein, k 1, k 2, k 3 and k 4 each independently represent an integer of 0 to 4 and 1 ≦ k 1 + k 2 + k 3 + k 4 ≦ 16.
_{^{X a -, X b -,}} X c - and _{X d} ^-, each independently, -CO ₃ ^- or -SO ₃ ^- represents a.
A _a ⁺ , A _b ⁺ , A _c ⁺ and A _d ⁺ each independently represent a sodium ion, a potassium ion or a cation represented by the formula (b).

In formula (b), R ¹⁰⁰ , R ¹⁰¹ , R ¹⁰² and R ¹⁰³ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms. ]
[2] The xanthene dye is C.I. I. Colored curable resin composition as described in [1] which is acid 52 or a compound represented by the following formula (I).

[In formula (I), R ¹ , R ² , R ³ and R ⁴ are each independently a monovalent saturated hydrocarbon group having 2 to 10 carbon atoms which may have a substituent or a substituent Represents an aryl group which may be possessed.
R ^{51, R 52} and ^{R 53} are each independently a hydrogen _atom, ^-SO 3 -, -SO ₃ H or _-SO ³ - represents a ^{Z +.}
X ⁺ and Z ⁺ each independently represent ⁺ N (R ¹³ ) ₄ , Na ⁺ or K ⁺ , and R ¹³ represents a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms. R ¹³ may be the same or different.
a represents an integer of 1 to 4; ]
[3] The colored curable resin composition according to [1] or [2], wherein the colorant (A) further comprises a blue or violet dye (A2).

  According to the colored curable resin composition of the present invention, a color filter having good heat resistance and good brightness can be produced.

The colored curable resin composition of the present invention comprises a colorant (A), a resin (B), a polymerizable compound (C) and a polymerization initiator (D).
The colored curable resin composition of the present invention preferably contains at least one selected from solvent (E) and leveling agent (F).
The colored curable resin composition of the present invention may contain a polymerization initiation aid (D1).

<Colorant (A)>
The colorant (A) is a compound represented by the formula (a) (hereinafter sometimes referred to as a compound (a)):
And at least one selected from the group consisting of xanthene dyes and salts of xanthene dyes and cyanine dyes.
The colorant (A) may further contain a blue or purple dye (A2) (hereinafter sometimes referred to as "dye (A2)"). The coloring agent (A) may also contain a dye (Ac) (hereinafter sometimes referred to as "dye (Ac)") different from the pigment (A1) and the blue or purple dye (A2).
In the present application, “CI” means color index (CI).

［式中、ｋ１、ｋ２、ｋ３及びｋ４は、それぞれ独立して、０〜４の整数を表し、１≦ｋ１＋ｋ２＋ｋ３＋ｋ４≦１６である。
Ｘ_ａ ⁻、Ｘ_ｂ ⁻、Ｘ_ｃ ⁻及びＸ_ｄ ⁻、は、それぞれ独立して、−ＣＯ_３ ⁻又は−ＳＯ_３ ⁻を表す。
Ａ_ａ ^＋、Ａ_ｂ ^＋、Ａ_ｃ ^＋及びＡ_ｄ ^＋は、それぞれ独立して、ナトリウムイオン、カリウムイオン又は式（ｂ）で表されるカチオンを表す。

式（ｂ）中、Ｒ^１００、Ｒ^１０１、Ｒ^１０２及びＲ^１０３は、それぞれ独立して、水素原子、炭素数１〜３０の炭化水素基、又は炭素数６〜３０のヘテロ環基を表す。］ <Compound (a)>

[Wherein, k 1, k 2, k 3 and k 4 each independently represent an integer of 0 to 4 and 1 ≦ k 1 + k 2 + k 3 + k 4 ≦ 16.
_{^{X a -, X b -,}} X c - and _{X d} ^-, each independently, -CO ₃ ^- or -SO ₃ ^- represents a.
A _a ⁺ , A _b ⁺ , A _c ⁺ and A _d ⁺ each independently represent a sodium ion, a potassium ion or a cation represented by the formula (b).

In formula (b), R ¹⁰⁰ , R ¹⁰¹ , R ¹⁰² and R ¹⁰³ each independently represent a hydrogen atom, a hydrocarbon group having 1 to 30 carbon atoms, or a heterocyclic group having 6 to 30 carbon atoms. ]

k1, k2, k3 and k4 each independently represent an integer of 0 to 4; However, it is preferable that 1 ≦ k1 + k2 + k3 + k4 ≦ 16 and 1 ≦ k1 + k2 + k3 + k4 ≦ 2.
The hydrocarbon group represented by R ¹⁰⁰ , R ¹⁰¹ , R ¹⁰² and R ¹⁰³ includes methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl and n-heptyl A linear alkyl group having 1 to 30 carbon atoms such as n-octyl group, n-nonyl group, n-decyl group, n-dodecyl group, n-hexadecyl group and n-icosyl group; isopropyl group, isobutyl group And branched alkyl groups having 3 to 30 carbon atoms such as sec-butyl, tert-butyl, isopentyl, neopentyl and 2-ethylhexyl; cyclopropyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclo A C3-C30 alicyclic saturated hydrocarbon group, such as an octyl group and a tricyclodecyl group, is mentioned. Preferably it is a C1-C8 alkyl group, More preferably, it is a C1-C4 alkyl group.

Specific examples of the compound (a) include those described below.

The content of the compound (a) is usually 0.1 to 99% by mass, preferably 0.1 to 20% by mass, preferably 0.1 to 10% by mass, based on the total amount of the colorant (A). It is more preferable that
The compound (a) may contain two or more.

［式（Ｉ）中、Ｒ^１、Ｒ^２、Ｒ^３及びＲ^４は、それぞれ独立に、置換基を有していてもよい炭素数２〜１０の１価の飽和炭化水素基又は置換基を有していてもよいアリール基を表す。
Ｒ^５１、Ｒ^５２及びＲ^５３は、それぞれ独立して、水素原子、−ＳＯ_３ ⁻、−ＳＯ_３Ｈ又は−ＳＯ_３ ⁻Ｚ^＋を表す。
Ｘ^＋およびＺ^＋は、それぞれ独立に、^＋Ｎ（Ｒ^１３）_４、Ｎａ^＋又はＫ^＋を表し、Ｒ^１３は、水素原子又は炭素数１〜２０の１価の飽和炭化水素基を表す。Ｒ^１３は、同一であってもよいし異なっていてもよい。
ａは、１〜４の整数を表す。］ <Xanthane dye>
The xanthene dye means a dye containing a compound having a xanthene skeleton. The xanthene dye is preferably a xanthene dye having two —SO ₃ ^— groups as a substituent, and C.I. I. Acid Red 52 and its analogues are more preferred. C. I. The analogue of Acid Red 52 means a compound represented by Formula (I) (hereinafter sometimes referred to as Compound (I)).
<Compound (I)>

[In formula (I), R ¹ , R ² , R ³ and R ⁴ are each independently a monovalent saturated hydrocarbon group having 2 to 10 carbon atoms which may have a substituent or a substituent Represents an aryl group which may be possessed.
R ^{51, R 52} and ^{R 53} are each independently a hydrogen _atom, ^-SO 3 -, -SO ₃ H or _-SO ³ - represents a ^{Z +.}
X ⁺ and Z ⁺ each independently represent ⁺ N (R ¹³ ) ₄ , Na ⁺ or K ⁺ , and R ¹³ represents a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms. R ¹³ may be the same or different.
a represents an integer of 1 to 4; ]

As a C2-C10 monovalent saturated hydrocarbon group represented by R ¹ , R ² , R ³ and R ⁴ , an ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group can be mentioned Group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, decyl group, 1-methylbutyl group, 1,1,3,3-tetramethylbutyl group, 1, A linear or branched alkyl group having a carbon number of 3 to 10 such as 5-dimethylhexyl group, 1,6-dimethylheptyl group, 2-ethylhexyl group, 1,1,5,5-tetramethylhexyl group; cyclopropyl And cycloalkyl groups having 3 to 10 carbon atoms, such as cyclobutyl, cyclopentyl, cyclohexyl and adamantyl, and the like, with n-propyl, n-butyl and 2-ethylhexyl being preferred

（＊は、結合手を表す。） The hydrogen atom contained in the C2-C10 monovalent saturated hydrocarbon group represented by R ¹ , R ² , R ³ and R ⁴ may be substituted by a hydroxy group, an alkoxy group or a halogen atom .
The halogen atom includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
Examples of the alkoxy group include, for example, 1 to 20 carbon atoms such as methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, 2-ethylhexyloxy and icosyloxy groups. And an alkoxy group of
As a C1-C10 monovalent | monohydric saturated hydrocarbon group substituted by the halogen atom, a heptafluoropropyl group, a 1, 1- difluoropropyl group, 3, 3, 3- trifluoropropyl group, nona fluoro butyl group , 2,2-Difluorobutyl, undecafluoropentyl, 3- (trifluoromethyl) -3,4,4,4-pentafluorobutyl, 6,6,6-trifluorohexyl, heptachloropropyl Group, heptabromopropyl group, 3,3,3-triiodopropyl group, 2,2-dichloro-3,3,3-trifluoropropyl group, etc. are mentioned, and preferably a group represented by the following formula is preferable .

(* Represents a bond.)

As an aryl group represented by R ¹ , R ² , R ³ and R ⁴ , an aromatic hydrocarbon group having 6 to 10 carbon atoms such as phenyl group and naphthalene group; 6 to 6 carbon atoms such as benzyl group and phenethyl group And an aralkyl group of 10, and the like, and a phenyl group is preferable.

The aryl group represented by R ¹ , R ² , R ³ and R ⁴ is an alkyl group having 1 to 20 carbon atoms such as methyl group, ethyl group or n-propyl group; methoxy group, ethoxy group, propoxy group, butoxy group It may be substituted by an alkoxy group having 1 to 20 carbon atoms such as a group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, 2-ethylhexyloxy group and icosyloxy group; and a hydroxy group.
The substituents R ^{1, R} 2, an aryl group represented by ^{R 3} and ^{R 4} have, preferably an alkyl group having 1 to 20 carbon atoms, more preferably an alkyl group having 1 to 10 carbon atoms.

The monovalent saturated hydrocarbon group having 1 to 20 carbon atoms represented by R ^13, a methyl group, an ethyl group, n- propyl group, n- butyl group, n- pentyl group, n- hexyl, n- A linear alkyl group having 1 to 20 carbon atoms such as heptyl group, n-octyl group, n-nonyl group, n-decyl group, n-dodecyl group, n-hexadecyl group and n-icosyl group; isopropyl group, isobutyl group Branched alkyl group having 3 to 20 carbon atoms such as sec-butyl group, tert-butyl group, isopentyl group, neopentyl group and 2-ethylhexyl group; cyclopropyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, A C3-C20 alicyclic saturated hydrocarbon group, such as a cyclooctyl group and a tricyclodecyl group, is mentioned.

Z ⁺ represents ⁺ N (R ¹³ ) ₄ , Na ⁺ or K ⁺ , and R ¹³ may be the same or different.
-SO ₃ ^- as Z ^{+ _{is, -SO 3 - + N (R}} 13) 4 are preferred.

R ¹ , R ² , R ³ and R ⁴ are preferably each independently an alkyl group having 3 to 10 carbon atoms or a phenyl group which may have a substituent, and an alkyl having 3 to 8 carbon atoms It is more preferable that it is a group or a phenyl group which may be substituted by an alkyl group having 1 to 10 carbon atoms.
In R ¹ , R ² , R ³ and R ⁴ , R ¹ and R ³ are preferably the same group, and R ² and R ⁴ are preferably the same group.
a represents an integer of 1 to 4, preferably 1 or 2, and more preferably 1.
R ⁵¹ , R ⁵² and R ⁵³ are preferably all the same, and more preferably all hydrogen atoms.

  Compound (I) can be produced, for example, according to WO 2013/050431.

Specific examples of xanthene dyes include C.I. I. Besides Acid Red 52, the compounds shown below can be mentioned. In the following formulas, R ²⁶ and R ⁴⁰ each independently represent a 2-ethylhexyl group.

As the xanthene dye (A3), commercially available xanthene dyes (for example, "Chugai Amino Fast Fast RH / C" manufactured by Chuo Kasei Co., Ltd .; The compounds described are also mentioned. Moreover, it can also be synthesize | combined on reference to Unexamined-Japanese-Patent No. 2010-32999 by using the commercially available xanthene dye as a starting material.

The content of the xanthene dye is usually 0.1 to 30 parts by mass, preferably 0.1 to 20 parts by mass, more preferably 0.1 to 10 parts by mass, per 100 parts by mass of the compound (a). It is a department.
Two or more xanthene dyes may be contained.

<Salt of xanthene dye and cyanine dye>
The salt of xanthene dye and cyanine dye means a salt composed of an anion derived from a xanthene compound and a cation derived from a cyanine compound.
The cyanine compound refers to a compound having a structure in which two heterocyclic rings are conjugated and double bonded with an odd number of methine groups in the molecule.

［式（１ｂ）中、環Ｚ^１及び環Ｚ^２は、それぞれ独立に、置換されていてもよい複素環を表す。
Ｙ^１、Ｙ^２及びＹ^３は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、ニトロ基、炭素数１〜８の脂肪族炭化水素基又は炭素数６〜１２のアリール基を表し、Ｙ^１、Ｙ^２及びＹ^３から選ばれる２つが互いに結合して環を形成してもよい。
ｕは、０以上３以下の整数を表す。
Ｘ^ｂ１−は対アニオンを表し、ｂ１は１又は２を表す。 As an anion derived from a xanthene compound, the anion derived from the xanthene dye mentioned above is mentioned.
The cyanine compound is preferably a compound represented by the formula (1b) or a compound represented by the formula (1c).

[In formula (1b), ring Z ¹ and ring Z ² each independently represent an optionally substituted heterocycle.
Y ¹ , Y ² and Y ³ each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an aliphatic hydrocarbon group having 1 to 8 carbon atoms or an aryl group having 6 to 12 carbon atoms; Two selected from ¹ , Y ² and Y ³ may combine with each other to form a ring.
u represents an integer of 0 or more and 3 or less.
X ^B1- represents a counter anion, b1 represents 1 or 2.

式（１ｃ）中、環Ｚ^３、環Ｚ^４、環Ｚ^５及び環Ｚ^６は、それぞれ独立に、置換されていてもよい複素環を表す。
Ｙ^４、Ｙ^５、Ｙ^６、Ｙ^７、Ｙ^８及びＹ^９は、それぞれ独立に、水素原子、ハロゲン原子、シアノ基、ニトロ基、炭素数１〜８の脂肪族炭化水素基又は炭素数６〜１２のアリール基を表し、Ｙ^４、Ｙ^５、Ｙ^６、Ｙ^７、Ｙ^８及びＹ^９から選ばれる２つが互いに結合して環を形成してもよい。
Ｌ^１は、置換されていてもよい炭素数１〜１６の２価の炭化水素基を表す。
ｖ及びｗは、それぞれ独立に、０以上３以下の整数を表す。
Ｘ^ｃ１−は対アニオンを表し、ｃ１は１又は２を表す。

In formula (1c), ring Z ³ , ring Z ⁴ , ring Z ⁵ and ring Z ⁶ each independently represent an optionally substituted heterocycle.
Y ⁴ , Y ⁵ , Y ⁶ , Y ⁷ , Y ⁸ and Y ⁹ each independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an aliphatic hydrocarbon group having 1 to 8 carbon atoms, or 6 carbon atoms And an aryl group of 12 to 12 groups, and two selected from Y ⁴ , Y ⁵ , Y ⁶ , Y ⁷ , Y ⁸ and Y ⁹ may bond to each other to form a ring.
L ¹ represents a C 1-16 divalent hydrocarbon group which may be substituted.
v and w each independently represent an integer of 0 or more and 3 or less.
X ^c1- represents a counter anion, c1 represents 1 or 2.

