KR101921752B1 - Coloring composition, color filter and display device - Google Patents

Abstract

It is an object of the present invention to provide a coloring composition containing a colorant excellent in heat resistance.
A solving means of the present invention is a colored composition containing (A) a colorant, (B) a binder resin and (C) a crosslinking agent, and is a coloring composition containing (A) a colorant represented by the following formula (1)
≪ Formula 1 >
X ⁺ Z ^-
Wherein X ⁺ represents a cationic chromophore and Z ^- represents a conjugate base of an organic acid having a halogenated hydrocarbon group.

Description

COLORING COMPOSITION, COLOR FILTER AND DISPLAY DEVICE,

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a coloring composition, a color filter, and a display device, and more particularly, to a coloring composition, a color filter and a display device which are preferably used for a color filter such as a transmissive or reflective color liquid crystal display device, , A coloring composition containing the coloring agent, a color filter including the coloring layer containing the coloring agent, and a display element having the color filter.

In the production of a color filter using a coloring and radiation-sensitive composition, a coloring and radiation-sensitive composition of a pigment dispersion type is coated on a substrate and dried. Then, the dry film is irradiated with a radiation pattern in a desired pattern (Hereinafter, referred to as " color images ") and then developing them to obtain pixels of respective colors (Patent Documents 1 and 2). A method of forming a black matrix using a photopolymerizable composition in which carbon black is dispersed (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 (Patent Document 4).

[0004] It is known that it is effective to use a dye as a coloring agent in order to realize high brightness of a display element, high color purity of a display element, or high definition of a solid-state image pickup element. For example, Patent Document 5 proposes the use of a triarylmethane-based dye having a specific structure.

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. 2008-304766

However, the triarylmethane-based dyes proposed in Patent Document 5 are insufficient in heat resistance, and the superiority of the chromaticity characteristics to the pigments is lost by heating (post-baking) after exposure and development exceeding 200 캜. From the above background, development of dyes excellent in heat resistance is strongly demanded.

Accordingly, an object of the present invention is to provide a coloring composition containing a colorant excellent in heat resistance. Another object of the present invention is to provide a color filter comprising a colored layer formed using the colored composition, and a display device having the color filter.

As a result of intensive studies, the inventors of the present invention have found that the aforementioned problems can be solved by including a basic dye having a conjugated base of an organic acid having an acidity higher than that of a normal sulfonic acid as an anion moiety.

That is, the present invention relates to a colored composition comprising (A) a colorant, (B) a binder resin and (C) a crosslinking agent, wherein (A) a colorant represented by the following formula (1) And to provide a colored composition containing the same.

Wherein X ⁺ represents a cationic chromophore and Z ^- represents a conjugate base of an organic acid having a halogenated hydrocarbon group.

In the present invention, Z < ^- > is preferably an anion represented by the following formula (1a) or an anion represented by the following formula (1b).

<Formula 1a>

[In the formula (Ia), R ¹ represents a halogenated hydrocarbon group which may have a linking group containing a carbon atom, a hydrogen atom and an atom other than a halogen atom]

&Lt; EMI ID =

[In the formula (1b), R ² independently represents a halogenated hydrocarbon group which may have a linking group including a carbon atom, a hydrogen atom and an atom other than a halogen atom, and R ² may be bonded to each other to form a ring]

The present invention also provides a color filter comprising a coloring layer formed using the coloring composition, and a display element comprising the color filter. Here, the &quot; colored layer &quot; means each color pixel, a black matrix, a black spacer, and the like used in the color filter.

This colorant has excellent heat resistance. By using the coloring composition of the present invention containing this coloring agent, a coloring layer can be formed that maintains excellent coloring characteristics even after a high-temperature heating process.

Therefore, the coloring composition containing this colorant is very useful for the production of various color filters including color filters for color liquid crystal display devices, color filters for color separation of solid-state image pickup devices, color filters for organic EL display devices, Can be preferably used. The present colorant can also be suitably used for coloring plastic moldings, colorants for inkjet inks, colorants for color toners, colorants for electrophoretic display devices, and the like.

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 is characterized by containing (A) this coloring agent as a coloring agent, that is, the coloring agent represented by the above-mentioned formula (1). This colorant is a compound having a maximum molar extinction coefficient in a visible light region (380 nm to 780 nm) of usually 3,000 or more, and is a triarylsulfonium perfluoroalkylsulfonate known as a photoacid generator that absorbs ultraviolet rays to generate an acid And so on.

First, Z ^- in formula (1) will be explained.

Z ^- is not particularly limited as long as it is a conjugate base of an organic acid having a halogenated hydrocarbon group. Examples of the organic acid having a halogenated hydrocarbon group include sulfonic acid (-SO ₃ H) having a halogenated hydrocarbon group, sulfonimidic acid (-SO ₂ NHSO ₂ -). The present inventors contemplate that by introducing a conjugate base of an organic acid having a stronger acidity as a basic colorant, that is, a colorant containing a cation as a chromophore, the ionic bonding strength is enhanced and the heat resistance of the colorant is enhanced.

Specific examples of Z ^- include an anion represented by the following formula (1a) and an anion represented by the following formula (1b).

<Formula 1a>

&Lt; EMI ID =

Next, the definitions of symbols in formulas (1a) and (1b) will be described.

R ¹ and R ² represent a halogenated hydrocarbon group which may have a linking group including a carbon atom, a hydrogen atom and an atom other than a halogen atom. Examples of the hydrocarbon group constituting the skeleton include (1) an aliphatic hydrocarbon group, (2 (3) an aliphatic hydrocarbon group having an alicyclic hydrocarbon group as a substituent (hereinafter referred to as an "alicyclic hydrocarbon-substituted aliphatic hydrocarbon group"), (4) an aromatic hydrocarbon group, (5) an aliphatic hydrocarbon group (Hereinafter referred to as an "aliphatic hydrocarbon-substituted aromatic hydrocarbon group"), and (6) an aliphatic hydrocarbon group having an aromatic hydrocarbon group as a substituent (hereinafter referred to as "aromatic hydrocarbon-substituted aliphatic hydrocarbon group" . The hydrocarbon group constituting the skeleton of R ¹ and R ² 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, preferably 1 to 20 carbon atoms, more preferably 1 to 8 carbon atoms. The alicyclic hydrocarbon group (2) is preferably an alicyclic saturated hydrocarbon group, preferably 3 to 20 carbon atoms, more preferably 3 to 12 carbon atoms. The alicyclic hydrocarbon-substituted aliphatic hydrocarbon group (3) is preferably an alicyclic saturated hydrocarbon-substituted alkyl group, and its total carbon number is preferably 4 to 20, and more preferably 6 to 14. The aromatic hydrocarbon group (4) preferably has 6 to 14 carbon atoms (more preferably 6 to 10 carbon atoms), and particularly preferably a phenyl group. 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. 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. The alkyl group in this paragraph may be straight-chain or branched.

Among these, examples of the hydrocarbon group constituting the backbone of R ¹ and R ² (1) an aliphatic hydrocarbon group, (3) alicyclic hydrocarbon group-substituted aliphatic hydrocarbon group, (4) an aromatic hydrocarbon group, (5) an aliphatic hydrocarbon substituted aromatic hydrocarbon group or (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. In the formula (1b), R ² may bond to each other to form a divalent hydrocarbon group.

Further, in R ¹ and R ² , fluorine is preferable as the halogen in the halogenated hydrocarbon group from the viewpoint of the heat resistance of the colorant. By selecting fluorine as a substituent, it is considered that the anion portion of the present colorant becomes a conjugate base of an organic acid having a higher acidity than that of the present colorant, so that a salt having a stronger ion-binding force is formed and heat resistance is enhanced.

In R ¹ and R ² , the linking group containing an atom other than a carbon atom, a hydrogen atom and a halogen atom includes -O-, -S-, -CO-, -COO-, -CONH-, -SO ₂ - And the like. The carbon number in the identification number <0035> means the total carbon number of the part excluding the carbon atoms constituting the linking group.

In the present invention, R ¹ and R ² are preferably groups represented by the following formula (1-1) or (1-2) in view of the heat resistance of the colorant, The group represented by the formula (1-1) is preferred.

In the formula (1-1), R ¹⁹ 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 ²⁰ COOR ²¹ - or R ²⁰ COOR ²¹ CFH- (R ²⁰ represents an alkyl group, an alicyclic hydrocarbon group, a heteroaryl group or a substituted or unsubstituted aryl group, and R ²¹ represents a methylene group or an alkylene group), n represents an integer of 1 or more, )

In the formula (1-2), R ¹⁴ to R ¹⁸ independently represents a hydrogen atom, a fluorine atom, a hydroxyl group, an alkyl group, a fluorinated alkyl group or alkoxy group each other, "*" has been shown to combine hand, provided that R ¹⁴ to And at least one of R &lt; ¹⁸ &gt; is a fluorine atom or a fluorinated alkyl group]

In the formula (1-1), R ^{19 is preferably a} fluorine atom, an alkyl fluoride group, an alicyclic hydrocarbon group, an alkoxy fluoride group, R ²⁰ COOR ²¹ - or R ²⁰ COOR ²¹ CFH-, more preferably a fluorine atom, an alicyclic hydrocarbon Group, a perfluoroalkoxy group, R ²⁰ COOCH ₂ CH ₂ - or R ²⁰ COOCH ₂ CH ₂ CFH-.

R ²⁰ represents an alkyl group, an alicyclic hydrocarbon group, a heteroaryl group or a substituted or unsubstituted aryl group, but the alkyl group may be linear or branched, and the alkyl group has 1 to 12 carbon atoms (more preferably 1 to 8 carbon atoms) . The alicyclic hydrocarbon group may be a 2- to 4-fold bridged alicyclic hydrocarbon group, and the alicyclic hydrocarbon group preferably has 3 to 20 carbon atoms (more 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. As the aryl group, an aryl group having 6 to 14 carbon atoms (more preferably 6 to 10 carbon atoms) is preferable, and a phenyl group is particularly preferable. The substituent 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, the position and the number of the substituent are arbitrary, , The substituents may be the same or different.

R ²¹ represents a methylene group or an alkylene group, but a methylene group or an alkylene group having 2 to 6 carbon atoms is preferable, and an ethylene group is particularly preferable from the viewpoint of ease of production.

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

In the formula (1-2), it is preferable that at least three of R ¹⁴ to R ¹⁸ are a fluorine atom or an alkyl fluoride group. In the general formula (2), it is also preferable that R ² bond to each other to form an alkylene fluoride group, particularly a perfluoroalkylene group.

Representative examples of anions represented by the above formula (1-1) or (1-2) include anions represented by the following group a and group b.

[Compound group a]

[Compound group b]

Next, X ⁺ in the general formula (1) will be described.

X ⁺ is not particularly limited as long as it is a cationic chromophore, that is, a cation forming a basic colorant as X ⁺ Z ^- . Examples thereof include triarylmethane chromophore, methine chromophore, azo chromophore, diarylmethane chromophore, quinone An imine chromophore, an anthraquinone chromophore, a phthalocyanine chromophore, and a xanthan-based chromophore.

The triarylmethane chromophore is preferably represented by the following formula (2). The cations represented by the following formula (2) may have various resonance structures, but in the present specification, when the cations represented by the respective formulas have a resonance structure, they are equivalent to the cations represented by the corresponding formulas.

R ³ and R ⁴ independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; R ⁵ and R ⁶ independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms R ⁷ represents a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, -COOR '(R' represents a hydrogen atom or an alkyl group having 1 to 8 carbon atoms) or a chlorine atom, R ⁸ and R ¹¹ Each independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms, or R ⁸ and R ¹¹ are united to form a sulfur atom, and R ⁹ and R ¹⁰ independently represent a hydrogen atom, an alkyl group having 1 to 8 carbon atoms Or a chlorine atom, and Y represents a hydrogen atom or a group represented by the following formula (3)

[In the formula (3), R ¹² and R ¹³ independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms]

As the arene ring in Ar, an arene ring having 6 to 20 carbon atoms (more preferably 6 to 10 carbon atoms) is preferable, and specific examples thereof include benzene ring, naphthalene ring, biphenyl ring and anthracene ring.

