JP2014208815A - Colored resin composition, color filter, liquid crystal display device, and organic el display device - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a colored resin composition which contains a xanthene-based compound in a dye and is improved in sensitivity without significantly reducing luminance of a pixel to be obtained, and to provide a color filter formed using the colored resin composition, a high-quality liquid crystal display device, and a high-quality organic EL display device.SOLUTION: The colored resin composition contains (A) a dye, (B) a solvent, (C) a binder resin, and (D) a photopolymerization initiator component. The dye (A) contains a xanthene-based compound represented by a specific structural formula (I). The photopolymerization initiator component (D) contains a compound represented by a specific structural formula (II).

Description

  The present invention resides in a colored resin composition, a color filter, a liquid crystal display device, and an organic EL display device.

Flat panel displays such as liquid crystal display devices and organic EL display devices are widely used, and color filters are used for these displays.
Conventionally, as a method for producing a color filter used in a liquid crystal display device or the like, a coating film of a colored radiation-sensitive composition is formed on a substrate or a substrate on which a light-shielding layer having a desired pattern has been previously formed. There is known a method of obtaining pixels of each color by irradiating radiation through a photomask having a pattern (hereinafter referred to as “exposure”), developing and dissolving and removing unexposed portions, and then post-baking. Yes.

Taking into account the trend of energy conservation, color filters are required to have higher brightness and higher contrast.
For the color filter, a colored resin composition using a pigment is mainly used. In order to obtain high brightness and high contrast, for example, in Non-Patent Document 1, the particle diameter of pigment particles is set to 1 of the coloration wavelength. Disclosed is a method of finely dispersing to / 2 or less.

However, when the pigment particles are finely dispersed, cost increases and stability after dispersion become problems.
On the other hand, dyes have been developed as colorants.
For example, in Patent Documents 1 to 3, as a colored resin composition for forming a blue pixel, C.I. I. (Color Index) It is disclosed to use Pigment Blue 15: 6 (B15: 6) and a xanthene dye.

JP 2010-32999 A JP 2010-26334 A JP 2011-28236 A

Kiyoshi Hashizume, “Color Material Association”, December 1967, p608

However, in the colored resin compositions described in Patent Documents 1 to 3, the sensitivity of the colored resin composition is insufficient, and as a result, the pixel formability after development may be insufficient. I found it.
It has also been found that this occurs particularly when the colored resin composition contains a xanthene compound in the dye.

That is, an object of the present invention is to provide a colored resin composition having improved sensitivity without significantly reducing the luminance of a pixel obtained in a colored resin composition containing a xanthene compound in a dye. .
Moreover, this invention makes it a subject to provide the color filter formed using the said colored resin composition, a high quality liquid crystal display device, and an organic electroluminescent display device.

As a result of intensive studies, the present inventors have found that the above problem can be solved by containing a specific photopolymerization initiator, and have completed the present invention.
That is, the gist of the present invention is as follows.

[1] containing (A) a dye, (B) a solvent, (C) a binder resin, and (D) a photopolymerization initiation component,
(A) the dye contains a xanthene compound represented by the following formula (I), and
(D) A colored resin composition, wherein the photopolymerization initiation component contains a compound represented by the following formula (II).

(In the formula (I),
R ^{1 to} R ⁴ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, or an optionally substituted aromatic hydrocarbon having 6 to 18 carbon atoms. Represents a cyclic group.
R ¹ and R ² , and R ³ and R ⁴ may be independently bonded to each other to form a ring, and the ring may have a substituent.
R ⁵ and R ⁶ each independently represent a hydrogen atom, a halogen atom or an alkyl group having 1 to 10 carbon atoms which may have a substituent.
R ⁷ represents an arbitrary substituent.
m represents an integer of 0 to 5. When m is an integer of 2 or more, the plurality of R ⁷ may be the same or different.
p represents an integer of 1 to 4. When p is 2 to 4, the structures in [] containing a plurality of xanthene skeletons may be the same or different.
X ^q− represents an arbitrary q-valent anion.
q represents the integer of 1-4.
n represents an integer of 0 to 4. When n is 2 to 4, the plurality of X ^q− may be the same or different.
When R ^{1 to} R ⁷ are a group containing a sulfonate group or a carboxylate group, or when R ⁷ is a sulfonate group or a carboxylate group, n is 0 and p = 1, otherwise , P = n × q. )

(In the above formula (II),
Z represents an aromatic ring group which may have a substituent.
m represents an integer of 0 to 20.
X is one group selected from the group consisting of —CR ⁹⁴ R ⁹⁵ —, —C (═CR ⁹⁶ R ⁹⁷ ) —, —CR ⁹⁸ ═CR ⁹⁹ — and —C≡C—, or a combination of two or more thereof. Represents a group consisting of
R ^{96 to} R ⁹⁹ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
R ⁹⁴ and R ⁹⁵ , R ¹⁰¹ and R ¹⁰² each independently represents an arbitrary substituent.
R ¹⁰¹ may be bonded to Z to form a ring, and the ring may have a substituent.
R ¹⁰³ represents an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, or an aryl group having 6 to 20 carbon atoms,
R ¹⁰⁴ to R ¹⁰⁹ each independently represents a hydrogen atom, a halogen atom, a nitro group, an alkyl group or an alkoxy group having 1 to 20 carbon atoms having 1 to 6 carbon atoms. )

[2] The content of the compound represented by the formula (II) is 0.4 mass times or more and 30 mass times or less with respect to the total solid content of the dye (A), [ 1].
[3] The colored resin composition according to [1] or [2], further comprising (E) a polymerizable monomer.
[4] The colored resin composition according to any one of [1] to [3], further comprising (F) a pigment.
[5] A color filter having pixels formed using the colored resin composition according to any one of [1] to [4].
[6] A liquid crystal display device comprising the color filter according to [5].
[7] An organic EL display device comprising the color filter according to [5].

According to the present invention, in a colored resin composition containing a xanthene compound (I) in a dye, it is possible to provide a colored resin composition with improved sensitivity without significantly reducing the luminance of the obtained pixel. it can.
Moreover, according to this invention, the color filter which has the pixel formed using the said colored resin composition, the high quality liquid crystal display device and organic electroluminescent display device containing this color filter can be provided.

It is a section schematic diagram showing an example of an organic EL device which has a color filter of the present invention.

Embodiments of the present invention will be described in detail below, but the following description is an example of embodiments of the present invention, and the present invention is not limited to these contents.
In the present invention, “(meth) acryl”, “(meth) acrylate” and the like mean “acryl and / or methacryl”, “acrylate and / or methacrylate” and the like, for example, “(meth) acrylic acid” "Means" acrylic acid and / or methacrylic acid ".

Further, “total solid content” means all components of the colored resin composition of the present invention other than the solvent components described later.
Furthermore, “aromatic ring” means both “aromatic hydrocarbon ring” and “aromatic heterocycle”.
Moreover, terms such as “CI Pigment Green” mean a color index (CI).

<Colored resin composition>
The colored resin composition of the present invention contains (A) a dye, (B) a solvent, (C) a binder resin, and (D) a photopolymerization initiator, and (A) the xanthene represented by the formula (I). Compound (I) (hereinafter referred to as “xanthene compound (I)”) and (D) a photopolymerization initiator represented by formula (II) (hereinafter referred to as “compound (II)”) "), Preferably (E) a polymerizable monomer and (F) a pigment, and may further contain other components.

First, the (A) dye and xanthene compound (I) in the present invention will be described.
[(A) Dye]
<Xanthene compound (I)>
In the colored resin composition of the present invention, the (A) dye contains a xanthene compound (I) represented by the following formula (I).

In formula (I), R ^{1 to} R ⁴ each independently represent a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, or an optionally substituted carbon group having 6 to 6 carbon atoms. 18 aromatic hydrocarbon ring groups are represented.
R ¹ and R ² , and R ³ and R ⁴ may be independently bonded to each other to form a ring, and the ring may have a substituent.

R ⁵ and R ⁶ each independently represents a hydrogen atom, a halogen atom or an alkyl group having 1 to 10 carbon atoms which may have a substituent. R ⁷ represents an arbitrary substituent. m represents an integer of 0 to 5, and when m is an integer of 2 or more, a plurality of R ⁷ may be the same or different.
Moreover, p represents the integer of 1-4. When p is 2 to 4, the structures in [] containing a plurality of xanthene skeletons may be the same or different. X ^q− represents a q-valent anion, and q represents an integer of 1 to 4.
n represents an integer of 0 to 4. When n is 2 to 4, the plurality of X ^q− may be the same or different.
When R ^{1 to} R ⁷ are a group containing a sulfonate group or a carboxylate group, or when R ⁷ is a sulfonate group or a carboxylate group, n is 0 and p = 1, otherwise , P = n × q.

(R ¹ ~R ⁴⁾
R ^{1 to} R ⁴ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, or an optionally substituted aromatic carbon atom having 6 to 18 carbon atoms. Represents a hydrogen ring group.

The alkyl group in R ^{1 to} R ⁴ is a linear, branched or cyclic alkyl group, and the carbon number is usually 1 or more, usually 10 or less, preferably 8 or less, more preferably 5 The following are mentioned.
Specific examples include methyl group, ethyl group, n-propyl group, 2-propyl group, n-butyl group, isobutyl group, tert-butyl group, cyclohexyl group and the like.

The aromatic hydrocarbon ring group in R ^{1 to} R ⁴ may be a single ring or a condensed ring, and is not particularly limited as long as the number of carbon atoms forming the ring is 6 to 14, but for example, Examples thereof include a benzene ring, naphthalene ring, anthracene ring, phenanthrene ring, acenaphthene ring, fluoranthene ring, and fluorene ring having one free valence.
The free valence in the present invention is based on the description of “Organic Chemistry / Biochemical Nomenclature” (Nanedo, published May 20, 1992, translated by Kenzo Hirayama and Kazuo Hirayama, pages 11-12). .

R ¹ and R ² , and R ³ and R ⁴ may be independently bonded to each other to form a ring, and the ring may have a substituent.
The substituent that the alkyl group and aromatic hydrocarbon ring group in R ^{1 to} R ⁴ may have is not particularly limited as long as the effects of the present invention are not impaired, but examples thereof include the following (substituent group W Those described in the section ¹ ) can be mentioned.

(Substituent group W ¹ )
C1-C8 alkyl group, C2-C8 alkenyl group, C1-C8 alkoxy group, C6-C15 aryloxy group, C6-C15 aryl group, C2-C2 9 alkylcarbonyloxy groups, C7-16 arylcarbonyloxy groups, C2-9 alkoxycarbonyl groups, C7-16 aryloxycarbonyl groups, carbamoyl groups, C2-9 alkylcarbamoyl groups Group, arylcarbamoyl group having 7 to 16 carbon atoms, sulfamoyl group, alkylsulfamoyl group having 1 to 8 carbon atoms, arylsulfamoyl group having 6 to 16 carbon atoms, alkylcarbonyl group having 2 to 9 carbon atoms, carbon An arylcarbonyl group having 7 to 16 carbon atoms, an alkylsulfonylamino group having 1 to 8 carbon atoms, an arylsulfonylamino group having 6 to 16 carbon atoms, Mino group, alkylamino group formed by bonding an alkyl group having 1 to 8 carbon atoms, dialkylamino group formed by bonding an alkyl group having 1 to 6 carbon atoms, arylamino group having 6 to 16 carbon atoms, carbon number 6 An arylalkylamino group in which an aryl group having 10 to 10 carbon atoms and an alkyl having 1 to 4 carbon atoms are bonded, an alkylcarbonylamino group having 1 to 8 carbon atoms, an arylcarbonylamino group having 7 to 16 carbon atoms, a trifluoromethyl group, C1-C8 trialkylsilyl group, C1-C8 alkylthio group, C6-C16 arylthio group, hydroxy group, nitro group, cyano group, sulfonate group, sulfo group, sulfo group salt, carboxy Group, carboxylato group, salt of carboxy group, halogen atom such as fluorine atom and chlorine atom.

Specific examples of the aryl group in the substituent group W ¹ include those described as the aromatic hydrocarbon ring group in R ^{1 to} R ⁴ and aromatic heterocyclic groups having 3 to 10 carbon atoms. Examples of the aromatic heterocyclic group include groups having one free valence such as a furan ring, a thiophene ring pyrrole ring, a pyrazole ring, an imidazole ring, and a pyridine ring. The aryl group is a lower alkyl group such as methyl group or ethyl group, a lower alkoxy group such as methoxy group or ethoxy group, nitro group, trifluoromethyl group, cyano group, carbamoyl group, sulfamoyl group, C 1-10. A halogen atom such as an alkylsulfamoyl group substituted with an alkyl group, a fluorine atom, or a chlorine atom may further be included as a substituent.

As the substituent that the alkyl group, the aromatic hydrocarbon ring group, and the ring formed by being connected to each other in R ^{1 to} R ⁴ may have, preferably an alkyl group having 1 to 8 carbon atoms, 8 alkoxy group, phenyl group, tolyl group, alkylcarbonyloxy group having 2 to 9 carbon atoms, carbamoyl group, sulfamoyl group, alkylsulfamoyl group having 1 to 8 carbon atoms, trifluoromethyl group, cyano group, sulfo group And a fluorine atom.

Among these, it is preferable that R < ¹ > -R < ⁴ > is an alkyl group from a soluble viewpoint to a solvent. R ¹ and R ² , and R ³ and R ⁴ are each independently bonded to each other to form an aliphatic hydrocarbon ring (the element constituting the ring may contain an oxygen atom, a sulfur atom, or a nitrogen atom). ) Is included. Preferably, it is a C1-C10 alkyl group which may have a substituent, and more preferably an ethyl group. If the alkyl group has too many carbon atoms, it is preferable from the viewpoint of solubility, but the association between the dyes is inhibited, durability such as heat resistance and light resistance is inferior, and the methyl group is detached from the nitrogen atom. there is a possibility.
On the other hand, from the viewpoint of light resistance, R ^{1 to} R ⁴ are preferably an aromatic hydrocarbon ring group, and may be an aromatic hydrocarbon ring group having 6 to 18 carbon atoms that may have a substituent. More preferred is a phenyl group in which an alkyl group having 1 to 4 carbon atoms is substituted at the 2-position, 6-position, or 2,6-position. When R ^{1 to} R ⁴ are aromatic hydrocarbon ring groups, they are linked to the xanthene skeleton by a conjugated system, so that the light resistance is improved, but the solubility tends to be lowered. Therefore, the aromatic hydrocarbon ring group has increased solubility by having an alkyl group, and particularly in the phenyl group in which the alkyl group having 1 to 4 carbon atoms is substituted at the 2-position, 6-position, or 2,6-position, Since the phenyl group is twisted from the same plane as the xanthene skeleton, the solubility is particularly improved, which is particularly preferable.
R ^{1 to} R ⁴ may be the same or different, but from the viewpoints of solubility, heat resistance, and light resistance, R ^{1 to} R ⁴ may all have a substituent. 1 to 10 alkyl groups, or R ¹ and R ³ are each independently a hydrogen atom or an optionally substituted alkyl group having 1 to 10 carbon atoms, and R ² and R ⁴ are It is preferable that it is a C6-C18 aromatic hydrocarbon ring group which may have a substituent each independently.

