JP7101295B2 - Compound and color curable resin composition - Google Patents

Description

The present invention relates to compounds and color curable resin compositions.

The color curable resin composition is used in the manufacture of color filters used in display devices such as liquid crystal displays, electroluminescence display devices and plasma displays. As such a color-curable resin composition, a color-curable resin composition containing a compound represented by the following formula or the like is known.

Japanese Unexamined Patent Publication No. 2010-32999

The brightness of the color filter formed from the conventionally known color-curable resin composition containing the above compound may not be sufficiently satisfactory.

［式（Ｉ）中、Ｒ¹～Ｒ⁴は、互いに独立に、水素原子、置換基を有していてもよい炭素数１～２０の飽和炭化水素基、又は、置換基を有していてもよい炭素数６～１０の芳香族炭化水素基を表し、該飽和炭化水素基に含まれる－ＣＨ₂－は、－Ｏ－、－ＣＯ－又は－Ｎ
Ｒ¹¹－で置き換わっていてもよい。Ｒ¹及びＲ²は、一緒になって窒素原子を含む環を形成してもよく、Ｒ³及びＲ⁴は、一緒になって窒素原子を含む環を形成してもよい。
Ｒ⁶及びＲ⁷は、互いに独立に、水素原子又は炭素数１～６のアルキル基を表す。
Ｒ¹¹は、水素原子、炭素数１～２０の飽和炭化水素基又は炭素数７～１０のアラルキル基を表す。
ただし、式（Ｉ）で表される化合物は、（ｉ）～（vi）の要件のうち少なくとも１つを充足するものとする。
（ｉ）Ｒ¹が、－ＣＯＯＭを有する炭素数１～２０の飽和炭化水素基であり、Ｒ²～Ｒ⁴の
少なくとも１つが、置換基を有していてもよい炭素数６～１０の芳香族炭化水素基であり、且つ１分子中に含まれる－ＣＯＯＭが１個である。
（ii）Ｒ¹及びＲ³が、－ＣＯＯＭを有する炭素数６～１０の芳香族炭化水素基である。
（iii）Ｒ¹が、－ＣＯＯＭを有する炭素数６～１０の芳香族炭化水素基であり、Ｒ³が、
－ＣＯＯＭを有する炭素数１～２０の飽和炭化水素基である。
（iv）Ｒ¹が、－ＣＯＯＭを有する炭素数３～２０の飽和炭化水素基であり、Ｒ³が、－ＣＯＯＭを有する炭素数１～２０の飽和炭化水素基である。
（ｖ）Ｒ¹が置換基を有していてもよい炭素数１～２０の飽和炭化水素基であり、Ｒ²が－ＣＯＯＭを有する炭素数６～１０の芳香族炭化水素基である。
（vi）Ｒ¹及びＲ²が、水素原子又は置換基を有していてもよい炭素数１～２０の飽和炭化水素基であり、Ｒ³及びＲ⁴の少なくとも１つが、－ＣＯＯＭを有する炭素数６～１０の芳香族炭化水素基である。
（ｉ）～（vi）において、Ｍは、水素原子、Ｎａ⁺、Ｋ⁺、又は⁺Ｎ（Ｒ¹²）₄を表し、４つのＲ¹²は同一でも異なってもよい。
Ｒ¹²は、水素原子、炭素数１～２０の飽和炭化水素基又は炭素数７～１０のアラルキル基を表す。］
［２］［１］に記載の化合物、樹脂（Ｂ）、重合性化合物（Ｃ）、及び重合開始剤（Ｄ）を含む着色硬化性樹脂組成物。
［３］［２］に記載の着色硬化性樹脂組成物から形成されるカラーフィルタ。
［４］［３］に記載のカラーフィルタを含む表示装置。 The present invention includes the following inventions.
[1] A compound represented by the formula (I).

[In the formula (I), R ¹ to R ⁴ have a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a substituent independently of each other. It represents an aromatic hydrocarbon group having 6 to 10 carbon atoms, and -CH _2- contained in the saturated hydrocarbon group is -O-, -CO- or -N.
It may be replaced by R ^11- . R ¹ and R ² may be combined to form a ring containing a nitrogen atom, and R ³ and R ⁴ may be combined to form a ring containing a nitrogen atom.
R ⁶ and R ⁷ represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms independently of each other.
R ¹¹ represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
However, the compound represented by the formula (I) shall satisfy at least one of the requirements of (i) to (vi).
(I) R ¹ is a saturated hydrocarbon group having —COM and having 1 to 20 carbon atoms, and at least one of R ² to R ⁴ may have a substituent and has 6 to 10 carbon atoms. It is a group hydrocarbon group and contains one -COOM in one molecule.
(Ii) R ¹ and R ³ are aromatic hydrocarbon groups having -COM and having 6 to 10 carbon atoms.
(Iii) R ¹ is an aromatic hydrocarbon group having —COM and having 6 to 10 carbon atoms, and R ³ is
-It is a saturated hydrocarbon group having 1 to 20 carbon atoms having COM.
(Iv) R ¹ is a saturated hydrocarbon group having −COOM and having 3 to 20 carbon atoms, and R ³ is a saturated hydrocarbon group having −COOM and having 1 to 20 carbon atoms.
(V) R ¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R ² is an aromatic hydrocarbon group having −COMM and having 6 to 10 carbon atoms.
(Vi) R ¹ and R ² are saturated hydrocarbon groups having 1 to 20 carbon atoms which may have a hydrogen atom or a substituent, and at least one of R ³ and R ⁴ is a carbon having -COOM. It is an aromatic hydrocarbon group having a number of 6 to 10.
In (i) to (vi), M represents a hydrogen atom, Na ⁺ , K ⁺ , or ⁺ N (R ¹² ) ₄ , and the four R ^12s may be the same or different.
R ¹² represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms. ]
[2] A color curable resin composition containing the compound according to [1], the resin (B), the polymerizable compound (C), and the polymerization initiator (D).
[3] A color filter formed from the colored curable resin composition according to [2].
[4] A display device including the color filter according to [3].

According to the color curable resin composition containing the compound of the present invention, a color filter having excellent lightness can be formed.

The compound of the present invention is represented by the formula (I). The compound of the present invention also includes its tautomers, stereoisomers and salts thereof. In addition, each component and functional group exemplified below can be used alone or in combination, respectively.

[In the formula (I), R ¹ to R ⁴ have a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a substituent independently of each other. It represents an aromatic hydrocarbon group having 6 to 10 carbon atoms, and -CH _2- contained in the saturated hydrocarbon group is -O-, -CO- or -N.
It may be replaced by R ^11- . R ¹ and R ² may be combined to form a ring containing a nitrogen atom, and R ³ and R ⁴ may be combined to form a ring containing a nitrogen atom.
R ⁶ and R ⁷ represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms independently of each other.
R ¹¹ represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
However, the compound represented by the formula (I) shall satisfy at least one of the requirements of (i) to (vi).
(I) R ¹ is a saturated hydrocarbon group having —COM and having 1 to 20 carbon atoms, and at least one of R ² to R ⁴ may have a substituent and has 6 to 10 carbon atoms. It is a group hydrocarbon group and contains one -COOM in one molecule.
(Ii) R ¹ and R ³ are aromatic hydrocarbon groups having -COM and having 6 to 10 carbon atoms.
(Iii) R ¹ is an aromatic hydrocarbon group having —COM and having 6 to 10 carbon atoms, and R ³ is
-It is a saturated hydrocarbon group having 1 to 20 carbon atoms having COM.
(Iv) R ¹ is a saturated hydrocarbon group having −COOM and having 3 to 20 carbon atoms, and R ³ is a saturated hydrocarbon group having −COOM and having 1 to 20 carbon atoms.
(V) R ¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R ² is an aromatic hydrocarbon group having −COMM and having 6 to 10 carbon atoms.
(Vi) R ¹ and R ² are saturated hydrocarbon groups having 1 to 20 carbon atoms which may have a hydrogen atom or a substituent, and at least one of R ³ and R ⁴ is a carbon having -COOM. It is an aromatic hydrocarbon group having a number of 6 to 10.
In (i) to (vi), M represents a hydrogen atom, Na ⁺ , K ⁺ , or ⁺ N (R ¹² ) ₄ , and the four R ^12s may be the same or different.
R ¹² represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms. ]

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

Substituents that the aromatic hydrocarbon group may have include halogen atoms, ^—R8 , —O.
H, -OR ⁸ , -SO ₃ H ^, -SO ₃ --Z ⁺ , -COMM, -CO ₂ R ⁸ , -SR ⁸ , -SO ₂ R ⁸ , -SO ₃ R ⁸ or -SO ₂ NR ⁹ R ¹⁰ It is preferable that these substituents substitute hydrogen atoms contained in aromatic hydrocarbon groups. Among these, as substituents, -SO ₃ H, -SO ₃ --Z ^{+ and} -SO ₂ NR ⁹ R ¹⁰ are preferable, ^and -SO ₃ --Z ⁺ , -COOM and-
SO ₂ NR ⁹ R ¹⁰ is more preferred. In this case, as −SO ₃ ⁻ Z ⁺ , −SO ₃ ^{− +} N (R ¹¹ ) ₄ is preferable. When -COMM is contained as a substituent in the aromatic hydrocarbon group,
-COOM is preferably bonded to the meta-position or the para-position with respect to the bond. R ¹ ~
When R ⁴ is these groups, from the color curable resin composition of the present invention containing compound (I),
It is possible to form a color filter that generates less foreign matter and has excellent heat resistance.

R ⁸ represents a saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom.
R ⁹ and R ¹⁰ may have hydrogen atoms or substituents independently of each other and have 1 to 2 carbon atoms.
Representing a saturated hydrocarbon group of 0, -CH _2- contained in the saturated aliphatic hydrocarbon group is -O-,
It may be replaced by −CO−, −NH— or ^−NR8 −, and R9 and R10 may be bonded to each other to form a 3- to ^{10 -} membered heterocycle containing a nitrogen atom. ..

Examples of saturated hydrocarbon groups having 1 to 20 carbon atoms in R ¹ to R ⁴ and R ⁸ to R ¹² include, for example.
Linear alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group, dodecyl group, hexadecyl group, icosyl group; isopropyl group, isobutyl Branched chain alkyl group such as group, isopentyl group, neopentyl group, 2-ethylhexyl group; cyclopropyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, tricyclodecyl group and the like having 3 to 20 carbon atoms. An alicyclic saturated hydrocarbon group can be mentioned. The saturated hydrocarbon group preferably has 1 to 10 carbon atoms.
The hydrogen atom contained in the saturated hydrocarbon group in R ¹ to R ⁴ may be substituted with, for example, —COM as a substituent, an aromatic hydrocarbon group having 6 to 10 carbon atoms, or a halogen atom. Further, in the saturated hydrocarbon groups represented by R ¹ to R ⁴ , it is preferable that the hydrogen atom bonded to the terminal carbon atom (primary carbon atom) is substituted with the substituent. As the aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with the hydrogen atom of the saturated hydrocarbon group of R ¹ to R ⁴ , the aromatic hydrocarbon having 6 to 10 carbon atoms in R ¹ to R ⁴ is used. Examples thereof include groups similar to the groups exemplified as the groups.
The hydrogen atom contained in the saturated hydrocarbon group in R ⁹ and R ¹⁰ may be substituted with, for example, a hydroxy group or a halogen atom as a substituent.

Examples of the ring formed by R ¹ and R ² together and the ring formed by R ³ and R ⁴ together include the following. * Represents a bond.

-OR ⁸ includes, for example, an alkyloxy group such as a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group and an icosyloxy group. Can be mentioned.

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

Examples of the -SR ⁸ include an alkylsulfanyl group such as a methylsulfanyl group, an ethylsulfanyl group, a butylsulfanyl group, a hexylsulfanyl group, a decylsulfanyl group and an icosylsulfanyl group.
Examples of the SO ₂ R ⁸ include an alkyl sulfonyl group such as a methyl sulfonyl group, an ethyl sulfonyl group, a butyl sulfonyl group, a hexyl sulfonyl group, a decyl sulfonyl group and an icosyl sulfonyl group.
Examples of SO ₃ R ⁸ include alkyloxysulfonyl groups such as methoxysulfonyl group, ethoxysulfonyl group, propoxysulfonyl group, tert-butoxysulfonyl group, hexyloxysulfonyl group and icosyloxysulfonyl group.