Examples of the alkyl group having 1 to 8 carbon atoms in R ¹² and R ¹³ according to Formula 3 include R ³ to R ¹¹ (including R 'in -COOR' in R ⁷ ) according to Formula 2, For example, methyl, ethyl, propyl, isopropyl, butyl, sec. Butyl, tert.butyl, isobutyl, amyl, tertiary amyl, hexyl, heptyl, octyl, isooctyl, .

Among the cations represented by the formula (2), cations represented by the following formula (4) are particularly preferred from the viewpoint of improvement in luminance and color purity.

[In the formula ^{4, R 3, R 4,} R 5, R 6, R 12 and R ¹³ has the formula 2 and ^{3 R 3, R 4, R} 5, R 6, R 12 and R ¹³ in the Agreement]

In the formula (4), R ³ , R ⁴ , R ¹² and R ¹³ are preferably alkyl groups having 1 to 8 carbon atoms (more preferably 1 to 6 carbon atoms), and R ⁵ preferably has 1 to 8 carbon atoms Is preferably an alkyl group having 1 to 6 carbon atoms or a phenyl group, and R ⁶ is preferably an alkyl group having 1 to 8 carbon atoms (more preferably 1 to 6 carbon atoms) or a hydrogen atom.

Representative examples of the cations represented by the formula (2) include cations represented by the following group c and group d, and among them, the compounds c2, c3 and c4 are preferable.

[Compound group c]

[Compound group d]

The methine chromophores are preferably represented by the following chemical formulas (5-1) to (5-3).

Wherein R ³¹ represents a hydrogen atom or a halogen atom, 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 represents -CH = CH-, -CH = CH-NR ³⁷ - (R ³⁷ represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms) ^{-CH = N-NR 37 - (} R 37 is the agreement with Im) or ^{-N = N-NR 37 - (} R 37 is the agreement with Im) represents a, R ^a is a substituted or unsubstituted aromatic hydrocarbon group or a substituted Or an unsubstituted heterocyclic ring.

As R ^a, groups represented by the following formulas (5a) to (5g) are preferable.

Wherein 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, and R ⁴⁰ and R ⁴² , R ⁴³ and R ⁴⁴ independently represent a hydrogen atom or an alkyl group having 1 to 6 carbon atoms; R ⁴¹ and R ⁴⁶ independently represent a hydrogen atom, a halogen atom, an alkoxy group having 1 to 6 carbon atoms, a substituted or unsubstituted An alkyl group having 1 to 6 carbon atoms, a nitro group, a hydroxyl group or a cyano group]

Examples of the substituent of the alkyl group include a halogen atom, a cyano group, and a hydroxyl group.

Representative examples of the cations represented by the above formulas (5-1) to (5-3) include cations represented by the following group of compounds e.

[Compound group e]

The azo-based chromophore is preferably represented by the following chemical formulas (6-1) to (6-6).

Wherein 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 each independently represent a hydrogen atom, a halogen atom, 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, and R ⁵⁸ represents an alkyl group having 1 to 6 carbon atoms , R ⁵⁹ represents a group forming quaternary ammonium, and R ^b represents a substituted or unsubstituted aromatic hydrocarbon group or a substituted or unsubstituted heterocyclic group.

R ^{59 is} -NR ⁶¹ C _m H _2m N ⁺ R ⁶² R ⁶³ R ⁶⁴ (m is an integer of 1 to 5, R ⁶¹ is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, R ⁶² , R ⁶³ , R ⁶⁴ represents independently an alkyl group having 1 to 6 carbon atoms from each ^{_{other), -COC m H 2m N +}} R 62 R 63 R 64 (m, R 62, R 63 and R ⁶⁴ are synonymous with the Im), -C _m H _2m 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 m are as defined above]

The R ^b is preferably a group represented by the following formulas (6a) to (6e), or a substituted or unsubstituted phenyl group.

Wherein 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 an alkyl group or a phenyl group of a hydrogen atom, a C 1 -C 6, R ⁶⁸ denotes a hydrogen atom or an alkyl group having 1 to 6, R ⁶⁹ denotes a hydrogen atom or an alkyl group having 1 to 6, R ⁷⁰ to R ⁷³ independently represents a hydrogen atom, a halogen atom, 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]

Examples of the substituent of the alkyl group include a halogen atom, a hydroxyl group, a cyano group, and a -CONH ₂ group. Examples of the substituent of the phenyl group include a halogen atom, 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.

Representative examples of the cations represented by the formulas (6-1) to (6-6) include, for example, cations represented by the following group f or group g.

[Compound group f]

[Compound group g]

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

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

Representative examples of the cations represented by the formulas (7-1) to (7-2) include, for example, cations represented by the following group of compounds h.

[Compound group h]

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

In the formula (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 are independently of each other represents a hydrogen atom, a substituted or unsubstituted alkoxy group, a phenyl group or a benzyl group having 1 to 6 carbon atoms, having 1 to 6 carbon atoms, R ¹⁰⁷ and R ¹¹³ are independently of each other , 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]

Examples of the substituent of the alkyl group include a halogen atom, a hydroxyl group, and a cyano group.

Representative examples of the cations represented by the above formulas (8-1) to (8-3) include, for example, cations represented by the following group of compounds i.

[Compound group i]

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

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.

Examples of the substituent of the alkyl group or phenyl group include an alkyl group having 1 to 6 carbon atoms, a halogen atom, a hydroxyl group, and a cyano group. Examples of the substituent of the alkylene group include a hydroxyl group, a cyano group, and a nitro group.

Representative examples of the cations represented by the formula (9-1) or (9-2) include, for example, cations represented by the following group of compounds j.

[Compound group j]

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

[In the formula (10), CuPc represents a copper phthalocyanine residue, and T represents a group represented by the following formula (10a) or (10b)

<Formula 10a>

&Lt; Formula 10b >

[In the formula 10a and ^{10b, R 151, R 152,} R 153, R 154, R 155, R 156, R 157 and R ¹⁵⁸ independently represents an alkyl group or a phenyl group of a hydrogen atom, a group having 1 to 6 carbon atoms from each other, p Independently represent an integer of 2 to 8, and m is as defined above]

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

[Compound group k]

The xanthene-based chromophore is preferably represented by the following formula (11).

[Formula 11]

R ¹⁵⁹ , R ¹⁶⁰ , R ¹⁶¹ and R ¹⁶² independently represent a hydrogen atom, -R ¹⁶⁶ 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 ¹⁶⁶ , -OH 16, -OR ¹⁶⁶ , -SO ₃ H, -SO ₃ M, -CO ₂ H, -CO ₂ R ¹⁶⁶ , -SO ₃ R ¹⁶⁶ , -SO ₂ NHR ¹⁶⁷ or -SO ₂ NR ¹⁶⁷ R ¹⁶⁸ There may be,

R ¹⁶³ and R ¹⁶⁴ independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms,

R ¹⁶⁵ represents -SO ₃ H, -SO ₃ M, -CO ₂ H, -CO ₂ R ¹⁶⁶ , -SO ₃ R ¹⁶⁶ , -SO ₂ NHR ¹⁶⁷ or -SO ₂ NR ¹⁶⁷ R ¹⁶⁸ ,

q represents an integer of 0 to 5, and when q is an integer of 2 or more, a plurality of R ^{165 s} may be the same or different,

R ¹⁶⁶ represents 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 included in the saturated hydrocarbon group may be an oxygen atom, a carbonyl group, or -NR ¹⁶⁶ - May be substituted,

R ¹⁶⁷ and R ¹⁶⁸ independently represent a linear or branched alkyl group having 1 to 10 carbon atoms, a cycloalkyl group having 3 to 30 carbon atoms, or -Q, or a cycloalkyl group having 1 to 10 carbon atoms formed by bonding R ¹⁶⁷ and R ¹⁶⁸ together A hydrogen atom contained in the alkyl group and the cycloalkyl group may be substituted with a hydroxyl group, a halogen atom, -Q, -CH = CH ₂ or -CH = CHR ¹⁶⁶ , and the alkyl group and the cyclo The methylene group contained in the alkyl group may be substituted with an oxygen atom, a carbonyl group or -NR ¹⁶⁶ -, and the hydrogen atom contained in the heterocyclic group may be substituted with -R ¹⁶⁶ , -OH or -Q,

M represents a sodium atom or a potassium atom,

Q 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 ¹⁶⁶ , -OR ¹⁶⁶ , -NO ₂ , -CH = CH ₂ , -CH = CHR ^166, or a halogen atom)

The saturated hydrocarbon group in R ¹⁶⁶ has 1 to 10 carbon atoms, and may be any of linear, branched and cyclic, and may have a crosslinked structure. Specific examples thereof include a methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, pentyl group, isopentyl group, neopentyl group, hexyl group, heptyl group, octyl group, A decyl group and the like, a cycloalkyl group such as a cyclopentyl group, a cyclohexyl group, a cycloheptyl group and a cyclooctyl group, and a bridged alicyclic hydrocarbon group such as a tricyclodecanyl group. The hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom, and examples of the halogen atom include a fluorine atom, a chlorine atom, and a bromine atom. The methylene group contained in the saturated hydrocarbon group may be substituted with an oxygen atom, a carbonyl group or -NR &lt; ¹⁰ &gt; -. For example, a group in which a methylene group contained in a saturated hydrocarbon group is substituted with an oxygen atom includes a methoxypropyl group, an ethoxypropyl group, a hexyloxypropyl group, a methoxyhexyl group, and an ethoxypropyl group.

The aromatic hydrocarbon group for R ¹⁵⁹ , R ¹⁶⁰ , R ¹⁶¹ , R ¹⁶² and Q is not particularly limited as far as the number of carbon atoms is 6 to 10, and examples thereof include a phenyl group and a naphthyl group. Examples of the halogen atom which may be substituted as the substituent of the aromatic hydrocarbon group include a fluorine atom, a chlorine atom and a bromine atom.

Examples of -SO ₃ R ^{166 in} R ¹⁵⁹ , R ¹⁶⁰ , R ¹⁶¹ , R ¹⁶² and R ¹⁶⁵ include a methanesulfonyl group, an ethanesulfonyl group, a hexanesulfonyl group and a decanesulfonyl group.

Examples of -CO ₂ R ^{166 in} R ¹⁵⁹ , R ¹⁶⁰ , R ¹⁶¹ , R ¹⁶² and R ¹⁶⁵ include methyloxycarbonyl, ethyloxycarbonyl, propyloxycarbonyl, isopropyloxycarbonyl, butyloxycarbonyl, isobutyloxycarbonyl, pentyl A cyclohexyloxycarbonyl group, a cycloheptyloxycarbonyl group, an octyloxycarbonyl group, a 2-ethylhexyloxycarbonyl group, a cyclohexyloxycarbonyl group, a cyclopentyloxycarbonyl group, a cyclohexyloxycarbonyl group, a cyclohexyloxycarbonyl group, a heptyloxycarbonyl group, Examples of the aryl group include a carbonyl group, a nonyloxycarbonyl group, a decanyloxycarbonyl group, a tricyclodecanyloxycarbonyl group, a methoxypropyloxycarbonyl group, an ethoxypropyloxycarbonyl group, a hexyloxypropyloxycarbonyl group, a 2-ethylhexyloxypropyloxycarbonyl group, a methoxyhexyloxycarbonyl group And the like.