(R ⁵ and R ⁶⁾
In the xanthene compound (I), R ⁵ and R ⁶ each independently represent a hydrogen atom, a halogen atom or an optionally substituted alkyl group having 1 to 10 carbon atoms.
The halogen atom in R ⁵ and R ⁶ represents a fluorine atom, a chlorine atom, a bromine atom or an iodine atom. Preferably, they are a chlorine atom and a bromine atom.

Alkyl group for R ⁵ and 10 carbon atoms which may have a substituent in R ⁶ is the same as the alkyl group in R ¹ to R ^4.

Among these, from the viewpoint of color tone, R ⁵ and R ⁶ are preferably hydrogen atoms.

(R ⁷⁾
In the xanthene compound (I), R ⁷ represents an arbitrary substituent.
As an arbitrary substituent in R ⁷ , for example, an alkyl group having 1 to 10 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent, An alkoxy group which may have a substituent, a phenoxy group which may have a substituent, an alkylcarbonyloxy group which may have a substituent, an arylcarbonyloxy which may have a substituent Group, an alkoxycarbonyl group which may have a substituent, an aryloxycarbonyl group which may have a substituent, an amino group, an alkylamino group which may have a substituent, and a substituent An arylamino group which may have a substituent, an alkylcarbonylamino group which may have a substituent, an arylcarbonylamino group which may have a substituent, an alkylsulfo which may have a substituent Ruamino group, arylsulfonylamino group optionally having substituent, carbamoyl group, alkylcarbamoyl group optionally having substituent, arylcarbamoyl group optionally having substituent, sulfamoyl group, substituted Alkylsulfamoyl group which may have a group or arylsulfamoyl group which may have a substituent, hydroxyl group, nitro group, cyano group, sulfonate group, sulfo group, sulfo group salt, carboxy group , Carboxylate group, salt of carboxy group or halogen atom.

Which may have a substituent an alkyl group having 1 to 10 carbon atoms are the same as the alkyl group for R ¹ to R ^4. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, a hydroxyethyl group, a 1,2-dihydroxypropyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-butoxyethyl group, Examples include 2- (2-methoxyethoxy) ethyl group, 2- (2-ethoxyethoxy) ethyl group, 2- (2-butoxyethoxy) ethyl group, benzyl group, phenethyl group and the like.

Aromatic hydrocarbon group having 6 to 18 carbon atoms which may have a substituent are the same as the aromatic hydrocarbon group for R ¹ to R ^4. Specific examples of the aromatic hydrocarbon group include a phenyl group, a p-tolyl group, an m-tolyl group, a p-methoxyphenyl group, a naphthyl group, and an anthracenyl group.
The alkoxy group which may have a substituent is represented by —OR ¹¹ , and R ¹¹ represents an alkyl group having 1 to 10 carbon atoms which may have a substituent. R ¹¹ is the same as the alkyl group in R ^{1 to} R ⁴ . Specific examples of the alkoxy group include methoxy group, ethoxy group, n-propoxy group, n-butoxy group, hydroxyethoxy group, 1,2-dihydroxypropoxy group, 2-methoxyethoxy group, 2-ethoxyethoxy group, 2 -Butoxyethoxy group, 2- (2-methoxyethoxy) ethoxy group, 2- (2-ethoxyethoxy) ethoxy group, 2- (2-butoxyethoxy) ethoxy group, benzyloxy group, phenethyloxy group and the like.

The phenoxy group which may have a substituent has 6 to 18 carbon atoms, and the substituent which the phenoxy group may be substituted is the one described in the section of (Substituent group W ¹ ). Can be mentioned. Specific examples of the phenoxy group include a phenoxy group, a p-tolyloxy group, an m-tolyloxy group, and a p-methoxyphenoxy group.
The alkylcarbonyloxy group which may have a substituent is represented by —O—COR ¹² , and R ¹² represents an alkyl group having 1 to 10 carbon atoms which may have a substituent. R ¹² is the same as the alkyl group in R ^{1 to} R ⁴ . Specific examples of the alkylcarbonyloxy group include an acetoxy group, an ethylcarbonyloxy group, an n-butylcarbonyloxy group, a t-butylcarbonyloxy group, and the like.

The arylcarbonyloxy group which may have a substituent is represented by —O—COR ¹³ , and R ¹³ represents an aryl group having 6 to 15 carbon atoms which may have a substituent. Specific examples of the aryl group include those described as the aromatic hydrocarbon ring group in R ^{1 to} R ⁴ and aromatic heterocyclic groups having 3 to 10 carbon atoms. Examples of the aromatic heterocyclic group include groups having one free valence such as a furan ring, a thiophene ring pyrrole ring, a pyrazole ring, an imidazole ring, and a pyridine ring. The aryl group is a lower alkyl group such as methyl group or ethyl group, a lower alkoxy group such as methoxy group or ethoxy group, nitro group, trifluoromethyl group, cyano group, carbamoyl group, sulfamoyl group, C 1-10. A halogen atom such as an alkylsulfamoyl group substituted with an alkyl group, a fluorine atom, or a chlorine atom may further be included as a substituent. Specific examples of the arylcarbonyloxy group include benzoyloxy group, p-tolylcarbonyloxy group, m-tolylcarbonyloxy group, p-methoxyphenylcarbonyloxy group and the like.

The alkoxycarbonyl group which may have a substituent is represented by —CO ₂ R ¹⁴ , and R ¹⁴ represents an alkyl group having 1 to 10 carbon atoms which may have a substituent. R ¹⁴ is the same as the alkyl group in R ^{1 to} R ⁴ .
Specific examples of the alkoxycarbonyl group include a methoxycarbonyl group, an ethoxycarbonyl group, a phenethyloxycarbonyl group, a 2-ethylhexyloxycarbonyl group, a 2-ethoxyethoxycarbonyl group, and a 2- (2-ethoxyethoxy) ethoxycarbonyl group. Can be mentioned.

The aryloxycarbonyl group which may have a substituent is represented by —CO ₂ R ¹⁵ , and R ¹⁵ represents an aryl group having 6 to 15 carbon atoms which may have a substituent. R ¹⁵ is the same as the aryl group in R ¹³ . Specific examples of the aryloxycarbonyl group include phenoxycarbonyl group, naphthoxycarbonyl group, p-tolyloxycarbonyl group, p-methoxyphenoxycarbonyl group and the like.

The alkylamino group which may have a substituent is represented by —NR ¹⁶ R ¹⁷ , R ¹⁶ represents an alkyl group which may have a substituent, and R ¹⁷ represents a hydrogen atom or a substituent. It represents an alkyl group that may have. The alkyl group is the same as the alkyl group in R ^{1 to} R ⁴ . Specific examples of the alkylamino group include an ethylamino group, a dimethylamino group, a diethylamino group, a dibutylamino group, a di (2-ethoxyethyl) amino group, a diphenethylethylamino group, and a cyclohexylethyl group.

The arylamino group which may have a substituent is represented by —NR ¹⁸ R ¹⁹ , R ¹⁸ represents an aryl group which may have a substituent, and R ¹⁹ represents a hydrogen atom or a substituent. The alkyl group which may have and the aryl group which may have a substituent are represented. The alkyl group is the same as the alkyl group in R ^{1 to} R ⁴ . The aryl group is the same as the aryl group in R ¹³ . Specific examples of the arylamino group include a phenylamino group, a diphenylamino group, a di (p-tolyl) amino group, a di (p-methoxyphenyl) amino group, an ethylphenylamino group, and an n-butylphenylamino group. Can be mentioned.

The alkylcarbonylamino group which may have a substituent is represented by —NH—COR ²⁰ or —N (—COR ²⁰ ) —COR ²¹ , and R ²⁰ and R ²¹ may have a substituent. Represents an alkyl group. The alkyl group is the same as the alkyl group in R ^{1 to} R ⁴ . Specific examples of the alkylcarbonylamino group include acetylamino group, ethyl 2-ethylhexylcarbonylamino group, diacetylamino group and the like.

The arylcarbonylamino group which may have a substituent is represented by —NH—COR ²² or —N (—COR ²² ) —COR ²³ , and R ²² represents an aryl group which may have a substituent. R ²³ represents an alkyl group which may have a substituent or an aryl group which may have a substituent. The alkyl group is the same as the alkyl group in R ^{1 to} R ⁴ . The aryl group is the same as the aryl group in R ¹³ . Specific examples of the arylcarbonylamino group include a benzoylamino group and a dibenzoylamino group.

The alkylsulfonylamino group which may have a substituent is represented by —NH—COR ²⁴ or —N (—COR ²⁴ ) —COR ²⁵ , and R ²⁴ and R ²⁵ may have a substituent. Represents an alkyl group. The alkyl group is the same as the alkyl group in R ^{1 to} R ⁴ . Specific examples of the alkylsulfonylamino group include a methylsulfonylamino group, an ethyl 2-ethylhexylsulfonylamino group, and a dimethylsulfonylamino group.

The arylsulfonylamino group which may have a substituent is represented by —NH—COR ²⁶ or —N (—COR ²⁶ ) —COR ²⁷ , and R ²⁶ represents an aryl group which may have a substituent. R ²⁷ represents an alkyl group which may have a substituent or an aryl group which may have a substituent. The alkyl group is the same as the alkyl group in R ^{1 to} R ⁴ . The aryl group is the same as the aryl group in R ¹³ . Specific examples of the arylsulfonylamino group include p-tolylsulfonylamino group and di-p-tolylsulfonylamino group.

The alkylcarbamoyl group which may have a substituent is represented by —CO—NR ²⁸ R ²⁹ , R ²⁸ represents an alkyl group which may have a substituent, and R ²⁹ represents a hydrogen atom or a substituent. It represents an alkyl group that may have. R ²⁸ and R ²⁹ may be bonded to each other to form a ring, and the ring may have a substituent. Examples of the substituent that the ring may have include those described in the section of (Substituent group W ¹ ). The alkyl group is the same as the alkyl group in R ^{1 to} R ⁴ . Specific examples of the alkylcarbamoyl group include a methylcarbamoyl group, an ethylcarbamoyl group, a phenethylcarbamoyl group, a 2-ethylhexylcarbamoyl group, a 2-ethoxyethylcarbamoyl group, a 2- (2-ethoxyethoxy) ethylcarbamoyl group, and a diethylcarbamoyl group. , Di-n-butylcarbamoyl group, dicyclohexylcarbamoyl group, pyrrolylcarbonyl group and the like.

The arylcarbamoyl group which may have a substituent is represented by —CO—NR ³⁰ R ³¹ , R ³⁰ represents an aryl group which may have a substituent, R ³¹ represents a hydrogen atom, a substituent. The aryl group which may have or the alkyl group which may have a substituent is represented. R ³⁰ and R ³¹ may be bonded to each other to form a ring, and the ring may have a substituent. Examples of the substituent that the ring may have include those described in the section of (Substituent group W ¹ ). The alkyl group is the same as the alkyl group in R ^{1 to} R ⁴ . The aryl group is the same as the aryl group in R ¹³ . Specific examples of the arylcarbamoyl group include phenylcarbamoyl group, naphthylcarbamoyl group, p-tolylcarbamoyl group, p-methoxyphenylcarbamoyl group, ethylphenylcarbamoyl group, n-butylphenylcarbamoyl group, diphenylcarbamoyl group, indolinylcarbonyl Group, 1,2,3,4-tetrahydroquinolinylcarbonyl group and the like.

The optionally substituted alkylsulfamoyl group is represented by —SO ₂ —NR ³² R ³³ , R ³² represents an optionally substituted alkyl group, and R ³³ represents a hydrogen atom or The alkyl group which may have a substituent is represented. R ³² and R ³³ may be bonded to each other to form a ring, and the ring may have a substituent. Examples of the substituent that the ring may have include those described in the section of (Substituent group W ¹ ). The alkyl group is the same as the alkyl group in R ^{1 to} R ⁴ . Specific examples of the alkylsulfamoyl group include methylsulfamoyl group, ethylsulfamoyl group, phenethylsulfamoyl group, 2-ethylhexylsulfamoyl group, 2-ethoxyethylsulfamoyl group, 2- ( 2-ethoxyethoxy) ethylsulfamoyl group, diethylsulfamoyl group, di-n-butylsulfamoyl group, dicyclohexylsulfamoyl group, pyrrolylsulfonyl group and the like.

The arylsulfamoyl group which may have a substituent is represented by —CO—NR ³⁴ R ³⁵ , R ³⁴ is an aryl group which may have a substituent, R ³⁵ is a hydrogen atom, The aryl group which may have a group, or the alkyl group which may have a substituent is represented. R ³⁴ and R ³⁵ may be bonded to each other to form a ring, and the ring may have a substituent. Examples of the substituent that the ring may have include those described in the section of (Substituent group W ¹ ). The alkyl group is the same as the alkyl group in R ^{1 to} R ⁴ . The aryl group is the same as the aryl group in R ¹³ . Specific examples of the arylsulfamoyl group include phenylsulfamoyl group, naphthylsulfamoyl group, p-tolylsulfamoyl group, p-methoxyphenylsulfamoyl group, ethylphenylsulfamoyl group, n- Examples thereof include a butylphenylsulfamoyl group, a diphenylsulfamoyl group, an indolinylsulfonyl group, and a 1,2,3,4-tetrahydroquinolinylsulfonyl group.

Among these, R ⁷ has a sulfonate group, a sulfo group, a salt of a sulfo group, a carboxy group, a carboxylate group, a salt of a carboxy group, an alkoxycarbonyl group that may have a substituent, or a substituent. An optionally substituted aryloxycarbonyl group, an optionally substituted alkylcarbamoyl group, an optionally substituted arylcarbamoyl group, an optionally substituted alkylsulfamoyl group or a substituted group It is more preferably an arylsulfamoyl group that may have a group.

Since the xanthene compound (I) in which R ⁷ is a sulfonate group, a sulfo group, a salt of a sulfo group, a carboxy group, a carboxylate group or a salt of a carboxy group can form a salt in the molecule and form a strong bond. Since the obtained film has high heat resistance and has a highly polar group, the compatibility between the xanthene compound (I) and the liquid crystal is low, and the xanthene compound (I) is difficult to elute into the liquid crystal. This is preferable because the electrical reliability of the obtained pixels tends to be high.

R ⁷ may have an alkoxycarbonyl group which may have a substituent, an aryloxycarbonyl group which may have a substituent, an alkylcarbamoyl group which may have a substituent, and a substituent. The xanthene compound (I), which may be an arylcarbamoyl group, an alkylsulfamoyl group which may have a substituent, or an arylsulfamoyl group which may have a substituent, is dissolved in an organic solvent. It is preferable because it has high properties and can be dissolved in the colored resin composition, so that it is excellent in color filter manufacturability and tends to have high pixel contrast.

When m is an integer of 2 or more, the combination of R ⁷ is not particularly limited, but a sulfamoyl group, an optionally substituted alkylsulfamoyl group, or an optionally substituted arylsulfamoyl It is preferably at least two selected from the group consisting of a group, a sulfonate group, a sulfo group, and a salt of a sulfo group.

(M)
m represents an integer of 0 to 5. When m is an integer of 2 or more, the plurality of R ⁷ may be the same or different.
In addition, from the viewpoint of the electrical reliability of the obtained pixel and the solubility of the compound in an organic solvent, it is preferable to have a more preferable group described in the above section (for R ⁷ ), and therefore m is 1 or 2 is preferable.