The heterocycle represented by ring Z ¹ , ring Z ² , ring Z ³ , ring Z ⁴ , ring Z ⁵ and ring Z ⁶ contains at least one hetero atom as a constituent of the ring, and may be a single ring It may be a polycycle.
The hetero atom may be an atom selected from the elements of Group 15 or 16 in the periodic table, and examples thereof include a nitrogen atom, an oxygen atom, a sulfur atom, a selenium atom and a tellurium atom.
Examples of the heterocyclic ring include indole ring, benzoindole ring, indolenine ring, benzoindolenine ring, oxazole ring, benzoxazole ring, thiazole ring, benzothiazole ring, imidazole ring, benzoimidazole ring and quinoline ring.

As a substituent which the heterocycle represented by ring Z ¹ , ring Z ² , ring Z ³ , ring Z ⁴ , ring Z ⁵ and ring Z ⁶ may have,
C1-C6 fats such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl and tert-pentyl Group hydrocarbon group;
Aryl having 6 to 12 carbon atoms such as phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, xylyl group, mesityl group, o-cumenyl group, m-cumenyl group, p-cumenyl group, naphthyl group Group;
An aralkyl group having 7 to 10 carbon atoms such as benzyl group;
An alkoxy group having 1 to 6 carbon atoms, such as a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group and a pentyloxy group;
An aryloxy group having 6 to 10 carbon atoms such as phenoxy group;
A C7-10 aralkyloxy group such as a benzyloxy group;
A group having an ester bond such as methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, acetoxy group, benzoyloxy group;
Methylsulfamoyl group, dimethylsulfamoyl group, ethylsulfamoyl group, diethylsulfamoyl group, n-propylsulfamoyl group, di-n-propylsulfamoyl group, isopropylsulfamoyl group, diisopropylsulfoyl group Alkyl sulfamoyl groups having 1 to 8 carbon atoms, such as famoyl group, n-butylsulfamoyl group, di-n-butylsulfamoyl group, 2-ethylhexylsulfamoyl group;
An alkylsulfonyl group having 1 to 6 carbon atoms, such as methylsulfonyl group, ethylsulfonyl group, propylsulfonyl group, isopropylsulfonyl group, n-butylsulfonyl group, isobutylsulfonyl group, sec-butylsulfonyl group, tert-butylsulfonyl group and the like;
Halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom;
Vinyl group, allyl group, propen-2-yl group, methallyl group, but-3-en-1-yl group, but-3-en-2-yl group, but-3-en-3-yl group, penta Alkenyl groups having 2 to 6 carbon atoms, such as -4-en-1-yl;
Nitro group; cyano group etc. may be mentioned.
When such a substituent has a hydrogen atom, the hydrogen atom is, for example, a halogen atom such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom; a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group And alkoxy groups such as isobutoxy, sec-butoxy, tert-butoxy and pentyloxy; aryloxy groups such as phenoxy and benzyloxy; carboxy; cyano; nitro; acryloyloxy; methacryloyloxy It may be substituted by a group or the like.

Examples of the aliphatic hydrocarbon group having 1 to 8 carbon atoms represented by Y ¹ to Y ^9, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec- butyl group, tert- butyl group And pentyl, isopentyl, neopentyl, hexyl, heptyl, octyl and cyclohexyl groups.
The aryl group having 6 to 12 carbon atoms represented by Y ¹ to Y ^9, phenyl, o- tolyl, m- tolyl group, p- tolyl group, xylyl group, mesityl group, o- cumenyl group, m -Cumenyl group, p-cumenyl group, a naphthyl group etc. are mentioned.

The heterocycle represented by ring Z ¹ , ring Z ² , ring Z ³ , ring Z ⁴ , ring Z ⁵ and ring Z ⁶ is preferably an indole ring, a benzoindole ring, an indolenine ring or a benzoindolenine ring, Ring or indolenine ring is more preferred.
The heterocycle represented by ring Z ¹ , ring Z ² , ring Z ³ , ring Z ⁴ , ring Z ⁵ and ring Z ⁶ preferably has one or two alkyl groups or halogen atoms as substituents.
Y ^{1 to} Y ³ each independently represent a hydrogen atom, a cyano group, a halogen atom, or an aliphatic hydrocarbon group having 1 to 8 carbon atoms, or two of Y ^{1 to} Y ³ together form a ring It is preferable to form
Each of Y ^{1 to} Y ³ is independently preferably a hydrogen atom, a cyano group or a halogen atom, and more preferably a hydrogen atom.
Y ^{4 to} Y ⁹ each independently represent a hydrogen atom, a cyano group, a halogen atom or an aliphatic hydrocarbon group having 1 to 8 carbon atoms, or two of Y ^{4 to} Y ⁹ together form a ring It is preferable to form
Each of Y ^{4 to} Y ⁹ is independently preferably a hydrogen atom, a cyano group or a halogen atom, and more preferably a hydrogen atom.
u, v and w are preferably 1 in terms of the lightness of the obtained color filter.

Examples of the divalent hydrocarbon group represented by L ¹ include alkanediyl groups such as methylene group, ethylene group, ethanediyl group, propanediyl group, butanediyl group, tetramethylene group, pentamethylene group and hexamethylene group;
A bivalent alicyclic hydrocarbon group such as cyclopentandiyl group, cyclohexanediyl group, cyclohexenediyl group;
and divalent aromatic hydrocarbon groups such as o-phenylene group, m-phenylene group, p-phenylene group, and naphthylene group.
Examples of the substituent which the divalent hydrocarbon group may have include an amino group, a carboxy group, a cyano group, a nitro group, a halogen atom, a hydroxy group and the like.
L ¹ may be bonded to any position of ring Z ³ and ring Z ⁵ .
The bivalent hydrocarbon group is preferably an alkanediyl group having 1 to 16 carbon atoms, more preferably an alkanediyl group having 1 to 10 carbon atoms, and still more preferably an alkanediyl group having 3 to 8 carbon atoms.

^Examples of counter anions representing X ^b1- or X ^c1- include halide ions, ClO ₄ ⁻ , OH ⁻ , organic carboxylic acid anions, organic sulfonic acid anions, Lewis acid anions, organic metal complex anions, dye-derived anions, etc Be
The halide ^{ions, Cl -, Br -, I} - , and the like.
Examples of the organic carboxylate anion include benzoate ion, alkanoate ion, trihaloalkanoate ion, and nicotinate ion.
Examples of the organic sulfonate anion include benzene sulfonate ion, naphthalene sulfonate ion, p-toluene sulfonate ion, alkane sulfonate ion and the like.
As a Lewis acid anion, BF ₄ ⁻ , SbF ₆ ^{− and the} like can be mentioned.
As a pigment origin anion, the anion derived from a phthalocyanine compound, the anion derived from an azo compound, etc. are mentioned, Preferably, it is an anion derived from a phthalocyanine compound.

The organometallic complex anion consists of a central metal and a ligand, and as the ligand, an azo ligand, a bisphenyldithiol ligand, a thiocatechol chelate ligand, a thiobisphenolate chelate type Ligands, bisdiol-α-diketone ligands and the like can be mentioned. As a central metal, transition metals of Groups 3 to 11 in the periodic table, for example, scandium, yttrium, titanium, zirconium, hafnium, vanadium, niobium, tantalum, chromium, molybdenum, tungsten, manganese, technetium, rhenium, Iron, ruthenium, osmium, cobalt, rhodium, iridium, nickel, palladium, platinum, copper, silver, gold, cadmium, mercury and the like can be mentioned.
As said ligand, an azo-type ligand and a bisphenyl dithiol type ligand are preferable, and an azo-type ligand is more preferable.
As the central metal, cobalt, nickel and copper are preferable in terms of production cost and ease of handling.
Specifically, the organometallic complex anion is preferably an azo metal complex anion or a bisphenyldithiol metal complex anion in which the central metal is cobalt, nickel or copper, and an azo the central metal is cobalt, nickel or copper. Metal complex anions are more preferred.

［式（２ｃ）中、環Ｚ^７及び環Ｚ^８は、それぞれ独立に、置換基を有していてもよいベンゼン環又は置換基を有していてもよいナフタレン環を表す。
Ｙ^１〜Ｙ^５、ｕ、Ｘ^ｂ１−及びｂ１は、式（１ｂ）におけるものと同義である。
Ｙ^１０及びＹ^１１は、それぞれ独立に、置換基を有していてもよい炭素数１〜２０の１価の脂肪族炭化水素基を表す。
Ｙ^１２及びＹ^１３は、それぞれ独立に、水素原子、ハロゲン原子、又は、置換基を有していてもよい炭素数１〜６の１価の脂肪族炭化水素基を表すか、１個のＹ^１２と１個のＹ^１３とが互いに結合して炭素数２〜６の２価の脂肪族炭化水素基を表す。
ｐ１及びｐ２は、それぞれ独立に、０以上２以下の整数を表す。］ The compound represented by Formula (1 b) is preferably a compound represented by Formula (2 c).

[In Formula (2c), ring Z ⁷ and ring Z ⁸ each independently represent a benzene ring which may have a substituent or a naphthalene ring which may have a substituent.
^{Y 1 ~Y 5, u, X} b1- and b1 have the same meanings as those in formula (1b).
Y ¹⁰ and Y ¹¹ each independently represent a C 1 to C 20 monovalent aliphatic hydrocarbon group which may have a substituent.
Y ¹² and Y ¹³ each independently represent a hydrogen atom, a halogen atom, or a C 1-6 monovalent aliphatic hydrocarbon group which may have a substituent, or one Y ¹² and one Y ¹³ bond to each other to represent a divalent aliphatic hydrocarbon group having 2 to 6 carbon atoms.
p1 and p2 each independently represent an integer of 0 or more and 2 or less. ]

  Examples of monovalent aliphatic hydrocarbon groups include methyl, ethyl, vinyl, ethynyl, propyl, isopropyl, isopropenyl, allyl, propen-2-yl, propynyl, butyl and isobutyl Group, sec-butyl group, tert-butyl group, but-3-en-2-yl group, buta-1,3-dien-2-yl group, pentyl group, isopentyl group, neopentyl group, tert-pentyl group, 1 to 20 carbon atoms, such as 1-methylpentyl group, 2-methylpentyl group, penta-2-en-4-yl group, hexyl group, isohexyl group, 5-methylhexyl group, heptyl group and octyl group Aliphatic hydrocarbon groups of

As a substituent in a monovalent aliphatic hydrocarbon group, for example,
Aromatic hydrocarbon having 6 to 12 carbon atoms, such as phenyl group, o-tolyl group, m-tolyl group, p-tolyl group, xylyl group, mesityl group, o-cumenyl group, m-cumenyl group, p-cumenyl group and the like Group;
An alkoxy group having 1 to 8 carbon atoms, such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, phenoxy, benzyloxy and the like;
Halogen atoms such as fluorine atom, chlorine atom, bromine atom, iodine atom;
A hydroxy group; a carboxy group; a nitro group; a cyano group etc. are mentioned.

  Examples of the divalent aliphatic hydrocarbon group include a methylene group, an ethylene group, a propanediyl group and a butanediyl group.

Y ¹⁰ and Y ¹¹ are preferably each independently an alkyl group having 1 to 8 carbon atoms which may be substituted by a halogen atom, and an alkyl having 1 to 5 carbon atoms which may be substituted by a halogen atom More preferred is a group.
Y ¹² and Y ¹³ each independently represent an alkyl group having 1 to 3 carbon atoms are preferable optionally substituted by a halogen atom, more preferably a methyl group or a trifluoromethyl group. Y ¹² and Y ¹³ are preferably the same group.

Examples of the cyanine compound include compounds represented by Formula (2c-1) to compounds represented by Formula (2c-19).

  As a cation derived from a cyanine compound, the cation in the compound represented by the compound represented by Formula (1b) or Formula (2c) is mentioned.

As a salt with the anion derived from a xanthene compound and the cation derived from a cyanine compound, the salt as described in the following is mentioned.

  The content of the salt composed of the xanthene dye and the cyanine dye is usually 0.1 to 20 parts by mass with respect to 100 parts by mass of the compound (a).

<Dye (A2)>
The blue or purple dye means a dye having a maximum absorption wavelength in the range of 560 nm or more and 650 nm or less in a chloroform solution. The blue or violet dye is preferably a dye having a maximum absorption wavelength in the range of 580 nm to 650 nm, and more preferably a dye having a maximum absorption wavelength in the range of 600 nm to 645 nm.
The blue or purple dye (A2) is a dye represented by the triarylmethane dye (A4), the tetraazaporphyrin dye (A5), the anthraquinone dye (A6) and the formula (A7) (hereinafter referred to as dye (A7)) Preferably at least one selected from the group consisting of
More preferably, it is at least one selected from the group consisting of a triarylmethane dye (A4) and a dye (A7).
Two or more dyes (A2) may be contained.

The triarylmethane dye (A4) is a dye containing a compound having a triarylmethane skeleton in the molecule. Examples of triarylmethane dyes (A4) include
C. I. Acid Violet (hereinafter, the description of CI Acid Violet is omitted and only the number is described) 15, 16, 17, 19, 21, 23, 24, 25, 38, 49, 72,
C. I. Acid Blue 1, 3, 5, 7, 9, 11, 13, 15, 17, 22, 24, 26, 34, 38, 48, 75, 83, 84, 86, 88, 90, 90: 1, 91, 93, 93: 1, 99, 100, 103, 104, 108, 109, 110, 119, 123, 147, 213, 269,
C. I. Basic Blue 7, 81, 83, 88, 89,
C. I. Basic Violet 2,
C. I. Direct Blue 1, 3, 28, 29, 41, 42, 47, 52, 55,
C. I. Food violet 3,
C. I. Mordant violet 1, 1: 1, 3, 6, 8, 10, 11, 15, 16, 17, 18, 19, 21, 21, 23, 27, 28, 33, 36, 39, 49,
Etc.

Examples of the triarylmethane dye (A4) also include the compounds described below.

The tetraazaporphyrin dye (A5) is a dye containing a compound having a tetraazaporphyrin skeleton in the molecule. When the tetraazaporphyrin dye is an acid dye or a basic dye, it may form a salt with any cation or anion.
Examples of tetraazaporphyrin dyes include the compounds described below.

The anthraquinone dye (A6) is a dye containing a compound having an anthraquinone skeleton in the molecule.
As the anthraquinone dye (A6), for example,
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. Acid Violet 34,
C. I. Acid Blue 25, 27, 40, 45, 78, 80, 112
C. I. Disperse Violet 26, 27,
C. I. Disperse Blue 1, 14, 56, 60,
C. I. Direct Blue 40,
C. I. Mordant Blue 8
Etc.

The anthraquinone dye (A6) also includes the compounds described below.

［式（Ａ７）中、
ｇは、任意の自然数を表す。
Ｇ^ｇ−は、ｇ価のアニオンを表す。
Ｄは、置換基を有していてもよいヘテロ芳香族基を表す。
Ｒ^１Ａ、Ｒ^２Ａ、Ｒ^３Ａ、Ｒ^４Ａ、Ｒ^５Ａ、Ｒ^６Ａ、Ｒ^７Ａ及びＲ^８Ａは、それぞれ独立して、水素原子、ハロゲン原子、ニトロ基、ヒドロキシ基又はアルキル基を表し、該アルキル基に含まれる−ＣＨ_２−は、−Ｏ−に置き換わっていてもよい。
Ｒ^２１Ａ及びＲ^２２Ａは、それぞれ独立して、置換されていてもよいアミノ基を表す。］ As a dye (A7), the compound represented by a formula (A7) and its tautomer are mentioned.

[In the formula (A7),
g represents an arbitrary natural number.
G ^{g −} represents a g-valent anion.
D represents a heteroaromatic group which may have a substituent.
R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A and R ^8A each independently represent a hydrogen atom, a halogen atom, a nitro group, a hydroxy group or an alkyl group -CH ₂ contained in - may be replaced by -O-.
R ^21A and R ^22A each independently represent an amino group which may be substituted. ]

As an alkyl group represented by R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A and R ^8A , a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group Sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, 2-ethylhexyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, Cyclohexyl, methylcyclohexyl, dimethylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, decahydronaphthyl, adamantyl, 2-alkyladamantan-2-yl, 1- (adamantane-1-) Yl) alkane-1-yl group, norbornyl group, methylnor Alkyl group having 1 to 20 carbon atoms such as Runiru group and isobornyl group. Preferably it is a C1-C8 alkyl group, More preferably, it is a C1-C6 alkyl group, More preferably, it is a C1-C4 alkyl group.
-CH _2- contained in the alkyl group represented by R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A and R ^8A may be replaced by -O-.
Specific examples of the group in which —CH ₂ — contained in the alkyl group represented by R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A and R ^8A is replaced by —O— The following groups may be mentioned. Preferably, -CH _2- contained in the alkyl group having 1 to 10 carbons is a group substituted by -O-, and more preferably -CH _2- contained in the alkyl group having 1 to 6 carbons is- It is a group replacing O-.