Examples of -SO ₂ NHR ^{167 in} R ¹⁵⁹ , R ¹⁶⁰ , R ¹⁶¹ , R ¹⁶² and R ¹⁶⁵ include a sulfamoyl group, a methanesulfamoyl group, an ethanesulfamoyl group, a propanesulfamoyl group, an isopropanesulfamoyl group, An isobutane sulfamoyl group, a pentane sulfamoyl group, an isopentane sulfamoyl group, a neopentane sulfamoyl group, a cyclopentane sulfamoyl group, a hexane sulfamoyl group, a cyclohexane sulfamoyl group, a heptane sulfamoyl group, a cycloheptane sulfone group, A sulfamoyl group, a sulfamoyl group, an octanesulfamoyl group, a 2-ethylhexanesulfamoyl group, a 1,5-dimethylhexanesulfamoyl group, a cyclooctanesulfamoyl group, a nonansulfamoyl group, a decanesulfamoyl group, a tricyclodecane sulfamoyl group, Methoxypropane sulfamoyl group, ethoxypropane sulfamoyl group, propoxypropane sulfamoyl group, isopropoxypropane sulfamoyl group, hexyloxypropane sulfamoyl group, 2-ethylhexyloxypropane sulfamoyl group, methoxyhexane sulfone group, Pamoyl group, 3-phenyl-1-methylpropanesulfamoyl group, .

Examples of -SO ₂ NHR ¹⁶⁷ and -SO ₂ NR ¹⁶⁷ R ^{168 in} R ¹⁵⁹ , R ¹⁶⁰ , R ¹⁶¹ , R ¹⁶² and R ¹⁶⁵ further include the groups represented by Substituent Groups a to u shown below.

[Substituent group a]

[Substituent group b]

[Substituent group c]

[Substituent group d]

In the substituent group d, X ¹ represents a halogen atom. Examples of the halogen atom for X ¹ include a fluorine atom, a chlorine atom and a bromine atom.

[Substituent group e]

[Substituent group f]

[Substituent group g]

[Substituent group h]

In the substituent group h, X ³ represents an alkyl group having 1 to 3 carbon atoms or an alkoxy group having 1 to 3 carbon atoms, and the hydrogen atom of the alkyl group and the alkoxy group may be substituted with a halogen atom.

Examples of the alkyl group having 1 to 3 carbon atoms include a methyl group, an ethyl group, a propyl group, and an isopropyl group. Examples of the alkyl group having 1 to 3 carbon atoms substituted with a halogen atom include a perfluoromethyl group.

Examples of the alkoxy group having 1 to 3 carbon atoms include a methoxy group, ethoxy group and propoxy group.

[Substituent group i]

[Substituent Group j]

[Substituent group k]

[Substituent group l]

In the substituent group 1, X ² represents an alkyl group having 1 to 3 carbon atoms, an alkoxy group having 1 to 3 carbon atoms, a halogen atom or a nitro group, and the hydrogen atom of the alkyl group and the alkoxy group may be substituted with a halogen atom.

Examples of the halogen atom include the same ones as the above-mentioned X ^1. Examples of the alkyl group having 1 to 3 carbon atoms which may be substituted with a halogen atom and the alkoxy group having 1 to 3 carbon atoms which may be substituted with a halogen atom include the same groups as those of X ³ .

[Substituent Group m]

[Substituent Group n]

[Substituent group o]

[Substituent group p]

[Substituent Group q]

Of the substituent groups q, X ² is the same as the above.

[Substituent group r]

[Substituent Group s]

[Substituent Group t]

[Substituent group u]

Of the substituent group u, X ³ is the same as the above.

Examples of R ¹⁶⁷ and R ^{168 in} the -SO ₂ NHR ¹⁶⁷ and -SO ₂ NR ¹⁶⁷ R ¹⁶⁸ include a branched alkyl group having 6 to 8 carbon atoms, an alicyclic hydrocarbon group having 5 to 7 carbon atoms, an allyl group, An alkyl group having 2 to 8 carbon atoms, an alkyl group having 2 to 8 carbon atoms, an alkoxy group-containing alkyl group having 2 to 8 carbon atoms, an aryl group, more preferably a branched alkyl group having 6 to 8 carbon atoms, and particularly preferably a 2-ethylhexyl group.

As the substituent of the aromatic hydrocarbon group having 6 to 10 carbon atoms in R ¹⁵⁹ , R ¹⁶⁰ , R ¹⁶¹ and R ¹⁶² , an alkyl group having 1 to 4 carbon atoms, an aryl group, an alkyl-substituted phenyl group, -SO ₃ R ¹⁶⁶ or -SO ₂ NHR ¹⁶⁷ More preferably an ethyl group, a propyl group, a dimethylphenyl group, -SO ₃ R ¹⁶⁶ or -SO ₂ NHR ¹⁶⁷ .

Specific examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms and having a substituent in R ¹⁵⁹ , R ¹⁶⁰ , R ¹⁶¹ and R ¹⁶² include methylphenyl, dimethylphenyl, trimethylphenyl, ethylphenyl, hexylphenyl, decanylphenyl, , A chlorophenyl group, a bromophenyl group, a hydroxyphenyl group, a methoxyphenyl group, a dimethoxyphenyl group, an ethoxyphenyl group, a hexyloxyphenyl group, a decanyloxyphenyl group, and a trifluoromethylphenyl group.

At least one of R ¹⁵⁹ and R ¹⁶⁰ or at least one of R ¹⁶¹ and R ¹⁶² is preferably an alkyl group having 1 to 4 carbon atoms or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted.

R ¹⁵⁹ and R ¹⁶⁰ At least one of R &lt; ¹⁶¹ &gt; and R &lt; ^{162 &} Is more preferably an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted.

R ¹⁶⁵ is a carboxyl group, an ethyloxycarbonyl group, a sulfoxyl group, a 2-ethylhexyloxypropanesulfamoyl group, a 1,5-dimethylhexanesulfamoyl group, a 3-phenyl-1-methylpropanesulfamoyl group, or an isopropoxypropanesulfamoyl group Lt; / RTI &gt;

The cation represented by the formula (11) is preferably a cation represented by the following formula (11-1), (11-2), (11-3) or (11-4).

&Lt; Formula (11-1) >

Wherein R ^159a , R ^160a , R ^161a and R ^162a independently represent a hydrogen atom, -R ¹⁶⁶ or an aromatic hydrocarbon group having 6 to 10 carbon atoms, and the hydrogen atom contained in the aromatic hydrocarbon group is A halogen atom, -R ¹⁶⁶ , -OH, -OR ¹⁶⁶ , -SO ₃ H, -SO ₃ Na, -CO ₂ H, -CO ₂ R ¹⁶⁶ , -SO ₃ R ¹⁶⁶ , -SO ₂ NHR ¹⁶⁷ or -SO ₂ NR ¹⁶⁷ R ¹⁶⁸ ,

R ^165a represents -SO ₃ H, -SO ₂ NHR ¹⁶⁷ or -SO ₂ NR ¹⁶⁷ R ¹⁶⁸ ,

R ^165b represents a hydrogen atom, -SO ₃ H, -SO ₂ NHR ¹⁶⁷ or -SO ₂ NR ¹⁶⁷ R ¹⁶⁸ ,

R ¹⁶⁶ , R ¹⁶⁷ and R ¹⁶⁸ are as defined above]

&Lt; Formula (11-2) >

Wherein R ^159b , R ^160b , R ^161b and R ^162b independently represent a hydrogen atom, -R ^166b or an aromatic hydrocarbon group having 6 to 10 carbon atoms, and the hydrogen atom contained in the aromatic hydrocarbon group is A halogen atom, -R ^166b , -OH, -OR ^166b , -SO ₃ ^- , -SO ₃ Na, -CO ₂ H, -CO ₂ R ^166b , -SO ₃ H, -SO ₃ R ^166b or -SO ₂ NHR ¹⁷⁸ , &lt; / RTI &gt;

R ^163b and R ^164b independently represent a hydrogen atom or an alkyl group having 1 to 8 carbon atoms,

R ^165c represents -SO ₃ Na, -CO ₂ H, -CO ₂ R ^166b , -SO ₃ H or SO ₂ NHR ¹⁷⁸ ,

R ^166b represents a saturated hydrocarbon group having 1 to 10 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted with -OR ^166b or a halogen atom,

R ¹⁷⁸ represents a hydrogen atom, -R ^166b , -CO ₂ R ^166b or an aromatic hydrocarbon group having 6 to 10 carbon atoms, and the hydrogen atom contained in the aromatic hydrocarbon group may be substituted with -R ^166b or -OR ^166b ,

q is the same as above]

&Lt; Formula (11-3) >

In the formula (11-3), R ^159c and R ^161c independently represent a phenyl group, and the hydrogen atom contained in the phenyl group is a halogen atom, -R ^166b , -OR ^166b , -CO ₂ R ^166b , -SO ₃ R ^166b or -SO ₂ NHR ¹⁷⁸ ,

R ^165d represents -SO ₂ NHR ¹⁷⁸ ,

R ^165e represents a hydrogen atom or -SO ₂ NHR ¹⁷⁸ ,

R ^166b and R ¹⁷⁸ are as defined above]

&Lt; Formula (11-4) >

In formula (11-4), R ^159d and R ^161d independently represent a phenyl group, and the hydrogen atom contained in the phenyl group may be substituted with -R ^166b or -SO ₂ NHR ¹⁷⁸ ,

R ^165f represents -SO ₂ NHR ¹⁷⁸ ,

R ^166b and R ¹⁷⁸ are as defined above]

Representative examples of the cations represented by the formula (11) include, for example, cations represented by the following group m and group n.

[Compound group m]

[Compound group n]

Other examples of the cationic chromophore represented by X ^&lt; ^{+ &} gt ^; include a cation represented by the following group of compounds p.

[Compound group p]

This coloring agent can be produced by a known method, and can be produced, for example, by the same method as in the example of JP-A-2003-206415. When the present colorant is produced by a salt exchange reaction as in the embodiment of Japanese Patent Application Laid-Open No. 2003-206415, an anion represented by the above formula (1a) or an anion represented by the above formula (1b) is required, , Or a commercially available product may be used, and those synthesized by a known method, for example, a method described in paragraphs [0149] to [0153] of Japanese Patent Application Laid-Open No. 2008-7410 may be used. Further, when the present colorant is prepared by a salt exchange reaction using a basic dye in which the anion portion is a halogen ion as a starting material as in the embodiment of Japanese Patent Application Laid-Open No. 2003-206415, the heat resistance of the resultant colorant is further improved , It is preferable to purify the halogen ions so as not to leave as much as possible. The present colorant thus obtained is soluble in various organic solvents including ketones such as cyclohexanone, and has excellent heat resistance. In order to further improve the heat resistance, it is preferable that the halogen ion contained in the coloring composition of the present invention is as small as possible. In other words, it is preferable to use as little as possible a halogen ion content in other components described below.

These colorants may be used alone or in combination of two or more.

The colorants include, for example, when the X ⁺ is a triarylmethane-based chromophores, by using the proper combination and when dissolved in an organic solvent at a point that represents the blue to red, the coloring agent singly, or other coloring agents, for The present invention can be applied to a coloring composition for forming a blue pixel, a red pixel, and a colored layer of black.

As the coloring agent other than the present coloring agent, the color and the material can be appropriately selected depending on the use. Concretely, any of pigments, dyes and natural pigments can be used as a colorant other than the present colorant. However, since coloring layers constituting the color filter are required to have high color purity, brightness, contrast and light shielding properties, / Or a dye is preferably used.

Examples of the organic pigment include organic pigments and organic pigments. Examples of the organic pigments include pigments classified in the color index (published by CI. The Society of Dyers and Colourists). Specifically, the color index (C.I.) name is attached as follows.