(P)
p represents an integer of 1 to 4. When p is 2 to 4, the structures in [] containing a plurality of xanthene skeletons may be the same or different.
When R ^{1 to} R ⁷ are a group containing a sulfonate group or a carboxylate group, n is 0 and p = 1, and otherwise, p = n × q.

  Among these, p is preferably 1 from the viewpoint of heat resistance. In the case of p = 1, the structure in [] containing the xanthene skeleton contains a sulfonate group or a carboxylate group, and salt formation is performed in the molecule or 1: 1 with the anion of X- described later. There is a tendency that a strong bond is formed and the heat resistance of the obtained film is increased.

(X ^q- and q)
X ^q− represents an arbitrary q-valent anion. q represents the integer of 1-4.
Examples of the anion of X ^q− include halide ion, PF ₆ ⁻ , ClO ₄ ⁻ , CN ⁻ , OH ⁻ , NO ₃ ⁻ , SO ₄ ²⁻ , HSO ₄ ⁻ , PO ₄ ³⁻ , HPO ₄ ^2−. , H ₂ PO ₄ ^- inorganic ions such as, carboxylato group in the molecule (-COO ^-) or a sulfonato group (--SO3 ^-) organic compounds having an anion derived from an acidic group such as, methide anion, sulfonyl imide anion Organic anions such as

Among them, a halide ion, an organic compound having a sulfonate group, a sulfonylmethide anion having an optionally substituted alkyl group having 1 to 10 carbon atoms, and an optionally substituted carbon atom having 1 to 1 carbon atoms. A sulfonylimide anion having 10 alkyl groups is preferred.
Specific examples of preferred anions include chloride ion, bromide ion, 1-naphthalenesulfonate, bistrifluoromethanesulfonylimide anion, and tristrifluoromethanesulfonylmethide anion.

(N)
n represents an integer of 0 to 4. When n is 2 to 4, the plurality of X ^q− may be the same or different. A preferred number of n is 0 or 1.
When n is 0, the structure in [] containing a xanthene skeleton contains a sulfonate group or a carboxylate group, forms a salt in the molecule, and can form a strong bond, so that the resulting film has heat resistance. And high electrical reliability. When n is 1, it has a preferable anion of the above-mentioned X ^q− and the resulting film has high heat resistance.

(Structure in [] including xanthene skeleton)
The “structure in [] containing a xanthene skeleton” in the present invention means the following structure in the structure represented by the formula (I).

[Molecular weight]
The molecular weight of the xanthene compound (I) in the present invention is usually 500 or more, preferably 600 or more, and usually 5000 or less, preferably 2000 or less.
It is preferable that it is within the above-mentioned range in terms of good solubility in a solvent and easy production.

[Specific examples of xanthene compounds (I)]
Although the preferable specific example of a xanthene type compound (I) is shown below, this invention is not limited to these.

In the above specific examples, the notation of —SO ₃ ^— group means that there are a plurality of substitution positions, and that it is obtained as a mixture of compounds having different substitution positions in the synthesis.
In addition to the above structure, C.I. I. Acid Red 50, C.I. I. Acid Red 52, C.I. I. Acid Red 87, C.I. I. Acid Red 92, C.I. I. Acid Red 289, C.I. I. Acid Red 388, International Publication No. 2011/158747, International Publication No. 2011/158748, International Publication No. 2012/53201, Japanese Unexamined Patent Publication No. 6-230210, Japanese Unexamined Patent Publication No. 2010-32999, Japanese Unexamined Patent Publication 2011. -28236, JP-A-2011-138894, JP-A-2011-241372, JP-A-2012-107192, JP-A-2012-185383, and JP-A-2012-233151. And xanthene compounds.

[Synthesis Method of Xanthene Compound (I)]
Xanthene compounds (I) are, for example, “reviewed synthetic dyes” (Horiguchi Hiroshi, Sankyo Publishing, 1968), “theoretical manufacturing dye chemistry” (Toyo Hosoda, Gihodo, 1957), synthesis and application of functional dyes. It can be synthesized according to the method described in the technology (supervised by Masaki Matsui, CMC Publishing, 2007).

Specifically, a xanthene compound can be obtained by the following methods (i) to (iii).
(I) reacting benzaldehydes with N-substituted m-aminophenols.
(Ii) reacting phthalic anhydrides with N-substituted m-aminophenols.
(Iii) A 3,6-dichloroxanthene derivative (for example, fluorescein chloride) is reacted with an N-substituted amine, and the resulting xanthene compound is sulfonated as necessary.

The xanthene compound obtained by said (i)-(iii) can introduce | transduce a substituent as needed. For example, the methods (iv) to (vii) can be mentioned.
(Iv) Sulfonation with sulfuric acid or fuming sulfuric acid, chlorination with thionyl chloride or phosphorus trichloride, amination with N-substituted amine (v) chlorosulfonylation with chlorosulfonic acid, amination with N-substituted amine (vi) Chlorination with thionyl chloride or phosphorus trichloride for a compound substituted with a carboxy group, amination with N-substituted amine (vii) Chloroform with thionyl chloride or phosphorus trichloride for a compound substituted with a carboxy group Esterification with alcohols or phenols

(Other dyes)
The (A) dye in the present invention may contain other dyes other than the xanthene compound (I) as long as the effects of the present invention are not impaired.

Other dyes include, for example, azo dyes, anthraquinone dyes, phthalocyanine dyes, quinone imine dyes, quinoline dyes, nitro dyes, carbonyl dyes, methine dyes, cyanine dyes, triarylmethane dyes, Preferred examples include dipyrromethene dyes and xanthene dyes.
Examples of the azo dye include C.I. I. Acid Yellow 11, C.I. I. Acid Orange 7, C.I. I. Acid Red 37, C.I. I. Acid Red 180, C.I. I. Acid Blue 29, C.I. I. Direct Red 28, C.I. I. Direct Red 83, C.I. I. Direct Yellow 12, C.I. I. Direct Orange 26, C.I. I. Direct Green 28, C.I. I. Direct Green 59, C.I. I. Reactive Yellow 2, C.I. I. Reactive Red 17, C.I. I. Reactive Red 120, C.I. I. Reactive Black 5, C.I. I. Disperse Orange 5, C.I. I. Disperse thread 58, C.I. I. Disperse Blue 165, C.I. I. Basic Blue 41, C.I. I. Basic Red 18, C.I. I. Molded Red 7, C.I. I. Moldant Yellow 5, C.I. I. Examples thereof include Moldant Black 7.

Examples of anthraquinone dyes include C.I. I. Bat Blue 4, C.I. I. Acid Blue 40, C.I. I. Acid Green 25, C.I. I. Reactive Blue 19, C.I. I. Reactive Blue 49, C.I. I. Disper thread 60, C.I. I. Disperse Blue 56, C.I. I. Disperse Blue 60 etc. are mentioned.
Other examples of the phthalocyanine dye include C.I. I. Pad Blue 5 and the like are quinone imine dyes such as C.I. I. Basic Blue 3, C.I. I. Basic Blue 9 and the like are quinoline dyes such as C.I. I. Solvent Yellow 33, C.I. I. Acid Yellow 3, C.I. I. Disperse Yellow 64 and the like are nitro dyes such as C.I. I. Acid Yellow 1, C.I. I. Acid Orange 3, C.I. I. Disperse Yellow 42 and the like.

Examples of the triarylmethane dye include those described in International Publication No. 2009/107734 pamphlet, International Publication No. 2011/162217 pamphlet, and the like.
Furthermore, examples of the cyanine dye include those described in International Publication No. 2011/162217 pamphlet, and preferred embodiments thereof are also the same.

(Content ratio)
The content ratio of all (A) dyes in the colored resin composition of the present invention is usually 0.03% by mass or more, preferably 0.05% by mass or more, more preferably 0 in the total solid content of the colored resin composition. .1% by mass or more, preferably 40% by mass or less, more preferably 30% by mass or less.

In the colored resin composition of the present invention, the xanthene compound (I) is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and particularly preferably 1% by mass or more in the total solid content. Further, it is preferably contained in a proportion of 50% by mass or less, more preferably 40% by mass or less, and particularly preferably 30% by mass or less.
In the colored resin composition of the present invention, the content of the xanthene compound (I) is preferably 30% by mass or more in the solid content of the total (A) dye.

  It is preferable for it to be less than or equal to the above upper limit because the curability of the coating film is unlikely to decrease and the film strength is sufficient. Moreover, since it is sufficient for coloring power to be more than the said minimum, since the chromaticity of a desired density | concentration is easy to be obtained and it is hard to become thick, it is preferable.

[(D) Photopolymerization initiator]
In the colored resin composition of the present invention, (D) the photopolymerization initiation component contains compound (II) represented by the following formula (II).

  (Compound (II))

In the above formula (II),
Z represents an aromatic ring group which may have a substituent.
m represents an integer of 0 to 20.
X is one group selected from the group consisting of —CR ⁹⁴ R ⁹⁵ —, —C (═CR ⁹⁶ R ⁹⁷ ) —, —CR ⁹⁸ ═CR ⁹⁹ — and —C≡C—, or a combination of two or more thereof. Represents a group consisting of
R ^{96 to} R ⁹⁹ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
R ⁹⁴ and R ⁹⁵ , R ¹⁰¹ and R ¹⁰² each independently represents an arbitrary substituent.
R ¹⁰¹ may be bonded to Z to form a ring, and the ring may have a substituent.
R ¹⁰³ represents an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, or an aryl group having 6 to 20 carbon atoms,
R ¹⁰⁴ to R ¹⁰⁹ each independently represents a hydrogen atom, a halogen atom, a nitro group, an alkyl group or an alkoxy group having 1 to 20 carbon atoms having 1 to 6 carbon atoms.

(M)
m represents an integer of 0 to 20, and m is preferably 0 to 5 because the amount of radically active species generated per gram is high and the production is simple.

(X and R ¹⁰¹ )
X is one selected from the group consisting of —CR ⁹⁴ R ⁹⁵ —, —C (═CR ⁹⁶ R ⁹⁷ ) —, —CR ⁹⁸ = CR ⁹⁹ —, —C≡C— and —C (═O) —. Represents a group or a group formed by bonding two or more of these.

When m is 2 or more, a plurality of X contained in one molecule may be the same or different.
R ^{96 to} R ⁹⁹ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms.
R ⁹⁴ and R ^95, R ¹⁰¹ represents an arbitrary substituent.

Optional substituents in R ⁹⁴ and R ^95, R ^101, independently, a hydrogen atom, a halogen atom, each may have a substituent, an aryl group having 6 to 20 carbon atoms, 2 carbon atoms 20 heteroaryl groups, monovalent non-aromatic heterocyclic groups having 2 to 20 carbon atoms, alkoxy groups having 1 to 20 carbon atoms, aryloxy groups having 6 to 20 carbon atoms, acyl groups having 2 to 20 carbon atoms, C2-C20 acyloxy group, C1-C20 N-substituted amino group, C3-C20 cycloalkyl group, carbamoyl group, C2-C20 alkylcarbamoyl group, C7-C20 Arylcarbamoyl group, cyano group, nitro group, alkylsulfanyl group having 1 to 12 carbon atoms, arylsulfanyl group having 6 to 20 carbon atoms, alkoxycarbonyl group having 2 to 12 carbon atoms, 3 to 12 carbon atoms It is represented by a rukenyloxycarbonyl group, an alkynyloxycarbonyl group having 3 to 12 carbon atoms, an aryloxycarbonyl group having 7 to 12 carbon atoms, a heteroaryloxycarbonyl group having 3 to 12 carbon atoms, or the following formula (2). Represents a group.

R ^30b and R ^31b each independently represent an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 20 carbon atoms, which may have a substituent.

Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Among these, a fluorine atom, a chlorine atom, and a bromine atom that are relatively stable against a nucleophilic substitution reaction are preferable.
The aryl group having 6 to 20 carbon atoms which may have a substituent preferably has 6 to 12 carbon atoms, and examples thereof include a phenyl group, a naphthyl group, and an anthracenyl group. Examples of the group which may be substituted on the aryl group include an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a hydroxyl group, an amino group, a dimethylamino group, a diethylamino group, a halogen atom, a cyano group, A sulfo group, a carboxy group, etc. are mentioned. Specific examples of the aryl group include a phenyl group, a p-tolyl group, an m-tolyl group, a p-methoxyphenyl group, a mesityl group, a naphthyl group, and an anthracenyl group.

  The heteroaryl group having 2 to 20 carbon atoms which may have a substituent is an aromatic ring group containing any one of a nitrogen atom, a sulfur atom and an oxygen atom as a heteroatom, preferably having a carbon number. The thing of 2 or more and 12 or less is mentioned. When the heteroaryl group has a plurality of heteroatoms constituting a ring other than a carbon atom, these may be the same or different. The heteroaryl group may be a single ring or a condensed ring, and may be a pyrrolyl group, imidazolyl group, pyrazolyl group, thiazolyl group, oxazolyl group, triazolyl group, thiadiazolyl group, pyridinyl group, pyrimidinyl group, triazinyl group. Quinolinyl group, isoquinolinyl group, benzothiazolinyl group, phthalimidoyl group, benzimidazolonyl group, furyl group, thiophenyl group, pyranyl group, indolinyl group, isoindolinyl group and the like. Examples of the group that may be substituted on the heteroaryl group include an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a hydroxyl group, an amino group, a dimethylamino group, a diethylamino group, a halogen atom, and a sulfo group. And a carboxy group. Specific examples of the heteroaryl group include 2-pyrrolyl group, 2-imidazolyl group, 1-pyrazolyl group, 2-thiazolyl group, 2-oxazolyl group, 1,2,4-triazol-1-yl group, and 4-pyridinyl. Group, 2-pyrimidinyl group, 4,6-diamino-2-triazinyl group, 8-quinolinyl group, 8-isoquinolinyl group, 2-benzothiazolinyl group, 6-methyl-7-sulfo-2-benzothiazolinyl Group, 1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl group, 1H-benzimidazol-2-yl group, 2-furyl group, 2-thiophenyl group, 1-indolinyl group, 2 -An isoindolinyl group is mentioned.

  The monovalent non-aromatic heterocyclic group having 2 to 20 carbon atoms which may have a substituent is a non-aromatic cyclic group containing any one of a nitrogen atom, a sulfur atom and an oxygen atom as a hetero atom. Yes, preferably those having 2 to 12 carbon atoms. When the monovalent non-aromatic heterocyclic group has a plurality of heteroatoms constituting a ring other than a carbon atom, these may be the same or different. The monovalent non-aromatic heterocyclic group may be a single ring or a condensed ring, and examples thereof include a piperidinyl group, a pyrrolidinyl group, an imidazolidinyl group, a pyrazolidinyl group, a piperazinyl group, and a morpholinyl group. Examples of the substituent that the monovalent non-aromatic heterocyclic group may have include an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a hydroxyl group, an amino group, a dimethylamino group, and diethylamino. Group, halogen atom, sulfo group and carboxy group. Specific examples of the monovalent non-aromatic heterocyclic group include 1-piperidinyl group, 1-pyrrolidinyl group, 1-imidazolidinyl group, 1-pyrazolidinyl group, 1-piperazinyl group and 1-morpholinyl group.