Examples of the halogen atom represented by R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A and R ^8A include a fluorine atom, chlorine atom, bromine atom and iodine atom, preferably fluorine It is an atom or a chlorine atom.

R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A and R ^8A are each independently preferably a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, preferably a hydrogen atom or A methyl group is more preferable, and a hydrogen atom is more preferable.

The hydrogen atom contained in the amino group represented by R ^21A and R ^22A is an aryl group which may have a substituent, an alkyl group which may have a substituent, or an acryloyl group or a methacryloyl group. It may be substituted by the group which it contains.

  In the aryl group which may have a substituent, examples of the aryl group include aryl groups having a carbon number of 6 to 14, such as phenyl group, naphthyl group and anthracenyl group, which may be possessed by the aryl group As a substituent, a halogen atom and a C1-C8 alkyl group are mentioned.

In the alkyl group which may have a substituent, examples of the alkyl group include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, Hexyl group, heptyl group, 2-ethylhexyl group, octyl group, nonyl group, decyl group, undecyl group, dodecyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, methylcyclohexyl group, dimethylcyclohexyl group, cycloheptyl group , Cyclooctyl group, cyclononyl group, cyclodecyl group, decahydronaphthyl group, adamantyl group, 2-alkyladamantan-2-yl group, 1- (adamantan-1-yl) alkane-1-yl group, norbornyl group, methylnor Carbon number 1 such as bornyl and isobornyl They include alkyl groups of 20. Other -CH 2 _{- -} -CH 2 adjacent to a nitrogen atom contained in the alkyl group may be replaced by -O-, Examples of the substituent that the said alkyl group optionally having an amino group And substituted amino groups, groups containing a halogen atom and a silicon atom.
The halogen atom includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
As a substituted amino group, methylamino group, ethylamino group, propylamino group, isopropylamino group, butylamino group, sec-butylamino group, tert-butylamino group, dimethylamino group, diethylamino group, dipropylamino group, An alkylamino group having 1 to 8 carbon atoms such as an ethylmethylamino group and a dialkylamino group having 1 to 8 carbon atoms can be mentioned.

［式（Ａ７−１）中、Ｒ^１５Ａはアクリロイル基又はメタクリロイル基を表す。
Ｒ^１４Ａは、炭素数１〜８のアルカンジイル基を表し、該アルカンジイル基に含まれる−ＣＨ_２−は、−Ｏ−に置き換わっていてもよい。
＊は窒素原子との結合手を表す。］ The group containing an acryloyl group or a methacryloyl group means a group having at least one acryloyl group or a methacryloyl group as a constituent unit of the group.
The carbon number of the group containing an acryloyl group or a methacryloyl group is usually 3 to 30, and preferably 3 to 20.
The group containing an acryloyl group or a methacryloyl group is preferably a group containing an acryloyloxy group or a methacryloyloxy group.
The group containing an acryloyl group or a methacryloyl group is preferably a group represented by formula (A7-1).

[In Formula (A7-1), R ^15A represents an acryloyl group or a methacryloyl group.
R ^14A represents an alkanediyl group having 1 to 8 carbon atoms, and —CH ₂ — contained in the alkanediyl group may be replaced by —O—.
* Represents a bond with a nitrogen atom. ]

As a C1-C8 alkanediyl group represented by R ^14A , a methylene group, ethylene group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group Hexane-1,6-diyl group, heptane-1,7-diyl group, octane-1,8-diyl group, ethane-1,1-diyl group, propane-1,1-diyl group, propane-1, 2-diyl group, propane-2,2-diyl group, pentane-2,4-diyl group, 2-methylpropane-1,3-diyl group, 2-methylpropane-1,2-diyl group, pentane-1 And 2,4-diyl group and 2-methylbutane-1,4-diyl group, preferably alkanediyl group having 1 to 4 carbon atoms, more preferably methylene group or ethylene group, still more preferably methylene group It is.

  Examples of the group containing an acryloyl group or a methacryloyl group include the groups described below. (* Represents a bond with a nitrogen atom.)

The ^optionally substituted amino group represented by R ^21A and R ^22A is a methylamino group, an ethylamino group, a propylamino group, an isopropylamino group, a butylamino group, an isobutylamino group, a sec-butylamino group, tert-butylamino group, pentylamino group, neopentylamino group, hexylamino group, dimethylamino group, diethylamino group, diethylamino group, dipropylamino group, diisopropylamino group, ethylmethylamino group, ethylisopropylamino group, ethylpropylamino group, Isopropylmethylamino, isopropylpropylamino, methylpropylamino, phenylamino, naphthylamino, 2-methylphenylamino, 4-methylphenylamino, 3-methylphenylamino, 3,5-dimethylphenyl Mino group, 4-ethylphenylamino group, N-methyl-N-phenylamino group, acryloyloxymethylamino group, N- (acryloyloxymethyl) -N-methylamino group, N- (acryloyloxyethyl) -N- Ethylamino group, N- (methacryloyloxyethyl) -N-ethylamino group, N- (acryloyloxyethyl) -N-phenylamino group, N- (acryloyloxyethyl) -N- (methacryloyloxymethyl) amino group, Examples include N- (acryloyloxyethyloxymethyl) -N-ethylamino group and N- (methacryloyloxyethyloxymethyl) -N-ethylamino group.

The heteroaromatic hydrocarbon group represented by D may have at least one hetero atom, and the hetero atom includes a nitrogen atom, an oxygen atom and a sulfur atom.
The heteroaromatic hydrocarbon group represented by D may be monocyclic or polycyclic.
As the heteroaromatic hydrocarbon group represented by D, pyridyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, benzothiazolyl group, benzisothiazolyl group, thienyl group, benzothienyl group And a heteroaromatic hydrocarbon group having 2 to 8 carbon atoms, and a heteroaromatic hydrocarbon group having 2 to 8 carbon atoms containing at least one nitrogen atom or at least one sulfur atom as a ring constituent is preferable.
As a substituent which the hetero aromatic hydrocarbon group represented by D may have, it may have an amino group which may be substituted, an alkyl group having 1 to 20 carbon atoms, and a substituent. The aryl group is mentioned, The amino group which may be substituted and the aryl group which may have a substituent are preferable.

Examples of the amino group which may be substituted include the same as the amino group which may be substituted and which is represented by R ^21A and R ^22A .
The alkyl group having 1 to 20 carbon ^{atoms, R 1A, R 2A, R} 3A, R 4A, R 5A, R 6A, the same as the alkyl group having 1 to 20 carbon atoms represented by ^{R 7A} and ^{R 8A} It can be mentioned.
Examples of the aryl group which may have a substituent include phenyl group, naphthyl group and anthracenyl group, and examples of the substituent include halogen atoms such as fluorine atom, chlorine atom and bromine atom; An alkyl group is mentioned.

［式（ＩＩＩ）中、Ｘは、酸素原子又は硫黄原子を示す。
Ｒ^５５は、水素原子、炭素数１〜２０のアルキル基又は置換基を有していてもよいアリール基を表す。
Ｒ^５６は、置換されていてもよいアミノ基を表す。
＊は、炭素原子との結合手を表す。］ The heteroaromatic hydrocarbon group represented by D is preferably a group represented by Formula (III).

[In Formula (III), X shows an oxygen atom or a sulfur atom.
R ⁵⁵ represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or an aryl group which may have a substituent.
R ⁵⁶ represents an amino group which may be substituted.
* Represents a bond with a carbon atom. ]

Examples of the alkyl group having 1 to 20 carbon atoms represented by R ⁵⁵ include C ¹ to 20 carbon atoms represented by R ^1A , R ^2A , R ^3A , R ^4A , R ^5A , R ^6A , R ^7A and R ^8A The same thing as an alkyl group is mentioned.
^Examples of the optionally substituted aryl group represented by R ⁵⁵ include a phenyl group.
^Examples of the optionally substituted amino group represented by R ⁵⁶ include the same as the ^optionally substituted amino group represented by R ^21A and R ^22A .

R ⁵⁵ is preferably an unsubstituted or substituted aryl group, more preferably an unsubstituted or substituted by a halogen atom.
R ⁵⁶ is preferably an amino group which may be substituted.

Examples of the heteroaromatic hydrocarbon group represented by D include a group represented by formula (III-1) to a group represented by formula (III-8), and preferably a group represented by formula (III-1) or It is a group represented by formula (III-2).

［式（ｙ１）において、Ｒ^Ｂ１は、ハロゲン原子を有していてもよい炭化水素基を表す。
式（ｙ２）において、Ｒ^Ｂ２及びＲ^Ｂ３は、それぞれ独立して、ハロゲン原子又はハロゲン化炭化水素基を表すか、又はＲ^Ｂ２とＲ^Ｂ３とが互いに結合して−ＳＯ_２−Ｎ⁻−ＳＯ_２−を含む環を形成する。
式（ｙ３）において、Ｍはアルミニウム原子又はホウ素原子を表し、Ｒ^Ｂ４及びＲ^Ｂ５は、それぞれ独立に、置換基を有していてもよいフェニル基を表す。］ g is an arbitrary natural number, preferably a natural number of 1 to 2, more preferably 1.
G ^{g −} represents a g-valent anion, and is not limited as long as it forms a salt with a cation and a g-valent anion. For example, when g is a natural number of 2 or more, it may have one g-valent anion or may have g monovalent anions or g monovalent anion sites.
G ^{g −} is preferably a monovalent anion, and examples thereof include halide ions such as fluoride ion, chloride ion, bromide ion and iodide ion, anions represented by formula (y1), formula (y2) And anions represented by formula (y3).

[In formula (y1), R ^B1 represents a hydrocarbon group which may have a halogen atom.
In formula (y2), R ^B2 and R ^B3 each independently represent a halogen atom or a halogenated hydrocarbon group, or R ^B2 and R ^B3 are bonded to each other to form —SO ₂ —N ^— —SO _It forms a ring containing _2- .
In formula (y3), M represents an aluminum atom or a boron atom, and R ^B4 and R ^B5 each independently represent a phenyl group which may have a substituent. ]

The hydrocarbon group represented by R ^B1, include alkyl groups and aromatic hydrocarbon group having 6 to 14 carbon atoms having 1 to 8 carbon atoms.
As the alkyl group having 1 to 8 carbon atoms, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, heptyl group, 2 -Ethylhexyl group, octyl group, cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, methylcyclohexyl group can be mentioned.
As a C6-C14 aromatic hydrocarbon group, a phenyl group and a naphthyl group are mentioned.
The halogen atom includes a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, preferably a fluorine atom.
As the halogenated alkyl group having 1 to 8 carbon atoms, a difluoromethyl group, a trifluoromethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a perfluoro Ethyl group, 1,1,2,2-tetrafluoropropyl group, 1,1,2,2,3,3-hexafluoropropyl group, perfluoroethyl methyl group, 1- (trifluoromethyl) -1,2, 2,2-tetrafluoroethyl group, perfluoropropyl group, 1,1,2,2-tetrafluorobutyl group, 1,1,2,2,3,3-hexafluorobutyl group, 1,1,2,2 And a 3,3,4,4-octafluorobutyl group, a perfluorobutyl group, a dibromomethyl group and a tribromomethyl group, preferably a fluorinated alkyl group having 1 to 8 carbon atoms. That.
As an aromatic hydrocarbon group which has a C6-C14 halogen atom, the phenyl group which has a halogen atom, and the naphthyl group which has a halogen atom are mentioned. Specifically, fluorophenyl group, chlorophenyl group, bromophenyl group, difluorophenyl group, 1-fluoro-4-chlorophenyl group, trifluorophenyl group, fluoronaphthyl group may be mentioned.

R ^B1 is preferably a halogenated alkyl group having 1 to 8 carbon atoms, and more preferably a fluorinated alkyl group having 1 to 8 carbon atoms.

As a halogen atom represented by ^RB2 and ^RB3 , a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom are mentioned, Preferably it is a fluorine atom or a chlorine atom.
Examples of the halogenated hydrocarbon group represented by R ^B2 and R ^B3, and an aromatic hydrocarbon group having 6 to 14 carbon atoms having a halogenated alkyl group having 1 to 8 carbon atoms, a halogen atom.
As the halogenated alkyl group having 1 to 8 carbon atoms, a difluoromethyl group, a trifluoromethyl group, a 1,1-difluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a perfluoro Ethyl group, 1,1,2,2-tetrafluoropropyl group, 1,1,2,2,3,3-hexafluoropropyl group, perfluoroethyl methyl group, 1- (trifluoromethyl) -1,2, 2,2-tetrafluoroethyl group, perfluoropropyl group, 1,1,2,2-tetrafluorobutyl group, 1,1,2,2,3,3-hexafluorobutyl group, 1,1,2,2 And a 3,3,4,4-octafluorobutyl group, a perfluorobutyl group, a dibromomethyl group and a tribromomethyl group, preferably a fluorinated alkyl group having 1 to 8 carbon atoms. That.
As an aromatic hydrocarbon group which has a C6-C14 halogen atom, the phenyl group which has a halogen atom, and the naphthyl group which has a halogen atom are mentioned. Specifically, fluorophenyl group, chlorophenyl group, bromophenyl group, difluorophenyl group, 1-fluoro-4-chlorophenyl group, trifluorophenyl group, fluoronaphthyl group may be mentioned.

Preferably, R ^B2 and R ^B3 are the same group.
Each of R ^B2 and R ^B3 is preferably independently a fluorinated alkyl group having 1 to 8 carbon atoms, and more preferably a trifluoromethyl group.

As a substituent which the phenyl group represented by R ^B4 and R ^B5 may have, a hydroxyl group is preferable.
Preferably, R ^B4 and R ^B5 are the same group.

  As the anion represented by the formula (y1), methanesulfonic acid anion, toluenesulfonic acid anion, dodecylbenzenesulfonic acid anion, trifluoromethanesulfonic acid anion, perfluorobutanesulfonic acid anion, phenylsulfonic acid anion, fluorophenylsulfonic acid anion Etc.

As an anion represented by Formula (y2), the anion as described in the following is mentioned.

As an anion represented by Formula (y3), the anion as described in the following is mentioned.

Examples of the dye (A7) include compounds represented by formulas (A-I-a1) to (A-I-a15). Compounds represented by the formula (A-I-a5) to compounds represented by the formula (A-I-a12) are preferable.

  The dye (A7) can be produced, for example, by the method described in Korean Patent Publication No. 2014-0026284.

The blue or purple dye may be monomeric or polymeric. The polymer which is a blue or purple dye is a polymer containing a structural unit derived from a blue or purple dye, and may be a polymer consisting only of structural units derived from a blue or purple dye, or a blue or purple dye The copolymer may be a copolymer containing a structural unit derived therefrom and another structural unit (hereinafter sometimes referred to as “copolymer (a)”). The structural unit derived from the blue or violet dye may be a divalent or higher group generated by polymerization of the polymerizable blue or violet dye, or may be one or more hydrogen atoms removed from the blue or violet dye. It may be a monovalent or more group. As the copolymer (a), a structural unit derived from a monomer having an ethylenically unsaturated bond in addition to a structural unit derived from a blue or violet dye, and a formula (1) to (6) described below The copolymer containing at least 1 chosen from the group which consists of a structural unit represented by 3) is mentioned.
Further, the copolymer (a) may be a copolymer including a structural unit derived from a monomer leading to a resin (B) described later and a structural unit derived from a blue or purple dye.

