KR20140106416A - Coloring composition, colored cured film and display device - Google Patents

Abstract

The present invention provides a coloring composition including a dye, having both heat resistance and solvent resistance, and is appropriate to use for forming a colored and cured film with restrained methachromasy. The coloring composition of the present invention includes (A) a coloring agent and (C) a polymerizable compound. The coloring agent includes a polymer with a structure unit represented by the following Formula (I). [In Formula (1), R^0 represents a hydrogen atom or a methyl group. X represents a halogen group, a halogenated hydrocarbon group or a group with a connecting group including an atom other than a carbon atom, a hydrogen atom or a halogen atom between C-C bond of the halogenated hydrocarbon group. Y represents a single bond or a divalent organic group. Z^+ represents at least one cationic chromophore selected from the group consisting of a triarylmethane-based cationic chromophore, a methine-based cationic chromophore, an azo-based cationic chromophore, a diarylmethane-based cationic chromophore, a quinoneimine-based cationic chromophore, an anthraquinone-based cationic chromophore, a phthalocyanine-based cationic chromophore, and a xanthines-based cationic chromophore.].

Description

TECHNICAL FIELD [0001] The present invention relates to a colored composition, a colored cured film,

The present invention relates to a colored composition, a colored cured film and a display device, and more particularly to a colored curable film used for a transmissive or reflective color liquid crystal display device, a solid-state image sensor, an organic EL display device, , A colored cured film formed using the colored composition, and a display element comprising the colored cured film.

When a color filter is manufactured using a coloring and radiation-sensitive composition, a pigment-dispersed coloring and radiation-sensitive composition is applied onto a substrate and dried, and then the dry film is irradiated with a desired pattern (hereinafter, (Refer to, for example, Patent Documents 1 and 2) are known. A method of forming a black matrix using a photopolymerizable composition in which carbon black is dispersed (see, for example, Patent Document 3) is also known. There is also known a method of obtaining pixels of respective colors by an ink jet method using a pigment dispersion type colored resin composition (see, for example, Patent Document 4).

In recent years, there has been a strong demand for high-contrast liquid crystal display elements and high-definition solid-state image pickup devices. In order to realize these, application of dyes as colorants has been studied. Generally speaking, however, when a dye is applied as compared with the case where a pigment is applied as a coloring agent, there are many cases where problems such as heat resistance and solvent resistance occur.

Under such background, use of a triarylmethane-based dye having an alkylsulfonylimide anion as a dye-containing coloring composition capable of forming a pixel having excellent heat resistance, for example, in Patent Document 5 has been proposed.

Japanese Patent Application Laid-Open No. 2-144502 Japanese Patent Laid-Open Publication No. 3-53201 Japanese Patent Application Laid-Open No. 6-35188 Japanese Patent Application Laid-Open No. 2000-310706 Japanese Patent Application Laid-Open No. 8-3652

However, in the dye proposed in Patent Document 5, it has been found that the balance between heat resistance and solvent resistance of a pixel is poor. Further, the inventors of the present invention have found that a dye in a pixel of a coloring pattern is colored (hereinafter also referred to as " transferring property ") to a cured film containing no coloring agent such as a pixel of another color adjacent thereto, , There is a problem that the display characteristics of the display element are degraded. However, this problem is not considered in Patent Document 5 at all.

Accordingly, an object of the present invention is to provide a coloring composition which is compatible with both heat resistance and solvent resistance, and which is suitable for forming a colored cured film with inhibited dye transferability. It is still another object of the present invention to provide a colored cured film formed using the colored composition and a display device having the colored cured film.

As a result of intensive studies, the present inventors have found that the above problems can be solved by using a colorant having a specific structure.

That is, the present invention relates to a colored composition comprising (A) a colorant and (C) a polymerizable compound, wherein the colorant is a polymer having a structural unit represented by the following formula (1) And a coloring composition containing the same.

[In the formula (1)

R ⁰ represents a hydrogen atom or a methyl group,

X represents a group having a linking group containing a carbon atom, a hydrogen atom or an atom other than a halogen atom between C-C bonds of a halo group, a halogenated hydrocarbon group, or a halogenated hydrocarbon group,

Y represents a single bond or a divalent organic group,

Z ⁺ is a triarylmethane type cationic chromophore represented by the following formula (2-1), a triarylmethane type cationic chromophore represented by the following formula (2-2), a methine type cationic chromophore, At least one selected from the group consisting of a cationic chromophore of a cationic chromophore, a cationic chromophore of a diarylmethane series, a cationic chromophore of a quinone imine series, a cationic chromophore of an anthraquinone series, a cationic chromophore of a phthalocyanine series and a cationic chromophore of a xanthene series One kind of cationic chromophore]

[In the formula (2-1)

R ¹ to R ⁶ independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 8 carbon atoms, or a substituted or unsubstituted aryl group,

R ⁷ to R ⁹ independently represent an alkyl group or a chlorine atom having 1 to 8 carbon atoms,

l and m independently represent an integer of 0 to 4,

n represents an integer of 0 to 6,

Provided that l, m and n are 0 at the same time]

In the formula (2-2)

R ¹¹ to R ¹⁶ independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 8 carbon atoms, or a substituted or unsubstituted aryl group,

R ¹⁷ to R ¹⁹ independently represent an alkyl group having 1 to 8 carbon atoms or a chlorine atom,

s, t and u independently represent an integer of 0 to 4)

The present invention also provides a display device comprising the colored cured film formed by using the colored composition and the colored cured film. Here, the term "colored cured film" means a color pixel, a black matrix, a black spacer, etc. used in a display element or a solid-state image pickup element.

When the coloring composition of the present invention is used, it is possible to form a colored cured film having both heat resistance and solvent resistance at a high level and inhibiting the dyeing.

Accordingly, the coloring composition of the present invention can be suitably used for the production of solid-state image pickup devices such as color liquid crystal display devices, organic EL display devices, display devices such as electronic paper, and CMOS image sensors.

Hereinafter, the present invention will be described in detail.

Coloring composition

Hereinafter, the constituent components of the coloring composition of the present invention will be described in detail.

- (A) Colorant -

The coloring composition of the present invention contains a polymer having a structural unit represented by the following formula (1) as a colorant.

[In the formula (1)

R ⁰ represents a hydrogen atom or a methyl group,

X represents a group having a linking group containing a carbon atom, a hydrogen atom or an atom other than a halogen atom between C-C bonds of a halo group, a halogenated hydrocarbon group, or a halogenated hydrocarbon group,

Y represents a single bond or a divalent organic group,

Z ⁺ is a triarylmethane type cationic chromophore represented by the following formula (2-1), a triarylmethane type cationic chromophore represented by the following formula (2-2), a methine type cationic chromophore, At least one selected from the group consisting of a cationic chromophore of a cationic chromophore, a cationic chromophore of a diarylmethane series, a cationic chromophore of a quinone imine series, a cationic chromophore of an anthraquinone series, a cationic chromophore of a phthalocyanine series and a cationic chromophore of a xanthene series One kind of cationic chromophore]

R ⁰ is preferably a hydrogen atom or a methyl group in the methyl group.

Examples of the halo group in X include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

Examples of the hydrocarbon group constituting the skeleton of the halogenated hydrocarbon group in X include (1) an aliphatic hydrocarbon group, (2) an alicyclic hydrocarbon group, (3) an aliphatic hydrocarbon group having an alicyclic hydrocarbon group as a substituent (5) an aromatic hydrocarbon group having an aliphatic hydrocarbon group as a substituent (hereinafter referred to as an "aliphatic hydrocarbon-substituted aromatic hydrocarbon group"); (6) an aromatic hydrocarbon group having an aliphatic hydrocarbon-substituted aliphatic hydrocarbon group And an aliphatic hydrocarbon group having an aromatic hydrocarbon group (hereinafter referred to as an " aromatic hydrocarbon-substituted aliphatic hydrocarbon group "). The hydrocarbon group constituting the skeleton of the halogenated hydrocarbon group is preferably the following characteristic group from the viewpoint of solubility in an organic solvent.

That is, the aliphatic hydrocarbon group (1) is preferably an alkyl group, and the alkyl group may be a straight chain or branched chain. The alkyl group preferably has 1 to 20 carbon atoms, and more preferably 1 to 8 carbon atoms. Specific examples thereof include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert- Pentyl group, n-hexyl group, n-heptyl group, n-octyl group and the like.

The alicyclic hydrocarbon group (2) may be a bicyclic to tricyclic bridged alicyclic hydrocarbon group. The alicyclic hydrocarbon group is preferably an alicyclic saturated hydrocarbon group having 3 to 20 carbon atoms and more preferably 3 to 12 carbon atoms. Specific examples thereof include a cycloalkyl group such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group and cyclododecyl group, a norbornyl group, a boronyl group, an adamantyl group, And a bicyclooctyl group.

The (3) alicyclic hydrocarbon-substituted aliphatic hydrocarbon group is preferably an alicyclic saturated hydrocarbon-substituted alkyl group, and the number of carbon atoms thereof is preferably from 4 to 20, particularly preferably from 6 to 14. Specific examples thereof include a cyclopropylmethyl group, a cyclobutylmethyl group, a cyclohexylmethyl group, a cyclohexylpropyl group, an adamantylmethyl group, a 1- (1-adamantyl) ethyl group, and a cyclopentylethyl group.

The aromatic hydrocarbon group (4) is preferably an aryl group having 6 to 14 carbon atoms and more preferably 6 to 10 carbon atoms. Specific examples thereof include a phenyl group, a naphthyl group, a biphenyl group, a fluorenyl group, and an anthracenyl group. Of these, a phenyl group is preferable.

The aliphatic hydrocarbon-substituted aromatic hydrocarbon group (5) is preferably an alkyl-substituted phenyl group, preferably 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms. Specific examples thereof include a tolyl group, a xylyl group, mesityl, and the like.

The aromatic hydrocarbon-substituted aliphatic hydrocarbon group (6) is preferably an aralkyl group, preferably 7 to 30 carbon atoms, more preferably 7 to 20 carbon atoms. Specific examples thereof include a benzyl group and a phenethyl group.

In addition, the alkyl group in this specification may be straight chain or branched.

(3) an alicyclic hydrocarbon-substituted aliphatic hydrocarbon group, (4) an aromatic hydrocarbon group, (5) an aliphatic hydrocarbon-substituted aromatic hydrocarbon group, or (5) an aliphatic hydrocarbon- 6) an aromatic hydrocarbon-substituted aliphatic hydrocarbon group is preferable, and an alkyl group, an alicyclic saturated hydrocarbon-substituted alkyl group, a phenyl group, an alkyl-substituted phenyl group and an aralkyl group are more preferable, and an alkyl group is particularly preferable.

As the halogen atom in the halogenated hydrocarbon group in X, a fluorine atom is preferable from the viewpoint of the heat resistance of the colorant, and the fluorine atom may substitute some or all of the hydrogen atoms of the hydrocarbon group. By selecting a fluorine atom as a substituent, it is considered that a salt having a stronger ion binding force is formed and the heat resistance is increased.

X may be a group having a linking group containing a carbon atom, a hydrogen atom or an atom other than a halogen atom among the CC bonds of the halogenated hydrocarbon group. As the linking group containing an atom other than a carbon atom, a hydrogen atom or a halogen atom, , -S-, -CO-, -COO-, -CONH-, -SO ₂ - and the like. The carbon number described in paragraphs <0045> to <0051> means the total carbon number of the part excluding the carbon atoms constituting the linking group.

From the viewpoint of heat resistance of the colorant in the present invention, X is preferably a group having a linking group containing a carbon atom, a hydrogen atom or an atom other than a halogen atom among CC bonds of a halogenated hydrocarbon group or a halogenated hydrocarbon group, ) Or (4) is more preferable, and a group represented by the following formula (3) which forms a conjugate base of an organic acid having a stronger acidity is particularly preferable.