  The alkoxy group having 1 to 20 carbon atoms which may have a substituent is preferably an alkoxy group having 1 to 10 carbon atoms. Examples of the substituent that the alkoxy group may have include an alkoxy group having 1 to 10 carbon atoms, a phenyl group, a hydroxyl group, an amino group, a dimethylamino group, a diethylamino group, a halogen atom, a cyano group, a sulfo group, and a carboxy group. Etc. Specific examples of the alkoxy group include methoxy group, ethoxy group, n-propoxy group, isopropoxy group, n-butoxy group, s-butoxy group, t-butoxy group, n-amyloxy group, t-amyloxy group, n- Hexyloxy group, n-heptyloxy group, n-octyloxy group, hydroxyethoxy group, 1,2-dihydroxypropoxy group, 2-methoxyethoxy group, 2-ethoxyethoxy group, 2-butoxyethoxy group, 2- (2 -Methoxyethoxy) ethoxy group, 2- (2-ethoxyethoxy) ethoxy group, 2- (2-butoxyethoxy) ethoxy group, benzyloxy group, phenethyloxy group, etc., linear or branched alkoxy having 1 to 18 carbon atoms Groups.

  The aryloxy group having 6 to 20 carbon atoms which may have a substituent is preferably an aryloxy group having 6 to 14 carbon atoms. Examples of the aryloxy group include a phenoxy group, a naphthoxy group, and an anthracenyloxy group. Examples of the substituent that the aryloxy group may have include an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a hydroxyl group, an amino group, a dimethylamino group, a diethylamino group, a halogen atom, and cyano. Group, sulfo group, carboxy group and the like. Specific examples of the aryloxy group include aryls optionally having a substituent such as a phenoxy group, a 1-naphthoxy group, a 2-naphthoxy group, a 3-tolyloxy group, a 4-methoxyphenoxy group, and a 4-cyclohexylphenoxy group. An oxy group is mentioned.

Which may have a substituent alkylcarbamoyl group having a carbon number of 2-20 is represented by ^{-CO-NR 11b R 12b, R} 11b is an optionally substituted alkyl radical, R ^12b represents a hydrogen atom or an alkyl group which may have a substituent. The alkyl group usually has 1 or more carbon atoms and usually 19 or less, preferably 12 or less. Examples of the group that may be substituted with the alkyl group include an alkoxy group having 1 to 10 carbon atoms, a phenyl group, a hydroxyl group, an amino group, a dimethylamino group, a diethylamino group, a halogen atom, a cyano group, a sulfo group, and a carboxy group. Is mentioned. Specific examples of the alkyl group include methyl group, ethyl group, n-propyl group, n-butyl group, cyclohexyl group, hydroxyethyl group, 1,2-dihydroxypropyl group, 2-methoxyethyl group, 2-ethoxyethyl group. 2-butoxyethyl group, 2- (2-methoxyethoxy) ethyl group, 2- (2-ethoxyethoxy) ethyl group, 2- (2-butoxyethoxy) ethyl group, benzyl group, phenethyl group and the like. Specific examples of the alkylamino group include an ethylamino group, a dimethylamino group, a diethylamino group, a dibutylamino group, a di (2-ethoxyethyl) amino group, a diphenethylethylamino group, and a cyclohexylethyl group. Specific examples of the alkylcarbamoyl group include a methylcarbamoyl group, an ethylcarbamoyl group, a phenethylcarbamoyl group, a 2-ethylhexylcarbamoyl group, a 2-ethoxyethylcarbamoyl group, a 2- (2-ethoxyethoxy) ethylcarbamoyl group, and a dimethylcarbamoyl group. Etc.

The arylcarbamoyl group having 7 to 20 carbon atoms which may have a substituent is represented by —CO—NR ^13b R ^14b , and R ^13b represents an aryl group which may have a substituent. R ^14b represents a hydrogen atom, an alkyl group which may have a substituent, or an aryl group which may have a substituent. The preferred carbon number of the alkyl group and examples of the substituent which may be present are the same as those exemplified for the alkyl groups of R ^11b and R ^12b . The aryl group usually has 6 or more carbon atoms, usually 19 or less, preferably 12 or less, and examples thereof include a phenyl group, a naphthyl group, and an anthracenyl group. Examples of the group which may be substituted on the aryl group include an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a hydroxyl group, an amino group, a dimethylamino group, a diethylamino group, a halogen atom, a cyano group, Examples thereof include a nitro group, a sulfo group, and a carboxy group. Specific examples of the aryl group include a phenyl group, a p-tolyl group, an m-tolyl group, a p-methoxyphenyl group, a naphthyl group, and an anthracenyl group. Specific examples of the arylcarbamoyl group include a phenylcarbamoyl group, a naphthylcarbamoyl group, a p-tolylcarbamoyl group, a p-methoxyphenylcarbamoyl group, and a phenylmethylcarbamoyl group.

Optionally substituted acyl group having 2 to 20 carbon atoms is represented by -COR ^15b, R ^15b may have an optionally substituted alkyl group or a substituted group Represents an aryl group. The preferred carbon number of the alkyl group and examples of the substituent which may be present are the same as those exemplified for the alkyl groups of R ^11b and R ^12b . Examples of the preferable carbon number of the aryl group and the substituent which may be included are the same as those exemplified for the aryl group of R ⁴⁸ . Specific examples of the acyl group include acetyl group, ethylcarbonyl group, n-butylcarbonyl group, benzoyl group, p-tolylcarbonyl group, m-tolylcarbonyl group, p-methoxyphenylcarbonyl group and the like.

The acyloxy group having 2 to 20 carbon atoms which may have a substituent is represented by —O—COR ^16b , and R ^16b has an alkyl group or a substituent which may have a substituent. Represents a good aryl group. The preferred carbon number of the alkyl group and examples of the substituent which may be present are the same as those exemplified for the alkyl groups of R ^11b and R ^12b . Examples of the preferable carbon number of the aryl group and the substituent which may be included are the same as those exemplified for the aryl group of R ^13b . Specific examples of the acyl group include an acetoxy group, an ethylcarbonyloxy group, an n-butylcarbonyloxy group, a benzoyloxy group, a p-tolylcarbonyloxy group, an m-tolylcarbonyloxy group, and a p-methoxyphenylcarbonyloxy group. Is mentioned.

The optionally substituted N-substituted amino group having 1 to 20 carbon atoms is represented by —NR ^17b R ^18b , where R ^17b is a hydrogen atom, an ^optionally substituted alkyl group, a substituted group. An aryl group which may have a group is represented. R ^18b represents an alkyl group which may have a substituent and an aryl group which may have a substituent. The preferred carbon number of the alkyl group and examples of the substituent which may be present are the same as those exemplified for the alkyl groups of R ^11b and R ^12b . Examples of the preferable carbon number of the aryl group and the substituent which may be included are the same as those exemplified for the aryl group of R ^13b . Specific examples of the N-substituted amino group include an ethylamino group, a dimethylamino group, a diethylamino group, a dibutylamino group, a di (2-ethoxyethyl) amino group, a diphenethylethylamino group, a cyclohexylethyl group, and a phenylamino group. , Diphenylamino group, di (p-tolyl) amino group, di (p-methoxyphenyl) amino group, ethylphenylamino group, n-butylphenylamino group and the like.

  The cycloalkyl group having 3 to 20 carbon atoms which may have a substituent is preferably a cycloalkyl group having 3 to 12 carbon atoms. Examples of the cycloalkyl group include a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, and a decalinyl group. Examples of the group which may be substituted on the cycloalkyl group include an alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a hydroxyl group, an amino group, a dimethylamino group, a diethylamino group, a halogen atom, and a cyano group. , Sulfo group and carboxy group. Specific examples of the cycloalkyl group include a cyclopentyl group, a cyclohexyl group, a cyclooctyl group, and a decalinyl group.

Alkylsulfanyl group having 1 to 12 carbon atoms which may have a substituent group is represented by -S-R ^22b, R ^22b represents an alkyl group which may have a substituent. The preferred carbon number of the alkyl group and examples of the substituent which may be present are the same as those exemplified for the alkyl groups of R ^11b and R ^12b . Specific examples of the alkylsulfanyl group include a methylsulfanyl group, an ethylsulfanyl group, a phenethylsulfanyl group, a 2-ethylhexylsulfanyl group, a 2-ethoxyethylsulfanyl group, a 2- (2-ethoxyethoxy) ethylsulfanyl group, and trifluoromethyl. And a sulfanyl group.

The arylsulfanyl group having 6 to 20 carbon atoms which may have a substituent is represented by —S—R ^23b , and R ^23b represents an aryl group which may have a substituent. Examples of the preferable carbon number of the aryl group and the substituent which may be included are the same as those exemplified for the aryl group of R ^13b . Specific examples of the arylsulfanyl group include phenylsulfanyl group, naphthylsulfanyl group, p-tolylsulfanyl group, m-tolylsulfanyl group, o-tolylsulfanyl group, p-methoxysulfanyl group, p-nitrosulfanyl group and the like. It is done.

An alkoxycarbonyl group having 2 to 12 carbon atoms which may have a substituent group is represented by -CO-OR ^24b, R ^24b represents an alkyl group which may have a substituent. The preferred carbon number of the alkyl group and examples of the substituent which may be present are the same as those exemplified for the alkyl groups of R ^11b and R ^12b . Specific examples of the alkoxycarbonyl group include methoxycarbonyl group, ethoxycarbonyl group, n-butoxycarbonyl group, phenethyloxycarbonyl group, 2-ethylhexyloxycarbonyl group, 2-ethoxyethoxycarbonyl group and the like.

The alkenyloxycarbonyl group having 3 to 12 carbon atoms which may have a substituent is represented by —CO—OR ^25b , and R ^25b represents an alkenyl group which may have a substituent. The alkenyl group usually has 1 or more carbon atoms and usually 11 or less, preferably 8 or less. Examples of the group that may be substituted with the alkenyl group include an alkoxy group having 1 to 8 carbon atoms, a phenyl group, a hydroxyl group, an amino group, a dimethylamino group, a diethylamino group, a halogen atom, a cyano group, a sulfo group, and a carboxy group. Is mentioned. Specific examples of the alkenyl group include a vinyl group, an allyl group, and a methanyl group. Specific examples of the alkenyloxycarbonyl group include alkenyloxycarbonyl groups having 3 to 12 carbon atoms such as vinyloxycarbonyl group and allyloxycarbonyl group.

Which may have a substituent alkynyloxy group having 3 to 12 carbon atoms is represented by -CO-OR ^26b, R ^26b represents an alkynyl group which may have a substituent. The alkynyl group usually has 1 or more carbon atoms and usually 11 or less, preferably 8 or less. Examples of the group which may be substituted on the alkynyl group include an alkoxy group having 1 to 8 carbon atoms, a phenyl group, a hydroxyl group, an amino group, a dimethylamino group, a diethylamino group, a halogen atom, a cyano group, a sulfo group and a carboxy group Is mentioned. Specific examples of the alkynyl group include a methynyl group, a propynyl group, and a butynyl group. Specific examples of the alkynyloxycarbonyl group include alkynyloxycarbonyl groups having 3 to 12 carbon atoms such as methynyloxycarbonyl group and propynyloxycarbonyl group.

The aryloxycarbonyl group having 7 to 12 carbon atoms which may have a substituent is represented by —CO—OR ^27b , and R ^27b represents an aryl group which may have a substituent. Examples of the preferable carbon number of the aryl group and the substituent which may be included are the same as those exemplified for the aryl group of R ^13b . Specific examples of the aryloxycarbonyl group include those having 7 to 12 carbon atoms such as phenyloxycarbonyl group, 1-naphthyloxycarbonyl group, 2-naphthyloxycarbonyl group, p-tolyloxycarbonyl group, p-methoxyphenyloxycarbonyl group and the like. An aryloxycarbonyl group is mentioned.

Which may have a substituent heteroaryloxy group having 3 to 12 carbon atoms is represented by -CO-OR ^28b, R ^28b represents a heteroaryl group which may have a substituent. Examples of the preferred carbon number of the heteroaryl group and optionally substituted substituents are the same as the preferred carbon number of the heteroaryl group in R ⁵⁴ , R ⁵⁵ and R ¹⁰¹ and optionally substituted. is there. Specific examples of the heteroaryloxycarbonyl group include 8-quinolinyloxycarbonyl group, 2-furanyloxycarbonyl group, 3-furanyloxycarbonyl group, 2-pyridyloxycarbonyl group, 3-pyridyloxycarbonyl group, 4 -Heteroaryloxycarbonyl groups having 3 to 12 carbon atoms such as a pyridyloxycarbonyl group and a 2-benzothiazolyloxycarbonyl group.

Examples of the alkyl group having 1 to 12 carbon atoms which may have a substituent of R ^30b and R ^31b are the same as those exemplified for the alkyl groups of R ^11b and R ^12b . Examples of the aryl group having 6 to 20 carbon atoms which may have a substituent are the same as those exemplified for the aryl group of R ^13b .
R ¹⁰¹ may be bonded to Z to form a ring, and the ring may have a substituent.

Among these, X is preferably —CH ₂ —, —CH (CH ₃ ) — or —C (CH ₃ ) ₂ — from the viewpoint of solubility and raw material availability, and —CH ₂ — or —CH (CH ₃ ) — is more preferable, and —CH ₂ — is still more preferable.
Of these, R ¹⁰¹ is preferably hydrogen, a cycloalkyl group having 3 to 20 carbon atoms, or an alkoxycarbonyl group having 2 to 12 carbon atoms, from the viewpoint of solubility and availability of raw materials. It is more preferably a 2-7 alkoxycarbonyl group, and further preferably a C2-5 alkoxycarbonyl group.

( ^R102 )
^R102 represents an arbitrary substituent.
As an arbitrary substituent in R ^102, an optionally substituted alkylcarbonyl group having 2 to 20 carbon atoms, an alkenylcarbonyl group having 3 to 25 carbon atoms, and a cycloalkylcarbonyl group having 4 to 8 carbon atoms , An arylcarbonyl group having 7 to 20 carbon atoms, an alkoxycarbonyl group having 2 to 10 carbon atoms, an aryloxycarbonyl group having 7 to 20 carbon atoms, a heteroarylcarbonyl group having 3 to 20 carbon atoms, or an alkyl having 2 to 20 carbon atoms Represents an aminocarbonyl group.

  Examples of the alkylcarbonyl group having 2 to 20 carbon atoms which may have a substituent include an acetyl group, a propanoyl group, a butanoyl group, and the like, and preferably an acetyl group. Carbon number becomes like this. Preferably it is 2-10, More preferably, it is 2-7.

  Examples of the alkenylcarbonyl group having 3 to 25 carbon atoms which may have a substituent include a crotonoyl group and an acryloyl group, and a crotonoyl group is preferable. Carbon number becomes like this. Preferably it is 3-12, More preferably, it is 3-7.

  Examples of the cycloalkylcarbonyl group having 4 to 8 carbon atoms which may have a substituent include a cyclohexylcarbonyl group, a methylcyclohexylcarbonyl group and a cyclopentylcarbonyl group, and a cyclohexylcarbonyl group is preferable. The number of carbon atoms is preferably 4-7.

  Examples of the arylcarbonyl group having 7 to 20 carbon atoms which may have a substituent include a benzoyl group, a methylbenzoyl group, and a naphthoyl group, and a benzoyl group is preferable. Carbon number becomes like this. Preferably it is 7-12, More preferably, it is 7-10.