［式（１）中、Ｒ^９及びＲ^１０は、それぞれ独立して、水素原子、置換基を有していてもよい炭素数１〜３０のアルキル基、置換基を有していてもよい炭素数６〜３０のアリール基、置換基を有していてもよいアルキルアリール基又はこれらの組み合わせを表す。
ｍ’は、０〜５の整数を表す。］

[In formula (1), R ⁹ and R ¹⁰ each independently represent a hydrogen atom, an alkyl group having 1 to 30 carbon atoms which may have a substituent, or carbon which may have a substituent] It represents an aryl group of several 6 to 30, an alkylaryl group which may have a substituent, or a combination thereof.
m 'represents an integer of 0 to 5; ]

［式（２）中、Ｒ^１１は、水素原子、置換基を有していてもよい炭素数１〜３０のアルキル基、置換基を有していてもよい炭素数６〜３０のアリール基、置換基を有していてもよいアルキルアリール基又はこれらの組み合わせを表す。
Ｒ^１２は、置換基を有していてもよい炭素数１〜３０のアルキル基、置換基を有していてもよい炭素数６〜３０のアリール基、−ＣＯ−Ｒ^１７−ＣＯＯＨ又はこれらの組み合わせを表す。
Ｒ^１７は、置換基を有していてもよい炭素数１〜３０のアルキレン基又は置換基を有していてもよい炭素数１〜３０のアルコキシレン基を表す。］

[In Formula (2), R ¹¹ represents a hydrogen atom, an alkyl group having 1 to 30 carbon atoms which may have a substituent, an aryl group having 6 to 30 carbon atoms which may have a substituent, It represents an alkylaryl group which may have a substituent or a combination thereof.
R ¹² is an alkyl group having 1 to 30 carbon atoms which may have a substituent, an aryl group having 6 to 30 carbon atoms which may have a substituent, -CO-R ¹⁷ -COOH, or a group thereof Represents a combination.
R ¹⁷ represents an alkylene group having 1 to 30 carbon atoms which may have a substituent, or an alkoxyl group having 1 to 30 carbon atoms which may have a substituent. ]

［式（３）中、Ｒ^１３及びＲ^１４は、それぞれ独立して、水素原子、置換基を有していてもよい炭素数１〜３０のアルキル基、置換基を有していてもよい炭素数６〜３０のアリール基、置換基を有していてもよいアルキルアリール基又はこれらの組み合わせを表す。
Ｒ^１５は、−ＣＯＯＨ又は−ＣＯＮＨＲ^１８を表す。
Ｒ^１８は、置換基を有していてもよい炭素数１〜３０のアルキル基又は置換基を有していてもよい炭素数６〜３０のアリール基を表す。
Ｒ^１６は、−ＣＯＯＨを表し、Ｒ^１５及びＲ^１６は、互いに結合して環を形成する。］

[In formula (3), R ¹³ and R ¹⁴ each independently represent a hydrogen atom, an alkyl group having 1 to 30 carbon atoms which may have a substituent, or carbon which may have a substituent It represents an aryl group of several 6 to 30, an alkylaryl group which may have a substituent, or a combination thereof.
R ¹⁵ represents -COOH or -CONHR ^18.
R ¹⁸ represents an alkyl group having 1 to 30 carbon atoms which may have a substituent or an aryl group having 6 to 30 carbon atoms which may have a substituent.
R ¹⁶ represents —COOH, and R ¹⁵ and R ¹⁶ combine with each other to form a ring. ]

The monomer having an ethylenically unsaturated bond is an ethylenically unsaturated monomer containing one or more carboxy groups, and specifically, acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid Can be mentioned.
The weight ratio of monomers having an ethylenically unsaturated bond is usually 1 to 50% by weight, preferably 3 to 40% by weight, based on the total weight of monomers forming the copolymer (a) More preferably, it is 5 to 30% by weight.

Further, it may contain a structural unit derived from a monomer having an ethylenically unsaturated bond and a structural unit derived from a copolymerizable monomer, specifically,
Alkenyl aromatic monomers such as styrene, α-methylstyrene, vinyl toluene, vinyl benzyl methyl ether;
Methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, butyl acrylate, butyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 2-hydroxybutyl acrylate, 2-hydroxybutyl methacrylate, benzyl acrylate, benzyl methacrylate, cyclohexyl acrylate And unsaturated carboxylic acid esters such as cyclohexyl methacrylate, phenyl acrylate, phenyl methacrylate and the like;
Unsaturated carboxylic acid aminoalkyl esters such as 2-aminoethyl acrylate, 2-aminoethyl methacrylate, 2-dimethylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate and the like;
Carboxylic acid vinyl esters such as vinyl acetate and vinyl benzoate;
Unsaturated carboxylic acid glycidyl esters such as glycidyl acrylate and glycidyl methacrylate;
Vinyl cyanide compounds such as acrylonitrile and methacrylonitrile;
And unsaturated amide compounds such as acrylamide and methacrylamide, and combinations thereof.

The structural unit derived from the blue or purple dye contained in the copolymer (a) is a structural unit derived from the triarylmethane dye (A4) and a structural unit derived from the dye represented by the formula (A7) It is preferably at least one selected from the group consisting of
As a structural unit derived from the triarylmethane dye (A4), the respective structures derived from the compound represented by the formula (2b-1) described above to the compound represented by the formula (2b-13) Units are preferred.
As a structural unit derived from the dye represented by Formula (A7), a structural unit derived from the compound represented by Formula (A-I-a15) described above is preferable.

In addition, the blue or violet dye and the compound (a) may form a salt. As a salt which consists of a blue or purple dye and a compound (a), the salt which consists of the cation derived from a blue or purple dye, and the anion derived from a compound (a) is mentioned.
As a salt which consists of a blue or a purple dye and a compound (a), the thing as described in the following is mentioned, for example.

  The content of the dye (A2) is usually 80 to 10000 parts by mass, preferably 80 to 7000 parts by mass, more preferably 80 to 1000 parts by mass, per 100 parts by mass of the xanthene dye. Preferably it is 80-600 mass parts.

<Dye (Ac) and Pigment (A1)>
The dye (Ac) is not particularly limited, and known dyes can be used.
The pigment (A1) is not particularly limited and known pigments can be used, and examples thereof include pigments classified into pigments by Color Index (published by The Society of Dyers and Colourists).
As a pigment, C.I. I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60, etc. Blue pigments:
C. I. And violet pigments such as CI pigment violet 1, 19, 23, 29, 32, 36, 38 and the like.

The colorant (A) is preferably a colorant containing the combination described below.
(1) Compound (a), C.I. I. Acid Red 52 and Blue or Purple Dye (A2)
(2) Compound (a), C.I. I. Acid red 52, blue or purple dye (A2) and blue pigment (3) compound (a), C.I. I. Acid red 52, blue or violet dye (A2) and violet pigment (4) compound (a), C.I. I. Acid red 52, blue or purple dye (A2), blue pigment and purple pigment

The content of the coloring agent (A) is preferably 5 to 60% by mass, more preferably 8 to 55% by mass, and still more preferably 10 to 50% by mass, with respect to the total amount of solids.
When the content of the coloring agent (A) is in the above range, the color density when forming a color filter is sufficient, and the necessary amount of the resin (B) or the polymerizable compound (C) is contained in the composition. As a result, it is possible to form a pattern with sufficient mechanical strength. Here, "the total amount of solid content" in the present specification means an amount obtained by removing the content of the solvent from the total amount of the colored curable resin composition. The total amount of solids and the content of each component relative thereto can be measured, for example, by known analytical means such as liquid chromatography or gas chromatography.

<Resin (B)>
Although resin (B) is not specifically limited, It is preferable that it is alkali-soluble resin. As resin (B), the following resin [K1]-[K6] etc. are mentioned.
Resin [K1] unsaturated carboxylic acid and at least one selected from the group consisting of unsaturated carboxylic acid anhydrides (hereinafter sometimes referred to as "(a)"), cyclic ether structure having 2 to 4 carbon atoms And a copolymer of a monomer (b) (hereinafter sometimes referred to as "(b)") having an ethylenic unsaturated bond;
Resin [K2] (a), (b), and (a) a monomer (c) (but different from (a) and (b)) copolymerizable (hereinafter referred to as "(c)" May be copolymer with);
Copolymers of resins [K3] (a) and (c);
Resin obtained by reacting (b) with a copolymer of resin [K4] (a) and (c);
Resin obtained by reacting (a) with a copolymer of resin [K5] (b) and (c);
Resin obtained by reacting (a) with a copolymer of resin [K6] (b) and (c) and further reacting with a carboxylic anhydride.

Specific 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, 5-carboxy-5-methylbicyclo [2.2.1] hept-2-ene, 5-carboxy-5-ethylbicyclo [2.2.1] hept-2-ene, 5-carboxy-6-methylbicyclo [2.2.1] Bicyclo unsaturated compounds containing a carboxy group such as hept-2-ene and 5-carboxy-6-ethylbicyclo [2.2.1] hept-2-ene;
Maleic anhydride, citraconic anhydride, itaconic anhydride, 3-vinylphthalic anhydride, 4-vinylphthalic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, 1,2,3,6- Unsaturated dicarboxylic acid anhydrides such as tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride;
Unsaturated mono [(meth) acryloyloxyalkyl] ester of a polyvalent carboxylic acid having a valence of 2 or more such as mono [2- (meth) acryloyloxyethyl] succinate, mono [2- (meth) acryloyloxyethyl] phthalate, etc. Kind;
Examples thereof 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 preferable from the viewpoint of copolymerization reactivity and the solubility of the obtained resin in an aqueous alkali solution.

(B) is, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (eg, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond Say. (B) is preferably a monomer having a cyclic ether having 2 to 4 carbon atoms and a (meth) acryloyloxy group.
In the present specification, “(meth) acrylic acid” represents at least one selected from the group consisting of acrylic acid and methacrylic acid. The notations such as "(meth) acryloyl" and "(meth) acrylate" have the same meaning.

  Examples of (b) include a monomer (a1) having an oxiranyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b1)”), a single monomer having an oxetanyl group and an ethylenically unsaturated bond. A monomer (b2) (hereinafter sometimes referred to as "(b2)"), a monomer (b3) (hereinafter sometimes referred to as "(b3)") having a tetrahydrofuryl group and an ethylenically unsaturated bond, etc. It can be mentioned.

  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 monomers (b1-2) having a structure in which an alicyclic unsaturated hydrocarbon is epoxidized (hereinafter sometimes referred to as "(b1-2)").

  As (b1-1), glycidyl (meth) acrylate, β-methyl glycidyl (meth) acrylate, β-ethyl glycidyl (meth) acrylate, glycidyl vinyl ether, o-vinyl benzyl glycidyl ether, m-vinyl benzyl glycidyl ether, p -Vinyl benzyl glycidyl ether, α-methyl-o-vinyl benzyl glycidyl ether, α-methyl-m-vinyl benzyl glycidyl ether, α-methyl-p-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 (glycidyloxymethyl) styrene and the like can be mentioned.

  Examples of (b1-2) include vinylcyclohexene monoxide, 1,2-epoxy-4-vinylcyclohexane (eg, Celoxide 2000; manufactured by Daicel Corporation), 3,4-epoxycyclohexylmethyl (meth) acrylate (eg, Cyclomer A400; manufactured by Daicel Co., Ltd., 3,4-epoxycyclohexylmethyl (meth) acrylate (for example, Cyclomer M100; manufactured by Daicel Co., Ltd.), a compound represented by Formula (I), and Formula (II) And the like.

[In Formula (I) and Formula (II), R ^a and R ^b represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, and the hydrogen atom contained in the alkyl group is substituted with a hydroxy group May be
X ^a and ^{X b} is a single ^{bond, -R c -, * - R} c -O -, * - represents the R c -S- or ^* -R c -NH-.
R ^c represents an alkanediyl group having 1 to 6 carbon atoms.
* Represents a bond with O. ]

As a C1-C4 alkyl group, a methyl group, an ethyl group, n-propyl group, isopropyl group, n-butyl group, a sec-butyl group, a tert- butyl group etc. are mentioned.
As an alkyl group in which a hydrogen atom is substituted by hydroxy, a hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group, 1-hydroxy group Examples include -1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, 4-hydroxybutyl group and the like.
As ^Ra and ^Rb , Preferably a hydrogen atom, a methyl group, a hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group is mentioned, More preferably, a hydrogen atom and a methyl group are mentioned.

As an alkanediyl group, a methylene group, ethylene group, propane-1,2-diyl group, propane-1,3-diyl group, butane-1,4-diyl group, pentane-1,5-diyl group, hexane- 1,6-diyl group etc. are mentioned.
Preferred examples of X ^a and X ^b include ^a single bond, a methylene group, an ethylene group, * -CH ₂ -O- and * -CH ₂ CH ₂ -O-, and more 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 (I) include a compound represented by the formula (I-1) to a compound represented by the formula (I-15). Preferably, the compound represented by the formula (I-1), the compound represented by the formula (I-3), the compound represented by the formula (I-5), the compound represented by the formula (I-7), Examples thereof include a compound represented by the formula (I-9) or a compound represented by the formula (I-11) to a compound represented by the formula (I-15). More preferably, the compound represented by the formula (I-1), the compound represented by the formula (I-7), the compound represented by the formula (I-9) or the compound represented by the formula (I-15) Can be mentioned.

  Examples of the compound represented by the formula (II) include a compound represented by the formula (II-1) to a compound represented by the formula (II-15). Preferably, the compound represented by the formula (II-1), the compound represented by the formula (II-3), the compound represented by the formula (II-5), the compound represented by the formula (II-7), Examples thereof include a compound represented by the formula (II-9) or a compound represented by the formula (II-11) to a compound represented by the formula (II-15). More preferably, a compound represented by Formula (II-1), a compound represented by Formula (II-7), a compound represented by Formula (II-9) or Formula (II-15) can be mentioned.

  The compound represented by Formula (I) and the compound represented by Formula (II) can be used independently, respectively. Also, they can be mixed in any ratio. When mixing, the mixing ratio is preferably 5:95 to 95: 5, more preferably 10:90 to 90:10, still more preferably 20:80 in terms of a molar ratio of formula (I): formula (II). -80: 20.

  As (b2), a monomer having an oxetanyl group and a (meth) acryloyloxy group is more preferable. As (b2), 3-methyl-3-methacryloyloxymethyl oxetane, 3-methyl-3-acryloyloxymethyl oxetane, 3-ethyl-3-methacryloyloxymethyl oxetane, 3-ethyl-3-acryloyloxymethyl oxetane 3-methyl-3-methacryloyloxyethyl oxetane, 3-methyl-3-acryloyloxyethyl oxetane, 3-ethyl-3-methacryloyloxyethyl oxetane, 3-ethyl-3-acryloyloxyethyl oxetane and the like.

  As (b3), a monomer having a tetrahydrofuryl group and a (meth) acryloyloxy group is more preferable. Specific examples of (b3) include tetrahydrofurfuryl acrylate (for example, Biscoat V # 150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate and the like.

  As (b), (b1) is preferable in that the reliability such as heat resistance and chemical resistance of the color filter to be obtained can be further enhanced. Furthermore, (b1-2) is more preferable in that the storage stability of the colored curable resin composition is excellent.

