JP2012167153A - Curable colored composition, color filter and method for producing the same, liquid crystal display, solid-state image sensor, and pigment compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a curable colored composition excellent in heat resistance which transmits magenta region light and absorbs cyan region light.SOLUTION: This curable colored composition contains a pigment compound expressed by general formula (wherein Z represents nitrogen or -C(R)-; Rrepresents aryl, alkyl, cyano, hydrogen or the like; Qrepresents nitrogen or -C(R)-; Qrepresents nitrogen or -C(R)-; and Y represents an atom or atom group constituting an anion).

Description

  The present invention relates to a curable coloring composition, a color filter using the curable coloring composition and a manufacturing method thereof, a liquid crystal display device and a solid-state imaging device using the curable coloring composition, and the curable coloring composition. The present invention relates to a dye compound used for a product.

  Conventionally, a color filter is made into a colored composition by containing a pigment dispersion composition in which an organic pigment or an inorganic pigment is dispersed, a polyfunctional monomer, a polymerization initiator, an alkali-soluble resin, and other components as necessary. This is used to form a colored pattern by a photolithography method, an ink jet method or the like.

  In recent years, color filters tend to be used not only for monitors but also for televisions (TVs) in liquid crystal display (LCD) applications. Along with this trend of expanding applications, color filters are required to have high color characteristics in terms of chromaticity and contrast. Similarly, color filters for image sensors (solid-state imaging devices) are required to further improve color characteristics such as reduction of color unevenness and improvement of color resolution.

  However, in the conventional pigment dispersion system, problems such as the occurrence of scattering due to coarse particles of the pigment and the increase in viscosity due to poor dispersion stability are likely to occur, and it is often difficult to further improve the contrast and brightness.

  Therefore, conventionally, as a coloring material, use of not only a pigment but also a dye has been studied (for example, see Patent Document 1). When a dye is used as a colorant, the hue and brightness of a display image when an image is displayed can be increased due to the color purity of the dye itself and the vividness of the hue, and contrast can be improved because coarse particles are eliminated. It is useful in terms.

  As examples of dyes, compounds having a wide variety of dye bases such as arylmethane dyes, dipyrromethene dyes, pyrimidineazo dyes, pyrazole azo dyes, xanthene dyes are known (for example, Patent Documents 2 to 2). 4). As for arylmethane dyes, application examples to blue color filters are known (see, for example, Patent Documents 5 to 8).

JP-A-6-75375 JP 2008-292970 A JP 2007-039478 A Japanese Patent No. 3387541 JP 2008-304766 A JP 2010-204132 A JP 2010-83912 A JP 2010-256598 A

However, when an arylmethane dye provided in the past is assumed to be used as a green color filter, the cyan dye has a short wavelength of absorption, and there is a problem that its utility is greatly limited. In addition, arylmethane dyes are often poor in heat resistance, and there are problems such as being restricted by the heating process when manufacturing products using dyes, and problems with durability of products using dyes. there were.
The present invention has been made in view of the above-described problems of the prior art, has a heat resistance, a colored composition that transmits light in the magenta region and absorbs light in the cyan region, a color filter, and a manufacturing method thereof Another object of the present invention is to provide a liquid crystal display device and a solid-state imaging device in which the color of a display image is vivid and exhibits high contrast.

  As a result of diligent investigations, the present inventors have found that if a dye compound having a specific structure is used, it has excellent heat resistance while having an arylmethane structure, and transmits light in the magenta region and transmits light in the cyan region. It has been found that a curable coloring composition having a preferable absorption wavelength characteristic of absorbing can be provided, and the present invention has been provided. That is, the following present invention is provided as specific means for achieving the above-described problems. In addition, the broken line which exists in the general formula described below means that the cyclic structure may be formed.

［一般式（Ａ）において、Ｚは、窒素原子、または−Ｃ（Ｒ¹）−を表す。Ｒ¹は、置換基を有していても良いアリール基、ハロゲン原子が置換していても良いアルキル基、シアノ基、水素原子、または置換基を有していてもよい芳香族環を表す。Ｑ¹は、窒素原子、または−Ｃ（Ｒ¹⁴）−を表す。Ｑ²は、窒素原子、または−Ｃ（Ｒ²⁴）−を表す。Ｒ²、Ｒ³、Ｒ⁴およびＲ⁵は、それぞれ独立に、置換基を有していても良いアリール基、置換基を有していても良いアルキル基、または水素原子を表す。Ｒ¹¹、Ｒ¹³、Ｒ¹⁴、Ｒ²¹、Ｒ²²、Ｒ²³およびＲ²⁴は、それぞれ独立に置換基を表す。Ｒ²、Ｒ³、Ｒ⁴およびＲ⁵は、それぞれＲ¹²、Ｒ¹³、Ｒ²²、Ｒ²³と一緒になって、それぞれ独立に置換基を有していても良いアルキレン基、置換基を有していても良いビニレン基、または置換基を有していても良いプロペニレン基を形成していてもよい。Ｙは、アニオンを構成する原子または原子団を表す。また、一般式（Ａ）は下記の（１）〜（７）のいずれか１つの条件を満たす。 <1> A curable coloring composition comprising a dye compound represented by the following general formula (A).

[In General Formula (A), Z represents a nitrogen atom or -C (R < ¹ >)-. R ¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group, a hydrogen atom, or an aromatic ring which may have a substituent. Q ¹ represents a nitrogen atom or —C (R ¹⁴ ) —. Q ² represents a nitrogen atom or —C (R ²⁴ ) —. R ² , R ³ , R ⁴ and R ⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ¹¹ , R ¹³ , R ¹⁴ , R ²¹ , R ²² , R ²³ and R ²⁴ each independently represent a substituent. R ² , R ³ , R ⁴ and R ⁵ together with R ¹² , R ¹³ , R ²² and R ²³ each have an alkylene group or a substituent which may have a substituent independently. A vinylene group which may be substituted, or a propenylene group which may have a substituent may be formed. Y represents an atom or an atomic group constituting an anion. The general formula (A) satisfies any one of the following conditions (1) to (7).

(1) Z represents —C (R ¹ ) —. R ¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group or a hydrogen atom. Q ¹ represents —C (R ¹⁴ ) —. Q ² represents —C (R ²⁴ ) —. R ² together with R ¹² represents an alkylene group which may have a substituent, a vinylene group which may have a substituent, or a propenylene group which may have a substituent. R ³ , R ⁴ and R ⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ³ , R ⁴ and R ⁵ together with R ¹³ , R ²² and R ²³ are each independently an alkylene group which may have a substituent, or vinylene which may have a substituent. A propenylene group which may have a group or a substituent may be formed.

(2) Z represents —C (R ¹ ) —. R ¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group or a hydrogen atom. Q ¹ represents —C (R ¹⁴ ) —. Q ² represents —C (R ²⁴ ) —. R ¹⁴ and R ²⁴ together represent a methylene group optionally having a substituent, —O—, —SO ₂ —, or a silylene group optionally having a substituent. R ² together with R ¹² represents an alkylene group which may have a substituent, a vinylene group which may have a substituent, or a propenylene group which may have a substituent. R ³ , R ⁴ and R ⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ³ , R ⁴ and R ⁵ together with R ¹³ , R ²² and R ²³ are each independently an alkylene group which may have a substituent, or vinylene which may have a substituent. A propenylene group which may have a group or a substituent may be formed.

(3) Z represents —C (R ¹ ) —. R ¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group or a hydrogen atom. Q ¹ represents —C (R ¹⁴ ) —. Q ² represents —C (R ²⁴ ) —. R ¹⁴ and R ²⁴ together represent —SO ₂ —. R ² , R ³ , R ⁴ and R ⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ² , R ³ , R ⁴ and R ⁵ together with R ¹² , R ¹³ , R ²² and R ²³ each have an alkylene group or a substituent which may have a substituent independently. A vinylene group which may be substituted, or a propenylene group which may have a substituent may be formed.

(4) Z represents a nitrogen atom. Q ¹ represents —C (R ¹⁴ ) —. Q ² represents —C (R ²⁴ ) —. R ¹⁴ and R ²⁴ together represent a methylene group optionally having a substituent, —O—, —SO ₂ —, or a silylene group optionally having a substituent. R ² represents an alkylene group which may have a substituent, a vinylene group which may have a substituent, or a propenylene group which may have a substituent. R ³ , R ⁴ and R ⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ³ , R ⁴ and R ⁵ together with R ¹³ , R ²² and R ²³ are each independently an alkylene group which may have a substituent, or vinylene which may have a substituent. A propenylene group which may have a group or a substituent may be formed.

(5) Z represents —C (R ¹ ) —. R ¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group or a hydrogen atom. Q ¹ and Q ² represent a nitrogen atom. R ² , R ³ , R ⁴ and R ⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ² , R ³ , R ⁴ and R ⁵ together with R ¹² , R ¹³ , R ²² and R ²³ each have an alkylene group or a substituent which may have a substituent independently. A vinylene group which may be substituted, or a propenylene group which may have a substituent may be formed.

(6) Z represents —C (R ¹ ) —. R ¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group or a hydrogen atom. Q ¹ and Q ² represent nitrogen atoms, and these nitrogen atoms are bonded to an atomic group represented by> M- [L] n. M represents a metal atom. L represents a ligand. n represents any natural number of 1 to 4. R ² , R ³ , R ⁴ and R ⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ² , R ³ , R ⁴ and R ⁵ together with R ¹² , R ¹³ , R ²² and R ²³ each have an alkylene group or a substituent which may have a substituent independently. A vinylene group which may be substituted, or a propenylene group which may have a substituent may be formed.

(7) Z represents -C (R < ¹ >)-. R ¹ represents an aromatic ring substituted with —N (R ³¹ ) (R ³² ). Q ¹ represents —C (R ¹⁴ ) —. Q ² represents —C (R ²⁴ ) —. At least one combination of R ¹¹ and R ¹² , R ¹² and R ² , R ¹² and R ³ , R ³ and R ¹³ , and R ¹³ and R ¹⁴ together forms an aromatic ring. Represents the atomic group necessary for. At least one combination of R ²¹ and R ²² , R ²² and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ²³ , and R ²³ and R ²⁴ together forms an aromatic ring. Represents the atomic group necessary for. R ² , R ³ , R ⁴ , R ⁵ , R ³¹ and R ³² are each independently an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom Represents. ]

［一般式（１）において、Ｒ¹⁰¹は、置換基を有していても良いアリール基、ハロゲン原子が置換していても良いアルキル基、シアノ基、または水素原子を表す。Ｒ¹⁰²は、置換基を有していても良いアルキレン基、置換基を有していても良いビニレン基、または置換基を有していても良いプロペニレン基を表す。Ｒ¹⁰³、Ｒ¹⁰⁴およびＲ¹⁰⁵は、それぞれ独立に、置換基を有していても良いアリール基、置換基を有していても良いアルキル基、または水素原子を表す。Ｒ¹¹¹、Ｒ¹¹³、Ｒ¹¹⁴、Ｒ¹²¹、Ｒ¹²²、Ｒ¹²³およびＲ¹²⁴は、それぞれ独立に置換基を表す。Ｒ¹⁰³、Ｒ¹⁰⁴およびＲ¹⁰⁵は、それぞれＲ¹¹³、Ｒ¹²²、Ｒ¹²³と一緒になって、それぞれ独立に置換基を有していても良いアルキレン基、置換基を有していても良いビニレン基、または置換基を有していても良いプロペニレン基を形成していてもよい。Ｙは、アニオンを構成する原子または原子団を表す。］ <2>
A curable coloring composition comprising a dye compound represented by any one of the following general formulas (1) to (7).

[In General Formula (1), R ¹⁰¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group or a hydrogen atom. ^R102 represents an alkylene group which may have a substituent, a vinylene group which may have a substituent, or a propenylene group which may have a substituent. R ¹⁰³ , R ¹⁰⁴ and R ¹⁰⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ¹¹¹ , R ¹¹³ , R ¹¹⁴ , R ¹²¹ , R ¹²² , R ¹²³ and R ¹²⁴ each independently represent a substituent. R ¹⁰³ , R ¹⁰⁴ and R ¹⁰⁵ together with R ¹¹³ , R ¹²² and R ¹²³ are each independently an alkylene group which may have a substituent, or vinylene which may have a substituent. A propenylene group which may have a group or a substituent may be formed. Y represents an atom or an atomic group constituting an anion. ]

［一般式（２）において、Ｘ²⁰¹は、置換基を有していても良いメチレン基、−Ｏ−、−ＳＯ₂−、または置換基を有していても良いシリレン基を表す。Ｒ²⁰¹は、置換基を有していても良いアリール基、ハロゲンが置換基を有していても良いアルキル基、シアノ基、または水素原子を表す。Ｒ²⁰²は、置換基を有していても良いアルキレン基、置換基を有していても良いビニレン基、または置換基を有していても良いプロペニレン基を表す。Ｒ²⁰³、Ｒ²⁰⁴およびＲ²⁰⁵は、それぞれ独立に、置換基を有していても良いアリール基、置換基を有していても良いアルキル基、または水素原子を表す。Ｒ²¹¹、Ｒ²¹³、Ｒ²²¹、Ｒ²²²およびＲ²²³は、それぞれ独立に置換基を表す。Ｒ²⁰³、Ｒ²⁰⁴およびＲ²⁰⁵は、それぞれＲ²¹³、Ｒ²²²、Ｒ²²³と一緒になって、それぞれ独立に置換基を有していても良いアルキレン基、置換基を有していても良いビニレン基、または置換基を有していても良いプロペニレン基を形成していてもよい。Ｙは、アニオンを構成する原子または原子団を表す。］

[In the general formula (2), X ²⁰¹ is may have a substituent group methylene _{group, -O -, - SO 2 -} , or an optionally substituted group represents an silylene group. R ²⁰¹ represents an aryl group that may have a substituent, an alkyl group that may have a substituent, a cyano group, or a hydrogen atom. R ²⁰² represents an alkylene group which may have a substituent, a vinylene group which may have a substituent, or a propenylene group which may have a substituent. R ²⁰³ , R ²⁰⁴ and R ²⁰⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ²¹¹ , R ²¹³ , R ²²¹ , R ²²² and R ²²³ each independently represent a substituent. R ²⁰³ , R ^204, and R ²⁰⁵ together with R ²¹³ , R ²²² , and R ²²³ are each independently an alkylene group that may have a substituent, or vinylene that may have a substituent. A propenylene group which may have a group or a substituent may be formed. Y represents an atom or an atomic group constituting an anion. ]

［一般式（３）において、Ｒ³⁰¹は置換基を有していても良いアリール基、ハロゲン原子が置換していても良いアルキル基、シアノ基、または水素原子を表す。Ｒ³⁰²、Ｒ³⁰³、Ｒ³⁰⁴およびＲ³⁰⁵は、それぞれ独立に、置換基を有していても良いアリール基、置換基を有していても良いアルキル基、または水素原子を表す。Ｒ³¹¹、Ｒ³¹²、Ｒ³¹³、Ｒ³²¹、Ｒ³²²およびＲ³²³は、それぞれ独立に置換基を表す。Ｒ³⁰²、Ｒ³⁰³、Ｒ³⁰⁴およびＲ³⁰⁵は、それぞれＲ³¹²、Ｒ³¹³、Ｒ³²²、Ｒ³²³と一緒になって、それぞれ独立に置換基を有していても良いアルキレン基、置換基を有していても良いビニレン基、または置換基を有していても良いプロペニレン基を形成していてもよい。Ｙは、アニオンを構成する原子または原子団を表す。］