  Examples of the C2-C10 alkoxycarbonyl group which may have a substituent include a methoxycarbonyl group, an ethoxycarbonyl group, and a propoxycarbonyl group, and a methoxycarbonyl group is preferable. The number of carbon atoms is preferably 2-8.

  Examples of the aryloxycarbonyl group having 7 to 20 carbon atoms which may have a substituent include a phenoxycarbonyl group, a p-methylphenoxycarbonyl group, and a naphthoxycarbonyl group, and a phenoxycarbonyl group is preferable. Carbon number becomes like this. Preferably it is 7-15, More preferably, it is 7-10.

  Examples of the heteroarylcarbonyl group having 3 to 20 carbon atoms which may have a substituent include a thiophenecarbonyl group, a pyrrolylcarbonyl group, a pyridinecarbonyl group, and the like, and preferably a thiophenecarbonyl group. Carbon number becomes like this. Preferably it is 5-15, More preferably, it is 7-10.

  Examples of the alkylaminocarbonyl group having 2 to 20 carbon atoms which may have a substituent include a morpholinocarbonyl group, a dimethylaminocarbonyl group, and a methylaminocarbonyl group, and a dimethylaminocarbonyl group is preferable. Carbon number becomes like this. Preferably it is 2-12, More preferably, it is 2-10.

Of the above groups, from the viewpoint of exposure sensitivity, R ¹⁰² is preferably an alkylcarbonyl group, a cycloalkylcarbonyl group, or an arylcarbonyl group, and more preferably an alkylcarbonyl group or an arylcarbonyl group.
Examples of the substituent that each group described above as R ¹⁰² may have include those described in the following section (Substituent group W ² ), and each group described above has a substituent. Those that do not are particularly preferred.

(Substituent group W ² )
C1-C8 alkyl group, C1-C10 alkoxy group, phenyl group, hydroxyl group, amino group, dimethylamino group, diethylamino group, halogen atom, cyano group, sulfo group and carboxy group

(R ¹⁰³ )
R ¹⁰³ represents an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, or an aryl group having 6 to 20 carbon atoms.

  Examples of the alkyl group include methyl group, ethyl group, n-propyl group, n-butyl group, cyclohexyl group, hydroxyethyl group, 1,2-dihydroxypropyl group, 2-methoxyethyl group, 2-ethoxyethyl group, 2 -Butoxyethyl group, 2- (2-methoxyethoxy) ethyl group, 2- (2-ethoxyethoxy) ethyl group, 2- (2-butoxyethoxy) ethyl group, benzyl group, phenethyl group and the like can be mentioned. Carbon number becomes like this. Preferably it is 1-10, More preferably, it is 1-6.

Examples of the alkenyl group include allyl group and methanyl group. The number of carbon atoms is preferably 3-4.
The aryl group is the same as that described in the section <About X and R ¹⁰¹ >.
Examples of the substituent that each group described above as R ¹⁰³ may have include those described in the above section (Substituent group W ¹ ), and each group described above has a substituent. Those that do not are particularly preferred.

R ¹⁰³ is preferably an alkyl group having 1 to 6 carbon atoms, particularly preferably an ethyl group, from the viewpoint that the amount of radical active species generated per gram is high and the production is simple.

(R ¹⁰⁴ ~R ¹⁰⁹⁾
R ¹⁰⁴ to R ¹⁰⁹ each independently represents a hydrogen atom, a halogen atom, a nitro group, an alkyl group or an alkoxy group having 1 to 20 carbon atoms having 1 to 6 carbon atoms.

R ^{104 to} R ¹⁰⁹ are each preferably a hydrogen atom, a halogen atom or an alkyl group having 1 to 6 carbon atoms in view of a high generation amount of radical active species per gram and further easy production. The alkyl group having 1 to 6 carbon atoms is more preferable, and a hydrogen atom is particularly preferable.

(Z)
Z represents an aromatic ring group which may have a substituent. Examples of the aromatic ring group include an aromatic hydrocarbon ring group and an aromatic heterocyclic group.

  The aromatic hydrocarbon ring group may be a single ring or a condensed ring, and preferably has 5 to 18 carbon atoms forming the ring, for example, a benzene ring having one free valence, Examples include a naphthalene ring, anthracene ring, phenanthrene ring, perylene ring, tetracene ring, pyrene ring, benzpyrene ring, chrysene ring, triphenylene ring, acenaphthene ring, fluoranthene ring, fluorene ring, and indene ring.

  The aromatic heterocyclic group may be a single ring or a condensed ring, and preferably has 3 to 10 carbon atoms forming the ring, for example, a furan ring having one free valence. Benzofuran ring, thiophene ring, benzothiophene ring, pyrrole ring, pyrazole ring, imidazole ring, oxadiazole ring, indole ring, carbazole ring, pyrroloimidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrrole ring, thienothiophene ring, Furopyrrole ring, furofuran ring, thienofuran ring, benzoisoxazole ring, benzisothiazole ring, benzimidazole ring, pyridine ring, pyrazine ring, pyridazine ring, pyrimidine ring, triazine ring, quinoline ring, isoquinoline ring, cinnoline ring, quinoxaline ring, Phenanthridine ring, benzimidazole Ring, perimidine ring, a quinazoline ring, a quinazolinone ring, azulene ring, an acridine ring, a xanthene ring, a phenazine ring, a phenothiazine ring, a phenoxazine ring, groups such as a benzothiazole ring.

As the aromatic substituent which may be ring group optionally having in Z, for example, those described in the section below [Substituent Group W ^3].
[Substituent group W ³ ]
An alkyl group having 1 to 8 carbon atoms, an alkoxy group having 1 to 8 carbon atoms, a hydroxyl group, an amino group, a dimethylamino group, a diethylamino group, a halogen atom, a sulfo group, and a carboxy group;

  Among these, from the viewpoint of light absorption wavelength, Z is preferably a benzene ring, naphthalene ring or thiophene ring which may have a substituent, and a benzene ring or naphthalene ring which may have a substituent. More preferably, it is a benzene ring which may have a substituent.

[Specific Examples of Compound (II)]
Although the preferable specific example of compound (II) in this invention is shown below, this invention is not limited to these.

In addition, from the viewpoint of radical generation efficiency and sensitivity, the compound (II) in the present invention has an steric configuration in which the R ¹⁰² O group and the carbonyl group in the formula (II) are an anti-C═N bond. The proportion of isomers that can be a locus is preferably 90% or more, more preferably 95% or more, and still more preferably 97% or more.

  As a method for obtaining a compound in which the proportion of an isomer (anti-isomer) that is an anti-conformation is 90% or more, synthesis conditions can be appropriately adjusted. The abundance ratio of the cis-anti body can be confirmed by, for example, NMR, high performance liquid chromatography (HPLC) or the like.

(Other photopolymerization initiators)
The colored resin composition of the present invention may contain other photopolymerization initiator other than the compound (II) as long as the effects of the present invention are not impaired.
Other photopolymerization initiators include, for example, benzoin alkyl ethers, anthraquinone derivatives; acetophenone derivatives such as 2-methyl- (4′-methylthiophenyl) -2-morpholino-1-propanone, 2-ethylthioxanthone, Examples also include thioxanthone derivatives such as 2,4-diethylthioxanthone, benzoate derivatives, acridine derivatives, phenazine derivatives, and anthrone derivatives. Commercial products may be used as these initiators. Examples of commercially available products include IRGACURE (registered trademark, the same shall apply hereinafter) 651, IRGACURE 184, DAROCUR (registered trademark) 1173, IRGACURE 2959, IRGACURE 127, IRGACURE 907, IRGACURE 369, IRGACURE 379EG, trademark LUCIR IRGACURE 819, IRGACURE 784 (manufactured by BASF), TRONLY TR-PBG-304, TRONLY TR-PBG-305, TRONLY TR-PBG-309, TRONLY TR-PBG-314 (manufactured by Changzhou Powerful Electronic New Materials Co., Ltd.), NCI-930, NCI-831, N-1919 (made by ADEKA) etc. are mentioned.

In addition to (D1) photopolymerization initiator, (D) photopolymerization initiation component includes a polymerization accelerator (hereinafter also referred to as “(D2) component”), a sensitizing dye (hereinafter referred to as “optionally“ An additive such as (D3) component ”may be used in combination.
Examples of the (D2) polymerization accelerator used as necessary include N, N-dialkylaminobenzoic acid alkyl esters such as N, N-dimethylaminobenzoic acid ethyl ester; 2-mercaptobenzothiazole, 2-mercapto Examples thereof include mercapto compounds having a heterocyclic ring such as benzoxazole and 2-mercaptobenzimidazole; mercapto compounds such as aliphatic polyfunctional mercapto compounds.

One of these (D2) polymerization accelerators may be used alone, or two or more thereof may be used in combination.
Further, (D3) sensitizing dye is used for the purpose of increasing the sensitivity as required. As the sensitizing dye, an appropriate one is used according to the wavelength of the image exposure light source. For example, xanthene dyes described in JP-A-4-221958 and JP-A-4-219756; Coumarin dyes having a heterocyclic ring described in JP-A-3-239703, JP-A-5-289335, etc .; JP-A-3-239703, JP-A-5-289335, etc. Ketocoumarin dyes; pyromethene dyes described in JP-A-6-19240, etc .; JP-A-47-2528, JP-A-54-155292, JP-B-45-37377, JP-A-48- 84183, JP 52-112681, JP 58-15503, JP 60-88005, JP 59-56403, JP The dialkylaminobenzene skeleton described in each publication, such as 2-69, JP-A-57-168088, JP-A-5-107761, JP-A-5-210240, JP-A-4-288818, etc. And the like.

(D3) A sensitizing dye may also be used alone or in combination of two or more.
In the colored resin composition of the present invention, the content ratio of these (D) photopolymerization initiation components is usually 0.1% by mass or more, preferably 0.2% by mass or more, and more preferably 0.8% by mass in the total solid content. It is 5% by mass or more, usually 40% by mass or less, preferably 30% by mass or less, and more preferably 20% by mass or less.

In addition, the colored resin composition of the present invention, from the viewpoint of sensitivity, contains the compound (II) in the total solid content, preferably 0.005% by mass or more, more preferably 0.01% by mass or more, and still more preferably 0.8. It is contained in a proportion of 1% by mass or more, particularly preferably 1% by mass or more, preferably 40% by mass or less, more preferably 30% by mass or less.
In the colored resin composition of the present invention, the content ratio of the compound (II) is preferably 5% by mass or more, more preferably 10% by mass or more in the total (D) photopolymerization initiation component. More preferably, it is 30% by mass or more.

Within the above range, the sensitivity to the exposure light beam is good, the solubility of the unexposed portion in the developer is good, and it is preferable in that it is difficult to induce poor development.
In addition, the compound (II) contained in the colored resin composition of the present invention is usually 0.4 mass times or more, preferably 0 with respect to the total solid content of the (A) dye containing the xanthene compound (I). .6 mass times or more, more preferably 1.0 mass times or more, and usually 30 mass times or less, preferably 20 mass times or less.

Within the above range, it is preferable in that the effect of the present invention can be favorably obtained.
<Reason why the colored resin composition of the present invention is effective>
The reason why the colored resin composition containing the xanthene compound (I) has the effect of improving the sensitivity without significantly reducing the luminance of the resulting pixel by including the compound (II) as a photopolymerization initiator. Is not clear, but can be estimated as follows.

The dye contained in the colored resin composition interacts with a photopolymerization initiator present in the same system. As a result, energy is transferred from the photopolymerization initiator activated by receiving light energy to the dye, and as a result, the radical generation efficiency of the photopolymerization initiator is lowered, and consequently the sensitivity of the colored resin composition is lowered. Resulting in.
A photoinitiator will absorb light energy, will be in an excited state, and will be in the state (transition state) which generates a radical after that. If the energy level at the time of radical generation is close to the energy level of the excited state of the dye, energy transfer to the dye occurs.
Compound (I) having a xanthene skeleton had a maximum absorption wavelength at 500 to 600 nm, energy transfer from the photopolymerization initiator was likely to occur, and the sensitivity of the colored resin composition was markedly lowered. On the other hand, the compound (II) having a carbazole skeleton has a maximum absorption at an exposure wavelength of 350 to 410 nm used for photocuring of the colored resin composition, and particularly has a maximum absorption near i-line (365 nm). High efficiency of generation. In addition, compound (II) has a tendency not to cause a decrease in luminance of the resulting pixel because a decomposition product generated by photolysis and a by-product generated by reaction of the decomposition product do not absorb in the visible region (380 nm to 780 nm). There is.

[(B) Solvent]
The solvent (B) contained in the colored resin composition of the present invention has a function of adjusting the viscosity by dissolving or dispersing each component contained in the colored resin composition.

  The solvent (B) may be any solvent as long as it can dissolve or disperse each component constituting the colored resin composition, and a solvent having a boiling point in the range of 100 to 200 ° C. is preferably selected. More preferably, it has a boiling point of 120-170 ° C.

Examples of such solvents include the following.
Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol-mono t-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, methoxymethylpentanol, propylene Glycol monoalkyl ethers such as glycol monoethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monomethyl ether, 3-methyl-3-methoxybutanol, tripropylene glycol monomethyl ether;
Glycol dialkyl ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether;
Ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, methoxybutyl acetate, 3-methoxybutyl acetate, methoxypentyl acetate, diethylene glycol monoethyl Glycol alkyl ether acetates such as ether acetate, diethylene glycol monobutyl ether acetate, dipropylene glycol monomethyl ether acetate, 3-methyl-3-methoxybutyl acetate;
Ethers such as diethyl ether, dipropyl ether, diisopropyl ether, diamyl ether, ethyl isobutyl ether, dihexyl ether;
Ketones such as acetone, methyl ethyl ketone, methyl amyl ketone, methyl isopropyl ketone, methyl isoamyl ketone, diisopropyl ketone, diisobutyl ketone, methyl isobutyl ketone, cyclohexanone, ethyl amyl ketone, methyl butyl ketone, methyl hexyl ketone, methyl nonyl ketone;
Mono- or polyhydric alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, glycerin;
aliphatic hydrocarbons such as n-pentane, n-octane, diisobutylene, n-hexane, hexene, isoprene, dipentene, dodecane;
Cycloaliphatic hydrocarbons such as cyclohexane, methylcyclohexane, methylcyclohexene, bicyclohexyl;
Aromatic hydrocarbons such as benzene, toluene, xylene, cumene;
Amyl formate, ethyl formate, ethyl acetate, butyl acetate, propyl acetate, amyl acetate, cyclohexyl acetate, methyl isobutyrate, ethylene glycol acetate, ethyl propionate, propyl propionate, butyl butyrate, isobutyl butyrate, isobutyric acid Methyl, ethyl caprylate, butyl stearate, ethyl benzoate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, propyl 3-methoxypropionate, 3- Linear or cyclic esters such as butyl methoxypropionate, γ-butyrolactone;
Alkoxycarboxylic acids such as 3-methoxypropionic acid and 3-ethoxypropionic acid;
Halogenated hydrocarbons such as butyl chloride and amyl chloride;
Ether ketones such as methoxymethylpentanone;
Nitriles such as acetonitrile and benzonitrile:
These solvents may be used alone or in combination of two or more.