Examples of (c) include methyl (meth) acrylate, ethyl (meth) acrylate, n-butyl (meth) acrylate, sec-butyl (meth) acrylate, tert-butyl (meth) acrylate and 2-ethylhexyl (meth) Acrylate, dodecyl (meth) acrylate, lauryl (meth) acrylate, stearyl (meth) acrylate, cyclopentyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decane-8-yl (meth) acrylate (in the art, it is commonly referred to as "dicyclopentanyl (meth) acrylate". Also, in the case of "tricyclodecyl (meth) acrylate") There is a) Black (in the art, it is said that "dicyclopentenyl (meth) acrylate" as trivial name.) [5.2.1.0 ^2,6] decene-8-yl (meth) acrylate, dicyclopenta Nyloxyethyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate, benzyl (meth) acrylate, etc. (Meth) acrylic esters;
Hydroxy group-containing (meth) acrylic acid esters such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate;
Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, 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 [2.2.1] hept-2-ene, 5-hydroxymethyl-5-methylbicyclo [2.2.1] hept-2-ene, 5-tert-butoxycarbonylbicyclo [4] 2.2.1] Hept-2-ene, 5-cyclohexyloxycarbonylbicyclo [2.2.1] hept-2-ene, 5-phenoxycarbonylbicyclo [2.2.1] hept-2-ene, 5 6,6-bis (tert-butoxycarbonyl) bicyclo [2.2.1] hept-2-ene, 5,6-bis (cyclohexyloxycarbonyl) bicyclo [2.2.1] hept-2-ene, etc. Bicyclo unsaturated compounds;
N-phenyl maleimide, N-cyclohexyl maleimide, N-benzyl maleimide, N-succinimidyl-3-maleimidobenzoate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3 -Dicarbonylimide derivatives such as maleimide propionate, N- (9-acridinyl) maleimide and the like;
Styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyl toluene, p-methoxystyrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinylidene chloride, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene , Isoprene, 2,3-dimethyl-1,3-butadiene and the like.
Among them, styrene, vinyl toluene, N-phenyl maleimide, N-cyclohexyl maleimide, N-benzyl maleimide, bicyclo [2.2.1] hept-2-ene and the like from the viewpoint of copolymerization reactivity and heat resistance. preferable.

In the resin [K1], the ratio of structural units derived from each of them is the total structural unit constituting the resin [K1],
Structural unit derived from (a); 2 to 60 mol%
Structural unit derived from (b); 40 to 98 mol%
Is preferably
Structural unit derived from (a); 10 to 50 mol%
Structural unit derived from (b); 50 to 90 mol%
It is more preferable that
When the ratio of structural units of the resin [K1] is in the above range, the storage stability of the colored curable resin composition, the developability when forming a colored pattern, and the solvent resistance of the obtained color filter are excellent. Tend.

  Resin [K1] can be prepared, for example, by the method described in the literature "Experimental method of polymer synthesis" (by Takayuki Otsu, Publisher, Chemical Co., Ltd., First Edition, First Edition, published on March 1, 1972) It can be manufactured with reference to the cited documents described in.

  Specifically, a predetermined amount of (a) and (b), a polymerization initiator, a solvent and the like are placed in a reaction vessel, and for example, oxygen is replaced by nitrogen to make an oxygen scavenging atmosphere, while stirring. The method of heating and heat retention is mentioned. In addition, the polymerization initiator, the solvent, etc. used here are not specifically limited, What is usually used in the said field | area can be used. For example, as a polymerization initiator, an azo compound (2,2'-azobisisobutyronitrile, 2,2'-azobis (2,4-dimethyl valeronitrile), etc.) or an organic peroxide (benzoyl peroxide, etc.) As the solvent, any solvent can be used as long as it dissolves each monomer, and the solvent described later as the solvent (E) of the colored curable resin composition of the present invention can be mentioned.

  In addition, the obtained copolymer may use the solution after reaction as it is, may use a concentrated or diluted solution, or is taken out as a solid (powder) by a method such as reprecipitation. You may use one. In particular, by using the solvent contained in the colored photosensitive resin composition of the present invention as a solvent in the polymerization, the solution after reaction is used as it is for the preparation of the colored photosensitive resin composition of the present invention As a result, the process for producing the colored photosensitive resin composition of the present invention can be simplified.

In the resin [K2], the ratio of structural units derived from each of them is the total structural unit constituting the resin [K2],
Structural unit derived from (a); 2 to 45 mol%
Structural unit derived from (b); 2 to 95 mol%
Structural unit derived from (c); 1 to 65 mol%
Is preferably
Structural unit derived from (a); 5 to 40 mol%
Structural unit derived from (b); 5 to 80 mol%
Structural unit derived from (c); 5 to 60 mol%
It is more preferable that
When the ratio of structural units of the resin [K2] is in the above range, the storage stability of the colored curable resin composition, the developability when forming a colored pattern, and the solvent resistance of the obtained color filter, It tends to be excellent in heat resistance and mechanical strength.

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

In the resin [K3], the ratio of structural units derived from each of them is the total structural unit constituting the resin [K3],
Structural unit derived from (a); 2 to 60 mol%
Structural unit derived from (c); 40 to 98 mol%
Is preferably
Structural unit derived from (a); 10 to 50 mol%
Structural unit derived from (c); 50 to 90 mol%
It is more preferable that
The resin [K3] can be produced, for example, in the same manner as the method described for producing the resin [K1].

Resin [K4] obtains a copolymer of (a) and (c), and the carboxylic acid and / or carboxylic anhydride which (a) has a C2-C4 cyclic ether possessed by (b) It can be manufactured by adding it to
First, a copolymer of (a) and (c) is produced in the same manner as the method described for producing the resin [K1]. In this case, it is preferable that the ratio of the structural unit derived from each is the same ratio as what was mentioned by resin [K3].

Next, a portion of the carboxylic acid and / or carboxylic anhydride derived from (a) in the copolymer is reacted with the cyclic ether having 2 to 4 carbon atoms which (b) has.
Subsequently to the production of the copolymer of (a) and (c), the atmosphere in the flask is replaced with air from nitrogen, and (b) a reaction catalyst of carboxylic acid or carboxylic acid anhydride with cyclic ether (for example, tris ( A resin [K4] may be produced by placing dimethylaminomethyl) phenol etc.) and a polymerization inhibitor (eg hydroquinone etc.) etc. in a flask and reacting at 60 to 130 ° C. for 1 to 10 hours, for example. it can.
The amount of (b) to be used is preferably 5 to 80 mol, more preferably 10 to 75 mol, per 100 mol of (a). By setting it in this range, the storage stability of the colored curable resin composition, the developability in forming a pattern, and the balance between solvent resistance, heat resistance, mechanical strength and sensitivity of the obtained pattern become good. Tend. Since the reactivity of the cyclic ether is high and unreacted (b) is unlikely to remain, as (b) used for the resin [K4], (b1) is preferable, and (b1-1) is more preferable.
The amount of the reaction catalyst used is preferably 0.001 to 5 parts by mass with respect to 100 parts by mass of the total amount of (a), (b) and (c). The amount of the polymerization inhibitor used is preferably 0.001 to 5 parts by mass with respect to 100 parts by mass of the total amount of (a), (b) and (c).
The reaction conditions such as the charging method, reaction temperature and time can be appropriately adjusted in consideration of the production equipment and the amount of heat generated by polymerization. As with the polymerization conditions, the charging method and the reaction temperature can be appropriately adjusted in consideration of the production equipment and the calorific value due to the polymerization.

Resin [K5] obtains a copolymer of (b) and (c) as the first step in the same manner as the method for producing resin [K1] described above. Similarly to the above, the obtained copolymer may use the solution after reaction as it is, may use a concentrated or diluted solution, or may be solid (powder) by a method such as reprecipitation. You may use what was taken out.
The proportions of structural units derived from (b) and (c) are each relative to the total number of moles of all structural units that constitute the copolymer described above.
Structural unit derived from (b); 5 to 95 mol%
Structural unit derived from (c); 5 to 95 mol%
Is preferably
Structural unit derived from (b); 10 to 90 mol%
Structural unit derived from (c); 10 to 90 mol%
It is more preferable that

Furthermore, under the same conditions as in the method for producing the resin [K4], the carboxylic acid or carboxylic anhydride which (a) has in the cyclic ether derived from (b) which the copolymer of (b) and (c) has By reacting the product, a resin [K5] can be obtained.
As for the usage-amount of (a) made to react with said copolymer, 5-80 mol is preferable with respect to 100 mol of (b). Because the reactivity of the cyclic ether is high and unreacted (b) is unlikely to remain, as (b) used for the resin [K5], (b1) is preferable, and (b1-1) is more preferable.

The resin [K6] is a resin obtained by further reacting a carboxylic anhydride with the resin [K5]. The carboxylic acid anhydride is reacted with the hydroxy group generated by the reaction of the cyclic ether and the carboxylic acid or carboxylic acid anhydride.
As the carboxylic acid anhydride, maleic anhydride, citraconic acid anhydride, itaconic acid anhydride, 3-vinylphthalic acid anhydride, 4-vinylphthalic acid anhydride, 3,4,5,6-tetrahydrophthalic acid anhydride, 1 And 2,3,6-tetrahydrophthalic anhydride, dimethyltetrahydrophthalic anhydride, 5,6-dicarboxybicyclo [2.2.1] hept-2-ene anhydride (hemic anhydride), etc. Be The amount of use of the carboxylic acid anhydride is preferably 0.5 to 1 mole with respect to 1 mole of the amount of (a) used.

As the resin (B), specifically, 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2.6 Resin [K1] such as decyl acrylate / (meth) acrylic acid copolymer; glycidyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer, glycidyl (meth) acrylate / styrene / (meth) ) Acrylic acid copolymer, 3,4-epoxytricyclo [5.2.1.0 ^2.6 ] decyl acrylate / (meth) acrylic acid / N-cyclohexyl maleimide copolymer, 3-methyl-3- (3) Resin [K2] such as (meth) acryloyloxymethyl oxetane / (meth) acrylic acid / styrene copolymer; benzyl (meth) acrylate / Resin [K3] such as (meth) acrylic acid copolymer, styrene / (meth) acrylic acid copolymer; glycidyl (meth) acrylate added to benzyl (meth) acrylate / (meth) acrylic acid copolymer Resin, resin obtained by adding glycidyl (meth) acrylate to tricyclodecyl (meth) acrylate / styrene / (meth) acrylic acid copolymer, tricyclodecyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic Resin [K4] such as resin obtained by adding glycidyl (meth) acrylate to acid copolymer; resin obtained by reacting (meth) acrylic acid with tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate copolymer , Tricyclodecyl (meth) acrylate / styrene / glycidyl (meth) acrylate Resin [K5] such as resin obtained by reacting (meth) acrylic acid with copolymer; copolymer obtained by reacting (meth) acrylic acid with tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate copolymer Furthermore, resin [K6] etc., such as resin with which tetrahydrophthalic anhydride was made to react, etc. are mentioned.
Among them, as the resin (B), the resin [K1] and the resin [K2] are preferable.

The polystyrene equivalent weight average molecular weight of the resin (B) is preferably 3,000 to 100,000, more preferably 5,000 to 50,000, and still more preferably 5,000 to 30,000. . When the molecular weight is in the above range, the coating film hardness is improved, the residual film ratio is high, the solubility of the unexposed area in the developer 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 1.1 to 6, and more preferably 1.2 to 4.

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

  The content of the resin (B) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and still more preferably 17 to 55% by mass, with respect to the total amount of solids.

<Polymerizable compound (C)>
The polymerizable compound (C) is a compound which 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 ethylenic unsaturated bond, and the like Is a (meth) acrylic acid ester compound.

Among them, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenic unsaturated bonds. As such a polymerizable compound, for example, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa ( Meta) acrylate, tripentaerythritol octa (meth) acrylate, tripentaerythritol hepta (meth) acrylate, tetrapentaerythritol deca (meth) acrylate, tetrapentaerythritol nona (meth) acrylate, tris (2- (meth) acryloyloxyethyl) ) Isocyanurate, ethylene glycol modified pentaerythritol tetra (meth) acrylate, ethylene glycol modified dipentaerythritol Hexa (meth) acrylate, propylene glycol modified pentaerythritol tetra (meth) acrylate, propylene glycol modified dipentaerythritol hexa (meth) acrylate, caprolactone modified pentaerythritol tetra (meth) acrylate, caprolactone modified dipentaerythritol hexa (meth) acrylate, etc. Can be mentioned.
Among them, dipentaerythritol penta (meth) acrylate and dipentaerythritol hexa (meth) acrylate are preferable.

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

  The content of the polymerizable compound (C) is preferably 7 to 65% by mass, more preferably 13 to 60% by mass, and still more preferably 17 to 55% by mass, with respect to the total amount of solids. is there. When the content of the polymerizable compound (C) is in 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.

<Polymerization initiator (D)>
The polymerization initiator (D) is not particularly limited as long as it is a compound capable of generating active radicals, acids and the like by the action of light and heat and initiating polymerization, and known polymerization initiators can be used.
As the polymerization initiator (D), a polymerization initiator containing at least one selected from the group consisting of alkylphenone compounds, triazine compounds, acyl phosphine oxide compounds, O-acyl oxime compounds and biimidazole compounds is preferable, and O-acyloxy is preferable. More preferred is a polymerization initiator containing a sulfur compound.

  As the O-acyl oxime compound, for example, N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane- 1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-one-2-imine, N-acetoxy-1- [9-ethyl-6- ( 2-Methylbenzoyl) -9H-carbazol-3-yl] ethane-1-imine, N-acetoxy-1- [9-ethyl-6- {2-methyl-4- (3,3-dimethyl-2,4 -Dioxacyclopentanylmethyloxy) benzoyl} -9H-carbazol-3-yl] ethane-1-imine, N-acetoxy-1- [9 Ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] -3-cyclopentylpropane-1-imine, N-benzoyloxy-1- [9-ethyl-6- (2-methylbenzoyl)- 9H-carbazol-3-yl] -3-cyclopentylpropan-1-one-2-imine and the like. You may use commercial products, such as Irgacure OXE01, OXE02 (above, BASF Corporation make), N-1919 (ADEKA company make), etc. An O-acyloxime compound is N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one At least one selected from the group consisting of -2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropan-1-one-2-imine is preferred, and N-benzoyloxy-1 is preferred. More preferred is-(4-phenylsulfanylphenyl) octan-1-one-2-imine. With these O-acyloxime compounds, high-brightness color filters tend to be obtained.

  The alkylphenone compound is 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one, 2-dimethylamino-1- (4-morpholinophenyl) -2-benzylbutane-1-l. On, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] butan-1-one, 2-hydroxy-2-methyl-1-phenyl Propan-1-one, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl] propan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1-one Oligomer of (4-isopropenylphenyl) propan-1-one, α, α-diethoxyacetophenone, benzyl dimethyl ketal Etc. You may use commercial products, such as Irgacure 369, 907, 379 (above, BASF Corporation make).

  As a triazine compound, 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxystyryl)- 1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis ( Trichloromethyl) -6- [2- (furan-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2-methyl] Phenyl) ethenyl 1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine.

  As an acyl phosphine oxide compound, 2,4,6- trimethyl benzoyl diphenyl phosphine oxide etc. are mentioned. You may use commercial items, such as Irgacure (registered trademark) 819 (made by BASF Corporation).

  As a biimidazole compound, for example, 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenylbiimidazole, 2,2′-bis (2,3-dichlorophenyl) -4 , 4 ', 5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372 and JP-A-6-75373), 2,2'-bis (2-chlorophenyl) -4, 4 ′, 5,5′-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 (trialkoxy) Phenyl) biimidazole (see, for example, JP-B-48-38403, JP-A-62-174204, etc.), the phenyl group at the 4,4'5,5'-position is substituted by a carboalkoxy group The imidazole compound (For example, refer Unexamined-Japanese-Patent No. 7-10913 etc.) etc. are mentioned.

  Furthermore, as a polymerization initiator (D), benzoin compounds such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether; benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl- Benzophenone compounds such as 4′-methyl diphenyl sulfide, 3,3 ′, 4,4′-tetra (tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone; 9,10-phenanthrenequinone, And quinone compounds such as 2-ethyl anthraquinone and camphorquinone; 10-butyl-2-chloroacridone, benzyl, methyl phenylglyoxylate, titanocene compounds and the like. It is preferable to use these in combination with the below-mentioned polymerization start auxiliary (D1) (especially amines).

  Examples of the acid generator include 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenylmethylbenzylsulfonium Onium salts such as hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, nitrobenzyl tosylates, benzoin tosylate Rate etc. are mentioned.

  The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, more preferably 1 to 20 parts by mass with respect to 100 parts by mass of the total amount of the resin (B) and the polymerizable compound (C). It is a mass part. When the content of the polymerization initiator (D) is in the above range, the sensitivity increases and the exposure time tends to be shortened, so that the productivity of the color filter is improved.

<Polymerization start assistant (D1)>
The polymerization initiation auxiliary (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 a polymerization initiator (D1) is contained, it is usually used in combination with the polymerization initiator (D).
Examples of the polymerization initiation auxiliary (D1) include amine compounds, alkoxyanthracene compounds, thioxanthone compounds and carboxylic acid compounds.