-SO ₂ NR ⁹ R ¹⁰ includes, for example, a sulfamoyl group;
N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N- sec-Butylsulfamoyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N- (1-ethylpropyl) sulfamoyl group, N- (1,1-dimethylpropyl) sulfamoyl group, N- (1,2-dimethylpropyl) sulfamoyl group, N- (2,2-dimethylpropyl) sulfamoyl group, N- (1-methylbutyl) sulfamoyl group, N- (2-methylbutyl) sulfamoyl group, N- (3) -Methylbutyl) sulfamoyl group, N-cyclopentyl sulfamoyl group, N-hexyl sulfamoyl group, N- (1,3-dimethylbutyl) sulfamoyl group, N- (3,3-dimethylbutyl) sulfamoyl group, N- Heptyl sulfamoyl group, N- (1-methylhexyl) sulfamoyl group, N- (1,4-dimethylpentyl) sulfamoyl group, N-octyl sulfamoyl group, N- (2-ethylhexyl) sulfamoyl group, N- N-1 substituted sulfamoyl group such as (1,5-dimethylhexyl) sulfamoyl group, N- (1,1,2,2-tetramethylbutyl) sulfamoyl group;
N, N-dimethylsulfamoyl group, N, N-ethylmethylsulfamoyl group, N, N-diethylsulfamoyl group, N, N-propylmethylsulfamoyl group, N, N-isopropylmethylsulfa Moyl group, N, N-tert-butylmethylsulfamoyl group, N, N-butylethylsulfamoyl group, N, N-bis (1-methylpropyl) sulfamoyl group, N, N-heptylmethylsulfamoyl Examples thereof include N, N-2-substituted sulfamoyl groups such as groups.

Examples of the alkyl group having 1 to 6 carbon atoms in R ⁶ and R ⁷ include those having 1 to 6 carbon atoms among the alkyl groups mentioned above. Of these, hydrogen atoms are preferable as R ⁶ and R ⁷ .

Examples of the aralkyl group having 7 to 10 carbon atoms in R ¹¹ to R ¹² include a benzyl group, a phenylethyl group, a phenylbutyl group and the like.

Z ⁺ is ⁺ N (R ¹¹ ) ₄ , Na ⁺ or K ⁺ , preferably ⁺ N (R ¹¹ ) ₄ .
As the ⁺ N (R ¹¹ ) ₄ , it is preferable that at least two of the four R ^11s are saturated hydrocarbon groups having 5 to 20 carbon atoms. Further, the total number of carbon atoms of the four R ^11s is preferably 20 to 80, more preferably 20 to 60.

However, the compound represented by the formula (I) satisfies at least one of the requirements of (i) to (vi), and is of (i), (ii), (iv), (v). It is preferable that at least one of the requirements is satisfied.
(I) R ¹ is a saturated hydrocarbon group having —COM and having 1 to 20 carbon atoms, and at least one of R ² to R ⁴ may have a substituent and has 6 to 10 carbon atoms. It is a group hydrocarbon group and contains one -COOM in one molecule.
(Ii) R ¹ and R ³ are aromatic hydrocarbon groups having -COM and having 6 to 10 carbon atoms.
(Iii) R ¹ is an aromatic hydrocarbon group having —COM and having 6 to 10 carbon atoms, and R ³ is
-It is a saturated hydrocarbon group having 1 to 20 carbon atoms having COM.
(Iv) R ¹ is a saturated hydrocarbon group having −COOM and having 3 to 20 carbon atoms, and R ³ is a saturated hydrocarbon group having −COOM and having 1 to 20 carbon atoms.
(V) R ¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R ² is an aromatic hydrocarbon group having −COMM and having 6 to 10 carbon atoms.
(Vi) R ¹ and R ² are saturated hydrocarbon groups having 1 to 20 carbon atoms which may have a hydrogen atom or a substituent, and at least one of R ³ and R ⁴ is a carbon having -COOM. It is an aromatic hydrocarbon group having a number of 6 to 10.
In (i) to (vi), M represents a hydrogen atom, Na ⁺ , K ⁺ , or ⁺ N (R ¹² ) ₄ , and the four R ^12s may be the same or different.
R ¹² represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.

It is particularly preferable that M is a hydrogen atom.
R ¹² is preferably a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or a benzyl group.

In the requirement (i), R ¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms having COM (preferably a saturated hydrocarbon group having 1 to 10 carbon atoms), and at least two of R ² to R ⁴ are. It is preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent. Further, R ¹ is a saturated hydrocarbon group having COM and having 1 to 20 carbon atoms (preferably 1 to 10 carbon atoms).
It is more preferable that R ² and R ³ are aromatic hydrocarbon groups having 6 to 10 carbon atoms which may have a substituent (saturated hydrocarbon group).

In requirement (ii), R ² and R ⁴ are preferably saturated hydrocarbon group groups having 1 to 20 carbon atoms which may have a hydrogen atom or a substituent, and may have a substituent. It is more preferable that it is a saturated hydrocarbon group having 1 to 20 carbon atoms.

In requirement (iv), R ² and R ⁴ are preferably aromatic hydrocarbon groups having 6 to 10 carbon atoms which may have a substituent. Further, R ² is preferably a saturated hydrocarbon group having COOM and having 3 to 20 carbon atoms, and R ¹ and R ² are more preferably saturated hydrocarbon groups having COOM and having 3 to 10 carbon atoms. preferable.

In the requirement (v), further, R ³ is a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R ⁴ is an aromatic hydrocarbon group having COOM and having 6 to 10 carbon atoms. Is preferable.

As the compound (I), a compound represented by the formula (Ia) (hereinafter, may be referred to as “compound (Ia)”) is preferable. Compound (Ia) may be a tautomer thereof.

[In the formula (Ia), R ²¹ to R ²⁴ represent aromatic hydrocarbon groups having 6 to 10 carbon atoms which may have a hydrogen atom, —R ²⁶ or a substituent independently of each other. R ²¹ and R ²² may be combined to form a ring containing a nitrogen atom, and R ²³ and R ²⁴ may be combined to form a ring containing a nitrogen atom.
R ²⁶ represents a saturated hydrocarbon group having 1 to 20 carbon atoms which may have COM.
M represents a hydrogen atom, Na ⁺ , K ⁺ , or ⁺ N (R ¹² ) ₄ , and the four R ^12s may be the same or different.
R ¹² represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
However, the compound represented by the formula (Ia) shall satisfy at least one of the requirements of (ia) to (via).
(Ia) At least one of R ²¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms having COM, and at least one of R ²² to R ²⁴ may have 6 to 10 carbon atoms which may have a substituent. It is an aromatic hydrocarbon group of, and is contained in one molecule-COMM is one.
(Iia) R ²¹ and R ²³ are aromatic hydrocarbon groups having COM and having 6 to 10 carbon atoms. (Iia) R ²¹ is an aromatic hydrocarbon group having 6 to 10 carbon atoms having COOM, and R ²³ is a saturated hydrocarbon group having 1 to 20 carbon atoms having COOM.
(Iva) R ²¹ is a saturated hydrocarbon group having COOM and having 3 to 20 carbon atoms, and R ²³ is a saturated hydrocarbon group having COOM and having 1 to 20 carbon atoms.
(Va) R ²¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R ²² is an aromatic hydrocarbon group having COOM and having 6 to 10 carbon atoms.
(Via) R ²¹ and R ²² are saturated hydrocarbon groups having 1 to 20 carbon atoms which may have a hydrogen atom or a substituent, and R ²³ is an aromatic group having COM and having 6 to 10 carbon atoms. It is a hydrocarbon group. ]

Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms in R ²¹ to R ²⁴ include the same groups as those mentioned as the aromatic hydrocarbon group of R ¹ to R ⁴ . The hydrogen atoms contained in the aromatic hydrocarbon group are -COMM, -SO _3- ^, -SO ₃ H, -SO ₃ ^{--Z1 +} , -SO ₃ R ²⁵ or -S.
It may be replaced with O ₂ NHR ²⁵ . The hydrogen atom contained in the aromatic hydrocarbon group is -CO.
When substituted with OM, -COOM is preferably attached to the meta or para position with respect to the bond.
Z1 ⁺ is ⁺ N (R ²⁷ ) ₄ , Na ⁺ or K ⁺ , preferably ⁺ N (R ²⁷ ) ₄ .
R ²⁵ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
R ²⁷ represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a benzyl group.
As a combination of R ²¹ to R ²⁴ , R ²¹ and R ²³ are hydrogen atoms, and R ²² and R ²⁴ are aromatic hydrocarbon groups having 6 to 10 carbon atoms, which are contained in the aromatic hydrocarbon groups. It is preferable that the hydrogen atom is substituted with −SO ₃ ⁻ , −SO _3H ^, −SO3 _−Z1 ⁺ , −SO ₃ R ²⁶ or −SO ₂ NHR ²⁶ . In a more preferable combination, R ²¹ and R ²³ are hydrogen atoms, R ²² and R ²⁴ are aromatic hydrocarbon groups having 6 to 10 carbon atoms, and the hydrogen atom contained in the aromatic hydrocarbon group is a hydrogen atom. It is replaced with -SO ₃ ^- Z1 ⁺ or -SO ₂ NHR ²⁶ .

As a ring containing a nitrogen atom formed by R ²¹ and R ²² together, and a ring containing a nitrogen atom formed by R ²³ and R ²⁴ together, R ¹ and R ² are combined. The same as the ring to be formed can be mentioned. Of these, aliphatic heterocycles are preferable. Examples of the aliphatic heterocycle include the following. * Represents a bond.

Examples of the saturated hydrocarbon group having 1 to 20 carbon atoms in R ²⁵ to R ²⁷ include the same groups as those mentioned as the saturated hydrocarbon group in R ⁸ to R ¹¹ .
When R ²¹ to R ²⁴ are -R ²⁶ , it is preferable that -R ²⁶ is a methyl group or an ethyl group, respectively. When R ²¹ to R ²⁴ are -R ²⁶ and R ²⁶ has -COOM, the hydrogen atom bonded to the carbon atom (primary carbon atom) at the end of -R ²⁶ is replaced with -COOM. Is preferable.
Further, as R ²⁶ in -SO ₃ R ²⁶ and -SO ₂ NHR ²⁶ , a branched chain alkyl group having 3 to 20 carbon atoms is preferable, a branched chain alkyl group having 6 to 12 carbon atoms is more preferable, and 2- Ethylhexyl groups are more preferred.

As the ⁺ N (R ²⁷ ) ₄ , it is preferable that at least two of the four R ^27s are saturated hydrocarbon groups having 5 to 20 carbon atoms. The total carbon number of the four R ^27s is preferably 20 to 80, more preferably 20 to 60. If ⁺ N (R ²⁷ ) ₄ is present in compound (Ia), R ²⁷ may be the same or different.

However, the compound represented by the formula (Ia) satisfies at least one of the requirements of (ia) to (via), and is of (ia), (iia), (iva), (va). It is preferable that at least one of the requirements is satisfied.
(Ia) R ²¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms having —COM, and at least one of R ²² to R ²⁴ may have a substituent and has 6 to 10 carbon atoms. It is a group hydrocarbon group and contains one -COOM in one molecule.
(Iia) R ²¹ and R ²³ are aromatic hydrocarbon groups having -COM and having 6 to 10 carbon atoms.
(Iia) R ²¹ is an aromatic hydrocarbon group having —COM and having 6 to 10 carbon atoms, and is R ²³ .
Is a saturated hydrocarbon group having —COM and having 1 to 20 carbon atoms.
(Iva) R ²¹ is a saturated hydrocarbon group having −COOM and having 3 to 20 carbon atoms, and R ²³ is a saturated hydrocarbon group having −COOM and having 1 to 20 carbon atoms.
(Va) R ²¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R ²² is an aromatic hydrocarbon group having 6 to 10 carbon atoms having −COMM.
(Via) R ²¹ and R ²² are saturated hydrocarbon groups having 1 to 20 carbon atoms which may have a hydrogen atom or a substituent, and at least one of R ²³ and R ²⁴ is a carbon having -COOM. It is an aromatic hydrocarbon group having a number of 6 to 10.

It is particularly preferable that M is a hydrogen atom.
R ¹² is preferably a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or a benzyl group.

In the requirement (ia), R ²¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms having −COMM (preferably a saturated hydrocarbon group having 1 to 10 carbon atoms), and at least two of R ²² to R ²⁴ are. , It is preferable that it is an aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent. Even if R ²¹ is a saturated hydrocarbon group having 1 to 20 carbon atoms having -COMM (preferably a saturated hydrocarbon group having 1 to 10 carbon atoms) and R ²² and R ²³ have a substituent. It is preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms.

In the requirement (iia), R ²² and R ²⁴ are preferably saturated hydrocarbon groups having 1 to 20 carbon atoms which may have a hydrogen atom or a substituent, and may have a substituent. It is more preferably a saturated hydrocarbon group having 1 to 20 carbon atoms.

In the requirement (iva), R ²² and R ²⁴ are preferably aromatic hydrocarbon groups having 6 to 10 carbon atoms which may have a substituent. Further, R ²² is preferably a saturated hydrocarbon group having −COOM and having 3 to 20 carbon atoms, and R ²¹ and R ²² are saturated hydrocarbon groups having −COOM and having 3 to 10 carbon atoms. Is more preferable.

In the requirement (va), further, R ²³ is a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, and R ²⁴ is an aromatic hydrocarbon having —COM and having 6 to 10 carbon atoms. It is preferably a group.

Further, as the compound (I), a compound represented by the formula (Ib) (hereinafter, may be referred to as “compound (Ib)”) is also preferable. Compound (Ib) may be a tautomer thereof.