  Of these solvents, glycol monoalkyl ethers are preferred from the viewpoint of the solubility of the dye (A) in the present invention. Among these, propylene glycol monomethyl ether is particularly preferable from the viewpoint of solubility of various components in the colored resin composition.

  In addition, for example, in the case of containing a pigment (F) described later as an optional component, the balance of coatability, surface tension, etc. is good, and from the viewpoint that the solubility of the constituent components in the colored resin composition is relatively high, It is more preferable to use a mixture of glycol alkyl ether acetates. In addition, in colored resin compositions containing pigments, glycol monoalkyl ethers are highly polar and tend to aggregate the pigment, which may reduce storage stability, such as increasing the viscosity of the colored resin composition. For this reason, it is preferable that the amount of glycol monoalkyl ethers used is not excessively large, and the proportion of glycol monoalkyl ethers in the solvent (B) is preferably 5 to 50% by mass, more preferably 5 to 30% by mass. .

  Further, from the viewpoint of suitability for a slit coat method corresponding to a recent large substrate or the like, it is also preferable to use a solvent having a boiling point of 150 ° C. or higher. In this case, the content of such a high-boiling solvent is preferably 3 to 50% by mass, more preferably 5 to 40% by mass, and particularly preferably 5 to 30% by mass with respect to the entire solvent (B). If the amount of the high boiling point solvent is too small, for example, a dye component may precipitate and solidify at the tip of the slit nozzle to cause foreign matter defects, and if it is too large, the drying speed of the composition will be slowed down. There is a concern that the filter manufacturing process may cause problems such as tact defects in the vacuum drying process and pin marks of prebaking.

  The solvent having a boiling point of 150 ° C. or higher may be glycol alkyl ether acetates or glycol alkyl ethers. In this case, a solvent having a boiling point of 150 ° C. or higher may not be included separately. .

  The colored resin composition of the present invention may be used for color filter production by the ink jet method, but in color filter production by the ink jet method, the ink emitted from the nozzle is very small, from several to several tens pL, There is a tendency for the solvent to evaporate and the ink to concentrate and dry before landing on the periphery of the nozzle opening or in the pixel bank. In order to avoid this, it is preferable that the solvent has a high boiling point. Specifically, it is preferable that the solvent (B) contains a solvent having a boiling point of 180 ° C. or higher. In particular, it is preferable to contain a solvent having a boiling point of 200 ° C. or higher, particularly 220 ° C. or higher. Moreover, it is preferable that the high boiling point solvent whose boiling point is 180 degreeC or more is 50 mass% or more in (B) solvent. When the ratio of such a high boiling point solvent is less than 50% by mass, the effect of preventing evaporation of the solvent from the ink droplets may not be sufficiently exhibited.

  In the colored resin composition of the present invention, the content of the (B) solvent is not particularly limited, but the upper limit is usually 99% by mass. When the content of the solvent (B) in the composition exceeds 99% by mass, the concentration of each component excluding the solvent (B) may become too low to form a coating film. On the other hand, the lower limit of the content of the solvent (B) is usually 75% by mass, preferably 80% by mass, and more preferably 82% by mass in consideration of viscosity suitable for coating.

[(C) Binder resin]
(C) What preferable binder resin changes with the hardening means of a colored resin composition.
When the colored resin composition of the present invention is a photopolymerizable resin composition, examples of the (C) binder resin include JP-A-7-2072111, JP-A-8-259876, and JP-A-10-300922. The polymer compounds described in JP-A-11-140144, JP-A-11-174224, JP-A-2000-56118, JP-A-2003-233179, and the like can be used. Of these, the following resins (C-1) to (C-5) are preferred.

(C-1): With respect to a copolymer of an epoxy group-containing (meth) acrylate and another radical polymerizable monomer, an unsaturated monobasic acid is added to at least a part of the epoxy group of the copolymer. Resin to be added, or an alkali-soluble resin (hereinafter referred to as “resin (C-1)”) obtained by adding a polybasic acid anhydride to at least a part of the hydroxyl group generated by the addition reaction. .)
(C-2): Carboxyl group-containing linear alkali-soluble resin (C-2) (hereinafter sometimes referred to as “resin (C-2)”)
(C-3): a resin obtained by adding an epoxy group-containing unsaturated compound to the carboxyl group portion of the resin (C-2) (hereinafter sometimes referred to as “resin (C-3)”).
(C-4): (Meth) acrylic resin (hereinafter sometimes referred to as “resin (C-4)”)
(C-5): Epoxy acrylate resin having a carboxyl group (hereinafter sometimes referred to as “resin (C-5)”)
Of these, the resin (C-1) is particularly preferable, and the resin will be described below.

  The resins (C-2) to (C-5) may be anything as long as they are dissolved in an alkaline developer and are soluble to the extent that the desired development processing is performed. It is the same as that described as the same item of 2009-025813 gazette. The preferred embodiment is also the same.

(C-1): With respect to a copolymer of an epoxy group-containing (meth) acrylate and another radical polymerizable monomer, an unsaturated monobasic acid is added to at least a part of the epoxy group of the copolymer. As one of particularly preferable resins of the alkali-soluble resin resin (C-1) obtained by adding a polybasic acid anhydride to at least a part of the hydroxyl group generated by the addition reaction, or an epoxy group, Unsaturated in 10 to 100 mol% of the epoxy group of the copolymer with respect to the copolymer of 5 to 90 mol% of (meth) acrylate and 10 to 95 mol% of other radical polymerizable monomer Examples thereof include a resin obtained by adding a monobasic acid, or an alkali-soluble resin obtained by adding a polybasic acid anhydride to 10 to 100 mol% of a hydroxyl group generated by the addition reaction.

  Examples of the epoxy group-containing (meth) acrylate include glycidyl (meth) acrylate, 3,4-epoxybutyl (meth) acrylate, (3,4-epoxycyclohexyl) methyl (meth) acrylate, and 4-hydroxybutyl (meth) acrylate. ) Acrylate glycidyl ether and the like. Of these, glycidyl (meth) acrylate is preferred. These epoxy group-containing (meth) acrylates may be used alone or in combination of two or more.

  The other radical polymerizable monomer copolymerized with the epoxy group-containing (meth) acrylate is not particularly limited as long as the effects of the present invention are not impaired. For example, vinyl aromatics, dienes, (meth) Examples include acrylic acid esters, (meth) acrylic acid amides, vinyl compounds, unsaturated dicarboxylic acid diesters, monomaleimides, and the like, and in particular, mono (meth) having a structure represented by the following formula (7) Acrylate is preferred.

  The repeating unit derived from the mono (meth) acrylate having the structure represented by the following formula (7) contains 5 to 90 mol% among the repeating units derived from “other radical polymerizable monomers”. The content is preferably 10 to 70 mol%, more preferably 15 to 50 mol%.

In the above formula (7), R ⁸⁹ represents a hydrogen atom or a methyl group, and R ⁹⁰ represents a structure represented by the following formula (8).

The formula (8), R ⁹¹ ~R ⁹⁸ independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. R ⁹⁶ and R ⁹⁸ may be connected to each other to form a ring. The ring formed by connecting R ⁹⁶ and R ⁹⁸ is preferably an aliphatic ring, may be saturated or unsaturated, and preferably has 5 to 6 carbon atoms.
Among these, among the structures represented by the formula (8), those represented by the following structural formulas (8a), (8b), or (8c) are particularly preferable.

In addition, the mono (meth) acrylate which has a structure represented by the said Formula (8) may be used individually by 1 type, and may use 2 or more types together.
As "other radical polymerizable monomers" other than the mono (meth) acrylate having the structure represented by the formula (8), the heat resistance and strength excellent in the colored resin composition can be improved. , Styrene, (n-butyl) (meth) acrylate, tert-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, adamantyl (meth) acrylate, benzyl (meth) acrylate , (Meth) acrylic acid-2-hydroxyethyl, N-phenylmaleimide, N-cyclohexylmaleimide.

The content of the repeating unit derived from at least one selected from the above monomer group is preferably 1 to 70 mol%, more preferably 3 to 50 mol%.
A known solution polymerization method is applied to the copolymerization reaction between the epoxy group-containing (meth) acrylate and the other radical polymerizable monomer.
In the present invention, as a copolymer of the epoxy group-containing (meth) acrylate and the other radical polymerizable monomer, 5 to 90 mol% of repeating units derived from the epoxy group-containing (meth) acrylate, and others Is preferably composed of 10 to 95 mol% of repeating units derived from the radically polymerizable monomer, more preferably composed of 20 to 80 mol% of the former and 80 to 20 mol% of the latter. What consists of 70 mol% and the latter 70-30 mol% is especially preferable.

Within the above range, the addition amount of the polymerizable component and alkali-soluble component described later is sufficient, and the heat resistance and the strength of the film are sufficient, which is preferable.
The epoxy group portion of the epoxy group-containing copolymer synthesized as described above is reacted with an unsaturated monobasic acid (polymerizable component) and a polybasic acid anhydride (alkali-soluble component).
Here, as an unsaturated monobasic acid added to an epoxy group, a well-known thing can be used, For example, unsaturated carboxylic acid which has an ethylenically unsaturated double bond is mentioned.

  Specific examples include (meth) acrylic acid, crotonic acid, o-, m-, p-vinylbenzoic acid, α-position substituted with a haloalkyl group, an alkoxyl group, a halogen atom, a nitro group, or a cyano group. And monocarboxylic acids such as (meth) acrylic acid. Of these, (meth) acrylic acid is preferred. These may be used alone or in combination of two or more.

By adding such components, polymerizability can be imparted to the binder resin used in the present invention.
These unsaturated monobasic acids are usually added to 10 to 100 mol% of the epoxy group of the copolymer, preferably 30 to 100 mol%, more preferably 50 to 100 mol%. It is preferable for it to be in the above range since the colored resin composition is excellent in stability over time. In addition, a well-known method is employable as a method of adding unsaturated monobasic acid to the epoxy group of a copolymer.

Furthermore, a well-known thing can be used as a polybasic acid anhydride added to the hydroxyl group produced when an unsaturated monobasic acid is added to the epoxy group of a copolymer.
For example, dibasic acid anhydrides such as maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, chlorendic anhydride; trimellitic anhydride, pyromellitic anhydride, benzophenone Examples thereof include anhydrides of three or more bases such as tetracarboxylic acid anhydride and biphenyltetracarboxylic acid anhydride. Of these, succinic anhydride and tetrahydrophthalic anhydride are preferred. These polybasic acid anhydrides may be used individually by 1 type, and may use 2 or more types together.

By adding such a component, alkali solubility can be imparted to the binder resin used in the present invention.
These polybasic acid anhydrides are usually added to 10 to 100 mol% of the hydroxyl group generated by adding an unsaturated monobasic acid to the epoxy group of the copolymer, preferably 20 to 90 mol. %, More preferably 30 to 80 mol%.

Within the above range, the remaining film ratio and solubility during development are sufficient, which is preferable.
In addition, a well-known method is employable as a method of adding a polybasic acid anhydride to the said hydroxyl group.
Furthermore, in order to improve photosensitivity, after adding the above-mentioned polybasic acid anhydride, glycidyl (meth) acrylate or a glycidyl ether compound having a polymerizable unsaturated group is added to a part of the generated carboxyl group. May be. Such a resin structure is described in, for example, Japanese Patent Application Laid-Open Nos. 8-297366 and 2001-89533.

The polystyrene-reduced weight average molecular weight (Mw) of the above-described binder resin (C-1) measured by GPC (gel permeation chromatography) is preferably 3000 to 100,000, and particularly preferably 5000 to 50000. Within the above range, heat resistance, film strength, and solubility in a developer are preferable.
Moreover, as a standard of molecular weight distribution, the ratio of weight average molecular weight (Mw) / number average molecular weight (Mn) is preferably 2.0 to 5.0.

In addition, the acid value of binder resin (C-1) is 10-200 mg-KOH / g normally, Preferably it is 15-150 mg-KOH / g, More preferably, it is 25-100 mg-KOH / g. If the acid value is too low, the solubility in the developer may be reduced. Conversely, if it is too high, film roughening may occur.
Content of (C) binder resin in a colored resin composition is 0.1-80 mass% normally in a total solid, Preferably it is 1-60 mass%.

  Within the above range, the adhesion to the substrate is good, the permeability of the developer to the exposed area is moderate, and the surface smoothness and sensitivity of the pixels are good.

[(E) Polymerizable monomer]
The colored resin composition of the present invention preferably contains (E) a polymerizable monomer.
(E) The polymerizable monomer is not particularly limited as long as it is a polymerizable low molecular compound, but it may be an addition-polymerizable compound having at least one ethylenic double bond (hereinafter referred to as “ethylenic compound”) Is preferred).

The ethylenic compound is a compound having an ethylenic double bond that undergoes addition polymerization and cures by the action of a photopolymerization initiation component described later when the colored resin composition of the present invention is irradiated with actinic rays. In addition, the (E) polymerizable monomer in this invention means the concept opposite to what is called a polymeric substance, and also includes a dimer, a trimer, and an oligomer other than a monomer in a narrow sense.
(E) Examples of the ethylenic compound in the polymerizable monomer include unsaturated carboxylic acids such as (meth) acrylic acid; esters of monohydroxy compounds and unsaturated carboxylic acids; aliphatic polyhydroxy compounds and unsaturated carboxylic acids; Esters of aromatic polyhydroxy compounds and unsaturated carboxylic acids; Esterification of unsaturated carboxylic acids with polyvalent carboxylic acids and polyhydric hydroxy compounds such as aliphatic polyhydroxy compounds and aromatic polyhydroxy compounds described above An ester obtained by the reaction; an ethylenic compound having a urethane skeleton obtained by reacting a polyisocyanate compound and a (meth) acryloyl group-containing hydroxy compound;

  Esters of aliphatic polyhydroxy compounds and unsaturated carboxylic acids include ethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, trimethylolethane tri (meth) acrylate , Pentaerythritol di (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) Examples include (meth) acrylic acid esters such as acrylate and glycerol (meth) acrylate. In addition, the (meth) acrylic acid portion of these (meth) acrylic acid esters is replaced with an itaconic acid portion, a crotonic acid portion replaced with a crotonic acid portion, or a maleic acid ester replaced with a maleic acid portion, etc. Is mentioned.

Examples of the ester of an aromatic polyhydroxy compound and an unsaturated carboxylic acid include hydroquinone di (meth) acrylate, resorcin di (meth) acrylate, pyrogallol tri (meth) acrylate, and the like.
The ester obtained by the esterification reaction of an unsaturated carboxylic acid with a polyvalent carboxylic acid and a polyvalent hydroxy compound may be a single substance or a mixture. Representative examples are condensates of (meth) acrylic acid, phthalic acid, and ethylene glycol; condensates of (meth) acrylic acid, maleic acid, and diethylene glycol; condensation of (meth) acrylic acid, terephthalic acid, and pentaerythritol A condensate of (meth) acrylic acid, adipic acid, butanediol, and glycerin.

  Examples of the ethylenic compound having a urethane skeleton obtained by reacting a polyisocyanate compound and a (meth) acryloyl group-containing hydroxy compound include aliphatic diisocyanates such as hexamethylene diisocyanate and trimethylhexamethylene diisocyanate; alicyclic rings such as cyclohexane diisocyanate and isophorone diisocyanate. Formula diisocyanates; aromatic diisocyanates such as tolylene diisocyanate and diphenylmethane diisocyanate, and (meth) acryloyl such as 2-hydroxyethyl (meth) acrylate and 3-hydroxy [1,1,1-tri (meth) acryloyloxymethyl] propane A reaction product with a group-containing hydroxy compound is exemplified.