[In General Formula (3), R ³⁰¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group or a hydrogen atom. R ³⁰² , R ³⁰³ , R ³⁰⁴ and R ³⁰⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ³¹¹ , R ³¹² , R ³¹³ , R ³²¹ , R ³²² and R ³²³ each independently represent a substituent. R ³⁰² , R ³⁰³ , R ^304, and R ³⁰⁵ together with R ³¹² , R ³¹³ , R ³²² , and R ³²³ have an alkylene group and a substituent that may each independently have a substituent. A vinylene group which may be substituted, or a propenylene group which may have a substituent may be formed. Y represents an atom or an atomic group constituting an anion. ]

［一般式（４）において、Ｘ⁴⁰¹は置換基を有していても良いメチレン基、−Ｏ−、−ＳＯ₂−、または置換基を有していても良いシリレン基を表す。Ｒ⁴⁰²は置換基を有していても良いアルキレン基、置換基を有していても良いビニレン基、または置換基を有していても良いプロペニレン基を表す。Ｒ⁴⁰³、Ｒ⁴⁰⁴およびＲ⁴⁰⁵は、それぞれ独立に、置換基を有していても良いアリール基、置換基を有していても良いアルキル基、または水素原子を表す。Ｒ⁴¹¹、Ｒ⁴¹³、Ｒ⁴²¹、Ｒ⁴²²およびＲ⁴²³は、それぞれ独立に置換基を表す。Ｒ⁴⁰³、Ｒ⁴⁰⁴およびＲ⁴⁰⁵は、それぞれＲ⁴¹³、Ｒ⁴²²、Ｒ⁴²³と一緒になって、それぞれ独立に置換基を有していても良いアルキレン基、置換基を有していても良いビニレン基、または置換基を有していても良いプロペニレン基を形成していてもよい。Ｙは、アニオンを構成する原子または原子団を表す。］

[In General Formula (4), X ⁴⁰¹ represents an optionally substituted methylene group, —O—, —SO ₂ —, or an optionally substituted silylene group. R ⁴⁰² represents an alkylene group which may have a substituent, a vinylene group which may have a substituent, or a propenylene group which may have a substituent. R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ⁴¹¹ , R ⁴¹³ , R ⁴²¹ , R ⁴²² and R ⁴²³ each independently represent a substituent. R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ together with R ⁴¹³ , R ⁴²² and R ⁴²³ are each independently an alkylene group which may have a substituent, or vinylene which may have a substituent. A propenylene group which may have a group or a substituent may be formed. Y represents an atom or an atomic group constituting an anion. ]

［一般式（５）において、Ｒ⁵⁰¹は、置換基を有していても良いアリール基、ハロゲン原子が置換していても良いアルキル基、シアノ基、または水素原子を表す。Ｒ⁵⁰²、Ｒ⁵⁰³、Ｒ⁵⁰⁴およびＲ⁵⁰⁵は、それぞれ独立に、置換基を有していても良いアリール基、置換基を有していても良いアルキル基、または水素原子を表す。Ｒ⁵¹¹、Ｒ⁵¹²、Ｒ⁵¹³、Ｒ⁵²¹、Ｒ⁵²²およびＲ⁵²³は、それぞれ独立に置換基を表す。Ｒ⁵⁰²、Ｒ⁵⁰³、Ｒ⁵⁰⁴およびＲ⁵⁰⁵は、それぞれＲ⁵¹²、Ｒ⁵¹³、Ｒ⁵²²、Ｒ⁵²³と一緒になって、それぞれ独立に置換基を有していても良いアルキレン基、置換基を有していても良いビニレン基、または置換基を有していても良いプロペニレン基を形成していてもよい。Ｙは、アニオンを構成する原子または原子団を表す。］

[In General Formula (5), R ⁵⁰¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group or a hydrogen atom. R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ and R ⁵⁰⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ⁵¹¹ , R ⁵¹² , R ⁵¹³ , R ⁵²¹ , R ⁵²² and R ⁵²³ each independently represent a substituent. R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ and R ⁵⁰⁵ together with R ⁵¹² , R ⁵¹³ , R ⁵²² and R ⁵²³ have an alkylene group and a substituent which may each independently have a substituent. A vinylene group which may be substituted, or a propenylene group which may have a substituent may be formed. Y represents an atom or an atomic group constituting an anion. ]

［一般式（６）において、Ｒ⁶⁰¹は置換基を有していても良いアリール基、ハロゲン原子が置換していても良いアルキル基、シアノ基、または水素原子を表す。Ｒ⁶⁰²、Ｒ⁶⁰³、Ｒ⁶⁰⁴およびＲ⁶⁰⁵は、それぞれ独立に、置換基を有していても良いアリール基、置換基を有していても良いアルキル基、または水素原子を表す。Ｒ⁶¹¹、Ｒ⁶¹²、Ｒ⁶¹³、Ｒ⁶²¹、Ｒ⁶²²およびＲ⁶²³は、それぞれ独立に置換基を表す。Ｒ⁶⁰²、Ｒ⁶⁰³、Ｒ⁶⁰⁴およびＲ⁶⁰⁵は、それぞれＲ⁶¹²、Ｒ⁶¹³、Ｒ⁶²²、Ｒ⁶²³と一緒になって、それぞれ独立に置換基を有していても良いアルキレン基、置換基を有していても良いビニレン基、または置換基を有していても良いプロペニレン基を形成していてもよい。Ｍは、金属原子を表す。Ｌは、配位子を表す。ｎは、１〜４のいずれかの自然数を表す。Ｙは、アニオンを構成する原子または原子団を表す。］

[In General Formula (6), R ⁶⁰¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group or a hydrogen atom. R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ and R ⁶⁰⁵ each independently represent an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ⁶¹¹ , R ⁶¹² , R ⁶¹³ , R ⁶²¹ , R ⁶²² and R ⁶²³ each independently represent a substituent. R ⁶⁰² , R ⁶⁰³ , R ^604, and R ⁶⁰⁵ each have an alkylene group or a substituent that may be independently substituted with R ⁶¹² , R ⁶¹³ , R ⁶²² , or R ⁶²³ , respectively. A vinylene group which may be substituted, or a propenylene group which may have a substituent may be formed. M represents a metal atom. L represents a ligand. n represents any natural number of 1 to 4. Y represents an atom or an atomic group constituting an anion. ]

［一般式（７）において、Ａｒ⁷⁰¹およびＡｒ⁷⁰²は、それぞれ独立に、置換基を有していても良い２以上の環が縮環した芳香族環を表す。Ａｒ⁷⁰³は、置換基を有していても良い芳香族環を表す。Ｒ⁷⁰¹、Ｒ⁷⁰²、Ｒ⁷⁰³、Ｒ⁷⁰⁴、Ｒ⁷⁰⁵およびＲ⁷⁰⁶は、それぞれ独立に、置換基を有していても良いアリール基、置換基を有していても良いアルキル基、または水素原子を表す。Ｙは、アニオンを構成する原子または原子団を表す。］

[In General Formula (7), Ar ⁷⁰¹ and Ar ⁷⁰² each independently represent an aromatic ring in which two or more rings optionally having a substituent are condensed. Ar ⁷⁰³ represents an aromatic ring which may have a substituent. R ⁷⁰¹ , R ⁷⁰² , R ⁷⁰³ , R ⁷⁰⁴ , R ⁷⁰⁵ and R ⁷⁰⁶ are each independently an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom Represents. Y represents an atom or an atomic group constituting an anion. ]

<3> The curable coloring composition according to <1> or <2>, wherein the curable coloring composition contains a yellow pigment compound.
<4> The curable coloring composition as described in any one of <1> to <3> above, which comprises a monomer and a polymerization initiator.
<5> A color filter produced by forming a colored layer using the curable coloring composition according to any one of <1> to <4>.
<6> The step of applying the curable coloring composition according to any one of <1> to <4> above on a support to form a colored layer, and forming the colored layer into a pattern The manufacturing method of the color filter which has the process to expose.
<7> A liquid crystal display device comprising the color filter according to <5> or the color filter produced by the method for producing a color filter according to <6>.
<8> A solid-state imaging device comprising the color filter according to <5> or the color filter produced by the method for producing a color filter according to <6>.
<9> A compound having a structure represented by the general formula (5).
<10> A compound having a structure represented by the general formula (6).

  The curable coloring composition of the present invention is heat resistant and has preferable absorption characteristics that transmits light in the magenta region and absorbs light in the cyan region. In addition, by adding a yellow pigment compound, a curable coloring composition having a particularly high effect as a green application can be provided. According to the present invention, there are provided a curable coloring composition, a color filter, and a method for producing the same, which have high color purity, a high absorption coefficient in a thin layer, and excellent in fastness (particularly heat resistance and light resistance) and voltage holding ratio. It is possible to provide. In addition, according to the present invention, it is possible to provide a liquid crystal display device and a solid-state imaging device in which the display image is vividly colored and exhibits high contrast. Furthermore, if the present invention is used, it is possible to provide a liquid crystal display device and a solid-state imaging device in which the display image is vividly colored and exhibits high contrast.

  Hereinafter, the curable coloring composition of the present invention, the color filter using the curable coloring composition of the present invention and the manufacturing method thereof, the liquid crystal display device and the solid-state imaging device using the curable coloring composition of the present invention, and The dye compound of the present invention will be described in detail. The coloring compound of the present invention can be used as a coloring component of the curable coloring composition.

The coloring compound contained in the curable coloring composition of the present invention The coloring compound contained in the curable coloring composition of the present invention will be described.
The curable coloring composition of the present invention includes a dye compound represented by the general formula (A). The general formula (A) is represented by the following upper structural formula in the present specification, but can also be represented by the lower structural formula. The dye compound represented by the general formula (A) is an arylmethane dye compound or a ring-closing compound thereof, and is a dye compound in which a cation portion and an anion portion are paired. The general formula (A) shows a structure in which a monovalent cation moiety and a monovalent anion moiety are paired, but the valence of the cation moiety and the anion moiety is not limited to monovalent. A dye compound having a structure represented by the general formula (A) and composed of a divalent or higher cation moiety and a divalent or higher anion moiety is also included in the general formula (A). When the valence of the cation moiety in the general formula (A) is m and the valence of the anion moiety is n, the cation moiety and the anion moiety exist in a ratio of n: m.

Z represents a nitrogen atom or —C (R ¹ ) —. R ¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group, a hydrogen atom, or an aromatic ring which may have a substituent.
As the aryl group, those having 1 to 10 carbon atoms constituting the ring are preferable. For example, a benzene ring, a naphthalene ring, an anthracene ring, etc. are mentioned. Moreover, the heteroaryl ring containing a hetero atom may be sufficient. Although the hetero atom which comprises a ring is not specifically limited, It is preferable that they are a nitrogen atom, a sulfur atom, or an oxygen atom. Specific examples of the heteroaryl ring include a pyridine ring, an indole ring, an oxazole ring, a benzothiazole ring, a pyrrole ring, and a quinoline ring. Although the substituent which may have on an aryl ring is not specifically limited, For example, the below-mentioned substituent group A is mentioned. Of these, a halogen atom, an amino group, an alkyl group, a sulfonyl group, and a sulfonamide group are preferable.
The alkyl group which may be substituted by a halogen atom may be linear, branched or cyclic, and preferably has 1 to 30 carbon atoms, Are more preferable, and those of 1 to 6 are particularly preferable. The halogen atom to be substituted is preferably a fluorine atom.
The aryl group constituting the aromatic ring which may have a substituent preferably has 1 to 10 carbon atoms constituting the ring. For example, a benzene ring, a naphthalene ring, an anthracene ring, etc. are mentioned. The aromatic ring is preferably one substituted with —N (R ³¹ ) (R ³² ). Here, R ³¹ and R ³² may each independently have a substituent. It preferably represents an aryl group, an alkyl group which may have a substituent, or a hydrogen atom.

Q ¹ represents a nitrogen atom or —C (R ¹⁴ ) —. Q ² represents a nitrogen atom or —C (R ²⁴ ) —. R ¹⁴ and R ²⁴ each independently represents a substituent. Although the kind of substituent is not specifically limited, For example, the below-mentioned substituent group A is mentioned. Of these, a halogen atom, an amino group, an alkyl group, a sulfonyl group, and a sulfonamide group are preferable.

R ² , R ³ , R ⁴ and R ⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. Aryl group has the same meaning as the aryl group in R ^1, the preferred range is also the same. The alkyl group may be linear, branched or cyclic, preferably has 1 to 20 carbon atoms, more preferably has 1 to 10 carbon atoms, Those having 1 to 8 carbon atoms are particularly preferred.

R ¹¹ , R ¹² , R ¹³ , R ¹⁴ , R ²¹ , R ²² , R ²³ and R ²⁴ each independently represent a substituent. Although the kind of substituent is not specifically limited, For example, the below-mentioned substituent group A is mentioned. Of these, a halogen atom, an amino group, an alkyl group, a sulfonyl group, and a sulfonamide group are preferable.

R ² , R ³ , R ⁴ and R ⁵ together with R ¹² , R ¹³ , R ²² and R ²³ each have an alkylene group or a substituent which may have a substituent independently. A vinylene group which may be substituted, or a propenylene group which may have a substituent may be formed.
The alkylene group preferably has 2 or 3 carbon atoms. Although it does not specifically limit as a substituent which an alkylene group, vinylene group, and propenylene group may have, For example, the below-mentioned substituent group A is mentioned. Of these, a halogen atom and an alkyl group are preferable.

Y represents an atom or an atomic group constituting an anion.
The anion is not particularly limited. For example, acetate ion, methanesulfonate ion, toluenesulfonate ion, trifluoromethanesulfonate ion, tetraphenylborate ion, tetrakispentafluorophenylborate ion, bistrifluoromethanesulfonylimide ion , Tristrifluoromethanesulfonylmethide ion, fluorine ion, chlorine ion, bromine ion, iodine ion, hexafluoroantimonate ion, perchlorate ion, periodate ion, nitrate ion, tetrafluoroborate ion, hexafluorophosphate Ion, hydrogen sulfate ion, etc. Among these, from the viewpoint of improving solubility in organic solvents, tetraphenylborate ion, tetrakispentafluorophenylborate ion, bistrifluoromethanesulfonylimide ion, hexafluoroantimonate ion, tetrafluoroborate ion, hexafluoro Phosphate ions are preferred, and hexafluorophosphate ions are particularly preferred.
Multivalent anions may be used. Although there is no particular limitation, anions in which sulfate ions and sulfonic acid groups are substituted with a plurality of organic substances may be used.
The anion may be a pigment derivative. For example, a dye into which a sulfonic acid is introduced, such as Direct Blue 86, can be used. Moreover, it is possible to synthesize a pigment derivative anion into which a sulfonic acid has been introduced by sulfonating a known pigment / dye with sulfuric acid or fuming sulfuric acid.

  The anion part and cation part of the general formula (A) may be connected to each other via a linking group. In this case, sulfonic acid is preferable as the anion moiety, and the sulfonic acid is preferably substituted on the aromatic ring of the cation moiety or on the alkyl group.

  The general formula (A) satisfies any one of the above conditions (1) to (7). Details of the conditions (1) to (7) will be described in the following general formulas (1) to (7).