[In the formula (3)

R ²⁰ represents a hydrogen atom, a fluorine atom, an alkyl group, an alkyl fluoride group, an alicyclic hydrocarbon group, an alkoxy group, an alkoxy group, R ²¹ COOR ²² - or R ²³ COOR ²⁴ CFH-,

R ²¹ and R ²³ independently represent an alkyl group, an alicyclic hydrocarbon group, a heteroaryl group, or a substituted or unsubstituted aryl group,

R ²² and R ²⁴ independently represent an alkanediyl group,

q represents an integer of 1 or more,

"*" Indicates a combined hand)

[In the formula (4)

R ²⁵ to R ²⁹ independently represent a hydrogen atom, a fluorine atom, a hydroxyl group, an alkyl group, an alkyl fluoride group or an alkoxy group,

The &quot; * &quot; indicates a combined hand,

Provided that at least one of R ²⁵ to R ²⁹ is a fluorine atom or an alkyl fluoride group]

In the formula (3), as the alkyl group for R ²⁰ , an alkyl group having 1 to 20 carbon atoms, more preferably 1 to 8 carbon atoms, further preferably 1 to 4 carbon atoms is preferable. The alkyl group may be a straight chain or branched chain. Specific examples include the same ones as described above.

The fluorinated alkyl group for R ²⁰ is preferably a fluorinated alkyl group having 1 to 20 carbon atoms, more preferably 1 to 8 carbon atoms and further 1 to 4 carbon atoms. The fluorinated alkyl group may be a straight chain or branched chain. Specific examples thereof include those in which a part or all of the hydrogen atoms of the above-mentioned alkyl groups are substituted with fluorine atoms, and in particular, a perfluoroalkyl group is preferable.

The alicyclic hydrocarbon group for R ²⁰ may be a divalent to tetravalent bridged alicyclic hydrocarbon group. The alicyclic hydrocarbon group is preferably an alicyclic saturated hydrocarbon group having 3 to 20 carbon atoms and more preferably 3 to 12 carbon atoms. Specific examples include the same ones as described above.

As the alkoxy group for R ²⁰ , an alkoxy group having 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms and further 1 to 4 carbon atoms is preferred. The alkoxy group may be a straight chain or branched chain. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, tert-butoxy, sec- A siloxane group, a methoxymethoxy group, an ethoxyethoxy group, and a 3- (iso-propyloxy) propyloxy group.

The fluorinated alkoxy group for R ²⁰ is preferably a fluorinated alkoxy group having 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms and further 1 to 4 carbon atoms. The fluorinated alkoxy group may be a straight chain or branched chain. As a specific example, a part or all of hydrogen atoms of the above-mentioned alkoxy group may be substituted with a fluorine atom, and a perfluoroalkoxy group is particularly preferable.

R ²¹ COOR ²² in R ²⁰ - in, R ²³ COOR ²⁴ CFH-, R ²¹ and R ²³ are independently alkyl groups each other, represent an alicyclic hydrocarbon group, heteroaryl group, or a substituted or unsubstituted aryl group, the alkyl group is May be linear or branched, and the number of carbon atoms of the alkyl group is preferably from 1 to 12, more preferably from 1 to 8. Specific examples include the same ones as described above. The alicyclic hydrocarbon group may be a bicyclic to tricyclic bridged alicyclic hydrocarbon group or an alicyclic saturated hydrocarbon group having 3 to 20 carbon atoms and further preferably 3 to 12 carbon atoms. As the heteroaryl group, a group composed of a 5-10 membered aromatic heterocycle containing at least one hetero atom selected from a nitrogen atom, an oxygen atom and a sulfur atom is preferable. Specific examples include furyl, thienyl, pyrrolyl, oxazolyl, pyridyl, quinolinyl and carbazolyl groups. As the aryl group, an aryl group having 6 to 14 carbon atoms and more preferably 6 to 10 carbon atoms is preferable, and a phenyl group is particularly preferable. The substituent of the aryl group includes, for example, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a halogen atom or a trifluoromethyl group, and the position and number of substituents are arbitrary. Or more, the substituents may be the same or different.

R ²² and R ²⁴ independently represent an alkanediyl group, and a straight or branched alkanediyl group having 1 to 10 carbon atoms is preferred. Specific examples include methylene, ethylene, ethane-1,1-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, A butane-1,3-diyl group, a butane-1,4-diyl group, a pentane-1,4-diyl group, a pentane-1,5-diyl group, -1,5-diyl group, hexane-1,6-diyl group, octane-1,8-diyl group, decane-1,10-diyl group and the like. Among them, an alkanediyl group having 2 to 6 carbon atoms is preferable, and an alkanediyl group having 2 to 4 carbon atoms is more preferable. Of these, an ethylene group is preferable from the viewpoint of ease of production.

The upper limit of q is preferably 10, more preferably 8.

R ^{20 is preferably a} fluorine atom, an alkyl fluoride group, an alicyclic hydrocarbon group, an alkoxy fluoride group, R ²¹ COOR ²² - or R ²³ COOR ²⁴ CFH-, and more preferably a fluorine atom, an alicyclic hydrocarbon group, a perfluoroalkoxy group, R ²¹ COOCH ₂ CH ₂ - or R ²³ COOCH ₂ CH ₂ CFH-.

The alkyl group, fluorinated alkyl group and alkoxy group in R ²⁵ to R ²⁹ in the formula (4) may have the same configuration as the alkyl group, fluorinated alkyl group and alkoxy group in R ²⁰ in the above-described formula (3). Provided that at least one of R ²⁵ to R ²⁹ is the fluorine atom or fluorinated alkyl group, preferably an R ²⁵ to R ^29, at least three fluorine atoms or fluorinated alkyl group.

As the divalent organic group in Y, a divalent hydrocarbon group, a group formed by combining a divalent hydrocarbon group and a linking group containing an atom other than a carbon atom and a hydrogen atom, or a group in which a part of the hydrogen atoms of these groups are substituted with a halogen atom . Examples of such an organic group include an alkanediyl group having 1 to 10 carbon atoms, an arylene group having 6 to 20 carbon atoms, an arylenealkanediyl group having 7 to 20 carbon atoms, an alkanediyl group having 1 to 10 carbon atoms, an alkanediyl group having 6 to 20 carbon atoms (Wherein R 'represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms) and -SO ₂ -, and at least one member selected from the group consisting of -O-, -S-, -COO-, -CONR' - And a group formed by combining at least one species.

Specific examples of the alkanediyl group include the same ones as described above. Among them, an alkanediyl group having 2 to 8 carbon atoms is preferable, and an alkanediyl group having 2 to 6 carbon atoms is more preferable.

Examples of the arylene group include a phenylene group, a naphthylene group, a biphenylene group, and an anthryl group. Among them, an arylene group having 6 to 10 carbon atoms is preferable, and a phenylene group is particularly preferable.

The arylenealkanediyl group is a divalent group formed by combining an arylene group and an alkanediyl group. As the arylenealkanediyl group, an arylenealkanediyl group having 7 to 15 carbon atoms is preferable, and an arylenealkanediyl group having 7 to 13 carbon atoms is more preferable from the viewpoint of availability of raw materials and ease of preparation. Specifically, for example, phenylene methylene group, phenylenedimaleimide methylene group, phenyl rental Lee methylene group, phenylene tetramethylene group, phenylene pentamethylene group, phenylene hexahydro-phenyl, such as methylene group alkylene C _{1 - 6} alkanediyl A diary can be heard. The arylenealkanediyl group includes orthoesters, meta-isomers and para-isomers, and para-isomers are preferred in view of low steric hindrance.

Also, at least one selected from an alkanediyl group having 1 to 10 carbon atoms and an arylene group having 6 to 20 carbon atoms, -O-, -S-, -COO-, -CONR '- (R' An alkyl group having 1 to 8 carbon atoms) and -SO ₂ -, at least one selected from an alkanediyl group having 1 to 10 carbon atoms and an arylene group having 6 to 20 carbon atoms, A group formed by combining at least one member selected from -O-, -COO- and -SO ₂ -, at least one member selected from an alkanediyl group having 1 to 10 carbon atoms and an arylene group having 6 to 20 carbon atoms, More preferably a group formed by combining at least one member selected from -O- and -SO ₂ -.

Next, Z ⁺ will be described.

Z ⁺ is a triarylmethane type cationic chromophore represented by the following formula (2-1), a triarylmethane type cationic chromophore represented by the following formula (2-2), a methine type cationic chromophore, At least one selected from the group consisting of a cationic chromophore of a cationic chromophore, a cationic chromophore of a diarylmethane series, a cationic chromophore of a quinone imine series, a cationic chromophore of an anthraquinone series, a cationic chromophore of a phthalocyanine series and a cationic chromophore of a xanthene series One kind of cationic chromophore.

There are various resonance structures in the triarylmethane-based cationic chromophore represented by the formula (2-1) and the triarylmethane-based cationic chromophore represented by the formula (2-2). In the present specification, (2-1) and (2-2) in the case where a resonance structure is present in the chromophore represented by the formula (2-1) or (2-2).

[In formulas (2-1) and (2-2)

R ¹ to R ⁶ and R ¹¹ to R ¹⁶ independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 8 carbon atoms, or a substituted or unsubstituted aryl Lt; / RTI &gt;

R ⁷ to R ⁹ and R ¹⁷ to R ¹⁹ independently represent an alkyl group or a chlorine atom having 1 to 8 carbon atoms,

l, m, s, t and u independently represent an integer of 0 to 4,

n represents an integer of 0 to 6,

Provided that l, m and n are 0 at the same time]

Specific examples of the alkyl group having 1 to 8 carbon atoms in R ¹ to R ⁹ and R ¹¹ to R ¹⁹ include the same ones as described above. Among them, an alkyl group having 1 to 4 carbon atoms is preferable, and a methyl group or an ethyl group is particularly preferable.

Specific examples of the cycloalkyl group having 3 to 8 carbon atoms in R ¹ to R ⁶ and R ¹¹ to R ¹⁶ include the same ones as described above. Among them, a cycloalkyl group having 4 to 6 carbon atoms is preferable, and a cyclohexyl group is particularly preferable.

The aryl group in R ¹ to R ⁶ and R ¹¹ to R ¹⁶ is preferably an aryl group having 6 to 14 carbon atoms and further having 6 to 10 carbon atoms. Specific examples thereof include the same ones as described above, and among them, a phenyl group is preferable.

Examples of the substituent of the alkyl group, cycloalkyl group and aryl group in R ¹ to R ⁶ and R ¹¹ to R ¹⁶ include an alkoxy group having 1 to 6 carbon atoms, a halogen atom or a trifluoromethyl group, and a cyano group, The aryl group may be substituted with an alkyl group having 1 to 6 carbon atoms. Specific examples of these substituents include the same ones as described above. The position and number of substituents are arbitrary, and when two or more substituents are present, the substituents may be the same or different.

As R ⁷ to R ⁹ and R ¹⁷ to R ¹⁹ , an alkyl group or a chlorine atom having 1 to 4 carbon atoms is preferable, an alkyl group having 1 to 4 carbon atoms is more preferable, and a methyl group or an ethyl group is particularly preferable.

In the formula (2-1), 1 and m are preferably an integer of 0 to 2, and n is preferably 0 or 1. Provided that l, m and n are not 0 at the same time. 1, m = 0, n = 0, l = 0, m = 0, n = 1, l = 2, m = 0, n = 0 A combination of l = 1, m = 1 and n = 0, a combination of l = 1, m = 1 and n = 0, m = 0, n = 1, a combination of l = 1, m = 1 and n = 0 is more preferable.