[In the formula (Ib), R ³¹ and R ³² represent saturated hydrocarbon groups having 1 to 10 carbon atoms independently of each other, and the hydrogen atom contained in the saturated hydrocarbon groups of R ³¹ and R ³² is-. It may be substituted with COOM, an aromatic hydrocarbon group having 6 to 10 carbon atoms or a halogen atom, and the hydrogen atom contained in the aromatic hydrocarbon group is substituted with −COMM or an alkoxy group having 1 to 3 carbon atoms. -CH _2- contained in the saturated hydrocarbon groups of R ³¹ and R ³² may be -O-, -CO- or -N.
It may be replaced by R ^11- .
R ³³ and R ³⁴ independently represent −COM, an alkyl group having 1 to 4 carbon atoms, an alkylsulfanyl group having 1 to 4 carbon atoms or an alkylsulfonyl group having 1 to 4 carbon atoms.
R ³¹ and R ³³ may be combined to form a ring containing a nitrogen atom, and R ³² and R ³⁴ may be combined to form a ring containing a nitrogen atom.
p and q represent integers from 0 to 5 independently of each other. When p is 2 or more, the plurality of R ^33s may be the same or different, and when q is 2 or more, the plurality of R ^34s may be the same or different.
R ¹¹ has the same meaning as above.
M represents a hydrogen atom, Na ⁺ , K ⁺ , or ⁺ N (R ¹² ) ₄ , and the four R ^12s may be the same or different.
R ¹² represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
However, the compound represented by the formula (Ib) shall satisfy at least one of the requirements of (ib) to (ivb).
(Ib) R ³¹ is a saturated hydrocarbon group having —COOM and having 1 to 20 carbon atoms, and one —COOM is contained in one molecule.
(Iib) At least one of R ³³ and R ³⁴ is -COMM.
(Iib) R ³¹ is a saturated hydrocarbon group having −COOM and having 1 to 20 carbon atoms, and R ³⁴ is −COOM.
(Ivb) R ³¹ is a saturated hydrocarbon group having −COOM and having 3 to 20 carbon atoms, and R ³² is a saturated hydrocarbon group having −COOM and having 1 to 20 carbon atoms. ]

Examples of the saturated hydrocarbon group having 1 to 10 carbon atoms in R ³¹ and R ³² include a group having 1 to 10 carbon atoms in R ⁸ .
Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent include the same group as in R ¹ . When the saturated hydrocarbon group represented by R ³¹ and R ³² is substituted with -COOM, the hydrogen atom bonded to the terminal carbon atom (primary carbon atom) is substituted with -COOM. Is preferable.
Examples of the alkoxy group having 1 to 3 carbon atoms include a methoxy group, an ethoxy group, a propoxy group and the like.
R ³¹ and R ³² are preferably saturated hydrocarbon groups having 1 to 3 carbon atoms independently of each other.

Examples of the alkyl group having 1 to 4 carbon atoms in R ³³ and R ³⁴ include a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group and the like.
Examples of the alkylsulfanyl group having 1 to 4 carbon atoms in R ³³ and R ³⁴ include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, a butylsulfanyl group, an isopropylsulfanyl group and the like.
Examples of the alkylsulfonyl group having 1 to 4 carbon atoms in R ³³ and R ³⁴ include a methyl sulfonyl group, an ethyl sulfonyl group, a propyl sulfonyl group, a butyl sulfonyl group and an isopropyl sulfonyl group.
As R ³³ and R ³⁴ , —COOM or an alkyl group having 1 to 4 carbon atoms is preferable, and —COOM or a methyl group is more preferable. Further, when R ³³ and R ³⁴ are -COOM, it is preferable that -COOM is bonded to the meta-position or the para-position with respect to the carbon atom bonded to N.

p and q are preferably integers of 0 to 2, preferably 1 or 2.

However, the compound represented by the formula (Ib) preferably satisfies at least one of the requirements of (ib) to (ivb), and at least one of the requirements of (ib), (iib) and (ivb). It is preferable to satisfy one.
(Ib) R ³¹ is a saturated hydrocarbon group having —COOM and having 1 to 20 carbon atoms, and one —COOM is contained in one molecule.
(Iib) At least one of R ³³ and R ³⁴ is -COMM.
(Iib) R ³¹ is a saturated hydrocarbon group having −COOM and having 1 to 20 carbon atoms, and R ³⁴ is −COOM.
(Ivb) R ³¹ is a saturated hydrocarbon group having −COOM and having 3 to 20 carbon atoms, and R ³³ is a saturated hydrocarbon group having −COOM and having 1 to 20 carbon atoms.

It is particularly preferable that M is a hydrogen atom.
R ¹² is preferably a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or a benzyl group.

In requirement (iib), it is preferred that both R ³³ and R ³⁴ are -COMM.

In requirement (ivb), R ³³ is preferably a saturated hydrocarbon group having -COOM and having 3 to 20 carbon atoms, and R ³³ and R ³⁴ are saturated hydrocarbons having -COOM and having 3 to 10 carbon atoms. It is more preferable that it is a group.

Examples of the compound (I) include compounds represented by the formulas (Aa-1) to (Aa-52).

The color curable resin composition of the present invention contains a compound (I) as a colorant (A), a resin (B), a polymerizable compound (C), and a polymerization initiator (D).

In the color-curable resin composition of the present invention, the content of the compound (I) is preferably 0.1 to 20% by mass, more preferably 0.1 to 20% by mass, based on the total solid content of the color-curable resin composition. It is 0.5 to 10% by mass, more preferably 0.5 to 5% by mass.

<Colorant (A)>
The colorant (A) may contain a dye (A1) and a pigment (A2) in addition to the compound (I).

The dye (A1) is not particularly limited, and known dyes can be used, and examples thereof include solvent dyes, acid dyes, direct dyes, and mordant dyes. Examples of dyes include compounds classified by the Color Index (The Society of Dyers and Colorists) as having a hue other than pigments, and known dyes described in dyeing notes (color dyeing company). Be done. According to the chemical structure, azo dyes, cyanine dyes, triphenylmethane dyes, xanthene dyes, phthalocyanine dyes, anthraquinone dyes, naphthoquinone dyes, quinoneimine dyes, methine dyes, azomethine dyes, squarylium dyes, acrydin dyes, styryl dyes, coumarins. Examples thereof include dyes, quinoline dyes and nitro dyes. Of these, organic solvent-soluble dyes are preferable.
The compound (I) is contained in the dye (A1).

Specifically, C.I. I. Solvent Yellow 4 (Hereinafter, the description of CI Solvent Yellow is omitted and only the number is described), 14, 15, 23, 24, 38, 62, 63, 68, 82, 94, 98, 99. 117, 162, 163, 167, 189;
C. I. Solvent Red 45, 49, 111, 125, 130, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 2
18, 222, 227, 230, 245, 247;
C. I. Solvent Orange 2, 7, 11, 15, 26, 56, 77, 86;
C. I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60;
C. I. Solvent Blue 4, 5, 14, 18, 35, 36, 37, 45, 58, 59, 59: 1, 63, 67, 68, 69, 70, 78, 79, 83, 90, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139;
C. I. Solvent Green 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35 and the like. I. Solvent dye,
C. I. Acid Yellow 1, 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112, 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184, 190, 193, 196, 197, 199, 202, 203, 204, 205, 207, 212, 214, 220, 221, 228, 230, 232, 235, 238, 240, 242, 243, 251;
C. I. Acid Red 1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 33, 34, 35, 37, 40, 42, 44, 50, 51, 52, 57, 66, 73, 76, 80, 87, 88, 91, 92, 94, 95, 97, 98, 103, 106, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 155, 158, 160, 172, 176,182,183,195,198,206,211,215,216,217,227,228,249,252,257,258,260,261,266,268,270, 274,277,280,281, 289, 308, 312, 315, 316, 339, 341, 345, 346, 349, 382, 383, 388, 394, 401, 412, 417, 418, 422, 426;
C. I. Acid Orange 6, 7, 8, 10, 12, 26, 50, 51, 52, 56, 62, 63, 64, 74, 75, 94, 95, 107, 108, 169, 173;
C. I. Acid Violet 6B, 7, 9, 15, 16, 17, 19, 21, 23, 24, 25, 30, 34, 38, 49, 72, 102;
C. I. Acid Blue 1,3,5,7,9,11,13,15,17,18,22,23,24,25,26,27,29,34,38,40,41,42,43,45, 48, 51, 54, 59, 60, 62, 70, 72, 74, 75, 78, 80, 82, 83, 86, 87, 88, 90, 90: 1, 91, 92, 93, 93: 1, 96, 99, 100, 102, 103, 104, 108, 109, 110, 112, 113, 117, 119, 120, 123, 126, 127, 129, 130, 131, 138, 140, 142, 143, 147, 150, 151, 154, 158, 161, 166, 167, 168, 170, 171, 175, 182, 183, 184, 187, 192, 199, 203, 204, 205, 210, 213, 229, 234, 236, 242, 243, 256, 259, 267, 269, 278, 280, 285, 290, 296, 315, 324: 1, 335, 340;
C. I. Acid Green 1, 3, 5, 6, 7, 8, 9, 11, 13, 14, 15, 16, 22, 25, 27, 28, 41, 50, 50: 1, 58, 63, 65, 80, C.I. of 104, 105, 106, 109 and the like. I. Acid dye,
C. I. Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129, 136, 138, 141;
C. I. Direct Red 79, 82, 83, 84, 91, 92, 96, 97, 98, 99, 105, 106, 107, 172, 173, 176, 177, 179, 181, 182, 184, 204, 207, 211, 213, 218, 220, 221, 222, 2
32, 233, 234, 241, 243, 246, 250;
C. I. Direct Orange 26, 34, 39, 41, 46, 50, 52, 56, 57, 61, 64, 65, 68, 70, 96, 97, 106, 107;
C. I. Direct Violet 47, 52, 54, 59, 60, 65, 66, 79, 80, 81, 82, 84, 89, 90, 93, 95, 96, 103, 104;
C. I. Direct Blue 1, 2, 3, 6, 8, 15, 22, 25, 28, 29, 40, 41, 42, 47, 52, 55, 57, 71, 76, 77, 78, 80, 81, 84, 85, 86, 90, 93, 94, 95, 97, 98, 99, 100, 101, 106, 107, 108, 109, 113, 114, 115, 117, 119, 120, 137, 149, 150, 153, 155, 156, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 170, 171, 172, 173, 188, 189, 190, 192, 193, 194, 195, 196, 198, 199, 200, 201, 202, 203, 207, 209, 210, 212, 213, 214, 222, 225, 226, 228, 229, 236, 237, 238, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 256, 257, 259, 260, 268, 274, 275, 293;
C. I. Direct Green 25, 27, 31, 32, 34, 37, 63, 65, 66, 67, 68, 69, 72, 77, 79, 82 and the like. I. Direct dye,
C. I. Disperse Yellow 51, 54, 76;
C. I. Disperse Violet 26, 27;
C. I. Disperse Blue 1, 14, 56, 60, etc. I. Disperse dye,
C. I. Basic Red 1, 10;
C. I. Basic Blue 1,3,5,7,9,19,21,22,24,25,26,28,29,40,41,45,47,54,58,59,60,64,65,66, 67, 68, 81, 83, 88, 89;
C. I. Basic Violet 2;
C. I. Basic Red 9;
C. I. Basic Green 1; etc. C.I. I. Basic dye,
C. I. Reactive Yellow 2,76,116;
C. I. Reactive orange 16;
C. I. Reactive Red 36; etc. I. Reactive dye,
C. I. Modant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65;
C. I. Modant tread 1, 2, 3, 4, 9, 11, 12, 14, 17, 18, 19, 22, 23, 24, 25, 26, 27, 29, 30, 32, 33, 36, 37, 38 , 39, 41, 42, 43, 45, 46, 48, 52, 53, 56, 62, 63, 71, 74, 76, 78, 85, 86, 88, 90, 94, 95;
C. I. Modant Orange 3, 4, 5, 8, 12, 13, 14, 20, 21, 23, 24, 28, 29, 32, 34, 35, 36, 37, 42, 43, 47, 48;
C. I. Modant Violet 1, 1: 1, 2, 3, 4, 5, 6, 7, 8, 10, 11, 14, 15, 16, 17, 18, 19, 21, 22, 23, 24, 27, 28 , 30, 31, 32, 33, 36, 37, 39, 40, 41, 44, 45, 47, 48, 49, 53, 58;
C. I. Modant Blue 1,2,3,7,8,9,12,13,15,16,19,20,21,22,23,24,26,30,31,32,39,40,41,43 , 44, 48, 49, 53, 61, 74, 77, 83, 84;
C. I. Modant Green 1, 3, 4, 5, 10, 13, 15, 19, 21, 23, 26, 29, 31, 33, 34, 35, 41, 43, 53, etc. I. Mordant dye,
C. I. Bat Green 1 etc. C.I. I. Vat dyes and the like can be mentioned.
These dyes may be appropriately selected according to the spectral spectrum of the desired color filter.

The content of the compound (I) in the dye (A1) is preferably 1 to 99% by mass, more preferably 30 to 90% by mass, and still more preferably 40 to 40% by mass with respect to the total amount of the dye (A1). It is 80% by mass.

The dye (A1) preferably contains an anthraquinone dye (Ad).