<Substituent group A>
An alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as a methyl group, ethyl group, iso-propyl group, tert-butyl group, n- Octyl group, n-decyl group, n-hexadecyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, etc.), alkenyl group (preferably 2-30 carbon atoms, more preferably 2-20 carbon atoms, especially Preferably it is C2-C10, for example, a vinyl group, an allyl group, 2-butenyl group, 3-pentenyl group etc.), an alkynyl group (preferably C2-C30, more preferably C2-C2). To 20, particularly preferably 2 to 10 carbon atoms, such as a propargyl group and a 3-pentynyl group), an aryl group (preferably The number of carbon atoms is 6 to 30, more preferably 6 to 20, and particularly preferably 6 to 12, and examples thereof include a phenyl group, a p-methylphenyl group, a naphthyl group, and an anthranyl group.), An amino group (Preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, and particularly preferably 0 to 10 carbon atoms. For example, amino group, methylamino group, dimethylamino group, diethylamino group, dibenzylamino group, diphenyl Amino group, ditolylamino group, etc.), alkoxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms, such as methoxy group, ethoxy group, Butoxy group, 2-ethylhexyloxy group, etc.), aryloxy group (preferably having 6 to 30 carbon atoms, more preferred) Or having 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, etc.), heterocyclic oxy group (preferably carbon The number is 1 to 30, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms. Examples thereof include a pyridyloxy group, a pyrazyloxy group, a pyrimidyloxy group, and a quinolyloxy group), an acyl group (preferably. C1-C30, More preferably, it is C1-C20, Most preferably, it is C1-C12, for example, an acetyl group, a benzoyl group, a formyl group, a pivaloyl group etc. are mentioned), an alkoxycarbonyl group (preferably). Has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, and particularly preferably 2 to 12 carbon atoms. Examples include a rubonyl group and an ethoxycarbonyl group. ), An aryloxycarbonyl group (preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, such as a phenyloxycarbonyl group), an acyloxy group ( Preferably it has 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, and examples thereof include an acetoxy group, a benzoyloxy group, etc.), an acylamino group (preferably 2 carbon atoms). To 30, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms such as acetylamino group and benzoylamino group), alkoxycarbonylamino group (preferably 2 to 30 carbon atoms). More preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonyl An aryloxycarbonylamino group (preferably having 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, such as a phenyloxycarbonylamino group) ), A sulfonylamino group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as a methanesulfonylamino group, a benzenesulfonylamino group, etc. ), Sulfamoyl groups (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 12 carbon atoms, such as sulfamoyl group, methylsulfamoyl group, dimethylsulfamoyl group) Group, phenylsulfamoyl group, etc.), carbamoyl group (preferably carbon 1 to 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include a carbamoyl group, a methylcarbamoyl group, a diethylcarbamoyl group, a phenylcarbamoyl group, and the like, and an alkylthio group (preferably). Has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include a methylthio group and an ethylthio group, and an arylthio group (preferably 6 to 30 carbon atoms). , More preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as a phenylthio group), a heterocyclic thio group (preferably 1 to 30 carbon atoms, more preferably 1 carbon atom). To 20, particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimidazolylthio group, 2-benz Examples thereof include an oxazolylthio group and a 2-benzthiazolylthio group. ), A sulfonyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as a mesyl group and a tosyl group), a sulfinyl group (preferably). Has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as methanesulfinyl group and benzenesulfinyl group, and ureido group (preferably 1 carbon atom). To 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as a ureido group, a methylureido group, a phenylureido group, etc.), a phosphoric acid amide group (preferably a carbon number). 1 to 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide group, phenyl phosphorus Amide group, etc.), hydroxy group, mercapto group, halogen atom (eg fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group , Hydrazino group, imino group, heterocyclic group (preferably having 1 to 30 carbon atoms, more preferably 1 to 12 carbon atoms, and examples of the hetero atom include a nitrogen atom, an oxygen atom, and a sulfur atom, Is an imidazolyl group, a pyridyl group, a quinolyl group, a furyl group, a thienyl group, a piperidyl group, a morpholino group, a benzoxazolyl group, a benzimidazolyl group, a benzthiazolyl group, a carbazolyl group, an azepinyl group, or the like. Preferably 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 carbon atoms. 24, for example, a trimethylsilyl group, a triphenylsilyl group, etc.), a silyloxy group (preferably having 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, For example, a trimethylsilyloxy group, a triphenylsilyloxy group, etc.), a sulfonamide group (preferably having a carbon number of 1 to 30, more preferably 1 to 20, particularly preferably 1 to 16. For example, N, N- And dibutylsulfonamide group, N-2-ethylhexylsulfonamide group, Ns-butylsulfonamide group, etc.)

  It is preferable that the pigment | dye compound contained in the curable coloring composition of this invention has a structure represented by either of General formula (1)-(7).

The general formula (1) will be described.

R ¹⁰¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group or a hydrogen atom.
As the aryl group, those having 1 to 10 carbon atoms constituting the ring are preferable. For example, a benzene ring, a naphthalene ring, an anthracene ring, etc. are mentioned. Moreover, the heteroaryl ring containing a hetero atom may be sufficient. Although the hetero atom which comprises a ring is not specifically limited, It is preferable that they are a nitrogen atom, a sulfur atom, or an oxygen atom. Specific examples of the heteroaryl ring include a pyridine ring, an indole ring, an oxazole ring, a benzothiazole ring, a pyrrole ring, and a quinoline ring. The substituent that may be present on the aryl ring is not particularly limited, and examples thereof include the above-described substituent group A. Of these, a halogen atom, an amino group, an alkyl group, a sulfonyl group, and a sulfonamide group are preferable.
The alkyl group that may be substituted by a halogen atom may be linear, branched, or cyclic, and preferably has 1 to 30 carbon atoms, and preferably has 1 to 20 carbon atoms. Some are more preferable, and those having 1 to 6 are particularly preferable. The halogen atom to be substituted is preferably a fluorine atom.

^R102 represents an alkylene group which may have a substituent, a vinylene group which may have a substituent, or a propenylene group which may have a substituent.
The alkylene group preferably has 2 or 3 carbon atoms. Although it does not specifically limit as a substituent which an alkylene group, vinylene group, and propenylene group may have, For example, the above-mentioned substituent group A is mentioned. Of these, a halogen atom and an alkyl group are preferable.

R ¹¹¹ , R ¹¹³ , R ¹¹⁴ , R ¹²¹ , R ¹²² , R ¹²³ and R ¹²⁴ each independently represent a substituent. Although the kind of substituent is not specifically limited, For example, the above-mentioned substituent group A is mentioned. Of these, a halogen atom, an amino group, an alkyl group, a sulfonyl group, and a sulfonamide group are preferable.

R ¹⁰³ , R ¹⁰⁴ and R ¹⁰⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. Aryl group has the same meaning as the aryl group in R ^101, and the preferred range is also the same. The alkyl group may be linear, branched or cyclic, preferably has 1 to 20 carbon atoms, more preferably has 1 to 10 carbon atoms, Those having 1 to 8 carbon atoms are particularly preferred.
R ¹⁰³ , R ¹⁰⁴ and R ¹⁰⁵ together with R ¹¹³ , R ¹²² and R ¹²³ are each independently an alkylene group which may have a substituent, or vinylene which may have a substituent. A propenylene group which may have a group or a substituent may be formed. These are the same meaning as R ^102, and the preferred range is also the same.

  Y in general formula (1) has the same meaning as Y in general formula (A), and the preferred range is also the same.

The general formula (2) will be described.

X ²⁰¹ represents an optionally substituted methylene group, —O—, —SO ₂ —, or an optionally substituted silylene group. The substituent that the methylene group and the silylene group may have is preferably selected from the above-mentioned compound group A, and an alkyl group is particularly preferable.

R ²⁰¹ has the same meaning as R ¹⁰¹ , and the preferred range is also the same. R ²⁰² has the same meaning as R ¹⁰² and the preferred range is also the same. R ²⁰³ , R ²⁰⁴ and R ²⁰⁵ have the same ^meanings as R ¹⁰³ , R ¹⁰⁴ and R ¹⁰⁵ , and preferred ranges are also the same. R ²¹¹ , R ²¹³ , R ²²¹ , R ²²² and R ²²³ have the same ^meanings as R ¹¹¹ , R ¹¹³ , R ¹²¹ , R ¹²² and R ¹²³ , and preferred ranges are also the same. Y has the same meaning as Y in formula (A), and the preferred range is also the same.

The general formula (3) will be described.

R ³⁰¹ has the same meaning as R ¹⁰¹ , and the preferred range is also the same. R ³⁰² , R ³⁰³ , R ³⁰⁴ and R ³⁰⁵ have the same ^meanings as R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ and R ¹⁰⁵ , and preferred ranges are also the same. R ³¹¹ , R ³¹² , R ³¹³ , R ³²¹ , R ³²² and R ³²³ are synonymous with R ¹¹¹ , R ¹¹³ , R ¹²¹ , R ¹²² and R ¹²³ , and preferred ranges are also the same. Y has the same meaning as Y in formula (A), and the preferred range is also the same.

The general formula (4) will be described.

X ⁴⁰¹ has the same meaning as X ²⁰¹ , and the preferred range is also the same. R ⁴⁰² has the same meaning as R ¹⁰² and the preferred range is also the same. R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ are synonymous with R ¹⁰³ , R ¹⁰⁴ and R ¹⁰⁵ , and preferred ranges are also the same. R ⁴¹¹ , R ⁴¹³ , R ⁴²¹ , R ⁴²² and R ⁴²³ are synonymous with R ¹¹¹ , R ¹¹³ , R ¹²¹ , R ¹²² and R ¹²³ , and preferred ranges are also the same. Y has the same meaning as Y in formula (A), and the preferred range is also the same.

The general formula (5) will be described.

R ⁵⁰¹ has the same meaning as R ¹⁰¹ and the preferred range is also the same. R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ and R ⁵⁰⁵ are synonymous with R ¹⁰³ , R ¹⁰⁴ and R ¹⁰⁵ , and preferred ranges are also the same. R ⁵¹¹ , R ⁵¹² , R ⁵¹³ , R ⁵²¹ , R ⁵²² and R ⁵²³ have the same ^meanings as R ¹¹¹ , R ¹¹³ , R ¹²¹ , R ¹²² and R ¹²³ , and preferred ranges are also the same. Y has the same meaning as Y in formula (A), and the preferred range is also the same.

The general formula (6) will be described.

R ⁶⁰¹ has the same meaning as R ¹⁰¹ and the preferred range is also the same. R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ and R ⁶⁰⁵ are synonymous with R ¹⁰³ , R ¹⁰⁴ and R ¹⁰⁵ , and preferred ranges are also the same. R ⁶¹¹ , R ⁶¹² , R ⁶¹³ , R ⁶²¹ , R ⁶²² and R ⁶²³ are synonymous with R ¹¹¹ , R ¹¹³ , R ¹²¹ , R ¹²² and R ¹²³ , and preferred ranges are also the same. M represents a metal atom. Preferably, it is selected from metal atoms in the fourth period. Y has the same meaning as Y in formula (A), and the preferred range is also the same.

L represents a ligand (the bond formed by coordination includes, for example, coordination bond, covalent bond, and ionic bond). L is not particularly limited as long as L is an atomic group coordinated to M, but a halogen atom, an atomic group coordinated with a carbon atom, an atomic group coordinated with a nitrogen atom, an atomic group coordinated with an oxygen atom, a sulfur atom Preferred is an atomic group coordinated with, an atomic group coordinated with a phosphorus atom, an atomic group coordinated with a carbon atom, an atomic group coordinated with a nitrogen atom, or an atomic group coordinated with an oxygen atom, more preferably a nitrogen atom An atom group coordinated by and an atom group coordinated by an oxygen atom are more preferred.
L may be a monodentate ligand or a polydentate ligand. As a multidentate ligand, a group of atoms coordinated by carbon atoms, a group of atoms coordinated by nitrogen atoms, a group of atoms coordinated by oxygen atoms, a group of atoms coordinated by sulfur atoms, and coordinated by phosphorus atoms It preferably contains an atomic group, an atomic group coordinated with a carbon atom, an atomic group coordinated with a nitrogen atom, more preferably an atomic group coordinated with an oxygen atom, an atomic group coordinated with a carbon atom, More preferably, it contains an atomic group coordinated by a nitrogen atom.

  Examples of an atomic group coordinated by a carbon atom include an imino group, an aromatic hydrocarbon ring group (benzene, naphthalene, etc.), a heterocyclic group (thiophene, pyridine, pyrazine, pyrimidine, pyridazine, triazine, thiazole, oxazole, pyrrole, Imidazole, pyrazole, triazole, etc.) and condensed rings containing them, and tautomers thereof. These groups may further have a substituent (preferably having no substituent). Examples of the substituent include the substituent group B described later, and the preferred range is also the same.

  As an atomic group coordinated with a nitrogen atom, for example, a nitrogen-containing heterocyclic group (pyridine group, pyrazine group, pyrimidine group, pyridazine group, triazine group, thiazole group, oxazole group, pyrrole group, imidazole group, pyrazole group, triazole group, etc. Etc.), amino group (alkylamino group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, for example, methylamino group), arylamino group (for example, phenyl Amino group)), acylamino groups (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as acetylamino group, benzoylamino group, etc. An alkoxycarbonylamino group (preferably having 2 to 30 carbon atoms, more preferably 2-20 carbon atoms, particularly preferably 2-12 carbon atoms, such as a methoxycarbonylamino group, and aryloxycarbonylamino groups (preferably 7-30 carbon atoms, more preferably 7-7 carbon atoms). 20, particularly preferably 7 to 12 carbon atoms, such as a phenyloxycarbonylamino group), a sulfonylamino group (preferably 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably C1-C12, for example, a methanesulfonylamino group, a benzenesulfonylamino group, etc.), an imino group, etc. are mentioned. These groups may be further substituted. Examples of the substituent include the substituent group B described later, and the preferred range is also the same.

  As an atomic group coordinated by an oxygen atom, an alkoxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 10 carbon atoms, such as a methoxy group, an ethoxy group, or a butoxy group. Group, 2-ethylhexyloxy group, etc.), an aryloxy group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, for example, phenyloxy Group, 1-naphthyloxy group, 2-naphthyloxy group, etc.), heterocyclic oxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms). For example, pyridyloxy group, pyrazyloxy group, pyrimidyloxy group, quinolyloxy group, etc.), acyloxy group (preferably carbon 2 to 30, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms, such as an acetoxy group and a benzoyloxy group), a silyloxy group (preferably 3 to 40 carbon atoms, and more). Preferably it has 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyloxy group and triphenylsilyloxy group.), Carbonyl group (for example, ketone group, ester group, amide group, etc.) And ether groups (for example, dialkyl ether groups, diaryl ether groups, furyl groups, etc.). These groups may be further substituted (preferably having no substituent). Examples of the substituent include the substituent group B described later, and the preferred range is also the same.

  As an atomic group coordinated by a sulfur atom, an alkylthio group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as a methylthio group and an ethylthio group). An arylthio group (preferably having 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as a phenylthio group), and a heterocyclic thio group. (Preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms. For example, pyridylthio group, 2-benzimidazolylthio group, 2-benzoxazolylthio group, 2 -Benzthiazolylthio group, etc.), thiocarbonyl group (eg thioketone group, thioester group etc.), thioether group (eg di Ruki thioether group, diaryl thioether, etc. thiofuryl group). These groups may be further substituted (preferably having no substituent). Examples of the substituent include the substituent group B described later, and the preferred range is also the same.