C.I. Pigment Yellow 12, C.I. Pigment Yellow 13, C.I. Pigment Yellow 14, C.I. Pigment Yellow 17, C.I. Pigment Yellow 20, C.I. Pigment Yellow 24, C.I. Pigment Yellow 31, C.I. Pigment Yellow 55, C.I. Pigment Yellow 83, C.I. Pigment Yellow 93, C.I. Pigment Yellow 109, C.I. Pigment Yellow 110, C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, C.I. Pigment Yellow 153, C.I. Pigment Yellow 154, C.I. Pigment Yellow 155, C.I. Pigment Yellow 166, C.I. Pigment Yellow 168, C.I. Pigment Yellow 180, C.I. Pigment Yellow 211;

C.I. Pigment Orange 5, C.I. Pigment Orange 13, C.I. Pigment Orange 14, C.I. Pigment Orange 24, C.I. Pigment Orange 34, C.I. Pigment Orange 36, C.I. Pigment Orange 38, C.I. Pigment Orange 40, C.I. Pigment Orange 43, C.I. Pigment Orange 46, C.I. Pigment Orange 49, C.I. Pigment Orange 61, C.I. Pigment Orange 64, C.I. Pigment Orange 68, C.I. Pigment Orange 70, C.I. Pigment Orange 71, C.I. Pigment Orange 72, C.I. Pigment Orange 73, C.I. Pigment Orange 74;

C.I. Pigment Red 1, C.I. Pigment Red 2, C.I. Pigment Red 5, C.I. Pigment Red 17, C.I. Pigment Red 31, C.I. Pigment Red 32, C.I. Pigment Red 41, C.I. Pigment Red 122, C.I. Pigment Red 123, C.I. Pigment Red 144, C.I. Pigment Red 149, C.I. Pigment Red 166, C.I. Pigment Red 168, C.I. Pigment Red 170, C.I. Pigment Red 171, C.I. Pigment Red 175, C.I. Pigment Red 176, C.I. Pigment Red 177, C.I. Pigment Red 178, C.I. Pigment Red 179, C.I. Pigment Red 180, C.I. Pigment Red 185, C.I. Pigment Red 187, C.I. Pigment Red 202, C.I. Pigment Red 206, C.I. Pigment Red 207, C.I. Pigment Red 209, C.I. Pigment Red 214, C.I. Pigment Red 220, C.I. Pigment Red 221, C.I. Pigment Red 224, C.I. Pigment Red 242, C.I. Pigment Red 243, C.I. Pigment Red 254, C.I. Pigment Red 255, C.I. Pigment Red 262, C.I. Pigment Red 264, C.I. Pigment Red 272;

C.I. Pigment Violet 1, C.I. Pigment Violet 19, C.I. Pigment Violet 23, C.I. Pigment Violet 29, C.I. Pigment Violet 32, C.I. Pigment Violet 36, C.I. Pigment Violet 38;

C.I. Pigment Blue 1, C.I. Pigment Blue 15, C.I. Pigment Blue 15: 3, C.I. Pigment Blue 15: 4, C.I. Pigment Blue 15: 6, C.I. Pigment Blue 60, C.I. Pigment Blue 80;

C.I. Pigment Green 7, C.I. Pigment Green 36, C.I. Pigment Green 58;

C.I. Pigment Brown 23, C.I. Pigment Brown 25;

C.I. Pigment Black 1, C.I. Pigment Black 7.

Examples of the inorganic pigments include titanium oxide, barium sulfate, calcium carbonate, zinc oxide, lead sulfate, yellow lead, zinc sulfur, spinach (red iron oxide (III)), cadmium, , Cobalt rust, umber, titanium black, synthetic iron black, and carbon black.

In the present invention, the pigment may be purified and used by a recrystallization method, a reprecipitation method, a solvent washing method, a sublimation method, a vacuum heating method, or a combination thereof. Further, the pigment may be used by modifying its particle surface with a resin, if desired. 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 can be given. 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, it is preferable that the organic pigment is 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.

As the dye, there can be appropriately selected from among various kinds of oil-soluble dyes, direct dyes, acid dyes, metal complex dyes and the like and, for example, those having the following color index (C.I.) names.

C.I. Solvent Yellow 4, C.I. Solvent Yellow 14, C.I. Solvent Yellow 15, C.I. Solvent Yellow 24, C.I. Solvent Yellow 82, C.I. Solvent Yellow 88, C.I. Solvent Yellow 94, C.I. Solvent Yellow 98, C.I. Solvent Yellow 162, C.I. Solvent Yellow 179;

C.I. Solvent Red 45, C.I. Solvent Red 49;

C.I. Solvent Orange 2, C.I. Solvent Orange 7, C.I. Solvent Orange 11, C.I. Solvent Orange 15, C.I. Solvent Orange 26, C.I. Solvent Orange 56;

C.I. Solvent Blue 35, C.I. Solvent Blue 37, C.I. Solvent Blue 59, C.I. Solvent Blue 67;

C.I. Acid Yellow 17, C.I. Acid Yellow 29, C.I. Acid Yellow 40, C.I. Acid Yellow 76;

C.I. Acid Red 91, C.I. Acid Red 92, C.I. Acid Red 97, C.I. Acid Red 114, C.I. Acid Red 138, C.I. Acid Red 151;

C.I. Acid Orange 51, C.I. Acid Orange 63;

C.I. Acid Blue 80, C.I. Acid Blue 83, C.I. Acid Blue 90;

C.I. Acid Green 9, C.I. Acid Green 16, C.I. Acid Green 25, C.I. Acid Green 27.

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

In the present invention, when X ^{&lt; +} & gt ^; is a methine chromophore, it is preferable to use this coloring agent and another coloring agent of green in combination to form a coloring composition for green pixel formation. In this case, as the green coloring agent as the other coloring agent, a green organic pigment is preferable, and at least one kind selected from the group consisting of CI Pigment Green 7, CI Pigment Green 36 and CI Pigment Green 58 is preferable, Green Green 58 is preferred.

In the present invention, when X ⁺ is a xanthan-based chromophore, the present coloring agent may be used in combination with another red coloring agent to form a coloring composition for forming a red pixel, or a coloring composition for forming a blue pixel may be used in combination with another coloring agent .

When the present coloring agent and another coloring agent of red are used in combination to form a coloring composition for forming red pixels, a red organic pigment is preferable as the red coloring agent as another coloring agent. Pigment Red 166, C.I. Pigment Red 177, C.I. Pigment Red 224, C.I. Pigment Red 242, C.I. Pigment Red 254, and particularly preferably at least one kind selected from the group consisting of C.I. Pigment Red 177 and C.I. Pigment Red 254 is preferable.

In this case, the content of the present colorant is preferably 1 to 30% by mass, more preferably 3 to 15% by mass in the total colorant. In this case, C.I. Pigment Yellow 138, C.I. Pigment Yellow 139, C.I. Pigment Yellow 150, C.I. Pigments such as Pigment Orange 38 may be further used.

When the present coloring agent and a blue coloring agent are used in combination to form a coloring composition for forming a blue pixel, blue coloring agents as blue coloring agents and / or organic dyes are preferable as other coloring agents. Pigment Blue 1, C.I. Pigment Blue 2, C.I. Pigment Blue 3, C.I. Pigment Blue 9, C.I. Pigment Blue 10, C.I. Pigment Blue 14, C.I. Pigment Blue 15: 3, C.I. Pigment Blue 15: 6, C.I. Pigment Blue 62, C.I. Basic Blue 7, C.I. Basic Blue 11, and particularly preferably at least one species selected from the group consisting of C.I. Pigment Blue 15: 6 is preferred.

In this case, the content of the present colorant is preferably 3 to 70% by mass, more preferably 3 to 50% by mass in the total colorant. In this case, C.I. A violet colorant such as Pigment Violet 23 may be further used.

The content ratio of the (A) coloring agent is usually from 5 to 70% by mass, preferably from 5 to 60% by mass, more preferably from 5 to 60% by mass, in the solid content of the coloring composition, from the viewpoint of forming a pixel having a high luminance and excellent color purity, to be. The solid content referred to herein is a component other than the solvent described later.

In the present invention, when a pigment is used as a colorant, it can be used as a dispersant and a dispersion aid if desired. As the dispersing agent, for example, a suitable dispersing agent such as cationic, anionic and nonionic ones can be used, but a polymer dispersant is preferable. Specific examples thereof 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 dispersants, polyester dispersants, .

Dispersing agents such as Disperbyk-2000, Disperbyk-2001, BYK-LPN6919, BYK-LPN21116 and BYK-LPN21324 (manufactured by BYK), urethane dispersants Disperbyk-161, Disperbyk-162, Disperbyk-165, Disperbyk-167, Disperbyk-170 and Disperbyk-182 (all manufactured by BYK), Solsperse 76500 (manufactured by Lubrizol Corporation) , Sorbus 24000 (manufactured by Lubrizol Corporation) as a polyethyleneimine-based dispersant and Azisper PB821, Ajisper PB880, Ajisper PB880, Ajisper PB881 (manufactured by Ajinomoto Fine Techno Co., Ltd.) Manufactured by Kao Corporation).

Examples of the dispersion aid include pigment derivatives, and specific examples thereof include copper phthalocyanine, diketopyrrolopyrrole, and sulfonic acid derivatives of quinophthalone. The content of the dispersing agent and the dispersing aid can be suitably determined within a range not hindering the object of the present invention.

- (B) Binder Resin -

The coloring composition of the present invention contains (B) a binder resin. This makes it possible to improve the alkali developing property and the adhesion property to the substrate to the coloring composition. Such a binder resin is not particularly limited, but is preferably a resin having an acidic functional group such as a carboxyl group or a phenolic hydroxyl group. Among them, a polymer having a carboxyl group (hereinafter referred to as "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 unsaturated monomers such as (meth) acrylic acid, maleic acid, maleic anhydride, succinic acid mono [2- (meth) acryloyloxyethyl], omega -carboxylic polycaprolactone mono , p-vinylbenzoic acid, and the like.

These unsaturated monomers (b1) may be used alone or in admixture of two or more.

As the unsaturated monomer (b2), for example,

N-substituted maleimide such as N-phenylmaleimide, N-cyclohexylmaleimide;

Aromatic vinyl compounds such as styrene,? -Methylstyrene, p-hydroxystyrene, p-hydroxy-? -Methylstyrene, p-vinylbenzyl glycidyl ether and acenaphthylene;

Acrylates such as methyl (meth) acrylate, n-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, 2-hydroxyethyl (meth) (N = 2-10) methyl ether (meth) acrylate, polypropylene glycol (n = 2-10) methyl ether (meth) acrylate, polyethylene glycol Cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, tricyclo [5.2.1.0 ^2,6 ] decan-8- (Meth) acrylate of glycidyl (meth) acrylate, dicyclopentenyl (meth) acrylate, glycerol mono (meth) acrylate, 4-hydroxyphenyl (Meth) acrylate, 3,4-epoxycyclohexylmethyl ) Acrylate, 3 - [(meth) acryloyl-oxy-methyl] oxetane, 3- (meth) acrylic acid ester such as ethyl-3-oxetane [(meth) acryloyl-yloxymethyl];

Cyclohexyl vinyl ether, isobornyl vinyl ether, tricyclo [5.2.1.0 ^2,6 ] decan-8-yl vinyl ether, pentacyclopentadecanyl vinyl ether, 3- (vinyloxymethyl) Vinyl ethers such as;

And a macromonomer having a mono (meth) acryloyl group at the end of a polymer molecular chain such as polystyrene, polymethyl (meth) acrylate, poly-n-butyl (meth) acrylate and polysiloxane.

These unsaturated monomers (b2) may be used alone or in admixture of two or more.

In the copolymer of the unsaturated monomer (b1) and the unsaturated monomer (b2), the copolymerization ratio of the unsaturated monomer (b1) in the copolymer is preferably 5 to 50 mass%, more preferably 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 Unexamined Patent Application Publication No. 5-19467, Japanese Unexamined Patent Application Publication No. 6-230212, Japanese Unexamined Patent Publication 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 GPC (elution solvent: tetrahydrofuran), usually 1,000 to 100,000, preferably 3,000 to 50,000. If the Mw is too small, the residual film ratio of the resulting film may deteriorate, the pattern shape, heat resistance and the like may be impaired and the electrical characteristics may deteriorate. On the other hand, if Mw is too large, In addition, there is a risk that dry foreign matter tends to be generated during application by the slit nozzle method.

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

The binder resin in the present invention can be produced by a known method, but for example, Japanese Unexamined Patent Application Publication 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 by the method described above.

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

In the present invention, the content of the binder resin is usually 10 to 1,000 parts by mass, preferably 20 to 500 parts by mass, relative to 100 parts by mass of the (A) colorant. If the content of the binder resin is too small, for example, the alkali developability may deteriorate or the storage stability of the obtained color composition may deteriorate. On the other hand, when the content is too large, the colorant concentration is relatively lowered. It may be difficult to achieve the color density.