As the anthraquinone dye (Ad), a known substance may be used. Examples of the anthraquinone dye (Ad) include, for example.
C. I. Solvent Yellow 117, 163, 167, 189,
C. I. Solvent Orange 77, 86,
C. I. Solvent Red 111, 143, 145, 146, 150, 151, 155, 168, 169, 172, 175, 181, 207, 222, 227, 230, 245, 247,
C. I. Solvent Violet 11, 13, 14, 26, 31, 36, 37, 38, 45, 47, 48, 51, 59, 60,
C. I. Solvent Blue 14, 18, 35, 36, 45, 58, 59, 59: 1, 63, 68, 69, 78, 79, 83, 94, 97, 98, 100, 101, 102, 104, 105, 111, 112, 122, 128, 132, 136, 139,
C. I. Solvent Green 3, 28, 29, 32, 33,
C. I. Acid Red 80,
C. I. Acid Green 25, 27, 28, 41,
C. I. Acid Violet 34,
C. I. Acid Blue 25, 27, 40, 45, 78, 80, 112,
C. I. Disperse Yellow 51,
C. I. Disperse Violet 26, 27,
C. I. Disperse Blue 1, 14, 56, 60,
C. I. Direct blue 40,
C. I. Modant tread 3, 11,
C. I. Modant Blue 8
And so on. The anthraquinone dye (Ad) is preferably soluble in an organic solvent, and more preferably a blue, violet or red anthraquinone dye.

Among these, as the anthraquinone dye (Ad), a compound represented by the formula (1d) (hereinafter, may be referred to as “compound (1d)”) is preferable.

[In the formula (1d), R ⁹¹ and R ⁹² may independently have a hydrogen atom and a substituent, even if they have an aliphatic hydrocarbon group having 1 to 10 carbon atoms and a substituent. A good alicyclic hydrocarbon group with 3 to 10 carbon atoms, or
Equation (1d')

(In the formula (1d'), R ⁹³ is an alkyl group having 1 to 6 carbon atoms, a halogen atom, −SO _3H , −
Represents CO ₂ H, -CO ₂ R ⁹⁴ , -NHCOR ⁹⁴ , -SO ₃ R ⁹⁴ or -SO ₂ NR ⁹⁴ R ⁹⁵ .
R ⁹⁴ represents an aliphatic hydrocarbon group having 1 to 10 carbon atoms or an alicyclic hydrocarbon group having 3 to 10 carbon atoms, and a hydrogen atom contained in the aliphatic hydrocarbon group or an alicyclic hydrocarbon group. May be substituted with a halogen atom, a hydroxy group or an amino group.
R ⁹⁵ represents a hydrogen atom and a saturated hydrocarbon group having 1 to 10 carbon atoms.
r represents an integer from 0 to 5. When r is 2 or more, a plurality of R ^93s may be the same or different.
X ⁹¹ represents a single bond or an alkanediyl group having 1 to 6 carbon atoms. )
Represents a group represented by. ]

If compound (1d) has —SO _3H and / or —CO 2H, _they may form salts (eg, Na salt or K salt).

In R ⁹¹ and R ⁹² , R ⁹⁴ and R ⁹⁵ , examples of the aliphatic hydrocarbon group having 1 to 10 carbon atoms include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group and a heptyl group. Examples thereof include an octyl group, a nonyl group, a decyl group, an isopropyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an isopentyl group, a neopentyl group and a 2-ethylhexyl group.
Examples of the substituent that these aliphatic hydrocarbon groups may have include a hydroxy group, a halogen atom, an amino group and the like, and a hydroxy group or a halogen atom is preferable.

Examples of the alicyclic hydrocarbon group having 3 to 10 carbon atoms represented by R ⁹¹ , R ⁹² and R ⁹⁴ include a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group and a tricyclodecyl group. Can be mentioned.
Examples of the substituent that these alicyclic hydrocarbon groups may have include a hydroxy group, a halogen atom, an amino group and the like, and a hydroxy group or a halogen atom is preferable.

Examples of the alkyl group having 1 to 6 carbon atoms represented by R ⁹³ include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, an isopropyl group, an isobutyl group, a sec-butyl group and a tert-. Examples thereof include a butyl group, an isopentyl group, and a neopentyl group.

-CO ₂ R ⁹⁴ includes a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a hexyloxycarbonyl group, an icosyloxycarbonyl group and the like.

Examples of NHCOR ⁹⁴ include N-acetylamino group, N-propanoylamino group, N-butyrylamino group, N-isobutyrylamino group and N-pivaloylamino group.

-SO ₃ R ⁹⁴ includes a methoxysulfonyl group, an ethoxysulfonyl group, a propoxysulfonyl group, a tert-butoxysulfonyl group, a hexyloxysulfonyl group, an icosyloxysulfonyl group and the like.

-SO ₂ NR ⁹⁴ R ⁹⁵ includes N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N-sec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N- (1-ethylpropyl) sulfamoyl group, N- ( 1,1-dimethylpropyl) sulfamoyl group, N- (1,2-dimethylpropyl) sulfamoyl group, N- (2,2-dimethylpropyl) sulfamoyl group, N- (1-methylbutyl) sulfamoyl group, N- (2) -Methylbutyl) sulfamoyl group, N- (3-methylbutyl) sulfamoyl group, N-cyclopentyl sulfamoyl group, N-cyclohexylsulfamoyl group, N-hexylsulfamoyl group, N- (1,3-dimethylbutyl) Sulfamoyl group, N- (3,3-dimethylbutyl) sulfamoyl group, N-heptyl sulfamoyl group, N- (1-methylhexyl) sulfamoyl group, N- (1,4-dimethylpentyl) sulfamoyl group, N- Octylsulfamoyl group, N- (2-ethylhexyl) sulfamoyl group, N- (1,5-dimethyl) hexylsulfamoyl group, N- (1,1,2,2-tetramethylbutyl) sulfamoyl group, N -N-1 substituted sulfamoyl group such as (5-aminopentyl) sulfamoyl group; N, N-dimethylsulfamoyl group, N, N-ethylmethylsulfamoyl group, N, N-diethylsulfamoyl group, N , N-propylmethylsulfamoyl group, N, N-isopropylmethylsulfamoyl group, N, N-tert-butylmethylsulfamoyl group, N, N-butylethylsulfamoyl group, N, N-bis Examples thereof include N, N-2-substituted sulfamoyl groups such as (1-methylpropyl) sulfamoyl group and N, N-heptylmethylsulfamoyl group.

In X ⁹¹ , the alkanediyl group having 1 to 6 carbon atoms includes a methylene group, an ethylene group, a propane-1,3-diyl group, a propane-1,2-diyl group, a butane-1,4-diyl group and a pentane. -1,5-diyl group, hexane-1,6-diyl group, ethane-1,1-diyl group, butane-1,3-diyl group, 2-methylpropane-1,3-diyl group, 2-methyl Examples thereof include a propane-1,2-diyl group, a pentane-1,4-diyl group, a 2-methylbutane-1,4-diyl group and the like.

As R ⁹³ , an alkyl group having 1 to 5 carbon atoms which may have a hydroxyl group, -SO ₃ R ⁹⁴ , -S
O ₂ NR ⁹⁴ R ⁹⁵ is preferred, —SO ₂ NR ⁹⁴ R ⁹⁵ is more preferred, —SO ₂ NHR ⁹⁴ is even more preferred (in each formula, R ⁹⁴ and R ⁹⁵ are the same as defined above).

Examples of the compound (1d) include compounds represented by the formulas (3-1) to (3-11).

The anthraquinone dye (Ad) is a compound represented by the formula (1d), wherein R ⁹¹ and R ⁹² have a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, and a phenyl group which may have a halogen atom. And a compound which is any of the groups represented by the formula (1d') is preferable, and the compound represented by the formula (3-4) and the formula (3-11) is more preferable.

When the anthraquinone dye (Ad) is contained, the content thereof is preferably 1 to 99% by mass, more preferably 10 to 70% by mass, and further preferably 20 to 60% by mass with respect to the total amount of the dye (A1). It is mass%.

As the pigment (A2), known pigments can be used without particular limitation, and examples thereof include pigments classified as pigments in the Color Index (published by The Society of Dyers and Colorists).
Examples of the pigment include C.I. I. Pigment Yellow 1, 3, 12, 13, 14, 15
, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173. , 194, 214 and other yellow pigments;
C. I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and other orange pigments;
C. I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265 and other red pigments;
C. I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60 and other blue pigments; C.I. I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other violet pigments;
C. I. Pigment Green 7, 36, 58 and other green pigments;
C. I. Pigment brown 23, 25 and other brown pigments;
C. I. Examples thereof include black pigments such as Pigment Black 1 and 7.

As the pigment, C.I. I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60 and other blue pigments; C.I. I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other violet color pigments are preferred. I. Pigment Blue 15: 3, 15: 6 and C.I. I. Pigment Violet 23 is more preferred, C.I. I. Pigment Blue 15: 6 is even more preferred. By including the above pigment, it is easy to optimize the transmission spectrum, and the light resistance and chemical resistance of the color filter are improved.

If necessary, the pigment is treated with a rosin, a surface treatment using a pigment derivative having an acidic group or a basic group introduced therein, a graft treatment on the pigment surface with a polymer compound or the like, and atomization by a sulfuric acid atomization method or the like. Treatment, cleaning treatment with an organic solvent or water for removing impurities, removal treatment of ionic impurities by an ion exchange method, or the like may be performed.
The pigment preferably has a uniform particle size. By carrying out the dispersion treatment by containing a pigment dispersant, it is possible to obtain a pigment dispersion liquid in which the pigment is uniformly dispersed in the solution.

Examples of the pigment dispersant include cationic, anionic, nonionic, amphoteric, polyester, polyamine, and acrylic surfactants. These pigment dispersants may be used alone or in combination of two or more. Pigment dispersants include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Floren (manufactured by Kyoeisha Chemical Co., Ltd.), Solsperse (manufactured by Geneca Co., Ltd.), EFKA (manufactured by CIBA), and Ajinomoto Fine. Examples include (manufactured by Techno Co., Ltd.) and Disperbyk (manufactured by Big Chemie).
When a pigment dispersant is used, the amount used is preferably 1% by mass or more and 100% by mass or less, and more preferably 5% by mass or more and 50% by mass or less, based on the total amount of the pigment (A2). When the amount of the pigment dispersant used is in the above range, a pigment dispersion liquid in a uniformly dispersed state tends to be obtained.

The content ratio (dye (A1) / pigment (A2)) of the dye (A1) and the pigment (A2) in the colorant (A) is usually 1/99 to 99/1 on a mass basis, which is preferable. Is 3/97 to 40/60, more preferably 5/95 to 30/70.

The content of the colorant (A) is preferably 5 to 60% by mass, more preferably 8 to 55% by mass, and further preferably 10 to 50% by mass with respect to the total amount of solid content. When the content of the colorant (A) is within the above range, the color density when used as a color filter is sufficient, and a required amount of a resin or a polymerizable compound can be contained in the composition. A pattern with sufficient target strength can be formed. Here, the "total amount of solid content" in the present specification means an amount obtained by subtracting the content of the solvent from the total amount of the colored curable resin composition. The total amount of solid content and the content of each component relative to the total amount of solid content can be measured by a known analytical means such as, for example, liquid chromatography or gas chromatography.

<Resin (B)>
The resin (B) is not particularly limited, but is preferably an alkali-soluble resin. Examples of the resin (B) include the following resins [K1] to [K6].
Resin [K1]; a structural unit derived from at least one (a) selected from the group consisting of unsaturated carboxylic acids and unsaturated carboxylic acid anhydrides (hereinafter, may be referred to as “(a)”), and 2 carbon atoms. A copolymer having a cyclic ether structure of ~ 4 and a structural unit derived from a monomer (b) having an ethylenically unsaturated bond (hereinafter, may be referred to as “(b)”);
Resin [K2]; Structural unit derived from (a), structural unit derived from (b), and monomer (c) copolymerizable with (a) (however, (a) and (b) are Different.) Copolymer having a structural unit derived from (hereinafter sometimes referred to as “(c)”);
Resin [K3]; a copolymer having a structural unit derived from (a) and a structural unit derived from (c);
Resin [K4]; A copolymer having a structural unit derived from (a) with (b) added and a structural unit derived from (c);
Resin [K5]; A copolymer having a structural unit obtained by adding (a) to a structural unit derived from (b) and a structural unit derived from (c);
Resin [K6]; A copolymer having a structural unit derived from (c) and a structural unit obtained by adding (a) to the structural unit derived from (b) and further adding a carboxylic acid 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, 1,4-cyclohexendicarboxylic 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] Bicyclounsaturated compounds containing a carboxy group such as hept-2-ene and 5-carboxy-6-ethylbicyclo [2.2.1] hept-2-ene;
Maleic anhydride, Citraconic acid anhydride, Itaconic acid anhydride, 3-Vinylphthalic acid anhydride, 4-Vinylphthalic acid anhydride, 3,4,5,6-Tetrahydrophthalic acid 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] esters of divalent or higher polyvalent carboxylic acids such as succinic acid mono [2- (meth) acryloyloxyethyl] and phthalic acid mono [2- (meth) acryloyloxyethyl]. Kind;
Examples thereof include unsaturated acrylates containing a hydroxy group and a carboxy group in the same molecule, such as α- (hydroxymethyl) acrylic acid.
Of these, acrylic acid, methacrylic acid, maleic anhydride and the like are preferable from the viewpoint of copolymerizability and solubility of the obtained resin in an alkaline aqueous solution.