  Examples of the atomic group coordinated by the phosphorus atom include a dialkylphosphino group, a diarylphosphino group, a trialkylphosphino group, a triarylphosphino group, and a phosphinin group. These groups may be further substituted (preferably having no substituent). Examples of the substituent include the substituent group B described later, and the preferred range is also the same.

  L may further bind to another metal atom to form a binuclear metal complex.

  n represents any natural number of 1 to 4. n is preferably 1 or 2.

<Substituent group B>
For example, an alkyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 10 carbon atoms such as methyl, ethyl, iso-propyl, tert-butyl, n-octyl, n-decyl, n-hexadecyl, cyclopropyl, cyclopentyl, cyclohexyl, etc.), alkenyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms). Yes, for example, vinyl, allyl, 2-butenyl, 3-pentenyl, etc.), alkynyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms). For example, propargyl, 3-pentynyl, etc.), an aryl group (preferably having 6 to 30 carbon atoms, more preferably Alternatively, it has 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, and examples thereof include phenyl, p-methylphenyl, naphthyl, anthranyl, and the like, and an amino group (preferably having 0 to 30 carbon atoms. Preferably it has 0 to 20 carbon atoms, particularly preferably 0 to 10 carbon atoms, and examples thereof include amino, methylamino, dimethylamino, diethylamino, dibenzylamino, diphenylamino, ditolylamino and the like, and an alkoxy group (preferably C1-C30, More preferably, it is C1-C20, Most preferably, it is C1-C10, for example, a methoxy, an ethoxy, butoxy, 2-ethylhexyloxy etc. are mentioned), an aryloxy group (preferably). Has 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, and particularly preferably 6 to 12 carbon atoms. For example, phenyloxy, 1-naphthyloxy, 2-naphthyloxy, etc.), a heterocyclic oxy group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms). For example, pyridyloxy, pyrazyloxy, pyrimidyloxy, quinolyloxy, etc.), an acyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, For example, acetyl, benzoyl, formyl, pivaloyl, etc.), an alkoxycarbonyl group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonyl , Ethoxycarbonyl, etc.), aryloxycarbonyl group ( Preferably it is C7-30, More preferably, it is C7-20, Most preferably, it is C7-12, for example, phenyloxycarbonyl etc. are mentioned. ), An acyloxy group (preferably having 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms such as acetoxy and benzoyloxy), an acylamino group (preferably 2-30 carbon atoms, more preferably 2-20 carbon atoms, particularly preferably 2-10 carbon atoms, and examples thereof include acetylamino, benzoylamino, and the like, and an alkoxycarbonylamino group (preferably having 2-2 carbon atoms). 30, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 12 carbon atoms, such as methoxycarbonylamino, etc.), aryloxycarbonylamino group (preferably 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms, particularly preferably 7 to 12 carbon atoms, such as phenyloxycarbonyl And sulfonylamino groups (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as methanesulfonylamino and benzenesulfonylamino). ), A sulfamoyl group (preferably having 0 to 30 carbon atoms, more preferably 0 to 20 carbon atoms, particularly preferably 0 to 12 carbon atoms, such as sulfamoyl, methylsulfamoyl, dimethylsulfamoyl, phenyl Sulfamoyl, etc.), a carbamoyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as carbamoyl, methylcarbamoyl, diethylcarbamoyl, Phenylcarbamoyl etc.), alkylthio group ( Preferably, it has 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include methylthio, ethylthio and the like, and an arylthio group (preferably 6 to 30 carbon atoms). , More preferably 6 to 20 carbon atoms, particularly preferably 6 to 12 carbon atoms, such as phenylthio, etc.), a heterocyclic thio group (preferably 1 to 30 carbon atoms, more preferably 1 to carbon atoms). 20, particularly preferably 1 to 12 carbon atoms, such as pyridylthio, 2-benzimidazolylthio, 2-benzoxazolylthio, 2-benzthiazolylthio and the like, and a sulfonyl group (preferably having a carbon number). 1 to 30, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as mesyl and tosyl). Rufinyl group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, and examples thereof include methanesulfinyl and benzenesulfinyl. ), A ureido group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, and particularly preferably 1 to 12 carbon atoms, such as ureido, methylureido, phenylureido, etc.), phosphoric acid. An amide group (preferably having 1 to 30 carbon atoms, more preferably 1 to 20 carbon atoms, particularly preferably 1 to 12 carbon atoms, such as diethyl phosphoric acid amide and phenylphosphoric acid amide), a hydroxy group , Mercapto group, halogen atom (eg fluorine atom, chlorine atom, bromine atom, iodine atom), cyano group, sulfo group, carboxyl group, nitro group, hydroxamic acid group, sulfino group, hydrazino group, imino group, heterocyclic group ( Preferably it is C1-C30, More preferably, it is C1-C12, As a hetero atom, for example, a nitrogen atom, oxygen Children, sulfur atoms, specifically imidazolyl, pyridyl, quinolyl, furyl, thienyl, piperidyl, morpholino, benzoxazolyl, benzimidazolyl, benzthiazolyl, carbazolyl group, azepinyl group, etc.), silyl group (preferably). Has 3 to 40 carbon atoms, more preferably 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyl, triphenylsilyl, and the like, and a silyloxy group (preferably 3 to 40 carbon atoms). More preferably, it has 3 to 30 carbon atoms, particularly preferably 3 to 24 carbon atoms, and examples thereof include trimethylsilyloxy, triphenylsilyloxy, etc.) A group in which two substituents are bonded to form a ring structure Etc. The plurality of substituents may be the same or different. As a preferable range of the substituent, an alkyl group, an aryl group, an amino group, an alkoxy group, a halogen atom, a heterocyclic group, and a silyl group are preferable, a halogen atom, an alkyl group, and a silyl group are more preferable, and a halogen atom is particularly preferable.

The general formula (7) will be described.

Ar ⁷⁰¹ and Ar ⁷⁰² each independently represent an aromatic ring in which two or more rings optionally having a substituent are condensed. The aromatic ring may be a heteroaromatic ring containing a heteroatom. Although the hetero atom which may be contained is not specifically limited, A nitrogen atom, a sulfur atom, and an oxygen atom are preferable. Specific examples include naphthalene ring, anthracene ring, quinoline ring, indole ring, carbazole ring, benzothiazole ring, benzoxazole ring, benzothiophene ring and the like.

Ar ⁷⁰³ represents an aromatic ring which may have a substituent. It is preferable that carbon number which comprises a ring is 1-10. For example, a benzene ring, a naphthalene ring, an anthracene ring, etc. are mentioned. Moreover, the heteroaryl ring containing a hetero atom may be sufficient. Although it does not specifically limit as a hetero atom which comprises a ring, It is preferable that they are a nitrogen atom, a sulfur atom, and an oxygen atom. Specific examples include a pyridine ring, an indole ring, an oxazole ring, a benzothiazole ring, a pyrrole ring, and a quinoline ring. The substituent that may be present on the aryl ring is not particularly limited, and examples thereof include the above-described substituent group A.

R ⁷⁰¹ , R ⁷⁰² , R ⁷⁰³ , R ⁷⁰⁴ , R ⁷⁰⁵ and R ⁷⁰⁶ each independently represents an aryl group which may be substituted, an alkyl group which may have substitution, or a hydrogen atom. Although it does not specifically limit as a substituent which you may have, For example, the above-mentioned substituent group A is mentioned. Of these, halogen and alkyl groups are preferred.
Y has the same meaning as Y in formula (A), and the preferred range is also the same.

  Specific examples of the compound represented by formula (A) are shown below.

Specific example of general formula (1)

Specific example of general formula (2)

Specific example of general formula (3) [Cl ⁻ can be exemplified as the anion moiety]

Specific examples of compounds of general formula (4)

Specific examples of compounds of general formula (5)

Specific examples of compounds of formula (6)

Specific examples of compounds of general formula (7)

  The dye compound represented by the general formula (A) used in the present invention may be obtained and used commercially if it is commercially available. In addition, a known compound or a derivative thereof may be obtained and used by appropriately selecting or combining known obtaining methods or synthetic methods. For general synthetic methods, see “Dye Chemistry and Applications” (Ken Matsuoka, Dai Nippon Book, pages 20-23), Chem. Res. Toxicol. (2003, 16 volumes, pages 285-294), US published patent 2006-0179585, Spectrochimina Acta Part A (2001, 57 volumes, pages 2271-2283), the above-mentioned patent documents 1-8, and documents cited by them. Etc. can be synthesized with reference to the above. Also, a dye compound having a desired anion portion can be obtained by synthesizing a counter anion having a chlorine anion and dissolving it and adding a salt having a corresponding anion portion or a conjugate acid as an aqueous solution and salting out. I can do it.

Of the compounds represented by the general formula (A), the method for synthesizing the compound represented by the general formula (5) is not particularly limited. For example, the compound can be synthesized by using the following method conditions.

Although the synthesis method of the compound represented by General formula (6) among the compounds represented by General formula (A) is not specifically limited, For example, it is compoundable by using the following method conditions.

In the curable coloring composition of this invention, the pigment | dye compound represented by general formula (A) may be contained individually by 1 type, and may be used together 2 or more types.
The content of the coloring compound represented by the general formula (A) in the curable coloring composition of the present invention varies depending on the molecular weight and the extinction coefficient, but with respect to the total solid content of the curable coloring composition, 1-70 mass% is preferable and 10-50 mass% is more preferable. When the dye content is 10% by mass or more, a good color density (for example, a color density suitable for liquid crystal display) can be obtained, and when it is 50% by mass or less, pixel patterning becomes good. Is advantageous.

  Furthermore, the curable coloring composition of the present invention may contain a dye compound or a pigment compound having another structure and a dispersion thereof. The dye compound may have any structure as long as it does not affect the hue of the colored image. For example, an anthraquinone type (for example, an anthraquinone compound described in JP-A No. 2001-108815), a phthalocyanine type (E.g., phthalocyanine compounds described in U.S. Patent Application Publication No. 2008/0076044), xanthene series (e.g., CI Acid Red 289), triarylmethane series (e.g., I Acid Blue 7, CI Acid Blue 83, CI Acid Blue 90, CISolvent Blue 38 , CI Acid Violet17, CI Acid Violet 17 Examples include CI 49 (CIAcid Violet49), CI Acid Green3, squarylium, pyrazole azo, methine, pyrazolone azo, and barbiturazo. Examples of soluble dyes include CI Solvent Yellow 4, CI Solvent Yellow 88, CI Solvent Yellow 14, CI Solvent Yellow 15, CI Solvent Yellow 24, CI Solvent Yellow 94, CI Solvent Yellow 98, CI Solvent Yellow 162, CI Solvent Yellow 82, and the like.

  Examples of pigment compounds include perylene, perinone, quinacridone, quinacridonequinone, anthraquinone, anthanthrone, benzimidazolone, disazo condensation, disazo, azo, indanthrone, phthalocyanine, triarylcarbonium, dioxazine, aminoanthraquinone, diketopyrrolopyrrole, Indigo, thioindigo, isoindoline, isoindolinone, pyranthrone, isoviolanthrone and the like. More specifically, for example, perylene compound pigments such as Pigment Red 190, Pigment Red 224, and Pigment Violet 29, perinone compound pigments such as Pigment Orange 43, and Pigment Red 194, Pigment Violet 19, and Pigment Violet. 42, quinacridone such as Pigment Red 122, Pigment Red 192, Pigment Red 202, Pigment Red 207, or Pigment Red 209, quinacridone compound pigment, Pigment Red 206, Pigment Orange 48, or Pigment Orange 49 Quinone compound pigments, anthraquinone compound pigments such as pigment yellow 147, anthanthrone compound pigments such as pigment red 168, and pigments Benzimidazolone compound pigments such as Pigment 25, Pigment Violet 32, Pigment Orange 36, Pigment Yellow 120, Pigment Yellow 180, Pigment Yellow 181, Pigment Orange 62, or Pigment Red 185 Yellow 93, Pigment Yellow 94, Pigment Yellow 95, Pigment Yellow 128, Pigment Yellow 166, Pigment Orange 34, Pigment Orange 13, Pigment Orange 31, Pigment Red 144, Pigment Red 166, Pigment Red Red 220, Pigment Red 221, Pigment Red 242, Pigment Red 248, Pigment Red 262, or Pigment Red Disazo condensation compound pigments such as Rune 23, Pigment Yellow 13, Pigment Yellow 83, or Pigment Yellow 188 Disazo Compound Pigments, Pigment Red 187, Pigment Red 170, Pigment Yellow 74, Pigment Yellow 150, Pigment Red 48, Pigment Red 53, Pigment Orange 64, Pigment Red 247 and other azo compound pigments, Pigment Blue 60 and other indanthrone compound pigments, Pigment Green 7, Pigment Green 36, Pigment Green 37, phthalocyanine compound pigments such as Pigment Green 58, Pigment Blue 16, Pigment Blue 75, or Pigment Blue 15, Pigment Blue 56, Alternatively, a triarylcarbonium compound pigment such as Pigment Blue 61, a dioxazine compound pigment such as Pigment Violet 23, or Pigment Violet 37, an anthraquinone compound pigment such as Pigment Red 177, Pigment Red 254, and Pigment Red 255 Pigment Red 264, Pigment Red 272, Pigment Orange 71, or Pigment Orange 73, etc., Diketopyrrolopyrrole Compound Pigment, Pigment Red 88 or other thioindigo compound pigment, Pigment Yellow 139, Pigment Orange 66, etc. Isoindoline compound pigments such as Pigment Yellow 109, Pigment Orange 61, and Pigment Orange 61 0 or pyranthrone compound pigments such as Pigment Red 216 or isoviolanthrone compound pigments, such as Pigment Violet 31, and the like.

Content of the said dye and pigment can be used in the range which does not impair the effect of this invention, It is 0.5 mass%-70 mass% with respect to the total solid of the curable coloring composition of this invention. preferable.
When the curable coloring composition of the present invention is prepared by blending the dye or pigment as a dispersion, it can be prepared according to the descriptions in JP-A-9-197118 and JP-A-2000-239544.

In the present invention, a curable green coloring composition can be preferably provided, particularly by adding a yellow pigment compound. The provided curable green coloring composition has high color purity, and when applied to a liquid crystal display device and a solid-state image sensor, the coloring of the display image can be vivid and exhibit high contrast.
The addition amount of the yellow dye compound is preferably 1% by mass to 70% by mass and more preferably 10% by mass to 50% by mass with respect to the total solid content of the curable coloring composition of the present invention. . Moreover, when the pigment | dye compound represented by general formula (A) of this invention is 100 mass parts, it is preferable that the addition amount of a yellow pigment compound is 10 mass parts-1000 mass parts, and 20 mass parts- More preferably, it is 500 parts by mass.

[Polymerizable compound]
The colored composition of the present invention preferably contains at least one polymerizable compound. Examples of the polymerizable compound include addition polymerizable compounds having at least one ethylenically unsaturated double bond.

  Specifically, it is selected from compounds having at least one terminal ethylenically unsaturated bond, preferably two or more. Such a compound group is widely known in the industrial field, and these can be used without particular limitation in the present invention. These may be any of chemical forms such as monomers, prepolymers, that is, dimers, trimers and oligomers, or a mixture thereof and a (co) polymer thereof.