In addition, examples of the ethylenic compound used in the present invention include (meth) acrylamides such as ethylene bis (meth) acrylamide; allyl esters such as diallyl phthalate; vinyl group-containing compounds such as divinyl phthalate. .
Among these, esters of aliphatic polyhydroxy compounds and unsaturated carboxylic acids are preferred, pentaerythritol or (meth) acrylic acid esters of dipentaerythritol are more preferred, and dipentaerythritol hexa (meth) acrylate is particularly preferred.

  The ethylenic compound may be a monomer having an acid value. The monomer having an acid value is, for example, an ester of an aliphatic polyhydroxy compound and an unsaturated carboxylic acid, and a non-aromatic carboxylic acid anhydride is reacted with an unreacted hydroxyl group of the aliphatic polyhydroxy compound. A polyfunctional monomer having a group is preferable, and in this ester, the aliphatic polyhydroxy compound is pentaerythritol and / or dipentaerythritol.

These monomers may be used alone, but since it is difficult to obtain a single compound in production, a mixture of two or more kinds may be used.
Moreover, you may use together the polyfunctional monomer which does not have an acid group, and the polyfunctional monomer which has an acid group as (E) polymeric monomer as needed.
A preferable acid value of the polyfunctional monomer having an acid group is 0.1 to 40 mg-KOH / g, and particularly preferably 5 to 30 mg-KOH / g.

When it is within the above range, the development and dissolution characteristics are hardly deteriorated, and the production and handling are easy. Furthermore, it is preferable because the photopolymerization performance is hardly lowered and the curability such as the surface smoothness of the pixel is good.
In the present invention, a more preferred polyfunctional monomer having an acid group is, for example, a mixture containing succinic acid ester of dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentaacrylate as a main component. It is also possible to use this polyfunctional monomer in combination with another polyfunctional monomer.

In the colored resin composition of the present invention, the content of these (E) polymerizable monomers is usually 1% by mass or more, preferably 5% by mass or more, more preferably 10% by mass or more in the total solid content. Moreover, it is 80 mass% or less normally, Preferably it is 70 mass% or less, More preferably, it is 50 mass% or less, Most preferably, it is 40 mass% or less.
The ratio of the (E) polymerizable monomer to the (A) dye is 1% by mass or more, preferably 5% by mass or more, more preferably 10% by mass or more, and particularly preferably 20% by mass or more. Moreover, it is 200 mass% or less normally, Preferably it is 100 mass% or less, More preferably, it is 80 mass% or less.

  Within the above range, photocuring is appropriate, poor adhesion during development is difficult to place, the cross-section after development is difficult to reverse taper, and further, peeling phenomenon and omission failure due to lower solubility are difficult to place. preferable.

[Other optional ingredients]
In addition to the above components, the colored resin composition of the present invention comprises a surfactant, an organic carboxylic acid and / or an organic carboxylic acid anhydride, a thermosetting compound, a plasticizer, a thermal polymerization inhibitor, a storage stabilizer, a surface It may contain a protective agent, an adhesion improver, a development improver, and the like. As these optional components, for example, various compounds described in JP-A-2007-113000 can be used. Moreover, when it contains the below-mentioned (F) pigment, you may contain a dispersing agent and a dispersing aid.

[(F) Pigment]
The colored resin composition of the present invention may contain (F) a pigment within a range not impairing the effects of the present invention for the purpose of improving the heat resistance of the obtained color filter.
(F) As a pigment, for example, when forming a pixel of a color filter, pigments of various colors such as blue and purple can be used. Examples of the chemical structure include organic pigments such as phthalocyanine, quinacridone, benzimidazolone, dioxazine, indanthrene, and perylene. In addition, various inorganic pigments can be used. Hereinafter, specific examples of usable pigments are indicated by pigment numbers.

  Examples of blue pigments include C.I. I. Pigment Blue 1, 1: 2, 9, 14, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36, 56, 56: 1, 60, 61, 61: 1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, 79 and the like.

Among these, a blue copper phthalocyanine pigment is preferable, and examples of the copper phthalocyanine pigment include C.I. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6 and the like are preferable, and C.I. I. Pigment Blue 15: 6.
For this reason, when the colored resin composition of this invention contains a blue pigment, it is 80 mass% or more with respect to the total content of a blue pigment, Especially 90 mass% or more, Especially 95-100 mass% is C.I. I. Pigment Blue 15: 6 is preferable.

Examples of purple pigments include C.I. I. Pigment Violet 1, 1: 1, 2, 2: 2, 3, 3: 1, 3: 3, 5, 5: 1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, 50 and the like.
Among these, a purple dioxazine pigment is preferable, and as the dioxazine pigment, C.I. I. Pigment Violet 19 and 23 are preferable, and C.I. I. Pigment Violet 23.

For this reason, when the colored resin composition of this invention contains a purple pigment, it is 80 mass% or more with respect to the total content of a purple pigment, Especially 90 mass% or more, Especially 95-100 mass% is C.I. I. Pigment Violet 23 is preferable.
These may be used alone or in a combination of two or more in any combination and ratio.

The (F) pigment used in the colored resin composition of the present invention preferably has a small average primary particle diameter from the viewpoint of forming a high-contrast pixel. Specifically, the average primary particle diameter is 40 nm or less. Is preferable, and it is more preferable that it is 35 nm or less.
Particularly for the blue copper phthalocyanine pigment, the average primary particle size is preferably 40 nm or less, more preferably 35 nm or less, and still more preferably 20 to 30 nm.

Moreover, about a dioxazine pigment, an average primary particle diameter becomes like this. Preferably it is 40 nm or less, More preferably, it is 25-35 nm. From the viewpoint that the pigment is less likely to aggregate in the colored resin composition, it is preferable that the average primary particle size is not too small.
Here, the average primary particle size of the (F) pigment is a value measured and calculated by the following method.

  First, (F) a pigment is ultrasonically dispersed in chloroform, dropped onto a collodion film-attached mesh, dried, and a primary particle image of the pigment is obtained by observation with a transmission electron microscope (TEM). From this image, the particle size of each pigment particle is determined for a plurality of (usually about 200 to 300) pigment particles, with the diameter corresponding to the area circle converted to the diameter of a circle having the same area.

Using the obtained primary particle size value, the number average value is calculated according to the following formula to obtain the average particle size.
The particle diameter of each pigment _{particle: X 1, X 2, X} 3, X 4, ····, X i, ······ X m

{Blending amount}
In this invention, when it contains (F) pigment, content of the pigment in a colored resin composition is 80 mass% or less normally in a total solid, Preferably it is 50 mass% or less.
Moreover, content with respect to 100 mass parts of said (A) dye is 2000 mass parts or less normally, Preferably it is 1000 mass parts or less.

By setting it within the above-mentioned range, it is preferable in that the heat resistance of the obtained pixel is likely to be better without greatly affecting the transmittance of the dye (A).
[Dispersant]
When the colored resin composition of the present invention contains (F) a pigment, it is preferable to further contain a dispersant.

The dispersant in the present invention is not particularly limited as long as the pigment is dispersed and can maintain stability.
For example, cationic, anionic, nonionic or amphoteric dispersants can be used, but polymer dispersants are preferred. Specific examples include block copolymers, polyurethanes, polyesters, alkylammonium salts or phosphate esters of polymer copolymers, and cationic comb graft polymers. Of these dispersants, block copolymers, polyurethanes, and cationic comb graft polymers are preferred. In particular, a block copolymer is preferable, and among these, a block copolymer composed of an A block having solvophilicity and a B block having a functional group containing a nitrogen atom is preferable.

Specifically, the B block having a nitrogen atom-containing functional group includes a unit structure having a quaternary ammonium base and / or an amino group in the side chain, while the solvophilic A block includes a quaternary ammonium. Examples include a unit structure having no base and amino group.
The B block constituting the acrylic block copolymer has a unit structure having a quaternary ammonium base and / or an amino group, and has a pigment adsorption function.

Further, when the B block has a quaternary ammonium base, the quaternary ammonium base may be directly bonded to the main chain, but may be bonded to the main chain via a divalent linking group. Good.
Examples of such block copolymers include those described in JP-A-2009-025813.

Moreover, the colored resin composition of the present invention may contain a dispersant other than those described above. Examples of other dispersants include those described in JP-A-2006-343648, for example.
When the colored resin composition of the present invention contains (F) a pigment, the content of the dispersant in the total solid content is 2 to 1000 parts by mass with respect to 100 parts by mass of the total content of (F) pigment, In particular, it is preferably used in a range of 5 to 500 parts by mass, particularly 10 to 250 parts by mass.

  By setting it within the above range, (A) it is preferable in that good pigment dispersibility can be ensured without affecting the heat resistance of the dye, and the pigment dispersion stability becomes better.

[Dispersion aid]
The colored resin composition of the present invention may contain a dispersion aid. The dispersion aid here may be a pigment derivative. Examples of the pigment derivative include JP-A Nos. 2001-220520, 2001-271004, 2002-179976, and 2007-. Various compounds described in Japanese Patent Application Publication No. 113000 and Japanese Patent Application Publication No. 2007-186681 can be used.

  The content of the dispersion aid in the colored resin composition of the present invention is usually 0.1% by mass or more, usually 30% by mass or less, preferably 20% by mass or less, based on the total solid content of the pigment. Preferably it is 10 mass% or less, More preferably, it is 5 mass% or less. By controlling the addition amount within the above range, it is preferable in that the effect as a dispersion aid is exhibited and the dispersibility and dispersion stability are better.

[Dispersion resin]
The colored resin composition of the present invention may contain a part or all of the resin selected from the (C) binder resin or other binder resins as the following dispersion resin.
Specifically, in [Preparation Method of Colored Resin Composition], which will be described later, by adding (C) binder resin together with the components such as the above-mentioned dispersant, the (C) binder resin is combined with the dispersant. It contributes to the dispersion stability of the pigment (F) by a synergistic effect. As a result, the amount of dispersant added may be reduced, which is preferable. Further, it is preferable because the developability is improved, the undissolved matter does not remain in the non-pixel portion of the substrate, and the adhesion of the pixel to the substrate is improved.

  Thus, the (C) binder resin used in the dispersion treatment step may be referred to as a dispersion resin. The dispersion resin is preferably used in an amount of about 0 to 200% by weight, more preferably about 10 to 100% by weight, based on the total amount of the pigment in the colored resin composition.

[Preparation Method of Colored Resin Composition]
In the present invention, the colored resin composition can be prepared by an appropriate method. For example, (A) a dye containing compound (I), (C) a binder resin, and (D) light containing compound (II). The polymerization initiating component can be prepared by mixing with (B) a solvent and optional components used as necessary.

  In addition, as a preparation method in the case of containing (F) a pigment, in the solvent containing (F) pigment, in the presence of a dispersing agent and a dispersing aid to be added if necessary, (C) a binder resin may be used. A pigment dispersion liquid is prepared by mixing and dispersing together with the parts, for example, using a paint shaker, sand grinder, ball mill, roll mill, stone mill, jet mill, homogenizer, and the like. In the pigment dispersion, (A) a dye containing compound (I), (C) a binder resin, (D) a photopolymerization initiation component containing compound (II), and (E) a polymerizable monomer as necessary. The method of preparing by adding and mixing can be mentioned.

[Application of colored resin composition]
The colored resin composition of the present invention is usually in a state where all the constituent components are dissolved or dispersed in a solvent. Such a colored resin composition is supplied onto a substrate to form components such as a color filter, a liquid crystal display device, and an organic EL display device.
Hereinafter, as an application example of the colored resin composition of the present invention, an application as a pixel of a color filter, a liquid crystal display device (panel) and an organic EL display device using them will be described.

<Color filter>
The color filter of the present invention has a pixel formed from the colored resin composition of the present invention.
The method for forming the color filter of the present invention will be described below.
The pixel of the color filter can be formed by various methods. Here, although the case where it forms by the photolithographic method using a photopolymerizable colored resin composition is demonstrated to an example, a manufacturing method is not limited to this.

  First, on the surface of the substrate, if necessary, a black matrix is formed so as to partition a portion for forming pixels, and after applying the colored resin composition of the present invention on this substrate, pre-baking is performed. The solvent is evaporated to form a coating film. Then, after exposing this coating film through a photomask, developing with an alkali developer, dissolving and removing the unexposed portion of the coating film, and then post-baking, each of red, green, and blue A color filter can be manufactured by forming a pixel pattern.

In the present invention, it is particularly preferable that the pixel formed using the colored resin composition of the present invention is a blue pixel.
The substrate used for forming the pixels is not particularly limited as long as it is transparent and has an appropriate strength. For example, polyester resin, polyolefin resin, polycarbonate resin, acrylic resin, thermoplastic resin Examples thereof include a sheet made, an epoxy resin, a thermosetting resin, and various glasses.

In addition, these substrates may be appropriately subjected to pretreatment as desired, such as thin film formation treatment with a silane coupling agent or urethane resin, surface treatment such as corona discharge treatment or ozone treatment, if desired.
When applying the colored resin composition to the substrate, a spinner method, a wire bar method, a flow coating method, a slit and spin method, a die coating method, a roll coating method, a spray coating method, and the like can be given. Of these, the slit and spin method and the die coating method are preferable.

The thickness of the coating film is usually 0.2 to 20 μm, preferably 0.5 to 10 μm, particularly preferably 0.8 to 5.0 μm as the film thickness after drying.
Within the above range, it is preferable in that the gap can be easily adjusted in the pattern development or liquid crystal cell forming step, and a desired color can be easily expressed.
As the radiation used in the exposure, for example, visible light, ultraviolet light, far ultraviolet light, electron beam, X-ray or the like can be used, and radiation having a wavelength in the range of 190 to 450 nm is preferable.

  The light source used for image exposure for using radiation having a wavelength of 190 to 450 nm is not particularly limited. Lamp light sources such as medium pressure mercury lamp, low pressure mercury lamp, carbon arc, fluorescent lamp; laser light sources such as argon ion laser, YAG laser, excimer laser, nitrogen laser, helium cadmium laser, semiconductor laser, and the like. An optical filter can also be used when used by irradiating light of a specific wavelength.

Exposure of radiation, 10~10,000J / m ² is preferred. Examples of the alkaline developer include sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate, sodium silicate, potassium silicate, sodium metasilicate, sodium phosphate, Inorganic alkaline compounds such as potassium phosphate, sodium hydrogen phosphate, potassium hydrogen phosphate, sodium dihydrogen phosphate, potassium dihydrogen phosphate, ammonium hydroxide; mono-di- or tri-ethanolamine, mono-di-, or tri -Methylamine, mono-, di-, or tri-ethylamine, mono-, or di-isopropylamine, n-butylamine, mono-, di-, or tri-isopropanolamine, ethyleneimine, ethylenediimine, tetramethylammonium Hydroxide (TMAH) Aqueous solution of an organic alkaline compound choline are preferred.

An appropriate amount of a water-soluble organic solvent such as isopropyl alcohol, benzyl alcohol, ethyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol, diacetone alcohol, or the like can be added to the alkali developer. In addition, it is usually washed with water after alkali development.
As the development processing method, any method such as an immersion development method, a spray development method, a brush development method, and an ultrasonic development method can be used. The development conditions are preferably 5 to 300 seconds at room temperature (23 ° C.).