  Examples of amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 4- 2-ethylhexyl dimethylaminobenzoate, N, N-dimethyl paratoluidine, 4,4'-bis (dimethylamino) benzophenone (commonly called Michler's ketone), 4,4'-bis (diethylamino) benzophenone, 4,4'-bis Ethyl methylamino) benzophenone and the like can be mentioned, among which 4,4'-bis (diethylamino) benzophenone is preferable. You may use commercial items, such as EAB-F (made by Hodogaya Chemical Industry Co., Ltd.).

  As an alkoxyanthracene compound, 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, 9,10-dibutoxy Anthracene, 2-ethyl-9,10-dibutoxyanthracene and the like can be mentioned.

  Examples of the thioxanthone compound include 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-dichloro thioxanthone, 1-chloro-4-propoxy thioxanthone and the like.

  Examples of carboxylic acid compounds include phenylsulfanylacetic acid, methylphenylsulfanylacetic acid, ethylphenylsulfanylacetic acid, methylethylphenylsulfanylacetic acid, dimethylphenylsulfanylacetic acid, methoxyphenylsulfanylacetic acid, dimethoxyphenylsulfanylacetic acid, chlorophenylsulfanyl acetic acid, dichlorophenylsulfanyl acetic acid, N -Phenylglycine, phenoxyacetic acid, naphthylthioacetic acid, N-naphthylglycine, naphthoxyacetic acid and the like.

  When using a polymerization start auxiliary (D1), its content is preferably 0.1 to 30 parts by mass, more preferably 100 parts by mass with respect to the total amount of the resin (B) and the polymerizable compound (C). It is 1 to 20 parts by mass. When the amount of the polymerization initiator (D1) is in this range, a colored pattern can be formed with higher sensitivity, and the productivity of the color filter tends to be improved.

<Solvent (E)>
The solvent (E) is not particularly limited, and solvents commonly used in the relevant field can be used. For example, ester solvents (solvents containing -COO- in the molecule but not -O-), ether solvents (solvents containing -O- in the molecule and not -COO-), ether ester solvents (in molecules) Solvents containing -COO- and -O-), ketone solvents (solvents containing -CO- in the molecule but not -COO-), alcohol solvents (containing OH in the molecule, -O-,- Solvents not containing 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, butyl butyrate, ethyl butyrate, butyl butyrate And methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, cyclohexanol acetate and γ-butyrolactone.

  As ether solvents, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether Propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethyl Glycol methyl ethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, and the like phenetol and methyl anisole.

  As ether ester solvents, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 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 diethylene glycol monobutyl ether acetate.

  As ketone solvents, 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone and isophorone Etc.

  As an alcohol solvent, methanol, ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol and glycerin etc. may be mentioned.

  The aromatic hydrocarbon solvent includes 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 property and drying property. 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, 4-hydroxy-4-methyl-2-pentanone And N, N-dimethylformamide are preferable, and propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, ethyl lactate and ethyl 3-ethoxypropionate are more preferable.

  The content of the solvent (E) is preferably 70 to 95% by mass, more preferably 75 to 92% by mass, based on the total amount of the colored curable resin composition of the present invention. In other words, the total solid content of the colored curable resin composition is preferably 5 to 30% by mass, more preferably 8 to 25% by mass. When the content of the solvent (E) is in the above range, the flatness at the time of coating becomes good, and when the color filter is formed, the color density is not insufficient and the display characteristics tend to be good. .

<Leveling agent (F)>
Examples of the leveling agent (F) include silicone surfactants, fluorine surfactants, and silicone surfactants having a fluorine atom. These may have a polymerizable group in the side chain.
As silicone type surfactant, surfactant etc. which have a siloxane bond in a molecule | numerator are mentioned. Specifically, Toray silicone DC3PA, SH7PA, SH11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: Toray Dow Corning Co., Ltd. product), KP321, KP322, KP323, KP324 KP 326, KP 340, KP 341 (Shin-Etsu Chemical Co., Ltd.), TSF 400, TSF 401, TSF 410, TSF 4300, TSF 4440, TSF 4445, TSF 4446, TSF 4452 and TSF 4460 (manufactured by Momentive Performance Materials Japan GK) etc. .

  Examples of the fluorine-based surfactant include surfactants having a fluorocarbon chain in the molecule. Specifically, Florard (registered trademark) FC430, FC431 (manufactured by Sumitomo 3M Limited), Megafuck (registered trademark) F142D, F171, F172, F173, F177, F183, F554, and the like R30, RS-718-K (made by DIC Corporation), F-top (registered trademark) EF301, the same EF303, same EF351, the same EF 352 (manufactured by Mitsubishi Materials Electronic Chemicals, Ltd.), Surflon (registered trademark) S381, S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemical Research Co., Ltd.).

  Examples of the silicone surfactant having a fluorine atom include surfactants having a siloxane bond and a fluorocarbon chain in the molecule. Specific examples thereof include Megafuck (registered trademark) R08, BL20, F475, F477, and F443 (manufactured by DIC Corporation).

  The content of the leveling agent (F) is preferably 0.001% by mass or more and 0.2% by mass or less, preferably 0.002% by mass or more and 0.1% or less, based on the total amount of the colored curable resin composition. It is the mass% or less, more preferably 0.01 mass% or more and 0.05 mass% or less. When the content of the leveling agent (F) is in the above range, the flatness of the color filter can be improved.

<Other ingredients>
The colored curable resin composition of the present invention may contain, if necessary, additives known in the art such as fillers, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents and the like. May be included.

<Method of 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 the leveling agent (F), the polymerization initiator auxiliary (D1) and other components.
The dye (A2) and the optionally used dye (Ac) may be previously dissolved in part or all of the solvent (E) to prepare a solution. The solution is preferably filtered with a filter having a pore size of about 0.01 to 1 μm.
The blue pigment (A1) is preferably mixed with part or all of the solvent (E) in advance and dispersed using a bead mill or the like until the average particle size of the pigment becomes about 0.2 μm or less. At this time, part or all of the pigment dispersant and the resin (B) may be blended, if necessary. The target colored curable resin composition can be prepared by mixing the remaining components with the pigment dispersion thus obtained so as to have a predetermined concentration.
The colored curable resin composition after mixing is preferably filtered with a filter having a pore diameter of about 0.01 to 10 μm.

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

Hereinafter, the colored curable resin composition of the present invention will be described in more detail by way of examples.
Unless otherwise indicated, "%" and "parts" in the examples are% by mass and parts by mass.
In the following synthesis examples, compounds were identified by mass spectrometry (LC; Agilent 1200 type, MASS; Agilent LC / MSD type) or elemental analysis (VARIO-EL; (Elemental Co., Ltd.)).

Synthesis Example 1
In the reactor, 32.3 parts of pararose aniline hydrochloride (manufactured by Tokyo Kasei Kogyo Co., Ltd.) was added to 500 parts of absolute ethanol, refluxed for 8 hours, and cooled to room temperature. To the resulting mixture, 20.2 parts of a compound represented by the formula (a2-1) was slowly dropped over 5 hours. After dropwise addition, the resulting mixture was stirred at 70 ° C. for 36 hours, and then cooled to room temperature to obtain 48.8 parts of a compound represented by Formula (a2).

Synthesis Example 2
Dichloromethane (50 mL) was added to 28.52 parts of bis (N-ethyl-N-hydroxyethylaminobenzophenone) and 17.80 parts of triethylamine and dissolved with stirring. Thereafter, 13.56 parts of methacrylic anhydride were added, and the temperature was raised to 40 ° C. and maintained. After completion of the reaction, the reaction solution was cooled to room temperature, water was added, the layers were separated, 20 mL of saturated brine was added, and the mixture was stirred for 30 minutes. After layer separation, the organic layer was evaporated, and the remaining solid was dried under reduced pressure to obtain 21.4 parts of a compound represented by the formula (aa2).

21.4 parts of a compound represented by the formula (aa2) was added to 500 mL of chloroform and stirred. Thereafter, 49.08 parts of phosphorus oxychloride was additionally added and stirred for 15 minutes. After adding 14.56 parts of N-phenyl-1-naphthylamine, the solution was refluxed. After completion of the reaction, the reaction solution was cooled to room temperature, water was added and stirred. After stirring, the solution was allowed to stand to separate layers, the organic layer was distilled off, the remaining solid was dried under reduced pressure and purified to obtain 20.3 parts of a compound represented by formula (aa3).

Synthesis Example 3
After 10.00 parts of a compound represented by the formula (aa3) was added to 100 mL of methanol and dissolved, 2.09 parts of lithium bistrifluoromethanesulfonimide was added to replace the salt. After filtration, the obtained compound was washed with water and dried under reduced pressure to obtain 7.5 parts of a compound represented by the formula (aa5).

Synthesis Example 4-7
In a flask equipped with a condenser and a stirrer, the monomer represented by the formula (aa5), benzyl methacrylate, methacrylic acid, methyl methacrylate and N-benzyl maleimide are charged in the weight ratio described in Table 1 below, 2 6 parts by weight of 2,2′-azobis (2,4-dimethylvaleronitrile) (initiator) was added to 100 parts by weight of the total amount of the monomers. Subsequently, 300 parts by weight of propylene glycol monomethyl ether acetate was added to 100 parts by weight of the total of the initiator and the monomer, and then stirring was gradually started under a nitrogen atmosphere. The reaction solution was heated to 90 ° C. and stirred for 10 hours to obtain a copolymer solution.

Synthesis Example 8
The following reactions were performed under a nitrogen atmosphere. In a flask equipped with a condenser and a stirrer, 36.3 parts of potassium thiocyanate and 160.0 parts of acetone were charged, and the mixture was stirred at room temperature for 30 minutes. Subsequently, 50.0 parts of benzoic acid chlorides (made by Tokyo Kasei Co., Ltd.) were dripped over 10 minutes. After completion of the dropwise addition, the mixture was further stirred at room temperature for 2 hours. Then, the reaction mixture was ice-cooled, and then 45.7 parts of N-ethyl-o-toluidine (manufactured by Tokyo Kasei Kogyo Co., Ltd.) were dropped. After completion of the dropwise addition, the mixture was further stirred at room temperature for 30 minutes. Then, after ice-cooling the reaction mixture, 34.2 parts of a 30% aqueous solution of sodium hydroxide was added dropwise. After completion of the dropwise addition, the mixture was further stirred at room temperature for 30 minutes. Then, 35.3 parts of chloroacetic acid was dropped at room temperature. After completion of the dropwise addition, the mixture was stirred for 7 hours under heating and reflux. Then, after the reaction mixture was allowed to cool to room temperature, the reaction solution was poured into 120.0 parts of tap water, 200 parts of toluene was added, and the mixture was stirred for 30 minutes. Stirring was then stopped, and the mixture was allowed to stand for 30 minutes to separate into an organic layer and an aqueous layer. After the aqueous layer was discarded by separation operation, the organic layer was washed with 200 parts of 1 N hydrochloric acid, then with 200 parts of tap water, and finally with 200 parts of saturated saline. After adding a suitable amount of Bowshow to the organic layer and stirring for 30 minutes, it filtered and obtained the dried organic layer. The solvent of the obtained organic layer was distilled off with an evaporator to obtain a pale yellow liquid. The resulting pale yellow liquid was purified by column chromatography. The purified pale yellow liquid was dried at 60 ° C. under reduced pressure to obtain 52.0 parts of a compound represented by the formula (B-I-1). 50% yield

Synthesis Example 9
The following reactions were performed under a nitrogen atmosphere. In a flask equipped with a condenser and a stirrer, 9.3 parts of a compound represented by the formula (B-I-1), 4,4'-bis (diethylamino) benzophenone (manufactured by Tokyo Kasei Co., Ltd.) 10. After 0 parts and 20.0 parts of toluene were charged, 14.8 parts of phosphorus oxychloride were then added and the mixture was stirred at 95 to 100 ° C. for 3 hours. The reaction mixture was then cooled to room temperature and then diluted with 170.0 parts of isopropanol. Then, the diluted reaction solution was poured into 300.0 parts of saturated brine, 100 parts of toluene was added, and the mixture was stirred for 30 minutes. Stirring was then stopped, and the mixture was allowed to stand for 30 minutes to separate into an organic layer and an aqueous layer. The aqueous layer was discarded by separation operation, and then the organic layer was washed with 300 parts of saturated saline. After adding a suitable amount of Bowshow to the organic layer and stirring for 30 minutes, it filtered and obtained the dried organic layer. The solvent of the obtained organic layer was distilled off with an evaporator to obtain a bluish purple solid. Furthermore, the blue-violet solid was dried at 60 ° C. under reduced pressure to obtain 19.8 parts of a compound represented by the formula (A-I-a1). 100% yield

Identification of Compound Represented by Formula (A-I-a1) (Mass Spectrometry) Ionization Mode = ESI +: m / z = 601.3 [M-Cl] ⁺
Exact Mass: 636.3

Synthesis Example 10
The following reactions were performed under a nitrogen atmosphere. 10.0 parts of a compound represented by the formula (A-I-a1) and 4.5 parts of bis (trifluoromethanesulfonyl) imide lithium (manufactured by Tokyo Kasei Kogyo Co., Ltd.) in a flask equipped with a condenser and a stirrer And 100.0 parts of N, N-dimethylformamide were added, followed by stirring at 50 to 60 ° C. for 3 hours. The reaction mixture was then cooled to room temperature and then added dropwise to 2000.0 parts of tap water with stirring for 1 hour to obtain a dark blue suspension. The resulting suspension was filtered to give a turquoise solid. Furthermore, the blue-green solid was dried at 60 ° C. under reduced pressure to obtain 11.3 parts of a compound represented by the formula (A-I-a9). 82% yield

一方、重合開始剤２，２’−アゾビス（２，４−ジメチルバレロニトリル）３０質量部を乳酸エチル２２５質量部に溶解した溶液を、別の滴下ロートを用いて４時間かけてフラスコ内に滴下した。重合開始剤の溶液の滴下が終了した後、４時間、７０℃に保持し、その後室温まで冷却して、重量平均分子量Ｍｗは、９．１×１０^３、分子量分布は２．１、固形分２６質量％、固形分酸価１２０ｍｇ−ＫＯＨ／ｇの樹脂Ｂ１溶液を得た。樹脂Ｂ１は下記に示す構造単位を有する。

Synthesis Example 11
In a flask equipped with a reflux condenser, a dropping funnel and a stirrer, nitrogen was flushed at 0.02 L / min to make a nitrogen atmosphere, and 305 parts by mass of ethyl lactate was charged and heated to 70 ° C. while stirring. Subsequently, a compound represented by 46 parts by mass of acrylic acid and 3,4-epoxytricyclo [5.2.1.0 ^2.6 ] decyl acrylate (formula (I-1)) and formula (II-1) The resulting compound is mixed at a molar ratio of 50: 50.) A solution is prepared by dissolving 240 parts by mass of ethyl lactate in 185 parts by mass of ethyl lactate, and the solution is added using a dropping funnel for 4 hours. The solution was dropped into a flask kept at 70 ° C.

On the other hand, a solution of 30 parts by mass of a polymerization initiator 2,2'-azobis (2,4-dimethylvaleronitrile) dissolved in 225 parts by mass of ethyl lactate is dropped into the flask over 4 hours using another dropping funnel. did. After the addition of the polymerization initiator solution is completed, the temperature is maintained at 70 ° C. for 4 hours, and then cooled to room temperature, and the weight average molecular weight Mw is 9.1 × 10 ³ , the molecular weight distribution is 2.1, and the solid content The resin B1 solution of 26 mass% and solid content acid value 120 mg-KOH / g was obtained. Resin B1 has a structural unit shown below.