  Examples of monomers and their (co) polymers include unsaturated carboxylic acids (eg, acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.), esters thereof, amides, and these (Co) polymers, preferably esters of unsaturated carboxylic acids and aliphatic polyhydric alcohol compounds, amides of unsaturated carboxylic acids and aliphatic polyhydric amine compounds, and their (co) It is a polymer. Also, addition reaction products of monofunctional or polyfunctional isocyanates or epoxies with unsaturated carboxylic acid esters or amides having a nucleophilic substituent such as hydroxyl group, amino group, mercapto group, monofunctional or polyfunctional. A dehydration condensation reaction product with a functional carboxylic acid is also preferably used. Further, an addition reaction product of an unsaturated carboxylic acid ester or amide having an electrophilic substituent such as an isocyanate group or an epoxy group with a monofunctional or polyfunctional alcohol, amine or thiol, and further a halogen group A substitution reaction product of an unsaturated carboxylic acid ester or amide having a detachable substituent such as a tosyloxy group and a monofunctional or polyfunctional alcohol, amine or thiol is also suitable. As another example, it is also possible to use a group of compounds substituted with unsaturated phosphonic acid, styrene, vinyl ether or the like instead of the unsaturated carboxylic acid.

Specific examples of the ester monomer of an aliphatic polyhydric alcohol compound and an unsaturated carboxylic acid include acrylic acid esters such as ethylene glycol diacrylate, triethylene glycol diacrylate, 1,3-butanediol diacrylate, tetra Methylene glycol diacrylate, propylene glycol diacrylate, neopentyl glycol diacrylate, trimethylolpropane triacrylate, trimethylolpropane tri (acryloyloxypropyl) ether, trimethylolethane triacrylate, hexanediol diacrylate, 1,4-cyclohexanediol Diacrylate, tetraethylene glycol diacrylate, pentaerythritol diacrylate, pentaerythritol tria Relate, pentaerythritol tetraacrylate, dipentaerythritol diacrylate, dipentaerythritol hexaacrylate, sorbitol triacrylate, sorbitol tetraacrylate, sorbitol pentaacrylate, sorbitol hexaacrylate, tri (acryloyloxyethyl) isocyanurate, polyester acrylate oligomer, isocyanur Examples include acid EO-modified triacrylate.
Examples of methacrylic acid esters include tetramethylene glycol dimethacrylate, triethylene glycol dimethacrylate, neopentyl glycol dimethacrylate, trimethylolpropane trimethacrylate, trimethylolethane trimethacrylate, ethylene glycol dimethacrylate, and 1,3-butanediol. Dimethacrylate, hexanediol dimethacrylate, pentaerythritol dimethacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate, dipentaerythritol dimethacrylate, dipentaerythritol hexamethacrylate, sorbitol trimethacrylate, sorbitol tetramethacrylate, bis [p- (3- Methacryloxy-2-hi Rokishipuropokishi) phenyl] dimethyl methane, bis - [p- (methacryloxyethoxy) phenyl] dimethyl methane, and the like.

Further, as the itaconic acid ester, for example, ethylene glycol diitaconate, propylene glycol diitaconate, 1,3-butanediol diitaconate, 1,4-butanediol diitaconate, tetramethylene glycol diitaconate, pentaerythritol Diitaconate, sorbitol tetritaconate, etc., and crotonic acid esters such as ethylene glycol dicrotonate, tetramethylene glycol dicrotonate, pentaerythritol dicrotonate, sorbitol tetradicrotonate, etc. For example, ethylene glycol diisocrotonate, pentaerythritol diisocrotonate, sorbitol tetraisocrotonate, etc. To, for example, ethylene glycol dimaleate, triethylene glycol dimaleate, pentaerythritol dimaleate, sorbitol tetra malate, and the like.
Examples of other esters include aliphatic alcohol esters described in JP-B-51-47334 and JP-A-57-196231, JP-A-59-5240, and JP-A-59-5241. And those having an aromatic skeleton described in JP-A-2-226149 and those containing an amino group described in JP-A-1-165613. Furthermore, the ester monomers described above can also be used as a mixture.

Specific examples of amide monomers of aliphatic polyvalent amine compounds and unsaturated carboxylic acids include methylene bis-acrylamide, methylene bis-methacrylamide, 1,6-hexamethylene bis-acrylamide, 1,6-hexamethylene bis. -Methacrylamide, diethylenetriamine trisacrylamide, xylylene bisacrylamide, xylylene bismethacrylamide and the like.
Examples of other preferable amide monomers include those having a cyclohexylene structure described in JP-B No. 54-21726.

Further, urethane-based addition polymerizable compounds produced by using an addition reaction of isocyanate and hydroxyl group are also suitable. Specific examples thereof include, for example, one molecule described in JP-B-48-41708. Vinyl urethane containing two or more polymerizable vinyl groups in one molecule obtained by adding a vinyl monomer containing a hydroxyl group represented by the following general formula (B) to a polyisocyanate compound having two or more isocyanate groups Compounds and the like.
CH ₂ = C (R) COOCH ₂ CH (R ′) OH (B)
[In General Formula (B), R and R ′ each independently represent H or CH ₃ . ]

  About these polymeric compounds, the details of usage methods, such as the structure, single use, combined use, and addition amount, can be arbitrarily set according to the final performance design of a curable coloring composition. For example, from the viewpoint of sensitivity, a structure having a high unsaturated group content per molecule is preferable, and in many cases, a bifunctional or higher functionality is preferable. Also, from the viewpoint of increasing the strength of the colored cured film, those having three or more functionalities are preferable, and those having different functional numbers and different polymerizable groups (for example, acrylic acid esters, methacrylic acid esters, styrene compounds, vinyl ether compounds). It is also effective to adjust both sensitivity and intensity by using together. In addition, the selection of the polymerizable compound is also possible with respect to the compatibility and dispersibility with other components (for example, photopolymerization initiator, colorant (pigment), binder polymer, etc.) contained in the curable coloring composition. The method of use is an important factor. For example, compatibility may be improved by using a low-purity compound or using two or more kinds in combination. In addition, a specific structure may be selected from the viewpoint of improving adhesion to a hard surface such as a support.

  The content of the polymerizable compound in the total solid content of the coloring composition (total content in the case of 2 or more types) is not particularly limited, and is 10% by mass from the viewpoint of more effectively obtaining the effects of the present invention. -80% by mass is preferable, 15% by mass to 75% by mass is more preferable, and 20% by mass to 60% by mass is particularly preferable.

[Photopolymerization initiator]
The colored composition of the present invention preferably contains at least one photopolymerization initiator. The photopolymerization initiator is not particularly limited as long as it can polymerize the polymerizable compound, and is preferably selected from the viewpoints of characteristics, initiation efficiency, absorption wavelength, availability, cost, and the like.

  Examples of the photopolymerization initiator include at least one active halogen compound selected from a halomethyloxadiazole compound and a halomethyl-s-triazine compound, a 3-aryl-substituted coumarin compound, a lophine dimer, a benzophenone compound, and an acetophenone compound. And derivatives thereof, cyclopentadiene-benzene-iron complex and salts thereof, oxime compounds, and the like. Specific examples of the photopolymerization initiator include those described in paragraphs [0070] to [0077] of JP-A No. 2004-295116. Among these, an oxime compound is preferable from the viewpoint of rapid polymerization reaction.

The oxime-based compound (hereinafter also referred to as “oxime-based photopolymerization initiator”) is not particularly limited. For example, JP-A-2000-80068, WO02 / 100903A1, JP-A-2001-233842, etc. The described oxime compounds are mentioned.
Specific examples include 2- (O-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-butanedione, 2- (O-benzoyloxime) -1- [4- (phenylthio). Phenyl] -1,2-pentanedione, 2- (O-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-hexanedione, 2- (O-benzoyloxime) -1- [4 -(Phenylthio) phenyl] -1,2-heptanedione, 2- (O-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione, 2- (O-benzoyloxime)- 1- [4- (methylphenylthio) phenyl] -1,2-butanedione, 2- (O-benzoyloxime) -1- [4- (ethylphenylthio) phenyl] -1, -Butanedione, 2- (O-benzoyloxime) -1- [4- (butylphenylthio) phenyl] -1,2-butanedione, 1- (O-acetyloxime) -1- [9-ethyl-6- ( 2-Methylbenzoyl) -9H-carbazol-3-yl] ethanone, 1- (O-acetyloxime) -1- [9-methyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethanone 1- (O-acetyloxime) -1- [9-propyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethanone, 1- (O-acetyloxime) -1- [9- Ethyl-6- (2-ethylbenzoyl) -9H-carbazol-3-yl] ethanone, 1- (O-acetyloxime) -1- [9-ethyl-6- (2-butylbenzoyl) Such as 9H- carbazol-3-yl] ethanone and the like. However, it is not limited to these.

  Moreover, in this invention, the compound represented by following General formula (11) is more preferable as an oxime type compound from a viewpoint of a sensitivity, the stability at the time of diameter, and the coloring at the time of post-heating.

  In the general formula (11), R and X each independently represent a monovalent substituent, A represents a divalent organic group, and Ar represents an aryl group. n is an integer in any one of 1-5.

  R is preferably an acyl group from the viewpoint of increasing sensitivity, and specifically, an acetyl group, a propionyl group, a benzoyl group, and a toluyl group are preferable.

  A is an alkylene group substituted with an unsubstituted alkylene group or an alkyl group (for example, a methyl group, an ethyl group, a tert-butyl group, or a dodecyl group) from the viewpoint of increasing sensitivity and suppressing coloration due to heating. An alkylene group substituted with an alkenyl group (for example, vinyl group, allyl group), an aryl group (for example, phenyl group, p-tolyl group, xylyl group, cumenyl group, naphthyl group, anthryl group, phenanthryl group, styryl group) A substituted alkylene group is preferred.

  Ar is preferably a substituted or unsubstituted phenyl group from the viewpoint of increasing sensitivity and suppressing coloring due to heating. In the case of a substituted phenyl group, the substituent is preferably a halogen group such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.

X is an alkyl group that may have a substituent, an aryl group that may have a substituent, or an alkenyl that may have a substituent from the viewpoint of improving solvent solubility and absorption efficiency in the long wavelength region. Group, an alkynyl group which may have a substituent, an alkoxy group which may have a substituent, an aryloxy group which may have a substituent, an alkylthioxy group which may have a substituent, a substituent An arylthioxy group which may have an amino group and an amino group which may have a substituent are preferable.
Further, n in the general formula (11) is preferably 1 or 2.

  In addition to the above photopolymerization initiator, other known photopolymerization initiators described in paragraph [0079] of JP-A No. 2004-295116 are used for the curable coloring composition of the present invention. Also good.

A photoinitiator can be contained individually by 1 type or in combination of 2 or more types.
The content (total content in the case of two or more) of the curable coloring composition of the photopolymerization initiator in the total solid content is 3% by mass to 20% by mass from the viewpoint of more effectively obtaining the effects of the present invention. % Is preferable, 4% by mass to 19% by mass is more preferable, and 5% by mass to 18% by mass is particularly preferable.

[Organic solvent]
The curable coloring composition of the present invention can contain at least one organic solvent.
The organic solvent is basically not particularly limited as long as it can satisfy the solubility of each coexisting component and the coating property when it is used as a curable coloring composition, in particular, the solubility of the binder, the coating property, It is preferable to select in consideration of safety.

  Examples of organic solvents include esters such as ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl lactate, and ethyl lactate. Oxyacetic acid alkyl esters (eg, methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate (specific examples include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate). )), 3-oxypropionic acid alkyl esters (eg, methyl 3-oxypropionate, ethyl 3-oxypropionate and the like (specifically, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, 3- Methyl ethoxypropionate, 3-ethoxy Ethyl propionate, etc.)), 2-oxypropionic acid alkyl esters (eg, methyl 2-oxypropionate, ethyl 2-oxypropionate, propyl 2-oxypropionate, etc. (specifically, 2 -Methyl methoxypropionate, ethyl 2-methoxypropionate, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, etc.)), 2-oxy-2-methylpropionic acid Methyl, ethyl 2-oxy-2-methylpropionate (specifically, methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate, etc.), methyl pyruvate, Ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate , Methyl 2-oxobutanoate, ethyl 2-oxobutanoate, and the like.

Examples of ethers include diethylene glycol dimethyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether. Propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate and the like.
Examples of ketones include methyl ethyl ketone, cyclohexanone, 2-heptanone, and 3-heptanone.
Preferable examples of aromatic hydrocarbons include toluene and xylene.

  It is also preferable to mix two or more of these organic solvents from the viewpoints of the solubility of each of the above-mentioned components, and the solubility and the improvement of the coating surface state when an alkali-soluble binder is included. In this case, particularly preferably, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl cellosolve acetate, ethyl lactate, diethylene glycol dimethyl ether, butyl acetate, methyl 3-methoxypropionate, 2-heptanone, cyclohexanone, ethyl carbitol It is a mixed solution composed of two or more selected from acetate, butyl carbitol acetate, propylene glycol methyl ether, and propylene glycol methyl ether acetate.

  The content of the organic solvent in the curable coloring composition is preferably such that the total solid concentration in the composition is 10% by mass to 80% by mass, and more preferably 15% by mass to 60% by mass. .

[Other ingredients]
The curable coloring composition of the present invention may further contain other components such as an alkali-soluble binder and a crosslinking agent in addition to the above-described components as long as the effects of the present invention are not impaired.

-Alkali-soluble binder-
The alkali-soluble binder is not particularly limited except that it has alkali solubility, and can be preferably selected from the viewpoints of heat resistance, developability, availability, and the like.

  The alkali-soluble binder is preferably a linear organic high molecular polymer that is soluble in an organic solvent and can be developed with a weak alkaline aqueous solution. Examples of such linear organic high molecular polymers include polymers having a carboxylic acid in the side chain, such as JP-A-59-44615, JP-B-54-34327, JP-B-58-12577, and JP-B-54-. No. 25957, JP-A-59-53836, JP-A-59-71048, methacrylic acid copolymer, acrylic acid copolymer, itaconic acid copolymer, crotonic acid copolymer, etc. Examples thereof include polymers, maleic acid copolymers, partially esterified maleic acid copolymers, and acidic cellulose derivatives having a carboxylic acid in the side chain are also useful.

  In addition to the above, the alkali-soluble binder in the present invention includes a polymer having a hydroxyl group added with an acid anhydride, a polyhydroxystyrene resin, a polysiloxane resin, poly (2-hydroxyethyl (meth)), and the like. Acrylate), polyvinylpyrrolidone, polyethylene oxide, polyvinyl alcohol, and the like are also useful. Further, the linear organic high molecular polymer may be a copolymer of hydrophilic monomers. Examples include alkoxyalkyl (meth) acrylate, hydroxyalkyl (meth) acrylate, glycerol (meth) acrylate, (meth) acrylamide, N-methylol acrylamide, secondary or tertiary alkyl acrylamide, dialkylaminoalkyl (meth). Acrylate, morpholine (meth) acrylate, N-vinylpyrrolidone, N-vinylcaprolactam, vinylimidazole, vinyltriazole, methyl (meth) acrylate, ethyl (meth) acrylate, branched or linear propyl (meth) acrylate, branched or straight Examples include butyl (meth) acrylate of a chain, phenoxyhydroxypropyl (meth) acrylate, and the like. Other hydrophilic monomers include tetrahydrofurfuryl group, phosphoric acid group, phosphoric ester group, quaternary ammonium base, ethyleneoxy chain, propyleneoxy chain, sulfonic acid group and groups derived from salts thereof, morpholinoethyl group, etc. Monomers comprising it are also useful.