(B) is, for example, a polymerizable compound having a cyclic ether structure having 2 to 4 carbon atoms (for example, at least one selected from the group consisting of an oxylan ring, an oxetane ring and a tetrahydrofuran ring) and an ethylenically unsaturated bond. Say. (B) is a cyclic ether having 2 to 4 carbon atoms and (
A monomer having a meta) acryloyloxy group is preferable.
In addition, in this specification, "(meth) acrylic acid" represents at least one kind selected from the group consisting of acrylic acid and methacrylic acid. Notations such as "(meth) acryloyl" and "(meth) acrylate" have the same meaning.

Examples of (b) include a monomer (b1) having an oxylanyl group and an ethylenically unsaturated bond (hereinafter sometimes referred to as “(b1)”), and a single having an oxetanyl group and an ethylenically unsaturated bond. A metric (b2) (hereinafter sometimes referred to as "(b2)"), a monomer having a tetrahydrofuryl group and an ethylenically unsaturated bond (b3) (hereinafter sometimes referred to as "(b3)"), etc. 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)”). There is), a monomer (b1-2) having an epoxidized structure of an alicyclic unsaturated hydrocarbon (hereinafter, may be referred to as “(b1-2)”).

Examples of (b1-1) include glycidyl (meth) acrylate, β-methylglycidyl (meth) acrylate, β-ethylglycidyl (meth) acrylate, glycidyl vinyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, and p. -Vinylbenzyl glycidyl ether, α-methyl-o-vinylbenzyl glycidyl ether, α-methyl-m-vinylbenzyl glycidyl ether, α-methyl-p-vinylbenzyl glycidyl ether, 2,3-bis (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 (Glysidyloxymethyl) styrene and the like can be mentioned.

Examples of (b1-2) include vinylcyclohexene monooxide, 1,2-epoxy-4-vinylcyclohexane (for example, seroxide 2000; manufactured by Daicel Co., Ltd.), and 3,4-epoxycyclohexylmethyl (meth) acrylate (for example,). Cyclomer A400; manufactured by Dycel Co., Ltd.), 3,4-epoxycyclohexylmethyl (meth) acrylate (for example, Cyclomer M100; manufactured by Dycel Co., Ltd.), a compound represented by the formula (BI) and the formula (BII). Examples thereof include compounds represented by.

[In the formula (BI) and the formula (BII ^{), Ra 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. You may.
X ^a and X ^b represent a single bond, * -R ^{c-, * -R c-O-, * -R c-S- or * -R c - NH- .}
R ^c represents an alkanediyl group having 1 to 6 carbon atoms.
* Represents a bond with O. ]

Examples of the alkyl group having 1 to 4 carbon atoms include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, a tert-butyl group and the like.
Alkyl groups in which the hydrogen atom is substituted with hydroxy include hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group, 1-hydroxypropyl group, 2-hydroxypropyl group, 3-hydroxypropyl group and 1-hydroxy. Examples thereof include -1-methylethyl group, 2-hydroxy-1-methylethyl group, 1-hydroxybutyl group, 2-hydroxybutyl group, 3-hydroxybutyl group, 4-hydroxybutyl group and the like.
Examples of R ^a and R ^b include a hydrogen atom, a methyl group, a hydroxymethyl group, a 1-hydroxyethyl group and a 2-hydroxyethyl group, and more preferably a hydrogen atom and a methyl group.

The alkanediyl group includes a methylene group, an ethylene group, a propane-1,2-diyl group, a propane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,5-diyl group, and a hexane-. Examples include 1,6-diyl group.
As X ^a and X ^b , preferably a single bond, a methylene group, an ethylene group, * -CH ₂ -O-
And * -CH ₂ CH ₂ -O-, more preferably a single bond, * -CH ₂ CH ₂ -O- (* represents a bond with O).

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

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

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

As (b2), a monomer having an oxetanyl group and a (meth) acryloyloxy group is more preferable. Examples of (b2) include 3-methyl-3-methacrylloyloxymethyloxetane, 3-methyl-3-acryloyloxymethyloxetane, 3-ethyl-3-methacryloyloxymethyloxetane, and 3-ethyl-3-acryloyloxymethyloxetane. , 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, Viscort V # 150, manufactured by Osaka Organic Chemical Industry Co., Ltd.), tetrahydrofurfuryl methacrylate and the like.

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

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 ] Deccan-8
-Il (meth) acrylate (in the art, it is commonly referred to as "dicyclopentanyl (meth) acrylate" and may also be referred to as "tricyclodecyl (meth) acrylate"), tricyclo [. 5.2.1.0 ^2,6 ] Decen-8-yl (meth)
Acrylate (in the art, commonly referred to as "dicyclopentenyl (meth) acrylate"), dicyclopentanyloxyethyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, allyl. (Meta) acrylic acid esters such as (meth) acrylate, propargyl (meth) acrylate, phenyl (meth) acrylate, naphthyl (meth) acrylate, and benzyl (meth) acrylate;
Hydroxy group-containing (meth) acrylic acid esters such as 2-hydroxyethyl (meth) acrylate and 2-hydroxypropyl (meth) acrylate;
Dicarboxylic acid diesters such as diethyl maleate, diethyl fumarate, diethyl itaconic acid;
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-en, 5,
6-Dimethoxybicyclo [2.2.1] hept-2-ene, 5,6-diethoxybicyclo [2.2.1] hept-2-ene, 5-hydroxy-5-methylbicyclo [2.2. 1] Hept-2-ene, 5-hydroxy-5-ethylbicyclo [2.2.1] hept-2-ene, 5-hydroxymethyl-5-methylbicyclo [2.2.1] hept-2-ene , 5-tert-Butoxycarbonylbicyclo [2.2.1] hept-2-ene, 5-cyclohexyloxycarbonylbicyclo [2.2.1] hept-2-ene, 5-phenoxycarbonylbicyclo [2.2. 1] Hept-2-ene, 5,6-bis (tert-butoxycarbonyl) bicyclo [2.2.1] Hept-2-ene, 5,6-bis (cyclohexyloxycarbonyl) bicyclo [2.2.1] ] Bicyclounsaturated compounds such as hept-2-ene;
N-Phenylmaleimide, N-Cyclohexylmaleimide, N-benzylmaleimide, N-succinimidyl-3-maleimidebenzoate, N-succinimidyl-4-maleimidebutyrate, N-succinimidyl-6-maleimide caproate, N-succinimidyl-3 -Dicarbonylimide derivatives such as maleimide propionate, N- (9-acridinyl) maleimide;
Styrene, α-methylstyrene, m-methylstyrene, p-methylstyrene, vinyltoluene, 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 these, styrene, vinyltoluene, N-phenylmaleimide, N-cyclohexylmaleimide, N-benzylmaleimide, bicyclo [2.2.1] hept-2-ene and the like are selected from the viewpoint of copolymerization reactivity and heat resistance. preferable.

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

The resin [K1] is described in, for example, the method described in the document "Experimental Method for Polymer Synthesis" (written by Takayuki Otsu, Kagaku-Dojin Co., Ltd., 1st edition, 1st printing, published on March 1, 1972) and the relevant document. 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 with nitrogen to create a deoxidized atmosphere, and the mixture is stirred. Examples thereof include heating and heat retention methods. The polymerization initiator, solvent and the like used here are not particularly limited, and those usually used in the art can be used. For example, as the polymerization initiator, an azo compound (2,2'-azobisisobutyronitrile, 2,2'-azobis (2,4-dimethylvaleronitrile), etc.) or an organic peroxide (benzoyl peroxide, etc.) As the solvent, any solvent may be used as long as it dissolves each monomer, and examples of the solvent (E) of the colored curable resin composition of the present invention include a solvent described later.

The obtained copolymer may be used as it is after the reaction, or a concentrated or diluted solution may be used, or it may be taken out as a solid (powder) by a method such as reprecipitation. You may use the one. In particular, by using the solvent contained in the color-curable resin composition of the present invention as a solvent during this polymerization, the solution after the reaction can be used as it is for the preparation of the color-curable resin composition of the present invention. Therefore, the manufacturing process of the colored curable resin composition of the present invention can be simplified.

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

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

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

The resin [K4] is a carboxylic acid and / or a carboxylic acid anhydride having the cyclic ether having 2 to 4 carbon atoms of (b) obtained by obtaining a copolymer of (a) and (c). It can be manufactured by adding to.
First, the copolymer of (a) and (c) is produced in the same manner as the method described as the method for producing the resin [K1]. In this case, the ratio of the structural units derived from each is preferably the same as that mentioned in the resin [K3].

Next, the cyclic ether having 2 to 4 carbon atoms of (b) is reacted with a part of the carboxylic acid and / or the carboxylic acid anhydride derived from (a) in the copolymer.
Following the production of the copolymer of (a) and (c), the atmosphere in the flask was replaced with air from nitrogen, and (b) a reaction catalyst of carboxylic acid or carboxylic acid anhydride and cyclic ether (for example, Tris (for example, Tris) Resin [K4] can be produced by putting (dimethylaminomethyl) phenol etc.) and a polymerization inhibitor (for example, hydroquinone etc.) in a flask and reacting at 60 to 130 ° C. for 1 to 10 hours, for example. can.
The amount of (b) used is preferably 5 to 80 mol, more preferably 10 to 75 mol, based on 100 mol of (a). Within this range, the storage stability of the colored curable resin composition, the developability when forming a pattern, and the solvent resistance and heat resistance of the obtained pattern,
The balance between mechanical strength and sensitivity tends to be good. Since the reactivity of the cyclic ether is high and the unreacted (b) is unlikely to remain, (b1) is preferable as the (b) used for the resin [K4], 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, the reaction temperature and the time can be appropriately adjusted in consideration of the production equipment, the calorific value due to the polymerization and the like. As with the polymerization conditions, the charging method and the reaction temperature can be appropriately adjusted in consideration of the production equipment, the calorific value due to the polymerization, and the like.

As the first step, the resin [K5] obtains a copolymer of (b) and (c) in the same manner as in the above-mentioned method for producing the resin [K1]. In the same manner as above, the obtained copolymer may be a solution after the reaction as it is, a concentrated or diluted solution may be used, or a solid (powder) may be used by a method such as reprecipitation. You may use the one taken out as.
The ratio of the structural units derived from (b) and (c) is, respectively, with respect to the total number of moles of all the structural units constituting the copolymer.
Structural unit derived from (b); 5 to 95 mol%
Structural unit derived from (c); 5 to 95 mol%
Is preferable
Structural unit derived from (b); 10-90 mol%
Structural unit derived from (c); 10-90 mol%
Is more preferable.

Further, under the same conditions as the method for producing the resin [K4], the cyclic ether derived from (b) of the copolymer of (b) and (c) has the carboxylic acid or carboxylic acid anhydride of (a). The resin [K5] can be obtained by reacting an object.
The amount of (a) used to react with the copolymer is preferably 5 to 80 mol with respect to 100 mol of (b). Since the reactivity of the cyclic ether is high and the unreacted (b) is unlikely to remain, (b1) is preferable as the (b) used for the resin [K5], and (b1-1) is more preferable.

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

Specific examples of the resin (B) include 3,4-epoxycyclohexylmethyl (meth) acrylate / (meth) acrylic acid copolymer and 3,4-epoxytricyclo [5.2.1.0 ^2.6 ] decyl. Resin such as acrylate / (meth) acrylic acid copolymer [K1]; (meth) acrylic acid / 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decyl (meth) acrylate / vinyl toluene Polymers, 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- (meth) acrylic loyloxymethyloxetane / (meth) acrylic acid / styrene Resin such as copolymer [K2]; benzyl (meth) acrylate / (meth) acrylic acid copolymer, resin such as styrene / (meth) acrylic acid copolymer [K3]; benzyl (meth) acrylate / (meth) ) Tricyclodecyl (meth) acrylate / styrene / (meth) acrylic acid copolymer to which glycidyl (meth) acrylate is added, tricyclodecyl (meth) acrylate / (meth) acrylic acid copolymer to which glycidyl (meth) acrylate is added. Resin such as decyl (meth) acrylate / benzyl (meth) acrylate / (meth) acrylic acid copolymer to which glycidyl (meth) acrylate is added; tricyclodecyl (meth) acrylate / glycidyl (meth) Resins such as resins made by reacting (meth) acrylic acid with acrylate copolymers and resins made by reacting tricyclodecyl (meth) acrylate / styrene / glycidyl (meth) acrylate copolymers with (meth) acrylic acid. [K5]; Resin such as a resin obtained by reacting a copolymer of tricyclodecyl (meth) acrylate / glycidyl (meth) acrylate with (meth) acrylic acid and further reacting with tetrahydrophthalic acid anhydride [K6]. And so on.
Among them, as the resin (B), the resin [K1] and the resin [K2] are preferable, and the resin [K2] is particularly 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 even more preferably 5,000 to 30,000. .. When the molecular weight is within the above range, the hardness of the color filter is improved, the residual film ratio is high, the solubility of the unexposed portion in the developing solution is good, and the resolution of the coloring 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, and even more preferably 70 to 135 mg-KOH / g in terms of solid content. Here, the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be obtained by titration using, for example, an aqueous potassium hydroxide solution.