There are no particular restrictions on the conditions of the development processing, but the development temperature is usually 10 ° C. or higher, especially 15 ° C. or higher, more preferably 20 ° C. or higher, and usually 50 ° C. or lower, especially 45 ° C. or lower, more preferably 40 ° C. or lower. Is preferred.
The developing method can be any one of immersion developing method, spray developing method, brush developing method, ultrasonic developing method and the like.

  When the color filter thus produced is used in a liquid crystal display device, a transparent electrode such as ITO is formed on the image as it is and used as a part of a component such as a color display or a liquid crystal display device. Although used, in order to improve surface smoothness and durability, a top coat layer such as polyamide or polyimide can be provided on the image as necessary. Further, in some applications such as a planar alignment type drive system (IPS mode), the transparent electrode may not be formed. In the vertical alignment type driving method (MVA mode), ribs may be formed. Further, a column structure (photo spacer) by a photolithography method may be formed instead of the bead dispersion type spacer.

<Liquid crystal display device>
The liquid crystal display device of the present invention uses the above-described color filter of the present invention. There is no restriction | limiting in particular about the model and structure of the liquid crystal display device of this invention, It can assemble in accordance with a conventional method using the color filter of this invention.
For example, the liquid crystal display device of the present invention can be formed by the method described in “Liquid Crystal Device Handbook” (Nikkan Kogyo Shimbun, September 29, 1989, Japan Society for the Promotion of Science 142nd Committee).

<Organic EL display device>
When producing an organic EL display device having the color filter of the present invention, for example, as shown in FIG. 1, on a blue color filter in which pixels 20 are formed on a transparent support substrate 10 by the colored resin composition of the present invention. A multicolor organic EL element is manufactured by laminating the organic light-emitting body 500 through the organic protective layer 30 and the inorganic oxide film 40.

  As a method for laminating the organic light emitter 500, a transparent anode 50, a hole injection layer 51, a hole transport layer 52, a light emitting layer 53, an electron injection layer 54, and a cathode 55 are sequentially formed on the upper surface of the color filter. The organic light-emitting body 500 formed on another substrate may be bonded to the inorganic oxide film 40. The organic EL element 100 manufactured as described above can be applied to both a passive drive type organic EL display device and an active drive type organic EL display device.

EXAMPLES Next, although an Example and a comparative example demonstrate this invention further more concretely, this invention is not limited to description of a following example, unless the summary is exceeded.
[Synthesis of photopolymerization initiator]
(Reference Synthesis Example 1: Compound (II-A))

  The compound (II-A) was synthesized according to the following procedure in accordance with the method described in JP-A-2008-179611.

Under a nitrogen atmosphere, the above compound 1 (0.98 g, 5 mmol) and methylene chloride (17 mL) were added to a 50 ml three-necked flask. After cooling this to 3 ° C., o-toluoyl chloride (0.77 g, 5 mmol) was added dropwise. To this, aluminum chloride (0.67 g, 5 mmol) was slowly added over 1 hour. After completion of the addition, the mixture was further stirred at 3 ° C. for 2 hours, and methylene chloride (8 mL) was added. Next, glutaric anhydride (0.68 g, 6 mmol) was added over 30 minutes, and then aluminum chloride (1.90 g, 14 mmol) was added over 30 minutes.
After completion of the addition, the mixture was further stirred at 3 ° C. for 2 hours, and the reaction solution was poured into ice water (400 mL) little by little. Sodium chloride (80 g) was added to the aqueous layer, and extraction was performed 5 times with methylene chloride (50 mL). The organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. After filtration of anhydrous magnesium sulfate, the solvent was distilled off by an evaporator to obtain the above compound 2 (2.13 g, crude yield 100%). This was used in the next reaction without purification.

Under a nitrogen atmosphere, the above compound 2 (2.13 g, 5 mmol), methanol (22 mL) and concentrated sulfuric acid (5 mg) were placed in a 50 ml three-necked flask and heated under reflux for 3 hours. After cooling, the solvent was concentrated and water (10 mL) and ethyl acetate (30 mL) were added.
The organic layer was washed sequentially with a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. After filtering anhydrous magnesium sulfate, the solvent was distilled off by an evaporator to obtain the compound 3 (1.72 g, crude yield 78%). This was used in the next reaction without purification.

  In a nitrogen atmosphere, the above compound 3 (1.00 g, 2.26 mmol) and methylene chloride (10 mL) were placed in a 50 mL three-necked flask and cooled to 10 ° C. To this was added 1N hydrogen chloride in diethyl ether (4.68 mL). Next, amyl nitrite (0.36 g, 3.04 mmol) was added and reacted at 10 ° C. for 4 hours. After adding water (10 mL), it wash | cleaned in order with saturated sodium hydrogencarbonate aqueous solution and saturated sodium chloride aqueous solution, and anhydrous magnesium sulfate was added and it dried. After filtering anhydrous magnesium sulfate, the solvent was distilled off by an evaporator to obtain a pale yellow solid (0.88 g). This was recrystallized and purified with toluene (3.5 mL) to obtain the compound 4 (0.45 g, yield 42%). The isomer ratio analyzed by HPLC was anti: syn = 99: 1.

  In a nitrogen atmosphere, the above compound 5 (3.50 g, 7.44 mmol) and methylene chloride (35 mL) were placed in a 50 mL three-necked flask and cooled to 4 ° C. To this was added triethylamine (1.50 g, 14.9 mmol). Next, acetyl chloride (0.70 g, 8.93 mmol) was added, and the reaction was allowed to proceed for 1 hour. After adding a saturated aqueous sodium hydrogen carbonate solution (10 mL), the organic layer was separated, washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution in that order, and dried over anhydrous magnesium sulfate. After anhydrous magnesium sulfate was filtered off, the solvent was distilled off by an evaporator to obtain a yellow oil (3.65 g). This was purified by column chromatography (ethyl acetate / hexane = 1/1) to obtain the compound 5 (3.12 g, yield 82%). The isomer ratio analyzed by HPLC was anti-isomer: syn-isomer = 98: 2.

¹ H-NMR δ [ppm] (CDCl ₃ ) of Compound 5 (Compound (II-A))
1.49 (t, 3H), 2.29 (s, 3H), 2.36 (s, 3H), 2.73 (t, 2H), 3.14 (t, 2H), 3.60 (s , 3H), 4.43 (q, 2H), 7.3 to 7.5 (m, 6H), 8.06 (dd, 1H), 8.29 (dd, 1H), 8.59 (d, 1H), 8.83 (dd, 1H)

[Synthesis of dyes]
(Reference Synthesis Example 2: Synthesis of Dye (IA))
25 g of Acid Red 52 (manufactured by Tokyo Chemical Industry Co., Ltd.) was dissolved in 250 mL of water and dialyzed until no chloride ion was detected with an electrodialyzer. This solution was ion-exchanged with a cation exchange resin SK1BH (manufactured by Mitsubishi Chemical Corporation). The obtained aqueous solution was neutralized with an aqueous solution of lithium hydroxide monohydrate until the pH became 7.0, then concentrated, dried, and a dye represented by the following formula (IA) (I-A) A) was synthesized.

  This dye (IA) was a red pigment having a maximum absorption wavelength λmax of 533 nm.

[Synthesis of resin]
(Reference Synthesis Example 3: Synthesis of Resin A)
145 parts by mass of propylene glycol monomethyl ether acetate was stirred while replacing with nitrogen, and the temperature was raised to 120 ° C. Here, 5.2 parts by mass of styrene, 132 parts by mass of glycidyl methacrylate, 4.4 parts by mass of monoacrylate FA-513M (manufactured by Hitachi Chemical Co., Ltd.) having a tricyclodecane skeleton, and 2.2′-azobis-2-methylbutyrate A mixture of 8.47 parts by mass of nitrile was added dropwise over 3 hours, and the mixture was further stirred at 90 ° C. for 2 hours. Next, the inside of the reaction vessel was changed to air substitution, 1.1 parts by mass of trisdimethylaminomethylphenol and 0.19 parts by mass of hydroquinone were added to 67.0 parts by mass of acrylic acid, and the reaction was continued at 100 ° C. for 12 hours. Then, 15.2 parts by mass of tetrahydrophthalic anhydride (THPA) and 0.2 parts by mass of triethylamine were added and reacted at 100 ° C. for 3.5 hours. The weight average molecular weight Mw measured by GPC of the resin A thus obtained was about 9000 acid value of 25 mg-KOH / g.

[Preparation of pigment dispersion]
As a blue pigment, C.I. I. Pigment Blue 15: 6 is 11.36 parts by mass, 57.5 parts by mass of propylene glycol monomethyl ether acetate as a solvent, 3.02 parts by mass in terms of solid content, Dispersic 2000 manufactured by Big Chemie, and 0.5 mm in diameter 215.7 parts by weight of zirconia beads were filled in a stainless steel container and dispersed with a paint shaker for 6 hours to prepare a blue pigment dispersion (1).

[Preparation of colored resin composition]
Using the dye (IA) and the blue pigment dispersion (1) obtained in [Synthesis of Dye], other components are mixed so as to have the composition described in Table 1, and a colored resin composition Was prepared.
In Table 1, the upper numerical value represents the mass part of each component to be added, and the lower numerical value represents the content ratio (mass%) of each component with respect to the total solid content.
In mixing, the mixture was stirred for 1 hour or longer, and finally filtered through a 5 μm piece filter to remove foreign matters.

Moreover, each compound in Table 1 is as follows.
OXE-01: 1- [4- (phenylthio) phenyl] -1,2-octanedione 2- (O-benzoyloxime)
DPHA: Dipentaerythritol hexaacrylate PGMEA: Propylene glycol monomethyl ether acetate PGME: Propylene glycol monomethyl ether

[Production of colored resin film and evaluation of brightness]
On the glass substrate cut into 5 cm square, the above-mentioned colored resin composition was baked at 230 ° C. for 20 minutes by a spin coating method in a clean oven, and the sy in the XYZ color system when C light source was applied was 0. The coating was applied to 0.086 and dried under reduced pressure. Thereafter, the entire surface was exposed at an exposure amount of 60 mJ / cm ² , and then baked at 230 ° C. for 20 minutes in a clean oven. Then, the spectral transmittance was measured with a spectrophotometer U-3310 (manufactured by Hitachi, Ltd.). The chromaticity (C light source) in the color system was calculated and the luminance was compared. The results are summarized in Table 2. It was confirmed that the colored resin film of Example 1 had a luminance equivalent to that of Comparative Example 1.

[Evaluation of sensitivity]
On the glass substrate cut into 5 cm square, the above-mentioned colored resin composition was baked at 230 ° C. for 20 minutes by a spin coating method in a clean oven, and the sy in the XYZ color system when C light source was applied was 0. The coating was applied to 0.086 and dried under reduced pressure. Thereafter, the film was exposed through a line-and-space mask (mask size 50 μm) at an exposure amount of 60 mJ / cm ² , and then sodium carbonate 1.7%, sodium bicarbonate 0.3% and nonionic surfactant 0. Spray development was carried out for 40 seconds at a developer temperature of 23 ° C. and a pressure of 0.25 MPa using an aqueous carbonate developer in which a 12% aqueous carbonate developer was adjusted to pH = 10. The developed substrate was baked at 230 ° C. for 30 minutes in a clean oven, and the line width was measured using an optical microscope and an image processing apparatus. The results are summarized in Table 3.

As shown in Table 3, in the colored resin composition containing the xanthene compound (I), the pattern after development was not formed in the composition of Comparative Example 1, whereas the pattern was formed in the colored resin composition of the present application. ing.
That is, it can be seen that the colored resin composition of the present application is more sensitive than Comparative Example 1.
As described above, as shown in Tables 2 and 3, the colored resin composition of the present invention has greatly improved the sensitivity of the colored resin composition while maintaining the luminance of the obtained pixel.

  A color filter having pixels formed using the colored resin composition of the present invention, and a liquid crystal display device and an organic EL display device including the color filter are of high quality.

DESCRIPTION OF SYMBOLS 100 Organic EL element 20 Pixel 30 Organic protective layer 40 Inorganic oxide film 500 Organic light-emitting body 51 Hole injection layer 54 Electron injection layer

Claims (7)

(A) a dye, (B) a solvent and (C) a binder resin and (D) a photopolymerization initiating component,
(A) the dye contains a xanthene compound represented by the following formula (I), and
(D) A colored resin composition, wherein the photopolymerization initiation component contains a compound represented by the following formula (II).

(In the formula (I),
R ^{1 to} R ⁴ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 10 carbon atoms, or an optionally substituted aromatic hydrocarbon having 6 to 18 carbon atoms. Represents a cyclic group.
R ¹ and R ² , and R ³ and R ⁴ may be independently bonded to each other to form a ring, and the ring may have a substituent.
R ⁵ and R ⁶ each independently represent a hydrogen atom, a halogen atom or an alkyl group having 1 to 10 carbon atoms which may have a substituent.
R ⁷ represents an arbitrary substituent.
m represents an integer of 0 to 5. When m is an integer of 2 or more, the plurality of R ⁷ may be the same or different.
p represents an integer of 1 to 4. When p is 2 to 4, the structures in [] containing a plurality of xanthene skeletons may be the same or different.
X ^q− represents an arbitrary q-valent anion.
q represents the integer of 1-4.
n represents an integer of 0 to 4. When n is 2 to 4, the plurality of X ^q− may be the same or different.
When R ^{1 to} R ⁷ are a group containing a sulfonate group or a carboxylate group, or when R ⁷ is a sulfonate group or a carboxylate group, n is 0 and p = 1, otherwise , P = n × q. )

(In the above formula (II),
Z represents an aromatic ring group which may have a substituent.
m represents an integer of 0 to 20.
X is one group selected from the group consisting of —CR ⁹⁴ R ⁹⁵ —, —C (═CR ⁹⁶ R ⁹⁷ ) —, —CR ⁹⁸ ═CR ⁹⁹ — and —C≡C—, or a combination of two or more thereof. Represents a group consisting of R ^{96 to} R ⁹⁹ each independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R ⁹⁴ and R ⁹⁵ , R ¹⁰¹ and R ¹⁰² each independently represents an arbitrary substituent.
R ¹⁰¹ may be bonded to Z to form a ring, and the ring may have a substituent.
R ¹⁰³ represents an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 3 to 5 carbon atoms, or an aryl group having 6 to 20 carbon atoms,
R ¹⁰⁴ to R ¹⁰⁹ each independently represents a hydrogen atom, a halogen atom, a nitro group, an alkyl group or an alkoxy group having 1 to 20 carbon atoms having 1 to 6 carbon atoms. )   The content of the compound represented by the formula (II) is 0.4 mass times or more and 30 mass times or less with respect to the total solid content of the dye (A). The colored resin composition as described.   The colored resin composition according to claim 1, further comprising (E) a polymerizable monomer.   The colored resin composition according to any one of claims 1 to 3, further comprising (F) a pigment.   It has a pixel formed using the colored resin composition as described in any one of Claims 1-4, The color filter characterized by the above-mentioned.   A liquid crystal display device comprising the color filter according to claim 5.   An organic EL display device comprising the color filter according to claim 5.

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