- (C) Crosslinking agent -

In the present invention, the (C) crosslinking agent 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. In the present invention, as the crosslinking agent (C), a compound having two or more (meth) acryloyl groups or a compound having two or more N-alkoxymethylamino groups is preferable, and a compound having two or more (meth) acryloyl groups And a compound having two or more N-alkoxymethylamino groups are preferably used in combination.

Specific examples of the compound having two or more (meth) acryloyl groups include a polyfunctional (meth) acrylate obtained by reacting an aliphatic polyhydroxy compound with (meth) acrylic acid, a polyfunctional (meth) acrylate 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, glycerin, trimethylol propane, pentaerythritol, dipentaerythritol, And an aliphatic polyhydroxy compound having the same trivalent or more. 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 dianhydride , And 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 ethylene oxide and / or propylene oxide modified di (meth) acrylate of bisphenol A, ethylene oxide and / or propylene oxide modified tree of isocyanuric acid (Meth) acrylate of trimethylolpropane, ethylene oxide and / or propylene oxide modified tri (meth) acrylate of trimethylolpropane, ethylene oxide and / or propylene oxide modified tri (meth) acrylate of pentaerythritol, Ethylene oxide and / or propylene oxide modified penta (meth) acrylate of dipentaerythritol, ethylene oxide of dipentaerythritol, and ethylene oxide and / or propylene oxide modified tetra (meth) acrylate of lithol, / Propylene oxide modified hexa (meth) 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. The melamine structure and the benzoguanamine structure refer to a chemical structure having at least one triazine ring or phenyl-substituted triazine ring as a basic skeleton, 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) Methyl) benzoguanamine, N, N, N ', N'-tetra (alkoxymethyl) glycoluril and the like.

Among these polyfunctional monomers, polyfunctional (meth) acrylates obtained by reacting a trifunctional or higher aliphatic polyhydroxy compound 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) ) Benzoguanamine is preferred. 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, It is particularly preferable in that 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 not easily generated on the substrate of the unexposed portion and on the light shielding layer.

In the present invention, the crosslinking agent (C) may be used alone or in combination of two or more.

The content of the crosslinking agent (C) in the present invention is preferably from 10 to 1,000 parts by mass, particularly preferably from 20 to 500 parts by mass, per 100 parts by mass of the colorant (A). In this case, if the content of the polyfunctional monomer is too small, there is a fear that sufficient curability is not obtained. On the other hand, when the content of the polyfunctional monomer is too large, when the alkali developability is imparted to the coloring composition of the present invention, alkali developability is lowered, and background contamination, film residue or the like on the substrate of the unexposed portion or on the light- And tend to occur more easily.

- (D) Photopolymerization initiator -

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

Examples of such a photopolymerization initiator include a thioxanthone compound, an acetophenone compound, a nonimidazole compound, a triazine compound, an O-acyloxime compound, an onium salt compound, a benzoin compound, an? -diketone compound, a polynuclear quinone compound, a diazo compound, and an imidosulfonate compound.

In the present invention, the photopolymerization initiator may be used alone or in combination of two or more. As the photopolymerization initiator, at least one member selected from the group consisting of a thioxanone compound, an acetophenone compound, a nonimidazole compound, a triazine compound, and an O-acyloxime compound is preferable.

Of the preferred photopolymerization initiators in the present invention, specific examples of the thioxanthone compound include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, and the like.

Specific examples of the acetophenone-based compound include 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane- -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, 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 the photopolymerization initiator, it is preferable to use a hydrogen donor in combination because it can improve the sensitivity. The term "hydrogen donor" as used herein means a compound capable of donating a hydrogen atom to a radical generated from a nonimidazole-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'-bis Ethylamino) benzophenone, and the like. In the present invention, the hydrogen donors may be used singly or in combination of two or more, but it is preferable to use at least one kind of mercaptan hydrogen donor and at least one amine hydrogen donor in combination to further improve the sensitivity .

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, Bis (trichloromethyl) -s-triazine, 2- [2- (4-diethylamino-2-methylphenyl) ethenyl] 2- (4-methoxyphenyl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- (Trichloromethyl) -s-triazine, 2- (4-n-butoxyphenyl) -4 , 6-bis (trichloromethyl) -s-triazine, and other triazine compounds having a halomethyl group.

Specific examples of the O-acyloxime compound include 1,2-octanedione, 1- [4- (phenylthio) phenyl] -, 2- (O- benzoyloxime), ethanone, 1- [ 1- (9-ethyl-6- (2-methyl-4-tetrahydro-naphthalen- Yl) -, 1- (O-acetyloxime), ethanone, 1- [9-ethyl-6- { Dimethyl-1,3-dioxolanyl) methoxybenzoyl} -9H-carbazol-3-yl] -, 1- (O-acetyloxime).

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) crosslinking agent. In this case, if the content of the photopolymerization initiator is too small, the curing by exposure may become insufficient, while if it is too large, the formed colored layer tends to fall off from the substrate at the time of development.

- (E) Solvent-

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

The solvent may be appropriately selected and used as long as the components (A) to (C) constituting the coloring composition and other components are dispersed or dissolved and reacted with these components and have suitable volatility.

As such a solvent, 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 or lactams such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidone.

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-propylene glycol monomethyl ether acetate, and the like are preferable from the viewpoints of solubility, pigment dispersibility, -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.

The content of the solvent is not particularly limited, but from the standpoint of coatability, stability, and the like of the resulting colored composition, an amount such that the total concentration of each component excluding the solvent from the colored composition is 5 to 50 mass% is preferable, By mass to 40% by mass.

-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 development improver such as succinic acid mono [2- (meth) acryloyloxyethyl] phthalate mono [2- (meth) acryloyloxyethyl], omega -carboxylic polycaprolactone mono (meth) acrylate; Siloxane oligomers having a reactive functional group disclosed in JP-A-2008-242078, and the like.

The coloring composition of the present invention can be produced by an appropriate method, and examples of the method for producing the coloring composition include the methods disclosed in Japanese Patent Laid-Open Nos. 2008-58642 and 2010-132874 have. In the case of using both the present colorant and the pigment as the colorant, as disclosed in Japanese Patent Application Laid-Open No. 2010-132874, after the dye solution containing the present colorant is passed through the first filter, Mixing the thus-obtained dye solution with a separately prepared pigment dispersion or the like, and passing the obtained coloring composition through a second filter. Further, the dye containing the present colorant and the like, and the components (B) to (C), and if necessary, the component (D) and the additive component are dissolved in the solvent (E) A method in which a solution having passed through a first filter is mixed with a separately prepared pigment dispersion and the resulting colored composition is passed through a second filter is also preferable. After passing the dye solution containing the present colorant and the like through the first filter, the dye solution that has passed through the first filter and the components (B) to (C) ) Component and an additive component are mixed and dissolved, the obtained solution is passed through a second filter, and further, the solution having passed through the second filter is mixed with a separately prepared pigment dispersion, and the resulting colored composition is passed through a third filter Is also preferable.

Color filter and manufacturing method thereof

The color filter of the present invention comprises a colored layer containing the present colorant.

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 where a pixel is to be formed, if necessary. Subsequently, a liquid composition of a blue radiation sensitive composition containing the present coloring agent is coated on the substrate, and then the liquid is subjected to prebaking to evaporate the solvent to form a coated 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 blue pixel patterns are arranged in a predetermined arrangement is formed.

Subsequently, the respective coloring and radiation-sensitive compositions were applied, pre-baked, exposed, developed, and post-baked in the same manner as above using each of the green and red coloring and radiation-sensitive compositions to form a green pixel array and a red And pixel arrays are sequentially formed on the same substrate. Thereby, a color filter in which pixel arrays of three primary colors of red, green, and blue are arranged on a substrate is obtained. However, the order of forming the pixels of each color is not limited to the above.

The black matrix can be formed by forming a desired thin film of metal such as chromium by sputtering or vapor deposition using a photolithography method. However, by using a coloring and radiation-sensitive composition in which a black coloring agent is dispersed, It may be formed in the same manner as in the pixel formation. The coloring composition of the present invention can be suitably used for the formation of such a black matrix.

Examples of the substrate used for forming the color filter include glass, silicon, polycarbonate, polyester, aromatic polyamide, polyamideimide, and polyimide.

If desired, these substrates may be subjected to appropriate pretreatment such as chemical treatment with a silane coupling agent, plasma treatment, ion plating, sputtering, gas phase reaction, vacuum deposition, and the like.

When the coloring and radiation-sensitive 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 or a bar coating method can be employed. , Slit die coating method is preferably employed.

The 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 a film thickness after drying, which is usually 0.6 to 8.0 탆, preferably 1.2 to 5.0 탆.

Examples of the light source used for forming the pixel and / or the black matrix include a lamp light source such as a xenon 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 laser beam source such as an ion laser, a YAG laser, a XeCl excimer laser, or a nitrogen laser, but radiation having a wavelength in the range of 190 to 450 nm is preferable.

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

Examples of the alkaline developer include sodium carbonate, sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide, choline, 1,8-diazabicyclo- [5.4.0] -7- undecene, Diazabicyclo- [4.3.0] -5-nonene and the like are preferable.

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

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

The post-baking conditions are usually about 120 to 280 DEG C for about 10 to 60 minutes, but the post baking temperature is preferably 240 DEG C or less, particularly preferably 230 DEG C or less, from the viewpoint of the heat resistance of the present colorant.

The film thickness of the thus formed pixel is usually 0.5 to 5.0 mu m, preferably 1.0 to 3.0 mu m.

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, first, a partition wall serving also as a light shielding function is formed on the surface of the substrate. Then, the liquid composition of the blue coloring composition containing the coloring agent, for example, is ejected in the partition wall by the ink jet apparatus, and then the solvent is evaporated by prebaking. Subsequently, this coating film is exposed, if necessary, and then cured by post-baking to form a blue pixel pattern.

Subsequently, a green pixel pattern and a red pixel pattern are sequentially formed on the same substrate using each of the green or red coloring compositions in the same manner as described above. Thus, a color filter in which pixel patterns of three primary colors of red, green, and blue 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 barrier rib has a function of preventing the coloring composition of each color ejected into the compartment from being mixed, as well as the light-shielding function, so that the barrier is thicker than the black matrix used in the first method. Therefore, the barrier rib is usually formed using a black radia radiation composition.

The substrate or radiation source used for forming the color filter, and the methods and conditions of prebaking and postbaking are the same as those of the first method. Thus, 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 required, a transparent conductive film is formed by sputtering. After forming the transparent conductive film, a spacer may be further formed to form a color filter. The spacer is usually formed using a radiation sensitive composition, but it may also be a spacer (black spacer) having light shielding properties. In this case, a coloring and radiation-sensitive composition in which a black coloring agent is dispersed is used, but the coloring composition of the present invention can be preferably used for forming such a black spacer.

The color filter of the present invention thus obtained 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 of its extremely high luminance and color purity.

Display element

The display device of the present invention comprises the color filter 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 having the color filter of the present invention can take an appropriate structure. For example, the color filter may be formed on a substrate separate from the driving substrate on which the thin film transistor (TFT) is disposed, so that the substrate on which the driving substrate and the color filter are formed faces the liquid crystal layer , 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 a substrate on which ITO (indium oxide doped with indium) electrode is formed face each other through a liquid crystal layer have. 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.

The color liquid crystal display device having the color filter of the present invention may have a backlight unit using a white LED as a light source in addition to a cold cathode fluorescent lamp (CCFL). As the white LED, for example, a white LED that obtains white light by using a red LED having an independent spectrum, a green LED and a blue LED, a white LED that combines a red LED, a green LED, and a blue LED to obtain white light by mixing colors, A white LED that obtains white light by mixing LEDs with a red LED and a green phosphor, a white LED that obtains white light by mixing white light by combining a blue LED, a red light emitting phosphor, and a green light emitting phosphor, and a mixture of a blue LED and a YAG- A white LED for obtaining a white light by mixing a combination of an orange light emitting phosphor and a green light emitting phosphor, a combination of an ultraviolet LED, a red light emitting phosphor, a green light emitting phosphor and a blue light emitting phosphor by combining a white LED, White light emitting diode (LED), and the like.