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

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

Above all, the polymerizable compound (C) is preferably a polymerizable compound having three or more ethylenically unsaturated bonds. Examples of such polymerizable compounds include trimethylol propantri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, and dipentaerythritol hexa (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, Examples thereof include caprolactone-modified pentaerythritol tetra (meth) acrylate and caprolactone-modified dipentaerythritol hexa (meth) acrylate.
Of these, 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, and more preferably 250 or more and 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, still more preferably 17 to 55% by mass, based on the total amount of solids. be. When the content of the polymerizable compound (C) is within the above range, the residual film ratio at the time of forming the coloring pattern and the chemical resistance of the color filter tend to be improved.

<Polymer Initiator (D)>
The polymerization initiator (D) is not particularly limited as long as it is a compound that can initiate polymerization by generating active radicals, acids and the like by the action of light or heat, and a known polymerization initiator can be used. Examples of the polymerization initiator that generates an active radical include an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound and a biimidazole compound.

The O-acyloxime compound is a compound having a partial structure represented by the formula (d1). Hereinafter, * represents a bond.

Examples of the O-acyloxym compound include N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-on-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane. -1-On-2-imine, N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-on-2-imine, N-acetoxy-1- [9-ethyl-6-] (2-Methylbenzoyl) -9H-carbazole-3-yl] ethane-1-imine, N-acetoxy-1- [9-ethyl-6- {2-methyl-4- (3,3-dimethyl-2,,) 4-Dioxacyclopentanylmethyloxy) benzoyl} -9H-carbazole-3-yl] ethane-1-imine, N-acetoxy-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazole) -3-Il] -3-Cyclopentylpropane-1-imine, N-benzoyloxy-1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazole-3-yl] -3-Cyclopentylpropane- 1-on-2-imine and the like can be mentioned. Commercially available products such as Irgacure OXE01, OXE02 (all manufactured by BASF) and N-1919 (manufactured by ADEKA) may be used. Among them, the O-acyloxym compounds are N-benzoyloxy-1- (4-phenylsulfanylphenyl) butane-1-on-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1. At least one selected from the group consisting of -on-2-imine and N-benzoyloxy-1- (4-phenylsulfanylphenyl) -3-cyclopentylpropane-1-on-2-imine is preferable, and N-benzoyloxy is preferable. -1- (4-Phenylsulfanylphenyl) octane-
1-on-2-imine is more preferred. With these O-acyloxime compounds, there is a tendency to obtain a high-brightness color filter.

The alkylphenone compound is a compound having a partial structure represented by the formula (d2) or a partial structure represented by the formula (d3). In these partial structures, the benzene ring may have a substituent.

Examples of the compound having a partial structure represented by the formula (d2) include 2-methyl-2-morpholino-1- (4-methylsulfanylphenyl) propan-1-one and 2-dimethylamino-1- (4). -Morholinophenyl) -2-benzylbutane-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- [4- (4-morpholinyl) phenyl] butane-1-one And so on. Commercially available products such as Irgacure 369, 907, 379 (all manufactured by BASF) may be used.
Examples of the compound having a partial structure represented by the formula (d3) include 2-hydroxy-2-methyl-1-phenylpropan-1-one and 2-hydroxy-2-methyl-1- [4- (2). -Hydroxyethoxy) phenyl] Propane-1-one, 1-hydroxycyclohexylphenylketone, 2-hydroxy-2-methyl-1- (4-isopropenylphenyl) propan-1-one oligomer, α, α-diethoxy Examples thereof include acetophenone and benzyldimethylketal.
In terms of sensitivity, the alkylphenone compound is preferably a compound having a partial structure represented by the formula (d2).

Examples of the triazine compound include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine and 2,4-bis (trichloromethyl) -6- (4-). Methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6-piperonyl-1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxy) Styryl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4 -Bis (trichloromethyl) -6- [2- (fran-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-) 2-Methylphenyl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine, etc. Can be mentioned.

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

Examples of the biimidazole compound include 2,2'-bis (2-chlorophenyl) -4,4', 5,5'-tetraphenylbiimidazole and 2,2'-bis (2,3-dichlorophenyl)-. 4,4', 5,5'-tetraphenylbiimidazole (see, for example, JP-A-6-75372, JP-A-6-75373, etc.), 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 (tri) Alkoxyphenyl) Biimidazole (see, for example, Japanese Patent Application Laid-Open No. 48-38403, Japanese Patent Application Laid-Open No. 62-174204, etc.), the phenyl group at the 4,4'5,5'-position is substituted with a carboalkoxy group. Examples thereof include imidazole compounds (see, for example, Japanese Patent Laid-Open No. 7-10913).

Further, the polymerization initiator (D) is a benzophenone compound such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether; benzophenone, o-benzoylmethylbenzoate, 4-phenylbenzophenone, 4-benzoyl-. Benzophenone compounds such as 4'-methyldiphenylsulfide, 3,3', 4,4'-tetra (tert-butylperoxycarbonyl) benzophenone, 2,4,6-trimethylbenzophenone; 9,10-phenanthlenquinone, Kinone compounds such as 2-ethylanthraquinone and benzophenone; examples thereof include 10-butyl-2-chloroacrydone, benzyl, methylphenylglycoxylate, and titanosen compounds. These are preferably used in combination with the polymerization initiation aid (D1) (particularly amines) described later.

Examples of the acid generator include 4-hydroxyphenyldimethylsulfonium-p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium-p-toluenesulfonate, and 4-acetoxyphenylmethyl. Onium salts such as benzylsulfonium hexafluoroantimonate, triphenylsulfonium-p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium-p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, and nitrobenzyltosylate. Species, benzointosylates and the like.

As the polymerization initiator (D), a polymerization initiator containing at least one selected from the group consisting of an alkylphenone compound, a triazine compound, an acylphosphine oxide compound, an O-acyloxime compound and a biimidazole compound is preferable, and an O-acyloxy is preferable. A polymerization initiator containing a polymer compound is more preferable.

The content of the polymerization initiator (D) is preferably 0.1 to 30 parts by mass, and more preferably 1 to 20 parts by mass 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 within the above range, the sensitivity tends to be increased and the exposure time tends to be shortened, so that the productivity of the color filter is improved.

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

Examples of the amine compound include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 4 -2-Ethylhexyl dimethylaminobenzoate, N, N-dimethylparatoluidine, 4,4'-bis (dimethylamino) benzophenone (commonly known as Michelers ketone), 4,4'-bis (diethylamino) benzophenone, 4,4'-bis Examples thereof include (ethylmethylamino) benzophenone, and among them, 4,4'-bis (diethylamino) benzophenone is preferable. Commercially available products such as EAB-F (manufactured by Hodogaya Chemical Co., Ltd.) may be used.

Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, and 9,10-di. Examples thereof include butoxyanthracene, 2-ethyl-9,10-dibutoxyanthracene and the like.

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

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

When these polymerization initiation aids (D1) are used, the content thereof is preferably 0.1 to 30 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 preferably 1 to 20 parts by mass. When the amount of the polymerization initiation aid (D1) is within this range, a coloring 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 a solvent usually used in the art can be used. For example, ester solvent (solvent containing -COO- in the molecule and not containing -O-), ether solvent (solvent containing -O- in the molecule and not containing -COO-), ether ester solvent (intramolecular). Solvent containing -COO- and -O-), Ketone solvent (solvent containing -CO- in the molecule and not containing -COO-), alcohol solvent (solvent containing OH in the molecule, -O-,- CO- and -COO-free solvents), aromatic hydrocarbon solvents, amide solvents, dimethylsulfoxide and the like. These solvents may be used alone or in combination of two or more.

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

Examples of the ether solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, and propylene glycol monoethyl ether. , Propylene glycol monopropyl ether, propylene glycol monobutyl ether, 3-methoxy-1-butanol, 3-methoxy-3-methylbutanol, tetrahydrofuran, tetrahydropyran, 1,4-dioxane, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol methyl ethyl Examples thereof include ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, anisole, phenetol and methyl anisol.

Examples of the ether ester solvent include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, and 3-ethoxy. Ethyl propionate, methyl 2-methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-methoxy-2-methylpropionate, Ethyl 2-ethoxy-2-methylpropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, ethylene glycol monomethyl Examples thereof include ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate and diethylene glycol monobutyl ether acetate.

Ketone solvents include 4-hydroxy-4-methyl-2-pentanone, acetone, 2-butanone, 2-heptanone, 3-heptanone, 4-heptanone, 4-methyl-2-pentanone, cyclopentanone, cyclohexanone and isophorone. And so on.

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

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

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

Among the above solvents, an organic solvent having a boiling point of 120 ° C. or higher and 180 ° C. or lower at 1 atm is preferable from the viewpoint of coatability 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 preferred, and propylene glycol monomethyl ether acetate, 4-hydroxy-4-methyl-2-pentanone, propylene glycol monomethyl ether, ethyl lactate and ethyl 3-ethoxypropionate are more preferred.

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 within the above range, the flatness at the time of coating is good, and the color density is not insufficient when the color filter is formed, so that the display characteristics tend to be good. ..

<Leveling agent (F)>
Examples of the leveling agent (F) include a silicone-based surfactant, a fluorine-based surfactant, and a silicone-based surfactant having a fluorine atom. These may have a polymerizable group in the side chain.
Examples of the silicone-based surfactant include a surfactant having a siloxane bond in the molecule. Specifically, Torre Silicone DC3PA, SH7PA, DC11PA, SH21PA, SH28PA, SH29PA, SH30PA, SH8400 (trade name: manufactured by Toray Dow Corning Co., Ltd.), KP321, KP322, KP323, KP324. , KP326, KP340, KP341 (manufactured by Shin-Etsu Chemical Co., Ltd.), TSF400, TSF401, TSF410, TSF4300, TSF4440, TSF4445, TSF-4446, TSF4452, TSF4460 (manufactured by Momentive Performance Materials Japan GK), etc. Can be mentioned.

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 Co., Ltd.), Megafuck (registered trademark) F142D, F171, F172, F173, F177, F183, F554, and F554. R30, RS-718-K (manufactured by DIC Co., Ltd.), Ftop (registered trademark) EF301, EF303, EF351, EF352 (manufactured by Mitsubishi Materials Electronics Co., Ltd.), Surflon (registered trademark) S381, Examples thereof include S382, SC101, SC105 (manufactured by Asahi Glass Co., Ltd.) and E5844 (manufactured by Daikin Fine Chemical Laboratory Co., Ltd.).

Examples of the silicone-based surfactant having a fluorine atom include a surfactant 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).

When the leveling agent (F) is contained, the content thereof is preferably 0.001% by mass or more and 0.2% by mass or less, preferably 0.002% by mass, based on the total amount of the colored curable resin composition. % Or more and 0.1% by mass or less, more preferably 0.01% by mass or more and 0.05% by mass or less. The content of the pigment dispersant is not included in this content. When the content of the leveling agent (F) is within the above range, the flatness of the color filter can be improved.

<Other ingredients>
The colored curable resin composition of the present invention is an additive known in the art such as a filler, other polymer compounds, adhesion promoters, antioxidants, light stabilizers, chain transfer agents and the like, if necessary. May include.

<Manufacturing method of colored curable resin composition>
The color 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 necessary. It can be prepared by mixing the leveling agent (F) and other components.
When the pigment (A2) is used, it is preferable to mix it with a part or all of the solvent (E) in advance and disperse it 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, if necessary, a part or all of the pigment dispersant and the resin (B) may be blended. The desired color-curable resin composition can be prepared by mixing the remaining components with the pigment dispersion liquid thus obtained so as to have a predetermined concentration.
The dye (A1) may be dissolved in a part or all of the solvent (E) in advance to prepare a solution. It is preferable to filter the solution with a filter having a pore size of about 0.01 to 1 μm.
It is preferable to filter the colored curable resin composition after mixing with a filter having a pore size of about 0.01 to 10 μm.

<Manufacturing method of color filter>
Examples of the method for producing a colored pattern from the colored curable resin composition of the present invention include a photolithography method, an inkjet method, a printing method and the like. Above all, the photolithography method is preferable. The photolithography method is a method in which the colored curable resin composition is applied to a substrate and dried to form a colored composition layer, and the colored composition layer is exposed and developed through a photomask. In the photolithography method, a colored coating film which is a cured product of the colored composition layer can be formed by not using a photomask at the time of exposure and / or not developing the photomask. The colored pattern or colored coating film thus formed can be used as the color filter of the present invention.
The film thickness of the color filter to be produced is not particularly limited and can be appropriately adjusted according to the purpose, application and the like. For example, 0.1 to 30 μm, preferably 0.1 to 20 μm, still more preferably 0.5. It is ~ 6 μm.