  The alkali-soluble binder may have a polymerizable group in the side chain in order to improve the crosslinking efficiency, and includes, for example, an allyl group, a (meth) acryl group, an allyloxyalkyl group, etc. in the side chain. Polymers and the like are also useful. Examples of the polymer containing the above-described polymerizable group include commercially available KS resist-106 (manufactured by Osaka Organic Chemical Industry Co., Ltd.), cyclomer P series (manufactured by Daicel Chemical Industries, Ltd.), and the like. In addition, in order to increase the strength of the cured film, alcohol-soluble nylon, polyether of 2,2-bis- (4-hydroxyphenyl) -propane and epichlorohydrin, and the like are also useful.

  Among these various alkali-soluble binders, from the viewpoint of heat resistance, polyhydroxystyrene resins, polysiloxane resins, acrylic resins, acrylamide resins, and acrylic / acrylamide copolymer resins are preferable, and from the viewpoint of development control. Are preferably acrylic resins, acrylamide resins, and acrylic / acrylamide copolymer resins.

  Examples of the acrylic resin include a copolymer made of a monomer selected from benzyl (meth) acrylate, (meth) acrylic acid, hydroxyethyl (meth) acrylate, (meth) acrylamide, and the like, and a commercially available KS resist 106 ( Osaka Organic Chemical Industry Co., Ltd.) and Cyclomer P Series (Daicel Chemical Industries, Ltd.) are preferred.

The alkali-soluble binder is preferably a polymer having a weight average molecular weight (polystyrene equivalent value measured by GPC method) of 1000 to 2 × 10 ⁵ from the viewpoint of developability, liquid viscosity, etc., and a weight of 2000 to 1 × 10 ⁵ A coalescence is more preferable, and a polymer of 5000 to 5 × 10 ⁴ is particularly preferable.

-Crosslinking agent-
A supplementary crosslinking agent may be used in the curable coloring composition of the present invention to further increase the hardness of the colored cured film obtained by curing the curable coloring composition.
The crosslinking agent is not particularly limited as long as the film can be cured by a crosslinking reaction. For example, at least selected from (a) an epoxy resin, (b) a methylol group, an alkoxymethyl group, and an acyloxymethyl group. Substituted with at least one substituent selected from a melamine compound, a guanamine compound, a glycoluril compound or a urea compound, (c) a methylol group, an alkoxymethyl group, and an acyloxymethyl group, substituted with one substituent, Phenol compounds, naphthol compounds or hydroxyanthracene compounds are mentioned. Of these, polyfunctional epoxy resins are preferred.
For details such as specific examples of the crosslinking agent, the description in paragraphs [0134] to [0147] of JP-A No. 2004-295116 can be referred to.

（構成単位（Ａ）および（Ｂ）中、Ｒ¹及びＲ³はそれぞれ独立に、水素原子又はメチル基を表し、Ｒ²は炭素数１〜４の直鎖アルキレン基を表し、Ｒ⁴は水素原子又は炭素数１〜４のアルキル基を表し、Ｌは炭素数３〜６のアルキレン基を表し、下記式：

（Ｒ⁵は、炭素数１〜４のアルキル基を表し、相溶性と被塗布面に対する濡れ性の点で、炭素数１〜３のアルキル基が好ましく、炭素数２または３のアルキル基がより好ましい）で表される分岐アルキレン基であることが好ましく、ｐ及びｑは重合比を表す重量百分率であり、ｐは１０重量％〜８０重量％の数値を表し、ｑは２０重量％〜９０重量％の数値を表し、ｒは１〜１８の整数を表し、ｎは１〜１０の整数を表す。）
構成単位Ａ及び構成単位Ｂを繰り返し単位として含む共重合体である界面活性剤の重量平均分子量（Ｍｗ）は、１，５００〜５，０００がより好ましい。
これらの界面活性剤は、１種単独で又は２種以上を混合して使用することができる。
本発明の硬化性着色組成物における界面活性剤の添加量は、他の成分の合計質量１００部に対して、１０重量部以下であることが好ましく、０．０１〜１０重量部であることがより好ましく、０．０１〜１重量部であることがさらに好ましい。 -Surfactant-
The curable coloring composition of the present invention may contain a surfactant. As the surfactant, any of anionic, cationic, nonionic, or amphoteric surfactants can be used, but a preferred surfactant is a nonionic surfactant.
Examples of nonionic surfactants include polyoxyethylene higher alkyl ethers, polyoxyethylene higher alkyl phenyl ethers, higher fatty acid diesters of polyoxyethylene glycol, silicone-based and fluorine-based surfactants. . In addition, the following trade names are KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Polyflow (manufactured by Kyoeisha Chemical Co., Ltd.), F-Top (manufactured by JEMCO), MegaFac (manufactured by DIC Corporation), Florard (Sumitomo 3M) (Manufactured by Co., Ltd.), Asahi Guard, Surflon (manufactured by Asahi Glass Co., Ltd.) and PolyFox (manufactured by OMNOVA).
In addition, the surfactant contains the following structural unit A and structural unit B as repeating units, and has a polystyrene-reduced weight average molecular weight (Mw) measured by gel permeation chromatography of 1,000 to 10,000. A polymer can be mentioned as a preferred example.

(In the structural units (A) and (B), R ¹ and R ³ each independently represent a hydrogen atom or a methyl group, R ² represents a linear alkylene group having 1 to 4 carbon atoms, and R ⁴ represents hydrogen. An atom or a C1-C4 alkyl group is represented, L represents a C3-C6 alkylene group, and following formula:

(R ⁵ represents an alkyl group having 1 to 4 carbon atoms, and is preferably an alkyl group having 1 to 3 carbon atoms, more preferably an alkyl group having 2 or 3 carbon atoms in terms of compatibility and wettability with respect to the coated surface. A branched alkylene group represented by (preferably) is preferable, p and q are weight percentages representing a polymerization ratio, p represents a value of 10 wt% to 80 wt%, and q is 20 wt% to 90 wt%. % Represents an integer of 1 to 18, and n represents an integer of 1 to 10. )
As for the weight average molecular weight (Mw) of surfactant which is a copolymer containing the structural unit A and the structural unit B as a repeating unit, 1500-5,000 are more preferable.
These surfactants can be used individually by 1 type or in mixture of 2 or more types.
The addition amount of the surfactant in the curable coloring composition of the present invention is preferably 10 parts by weight or less and preferably 0.01 to 10 parts by weight with respect to 100 parts by weight as the total mass of other components. More preferred is 0.01 to 1 part by weight.

-Other additives-
If necessary, the curable coloring composition of the present invention contains various additives such as fillers, polymer compounds other than those mentioned above, adhesion promoters, antioxidants, ultraviolet absorbers, anti-aggregation agents and the like. can do. Examples of these additives include those described in paragraphs [0155] to [0156] of JP-A No. 2004-295116.
The curable coloring composition of the present invention contains a sensitizer and a light stabilizer described in paragraph [0078] of JP-A No. 2004-295116, and a thermal polymerization inhibitor described in paragraph [0081] of the same publication. can do.

Further, when the alkali solubility in the non-exposed area is promoted and the developability of the curable coloring composition is further improved, the composition is an organic carboxylic acid, preferably a low molecular weight organic carboxylic acid having a molecular weight of 1000 or less. Is preferably added.
Specifically, for example, aliphatic monocarboxylic acids such as formic acid, acetic acid, propionic acid, butyric acid, valeric acid, pivalic acid, caproic acid, diethyl acetic acid, enanthic acid, caprylic acid; oxalic acid, malonic acid, succinic acid, Aliphatic dicarboxylic acids such as glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, brassic acid, methylmalonic acid, ethylmalonic acid, dimethylmalonic acid, methylsuccinic acid, tetramethylsuccinic acid, citraconic acid; Aliphatic tricarboxylic acids such as tricarballylic acid, aconitic acid, camphoric acid; aromatic monocarboxylic acids such as benzoic acid, toluic acid, cumic acid, hemelitic acid, mesitylene acid; phthalic acid, isophthalic acid, terephthalic acid, trimellitic acid, Aromatic polycarboxylic acids such as trimesic acid, melophanoic acid, pyromellitic acid; phenylacetic acid Hydratropic acid, hydrocinnamic acid, mandelic acid, phenyl succinic acid, atropic acid, cinnamic acid, methyl cinnamate, benzyl cinnamate, cinnamylidene acetic acid, coumaric acid, other carboxylic acids such as umbellic acid.

Manufacturing method of curable coloring composition The curable coloring composition of this invention is prepared by mixing each above-mentioned component and arbitrary components as needed.
In preparing the curable coloring composition, the components constituting the curable coloring composition may be combined at once, or may be combined sequentially after each component is dissolved and dispersed in a solvent. In addition, there are no particular restrictions on the charging order and working conditions when blending. For example, the composition may be prepared by dissolving and dispersing all components in a solvent at the same time. If necessary, each component may be suitably used as two or more solutions / dispersions at the time of use (at the time of application). ) May be mixed to prepare a composition.
The curable coloring composition prepared as described above is preferably filtered using a filter having a pore size of 0.01 μm to 3.0 μm, more preferably a pore size of about 0.05 μm to 0.5 μm. Can be used for use.
Since the curable coloring composition of the present invention can form a colored cured film excellent in hue and contrast, a color filter used for a liquid crystal display device (LCD) or a solid-state imaging device (for example, CCD, CMOS, etc.) It can be preferably used for forming colored pixels such as printing inks, inkjet inks, and paints. In particular, it is suitable for use in forming colored pixels for liquid crystal display devices.

Color filter and manufacturing method thereof The color filter of the present invention is configured by providing a colored region on a substrate. The colored region on the substrate is composed of colored films such as red (R), green (G), and blue (B) that form each pixel of the color filter. Since the color filter of the present invention is formed by including a diarylmethane compound having a predetermined structure, the color when displaying an image is bright and the contrast is high, which is particularly suitable for a liquid crystal display device.

  The color filter of the present invention may be formed by any method as long as it is a method capable of forming a colored region (colored pattern) cured by containing an arylmethane compound. Preferably, it is produced using the curable coloring composition of the present invention.

The method for producing a color filter of the present invention includes a step (A) of applying the curable coloring composition described above on a support to form a colored layer (also referred to as a colored composition layer), and a step (A). A step of exposing the colored composition layer formed in (1) to a pattern (preferably through a mask) and developing the uncured portion of the coating film with a developer to form a colored region (colored pattern) (B ). By passing through these steps, a colored pattern composed of pixels of each color (3 colors or 4 colors) is formed, and a color filter can be obtained. In the method for producing a color filter of the present invention, in particular, the step (C) of irradiating the colored pattern formed in the step (B) with ultraviolet rays and the colored pattern irradiated with the ultraviolet rays in the step (C) are applied. On the other hand, the aspect which further provided the process (D) which heat-processes is preferable.
By such a method, a color filter used for a liquid crystal display element or a solid-state imaging element can be manufactured with low process difficulty, high quality, and low cost.
Hereinafter, the manufacturing method of the color filter of the present invention will be described more specifically.

-Process (A)-
In the method for producing a color filter of the present invention, first, the above-described curable coloring composition of the present invention is applied directly or via another layer on a support by a desired coating method, and then the curable coloring composition is prepared. A coating film (colored composition layer) made of a product is formed, and then pre-cured (pre-baked) as necessary, and the curable colored composition layer is dried.

As the support, for example, non-alkali glass, soda glass, Pyrex (registered trademark) glass, quartz glass, and the like obtained by attaching a transparent conductive film to these, used for solid-state imaging devices, etc. Examples of the photoelectric conversion element substrate include a silicone substrate and a plastic substrate. Further, on these supports, a black matrix for isolating each pixel may be formed, or a transparent resin layer may be provided for promoting adhesion. Further, if necessary, an undercoat layer may be provided on the support for improving adhesion to the upper layer, preventing diffusion of substances, or flattening the surface.
The plastic substrate preferably has a gas barrier layer and / or a solvent resistant layer on its surface.

In addition, a driving substrate on which a thin film transistor (TFT) of a thin film transistor (TFT) type color liquid crystal display device is disposed (hereinafter referred to as “TFT type liquid crystal driving substrate”) is used as a support. A color filter using the curable coloring composition of the present invention can also be formed on the substrate to produce a color filter.
Examples of the substrate in the TFT type liquid crystal driving substrate include glass, silicone, polycarbonate, polyester, aromatic polyamide, polyamideimide, and polyimide. These substrates may be subjected to appropriate pretreatment such as chemical treatment with a silane coupling agent or the like, plasma treatment, ion plating, sputtering, gas phase reaction method, vacuum deposition, etc., if desired. For example, a substrate in which a passivation film such as a silicon nitride film is formed on the surface of the TFT liquid crystal driving substrate can be used.

  The curable coloring composition of the present invention is applied to a substrate directly or via another layer by a coating method such as spin coating, slit coating, cast coating, roll coating, bar coating, ink jet, and the like. A coating film of an object can be formed.

In the coating step, the method for applying the curable coloring composition of the present invention to the substrate is not particularly limited, but a method using a slit nozzle such as a slit-and-spin method or a spinless coating method (hereinafter, Slit nozzle coating method) is preferable.
In the slit nozzle coating method, the slit-and-spin coating method and the spinless coating method have different conditions depending on the size of the coated substrate. For example, a fifth generation glass substrate (1100 mm × 1250 mm) is coated by the spinless coating method. In this case, the discharge amount of the curable coloring composition from the slit nozzle is usually 500 microliter / second to 2000 microliter / second, preferably 800 microliter / second to 1500 microliter / second. The speed is usually 50 mm / second to 300 mm / second, preferably 100 mm / second to 200 mm / second.
Moreover, as solid content of the curable coloring composition used at an application | coating process, it is 10%-20% normally, Preferably it is 13%-18%.

When forming the coating film by the curable coloring composition of this invention on a board | substrate, as thickness (after a prebaking process) of this coating film, it is generally 0.3 micrometer-5.0 micrometers, Preferably 0.5 micrometer-4 0.0 μm, most desirably 0.5 μm to 3.0 μm.
In the case of a color filter for a solid-state image sensor, the thickness of the coating film (after pre-baking) is preferably in the range of 0.5 μm to 5.0 μm.

In the coating process, usually, a pre-bake treatment is performed after coating. If necessary, vacuum treatment can be performed before pre-baking. The vacuum drying conditions are such that the degree of vacuum is usually about 0.1 to 1.0 torr, preferably about 0.2 to 0.5 torr.
The pre-bake treatment is performed in a temperature range of 50 ° C. to 140 ° C., preferably about 70 ° C. to 110 ° C. using a hot plate, an oven, etc., and can be performed under conditions of 10 seconds to 300 seconds. Note that high-frequency treatment or the like may be used in combination with the pre-bake treatment. The high frequency treatment can be used alone.

Examples of the pre-baking condition include a condition of heating at 70 ° C. to 130 ° C. for about 0.5 minutes to 15 minutes using a hot plate or an oven.
Moreover, the thickness of the coloring composition layer formed with a curable coloring composition is suitably selected according to the objective. In the color filter for liquid crystal display devices, the range of 0.2 μm to 5.0 μm is preferable, the range of 1.0 μm to 4.0 μm is more preferable, and the range of 1.5 μm to 3.5 μm is the most preferable. Moreover, in the color filter for solid-state image sensors, the range of 0.2 micrometer-5.0 micrometers is preferable, The range of 0.3 micrometer-2.5 micrometers is more preferable, The range of 0.3 micrometer-1.5 micrometers is the most preferable.
In addition, the thickness of a coloring composition layer is a film thickness after prebaking.