The color liquid crystal display device having the color filter of the present invention may be applied to a color liquid crystal display device such as TN (Twisted Nematic) type, STN (Super Twisted Nematic) type, IPS (In-Planes Switching) type, VA (Vertical Alignment) type, OCB (Optically Compensated Birefringence) Type liquid crystal mode can be applied.

Further, the organic EL display device having the color filter of the present invention can employ a suitable structure, for example, a structure disclosed in Japanese Patent Application Laid-Open No. 11-307242.

Further, the electronic paper having the color filter of the present invention can adopt a suitable structure, and for example, a structure disclosed in Japanese Patent Application Laid-Open No. 2007-41169 can be cited.

&Lt; Example 1 >

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.

&Lt; Synthesis and evaluation of the present colorant &

1. Synthesis of the present colorant

Colorant Synthesis Example 1

1.4 g (2.72 mmol) of CI Basic Blue 7 (Cl ^- salt of the compound c2 of the above compound group c) and 0.768 g (4.08 mmol) of potassium trifluoromethanesulfonate (Wako Pure Chemical Industries) were added to a screw tube into which a stirrer was charged. , 20 mL of chloroform and 10 mL of water were added, and the mixture was stirred at room temperature for 7 hours. After the aqueous layer was separated and removed, the organic layer was washed twice with water and concentrated under reduced pressure. The resulting solid was further dried under reduced pressure to give 1.70 g of a dark brown solid (yield: 80.2%). This is referred to as Compound A. The ¹ H-NMR (solvent: deuterated chloroform) spectrum of the compound A was as follows, and it was confirmed that the compound was the target compound.

Colorant Synthesis Example 2

Colorant A colorant was synthesized in the same manner as in Colorant Synthesis Example 1 except that potassium nonafluorobutanesulfonate (manufactured by Wako Pure Chemical Industries, Ltd.) was used instead of potassium trifluoromethanesulfonate in Synthesis Example 1, and ¹ H-NMR (solvent: Deuterated chloroform), it was confirmed that the compound was the target compound. This is referred to as compound B. The ¹ H-NMR spectrum of Compound B is as follows.

Colorant Synthesis Example 3

Colorant A colorant was synthesized in the same manner as in Colorant Synthesis Example 1 except that bis (trifluoromethanesulfonyl) imide potassium was used instead of potassium trifluoromethanesulfonate in Synthesis Example 1, and ¹ H-NMR (solvent: Deuterated chloroform), it was confirmed that the compound was the target compound. This is referred to as Compound C. The &lt; ¹ &gt; H-NMR spectrum of Compound C is as follows.

Colorant Synthesis Example 4

Colorant A colorant was synthesized in the same manner as in Colorant Synthesis Example 1 except that CI Basic Blue 11 (Cl ^- salt of the compound c4 of the above compound group c) was used instead of CI Basic Blue 7 in the Synthesis Example 1, and ¹ H-NMR (Solvent: deuterated chloroform), it was confirmed that the compound was the target compound.

Colorant Synthesis Example 5

Colorant A colorant was synthesized in the same manner as in Colorant Synthesis Example 1, except that CI Basic Violet 16 (Cl ^- salt of Compound e2 of Compound Group e) was used instead of CI Basic Blue 7 in Synthesis Example 1, and ¹ H-NMR (Solvent: deuterated chloroform), it was confirmed that the compound was the target compound.

Colorant Synthesis Example 6

Colorant A colorant was synthesized in the same manner as in Colorant Synthesis Example 1 except that CI Basic Blue 41 (methane sulphate of the compound f13 of the above compound group f) was used instead of CI Basic Blue 7 in the Synthesis Example 1, and ¹ H-NMR Solvent: deuterated chloroform), it was confirmed that the compound was the target compound.

Colorant Synthesis Example 7

Colorant A colorant was synthesized in the same manner as in Colorant Synthesis Example 1, except that CI Basic Blue 3 (Cl ^- salt of the compound i4 in the above compound group i) was used instead of CI Basic Blue 7 in Synthesis Example 1, and ¹ H-NMR (Solvent: deuterated chloroform), it was confirmed that the compound was the target compound.

Colorant Synthesis Example 8

Colorant A colorant was synthesized in the same manner as in Colorant Synthesis Example 1, except that CI Basic Blue 22 (Cl ^- salt of the compound j1 in the above compound group j) was used instead of CI Basic Blue 7 in Synthesis Example 1, and ¹ H-NMR (Solvent: deuterated chloroform), it was confirmed that the compound was the target compound.

Colorant Synthesis Example 9

Except that CI Basic Red 13 (Cl ^- salt of the compound e1 of the above compound group e) was used instead of CI Basic Blue 7 in the colorant Synthesis Example 1, and bis (trifluoromethanesulfonyl) imide was used instead of potassium trifluoromethanesulfonate A colorant was synthesized in the same manner as in Colorant Synthesis Example 1 except that potassium hydroxide was used, and it was confirmed that the compound was the target compound by ¹ H-NMR (solvent: deuterated chloroform) measurement.

Colorant Synthesis Example 10

Colorant In Preparation Example 1, CI Basic Yellow 25 (Cl ^- salt of the compound f1 of the above compound group f) was used instead of CI Basic Blue 7, and bis (trifluoromethanesulfonyl) imide was used instead of potassium trifluoromethanesulfonate A colorant was synthesized in the same manner as in Colorant Synthesis Example 1 except that potassium hydroxide was used, and it was confirmed that the compound was the target compound by ¹ H-NMR (solvent: deuterated chloroform) measurement.

Colorant Synthesis Example 11

Colorant In Synthesis Example 1, CI Basic Yellow 2 (Cl ^- salt of the compound h2 of the above compound group h) was used instead of CI Basic Blue 7, and bis (trifluoromethanesulfonyl) imide was used instead of potassium trifluoromethanesulfonate A colorant was synthesized in the same manner as in Colorant Synthesis Example 1 except that potassium hydroxide was used, and it was confirmed that the compound was the target compound by ¹ H-NMR (solvent: deuterated chloroform) measurement.

Colorant Synthesis Example 12

Colorant In Synthesis Example 1, CI Basic Red 2 (Cl ^- salt of the compound i1 in the above compound group i) was used instead of CI Basic Blue 7, and bis (trifluoromethanesulfonyl) imide was used instead of potassium trifluoromethanesulfonate. A colorant was synthesized in the same manner as in Colorant Synthesis Example 1 except that potassium hydroxide was used, and it was confirmed that the compound was the target compound by ¹ H-NMR (solvent: deuterated chloroform) measurement.

Colorant Synthesis Example 13

Colorant In Synthesis Example 1, CI basic orange 24 (Cl ^- salt of the compound g3 of the above compound group g) was used instead of CI Basic Blue 7, and bis (trifluoromethanesulfonyl) imide was used instead of potassium trifluoromethanesulfonate A colorant was synthesized in the same manner as in Colorant Synthesis Example 1 except that potassium hydroxide was used, and it was confirmed that the compound was the target compound by ¹ H-NMR (solvent: deuterated chloroform) measurement.

Colorant Synthesis Example 14

In place of CI Basic Blue 7 in Colorant Synthesis Example 1, CI Basic Yellow 21 (Cl ^- salt of the compound e9 of the above compound group e) was used instead of potassium trifluoromethanesulfonate in the presence of bis (trifluoromethanesulfonyl) imide potassium , A colorant was synthesized in the same manner as in Colorant Synthesis Example 1 and confirmed to be a target compound by ¹ H-NMR (solvent: deuterated chloroform) measurement. This is referred to as Compound E. &Lt; ¹ &gt; H-NMR spectrum of Compound E is as follows.

Colorant Synthesis Example 15

1.3 g (2.71 mmol) of CI Basic Red 1 represented by the following formula, 0.766 g (4.07 mmol) of potassium trifluoromethanesulfonate (Wako Pure Chemical Industries, Ltd.), 20 mL of chloroform, and 10 mL, and the mixture was stirred at room temperature for 7 hours. After the aqueous layer was separated and removed, the organic layer was washed twice with water and concentrated under reduced pressure. The resulting solid was further dried under reduced pressure to obtain 1.61 g of a dark brown solid (yield: 72%). This is Compound G. The ¹ H-NMR (solvent: deuterated chloroform) spectrum of Compound G was as follows, confirming that the compound was the target compound.

Colorant Synthesis Example 16

Colorant A colorant was synthesized in the same manner as in Colorant Synthesis Example 15 except that potassium nonafluorobutanesulfonate (manufactured by Wako Pure Chemical Industries, Ltd.) was used instead of potassium trifluoromethanesulfonate in Synthesis Example 15, and ¹ H-NMR (solvent: Deuterated chloroform), it was confirmed that the compound was the target compound. This is referred to as compound H. &Lt; ¹ &gt; H-NMR spectrum of Compound H is as follows.

Colorant Synthesis Example 17

Colorant A colorant was synthesized in the same manner as in Colorant Synthesis Example 15 except that bis (trifluoromethanesulfonyl) imide potassium was used instead of potassium trifluoromethanesulfonate in Synthesis Example 15, and ¹ H-NMR (solvent: Deuterated chloroform), it was confirmed that the compound was the target compound. This is referred to as Compound I. &Lt; ¹ &gt; H-NMR spectrum of Compound I is as follows.

Colorant Synthesis Example 18

Colorant A colorant was synthesized in the same manner as in Colorant Synthesis Example 15, except that CI Basic Red 1 was used instead of CI Basic Red 1 in Synthesis Example 15, and a colorant was synthesized and measured by ¹ H-NMR (solvent: deuterated chloroform) It was confirmed that the compound was the target compound. This is referred to as Compound J. The ¹ H-NMR spectrum of Compound J is as follows.

Colorant Synthesis Example 19

Colorant A colorant was synthesized in the same manner as in Colorant Synthesis Example 17, except that CI Basic Violet 10 represented by the following formula was used in place of CI Basic Red 1 in Synthesis Example 17, and ¹ H-NMR (solvent: deuterated chloroform) By the measurement, it was confirmed that the compound was the target compound. This is referred to as compound K. The ¹ H-NMR spectrum of Compound K is as follows.

Colorant Synthesis Example 20

Colorant A colorant was synthesized in the same manner as in Colorant Synthesis Example 17 except that CI Basic Violet 11: 1 represented by the following formula was used in place of CI Basic Red 1 in Synthesis Example 17, and ¹ H-NMR (solvent: deuterated Chloroform), it was confirmed that the compound was the target compound. This is referred to as compound L. &Lt; ¹ &gt; H-NMR spectrum of Compound L is as follows.

Colorant Synthesis Example 21

Colorant A colorant was synthesized in the same manner as in Colorant Synthesis Example 17, except that CI Basic Red 3 represented by the following formula was used instead of CI Basic Red 1 in Synthesis Example 17, and ¹ H-NMR (solvent: deuterated chloroform) By the measurement, it was confirmed that the compound was the target compound.

Colorant Synthesis Example 22

Colorant A colorant was synthesized in the same manner as in Colorant Synthesis Example 17, except that CI Basic Red 4 represented by the following formula was used in place of CI Basic Red 1 in Synthesis Example 17, and ¹ H-NMR (solvent: deuterated chloroform) By the measurement, it was confirmed that the compound was the target compound.

Colorant Synthesis Example 23

Colorant A colorant was synthesized in the same manner as in Colorant Synthesis Example 17, except that CI Basic Violet 11 represented by the following formula was used in place of CI Basic Red 1 in Synthesis Example 17, and ¹ H-NMR (solvent: deuterated chloroform) By the measurement, it was confirmed that the compound was the target compound.

2. Evaluation of the present colorant

Colorant The compound A obtained in Synthesis Example 1 was dissolved in cyclohexanone in an amount of 10% by mass or more, and the solution showed blue color. All of the colorants obtained in Coloring Agents 2 to 23 were dissolved in cyclohexanone in an amount of 10% by mass or more.