In the formula (2-2), s is preferably an integer of 0 to 2, t and u are preferably 0 or 1, and at least one of s, t and u is an integer of 1 to 4. The combination of s = 0, t = 0, u = 0, s = 1, t = 0, A combination of s = 1, t = 1 and u = 0, a combination of s = 1, t = 1 and u = = 1, a combination of t = 0 and u = 0, a combination of s = 1, t = 1 and u = 0 is more preferable.

Examples of the chromophore represented by the formula (2-1) or the chromophore represented by the formula (2-2) include chromophores represented by the following groups a and b, among which chromophore a1, a2, a3, a4, a5, a6, b1, b2, b3, b4 and b6 are preferable, and a2, a3, a4, a5, a6, b3 and b4 are more preferable.

[Compound group a]

[Compound group b]

In addition to the above, examples of the triarylmethane-based cationic chromophore represented by the formula (2-1) include a chromophore described in, for example, Japanese Patent Application Laid-Open Publication No. 147425/1993.

The methine chromophores are preferably represented by the following chemical formulas (5-1) to (5-3), and more preferably represented by Chemical Formula (5-1) below.

[In the formulas (5-1) to (5-3)

R ³¹ represents a hydrogen atom or a halo group,

R ³² , R ³³ , R ³⁴ and R ³⁵ independently represent an alkyl group having 1 to 6 carbon atoms,

R ³⁶ represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms,

G is -CH = CH-, -CH = CH- CH =, -CH = CH-NR 37 - (R 37 represents a hydrogen atom or an alkyl group having 1 to 6), -CH = N-NR 37 - ( R ³⁷ is the same as above) or -N = N-NR ³⁷ - (R ³⁷ is the same as above)

R ^a represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group]

As R ^a , groups represented by the following formulas (5a) to (5h) are preferable, and groups represented by the following formula (5b) or (5h) are more preferable.

In the formulas (5a) to (5h)

R ³⁸ and R ⁴⁵ independently represent an alkyl group having 1 to 6 carbon atoms,

R ³⁹ represents a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms,

R ⁴⁰ , R ⁴² , R ⁴³ , R ⁴⁴ , R ⁴⁷ , R ⁴⁸ and R ⁴⁹ independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,

R ⁴¹ , R ⁴⁶ and R ⁵⁰ independently represent a hydrogen atom, a halo group, an alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, a nitro group, a hydroxyl group or a cyano group]

The alkyl group in R ³² to R ⁵⁰ is preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group. Examples of the substituent of the alkyl group include a halo group, a cyano group, and a hydroxyl group. The halo group in R ³¹ , R ⁴¹ , R ⁴⁶ and R ⁵⁰ , the alkoxy group in R ⁴¹ , R ⁴⁶ and R ⁵⁰ is preferably an alkoxy group having 1 to 4 carbon atoms, more preferably a methoxy group or an ethoxy group Do.

Representative examples of chromophores represented by the formulas (5-1) to (5-3) include chromophores represented by the following group of compounds c.

[Compound group c]

Examples of the azo-based chromophore include those represented by the following formulas (6-1) to (6-6), preferably represented by the following formulas (6-1) to (6-5) 6-1).

[In formulas (6-1) to (6-6), &quot;

R ⁵¹ , R ⁵² , R ⁵³ , R ⁵⁴ , R ⁵⁵ and R ⁵⁷ independently represent a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms,

R ⁵⁶ and R ⁶⁰ independently represent a hydrogen atom, a halo group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a nitro group, a hydroxyl group or a cyano group,

R ⁵⁸ represents an alkyl group having 1 to 6 carbon atoms,

R &lt; ⁵⁹ &gt; represents a group forming quaternary ammonium,

R ^b represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group]

As _{^{R 59, -NR 61 C ma H}} 2ma N + R 62 R 63 R 64 (ma is an integer from 1 to 5, R ⁶¹ represents a hydrogen atom or an alkyl group having 1 to 6, R ^62, R ^63, and R ⁶⁴ represents independently an alkyl group having 1 to 6 carbon atoms from each ^{_{other), -COC ma H 2ma N +}} R 62 R 63 R 64 (ma, R 62, R 63 and R ⁶⁴ are synonymous with the Im), -C _ma H _2ma N ⁺ (NH ₂ ) R ⁷⁴ R ⁷⁵ wherein m is as defined above and R ⁷⁴ and R ⁷⁵ are independently of each other an alkyl group having 1 to 6 carbon atoms, -ii) is preferable.

[In formulas (6-i) and (6-ii), R ⁶¹ and ma are as defined above]

R ^b is preferably a group represented by the following formulas (6a) to (6e), a substituted or unsubstituted phenyl group, and more preferably a group represented by the following formula (6a). Examples of the substituent of the phenyl group include a halo group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a hydroxyl group, a cyano group and a nitro group.

[In the formulas (6a) to (6d)

R ⁶⁵ represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a phenyl group or a benzyl group,

R ⁶⁶ represents a hydrogen atom or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms,

R ⁶⁷ represents a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a phenyl group,

R ⁶⁸ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,

R ⁶⁹ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms,

R ⁷⁰ to R ⁷³ independently represent a hydrogen atom, a halo group, an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a nitro group, a hydroxyl group or a cyano group]

The alkyl group in R ⁵¹ to R ⁵⁸ and R ⁶⁰ to R ⁷⁵ is preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group. Examples of the substituent of the alkyl group include a halo group, a hydroxyl group, a cyano group, and a -CONH ₂ group.

Representative examples of chromophores represented by the formulas (6-1) to (6-6) include chromophores represented by the following compound group d or compound group e.

[Compound group d]

[Compound group e]

The diaryl chromophore is preferably represented by the following formula (7-1) or (7-2), more preferably represented by the following formula (7-2).

[In the formulas (7-1) and (7-2)

R ⁸¹ , R ⁸² , R ⁸³ , R ⁸⁴ , R ⁸⁶ , R ⁸⁷ , R ⁸⁸ and R ⁸⁹ independently represent an alkyl group having 1 to 6 carbon atoms,

R ⁸⁵ , R ⁹⁰ and R ⁹¹ independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms]

The alkyl group in R ⁸¹ to R ⁹¹ is preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group.

Representative examples of chromophores represented by the formulas (7-1) to (7-2) include chromophores represented by the following group of compounds f.

[Compound group f]

The quinone imine chromophore is preferably represented by the following formulas (8-1) to (8-3), more preferably represented by the following formula (8-1) or (8-3).

[In the formulas (8-1) to (8-3)

R ¹⁰¹ , R ¹⁰² , R ¹⁰³ , R ¹⁰⁴ , R ¹⁰⁵ , R ¹⁰⁶ , R ¹⁰⁸ , R ¹⁰⁹ , R ¹¹⁰ , R ¹¹¹ , R ¹¹⁴ , R ¹¹⁵ , R ¹¹⁶ , R ¹¹⁷ and R ¹¹⁸ independently represent a hydrogen atom , A substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, a phenyl group or a benzyl group,

R ¹⁰⁷ and R ¹¹³ independently represent an alkyl group having 1 to 6 carbon atoms or an aryl group having 6 to 20 carbon atoms,

R ¹¹² represents -NR ¹¹⁹ R ¹²⁰ (R ¹¹⁹ and R ¹²⁰ independently represent a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms), a hydroxyl group, a nitro group or a cyano group,

And Q represents an oxygen atom or a sulfur atom.

The alkyl group in R ¹⁰¹ to R ¹¹¹ and R ¹¹³ to R ¹²⁰ is preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or an ethyl group. Examples of the substituent of the alkyl group include a halo group, a hydroxyl group and a cyano group. As the aryl group having 6 to 20 carbon atoms in R ¹⁰⁷ and R ¹¹³ , a phenyl group is preferable.

Representative examples of chromophores represented by the formulas (8-1) to (8-3) include, for example, chromophores shown in the following group of compounds g.

[Compound group g]

The anthraquinone chromophore is preferably represented by the following formula (9-1) or (9-2), more preferably represented by the following formula (9-1).

[In formulas (9-1) and (9-2)

R ¹³¹ , R ¹³⁵ and R ¹³⁶ independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted or unsubstituted phenyl group,

R ¹³² , R ¹³³ , R ¹³⁴ , R ¹³⁸ , R ¹³⁹ and R ¹⁴⁰ independently represent an alkyl group having 1 to 6 carbon atoms, and R ¹³⁷ denotes a methylene group or a substituted or unsubstituted alkylene group.

The alkyl group in R ¹³¹ to R ¹³⁶ and R ¹³⁸ to R ¹⁴⁰ is preferably an alkyl group having 1 to 4 carbon atoms, more preferably a methyl group or ethyl group. Examples of the substituent of the alkyl group include a halo group, a hydroxyl group and a cyano group. Examples of the substituent of the phenyl group include an alkyl group having 1 to 6 carbon atoms, a halo group, a hydroxyl group and a cyano group.

The alkylene group is preferably an alkylene group having 2 to 4 carbon atoms such as an ethylene group, a trimethylene group, a propylene group and a tetramethylene group. As the substituent of the alkylene group, a hydroxyl group, a cyano group or a nitro group can be exemplified .

Representative examples of chromophores represented by the above chemical formulas (9-1) or (9-2) include chromophores represented by the following group of compounds h.

[Compound group h]

The phthalocyanine chromophore is preferably represented by the following chemical formula (10).

In the formula (10)

CuPc represents a copper phthalocyanine residue,

T represents a group represented by the following formula (10a) or (10b)

[In the formulas (10a) and (10b)

R ¹⁵¹ , R ¹⁵² , R ¹⁵³ , R ¹⁵⁴ , R ¹⁵⁵ , R ¹⁵⁶ , R ¹⁵⁷ and R ¹⁵⁸ independently represent a hydrogen atom, an alkyl group having 1 to 6 carbon atoms or a phenyl group,

p ¹ independently represents an integer of 2 to 8,

and mb independently represent an integer of 1 to 5)

Representative examples of chromophores represented by the above formula (10) include, for example, chromophores represented by the following group of compounds k.

[Compound group k]

As the xanthene-based chromophore, it is preferable to be represented by the following chemical formula (11).

[In the formula (11)

R ¹⁷¹ , R ¹⁷² , R ¹⁷³ and R ¹⁷⁴ independently represent a hydrogen atom, -R ¹⁷⁸ or an aromatic hydrocarbon group having 6 to 10 carbon atoms, provided that the hydrogen atom contained in the aromatic hydrocarbon group is a halogen atom, -R ¹⁷⁸ , OH, -OR ¹⁷⁸ , -SO ₃ H, -SO ₃ M, -CO ₂ H, -CO ₂ R ¹⁷⁸ , -SO ₃ R ¹⁷⁸ , -SO ₂ NHR ¹⁷⁹ or -SO ₂ NR ¹⁷⁹ R ¹⁸⁰ Lt; / RTI &gt;

R ¹⁷⁵ and R ¹⁷⁶ independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms;

R ¹⁷⁷ represents -SO ₃ H, -SO ₃ M, -CO ₂ H, -CO ₂ R ¹⁷⁸ , -SO ₃ R ¹⁷⁸ , -SO ₂ NHR ¹⁷⁹ or -SO ₂ NR ¹⁷⁹ R ¹⁸⁰ ;

k represents an integer of 0 to 5, and when k is an integer of 2 or more, a plurality of R ¹⁷⁷ may be the same or different;

R ¹⁷⁸ is a saturated hydrocarbon group having 1 to 10 carbon atoms (provided that the hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom, and the methylene group contained in the saturated hydrocarbon group is substituted with an oxygen atom, a carbonyl group or -NR ¹⁷⁸ - Lt; / RTI &gt;

R ¹⁷⁹ and R ¹⁸⁰ independently represent a linear alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms or -Z, or a substituent having 1 to 10 carbon atoms formed by bonding R ¹⁷⁹ and R ¹⁸⁰ together Or an unsubstituted heterocyclic group, provided that the hydrogen atoms contained in the alkyl group and the cycloalkyl group may be substituted with a hydroxyl group, a halogen atom, -Z, -CH = CH ₂ or -CH = CHR ¹⁷⁸ , And the methylene group contained in the cycloalkyl group may be substituted with an oxygen atom, a carbonyl group or -NR ¹⁷⁸ -, and the hydrogen atom contained in the heterocyclic group may be substituted with -R ¹⁷⁸ , -OH or -Z;

M represents a sodium atom or a potassium atom;

Z represents an aromatic hydrocarbon group having 6 to 10 carbon atoms or an aromatic heterocyclic group having 5 to 10 carbon atoms, provided that the hydrogen atom contained in the aromatic hydrocarbon group and the aromatic heterocyclic group is -OH, R ¹⁷⁸ , -OR ¹⁷⁸ , -NO ₂ , -CH = CH ₂ , -CH = CHR ^178, or may be substituted with a halogen atom)

The saturated hydrocarbon group represented by R ¹⁷⁸ may be any of linear, branched and cyclic, and may have a crosslinked structure when the number of carbon atoms is 1 to 10. Specific examples include a nonyl group, a decanyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group and a tricyclodecanyl group in addition to the same alkyl group as R ⁴ in the above formula (2-1) . Examples of the group in which a methylene group contained in a saturated hydrocarbon group is substituted with an oxygen atom include a methoxypropyl group, an ethoxypropyl group, a 2-ethylhexyloxypropyl group, and a methoxyhexyl group.