Synthesis Example 12
After introducing 182 parts of propylene glycol monomethyl ether acetate into a flask equipped with a stirrer, thermometer, reflux condenser, dropping funnel and nitrogen inlet tube and changing the atmosphere in the flask from air to nitrogen, the temperature is raised to 100 ° C. 2) in a mixture of 70.5 parts of benzyl methacrylate, 43.0 parts of methacrylic acid, 22.0 parts of monocyclomethacrylate of tricyclodecane skeleton (FA-513M manufactured by Hitachi Chemical Co., Ltd.) and 136 parts of propylene glycol monomethyl ether acetate A solution to which 3.6 parts of 2,2'-azobisisobutyronitrile was added was added dropwise, and stirring was further continued at 100 ° C.
Next, the atmosphere in the flask is changed from nitrogen to air, 35.5 parts of glycidyl methacrylate [0.25 mol, (50 mol% with respect to the carboxyl group of methacrylic acid used in this reaction)], trisdimethylaminomethylphenol 0 .9 parts and 0.145 parts of hydroquinone were charged into the flask, and the reaction was continued at 110 ° C to obtain a resin B2 solution having a solid content of 29% and a solid content acid value of 79 mg KOH / g. The polystyrene equivalent weight average molecular weight measured by GPC was 30,000.

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 under the following conditions using a GPC method.
Device: 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
Calibration standard substance; TSK STANDARD POLYSTYRENE F-40, F-4, F-288, A-2500, A-500 (manufactured by Tosoh Corp.)
The ratio (Mw / Mn) of the weight average molecular weight in terms of polystyrene and the number average molecular weight obtained above was taken as a molecular weight distribution.

Synthesis Example 13
A compound is synthesized in the same manner as in Synthesis Example 6 except that a compound represented by Formula (B-I-1) is used instead of N-phenyl-1-naphthylamine in Synthesis Example 2, and is represented by Formula (aa13). The compound is obtained.

Synthesis Example 14-17
A copolymer solution was prepared in the same manner as in Synthesis Example 4-7, except that the monomer represented by Formula (aa13) was used instead of the monomer represented by Formula (aa5). I got

Synthesis Example 18
22.14 parts of disodium 4-formylbenzene-1,3-disulfonate, 15.6 parts of N, N-dibutyl-3-aminophenol and 2.2 parts of sodium para-toluenesulfonate are stirred at 120 ° C. for 12 hours did. After cooling, the resulting mixture was added to 100 parts of 50% water of ethanol and filtered to obtain a compound represented by formula (I-2).

Synthesis Example 19
After 10.00 parts of a compound represented by the formula (aa3) was added to and dissolved in 100 mL of methanol, 2.50 parts of sodium trifluoromethanesulfonate was added to replace the salt. After filtration, the obtained compound was washed with water, and the remaining solid was dried under reduced pressure to obtain 5.5 parts of a compound represented by formula (aa4).

Synthesis Example 20
After 30 parts of methyl ethyl ketone was added under a nitrogen atmosphere, the temperature was raised to 70.degree. The compound was dissolved in 2.54 parts of a compound represented by the formula (aa4), 0.16 parts of 2,2'-azobisisobutyronitrile, and 20 parts of methyl ethyl ketone, and was charged to the reactor for 3 hours while maintaining 70 ° C. . After completion of the addition, the mixture is maintained at 70 ° C. for 8 hours to partially concentrate methyl ethyl ketone, and then the reaction solution is added to hexane to precipitate crystals, followed by filtration and washing of the remaining solid with hexane and drying under reduced pressure. Thus, 1.80 parts of a polymer compound (aa4) was obtained.

Synthesis Example 21
After 30 parts of methyl ethyl ketone was added under a nitrogen atmosphere, the temperature was raised to 70.degree. 2.54 parts of a compound represented by the formula (aa4) and 0.25 parts of 2,2′-azobisisobutyronitrile, 0.51 parts of benzyl methacrylate, 0.51 parts of methacrylic acid, N-phenylmaleimide 0.42 parts was dissolved in 50 parts of methyl ethyl ketone and charged to the reactor for 3 hours while maintaining 70 ° C. After completion of the addition, the mixture is maintained at 70 ° C. for 8 hours to partially concentrate methyl ethyl ketone, and then the reaction solution is added to hexane to precipitate crystals, followed by filtration and washing of the remaining solid with hexane and drying under reduced pressure. As a result, 2.35 parts of a polymer compound (aa4 ') was obtained.

Synthesis Example 22
After 30 parts of methyl ethyl ketone was added under a nitrogen atmosphere, the temperature was raised to 70.degree. The compound was dissolved in 2.54 parts of a compound represented by the formula (aa5), 0.16 parts of 2,2'-azobisisobutyronitrile, and 20 parts of methyl ethyl ketone, and was charged to the reactor for 3 hours while maintaining 70 ° C. . After completion of the addition, the mixture is maintained at 70 ° C. for 8 hours to partially concentrate methyl ethyl ketone, and then the reaction solution is added to hexane to precipitate crystals, followed by filtration and washing of the remaining solid with hexane and drying under reduced pressure. Thus, 1.63 parts of a polymer compound (aa5) was obtained.

Synthesis Example 23
After 30 parts of methyl ethyl ketone is added under a nitrogen atmosphere, the temperature is raised to 70.degree. 2.54 parts of a compound represented by the formula (aa5) and 0.25 parts of 2,2′-azobisisobutyronitrile, 0.51 parts of benzyl methacrylate, 0.51 parts of methacrylic acid, N-phenylmaleimide 0.42 parts is dissolved in 50 parts of methyl ethyl ketone and charged to the reactor for 3 hours maintaining 70 ° C. After the addition is completed, the temperature is maintained at 70 ° C. for 15 hours, methyl ethyl ketone is partially concentrated, the reaction solution is poured into hexane, crystals are precipitated, and then filtered, and the remaining solid is dried under reduced pressure to obtain a polymer compound ( aa5 ') 3.80 parts were obtained.

Synthesis Example 24
5.00 parts of a compound represented by the formula (aa3) is added to 50 mL of methanol and dissolved, and then 1.46 parts of p-toluenesulfonic acid sodium salt is added to replace the salt. After filtration, the obtained compound is washed with water and dried under reduced pressure to obtain 2.84 parts of a compound represented by formula (aa6).

Synthesis Example 25
C. I. After dissolving 5.00 parts of Basic Blue 26 in 50 mL of methanol and dissolving, 2.10 parts of p-toluenesulfonic acid sodium salt is added to replace the salt. After filtration, the obtained compound is washed with water and dried under reduced pressure to give 2.71 parts of a compound represented by formula (aa7).

Synthesis Example 26-29
The monomer represented by the formula (aa8), benzyl methacrylate, methacrylic acid, methyl methacrylate and N-benzyl maleimide were respectively introduced into a flask equipped with a condenser and a stirrer at a weight described in Table 3 below, and then started. As an agent, 0.25 parts of 2,2'-azobisisobutyronitrile, and 6 parts by weight of benzyl methacrylate with respect to 100 parts by weight of the total amount of the above monomers are added. Next, 300 parts by weight of propylene glycol monomethyl ether acetate (PGMEA) as a solvent is added to 100 parts by weight of the total amount of the initiator and the monomer, and then stirring is gradually started under a nitrogen atmosphere. The reaction solution is heated to 90 ° C. and stirred for 10 hours to obtain a copolymer solution.

Synthesis Example 30-33
A copolymer solution was prepared in the same manner as in Synthesis Example 26-29, except that the monomer represented by Formula (aa9) was used instead of the monomer represented by Formula (aa8). obtain.

Synthesis Example 34-37
A copolymer solution was prepared in the same manner as in Synthesis Example 26-29, except that the monomer represented by Formula (aa10) was used instead of the monomer represented by Formula (aa8). obtain.

Synthesis Example 38
After dissolving 2.1 parts of Basic Blue 7 (Tokyo Kasei Co., Ltd.) in 100 parts of methanol, 2.1 parts of a compound represented by the following formula (Pc) (manufactured by Aldrich Co., Ltd.) is added, and the reaction is carried out for 12 hours Stir at room temperature. Thereafter, 100 parts of ion exchanged water was added to precipitate crystals. After filtration, the crystals were washed with 50 parts of ion-exchanged water, and the obtained solid was dried at 60 ° C. for 24 hours to obtain a compound represented by the formula (a-4).

（Ａ）着色剤：Ｃ．Ｉ．アシッドレッド５２ １．０部
（Ｂ）樹脂：樹脂Ｂ１（固形分換算） ５０部
（Ｃ）重合性化合物：ジペンタエリスリトールヘキサアクリレート
（カヤラッド（登録商標）ＤＰＨＡ；日本化薬（株）製） ５０部
（Ｄ）重合開始剤：Ｎ−ベンゾイルオキシ−１−（４−フェニルスルファニルフェニル）オクタン−１−オン−２−イミン（イルガキュア（登録商標）ＯＸＥ ０１；ＢＡＳＦ社製） １０部
（Ｆ）レベリング剤：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） ０．１部
（Ｅ）溶剤：乳酸エチル ６００部
（Ｅ）溶剤：プロピレングリコールモノメチルエーテルアセテート １０部
を混合して着色硬化性樹脂組成物を得た。 Example 1
(Preparation of Colored Curable Resin Composition)
(A) Colorant: 10 parts of a compound represented by the formula (a-1)

(A) Colorant: C.I. I. Acid Red 52 1.0 part (B) Resin: resin B1 (solid content conversion) 50 part (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 Part (D) Polymerization initiator: N-Benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF) 10 parts (F) Leveling Agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: Ethyl lactate 600 parts (E) Solvent: Propylene glycol monomethyl ether acetate 10 parts mixed A colored curable resin composition was obtained.

（Ｂ）樹脂：樹脂Ｂ１（固形分換算） ５０部
（Ｃ）重合性化合物：ジペンタエリスリトールヘキサアクリレート
（カヤラッド（登録商標）ＤＰＨＡ；日本化薬（株）製） ５０部
（Ｄ）重合開始剤：Ｎ−ベンゾイルオキシ−１−（４−フェニルスルファニルフェニル）オクタン−１−オン−２−イミン（イルガキュア（登録商標）ＯＸＥ ０１；ＢＡＳＦ社製） １０部
（Ｆ）レベリング剤：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） ０．１部
（Ｅ）溶剤：乳酸エチル ６００部
（Ｅ）溶剤：プロピレングリコールモノメチルエーテルアセテート １０部
を混合して着色硬化性樹脂組成物を得た。 Example 2
(Preparation of Colored Curable Resin Composition)
(A) Coloring agent: 10 parts of a compound represented by the formula (a-1) (A) Coloring agent: 1.0 part of a compound represented by the formula (I-2)

(B) Resin: resin B1 (solid content conversion) 50 parts (C) polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) polymerization initiator N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF) 10 parts (F) Leveling agent: polyether-modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: 600 parts of ethyl lactate (E) Solvent: 10 parts of propylene glycol monomethyl ether acetate are mixed to obtain a colored curable resin composition Obtained.

[Example 3]
(Preparation of Colored Curable Resin Composition)
(A) Colorant: compound represented by the formula (a-1) 2.0 parts (A) Colorant: C.I. I. Acid Red 52 0.5 part (A) Colorant: compound represented by the formula (a2) 6.0 part (B) Resin: resin B1 (solid content conversion) 50 part (C) Polymerizable compound: dipentaerythritol Hexa acrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) polymerization initiator: N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF) 10 parts (F) Leveling agent: Polyether modified silicone oil (Toray silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: lactic acid Ethyl 600 parts (E) Solvent: 10 parts of propylene glycol monomethyl ether acetate were mixed to obtain a colored curable resin composition.

Example 4
(Preparation of Colored Curable Resin Composition)
(A) Colorant: Compound represented by Formula (a-1) 2.0 parts (A) Colorant: Compound represented by Formula (I-2) 0.5 part (A) Colorant: Formula ( Compound represented by a2) 5.8 parts (B) Resin: resin B1 (solid content equivalent) 50 parts (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; Nippon Kayaku Co., Ltd. Made of) 50 parts (D) Polymerization initiator: N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF) 10 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: ethyl lactate 600 parts (E) Solvent: propylene glycol A colored curable resin composition was obtained by mixing 10 parts of monomethyl ether acetate.

（Ｂ）樹脂：樹脂Ｂ１（固形分換算） ５０部
（Ｃ）重合性化合物：ジペンタエリスリトールヘキサアクリレート
（カヤラッド（登録商標）ＤＰＨＡ；日本化薬（株）製） ５０部
（Ｄ）重合開始剤：Ｎ−ベンゾイルオキシ−１−（４−フェニルスルファニルフェニル）オクタン−１−オン−２−イミン（イルガキュア（登録商標）ＯＸＥ ０１；ＢＡＳＦ社製） １０部
（Ｆ）レベリング剤：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） ０．１部
（Ｅ）溶剤：乳酸エチル ６００部
（Ｅ）溶剤：プロピレングリコールモノメチルエーテルアセテート １０部
を混合して着色硬化性樹脂組成物を得た。 [Example 5]
(Preparation of Colored Curable Resin Composition)
(A) Colorant: compound represented by the formula (a-1) 2.0 parts (A) Colorant: C.I. I. Acid Red 52 0.5 parts

(B) Resin: resin B1 (solid content conversion) 50 parts (C) polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) polymerization initiator N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF) 10 parts (F) Leveling agent: polyether-modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: 600 parts of ethyl lactate (E) Solvent: 10 parts of propylene glycol monomethyl ether acetate are mixed to obtain a colored curable resin composition Obtained.

（Ｂ）樹脂：樹脂Ｂ１（固形分換算） ５０部
（Ｃ）重合性化合物：ジペンタエリスリトールヘキサアクリレート
（カヤラッド（登録商標）ＤＰＨＡ；日本化薬（株）製） ５０部
（Ｄ）重合開始剤：Ｎ−ベンゾイルオキシ−１−（４−フェニルスルファニルフェニル）オクタン−１−オン−２−イミン（イルガキュア（登録商標）ＯＸＥ ０１；ＢＡＳＦ社製） １０部
（Ｆ）レベリング剤：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） ０．１部
（Ｅ）溶剤：乳酸エチル ６００部
（Ｅ）溶剤：プロピレングリコールモノメチルエーテルアセテート １０部
を混合して着色硬化性樹脂組成物を得た。 [Example 6]
(Preparation of Colored Curable Resin Composition)
(A) Colorant: compound represented by the formula (a-1) 2.0 parts (A) Colorant: C.I. I. Acid Red 52 0.5 part (A) Colorant (A6): Compound represented by Formula (3-11) 1.3 parts

(B) Resin: resin B1 (solid content conversion) 50 parts (C) polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) polymerization initiator N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF) 10 parts (F) Leveling agent: polyether-modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: 600 parts of ethyl lactate (E) Solvent: 10 parts of propylene glycol monomethyl ether acetate are mixed to obtain a colored curable resin composition Obtained.

（Ｂ）樹脂：樹脂Ｂ１（固形分換算） ５０部
（Ｃ）重合性化合物：ジペンタエリスリトールヘキサアクリレート
（カヤラッド（登録商標）ＤＰＨＡ；日本化薬（株）製） ５０部
（Ｄ）重合開始剤：Ｎ−ベンゾイルオキシ−１−（４−フェニルスルファニルフェニル）オクタン−１−オン−２−イミン（イルガキュア（登録商標）ＯＸＥ ０１；ＢＡＳＦ社製） １０部
（Ｆ）レベリング剤：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） ０．１部
（Ｅ）溶剤：乳酸エチル ５５０部
（Ｅ）溶剤：プロピレングリコールモノメチルエーテルアセテート １０部
を混合して着色硬化性樹脂組成物を得た。 [Example 7]
(Preparation of Colored Curable Resin Composition)
(A) Colorant: Compound represented by Formula (a-1) 2.0 parts (A) Colorant: C.I. I. Acid Red 52 0.3 part (A) Colorant (A7): compound represented by the formula (A-I-a9) 5.0 parts

(B) Resin: resin B1 (solid content conversion) 50 parts (C) polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) polymerization initiator N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF) 10 parts (F) Leveling agent: polyether-modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: ethyl lactate 550 parts (E) Solvent: propylene glycol monomethyl ether acetate 10 parts are mixed to prepare a colored curable resin composition Obtained.