In addition, the 5% mass reduction temperature based on the simultaneous measurement of the thermogravimetric and differential thermal analysis of the colorants obtained in the colorant preparation examples 1 to 23 was all 250 DEG C or more. On the other hand, C.I. Basic Blue 7, C.I. Basic Blue 11, C.I. Basic violet 16, C.I. Basic Blue 41, C.I. Basic Blue 3, C.I. Basic Blue 22, C.I. Basic Red 13, C.I. Basic Yellow 25, C.I. Basic Yellow 2, C.I. Basic Red 2, C.I. Basic orange 24, C.I. Basic Yellow 21, C.I. Basic Red 1, C.I. Basic Red 1: 1, C.I. Basic Red 3, C.I. Basic Red 4, C.I. Basic violet 10, C.I. Basic violet 11, C.I. The 5% mass reduction temperature based on the simultaneous thermogravimetric and differential thermal analysis of Basic Violet 11: 1 was less than 200 ° C.

&Lt; Production of Pigment Dispersion >

Production Example 1

As a colorant, C.I. 15 parts by mass of Pigment Blue 15: 6, 12.5 parts by mass (solid content concentration = 40% by mass) of BYK-LPN21116 (BYK) as a dispersant and 72.5 parts by mass of propylene glycol monomethyl ether acetate as a solvent , And treated with a bead mill to prepare a pigment dispersion (A-1).

Production Example 2

As a colorant, C.I. Pigment Blue 15: 6 instead of C.I. Pigment dispersion (A-2) was prepared in the same manner as in Production Example 1, except that Pigment Violet 23 was used.

Production Example 3

As a colorant, C.I. Pigment Blue 15: 6 instead of C.I. A pigment dispersion (A-3) was prepared in the same manner as in Production Example 1 except that Pigment Green 58 was used.

Production Example 4

As a colorant, C.I. Pigment Blue 15: 6 instead of C.I. A pigment dispersion (A-4) was prepared in the same manner as in Production Example 1 except that Pigment Yellow 150 was used.

Production Example 5

As a colorant, C.I. 15 parts by mass of Pigment Red 177, 12.5 parts by mass (solids concentration = 40% by mass) of BYK-LPN21116 (BYK) as a dispersant, and 72.5 parts by mass of propylene glycol monomethyl ether acetate as a solvent, And treated with a mill to prepare a pigment dispersion (A-5).

Production Example 6

As a colorant, C.I. Pigment Red 177 instead of C.I. Pigment Dispersion (A-6) was prepared in the same manner as in Production Example 5 except that Pigment Red 254 was used.

&Lt; Preparation of dye solution >

Production Example 7

5 parts by mass of the compound A as a coloring agent and 95 parts by mass of propylene glycol monomethyl ether acetate as a solvent were mixed to prepare a dye solution A. [

Production Example 8

5 parts by mass of the compound B as a coloring agent and 95 parts by mass of propylene glycol monomethyl ether acetate as a solvent were mixed to prepare a dye solution B. [

Production Example 9

5 parts by mass of a compound C as a colorant and 95 parts by mass of propylene glycol monomethyl ether acetate as a solvent were mixed to prepare a dye solution C. [

Production Example 10

As a colorant, C.I. 5 parts by mass of Basic Blue 7 and 95 parts by mass of propylene glycol monomethyl ether as a solvent were mixed to prepare a dye solution D. [

Production Example 11

5 parts by mass of the compound E as a coloring agent and 95 parts by mass of propylene glycol monomethyl ether acetate as a solvent were mixed to prepare a dye solution E. [

Production Example 12

As a colorant, C.I. 5 parts by mass of Basic Yellow 21 and 95 parts by mass of propylene glycol monomethyl ether acetate as a solvent were mixed to prepare a dye solution F. [

Production Example 13

20 parts by mass of the compound G as a coloring agent and 80 parts by mass of propylene glycol monomethyl ether as a solvent were mixed to prepare a dye solution G. [

Production Example 14

20 parts by mass of the compound H as a coloring agent and 80 parts by mass of propylene glycol monomethyl ether as a solvent were mixed to prepare a dye solution H.

Production Example 15

20 parts by mass of the compound I as a colorant and 80 parts by mass of propylene glycol monomethyl ether as a solvent were mixed to prepare a dye solution I,

Production Example 16

20 parts by mass of the compound J as a coloring agent and 80 parts by mass of propylene glycol monomethyl ether as a solvent were mixed to prepare a dye solution J.

Production Example 17

20 parts by mass of a compound K as a coloring agent and 80 parts by mass of propylene glycol monomethyl ether as a solvent were mixed to prepare a dye solution K. [

Production Example 18

20 parts by mass of the compound L as a coloring agent and 80 parts by mass of propylene glycol monomethyl ether as a solvent were mixed to prepare a dye solution L. [

Production Example 19

As a colorant, C.I. 20 parts by mass of Basic Red 1 and 80 parts by mass of propylene glycol monomethyl ether as a solvent were mixed to prepare a dye solution M. [

&Lt; Synthesis of binder resin >

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 benzylmethacrylate, 15 parts by mass of 2-hydroxyethylmethacrylate , 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- 6-pyrrolidone) was added dropwise over 1 hour, and the mixture was polymerized at this temperature for 2 hours. Thereafter, the temperature of the reaction solution was raised to 100 캜 and further polymerized for 1 hour to obtain a binder resin solution (solid concentration = 33% by mass). The resulting binder resin had Mw = 12,200 and Mn = 6,500. This binder resin is referred to as &quot; binder resin (B1) &quot;.

&Lt; Preparation and evaluation of colored composition >

Example 1

13.6 parts by mass of the pigment dispersion (A-1), 27.2 parts by mass of the dye solution A, 16.1 parts by mass of the binder resin (B1) solution as the binder resin, and M-402 (dipentaerythritol hexaacrylate (N, N ', N', N '', N '' - hexa (methoxymethyl) melamine produced by KANSEI CHEMICAL CO., LTD. , 2.4 parts by mass of a main component and a weight average polymerization degree of 1.3), 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one as a photopolymerization initiator (trade name IRGACURE369 manufactured by Ciba Specialty Chemicals, ), And propylene glycol monomethyl ether acetate as a solvent were mixed to prepare a coloring composition (CR1) having a solid content concentration of 20 mass%.

The coloring composition (CR1) was coated on a glass substrate using a spin coater, and then prebaked on a hot plate at 80 DEG C for 10 minutes to form a coating film. The number of revolutions of the spin coater was changed, and three coating films having different film thicknesses were formed by the same operation.

Subsequently, after cooling the substrates to room temperature, radiation containing wavelengths of 365 nm, 405 nm, and 436 nm was irradiated onto each coating film through a photomask using a high-pressure mercury lamp at an exposure dose of 2,000 J / m 2 Lt; / RTI &gt; Subsequently, a developer containing 0.04 mass% aqueous solution of potassium hydroxide at 23 占 폚 was ejected onto these substrates at a developing pressure of 1 kgf / cm2 (nozzle diameter: 1 mm) for showering for 90 seconds. Thereafter, this substrate was cleaned with ultra-pure water, air-dried, and further baked in a clean oven at 230 캜 for 30 minutes to form a cured film for evaluation.

The chromaticity coordinate values (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 the color analyzer (MCPD2000 manufactured by Otsuka Denshi Co., Ltd.) Respectively. Further, the film thickness of the obtained cured film was measured using Alpha Step IQ manufactured by KLA-Tencor Corporation. From the measurement results, the chromaticity coordinate value x, the magnetic pole value Y and the film thickness at the chromaticity coordinate value y = 0.080 were determined. The evaluation results are shown in Table 1. The larger the stimulus value Y, the higher the light transmittance (luminance) and the thinner the film thickness, the higher the coloring power.

The substrate on which the cured film was formed was sandwiched between two polarizing plates, and the front side polarizing plate was rotated while irradiating the back side with a fluorescent lamp (wavelength range of 380 to 780 nm) to measure a luminance meter LS-100 (manufactured by Minolta Co., ), The maximum and minimum values of the transmitted light intensity were measured. For each of the cured films, a value obtained by dividing the maximum value by the minimum value was defined as a contrast ratio. From the measurement results, the contrast ratio at the chromaticity coordinate value y = 0.080 was determined. The evaluation results are shown in Table 1.

Example 2

15.5 parts by mass of the pigment dispersion (A-1), 24.3 parts by mass of the dye solution B, 16.1 parts by mass of the binder resin (B1) solution as the binder resin, and M-402 (dipentaerythritol hexaacryl (N, N ', N', N '', N '' - hexa (methoxymethyl) melamine produced by KANSEI CHEMICAL CO., LTD. , 2.4 parts by mass of a main component and a weight average polymerization degree of 1.3), 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one as a photopolymerization initiator (trade name IRGACURE369 manufactured by Ciba Specialty Chemicals, ) And propylene glycol monomethyl ether acetate as a solvent were mixed to prepare a coloring composition (CR2) having a solid content concentration of 20 mass%.

Evaluation was carried out in the same manner as in Example 1 except that the coloring composition (CR2) was used instead of the coloring composition (CR1). The evaluation results are shown in Table 1.

Example 3

12.5 parts by mass of the pigment dispersion (A-1), 28.3 parts by mass of the dye solution C, 16.1 parts by mass of the binder resin (B1) solution as the binder resin, and M- 402 (dipentaerythritol hexaacryl (N, N ', N', N '', N '' - hexa (methoxymethyl) melamine produced by KANSEI CHEMICAL CO., LTD. , 2.4 parts by mass of a main component and a weight average polymerization degree of 1.3), 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one as a photopolymerization initiator (trade name IRGACURE369 manufactured by Ciba Specialty Chemicals, ), And propylene glycol monomethyl ether acetate as a solvent were mixed to prepare a coloring composition (CR3) having a solid content concentration of 20 mass%.

Evaluation was carried out in the same manner as in Example 1 except that the coloring composition (CR3) was used instead of the coloring composition (CR1). The evaluation results are shown in Table 1.

Comparative Example 1

, 4.5 parts by mass of the pigment dispersion (A-2), 16.1 parts by mass of the binder resin (B1) solution as the binder resin, 5.5 parts by mass of the crosslinking agent M-402 2-dimethylamino-1- (4-morpholinophenyl) butan-1-one (manufactured by Ciba Specialty Chemicals, Inc.) as a photopolymerization initiator, 2.4 parts by mass of MW- 2.2 parts by mass of a commercial product IRGACURE369) and propylene glycol monomethyl ether acetate as a solvent were mixed to prepare a coloring composition (CR4) having a solid concentration of 20% by mass.

Evaluation was carried out in the same manner as in Example 1 except that the coloring composition (CR4) was used instead of the coloring composition (CR1). The evaluation results are shown in Table 1.

Comparative Example 2

18.1 parts by mass of the pigment dispersion (A-1), 24.2 parts by mass of the dye solution D, 16.1 parts by mass of the binder resin (B1) solution as the binder resin, 5.5 parts by mass of the M-402 manufactured by Toagosei Co., 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one (trade name IRGACURE369, manufactured by Ciba Specialty Chemicals) as a photopolymerization initiator, 2.4 parts by mass of MW- , And propylene glycol monomethyl ether acetate as a solvent were mixed to prepare a coloring composition (CR5) having a solid content concentration of 20 mass%.

Evaluation was carried out in the same manner as in Example 1 except that the coloring composition (CR5) was used instead of the coloring composition (CR1). The evaluation results are shown in Table 1.

Example 4

, 12.3 parts by mass of the pigment dispersion (A-3), 31.3 parts by mass of the dye solution E, 16.1 parts by mass of the binder resin (B1) solution as the binder resin, 5.5 parts by mass of the crosslinking agent M-402 manufactured by Toagosei Co., 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one (trade name IRGACURE369, manufactured by Ciba Specialty Chemicals) as a photopolymerization initiator, 2.4 parts by mass of MW- , And propylene glycol monomethyl ether acetate as a solvent were mixed to prepare a coloring composition (CR6) having a solid content concentration of 20 mass%.