Examples of the substituted or unsubstituted heterocyclic group having 1 to 10 carbon atoms formed by bonding R ¹⁷⁹ and R ¹⁸⁰ together include pyrrole, pyridine, indole, isoindole, quinoline, isoquinoline, carbazole, phenanthridine, Furan, pyran, isobenzofuran, isochromene, xanthene, thiophene, thianthrene, phenoxathiin, phenothiazine, and the like. Examples of the substituent in the heterocyclic group include a halo group, a hydroxyl group, an alkoxy group, an amino group, and an alkyl group. Examples of the aromatic heterocyclic group having 5 to 10 carbon atoms in Z include furyl, thienyl, pyridyl, pyrrolyl, oxazolyl, isoxazole, thiazolyl, isothiazolyl, Group, a pyrimidyl group, and the like.

Examples of the aromatic hydrocarbon group for R ¹⁷¹ , R ¹⁷² , R ¹⁷³ , R ¹⁷⁴ and Z include a phenyl group and a naphthyl group.

Examples of -SO ₃ R ¹⁷⁸ in R ¹⁷¹ , R ¹⁷² , R ¹⁷³ , R ¹⁷⁴ and R ¹⁷⁷ include a methanesulfonyl group, an ethanesulfonyl group, a hexanesulfonyl group and a decanesulfonyl group. Examples of -CO ₂ R ¹⁷⁸ include a methyloxycarbonyl group, an ethyloxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a butyloxycarbonyl group, a cyclohexyloxycarbonyl group, and a methoxypropyloxycarbonyl group. ^{_{Also, -SO 2 NHR 179, -SO 2}} NR 179 R R 179 in ^180, R ¹⁸⁰ as, an alkyl group having a carbon number of the branched chain of 6 to 8, an alicyclic hydrocarbon having 5 to 7 carbon atoms, allyl, having 8 to A hydroxyl group-containing alkyl group having 2 to 8 carbon atoms, an alkoxy group-containing alkyl group having 2 to 8 carbon atoms, and an aryl group are preferable.

R ¹⁷¹ , R ¹⁷² , R ¹⁷³ and R ¹⁷⁴ are preferably an alkyl group having 1 to 6 carbon atoms, more preferably an alkyl group having 1 to 4 carbon atoms, and still more preferably a methyl group or an ethyl group.

As R ¹⁷⁵ and R ¹⁷⁶ , a hydrogen atom or an alkyl group having 1 to 6 carbon atoms is preferable, the number of carbon atoms in the alkyl group is more preferably 1 to 4, and a methyl group or an ethyl group is more preferable.

R ¹⁷⁷ is preferably -SO ₃ H, -SO ₃ M, -CO ₂ H or -CO ₂ R ¹⁷⁸ , more preferably -CO ₂ H or -CO ₂ R ¹⁷⁸ . -CO ₂ R ¹⁷⁸ in the R ¹⁷⁸ is preferably an alkyl group having 1 to 6 carbon atoms, and is the number of carbon atoms is 1 to 4, more preferably an alkyl group, more preferably a methyl group or an ethyl group.

k is preferably 1 or 2, and more preferably 1.

Representative examples of the cation represented by the above formula (11) include, for example, a cation represented by the following formula.

Among them, from the viewpoint of heat resistance, Z ^{+ is preferably a} triarylmethane type cationic chromophore represented by the formula (2-1), a triarylmethane type cationic chromophore represented by the formula (2-2), a methine type cation A cationic chromophore of azo type, a cationic chromophore of diarylmethane type, a cationic chromophore of quinone imine type, and a cationic chromophore of xanthine type are preferable, and a triarylmethane type , A cationic chromophore of formula (2-2), a triarylmethane type cationic chromophore, a methine type cationic chromophore, and a xanthene type cationic chromophore are more preferable.

The reason why the heat resistance is different depending on the type and structure of the chromophore is not clear. The present inventors believe that a chromophore having a resonance structure interacts with a structural unit represented by the formula (1), and therefore, is easily stabilized and has a high heat resistance.

The present colorant may have a structural unit other than the structural unit represented by the formula (1) (hereinafter also referred to as "another structural unit"), and examples of such a structural unit include ethylene (Meth) acrylate, a structural unit derived from a (meth) acrylic acid ester, a structural unit derived from a vinyl ether, a structural unit derived from a And a structural unit derived from a macromonomer having a mono (meth) acryloyl group at the terminal of the molecular chain.

Examples of the structural unit derived from the ethylenic unsaturated monomer having at least one carboxyl group include (meth) acrylic acid, maleic acid, maleic anhydride, mono [2- (meth) acryloyloxyethyl] Carboxypolycaprolactone mono (meth) acrylate, p-vinylbenzoic acid, and the like.

Further, the structural unit derived from the N-substituted maleimide can be obtained, for example, by N-substituted maleimide such as N-phenylmaleimide or N-cyclohexylmaleimide.

The aromatic vinyl compound may be an aromatic vinyl compound such as styrene,? -Methylstyrene, p-hydroxystyrene, p-hydroxy-? -Methylstyrene, p-vinylbenzylglycidylether and acenaphthylene Lt; / RTI &gt;

Examples of the structural unit derived from the (meth) acrylic acid ester include methyl (meth) acrylate, n-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, (Meth) acrylate, benzyl (meth) acrylate, polyethylene glycol (polymerization degree 2 to 10) methyl ether (meth) acrylate, polypropylene glycol (polymerization degree 2 to 10) (Meth) acrylate, isobornyl (meth) acrylate, triethyleneglycol (meth) acrylate, triethyleneglycol (meth) acrylate, cyclo [5.2.1.0 ^2,6] decane-8-yl (meth) acrylate, dicyclopentenyl (meth) acrylate, glycerol mono (meth) acrylate, 4-hydroxyphenyl (meth) acrylate, para Ethylene oxide of cumylphenol (Meth) acrylate, 3 - [(meth) acryloyloxymethyl] oxetane, 3 - [(meth) acrylate, (Meth) acryloyloxymethyl] -3-ethyl oxetane.

The structural unit derived from vinyl ether is, for example, cyclohexyl vinyl ether, isobornyl vinyl ether, tricyclo [5.2.1.0 ^2,6 ] decan-8-yl vinyl ether, pentacyclo pentadecanyl vinyl ether , Vinyl ethers such as 3- (vinyloxymethyl) -3-ethyloxetane.

Examples of the structural unit derived from a macromonomer having a mono (meth) acryloyl group at the terminal of the polymer molecular chain include polystyrene, polymethyl (meth) acrylate, poly-n-butyl (meth) Can be obtained by a macromonomer having a mono (meth) acryloyl group at the end of a polymer molecular chain such as a polysiloxane.

Among them, from the viewpoint of dispersibility, the present colorant preferably has a structural unit derived from a (meth) acrylic acid ester as another structural unit, and more preferably a structural unit derived from a (meth) acrylic acid alkyl ester.

When the present colorant has another structural unit, the copolymerization ratio of the other structural units is preferably the following in terms of dispersibility.

That is, the ratio p of the structural unit represented by the formula (1) and the ratio r of the other structural units in the total structural units of the present colorant are preferably in a ratio of p / r = 1 / 0.5 to 1/19, more preferably r = 1 / 1.5 to 1/9, and more preferably p / r = 1/2 to 1/7.

The colorant has a weight average molecular weight (Mw) in terms of polystyrene measured by gel permeation chromatography (hereinafter abbreviated as GPC) (elution solvent: tetrahydrofuran), usually 1,000 to 100,000, preferably 3,000 to 50,000. By adopting this form, heat resistance, film properties, electrical characteristics, pattern shape, and resolution can be improved.

The ratio (Mw / Mn) of the weight average molecular weight (Mw) to the number average molecular weight (Mn) of the present colorant in the present invention is preferably 1.0 to 5.0, more preferably 1.0 to 3.0. Herein, Mn is the number average molecular weight in terms of polystyrene measured by GPC (elution solvent: tetrahydrofuran).

This colorant can be produced by a known method, and can be produced, for example, by the same method as in the embodiment of Japanese Patent Application Laid-Open No. 194466/1989. The present colorant thus obtained is soluble in various organic solvents including propylene glycol monomethyl ether acetate and the like, and has excellent solvent resistance.

The colorants used in the present invention may be used alone or in combination of two or more.

The coloring composition of the present invention may further contain (A) another coloring agent as a coloring agent. In this case, the content of the present colorant is preferably 0.1 to 99% by mass, more preferably 1 to 80% by mass, still more preferably 10 to 70% by mass, and particularly preferably 20 to 60% by mass %to be.

No particular limitation is imposed on the other colorants, and the color and the material can be appropriately selected according to the application. Any of pigments, dyes and natural pigments other than the present colorant can be used, but in the sense of obtaining pixels with high luminance and color purity Organic pigments and organic dyes are preferable, and organic pigments are more preferable.

Examples of the organic pigments include pigments classified by the color index (CI) (published by The Society of Dyers and Colourists), and among them, JP-A-2001-081348, JP-A- JP-A-2010-026334, JP-A-2010-191304, JP-A-2010-237384, JP-A-2010-237569, JP-A-2011-006602, JP- CI Pigment Red 166, CI Pigment Red 177, CI Pigment Red 224, CI Pigment Red 242, CI Pigment Red 254, CI Pigment Green 7, CI Pigment Green 36, CI Pigment Green 58, CI Pigment Blue 15: 6, CI Pigment Blue 80, CI Pigment Yellow 83, CI Pigment Yellow 138, CI Pigment Yellow 139, CI Pigment Yellow 150, Yellow 180, the organic pigment other than the lake pigments such as C.I. Pigment Yellow 211, C.I. Pigment Orange 38, C.I. Pigment Violet 23 is preferred. Among the lake pigments, triarylmethane lake pigments, xanthene lake pigments and azo lake pigments are preferable, and triarylmethane lake pigments and xanthane lake pigments are more preferable.

When a pigment is used as another colorant in the present invention, the pigment may be purified and used by recrystallization, reprecipitation, solvent cleaning, sublimation, vacuum heating, or a combination thereof. Further, the pigment may be used by modifying its particle surface with a resin as necessary. As the resin for modifying the particle surface of the pigment, for example, a vehicle resin described in Japanese Patent Application Laid-Open No. 2001-108817 or a commercially available resin for dispersing various pigments may be mentioned. Examples of the resin coating method for the carbon black surface include a method described in Japanese Patent Application Laid-Open No. 9-71733, Japanese Patent Application Laid-Open No. 9-95625, Japanese Patent Application Laid-Open No. 9-124969 Can be adopted. Further, the organic pigment may be used by finely grinding primary particles by so-called salt milling. As a method of the salt milling, for example, a method disclosed in Japanese Unexamined Patent Application Publication No. 08-179111 can be adopted.