-Process (B)-
Subsequently, in the method for producing a color filter of the present invention, the coating film (colored composition layer) made of the colored composition formed on the support as described above is exposed through, for example, a photomask. It is. As light or radiation applicable to exposure, g-line, h-line, i-line, j-line, KrF light and ArF light are preferable, and i-line is particularly preferable. When using the i-line to the irradiation light is preferably irradiated at an exposure dose of ^{100mJ / cm 2 ~10000mJ / cm 2} .

  Other exposure rays include ultra high pressure, high pressure, medium pressure and low pressure mercury lamps, chemical lamps, carbon arc lamps, xenon lamps, metal halide lamps, various visible and ultraviolet laser light sources, fluorescent lamps, tungsten lamps, solar Light or the like can also be used.

~ Exposure process using laser light source ~
In an exposure method using a laser light source, an ultraviolet laser is used as the light source.
The irradiation light is preferably an ultraviolet laser having a wavelength in the range of 300 nm to 380 nm, more preferably an ultraviolet laser having a wavelength in the range of 300 nm to 360 nm matches the photosensitive wavelength of the resist. Is preferable. Specifically, the Nd: YAG laser third harmonic (355 nm), which is a relatively inexpensive solid output, and the excimer laser XeCl (308 nm), XeF (353 nm) can be suitably used. .
The exposure amount of the exposure object (pattern), in the range of ^{1mJ / cm 2 ~100mJ / cm 2} , the range of 1mJ / cm ² ~50mJ / cm ² is more preferable. An exposure amount within this range is preferable from the viewpoint of pattern formation productivity.

There are no particular restrictions on the exposure apparatus, but commercially available devices such as Callisto (buoy technology), EGIS (buoy technology), DF2200G (Dainippon Screen) can be used. It is. Further, devices other than those described above are also preferably used.
When manufacturing a color filter for a liquid crystal display device, exposure using mainly h-line and i-line is preferably used by a proximity exposure machine and a mirror projection exposure machine. Further, when manufacturing a color filter for a solid-state image sensor, it is preferable to mainly use i-line in a stepper exposure machine. When manufacturing a color filter using a TFT type liquid crystal driving substrate, the photomask used has a through hole or a U-shaped depression in addition to a pattern for forming a pixel (colored pattern). The thing in which the pattern for forming is provided is used.

The colored composition layer exposed as described above can be heated.
The exposure can be performed while flowing a nitrogen gas in the chamber in order to suppress oxidation fading of the coloring material in the colored composition layer.

Subsequently, development is performed with a developer on the colored composition layer after exposure. Thereby, a negative type or positive type coloring pattern (resist pattern) can be formed. In the development step, the uncured portion of the coating film after exposure is eluted in the developer, and only the cured portion remains on the substrate.
Any developer can be used as long as it dissolves the coating film (colored composition layer) of the colored composition in the uncured part, but does not dissolve the cured part. For example, combinations of various organic solvents and alkaline aqueous solutions can be used.
Examples of the organic solvent used for development include the above-described solvents that can be used in preparing the curable coloring composition of the present invention.
Examples of the alkaline aqueous solution include sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, sodium oxalate, sodium metasuccinate, aqueous ammonia, ethylamine, diethylamine, dimethylethanolamine, tetramethylammonium hydroxide, tetraethyl. Concentrations of alkaline compounds such as ammonium hydroxide, choline, pyrrole, piperidine, 1,8-diazabicyclo- [5,4,0] -7-undecene are 0.001% by mass to 10% by mass, preferably 0.01 The alkaline aqueous solution melt | dissolved so that it may become 1 mass%-1 mass% is mentioned. When the developer is an alkaline aqueous solution, the alkali concentration is preferably adjusted to be pH 11 to 13, more preferably pH 11.5 to 12.5.
An appropriate amount of a water-soluble organic solvent such as methanol or ethanol, a surfactant, or the like can be added to the alkaline aqueous solution.

The development temperature is usually 20 ° C. to 30 ° C., and the development time is 20 seconds to 90 seconds.
Development may be any of a dip method, a shower method, a spray method, and the like, and may be combined with a swing method, a spin method, an ultrasonic method, or the like. It is also possible to prevent development unevenness by previously moistening the surface to be developed with water or the like before touching the developer. It is also possible to develop with the substrate tilted.
Further, when manufacturing a color filter for a solid-state image sensor, paddle development is also used.

After the development process, a rinsing process for washing and removing excess developer is performed, followed by drying, followed by heat treatment (post-baking) to complete the curing.
The rinsing process is usually performed with pure water, but in order to save liquid, pure water is used in the final cleaning, and used pure water is used in the initial stage of cleaning, or the substrate is inclined and cleaned. Alternatively, a method of using ultrasonic irradiation together may be used.

  After the rinse treatment, after draining and drying, a heat treatment of about 200 ° C. to 250 ° C. is usually performed. In this heat treatment (post-bake), the coating film after development is continuously or batch-treated using a heating means such as a hot plate, a convection oven (hot air circulation dryer) or a high-frequency heater so as to satisfy the above conditions. It can be done with an expression.

By sequentially repeating the above steps for each color according to the desired number of hues, it is possible to produce a color filter in which a cured film (colored pattern) colored in a plurality of colors is formed.
Since the color filter of the present invention has high contrast, small color density unevenness, and good color characteristics, it can be suitably used for a solid-state imaging device or a liquid crystal display device.

-Step (C)-
In the method for producing a color filter of the present invention, in particular, post-exposure by ultraviolet irradiation can be performed on a colored pattern (pixel) formed using the curable coloring composition of the present invention.

-Process (D)-
It is preferable to further heat-treat the colored pattern that has been post-exposed by ultraviolet irradiation as described above. By heating the formed color pattern (so-called post-bake process), the color pattern can be further cured. This heat treatment can be performed by, for example, a hot plate, various heaters, an oven, or the like.
As temperature in the case of heat processing, it is preferable that it is 100 to 300 degreeC, More preferably, it is 150 to 250 degreeC. The heating time is preferably about 10 minutes to 120 minutes.

The colored pattern thus obtained constitutes a pixel in the color filter. In the production of a color filter having a plurality of hue pixels, the above steps (A), (B), and if necessary, the steps (C) and (D) may be repeated according to the desired number of colors. Good.
The process (C) and / or the process (D) may be performed each time the formation, exposure, and development of the monochromatic coloring composition layer are completed (for each color), or the desired number of colors After all the colored composition layers have been formed, exposed and developed, the step (C) and / or the step (D) may be performed collectively.

The color filter obtained by the method for producing a color filter of the present invention (the color filter of the present invention) is excellent in hue and contrast because it uses the curable coloring composition of the present invention.
The color filter of the present invention can be used for a liquid crystal display element or a solid-state image sensor, and is particularly suitable for use in a liquid crystal display device. When used in a liquid crystal display device, it is possible to display an image excellent in spectral characteristics and contrast while achieving a good hue using a dye as a colorant.

As described above, the curable coloring composition of the present invention has been mainly described for the purpose of forming a color filter coloring pattern in the above description. Can also be applied.
The black matrix on the substrate is a curable coloring composition containing a black pigment processed pigment such as carbon black or titanium black, and is subjected to coating, exposure, and development steps, and then, if necessary, post It can be formed by baking.

Liquid crystal display device and solid-state image sensor The liquid crystal display element and solid-state image sensor of the present invention comprise the color filter of the present invention. More specifically, for example, by forming an alignment film on the inner surface side of the color filter, facing the electrode substrate, and filling the gap with liquid crystal and sealing, a panel which is the liquid crystal display element of the present invention is obtained. . For example, the solid-state image sensor of this invention is obtained by forming a color filter on a light receiving element.

  For the definition of liquid crystal display devices and details of each display device, refer to, for example, “Electronic Display Devices (Akio Sasaki, published by Kogyo Kenkyukai 1990)”, “Display Devices (written by Junaki Ibuki, Sangyo Tosho) Issued in 1989). The liquid crystal display device is described in, for example, “Next-generation liquid crystal display technology (edited by Tatsuo Uchida, published by Kogyo Kenkyukai 1994)”. The liquid crystal display device to which the present invention can be applied is not particularly limited, and can be applied to, for example, various types of liquid crystal display devices described in the “next generation liquid crystal display technology”.

The color filter of the present invention is particularly effective for a color TFT liquid crystal display device. The color TFT liquid crystal display device is described in, for example, “Color TFT liquid crystal display (issued in 1996 by Kyoritsu Publishing Co., Ltd.)”. Furthermore, the present invention is applied to a liquid crystal display device with a wide viewing angle such as a lateral electric field driving method such as IPS, a pixel division method such as MVA, STN, TN, VA, OCS, FFS, and R-OCB. it can.
The color filter of the present invention can also be used for a bright and high-definition COA (Color-filter On Array) system.

  When the color filter of the present invention is used for a liquid crystal display element, a high contrast can be realized when combined with a conventionally known three-wavelength tube of a cold cathode tube, and further, red, green and blue LED light sources (RGB-LED). By using as a backlight, a liquid crystal display device having high luminance and high color purity and good color reproducibility can be provided.

When described in color order, the blue light emitting diode includes a gallium nitride (GaN) -based material, specifically, a sapphire substrate / n-GaN / n-Al0.15Ga0.85N / MQW or SQW layer. Some have a layer structure of /p-Al0.15Ga0.85N/p-GaN/electrode. Here, the MQW or SQW layer is a multi quantum well structure (MQW) or a single quantum well structure (SQW). As a material constituting these quantum well structures, InxGaN1-xN can be exemplified, and blue color is generated when x = 0.2, and green color is generated when x = 0.4. With this material, when the In (indium) composition is increased, green light emission can be obtained. However, as the In composition increases, the crystallinity deteriorates, so that the light emission efficiency decreases.

  As another material for ensuring sufficient light emission luminance, a GaInN green LED or a combination of GaInN blue LED + green phosphor can be used. By doing so, the peak wavelength can be brought to an appropriate wavelength in the range of 520 to 570 nm.

  Examples of the green phosphor that can be used include oxides, nitrides, and oxynitrides activated with cerium and / or europium.

As the red LED, satisfactory light emission characteristics can be obtained by using an AlInGaP-based LED. As another red LED, there is a GaAlAs red LED. Its structure is GaAs substrate / n-GaAs / n-InGaAlP / undoped InG.
It has a layer structure of aAlP / p-InGaAlP / p-GaAs / electrode. Among the three elements of In, Ga, and Al, the emission wavelength can be changed by changing the ratio of Ga and Al by combining the lattice constant of GaAs with an In atomic ratio of 0.5. Increasing the proportion of Al shifts the emission to a short wavelength. When the atomic ratio of Ga is 0.25 and the atomic ratio of Al is about 0.25, red light emission with a wavelength of about 600 nm can be obtained.

  The LEDs listed above can be made by chemical vapor deposition using organic metals (MOCVD method), so the composition can be controlled relatively easily by controlling the proportion of the organic metal raw material introduced into the reaction chamber. can do. Accordingly, it is relatively easy to bring the peak wavelength of light emission of the blue LED into the range of 430 to 480 nm, or to bring the peak wavelength of light emission of the red LED into the range of 600 to 660 nm.

  In addition to these LEDs, it is also possible to use a phosphor material that emits light of each color.

The features of the present invention will be described more specifically with reference to examples and comparative examples. The materials, amounts used, ratios, processing details, processing procedures, and the like shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be construed as being limited by the specific examples shown below. In the following, “part” means part by weight unless otherwise specified.
Hereinafter, specific examples of producing a curable coloring composition and a color filter are shown.

Each component used for preparation of a use material curable coloring composition is shown below.
(Y-1) C.I. I. Pigment Yellow 150 (12.8 parts) and acrylic pigment dispersant (7.2 parts) are mixed with propylene glycol monomethyl ether acetate (80.0 parts), and the pigment is sufficiently dispersed using a bead mill. Pigment dispersion (Y-2) C.I. I. Solvent Yellow 162 (10.0 parts) dissolved in propylene glycol monomethyl ether acetate (90.0 parts) (T-1) Photopolymerizable compound: Kayalad DPHA (manufactured by Nippon Kayaku Co., Ltd .; dipentaerythritol A mixture of pentaacrylate and dipentaerythritol hexaacrylate)
(U-1) Binder resin: benzyl methacrylate / methacrylic acid (75/25 [mass ratio] copolymer (weight average molecular weight: 12,000) in propylene glycol monomethyl ether acetate solution (solid content: 40.0 mass%)
(V-1) Photopolymerization initiator: 2- (benzoyloxyimino) -1- [4- (phenylthio) phenyl] -1-octanone (V-2) Photopolymerization initiator: 2- (acetoxyimino) -4 -(4-Chlorophenylthio) -1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] -1-butanone (W-1) photopolymerization initiation assistant: 4,4 '-Bis (diethylamino) benzophenone (X-1) Solvent: Propylene glycol monomethyl ether acetate (X-2) Solvent: Ethyl 3-ethoxypropionate (Y-1) Surfactant: Megafac F781-F (Dainippon Ink (Chemical Industry Co., Ltd.)

Preparation and evaluation of cyan colored film Preparation of curable coloring composition (coating liquid) The components in the following composition were mixed to prepare curable coloring composition 1.
<Composition>
-Compound A-1 ... 6.9 parts by mass-(T-1) ... 103.4 parts by mass-(U-1) ... 212.2 parts by mass (solid content conversion value: (84.9 parts by mass)
-(V-1) ... 21.2 parts by mass-(W-1) ... 3.5 parts by mass-(X-1) ... 71.9 parts by mass-(X- 2) ... 3.6 parts by mass, (Y-1) ... 0.06 parts by mass

2. Preparation of colored film by curable coloring composition The curable coloring composition (color resist solution) obtained in 1 above is placed on a 100 mm × 100 mm glass substrate (1737, manufactured by Corning) so that the maximum absorbance at 600 to 700 nm is 1.5 to 2.0. It was applied and dried in an oven at 100 ° C. for 180 seconds to produce a colored film on the substrate (Example 1).

  The substrates of Examples 2 to 7 and Comparative Examples 1 to 3 were prepared and evaluated in the same manner as in Example 1 by replacing Compound 1 with the compounds shown in Table 1 below.

3. Evaluation of colored film by curable coloring composition The following evaluation was performed about the board | substrate obtained above.
<Evaluation of hue>
About the produced colored film, absorption at 550 nm and 650 nm is measured with an ultraviolet-visible spectrophotometer (Shimadzu Corporation UV2400-PC), thereby obtaining a transmittance ratio (550 nm / 650 nm), and according to the following criteria, four steps It was evaluated with. The evaluation results are shown in Table 1 below.
Evaluation criteria: ○ Transmission ratio less than 0.1
△ Transmittance ratio 0.1 or more, less than 0.3
× Transmittance ratio 0.3 or more and less than 1.0
XX Transmission ratio 1.0 or more

<Evaluation of heat resistance>
The heat resistance of the substrates produced in Examples 1 to 7 was evaluated. Heating was performed at 150 ° C. for 5 minutes on a hot plate. All the substrates produced in Examples 1 to 7 have a residual ratio of the dye compound of 90% or more, and were confirmed to be excellent in heat resistance.