Evaluation was carried out in the same manner as in Example 1 except that the coloring composition (CR6) was used instead of the coloring composition (CR1). At this time, the chromaticity coordinate value x, the stimulus value (Y), the film thickness and the contrast ratio at the chromaticity coordinate value y = 0.590 were obtained. The evaluation results are shown in Table 1.

Comparative Example 3

12.1 parts by mass of the pigment dispersion (A-3), 32.5 parts by mass of the pigment dispersion (A-4), 16.1 parts by mass of the binder resin (B1) solution as the binder resin, 5.5 parts by mass of the crosslinking agent M-402 by Toagosei Co., 2-dimethylamino-1- (4-morpholinophenyl) butan-1-one (manufactured by Ciba Specialty Chemicals, Inc.) as a photopolymerization initiator, 2.4 parts by mass of MW- 2.2 parts by mass of a commercial product IRGACURE 369) and propylene glycol monomethyl ether acetate as a solvent were mixed to prepare a coloring composition (CR7) having a solid content concentration of 20% by mass.

Evaluation was carried out in the same manner as in Example 4 except that the coloring composition (CR7) was used instead of the coloring composition (CR6). The evaluation results are shown in Table 1.

Comparative Example 4

12.1 parts by mass of the pigment dispersion (A-3), 30.2 parts by mass of the dye solution F, 16.1 parts by mass of the binder resin (B1) solution as the binder resin, 5.5 parts by mass of the M-402 manufactured by Toagosei Chemical Industry Co., 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one (trade name IRGACURE369, manufactured by Ciba Specialty Chemicals) as a photopolymerization initiator, 2.4 parts by mass of MW- , And propylene glycol monomethyl ether acetate as a solvent were mixed to prepare a coloring composition (CR8) having a solid content concentration of 20 mass%.

Evaluation was carried out in the same manner as in Example 4 except that the coloring composition (CR8) was used instead of the coloring composition (CR6). The evaluation results are shown in Table 1.

Example 5

, 2.6 parts by mass of the pigment dispersion (A-6), 2.2 parts by mass of the dye solution G, 16.1 parts by mass of the binder resin (B1) solution as the binder resin, 16.6 parts by mass of the pigment dispersion (A- 5.5 parts by mass of a product M-402 (mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate) and 2 parts by mass of 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) (Trade name: IRGACURE369, manufactured by Ciba Specialty Chemicals Co., Ltd.), 0.2 part by mass of Megafac F-554 manufactured by DIC Corporation as a fluorine-based surfactant, and cyclohexanone as a solvent were mixed, A coloring composition (CR9) having a solid content concentration of 20% by mass was prepared.

Evaluation was carried out in the same manner as in Example 1 except that the coloring composition (CR9) was used instead of the coloring composition (CR1). At this time, the chromaticity coordinate value y, the stimulus value (Y), the film thickness and the contrast ratio at the chromaticity coordinate value x = 0.655 were obtained. The evaluation results are shown in Table 1.

Example 6

, 2.6 parts by mass of the pigment dispersion (A-6), 3.2 parts by mass of the dye solution H, 16.1 parts by mass of the binder resin (B1) solution as the binder resin, 16.6 parts by mass of the pigment dispersion (A- 5.5 parts by mass of a product M-402 (mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate) and 2 parts by mass of 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) (Trade name: IRGACURE369, manufactured by Ciba Specialty Chemicals Co., Ltd.), 0.2 part by mass of Megafac F-554 manufactured by DIC Corporation as a fluorine-based surfactant, and cyclohexanone as a solvent were mixed, A coloring composition (CR10) having a solid content concentration of 20 mass% was prepared.

Evaluation was carried out in the same manner as in Example 5 except that the coloring composition (CR10) was used instead of the coloring composition (CR9). The evaluation results are shown in Table 1.

Example 7

, 1.2 parts by mass of the pigment dispersion (A-5), 1.6 parts by mass of the pigment dispersion (A-6), 1.2 parts by mass of the dye solution I, 16.1 parts by mass of the binder resin (B1) solution as the binder resin, 5.5 parts by mass of a product M-402 (mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate) and 2 parts by mass of 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) (Trade name: IRGACURE369, manufactured by Ciba Specialty Chemicals Co., Ltd.), 0.2 part by mass of Megafac F-554 manufactured by DIC Corporation as a fluorine-based surfactant, and cyclohexanone as a solvent were mixed, To prepare a coloring composition (CR11) having a solid content concentration of 20 mass%.

Evaluation was carried out in the same manner as in Example 5 except that the coloring composition (CR11) was used instead of the coloring composition (CR9). The evaluation results are shown in Table 1.

Example 8

, 24.3 parts by mass of the pigment dispersion (A-5), 2.6 parts by mass of the pigment dispersion (A-6), 1.3 parts by mass of the dye solution J, 16.1 parts by mass of the binder resin (B1) solution as the binder resin, 5.5 parts by mass of a product M-402 (mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate) and 2 parts by mass of 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) (Trade name: IRGACURE369, manufactured by Ciba Specialty Chemicals Co., Ltd.), 0.2 part by mass of Megafac F-554 manufactured by DIC Corporation as a fluorine-based surfactant, and cyclohexanone as a solvent were mixed, To prepare a coloring composition (CR12) having a solid content concentration of 20 mass%.

Evaluation was carried out in the same manner as in Example 5 except that the coloring composition (CR12) was used instead of the coloring composition (CR9). The evaluation results are shown in Table 1.

Example 9

, 22.6 parts by mass of the pigment dispersion (A-5), 5.6 parts by mass of the pigment dispersion (A-6), 3.2 parts by mass of the dye solution K, 16.1 parts by mass of the binder resin (B1) solution as the binder resin, 5.5 parts by mass of a product M-402 (mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate) and 2 parts by mass of 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) (Trade name: IRGACURE369, manufactured by Ciba Specialty Chemicals Co., Ltd.), 0.2 part by mass of Megafac F-554 manufactured by DIC Corporation as a fluorine-based surfactant, and cyclohexanone as a solvent were mixed, To prepare a coloring composition (CR13) having a solid content concentration of 20% by mass.

Evaluation was carried out in the same manner as in Example 5 except that the coloring composition (CR13) was used instead of the coloring composition (CR9). The evaluation results are shown in Table 1.

Example 10

, 24.2 parts by mass of the pigment dispersion (A-5), 4.6 parts by mass of the pigment dispersion (A-6), 2.2 parts by mass of the dye solution L, 16.1 parts by mass of the binder resin (B1) solution as the binder resin, 5.5 parts by mass of a product M-402 (mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate) and 2 parts by mass of 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) (Trade name: IRGACURE369, manufactured by Ciba Specialty Chemicals Co., Ltd.), 0.2 part by mass of Megafac F-554 manufactured by DIC Corporation as a fluorine-based surfactant, and cyclohexanone as a solvent were mixed, To prepare a coloring composition (CR14) having a solid content concentration of 20 mass%.

Evaluation was carried out in the same manner as in Example 5 except that the coloring composition (CR14) was used instead of the coloring composition (CR9). The evaluation results are shown in Table 1.

Comparative Example 5

, 22.1 parts by mass of the pigment dispersion (A-5), 4.5 parts by mass of the pigment dispersion (A-6), 16.1 parts by mass of the binder resin (B1) solution as the binder resin, 5.5 parts by mass of the crosslinking agent M-402 manufactured by Toagosei Co., And 2.4 parts by mass of MW-30 manufactured by KANSEI CHEMICAL CO., LTD. And 2 parts by mass of 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one (CIBA Specialty Chemicals 2.2 parts by mass of IRGACURE 369 as a fluorine-based surfactant, 0.2 part by mass of Megafac F-554 manufactured by DIC Corporation, and propylene glycol monomethyl ether acetate as a solvent were mixed to obtain a colored composition CR15).

Evaluation was carried out in the same manner as in Example 5 except that the coloring composition (CR15) was used instead of the coloring composition (CR9). The evaluation results are shown in Table 1.

Comparative Example 6

, 4.2 parts by mass of the pigment dispersion (A-5), 4.6 parts by mass of the pigment dispersion (A-6), 2.2 parts by mass of the dye solution M, 16.1 parts by mass of the binder resin (B1) solution as the binder resin, 5.5 parts by mass of M-402, 2.4 parts by mass of MW-30 manufactured by Mitsubishi Chemical Corporation, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan- , 2.2 parts by mass of a product of Ciba Specialty Chemicals, trade name IRGACURE 369), 0.2 parts by mass of Megafac F-554 manufactured by DIC Corporation as a fluorine-based surfactant, and cyclohexanone as a solvent were mixed to obtain a copolymer having a solid concentration of 20% A coloring composition (CR16) was prepared.

Evaluation was carried out in the same manner as in Example 5 except that the coloring composition (CR16) was used instead of the coloring composition (CR9). The evaluation results are shown in Table 1.

In Table 1, &quot; B15: 6 &quot; Pigment Blue 15: 6, and &quot; G58 &quot; Pigment Green 58, and &quot; V-23 &quot; Pigment violet 23, and &quot; BB-7 &quot; Basic Blue 7 &quot;, and &quot; Y150 &quot; Pigment Yellow 150, and &quot; BY-21 &quot; Basic Yellow 21, and &quot; R254 &quot; Pigment Red 254, and &quot; R177 &quot; Pigment Red 177, and &quot; BR1 &quot; Basic Red 1 respectively.

Claims (8)

(A) a colorant, (B) a binder resin and (C) a crosslinking agent,
A coloring composition for forming a red pixel, which contains, as the coloring agent (A), a coloring agent represented by the following formula (1) and a red coloring agent other than the coloring agent represented by the formula (1).
&Lt; Formula 1 >
X ⁺ Z ^-
[In the formula (1), X < ⁺ > represents a xanthan-based chromophore and Z &lt; ^- &gt; represents an anion represented by the following formula
<Formula 1a>

(I) wherein R ¹ is a group represented by the following formula (1-1) or a group represented by the following formula (1-2)

In the formula (1-1), R ¹⁹ 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 ²⁰ COOR ²¹ - or R ²⁰ COOR ²¹ CFH- (R ²⁰ represents an alkyl group, an alicyclic hydrocarbon group, a heteroaryl group or a substituted or unsubstituted aryl group, and R ²¹ represents a methylene group or an alkylene group), n represents an integer of 1 or more, )

In the formula (1-2), R ¹⁴ to R ¹⁸ independently represent a hydrogen atom, a fluorine atom, a hydroxyl group, an alkyl group, an alkyl fluoride group, an alkoxy group or an alkylsulfonyl group, and "*" , Provided that at least one of R ¹⁴ to R ¹⁸ is a fluorine atom or an alkyl fluoride group] (A) a coloring agent, (B) a binder resin, and (C) a crosslinking agent, wherein the coloring agent (A)
&Lt; Formula 1 >
X ⁺ Z ^-
Wherein X ⁺ represents a triarylmethane chromophore, a methine chromophore, an azo chromophore, a diarylmethane chromophore, a quinoneimine chromophore, an anthraquinone chromophore or phthalocyanine chromophore, and Z ^- Lt; / RTI &gt;
&Lt; EMI ID =

[In the formula (1b), R ² is a group represented by the following formula (1-2)]

In the formula (1-2), R ¹⁴ to R ¹⁸ independently represent a hydrogen atom, a fluorine atom, a hydroxyl group, an alkyl group, an alkyl fluoride group, an alkoxy group or an alkylsulfonyl group, and "*" , Provided that at least one of R ¹⁴ to R ¹⁸ is a fluorine atom or an alkyl fluoride group] delete The coloring composition of claim 1, wherein the halogenated hydrocarbon group is a fluorinated hydrocarbon group. delete The coloring composition according to claim 1 or 2, further comprising (D) a photopolymerization initiator. A color filter comprising a colored layer formed using the coloring composition according to any one of claims 1 to 3. A display device comprising the color filter according to claim 7.