When a pigment is used as another colorant in the present invention, known dispersants and dispersion aids may be further contained. Examples of the known dispersant include urethane-based dispersants, polyethyleneimine-based dispersants, polyoxyethylene alkyl ether-based dispersants, polyoxyethylene alkyl phenyl ether-based dispersants, polyethylene glycol diester dispersants, sorbitan fatty acid ester- A dispersant, and an acrylic dispersant, and as a dispersing aid, a pigment derivative and the like.

Dispersing agents such as Disperbyk-2000, Disperbyk-2001, BYK-LPN6919, BYK-LPN21116 and BYK-LPN21324 (manufactured by BYK), as urethane dispersants, are commercially available as commercially available products, Disperbyk-161, Disperbyk-162, Disperbyk-165, Disperbyk-167, Disperbyk-170, Disperbyk-182, Disperbyk-2164 (manufactured by BYK), Solpus 76500 (Manufactured by Mitsui Chemicals, Inc.), Solsperse 24000 (manufactured by Lubrizol Corporation) as a polyethyleneimine-based dispersant, and Ajisper PB821, Ajisper PB822, Ajisper PB880 and Ajisper PB881 (Manufactured by Nippon Steel Chemical Co., Ltd.).

Specific examples of the pigment derivative include copper phthalocyanine, diketopyrrolopyrrole, and sulfonic acid derivatives of quinophthalone.

In the present invention, the other colorants may be used alone or in combination of two or more.

The content ratio of the (A) coloring agent is usually in the range of from 0.1 to 10 parts by weight, more preferably from 0.1 to 10 parts by weight, based on the solid content of the coloring composition, from the viewpoint of forming a black matrix and a black spacer having excellent heat resistance and solvent resistance, Is 5 to 70% by mass, preferably 5 to 60% by mass. Here, the solid content is a component other than the solvent described later.

- (B) Binder Resin -

The coloring composition of the present invention may contain a binder resin (excluding a polymer having a structural unit represented by the above formula (1)). This makes it possible to improve the alkali solubility of the coloring composition, the adhesion to the substrate, the storage stability, and the like. As the binder resin, a resin having an acidic functional group such as a carboxyl group and a phenolic hydroxyl group is preferable, as long as it does not correspond to a polymer containing the structural unit represented by the above formula (1). Among them, a polymer having a carboxyl group (hereinafter referred to as a "carboxyl group-containing polymer") is preferable, and for example, an ethylenically unsaturated monomer having at least one carboxyl group (hereinafter referred to as "unsaturated monomer (b1) (Hereinafter referred to as &quot; unsaturated monomer (b2) &quot;).

Examples of the unsaturated monomer (b1) include the same as the ethylenically unsaturated monomer having a carboxyl group. The unsaturated monomers (b1) may be used alone or in admixture of two or more.

Examples of the unsaturated monomer (b2) include N-substituted maleimide, aromatic vinyl compound, (meth) acrylate, vinyl ether, macromonomer having a mono (meth) acryloyl group at the end of the polymer molecular chain And specific examples thereof include the same ones as described above. The unsaturated monomers (b2) may be used alone or in combination of two or more.

The copolymerization ratio of the unsaturated monomer (b1) in the copolymer of the unsaturated monomer (b1) and the unsaturated monomer (b2) is preferably from 5 to 50 mass%, more preferably from 10 to 40 mass%. By copolymerizing the unsaturated monomer (b1) in such a range, a colored composition excellent in alkali developability and storage stability can be obtained.

As specific examples of the copolymer of the unsaturated monomer (b1) and the unsaturated monomer (b2), for example, JP-A-7-140654, JP-A-8-259876, Japanese Patent Laid-Open Nos. 10-31308, 10-300922, 11-174224, 11-258415, 2000-56118 And Japanese Patent Application Laid-Open No. 2004-101728.

Further, in the present invention, for example, Japanese Patent Application Laid-Open No. 5-19467, Japanese Patent Application Laid-Open No. 6-230212, Japanese Patent Application Laid-Open No. 7-207211, (Meth) acryloyl group and the like as a side chain, as disclosed in JP-A-09-325494, JP-A-11-140144 and JP-A-2008-181095 Containing polymer may be used as a binder resin.

The binder resin in the present invention has a weight average molecular weight (Mw) in terms of polystyrene measured by gel permeation chromatography (hereinafter abbreviated as GPC) (elution solvent: tetrahydrofuran) of usually 1,000 to 100,000, 50,000. By adopting this form, heat resistance, film properties, electrical characteristics, pattern shape, and resolution can be improved.

The ratio (Mw / Mn) of the weight average molecular weight (Mw) to the number average molecular weight (Mn) of the binder resin in the present invention is preferably 1.0 to 5.0, more preferably 1.0 to 3.0. Herein, Mn is the number average molecular weight in terms of polystyrene measured by GPC (elution solvent: tetrahydrofuran).

The binder resin in the present invention can be prepared by a known method, for example, Japanese Patent Application Laid-Open No. 2003-222717, Japanese Patent Application Laid-Open No. 2006-259680, International Publication No. 07/029871 The structure thereof, Mw and Mw / Mn can be controlled.

In the present invention, the binder resins may be used alone or in combination of two or more.

The content of the binder resin in the present invention is usually 10 to 1,000 parts by mass, preferably 20 to 500 parts by mass, more preferably 50 to 350 parts by mass, and still more preferably 100 to 250 parts by mass, relative to 100 parts by mass of (A) Mass part. By adopting such a form, heat resistance, solvent resistance, alkali developability, storage stability of the colored composition, and chromaticity characteristics can be improved. Also, it is possible to suppress the transferring property.

- (C) Polymerizable compound -

The polymerizable compound in the present invention refers to a compound having two or more polymerizable groups. Examples of the polymerizable group include an ethylenic unsaturated group, an oxiranyl group, an oxetanyl group, and an N-alkoxymethylamino group. As the polymerizable compound in the present invention, a compound having two or more (meth) acryloyl groups or a compound having two or more N-alkoxymethylamino groups is preferable.

Specific examples of the compound having two or more (meth) acryloyl groups include polyfunctional (meth) acrylates obtained by reacting an aliphatic polyhydroxy compound with (meth) acrylic acid, polyfunctional (meth) acrylates modified with caprolactone, A polyfunctional urethane (meth) acrylate obtained by reacting a (meth) acrylate modified with an alkylene oxide and a polyfunctional (meth) acrylate having a hydroxyl group with a polyfunctional isocyanate, a (meth) acrylate having a hydroxyl group and an acid anhydride And a polyfunctional (meth) acrylate having a carboxyl group obtained by the reaction.

Examples of the aliphatic polyhydroxy compound include divalent aliphatic polyhydroxy compounds such as ethylene glycol, propylene glycol, polyethylene glycol and polypropylene glycol; And tri- or higher aliphatic polyhydroxy compounds such as glycerin, trimethylol propane, pentaerythritol and dipentaerythritol. Examples of the (meth) acrylate having a hydroxyl group include 2-hydroxyethyl (meth) acrylate, trimethylolpropane di (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta (Meth) acrylate, and glycerol dimethacrylate. Examples of the polyfunctional isocyanate include tolylene diisocyanate, hexamethylene diisocyanate, diphenylmethylene diisocyanate, and isophorone diisocyanate. Examples of the acid anhydride include anhydrides of dibasic acids such as succinic anhydride, maleic anhydride, anhydrous glutaric acid, itaconic anhydride, phthalic anhydride, and hexahydrophthalic anhydride, anhydrous pyromellitic acid, biphenyltetracarboxylic acid 2 An anhydride, and a tetrabasic acid dianhydride such as benzophenone tetracarboxylic acid dianhydride.

Examples of the caprolactone-modified polyfunctional (meth) acrylate include compounds described in paragraphs [0015] to [0018] of JP-A No. 11-44955. Examples of the alkylene oxide-modified polyfunctional (meth) acrylate include bisphenol A di (meth) acrylate modified with at least one selected from ethylene oxide and propylene oxide, ethylene oxide and propylene oxide Trimethylolpropane tri (meth) acrylate modified with at least one member selected from the group consisting of isocyanuric acid tri (meth) acrylate modified with at least one member selected from the group consisting of ethylene oxide and propylene oxide, Pentaerythritol tri (meth) acrylate modified with at least one member selected from propylene oxide, pentaerythritol tetra (meth) acrylate modified with at least one member selected from ethylene oxide and propylene oxide, Dipentaerythritol penta (meth) acrylate modified with at least one member selected from ethylene oxide and propylene oxide Agent) acrylate, ethylene oxide and propylene oxide at least one member of dipentaerythritol hexa (meth modified by selected from) acrylate and the like.

Examples of the compound having two or more N-alkoxymethylamino groups include compounds having a melamine structure, a benzoguanamine structure, and a urea structure. Also, the melamine structure and the benzoguanamine structure refer to a chemical structure having one or more triazine rings or phenyl-substituted triazine rings as basic skeletons, and also include melamine, benzoguanamine, or condensates thereof. Specific examples of the compound having two or more N-alkoxymethylamino groups include N, N, N ', N', N '', N '' - hexa (alkoxymethyl) Tetra (alkoxymethyl) benzoguanamine, N, N, N ', N'-tetra (alkoxymethyl) glycoluril and the like.

Of these polymerizable compounds, polyfunctional (meth) acrylates obtained by reacting tri- or higher-valent aliphatic polyhydroxy compounds with (meth) acrylic acid, caprolactone-modified polyfunctional (meth) acrylates, polyfunctional urethane (meth) (Meth) acrylate having a carboxyl group, N, N, N ', N', N '', N '' - hexa (alkoxymethyl) Alkoxymethyl) benzoguanamine is preferable. Among the multifunctional (meth) acrylates obtained by reacting a trivalent or higher aliphatic polyhydroxy compound with (meth) acrylic acid, trimethylolpropane triacrylate, pentaerythritol triacrylate, dipentaerythritol pentaacrylate, Among the polyfunctional (meth) acrylates having a carboxyl group, a compound obtained by reacting pentaerythritol triacrylate with succinic anhydride, a compound obtained by reacting dipentaerythritol pentaacrylate with succinic anhydride, The strength of the colored layer is high and the surface smoothness of the colored layer is excellent and background contamination and film residue are hardly generated on the substrate of the unexposed portion and on the light shielding layer. Further, heat resistance and solvent resistance can be improved, and the flame retardancy can be suppressed.

In the present invention, the polymerizable compound (C) may be used alone or in admixture of two or more.

The content of the polymerizable compound (C) in the present invention is preferably 10 to 1,000 parts by mass, more preferably 20 to 700 parts by mass, further preferably 100 to 500 parts by mass, particularly preferably 200 to 400 parts by mass, relative to 100 parts by mass of the (A) desirable. By adopting this form, heat resistance, solvent resistance, curability, and alkali developability can be improved. In addition, it is also possible to inhibit migration.

- Photopolymerization initiator -

The coloring composition of the present invention may contain a photopolymerization initiator. Thus, the coloring composition can be imparted with radiation sensitivity. The photopolymerization initiator used in the present invention is a compound which generates active species capable of initiating polymerization of the polymerizable compound by exposure to radiation such as visible light, ultraviolet light, deep ultraviolet light, electron beam, and X-ray.

Examples of such photopolymerization initiators include thioxanthone compounds, acetophenone compounds, nonimidazole compounds, triazine compounds, O-acyloxime compounds, onium salt compounds, benzoin compounds, benzophenone compounds, -Diketone compounds, polynuclear quinone compounds, diazo compounds, imidosulfonate compounds and the like.