Preparation and evaluation of green colored film Preparation of curable coloring composition (coating liquid) The components in the following composition were mixed to prepare a curable coloring composition.
<Composition>
Compound A-1: 6 parts by mass Yellow pigment compound Y-1: Absorption intensity ratio (absorption at 450 nm / absorption at 650 nm)
Yellow pigment compound to be in the range of 0.95 to 1.05
The amount of material was adjusted and added.
-(T-1) ... 103.4 parts by mass-(U-1) ... 212.2 parts by mass (solid content conversion value: 84.9 parts by mass)
-(V-1) ... 21.2 parts by mass-(W-1) ... 3.5 parts by mass-(X-1) ... 71.9 parts by mass-(X- 2) ... 3.6 parts by mass, (Y-1) ... 0.06 parts by mass

2. Preparation of colored film by curable coloring composition The curable coloring composition (color resist solution) obtained in 1 above is placed on a 100 mm × 100 mm glass substrate (1737, manufactured by Corning) so that the maximum absorbance at 600 to 700 nm is 1.5 to 2.0. It was applied and dried in an oven at 100 ° C. for 180 seconds to produce a colored film on the substrate (Example 101).

  Substrates of Examples 102 to 114 and Comparative Examples 101 to 106 were prepared and evaluated in the same manner as Example 101 by replacing Compound 1 and yellow dye compound Y-1 with those described in Table 2 below.

3. Evaluation of colored film by curable coloring composition The following evaluation was performed about the board | substrate obtained above.
<Evaluation of hue>
About the produced colored film, absorption was measured with the ultraviolet visible spectrophotometer (Shimadzu Corporation UV2400-PC), transmittance | permeability ratio (550nm / 650nm) was calculated | required, and it evaluated in four steps according to the same standard as the above. The evaluation results are shown in Table 2 below.

<Evaluation of heat resistance>
The heat resistance of the substrates produced in Examples 101 to 114 was evaluated. Heating was performed at 150 ° C. for 5 minutes on a hot plate. It was confirmed that all the substrates prepared in Examples 101 to 114 had excellent heat resistance with a residual ratio of cyan dye compounds (displayed in the column of “Compound” in Table 2) of 90% or more. It was done.

From the above examples, it was confirmed that a green filter excellent in contrast between the transmissive part and the non-transmissive part and excellent in heat resistance can be produced with the compound of the present invention.
In addition, the color filter produced using the curable coloring composition of the above examples has high color purity, a high absorption coefficient in a thin layer, fastness (particularly heat resistance and light resistance), and voltage holding ratio. Excellent. Furthermore, a liquid crystal display device and a solid-state imaging device manufactured using the color filter have a vivid color and a high contrast.

Claims (10)

The curable coloring composition characterized by containing the pigment | dye compound represented with the following general formula (A).

[In General Formula (A), Z represents a nitrogen atom or -C (R < ¹ >)-. R ¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group, a hydrogen atom, or an aromatic ring which may have a substituent. Q ¹ represents a nitrogen atom or —C (R ¹⁴ ) —. Q ² represents a nitrogen atom or —C (R ²⁴ ) —. R ² , R ³ , R ⁴ and R ⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ¹¹ , R ¹³ , R ¹⁴ , R ²¹ , R ²² , R ²³ and R ²⁴ each independently represent a substituent. R ² , R ³ , R ⁴ and R ⁵ together with R ¹² , R ¹³ , R ²² and R ²³ each have an alkylene group or a substituent which may have a substituent independently. A vinylene group which may be substituted, or a propenylene group which may have a substituent may be formed. Y represents an atom or an atomic group constituting an anion. The general formula (A) satisfies any one of the following conditions (1) to (7).
(1) Z represents —C (R ¹ ) —. R ¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group or a hydrogen atom. Q ¹ represents —C (R ¹⁴ ) —. Q ² represents —C (R ²⁴ ) —. R ² together with R ¹² represents an alkylene group which may have a substituent, a vinylene group which may have a substituent, or a propenylene group which may have a substituent. R ³ , R ⁴ and R ⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ³ , R ⁴ and R ⁵ together with R ¹³ , R ²² and R ²³ are each independently an alkylene group which may have a substituent, or vinylene which may have a substituent. A propenylene group which may have a group or a substituent may be formed.
(2) Z represents —C (R ¹ ) —. R ¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group or a hydrogen atom. Q ¹ represents —C (R ¹⁴ ) —. Q ² represents —C (R ²⁴ ) —. R ¹⁴ and R ²⁴ together represent a methylene group optionally having a substituent, —O—, —SO ₂ —, or a silylene group optionally having a substituent. R ² together with R ¹² represents an alkylene group which may have a substituent, a vinylene group which may have a substituent, or a propenylene group which may have a substituent. R ³ , R ⁴ and R ⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ³ , R ⁴ and R ⁵ together with R ¹³ , R ²² and R ²³ are each independently an alkylene group which may have a substituent, or vinylene which may have a substituent. A propenylene group which may have a group or a substituent may be formed.
(3) Z represents —C (R ¹ ) —. R ¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group or a hydrogen atom. Q ¹ represents —C (R ¹⁴ ) —. Q ² represents —C (R ²⁴ ) —. R ¹⁴ and R ²⁴ together represent —SO ₂ —. R ² , R ³ , R ⁴ and R ⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ² , R ³ , R ⁴ and R ⁵ together with R ¹² , R ¹³ , R ²² and R ²³ each have an alkylene group or a substituent which may have a substituent independently. A vinylene group which may be substituted, or a propenylene group which may have a substituent may be formed.
(4) Z represents a nitrogen atom. Q ¹ represents —C (R ¹⁴ ) —. Q ² represents —C (R ²⁴ ) —. R ¹⁴ and R ²⁴ together represent a methylene group optionally having a substituent, —O—, —SO ₂ —, or a silylene group optionally having a substituent. R ² represents an alkylene group which may have a substituent, a vinylene group which may have a substituent, or a propenylene group which may have a substituent. R ³ , R ⁴ and R ⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ³ , R ⁴ and R ⁵ together with R ¹³ , R ²² and R ²³ are each independently an alkylene group which may have a substituent, or vinylene which may have a substituent. A propenylene group which may have a group or a substituent may be formed.
(5) Z represents —C (R ¹ ) —. R ¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group or a hydrogen atom. Q ¹ and Q ² represent a nitrogen atom. R ² , R ³ , R ⁴ and R ⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ² , R ³ , R ⁴ and R ⁵ together with R ¹² , R ¹³ , R ²² and R ²³ each have an alkylene group or a substituent which may have a substituent independently. A vinylene group which may be substituted, or a propenylene group which may have a substituent may be formed.
(6) Z represents —C (R ¹ ) —. R ¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group or a hydrogen atom. Q ¹ and Q ² represent nitrogen atoms, and these nitrogen atoms are bonded to an atomic group represented by> M- [L] n. M represents a metal atom. L represents a ligand. n represents any natural number of 1 to 4. R ² , R ³ , R ⁴ and R ⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ² , R ³ , R ⁴ and R ⁵ together with R ¹² , R ¹³ , R ²² and R ²³ each have an alkylene group or a substituent which may have a substituent independently. A vinylene group which may be substituted, or a propenylene group which may have a substituent may be formed.
(7) Z represents -C (R < ¹ >)-. R ¹ represents an aromatic ring substituted with —N (R ³¹ ) (R ³² ). Q ¹ represents —C (R ¹⁴ ) —. Q ² represents —C (R ²⁴ ) —. At least one combination of R ¹¹ and R ¹² , R ¹² and R ² , R ¹² and R ³ , R ³ and R ¹³ , and R ¹³ and R ¹⁴ together forms an aromatic ring. Represents the atomic group necessary for. At least one combination of R ²¹ and R ²² , R ²² and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ²³ , and R ²³ and R ²⁴ together forms an aromatic ring. Represents the atomic group necessary for. R ² , R ³ , R ⁴ , R ⁵ , R ³¹ and R ³² are each independently an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom Represents. ] A curable coloring composition comprising a dye compound represented by any one of the following general formulas (1) to (7).

[In General Formula (1), R ¹⁰¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group or a hydrogen atom. ^R102 represents an alkylene group which may have a substituent, a vinylene group which may have a substituent, or a propenylene group which may have a substituent. R ¹⁰³ , R ¹⁰⁴ and R ¹⁰⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ¹¹¹ , R ¹¹³ , R ¹¹⁴ , R ¹²¹ , R ¹²² , R ¹²³ and R ¹²⁴ each independently represent a substituent. R ¹⁰³ , R ¹⁰⁴ and R ¹⁰⁵ together with R ¹¹³ , R ¹²² and R ¹²³ are each independently an alkylene group which may have a substituent, or vinylene which may have a substituent. A propenylene group which may have a group or a substituent may be formed. Y represents an atom or an atomic group constituting an anion. ]

[In the general formula (2), X ²⁰¹ is may have a substituent group methylene _{group, -O -, - SO 2 -} , or an optionally substituted group represents an silylene group. R ²⁰¹ represents an aryl group that may have a substituent, an alkyl group that may have a substituent, a cyano group, or a hydrogen atom. R ²⁰² represents an alkylene group which may have a substituent, a vinylene group which may have a substituent, or a propenylene group which may have a substituent. R ²⁰³ , R ²⁰⁴ and R ²⁰⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ²¹¹ , R ²¹³ , R ²²¹ , R ²²² and R ²²³ each independently represent a substituent. R ²⁰³ , R ^204, and R ²⁰⁵ together with R ²¹³ , R ²²² , and R ²²³ are each independently an alkylene group that may have a substituent, or vinylene that may have a substituent. A propenylene group which may have a group or a substituent may be formed. Y represents an atom or an atomic group constituting an anion. ]

[In General Formula (3), R ³⁰¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group or a hydrogen atom. R ³⁰² , R ³⁰³ , R ³⁰⁴ and R ³⁰⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ³¹¹ , R ³¹² , R ³¹³ , R ³²¹ , R ³²² and R ³²³ each independently represent a substituent. R ³⁰² , R ³⁰³ , R ^304, and R ³⁰⁵ together with R ³¹² , R ³¹³ , R ³²² , and R ³²³ have an alkylene group and a substituent that may each independently have a substituent. A vinylene group which may be substituted, or a propenylene group which may have a substituent may be formed. Y represents an atom or an atomic group constituting an anion. ]

[In General Formula (4), X ⁴⁰¹ represents an optionally substituted methylene group, —O—, —SO ₂ —, or an optionally substituted silylene group. R ⁴⁰² represents an alkylene group which may have a substituent, a vinylene group which may have a substituent, or a propenylene group which may have a substituent. R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ⁴¹¹ , R ⁴¹³ , R ⁴²¹ , R ⁴²² and R ⁴²³ each independently represent a substituent. R ⁴⁰³ , R ⁴⁰⁴ and R ⁴⁰⁵ together with R ⁴¹³ , R ⁴²² and R ⁴²³ are each independently an alkylene group which may have a substituent, or vinylene which may have a substituent. A propenylene group which may have a group or a substituent may be formed. Y represents an atom or an atomic group constituting an anion. ]

[In General Formula (5), R ⁵⁰¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group or a hydrogen atom. R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ and R ⁵⁰⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ⁵¹¹ , R ⁵¹² , R ⁵¹³ , R ⁵²¹ , R ⁵²² and R ⁵²³ each independently represent a substituent. R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ and R ⁵⁰⁵ together with R ⁵¹² , R ⁵¹³ , R ⁵²² and R ⁵²³ have an alkylene group and a substituent which may each independently have a substituent. A vinylene group which may be substituted, or a propenylene group which may have a substituent may be formed. Y represents an atom or an atomic group constituting an anion. ]

[In General Formula (6), R ⁶⁰¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group or a hydrogen atom. R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ and R ⁶⁰⁵ each independently represent an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ⁶¹¹ , R ⁶¹² , R ⁶¹³ , R ⁶²¹ , R ⁶²² and R ⁶²³ each independently represent a substituent. R ⁶⁰² , R ⁶⁰³ , R ^604, and R ⁶⁰⁵ each have an alkylene group or a substituent that may be independently substituted with R ⁶¹² , R ⁶¹³ , R ⁶²² , or R ⁶²³ , respectively. A vinylene group which may be substituted, or a propenylene group which may have a substituent may be formed. M represents a metal atom. L represents a ligand. n represents any natural number of 1 to 4. Y represents an atom or an atomic group constituting an anion. ]

[In General Formula (7), Ar ⁷⁰¹ and Ar ⁷⁰² each independently represent an aromatic ring in which two or more rings optionally having a substituent are condensed. Ar ⁷⁰³ represents an aromatic ring which may have a substituent. R ⁷⁰¹ , R ⁷⁰² , R ⁷⁰³ , R ⁷⁰⁴ , R ⁷⁰⁵ and R ⁷⁰⁶ are each independently an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom Represents. Y represents an atom or an atomic group constituting an anion. ]   The curable coloring composition according to claim 1 or 2, wherein the curable coloring composition contains a yellow pigment compound.   The curable coloring composition according to claim 1, comprising a monomer and a polymerization initiator.   The color filter produced by forming the colored layer using the curable coloring composition of any one of Claims 1-4.   The color which has the process of apply | coating the curable coloring composition of any one of Claims 1-4 on a support body, forming a colored layer, and exposing the formed colored layer in pattern form A method for manufacturing a filter.   A liquid crystal display device comprising the color filter according to claim 5 or the color filter produced by the manufacturing method according to claim 6.   The solid-state image sensor provided with the color filter of the color filter of Claim 5, or the color filter produced by the manufacturing method of Claim 6. A compound having a structure represented by the following general formula (5).

[In General Formula (5), R ⁵⁰¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group or a hydrogen atom. R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ and R ⁵⁰⁵ each independently represents an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ⁵¹¹ , R ⁵¹² , R ⁵¹³ , R ⁵²¹ , R ⁵²² and R ⁵²³ each independently represent a substituent. R ⁵⁰² , R ⁵⁰³ , R ⁵⁰⁴ and R ⁵⁰⁵ together with R ⁵¹² , R ⁵¹³ , R ⁵²² and R ⁵²³ have an alkylene group and a substituent which may each independently have a substituent. A vinylene group which may be substituted, or a propenylene group which may have a substituent may be formed. Y represents an atom or an atomic group constituting an anion. ] A compound having a structure represented by the following general formula (6).

[In General Formula (6), R ⁶⁰¹ represents an aryl group which may have a substituent, an alkyl group which may be substituted with a halogen atom, a cyano group or a hydrogen atom. R ⁶⁰² , R ⁶⁰³ , R ⁶⁰⁴ and R ⁶⁰⁵ each independently represent an aryl group which may have a substituent, an alkyl group which may have a substituent, or a hydrogen atom. R ⁶¹¹ , R ⁶¹² , R ⁶¹³ , R ⁶²¹ , R ⁶²² and R ⁶²³ each independently represent a substituent. R ⁶⁰² , R ⁶⁰³ , R ^604, and R ⁶⁰⁵ each have an alkylene group or a substituent that may be independently substituted with R ⁶¹² , R ⁶¹³ , R ⁶²² , or R ⁶²³ , respectively. A vinylene group which may be substituted, or a propenylene group which may have a substituent may be formed. M represents a metal atom. L represents a ligand. n represents any natural number of 1 to 4. Y represents an atom or an atomic group constituting an anion. ]