The substrate includes a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, soda lime glass whose surface is silica-coated, a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate, silicon, or on the substrate. Aluminum, silver, silver / copper / palladium alloy thin films, etc. are formed on the glass. Another color filter layer, resin layer, transistor, circuit and the like may be formed on these substrates.

The formation of each color pixel by the photolithography method can be performed by a known or conventional device or condition. For example, it can be produced as follows.
First, a colored curable resin composition is applied onto a substrate and dried by heating and drying (pre-baking) and / or under reduced pressure to remove volatile components such as a solvent to obtain a smooth colored composition layer.
Examples of the coating method include a spin coating method, a slit coating method, a slit and spin coating method, and the like.
The temperature for heat drying is preferably 30 to 120 ° C, more preferably 50 to 110 ° C. The heating time is preferably 10 seconds to 60 minutes, more preferably 30 seconds to 30 minutes.
When drying under reduced pressure, it is preferable to carry out drying under a pressure of 50 to 150 Pa in a temperature range of 20 to 25 ° C.
The film thickness of the coloring composition layer is not particularly limited, and may be appropriately selected depending on the film thickness of the target color filter.

The coloring composition layer is then exposed via a photomask to form the desired coloring pattern. The pattern on the photomask is not particularly limited, and a pattern according to the intended use is used.
As the light source used for exposure, a light source that generates light having a wavelength of 250 to 450 nm is preferable. For example, light less than 350 nm is cut by using a filter that cuts this wavelength range, and light near 436 nm, 408 nm, and 365 nm is selectively extracted by using a bandpass filter that extracts these wavelength ranges. You may do it. Specific examples thereof include mercury lamps, light emitting diodes, metal halide lamps, halogen lamps and the like.
An exposure device such as a mask aligner and a stepper should be used because it is possible to uniformly irradiate the entire exposed surface with parallel rays and to accurately align the photomask with the substrate on which the coloring composition layer is formed. Is preferable.

A coloring pattern is formed on the substrate by bringing the exposed coloring composition layer into contact with a developing solution for development. By development, the unexposed portion of the colored composition layer is dissolved in a developing solution and removed. As the developing solution, for example, an aqueous solution of an alkaline compound such as potassium hydroxide, sodium hydrogen carbonate, sodium carbonate, or tetramethylammonium hydroxide is preferable. The concentration of these alkaline compounds in the aqueous solution is preferably 0.01 to 10% by mass, more preferably 0.03 to 5% by mass. Further, the developer may contain a surfactant.
The developing method may be any of a paddle method, a dipping method, a spray method and the like. Further, the substrate may be tilted at an arbitrary angle during development.
After development, it is preferable to wash with water.

Further, it is preferable to post-bake the obtained coloring pattern. The post-bake temperature is preferably 150 to 250 ° C, more preferably 160 to 235 ° C. The post-baking time is preferably 1 to 120 minutes, more preferably 10 to 60 minutes.

According to the color curable resin composition of the present invention, it is possible to produce a color filter having particularly excellent brightness. The color filter is useful as a color filter used in a display device (for example, a liquid crystal display device, an organic EL device, electronic paper, etc.) and a solid-state image sensor.

Hereinafter, the present invention will be described in more detail with reference to examples, but the present invention is not limited by the following examples as well as the present invention, and appropriate modifications are made to the extent that it can meet the purposes of the preceding and the following. Of course, it is possible to carry out, and all of them are included in the technical scope of the present invention.
In the following, unless otherwise specified, "part" means "part by mass" and "%" means "% by mass".

In the following examples, the structure of the compound was confirmed by mass spectrometry (LC; Agilent 1200 type, MASS; Agilent LC / MSD type).

[Example 1]

To a flask equipped with a cooling tube and a stirrer, 3 parts of the compound represented by the formula (X) (manufactured by Chugai Kasei), 21 parts of N-methylpyrrolidone and 1.3 parts of potassium hydroxide were added, and the temperature was 1 hour at room temperature. After stirring, 2.3 parts of ethyl acrylate was added and the mixture was stirred at the same temperature for 2 hours. When the obtained reaction solution was added to 105 parts of 2N hydrochloric acid and stirred at room temperature for 30 minutes, crystals were precipitated. The precipitated crystals were separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C. to obtain 3.5 parts of the compound represented by the formula (Aa-1-IM).

Identification of the compound represented by the formula (Aa-1-IM) (mass spectrometry) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 675.3
Exact Mass: 674.3

To a flask equipped with a condenser and a stirrer, 1 part of the compound represented by the formula (Aa-1-IM), 7 parts of methanol and 3.0 parts of an 8% sodium hydroxide aqueous solution were added, and the mixture was added at room temperature for 9 and a half hours. Stirred. When the obtained reaction solution was added to 35 parts of 2N hydrochloric acid and stirred at room temperature for 30 minutes, crystals were precipitated. The precipitated crystals were separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C. to obtain 0.9 parts of the compound represented by the formula (Aa-1).

Identification of the compound represented by the formula (Aa-1) (mass spectrometry) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 647.5
Exact Mass: 646.2

[Example 2]
In a flask equipped with a cooling tube and a stirrer, 1 part of the compound represented by the formula (X) (manufactured by Chugai Kasei), 7 parts of N-methylpyrrolidone, 1.0 part of potassium carbonate and ethyl 4-bromobutyrate 2. 0 parts were added, and the mixture was stirred at 100 ° C. for 7 and a half hours. After allowing to cool, 20 parts of 2N hydrochloric acid was added to the obtained reaction solution, the mixture was extracted twice with 45 parts of chloroform, the chloroform layers were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the mixture was dried under reduced pressure at 60 ° C. to obtain 4.1 parts of a crude compound represented by the formula (Aa-33-IM).

Identification of the compound represented by the formula (Aa-33-IM) (mass spectrometry) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 803.5
Exact Mass: 802.3

To a flask equipped with a condenser and a stirrer, 4.1 parts of the compound represented by the formula (Aa-33-IM), 9.8 parts of methanol and 3.5 parts of an 8% sodium hydroxide aqueous solution were added to room temperature. Was stirred for 6 hours. When the obtained reaction solution was added to 30 parts of 2N hydrochloric acid and stirred at room temperature for 30 minutes, crystals were precipitated. The precipitated crystals were separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C. to obtain 1.0 part of the compound represented by the formula (Aa-33).

Identification of the compound represented by the formula (Aa-33) (mass spectrometry) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 747.5
Exact Mass: 746.3

[Example 3]
To a flask equipped with a cooling tube and a stirrer, add 3 parts of the compound represented by the formula (X) (manufactured by Chugai Kasei), 21 parts of N-methylpyrrolidone and 1.7 parts of tert-butoxypotassium to 30 parts at room temperature. After stirring for minutes, 1.6 parts of 1-bromopropane was added and the mixture was stirred at the same temperature for 1 hour. When the obtained reaction solution was added to 21 parts of 2N hydrochloric acid and stirred at room temperature for 1 hour, crystals were precipitated. The precipitated crystals were separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C. to obtain 3.0 parts of the compound represented by the formula (Aa-8-IM1).

Identification of the compound represented by the formula (Aa-8-IM1) (mass spectrometry) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 617.5
Exact Mass: 616.2

In a flask equipped with a cooling tube and a stirrer, 1 part of the compound represented by the formula (Aa-8-IM1), 7 parts of N-methylpyrrolidone, 0.45 part of potassium carbonate and 0.95 part of ethyl 4-bromobutyrate. Was added, and the mixture was stirred at 100 ° C. for 5 and a half hours. When the obtained reaction solution was added to 35 parts of 2N hydrochloric acid and stirred at room temperature for 30 minutes, crystals were precipitated. The precipitated crystals were separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C. to obtain 1.2 parts of the compound represented by the formula (Aa-8-IM2).

Identification of the compound represented by the formula (Aa-8-IM2) (mass spectrometry) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 731.5
Exact Mass: 730.3

To a flask equipped with a condenser and a stirrer, 1 part of the compound represented by the formula (Aa-8-IM2), 7 parts of methanol and 2.7 parts of an 8% sodium hydroxide aqueous solution were added, and the temperature was 3 and a half hours at room temperature. Stirred. When the obtained reaction solution was added to 21 parts of 2N hydrochloric acid and stirred at room temperature for 30 minutes, crystals were precipitated. The precipitated crystals were separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C. to obtain 0.9 parts of the compound represented by the formula (Aa-8).

Identification of the compound represented by the formula (Aa-8) (mass spectrometry) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 703.5
Exact Mass: 702.3

[Example 4]
In a flask equipped with a cooling tube and a stirrer, 0.5 part of the compound represented by the formula (Aa-1-IM), 3.5 parts of N-methylpyrrolidone, 0.26 part of potassium carbonate and 1-bromopropane 2 .3 parts were added and the mixture was stirred at room temperature for 80 hours. When the obtained reaction solution was added to 70 parts of 2N hydrochloric acid and stirred at room temperature for 30 minutes, crystals were precipitated. The precipitated crystals were separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C. to obtain 0.5 part of the compound represented by the formula (Aa-4-IM2).

Identification of the compound represented by the formula (Aa-4-IM2) (mass spectrometry) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 717.5
Exact Mass: 716.3

To a flask equipped with a condenser and a stirrer, 0.5 part of the compound represented by the formula (Aa-4-IM2), 3.4 parts of methanol and 1.3 parts of an 8% sodium hydroxide aqueous solution were added to room temperature. Was stirred for 2 hours. When the obtained reaction solution was added to 70 parts of 2N hydrochloric acid and stirred at room temperature for 30 minutes, crystals were precipitated. The precipitated crystals were separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C. to obtain 0.4 part of the compound represented by the formula (Aa-4).

Identification of the compound represented by the formula (Aa-4) (mass spectrometry) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 689.5
Exact Mass: 688.3

[Example 5]
In a flask equipped with a cooling tube and a stirrer, 1.5 parts of the compound represented by the formula (X) (manufactured by Chugai Kasei), 10.5 parts of N-methylpyrrolidone, 1.1 parts of potassium carbonate and 4-bromo 0.5 part of ethyl butyrate was added, and the mixture was stirred at 90 ° C. for 4 and a half hours. When the obtained reaction solution was added to 52.5 parts of ion-exchanged water and stirred at room temperature for 30 minutes, crystals were precipitated. The precipitated crystals were separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C. The obtained crude product was purified by silica gel column chromatography (mobile phase: chloroform / methanol-10 / 1) to obtain 0.2 part of the compound represented by the formula (Aa-5-IM).

Identification of the compound represented by the formula (Aa-5-IM) (mass spectrometry) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 689.5
Exact Mass: 688.3

To a flask equipped with a condenser and a stirrer, 0.2 part of the compound represented by the formula (Aa-5-IM), 1.6 parts of methanol and 1.0 part of an 8% sodium hydroxide aqueous solution were added to room temperature. Was stirred for two and a half hours. When the obtained reaction solution was added to 16 parts of 2N hydrochloric acid and stirred at room temperature for 30 minutes, crystals were precipitated. The precipitated crystals were separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C. to obtain 0.2 part of the compound represented by the formula (Aa-5).

Identification of the compound represented by the formula (Aa-5) (mass spectrometry) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 661.5
Exact Mass: 660.3

[Example 6]

In a flask equipped with a cooling tube and a stirrer, 5 parts of 3,6-dichlorosulfofluorescein (manufactured by Chugai Kasei) represented by the formula (XX), 35 parts of N-methylpyrrolidone and 3-amino-4-methylbenzoic acid 12.2 parts of methyl acid acid was added, and the mixture was stirred at 130 ° C. for 7 hours. After allowing to cool, the obtained reaction solution was added to an aqueous solution of 7.5 parts of concentrated hydrochloric acid and 70 parts of ion-exchanged water, and the mixture was stirred at room temperature for 30 minutes, and crystals were precipitated. The precipitated crystals were separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C. to obtain 6.6 parts of the compound represented by the formula (Aa-41-IM).

Identification of the compound represented by the formula (Aa-41-IM) (mass spectrometry) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 663.5
Exact Mass: 662.2

6. In a flask equipped with a condenser and a stirrer, 6 parts of the compound represented by the formula (Aa-41-IM), 42 parts of N-methylpyrrolidone, 5.0 parts of potassium carbonate and 1-bromopropane.
6 parts were added and the mixture was stirred at 90 ° C. for 6 hours. After allowing to cool, the obtained reaction solution was added to 210 parts of ion-exchanged water and stirred at room temperature for 30 minutes, and crystals were precipitated. The precipitated crystals were separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C. to obtain 5.9 parts of the compound represented by the formula (Aa-44-IM).

Identification of the compound represented by the formula (Aa-44-IM) (mass spectrometry) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 747.8
Exact Mass: 746.3

To a flask equipped with a condenser and a stirrer, 3 parts of the compound represented by the formula (Aa-44-IM), 21 parts of methanol and 8.0 parts of an 8% sodium hydroxide aqueous solution were added, and the mixture was stirred at room temperature for 8 hours. did. When the obtained reaction solution was added to 105 parts of 2N hydrochloric acid and stirred at room temperature for 30 minutes, crystals were precipitated. The precipitated crystals were separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C. to obtain 2.5 parts of the compound represented by the formula (Aa-44).