In the present invention, the photopolymerization initiator may be used alone or in admixture of two or more. The photopolymerization initiator is preferably at least one selected from the group consisting of a thioxanthone compound, an acetophenone compound, a nonimidazole compound, a triazine compound, and an O-acyloxime compound.

Specific examples of the thioxanone compound in the photopolymerization initiator of the present invention include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone , 2,4-dichlorothioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone and 2,4-diisopropylthioxanthone.

Specific examples of the acetophenone-based compound include 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane- 1- (4-morpholinophenyl) butan-1-one and 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinophenyl) butan-1-one.

Specific examples of the imidazole-based compound include 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole, 2,2'- Bis (2,4-dichlorophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis (2,4,6-trichlorophenyl ) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole and the like.

When a non-imidazole-based compound is used as a photopolymerization initiator, it is preferable to use a hydrogen donor in combination because the sensitivity can be improved. The term "hydrogen donor" as used herein means a compound capable of providing a hydrogen atom to a radical generated from a non-imidazole-based compound by exposure. Examples of the hydrogen donor include mercaptan-based hydrogen donors such as 2-mercaptobenzothiazole and 2-mercaptobenzoxazole, 4,4'-bis (dimethylamino) benzophenone, 4,4'- Ethylamino) benzophenone, and the like. In the present invention, the hydrogen donors may be used alone or in admixture of two or more. The use of a combination of at least one mercaptan-based hydrogen donor and at least one amine-based hydrogen donor is preferable because the sensitivity can be further improved Do.

Specific examples of the triazine-based compound include 2,4,6-tris (trichloromethyl) -s-triazine, 2-methyl-4,6-bis (trichloromethyl) (Trichloromethyl) -s-triazine, 2- [2- (furan-2-yl) ethenyl] -4 (Trichloromethyl) -s-triazine, 2- [2- (4-diethylamino-2-methylphenyl) ethenyl] -4,6-bis (Trichloromethyl) -s-triazine, 2- (4-methoxyphenyl) ethenyl] -4,6-bis (Trichloromethyl) -s-triazine, 2- (4-n-butoxyphenyl) - And triazine-based compounds having a halomethyl group such as 4,6-bis (trichloromethyl) -s-triazine.

Specific examples of the O-acyloxime-based compound include 1,2-octanedione, 1- [4- (phenylthio) phenyl] -, 2- (O-benzoyloxime), ethanone, 1- [ (2-methylbenzoyl) -9H-carbazol-3-yl] -, 1- (O- -9H-carbazol-3-yl] -, 1- (O-acetyloxime), ethanone, 1- [ -Dimethyl-1,3-dioxolanyl) methoxybenzoyl} -9H-carbazol-3-yl] -, 1- (O-acetyloxime). As commercially available products of O-acyloxime compounds, NCI-831 and NCI-930 (manufactured by ADEKA K.K.) may be used.

In the present invention, when a photopolymerization initiator other than a non-imidazole-based compound such as an acetophenone-based compound is used, a sensitizer may be used in combination. Examples of such sensitizers include 4,4'-bis (dimethylamino) benzophenone, 4,4'-bis (diethylamino) benzophenone, 4-diethylaminoacetophenone, 4-dimethylaminopropiophenone , Ethyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2,5-bis (4-diethylaminobenzal) cyclohexanone, 7-diethylamino- ) Coumarin, and 4- (diethylamino) chalcone.

In the present invention, the content of the photopolymerization initiator is preferably 0.01 to 120 parts by mass, particularly preferably 1 to 100 parts by mass, per 100 parts by mass of the (C) polymerizable compound. By adopting this form, heat resistance, solvent resistance, curability, and film properties can be improved. In addition, it is also possible to inhibit migration.

-menstruum-

The coloring composition of the present invention contains the above components (A) and (C), and optionally other components, which are usually formulated as a liquid composition by blending a solvent.

As the solvent, any of the components (A) and (C) and other components constituting the coloring composition may be appropriately selected and used as long as they have a suitable volatility without dispersing or dissolving the components and not reacting with these components.

Of these solvents, for example,

Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono- -Propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono- Dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl ether, tri (Poly) alkylene glycol monoalkyl ethers such as propylene glycol monoethyl ether;

Lactic acid alkyl esters such as methyl lactate and ethyl lactate;

(Cyclo) alkyl alcohols such as methanol, ethanol, propanol, butanol, isopropanol, isobutanol, t-butanol, octanol, 2-ethylhexanol and cyclohexanol;

Ketoalcohols such as diacetone alcohol;

Ethylene glycol monomethyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, dipropylene glycol monomethyl ether (Poly) alkylene glycol monoalkyl ether acetates such as acetate, 3-methoxybutyl acetate and 3-methyl-3-methoxybutyl acetate;

Other ethers such as diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether and tetrahydrofuran;

Ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone and 3-heptanone;

Diacetates such as propylene glycol diacetate, 1,3-butylene glycol diacetate, and 1,6-hexanediol diacetate;

Alkoxycarboxylates such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate and 3-methyl- Acid esters;

Amyl acetate, n-butyl acetate, ethyl butyrate, n-propyl butyrate, i-propyl butyrate, propyl acetate, isopropyl acetate, n- , N-butyl butyrate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetoacetate, ethyl acetoacetate and ethyl 2-oxobutanoate;

Aromatic hydrocarbons such as toluene and xylene;

Amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone, or lactams

And the like.

Of these solvents, propylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, 3 -Methoxybutyl acetate, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, cyclohexanone, 2-heptanone, 3-heptanone, 1,3-butylene glycol diacetate, 1,6-hexanediol di Acetate, ethyl lactate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, 3-methyl-3-methoxybutyl propionate, n-butyl acetate, amyl acetate, i-amyl acetate, n-butyl propionate, ethyl butyrate, i-propyl butyrate, n-butyl butyrate and ethyl pyruvate.

In the present invention, the solvents may be used alone or in admixture of two or more.

Although the content of the solvent is not particularly limited, the total amount of each component excluding the solvent of the coloring composition is preferably 5 to 50 mass%, more preferably 10 to 40 mass%. By using this form, it is possible to obtain a colorant dispersion having good dispersibility and stability, and a coloring composition having good applicability and stability.

-additive-

The coloring composition of the present invention may contain various additives as required.

Examples of the additive include fillers such as glass and alumina; High molecular compounds such as polyvinyl alcohol and poly (fluoroalkyl acrylate); Surfactants such as fluorine-based surfactants and silicone-based surfactants; Vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) Aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxycyclo Hexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane and the like Adhesion promoters; Antioxidants such as 2,2-thiobis (4-methyl-6-t-butylphenol) and 2,6-di-t-butylphenol; Ultraviolet absorbers such as 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chlorobenzotriazole and alkoxybenzophenones; An anti-aggregation agent such as sodium polyacrylate; Amino-1-pentanol, 3-amino-1,2-propane, 3-amino-1-pentanol, Diol, 2-amino-1,3-propanediol, 4-amino-1,2-butanediol and the like; A developing agent such as mono [2- (meth) acryloyloxyethyl succinic acid], phthalic acid mono [2- (meth) acryloyloxyethyl], omega -carboxylic polycaprolactone mono (meth) .

coloring Curing membrane  And a method for forming the same

The colored cured film of the present invention is formed using the coloring composition of the present invention, and specifically means a color pixel, a black matrix, a black spacer, etc. used for a display element or a solid-state image pickup element.

Hereinafter, a colored cured film used for a color filter constituting a display element or a solid-state image pickup element and a method for forming the colored cured film will be described.

As a method of manufacturing a color filter, first, the following method can be mentioned. First, a light-shielding layer (black matrix) is formed on the surface of the substrate so as to partition a portion for forming a pixel as needed. Subsequently, a blue liquid composition of the radiation sensitive coloring composition of the present invention, for example, is coated on the substrate, and then the substrate is prebaked to evaporate the solvent to form a coating film. Subsequently, this coating film is exposed through a photomask, and then developed with an alkali developing solution to dissolve and remove the unexposed portion of the coating film. Thereafter, by post-baking, a pixel array in which a blue pixel pattern (colored cured film) is arranged in a predetermined arrangement is formed.

Subsequently, each of the radiation-sensitive coloring compositions of green or red was used, and each of the radiation-sensitive coloring compositions was applied, prebaked, exposed, developed, and postbaked in the same manner as above to form a green pixel array and a red pixel Arrays are sequentially formed on the same substrate. Thereby, a color filter in which pixel arrays of three primary colors of blue, green, and red are arranged on a substrate is obtained. However, in the present invention, the order of forming the pixels of each color is not limited to the above.

The black matrix can be formed by forming a metal thin film of chromium or the like formed by sputtering or vapor deposition into a desired pattern using a photolithography method. By using a radiation-sensitive coloring composition in which a black coloring agent is dispersed, May be formed in the same manner as in the case of FIG.

Examples of the substrate used for forming the color filter include glass, silicon, 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, vacuum deposition or the like depending on the purpose.

When the radiation sensitive coloring composition is applied to a substrate, a suitable coating method such as a spraying method, a roll coating method, a rotation coating method (spin coating method), a slit die coating method (slit coating method) In particular, it is preferable to employ a spin coating method or a slit die coating method.

Prebaking is usually carried out in combination with reduced pressure drying and heat drying. The reduced-pressure drying is usually carried out until 50 to 200 Pa is reached. The conditions for heating and drying are usually about 70 to 110 DEG C for about 1 to 10 minutes.

The coating thickness is usually 0.6 to 8 占 퐉, preferably 1.2 to 5 占 퐉, as a film thickness after drying.

Examples of the light source of radiation used when forming at least one kind selected from the pixels and the black matrix include a halogen lamp, a halogen lamp, a tungsten lamp, a high pressure mercury lamp, an ultra high pressure mercury lamp, a metal halide lamp, a medium pressure mercury lamp, A lamp light source, and a laser light source such as an argon ion laser, a YAG laser, an XeCl excimer laser, or a nitrogen laser. An ultraviolet LED may be used as the exposure light source. The radiation is preferably in the range of 190 to 450 nm.

The exposure dose of the radiation is generally preferably from 10 to 10,000 J / m &lt; ² &gt;.

Examples of the alkali developer include sodium carbonate, sodium hydrogencarbonate, sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide, choline, 1,8-diazabicyclo- [5.4.0] 1,5-diazabicyclo- [4.3.0] -5-nonene and the like are preferable.

To the alkali developing solution, a water-soluble organic solvent such as methanol or ethanol, a surfactant, or the like may be added in an appropriate amount. After the alkali development, it is usually washed with water.

As the development treatment method, a shower development method, a spray development method, a dipping (immersion) development method, a puddle (liquid immersion) development method, or the like can be applied. The developing conditions are preferably 5 to 300 seconds at room temperature.

The post-baking condition is usually about 180 to 280 DEG C for about 10 to 60 minutes.

The film thickness of the thus formed pixel is usually 0.5 to 5 占 퐉, preferably 1.0 to 3 占 퐉.

As a second method for manufacturing a color filter, a method of obtaining pixels of respective colors by an inkjet method disclosed in Japanese Patent Laid-Open Nos. 7-318723 and 2000-310706 can do. In this method, a barrier wall serving also as a light shielding function is formed on the surface of a substrate. Subsequently, the liquid composition of, for example, a blue thermosetting coloring composition is ejected by an ink jet apparatus in the partition wall formed, and then the solvent is evaporated by prebaking. Subsequently, this coating film is exposed, if necessary, and then post-baked to form a blue pixel pattern.

Then, a green pixel pattern and a red pixel pattern are sequentially formed on the same substrate by using the respective thermosetting coloring compositions of green or red. Thereby, a color filter in which pixel patterns of three primary colors of blue, green, and red are arranged on a substrate is obtained. However, in the present invention, the order of forming the pixels of each color is not limited to the above.