Example 8
(Preparation of Colored Curable Resin Composition)
(A) Colorant: Compound represented by Formula (a-1) 2.0 parts (A) Colorant: C.I. I. Acid Red 52 0.3 part (A) Colorant: 5.0 parts of copolymer solution obtained in Synthesis Example 4 (B) Resin: Resin B1 (solid content conversion) 50 parts (C) Polymerizable compound: Di Pentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) polymerization initiator: N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2 -Imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF) 10 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent : Ethyl lactate 550 parts (E) Solvent: Propylene glycol monomethyl ether acetate 10 parts are mixed to make a colored curable resin composition It was.

[Example 9]
(Preparation of Colored Curable Resin Composition)
(A) Colorant: Compound represented by Formula (a-1) 2.0 parts (A) Colorant: C.I. I. Acid Red 52 0.3 part (A) Coloring agent: 5.0 parts of copolymer solution obtained in Synthesis Example 5 (B) Resin: Resin B1 (solid content conversion) 50 parts (C) Polymerizable compound: Di Pentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) polymerization initiator: N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2 -Imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF) 10 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent : Ethyl lactate 550 parts (E) Solvent: Propylene glycol monomethyl ether acetate 10 parts are mixed to make a colored curable resin composition It was.

[Example 10]
(Preparation of Colored Curable Resin Composition)
(A) Colorant: Compound represented by Formula (a-1) 2.0 parts (A) Colorant: C.I. I. Acid Red 52 0.3 part (A) Coloring agent: 5.0 parts of the copolymer solution obtained in Synthesis Example 6 (B) Resin: Resin B1 (solid content conversion) 50 parts (C) Polymerizable compound: Di Pentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) polymerization initiator: N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2 -Imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF) 10 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent : Ethyl lactate 550 parts (E) Solvent: Propylene glycol monomethyl ether acetate 10 parts are mixed to make a colored curable resin composition It was.

[Example 11]
(Preparation of Colored Curable Resin Composition)
(A) Colorant: Compound represented by Formula (a-1) 2.0 parts (A) Colorant: C.I. I. Acid Red 52 0.3 part (A) Coloring agent: 5.0 parts of copolymer solution obtained in Synthesis Example 7 (B) Resin: Resin B1 (solid content conversion) 50 parts (C) Polymerizable compound: Di Pentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) polymerization initiator: N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2 -Imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF) 10 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent : Ethyl lactate 550 parts (E) Solvent: Propylene glycol monomethyl ether acetate 10 parts are mixed to make a colored curable resin composition It was.

[Example 12]
(Preparation of Colored Curable Resin Composition)
(A) Colorant: Compound represented by Formula (a-1) 2.0 parts (A) Colorant: C.I. I. Acid Red 52 0.3 part (A) Coloring agent: 5.0 parts of the copolymer solution obtained in Synthesis Example 14 (B) Resin: Resin B1 (solid content conversion) 50 parts (C) Polymerizable compound: Di Pentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) polymerization initiator: N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2 -Imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF) 10 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent : Ethyl lactate 550 parts (E) Solvent: Propylene glycol monomethyl ether acetate 10 parts are mixed and colored curable resin composition Obtained.

[Example 13]
(Preparation of Colored Curable Resin Composition)
(A) Colorant: Compound represented by Formula (a-1) 2.0 parts (A) Colorant: C.I. I. Acid Red 52 0.3 part (A) Colorant: 5.0 parts of the copolymer solution obtained in Synthesis Example 15 (B) Resin: Resin B1 (solid content conversion) 50 parts (C) Polymerizable compound: Di Pentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) polymerization initiator: N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2 -Imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF) 10 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent : Ethyl lactate 550 parts (E) Solvent: Propylene glycol monomethyl ether acetate 10 parts are mixed and colored curable resin composition Obtained.

Example 14
(Preparation of Colored Curable Resin Composition)
(A) Colorant: Compound represented by Formula (a-1) 2.0 parts (A) Colorant: C.I. I. Acid Red 52 0.3 part (A) Coloring agent: 5.0 parts of copolymer solution obtained in Synthesis Example 16 (B) Resin: Resin B1 (solid content conversion) 50 parts (C) Polymerizable compound: Di Pentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) polymerization initiator: N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2 -Imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF) 10 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent : Ethyl lactate 550 parts (E) Solvent: Propylene glycol monomethyl ether acetate 10 parts are mixed and colored curable resin composition Obtained.

[Example 15]
(Preparation of Colored Curable Resin Composition)
(A) Colorant: Compound represented by Formula (a-1) 2.0 parts (A) Colorant: C.I. I. Acid Red 52 0.3 part (A) Coloring agent: 5.0 parts of copolymer solution obtained in Synthesis Example 17 (B) Resin: Resin B1 (solid content conversion) 50 parts (C) Polymerizable compound: Di Pentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 parts (D) polymerization initiator: N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2 -Imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF) 10 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent : Ethyl lactate 550 parts (E) Solvent: Propylene glycol monomethyl ether acetate 10 parts are mixed and colored curable resin composition Obtained.

[Example 16]
(Preparation of Colored Curable Resin Composition)
(A) Colorant: compound represented by the formula (a-4) 0.8 part (A) Colorant: C.I. I. Acid Red 52 0.3 part (B) Resin: resin B1 (solid content conversion) 50 part (C) Polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 50 Part (D) Polymerization initiator: N-Benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (IRGACURE (registered trademark) OXE 01; manufactured by BASF) 10 parts (F) Leveling Agent: Polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: Ethyl lactate 550 parts (E) Solvent: Propylene glycol monomethyl ether acetate 10 parts mixed A colored curable resin composition was obtained.

[Example 17]
(Preparation of Colored Curable Resin Composition)
A colored curable resin composition is obtained in the same manner as in Example 1 except that the compound represented by the formula (aa4) obtained in Synthesis Example 7 is used instead of the xanthene dye.

[Example 18]
(Preparation of Colored Curable Resin Composition)
A colored curable resin composition is obtained in the same manner as in Example 1 except that the compound represented by the formula (aa5) obtained in Synthesis Example 8 is used instead of the xanthene dye.

[Example 19]
(Preparation of Colored Curable Resin Composition)
A colored curable resin composition is obtained in the same manner as in Example 3, except that the polymer compound (aa4 ′) obtained in Synthesis Example 21 is used instead of the compound represented by Formula (a2).

Example 20
(Preparation of Colored Curable Resin Composition)
A colored curable resin composition is obtained in the same manner as in Example 3, except that the polymer compound (aa5) obtained in Synthesis Example 22 is used instead of the compound represented by Formula (a2).

[Example 21]
(Preparation of Colored Curable Resin Composition)
A colored curable resin composition is obtained in the same manner as in Example 3, except that the polymer compound (aa5 ') obtained in Synthesis Example 23 is used instead of the compound represented by Formula (a2).

[Example 22]
(Preparation of Colored Curable Resin Composition)
A colored curable resin composition is obtained in the same manner as in Example 3, except that the polymer compound (aa6) obtained in Synthesis Example 24 is used instead of the compound represented by Formula (a2).

[Example 23]
(Preparation of Colored Curable Resin Composition)
A colored curable resin composition is obtained in the same manner as in Example 3, except that the polymer compound (aa7) obtained in Synthesis Example 25 is used instead of the compound represented by Formula (a2).

[Example 24]
(Preparation of Colored Curable Resin Composition)
A colored curable resin composition is obtained in the same manner as in Example 3, except that the copolymer dispersion obtained in Synthesis Example 26 is used instead of the compound represented by the formula (a2).

[Example 25]
(Preparation of Colored Curable Resin Composition)
A colored curable resin composition is obtained in the same manner as in Example 3, except that the copolymer dispersion obtained in Synthesis Example 27 is used instead of the compound represented by the formula (a2).

[Example 26]
(Preparation of Colored Curable Resin Composition)
A colored curable resin composition is obtained in the same manner as in Example 3, except that the copolymer dispersion obtained in Synthesis Example 28 is used instead of the compound represented by the formula (a2).

[Example 27]
(Preparation of Colored Curable Resin Composition)
A colored curable resin composition is obtained in the same manner as in Example 3, except that the copolymer dispersion obtained in Synthesis Example 29 is used instead of the compound represented by the formula (a2).

[Example 28]
(Preparation of Colored Curable Resin Composition)
A colored curable resin composition is obtained in the same manner as in Example 3, except that the copolymer dispersion obtained in Synthesis Example 30 is used instead of the compound represented by the formula (a2).

[Example 29]
(Preparation of Colored Curable Resin Composition)
A colored curable resin composition is obtained in the same manner as in Example 3 except that the copolymer dispersion obtained in Synthesis Example 31 is used instead of the compound represented by the formula (a2).

[Example 30]
(Preparation of Colored Curable Resin Composition)
A colored curable resin composition is obtained in the same manner as in Example 3, except that the copolymer dispersion obtained in Synthesis Example 32 is used instead of the compound represented by the formula (a2).

Example 31
(Preparation of Colored Curable Resin Composition)
A colored curable resin composition is obtained in the same manner as in Example 3, except that the copolymer dispersion obtained in Synthesis Example 33 is used instead of the compound represented by the formula (a2).

[Example 32]
(Preparation of Colored Curable Resin Composition)
A colored curable resin composition is obtained in the same manner as in Example 3, except that the copolymer dispersion obtained in Synthesis Example 34 is used instead of the compound represented by the formula (a2).

[Example 33]
(Preparation of Colored Curable Resin Composition)
A colored curable resin composition is obtained in the same manner as in Example 3, except that the copolymer dispersion obtained in Synthesis Example 35 is used instead of the compound represented by the formula (a2).

[Example 34]
(Preparation of Colored Curable Resin Composition)
A colored curable resin composition is obtained in the same manner as in Example 3, except that the copolymer dispersion obtained in Synthesis Example 36 is used instead of the compound represented by the formula (a2).

[Example 35]
(Preparation of Colored Curable Resin Composition)
A colored curable resin composition is obtained in the same manner as in Example 3, except that the copolymer dispersion obtained in Synthesis Example 37 is used instead of the compound represented by the formula (a2).

[Example 38]
(Preparation of Colored Curable Resin Composition)
Using a compound represented by Formula (4-9) instead of the compound represented by Formula (a2), C.I. I. A colored curable resin composition is obtained in the same manner as in Example 3 except that the pigment violet 23 is contained.

[Example 39]
(Preparation of Colored Curable Resin Composition)
Using a compound represented by the formula (1-44) instead of the compound represented by the formula (a2); I. A colored curable resin composition is obtained in the same manner as in Example 3 except that the pigment violet 23 is contained.

Comparative Example 1
(Preparation of Colored Curable Resin Composition)
(A) coloring agent: compound represented by the formula (a-1) 10 parts (B) resin: resin B1 (solid content conversion) 50 parts (C) polymerizable compound: dipentaerythritol hexaacrylate (Kayarad (registered trademark) ) DPHA; 50 parts of Nippon Kayaku Co., Ltd. (D) Polymerization initiator: N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (IRGACURE (registered trademark) OXE) 01: BASF Corporation 10 parts (F) Leveling agent: Polyether modified silicone oil (Toray Silicone SH8400: Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: Ethyl lactate 600 parts (E) Solvent : 10 parts of propylene glycol monomethyl ether acetate was mixed to obtain a colored curable resin composition.

Comparative Example 2
(Preparation of Colored Curable Resin Composition)
(A) Coloring Agent: Compound Represented by Formula (a-4) 0.8 Part (B) Resin: Resin B1 (In terms of Solid Content) 50 Part (C) Polymerizable Compound: Dipentaerythritol Hexaacrylate (Kayarad ( (Registered trademark) DPHA; 50 parts of Nippon Kayaku Co., Ltd. (D) polymerization initiator: N-benzoyloxy-1- (4-phenylsulfanylphenyl) octan-1-one-2-imine (IRGACURE (registered trademark) ) OXE 01; BASF Corporation 10 parts (F) Leveling agent: polyether modified silicone oil (Toray Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.1 part (E) Solvent: ethyl lactate 550 parts (E ) Solvent: 10 parts of propylene glycol monomethyl ether acetate were mixed to obtain a colored curable resin composition.

<Preparation of colored pattern>
A colored curable resin composition was applied by spin coating on a 5 cm square glass substrate (Eagle 2000; manufactured by Corning), and then prebaked at 100 ° C. for 3 minutes to obtain a colored layer. After leaving to cool, the distance between the substrate on which the colored layer is formed and the quartz glass photomask is set to 100 μm, and 150 mJ / cm ^{2 in} an air atmosphere using an exposure unit (TME-150RSK; Topcon Co., Ltd.). Light was irradiated at an exposure dose (365 nm standard). As a photomask, a photomask on which a 100 μm line and space pattern was formed was used. The colored layer after light irradiation is developed by immersion in an aqueous developer containing 0.12% of a nonionic surfactant and 0.04% of potassium hydroxide for 60 seconds at 24 ° C., and after water washing, in an oven at 200 ° C. Post-baking was performed for 30 minutes to obtain a colored pattern.

<Film thickness measurement>
The film thickness of the obtained colored pattern was measured using a film thickness measuring device (DEKTAK3; manufactured by Nippon Vacuum Technology Co., Ltd.).

<Chromaticity evaluation>
The obtained colored pattern is measured for its spectrum by using a colorimeter (OSP-SP-200; manufactured by Olympus Corporation), and xy chromaticity coordinates in the CIE XYZ color system using the characteristic function of a C light source. (X, y) and tristimulus values Y were measured. The larger the value of Y, the higher the lightness.

[Heat resistance evaluation]
The coating film of the obtained colored photosensitive resin composition is heated at 230 ° C. for 20 minutes, and the color difference (ΔEab *) before and after heating of the coating film is measured using a colorimeter (OSP-SP-200; manufactured by OLYMPUS). It was measured. As a result of performing the above-mentioned heat resistance evaluation about the obtained coating film, color difference ((DELTA) Eab *) is shown in Table 6-Table 9. The smaller the ΔEab *, the smaller the color change before and after heating, and the better the heat resistance.

  The colored coating film and the colored pattern formed from the colored curable resin composition of the present invention have good heat resistance and good brightness. It is understood that a color filter formed from the colored curable resin composition of the present invention is useful, and a liquid crystal display device including the color filter is excellent in display characteristics.

Claims (2)

A colored curable resin composition comprising a colorant (A), a resin (B), a polymerizable compound (C) and a polymerization initiator (D),
A compound represented by the formula (a):
At least one selected from the group consisting of salts with xanthene dyes and xanthene dyes and cyanine dyes seen including,
The xanthene dyes are C.I. I. Colored curable resin composition which is a compound represented by Acid Red 52 or the following formula (I) .

[Wherein, k 1, k 2, k 3 and k 4 each independently represent an integer of 0 to 4 and 1 ≦ k 1 + k 2 + k 3 + k 4 ≦ 16.
Each of X _a ⁻ , X _b ⁻ , X _c ⁻ and X _d ⁻ independently represents —CO ₃ ^— or —SO ₃ ^— .
A _a ⁺ , A _b ⁺ , A _c ⁺ and A _d ⁺ each independently represent a sodium ion, a potassium ion or a cation represented by the formula (b).

In formula (b), R ¹⁰⁰ , R ¹⁰¹ , R ¹⁰² and R ¹⁰³ each independently represent a hydrogen atom or a hydrocarbon group having 1 to 30 carbon atoms. ]

[In formula (I), R ¹ , R ² , R ³ and R ⁴ are each independently a monovalent saturated hydrocarbon group having 2 to 10 carbon atoms which may have a substituent or a substituent Represents an aryl group which may be possessed.
R ^51, R ⁵² and R ⁵³ are each independently a hydrogen atom, -SO ₃ ^-, -SO ₃ H or -SO ₃ ^- represents a Z ^+.
Z ⁺ each independently represents ⁺ N (R ¹³ ) ₄ , Na ⁺ or K ⁺ , and R ¹³ represents a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms. R ¹³ may be the same or different.
X ⁺ each independently represents Na ⁺ or K ⁺ .
a represents an integer of 1 to 4; ] The colored curable resin composition according to claim 1, wherein the colorant (A) further comprises a blue or purple dye (A2).