Identification of the compound represented by the formula (Aa-44) (mass spectrometry) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 719.5
Exact Mass: 718.2

[Example 7]

In a flask equipped with a cooling tube and a stirrer, 5 parts of 3,6-dichlorosulfofluorescein (manufactured by Chugai Kasei) represented by the formula (XX), 35 parts of N-methylpyrrolidone and 4-amino-3-methylbenzoic acid 12.2 parts of methyl acid acid was added, and the mixture was stirred at 130 ° C. for 16 hours. After allowing to cool, the obtained reaction solution was added to an aqueous solution of 7.5 parts of concentrated hydrochloric acid and 70 parts of ion-exchanged water, and the mixture was stirred at room temperature for 30 minutes, and crystals were precipitated. The precipitated crystals were separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C. to obtain 6.5 parts of the compound represented by the formula (Aa-45-IM).

Identification of the compound represented by the formula (Aa-45-IM) (mass spectrometry) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 663.8
Exact Mass: 662.2

In a flask equipped with a cooling tube and a stirrer, 6 parts of the compound represented by the formula (Aa-45-IM), 42 parts of N-methylpyrrolidone, 5.0 parts of potassium carbonate and 6.6 parts of 1-bromopropane Was added, and the mixture was stirred at 90 ° C. for 8 hours. After allowing to cool, the obtained reaction solution was added to 210 parts of ion-exchanged water and stirred at room temperature for 30 minutes, and crystals were precipitated. The precipitated crystals were separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C. to obtain 6.0 parts of the compound represented by the formula (Aa-48-IM).

Identification of the compound represented by the formula (Aa-48-IM) (mass spectrometry) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 747.8
Exact Mass: 746.3

To a flask equipped with a condenser and a stirrer, 3 parts of the compound represented by the formula (Aa-48-IM), 21 parts of methanol and 8.0 parts of an 8% sodium hydroxide aqueous solution were added, and the mixture was added at room temperature for 8 and a half hours. Stirred. When the obtained reaction solution was added to 105 parts of 2N hydrochloric acid and stirred at room temperature for 30 minutes, crystals were precipitated. The precipitated crystals were separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C. to obtain 2.0 parts of the compound represented by the formula (Aa-48).

Identification of the compound represented by the formula (Aa-48) (mass spectrometry) Ionization mode = ESI ⁺ : m / z = [M + H] ⁺ 719.5
Exact Mass: 718.2

[Synthesis Example 1]
An appropriate amount of nitrogen was poured into a flask equipped with a reflux condenser, a dropping funnel and a stirrer to replace it with a nitrogen atmosphere, 371 parts of 1-methoxy-2-propyl acetate was added, and the mixture was heated to 85 ° C. with stirring. Then, in the flask, a mixture of 54 parts of acrylic acid, 3,4-epoxytricyclo [5.2.1.0 ^2,6 ] decane-8 or / and 9-yl acrylate (trade name "E-DCPA"). , 225 parts (manufactured by Daicel Co., Ltd.), 81 parts of vinyl toluene (isomer mixture), and 80 parts of 1-methoxy-2-propyl acetate were added dropwise over 4 hours. On the other hand, a solution prepared by dissolving 30 parts of the polymerization initiator 2,2-azobis (2,4-dimethylvaleronitrile) in 160 parts of 1-methoxy-2-propyl acetate was added dropwise over 5 hours. After the dropping of the initiator solution was completed, the mixture was kept at the same temperature for 4 hours, cooled to room temperature, and the viscosity measured with the B-type viscosity (23 ° C.) was 246 mPas. The solid content of the resin (B-1) solution was 37.5% by weight, and the acid value in terms of solid content was 115 mg-KOH / g. The weight average molecular weight Mw of the produced copolymer was 10600, and the molecular weight distribution (Mw / Mn) was 2.01. Resin (B-1)
Has the following structural units.

The polystyrene-equivalent weight average molecular weight (Mw) and number average molecular weight (Mn) of the resin were measured by the GPC method under the following conditions.
Equipment; HLC-8120GPC (manufactured by Tosoh Corporation)
Column; TSK-GELG2000HXL
Column temperature; 40 ° C
Solvent; THF
Flow velocity; 1.0 mL / min
Test solution solid content concentration; 0.001 to 0.01% by mass
Injection volume; 50 μL
Detector; RI
Calibration standard; TSK STANDARD POLYSTYRENE
F-40, F-4, F-288, A-2500, A-500
(Made by Tosoh Corporation)
The ratio (Mw / Mn) of the polystyrene-equivalent weight average molecular weight and the number average molecular weight obtained above was taken as the molecular weight distribution.

[Example 8]
(Preparation of Coloring Curable Resin Composition)
(A) Colorant: C.I. I. Pigment Blue 15: 6 (Pigment) 27 parts Acrylic pigment dispersant 9.5 parts Propylene glycol monomethyl ether acetate 222 parts are mixed and the pigment is sufficiently dispersed using a bead mill, and then
(A) Colorant: Compound represented by the formula (Aa-1) 1.2 parts (A) Colorant: C.I. I. Solvent Blue 45 1.5 parts (B) Resin: Resin B1 (solid content equivalent) 60 parts (C) Polymerizable compound: Dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.) 40 Part (D) Polymerization initiator: N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-on-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 9 parts (F) Leveling Agent: Polyether modified silicone oil (Torre Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.15 parts (E) Solvent: 4-Hydroxy-4-methyl-2-pentanone 156 parts (E) Solvent: Propylene glycol 401 parts of monomethyl ether acetate was mixed to obtain a colored curable resin composition.

[Comparative Example 1]
(A) Colorant: C.I. I. Pigment Blue 15: 6 (Pigment) 29 parts Acrylic pigment dispersant 10.1 parts Propylene glycol monomethyl ether acetate 236 parts are mixed and the pigment is sufficiently dispersed using a bead mill, and then
(A) Colorant: Dye (Aa-x) 1.4 parts (A) Colorant: C.I. I. Solvent Blue 45 1.6 parts (B) Resin: Resin B1 (solid content equivalent) 60 parts (C) Polymerizable compound: Dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd.) 40 parts (D) Polymerization initiator : N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-on-2-imine (Irgacure (registered trademark) OXE 01; manufactured by BASF) 9 parts (F) Leveling agent: Polyether-modified silicone oil (Torre Silicone SH8400: manufactured by Toray Dow Corning Co., Ltd.) 0.15 parts (E) Solvent: 4-hydroxy-4-methyl-2-pentanone 156 parts (E) Solvent: 397 parts of propylene glycol monomethyl ether acetate mixed A colored curable resin composition was obtained.
The dye (Aa-x) is a mixture of compounds represented by the following formulas (A2-2-1) to (A2-2-8).

Examples 9-14, Comparative Example 1
A colored curable resin composition was obtained by performing the same operation as in Example 8 except that the composition was as shown in Table 1.

In Table 1, "A2-1 ¹⁾ " was mixed with an acrylic pigment dispersant and an amount of propylene glycol monomethyl ether acetate described in the column of "E-13 ⁾ " and dispersed in advance.
The “E-1 ²⁾ ” column represents the total content of propylene glycol monomethyl ether acetate.
In Table 1, each component represents the following. Further, the resin (B) represents a mass portion in terms of solid content.
Compound (I): Compound (Aa-1)
Compound (I): Compound (Aa-33)
Compound (I): Compound (Aa-8)
Compound (I): Compound (Aa-4)
Compound (I): Compound (Aa-5)
Compound (I): Compound (Aa-44)
Compound (I): Compound (Aa-48)
Anthraquinone dye (Ad): Ad-1: C.I. I. Solvent Blue 45 (Savinyl Blue RS; manufactured by Clariant)
Pigment (A2): A2-1: C.I. I. Pigment Blue 15: 6
Resin (B): B-1: Resin B1
Polymerizable compound (C): Dipentaerythritol hexaacrylate (Kayarad (registered trademark) DPHA; manufactured by Nippon Kayaku Co., Ltd.)
Polymerization Initiator (D): D-1: N-benzoyloxy-1- (4-phenylsulfanylphenyl) octane-1-on-2-imine (Irgacure® OXE 01; manufactured by BASF; O-acyloxy) Phenyl compound)
Solvent (E): E-1: Propylene glycol monomethyl ether acetate Solvent (E): E-2: 4-Hydroxy-4-methyl-2-pentanone Leveling agent (F): Polyether-modified silicone oil (Tore Silicone SH8400; Made by Toray Dow Corning Co., Ltd.)

The colored curable resin compositions of Examples 8 to 14 and Comparative Example 1 obtained as described above were evaluated.

<Making a coloring pattern>
A colored curable resin composition was applied onto a 5 cm square glass substrate (Eagle 2000; manufactured by Corning Inc.) by a spin coating method, and then prebaked at 100 ° C. for 3 minutes to obtain a colored composition layer. After allowing to cool, the distance between the substrate on which the colored composition layer was formed and the quartz glass photomask was set to 100 μm, and an exposure machine (TME-150RSK; manufactured by Topcon Co., Ltd.) was used under an atmospheric atmosphere at 150 mJ / cm. Light was irradiated with an exposure amount of ² (based on 365 nm). As the photomask, a photomask having a 100 μm line and space pattern formed was used. The colored composition layer after light irradiation is immersed and developed in an aqueous developer containing 0.12% of nonionic surfactant and 0.04% of potassium hydroxide at 24 ° C. for 60 seconds, washed with water, and then in an oven at 230. Post-baking was performed at ° C. for 20 minutes to obtain a coloring pattern.

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

<Saturation evaluation>
The obtained coloring pattern is spectrally measured using a colorimeter (OSP-SP-200; manufactured by Olympus Co., Ltd.), and the xy chromaticity coordinates in the XYZ color system of CIE using the characteristic function of the C light source. (X, y) and the stimulus value Y were measured. The larger the value of Y, the higher the brightness. The results are shown in Table 2.

According to the colored curable resin composition of the example, it was confirmed that the obtained coating film showed high brightness. From this, it can be seen that the colored coating film and the coloring pattern obtained from the colored curable resin composition of the present invention are useful as a high-brightness color filter, and the liquid crystal display device including the color filter is excellent in display characteristics. ..

According to the color curable resin composition of the present invention, a high-brightness color filter can be formed. The color filter is useful as a color filter used in a display device (for example, a liquid crystal display device, an organic EL device, electronic paper, etc.) and a solid-state image sensor.

Claims (5)

A dye composition for a color filter containing a compound represented by the formula (I).

[In the formula (I), R ¹ to R ⁴ have a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a substituent independently of each other. It represents an aromatic hydrocarbon group having 6 to 10 carbon atoms, and -CH _2- contained in the saturated hydrocarbon group may be replaced with -O-, -CO- or -NR ^11- . R ¹ and R ² may be combined to form a ring containing a nitrogen atom, and R ³ and R ⁴ may be combined to form a ring containing a nitrogen atom.
R ⁶ and R ⁷ represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms independently of each other.
R ¹¹ represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms.
However, the compound represented by the formula (I) shall satisfy at least one of the requirements of (i) and (iii) to (vi).
(I) R ¹ is a saturated hydrocarbon group having —COM and having 1 to 20 carbon atoms, and at least one of R ² to R ⁴ may have a substituent and has 6 to 10 carbon atoms. It is a group hydrocarbon group and contains one -COOM in one molecule .
( Iii) R ¹ is an aromatic hydrocarbon group having —COM and having 6 to 10 carbon atoms, and R ³ is a saturated hydrocarbon group having —COM and having 1 to 20 carbon atoms.
(Iv) R ¹ is a saturated hydrocarbon group having −COOM and having 3 to 20 carbon atoms, and R ³ is a saturated hydrocarbon group having −COOM and having 1 to 20 carbon atoms.
(V) R ¹ is a saturated hydrocarbon group having 3 to 20 carbon atoms which may have a substituent, and R ² is an aromatic hydrocarbon group having —COM and having 6 to 10 carbon atoms.
(Vi) R ¹ and R ² are saturated hydrocarbon groups having 1 to 20 carbon atoms which may have a hydrogen atom or a substituent, and at least one of R ³ and R ⁴ is a carbon having -COOM. It is an aromatic hydrocarbon group having a number of 6 to 10.
In (i) and (iii) to (vi), M represents a hydrogen atom, Na ⁺ , K ⁺ , or ⁺ N (R ¹² ) ₄ , and the four R ^12s may be the same or different.
R ¹² represents a hydrogen atom, a saturated hydrocarbon group having 1 to 20 carbon atoms, or an aralkyl group having 7 to 10 carbon atoms. ] A color curable resin composition containing the dye composition for a color filter according to claim 1. The color curing according to claim 2, further comprising one or more selected from the group consisting of the resin (B), the polymerizable compound (C), and the polymerization initiator (D). Sex resin composition. A color filter formed from the colored curable resin composition according to claim 2 or 3. A display device including the color filter according to claim 4.