In addition, the partition wall has a thicker film thickness than the black matrix used in the above-mentioned first method, because it has a function of not mixing the thermosetting colored composition of each color ejected into the partition as well as the light shielding function. Thus, the barrier ribs are usually formed using a black radia radiation composition.

The substrate and the light source of radiation used for forming the color filter, and the methods and conditions of prebaking and postbaking are the same as those of the first method described above. The film thickness of the pixel formed by the ink jet method is about the same as the height of the partition wall.

After forming a protective film on the thus-obtained pixel pattern as necessary, a transparent conductive film is formed by sputtering. After a transparent conductive film is formed, a spacer may be further formed to form a color filter. The spacer is usually formed using a radiation sensitive composition, and may be a spacer (black spacer) having light shielding properties. In this case, a radiation-sensitive coloring composition in which a black coloring agent is dispersed is used, and the coloring composition of the present invention can be suitably used for forming such a black spacer.

The radiation-sensitive coloring composition of the present invention can be suitably used for forming any color-cured film such as each color pixel, a black matrix, and a black spacer used in the color filter.

The color filter including the colored cured film of the present invention thus formed is extremely useful for a color liquid crystal display element, a color image pickup tube element, a color sensor, an organic EL display element, an electronic paper, and the like because its luminance and color purity are very high. The display device described later may be any one provided with at least one colored cured film formed using the radiation sensitive coloring composition of the present invention.

Display element

The display element of the present invention comprises the colored cured film of the present invention. Examples of the display element include a color liquid crystal display element, an organic EL display element, and an electronic paper.

The color liquid crystal display device comprising the colored cured film of the present invention may be of a transmissive type or a reflective type, and a suitable structure may be adopted. For example, it is possible to adopt a structure in which a color filter is formed on a substrate different from a substrate on which a thin film transistor (TFT) is disposed and a substrate on which a driving substrate and a color filter are formed face each other with a liquid crystal layer interposed therebetween have. In addition, a substrate on which a color filter is formed on the surface of a driving substrate on which a thin film transistor (TFT) is disposed, and an ITO (tin-doped indium oxide) electrode or an IZO (mixture of indium oxide and zinc oxide) A structure in which the substrate faces the liquid crystal layer may be adopted. The latter structure can remarkably improve the aperture ratio and has an advantage that a bright and high-definition liquid crystal display element can be obtained. When adopting the latter structure, the black matrix or the black spacer may be formed on either the substrate on which the color filter is formed or the substrate on which the ITO electrode or the IZO electrode is formed.

The color liquid crystal display device having the colored cured film of the present invention may include a backlight unit using a white LED as a light source in addition to a cold cathode fluorescent lamp (CCFL). Examples of white LEDs include white LEDs that combine red LEDs, green LEDs, and blue LEDs to obtain white light by mixing colors, white LEDs that combine blue LEDs, red LEDs, and green phosphors to obtain white light by mixing colors, A white LED for obtaining a white light by mixing a red light emitting phosphor and a green light emitting phosphor and a white LED for obtaining a white light by mixing a blue LED and a YAG based phosphor, a blue LED, an orange light emitting phosphor and a green light emitting phosphor, A white LED for obtaining white light by mixing white light, an ultraviolet LED and a red LED, a white LED for obtaining a white light by mixing a green light emitting fluorescent substance and a blue light emitting fluorescent substance, and the like.

The color liquid crystal display device having the colored cured film of the present invention may be applied to a color liquid crystal display device such as a twisted nematic (TN) type, a super twisted nematic (STN) type, an in-plane switching (IPS) type, a vertical alignment (VA) type, an optically compensated birefringence ) Type liquid crystal mode can be applied.

Further, the organic EL display device having the colored cured film of the present invention can have a suitable structure, for example, a structure disclosed in Japanese Patent Laid-Open No. 11-307242.

Further, the electronic paper having the colored cured film of the present invention can have a suitable structure, and for example, there is a structure disclosed in Japanese Patent Laid-Open No. 2007-41169.

[Example]

Hereinafter, embodiments of the present invention will be described in more detail with reference to examples. However, the present invention is not limited to the following examples.

<Synthesis of colorant>

Synthesis Example 1

(Synthesis of Polymer (1)) [

5.46 g of triethylamine salt of p- (vinylphenyl) trifluoromethanesulfonylimidate, 4.51 g of methyl methacrylate and 0.130 g of? -Thioglycerol were added to a reaction vessel equipped with a cooling tube, and 20 g of cyclohexanone &Lt; / RTI &gt; The solution was heated to 100 DEG C with stirring under a nitrogen stream. While stirring at the same temperature, a solution of 98.0 mg of?,? '- azobisisobutyronitrile dissolved in 10.4 g of cyclohexanone was added dropwise over 30 minutes, and stirring was continued for 3 hours at the same temperature after completion of dropwise addition. Thereafter, the reaction solution was cooled to room temperature, and 60 g of acetone was added to make a homogeneous solution. This solution was added dropwise to 1.1 L of hexane, and the resulting precipitate was collected by filtration and washed with hexane. The resulting solid was dried under reduced pressure at 50 占 폚 to obtain 8.14 g of a polymer represented by the following structural formula. The obtained polymer had Mw of 7,800 and Mn of 3,600, and it was confirmed by ¹ H-NMR analysis that the ratio of p and r was 1 / 2.2 as a molar ratio (p / r). This is referred to as Polymer (1).

(Synthesis of polymer A)

2.0 g of the above polymer (1) was dissolved in 40 mL of acetone. Subsequently, as shown in the following reaction formula, an equimolar amount of the compound (1) is added to the molar amount of the constituent unit derived from the triethylamine salt of p- (vinylphenyl) trifluoromethanesulfonylimidic acid calculated from the copolymerization ratio of the polymer (1) was added thereto, followed by stirring at room temperature for 1 hour. Thereafter, the reaction solution was concentrated under reduced pressure, and 200 ml of ion-exchanged water was added to the obtained residue. The resulting precipitate was filtered out and washed with water. The resulting solid was dried under reduced pressure at 50 占 폚 to obtain 2.54 g of polymer A represented by the following structural formula. Polymer A corresponds to this coloring agent.

Synthesis Example 2

(Synthesis of Polymer (2)) [

Styrene sulfonic acid tetraethylammonium salt was used instead of the triethylamine salt of p- (vinylphenyl) trifluoromethanesulfonylimidate in the synthesis of Polymer (1), the same procedure as in Synthesis Example 1 was carried out to give 8.29 g of the polymer (2) represented by the structural formula was obtained. The obtained polymer (2) had Mw of 8,800 and Mn of 4,300, and it was confirmed by ¹ H-NMR analysis that the ratio of p and r was 1 / 2.8 at a molar ratio (p / r).

(Synthesis of polymer B)

In the synthesis of polymer A, 2.50 g of polymer B represented by the following structural formula was obtained in the same manner as in Synthesis Example 1, except that Polymer (2) was used instead of Polymer (1) as shown in the following reaction formula. Polymer B is not the main colorant.

Synthesis Example 3

(Synthesis of polymer (3)) [

4.55 g of p- (vinylphenyl) normal nonafluorobutanesulfonylimidic acid triethylamine salt, 5.41 g of methyl methacrylate and 0.130 g of? -Thioglycerol were added to a reaction vessel equipped with a cooling tube, and cyclohexanone &Lt; / RTI &gt; The solution was heated to 100 DEG C with stirring under a nitrogen stream. While stirring at the same temperature, a solution of 98.0 mg of?,? '- azobisisobutyronitrile dissolved in 10.4 g of cyclohexanone was added dropwise over 30 minutes, and stirring was continued for 3 hours at the same temperature after completion of dropwise addition. Thereafter, the reaction solution was cooled to room temperature, and 60 g of acetone was added thereto to obtain a homogeneous solution, which was added dropwise to 1.1 L of hexane. The resulting precipitate was filtered off and washed with hexane. The resulting solid was dried under reduced pressure at 50 캜 to obtain 8.02 g of a polymer represented by the following structural formula. The obtained polymer had Mw of 7,500 and Mn of 3,300, and it was confirmed by ¹ H-NMR analysis that the ratio of p and r was 1 / 2.6 as a molar ratio (p / r). This is referred to as Polymer (3).

(Synthesis of polymer C)

2.43 g of polymer C represented by the following structural formula was obtained in the same manner as in Synthesis Example 1, except that Polymer (3) was used in place of Polymer (1) in the synthesis of Polymer A. Polymer C corresponds to this coloring agent.

Synthesis Example 4

(Synthesis of Polymer (4)) [

6.11 g of the following compound (2), 3.85 g of methyl methacrylate and 0.130 g of? -Thioglycerol were added to a reaction vessel equipped with a cooling tube and dissolved in 20 g of cyclohexanone. The solution was heated to 100 DEG C with stirring under a nitrogen stream. While stirring at the same temperature, a solution of 98.0 mg of?,? '- azobisisobutyronitrile dissolved in 10.4 g of cyclohexanone was added dropwise over 30 minutes, and stirring was continued for 3 hours at the same temperature after completion of dropwise addition. Thereafter, the reaction solution was cooled to room temperature, and 60 g of acetone was added thereto to obtain a homogeneous solution, which was added dropwise to 1.1 L of hexane. The resulting precipitate was filtered off and washed with hexane. The resulting solid was dried under reduced pressure at 50 占 폚 to obtain 8.25 g of a polymer represented by the following structural formula. The obtained polymer had a Mw of 8,000 and a Mn of 4,100, and it was confirmed by ¹ H-NMR analysis that the ratio of p and r was 1 / 1.9 as a molar ratio (p / r). This is referred to as Polymer (4).

(Synthesis of polymer D)

In Synthesis of Polymer A, 2.65 g of Polymer D represented by the following structural formula was obtained in the same manner as in Synthesis Example 1, except that Polymer (4) was used instead of Polymer (1) as shown in the following reaction formula. Polymer D corresponds to this coloring agent.

Synthesis Examples 5 to 15

(Synthesis of Polymers E to O)

Polymers E to O were obtained in the same manner as in Synthesis Example 1 except that in the synthesis of Polymer A, the reaction was carried out by the combination of the raw materials shown in Table 1. Polymers E to O all correspond to this colorant.

Further, C.I. The structure of the numbered compound is as follows.

Synthesis Example 16

5.21 g of the compound (1) represented by the following formula and 4.31 g of bis (trifluoromethanesulfonyl) imide lithium were added to a 100 mL Erlenmeyer flask equipped with a stirrer, and 50 mL of chloroform and 25 mL of ion-exchanged water were added. And stirred for 2 hours. Thereafter, the water layer was separated and removed, and the organic layer was washed twice with ion-exchanged water. The organic layer was concentrated under reduced pressure, and the residue was dried under reduced pressure at 50 DEG C for 12 hours to obtain 7.42 g of a compound represented by the following structural formula. The resulting compound is designated as dye A. Dye A is not this coloring agent.

Production Examples 1 to 16

The obtained polymers A to O and dye A and propylene glycol monomethyl ether acetate were mixed as shown in Table 2 to prepare a polymer solution or a dye solution. In Table 2, propylene glycol monomethyl ether acetate was abbreviated as PGMEA.

Production Example 17

15 parts by mass of CI Pigment Green 58 as a coloring agent, 12.5 parts by mass (solid content concentration: 40% by mass) of BYK-LPN21116 (manufactured by BYK) as a dispersant and 72.5 parts by mass of propylene glycol monomethyl ether acetate as a solvent , And treated with a beads mill to prepare a pigment dispersion (a-1).

Production Example 18

15 parts by mass of CI Pigment Yellow 138 as a coloring agent, 12.5 parts by mass (solid content concentration: 40% by mass) of BYK-LPN21116 (manufactured by BYK) as a dispersant and 72.5 parts by mass of propylene glycol monomethyl ether acetate as a solvent , And treated with a beads mill to prepare a pigment dispersion (a-2).

&Lt; Synthesis of binder resin >

Synthesis Example 17

To a flask equipped with a cooling tube and a stirrer, 100 parts by mass of propylene glycol monomethyl ether acetate was charged and replaced with nitrogen. The mixture was heated to 80 占 폚 and, at the same temperature, 100 parts by mass of propylene glycol monomethyl ether acetate, 20 parts by mass of methacrylic acid, 10 parts by mass of styrene, 5 parts by mass of benzyl methacrylate, 15 parts by mass of 2-hydroxyethyl methacrylate , 23 parts by mass of 2-ethylhexyl methacrylate, 12 parts by mass of N-phenylmaleimide, 15 parts by mass of succinic acid mono (2-acryloyloxyethyl) and 2,2'-azobis (2,4- And 6 parts by mass of styrene-maleic anhydride) was dropped over 1 hour, and polymerization was carried out at this temperature for 2 hours. Thereafter, the temperature of the reaction solution was raised to 100 占 폚 and further polymerized for 1 hour to obtain a binder resin solution (solid content concentration: 33% by mass). The resulting binder resin had Mw of 12,200 and Mn of 6,500. This binder resin is referred to as &quot; binder resin (B1) &quot;.

Diatomaceous  Preparation of coloring composition for evaluation

Production Example 19

(A) 25.5 parts by mass of the pigment dispersion (a-1) and 25.0 parts by mass of the pigment dispersion (a-2) as the colorant, 26.3 parts by mass of the binder resin (B1) solution as the binder resin, 9.9 parts by mass of a mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate (trade name: KAYARAD DPHA, manufactured by Nippon Kayaku Kabushiki Kaisha) as a photopolymerization initiator, 2-benzyl-2-dimethylamino , 1.8 parts by mass of 1- (4-morpholinophenyl) butan-1-one (trade name Irgacure 369, manufactured by Ciba Specialty Chemicals) and 0.1 part by mass of NCI-930 (manufactured by Adeka Kagaku) 0.05 part by mass of Megaface F-554 (manufactured by DIC Corp.) as a surfactant, and propylene glycol monomethyl ether acetate as a solvent were mixed to prepare a green coloring composition (G) having a solid concentration of 20 mass%.

&Lt; Preparation and evaluation of colored composition >

Example 1

(A), 7.2 parts by mass of a polymer solution (A-1) as a colorant, 9.9 parts by mass of a binder resin (B1) solution as a binder resin (B), (C) 15.4 parts by mass of a mixture of bisphenol A (trade name, manufactured by Nippon Kayaku Kabushiki Kaisha, trade name: KYALAD DPHA) and 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) (Product name: Irgacure 369, manufactured by Ciba Specialty Chemicals), 0.1 part by mass of NCI-930 (manufactured by Adeka Kagaku Co., Ltd.), and 0.1 part by mass of Megaface F-554 ), And propylene glycol monomethyl ether acetate as a solvent were mixed to prepare a colored composition (S-1) having a solid content concentration of 20 mass%.

Evaluation of heat resistance

The coloring composition (S-1) was applied on a soda glass substrate having a SiO ₂ film formed on its surface to prevent the dissolution of sodium ions using a spin coater, and then pre-baked on a hot plate at 90 캜 for 2 minutes, Thereby forming a coating film having a thickness of 2.5 탆.

Subsequently, after cooling the substrate to room temperature, each coating film was exposed to radiation including wavelengths of 365 nm, 405 nm, and 436 nm at an exposure dose of 400 J / m ² through a photomask using a high-pressure mercury lamp. Subsequently, a developer containing 0.04 mass% potassium hydroxide aqueous solution at 23 캜 was ejected onto these substrates at a developing pressure of 1 kgf / cm ² (nozzle diameter: 1 mm) to perform showering for 90 seconds. Thereafter, this substrate was washed with ultrapure water, air-dried, and post-baked in a 200 ° C clean oven for 30 minutes to form a dot pattern on the substrate.

The chromaticity coordinate value (x, y) and the magnetic pole value (Y) in the CIE colorimetric system were measured using a C light source and a 2-degree field of view, using a color analyzer (MCPD2000 manufactured by Otsuka Denshi Co., Ltd.).

Subsequently, the substrate was further baked at 230 캜 for 90 minutes, and the chromaticity coordinate value (x, y) and the stimulus value (Y) were measured, and the color change before and after the additional baking, that is,? E * ab was evaluated. As a result, a case where the value of? E * ab was less than 2.0 was evaluated as?, A case where the value of? E * ab was less than 2.0, a case of not less than 2.0 and less than 4.0 was evaluated as?, A case of not less than 4.0 and 6.0 was evaluated as? The evaluation results are shown in Table 3. It can be said that the smaller the value of? E * ab is, the better the heat resistance is.

Solvent-resistant  evaluation

The coloring composition (S-1) was applied on a soda glass substrate having a SiO ₂ film formed on its surface to prevent the dissolution of sodium ions using a spin coater, and then pre-baked on a hot plate at 90 캜 for 2 minutes, Thereby forming a coating film having a thickness of 2.5 탆.

Subsequently, after cooling the substrate to room temperature, each coating film was exposed to radiation including wavelengths of 365 nm, 405 nm, and 436 nm at an exposure dose of 400 J / m ² through a photomask using a high-pressure mercury lamp. Subsequently, a developer containing 0.04 mass% potassium hydroxide aqueous solution at 23 캜 was ejected onto these substrates at a developing pressure of 1 kgf / cm ² (nozzle diameter: 1 mm) to perform showering for 90 seconds. Thereafter, this substrate was washed with ultrapure water, air-dried, and post-baked in a clean oven at 230 캜 for 30 minutes to form a dot pattern on the substrate. The chromaticity coordinate value (x, y) and the magnetic pole value (Y) in the CIE colorimetric system were measured using a C light source and a 2-degree field of view, using a color analyzer (MCPD2000 manufactured by Otsuka Denshi Co., Ltd.).

Thereafter, the substrate was immersed in propylene glycol monomethyl ether acetate at 80 DEG C for 40 minutes. The chromaticity coordinate value (x, y) and the magnetic pole value (Y) were measured with respect to the dot pattern after immersion, and the color change before and after immersion, that is,? E * ab was evaluated. As a result, the case where the value of DELTA E * ab was less than 3.0 was evaluated as &quot;? &Quot;, the case where the value of DELTA E * ab was less than 3.0 was evaluated as DELTA, The evaluation results are shown in Table 3. In addition, the smaller the value of? E * ab, the better the solvent resistance.

Migratory  evaluation

The green coloring composition (G) was applied on a soda glass substrate having a SiO ₂ film formed on its surface to prevent dissolution of sodium ions using a spin coater and prebaked on a hot plate at 90 캜 for 2 minutes to form a film thickness A coating film having a thickness of 2.4 탆 was formed.

Subsequently, after cooling the substrate to room temperature, each coating film was exposed to radiation including wavelengths of 365 nm, 405 nm, and 436 nm at an exposure dose of 400 J / m ² using a high-pressure mercury lamp. Subsequently, a developer containing 0.04 mass% potassium hydroxide aqueous solution at 23 캜 was ejected onto these substrates at a developing pressure of 1 kgf / cm ² (nozzle diameter: 1 mm) to perform showering for 90 seconds. Thereafter, this substrate was washed with ultrapure water, air-dried, and post-baked in a clean oven at 230 캜 for 30 minutes to form a green cured film (T-1) on the substrate. The chromaticity coordinate value (x, y) and the magnetic pole value ((x, y)) in the CIE colorimetric system were measured with a C light source and a 2-degree field of view using the color analyzer (MCPD2000 manufactured by Otsuka Denshi Co., Y) was measured.

Subsequently, the colored composition (S-1) was applied on the green cured film (T-1) using a spin coater and then pre-baked on a hot plate at 90 DEG C for 2 minutes to form a coating film having a thickness of 2.5 mu m Respectively. Then, by this after the substrate cooled to room temperature and discharged to the developing solution to the developing pressure 1kgf / cm ² (nozzle diameter of 1mm) containing 0.04% by weight of 23 ℃ aqueous solution of potassium hydroxide with respect to the substrates, performing the shower developing 90 seconds Respectively. Thereafter, this substrate was washed with ultrapure water and air-dried. A series of steps from the application of the coloring composition (S-1) to the air drying is referred to as &quot; (Step-1) &quot;. (X, y) and a magnetic pole value (Y) were measured with respect to the green cured film (T-1) after the (process-1) . As a result, the case where the value of? Y was less than 0.2 was evaluated as &quot;?&Quot;, the case of 0.2 or more and less than 0.7 was evaluated as &quot; DELTA &quot; The evaluation results are shown in Table 3. It can be said that the smaller the value of? Y is, the more the dyeing is suppressed.

Examples 2 to 14 and Comparative Examples 1 to 2

Coloring compositions (S-2) to (S-16) were prepared in the same manner as in Example 1 except that the kind and amount of the coloring agent and the binder resin solution were changed as shown in Table 1 . The obtained coloring composition was evaluated in the same manner as in Example 1. The evaluation results are shown in Table 3.

Claims (6)

(A) a colorant and (C) a polymerizable compound,
Wherein the colorant comprises a polymer having a structural unit represented by the following formula (1).

[In the formula (1)
R ⁰ represents a hydrogen atom or a methyl group,
X represents a group having a linking group containing a carbon atom, a hydrogen atom or an atom other than a halogen atom between CC bonds of a halo group, a halogenated hydrocarbon group, or a halogenated hydrocarbon group,
Y represents a single bond or a divalent organic group,
Z ⁺ is a triarylmethane type cationic chromophore represented by the following formula (2-1), a triarylmethane type cationic chromophore represented by the following formula (2-2), a methine type cationic chromophore, At least one selected from the group consisting of a cationic chromophore of a cationic chromophore, a cationic chromophore of a diarylmethane series, a cationic chromophore of a quinone imine series, a cationic chromophore of an anthraquinone series, a cationic chromophore of a phthalocyanine series and a cationic chromophore of a xanthene series One kind of cationic chromophore]

[In the formula (2-1)
R ¹ to R ⁶ independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 8 carbon atoms, or a substituted or unsubstituted aryl group,
R ⁷ to R ⁹ independently represent an alkyl group or a chlorine atom having 1 to 8 carbon atoms,
l and m independently represent an integer of 0 to 4,
n represents an integer of 0 to 6,
Provided that l, m and n are 0 at the same time]

In the formula (2-2)
R ¹¹ to R ¹⁶ independently represent a hydrogen atom, a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 8 carbon atoms, or a substituted or unsubstituted aryl group,
R ¹⁷ to R ¹⁹ independently represent an alkyl group having 1 to 8 carbon atoms or a chlorine atom,
s, t and u independently represent an integer of 0 to 4) The compound according to Claim 1, wherein Y is a divalent hydrocarbon group, a group formed by combining a divalent hydrocarbon group and a linking group containing an atom other than a carbon atom and a hydrogen atom, or a divalent group in which a part of hydrogen atoms of these groups are substituted with a halogen atom Lt; / RTI &gt; The positive resist composition according to claim 1 or 2, wherein Z ⁺ is a triarylmethane type cationic chromophore represented by the formula (2-1), a triarylmethane type cationic chromophore represented by the formula (2-2) Wherein the cationic chromophore is at least one cationic chromophore selected from the group consisting of a cationic chromophore of the system and a cationic chromophore of the xanthene system. The coloring composition according to any one of claims 1 to 3, further comprising (B) a binder resin. A colored cured film formed using the coloring composition according to any one of claims 1 to 4. A display element comprising the colored cured film according to claim 5.