JP6812877B2 - Pigment composition for color filter, its manufacturing method, coloring composition for color filter and color filter - Google Patents

Description

The present invention relates to a coloring composition for a color filter used for manufacturing a color filter used for a color liquid crystal display device, a color image pickup tube element, and the like, and a color filter formed by using the coloring composition.

The red filter segment, which is one of the three primary colors (red, green, blue; RGB) of the color filter substrate, is generally a diketopyrrolopyrrole pigment having excellent brightness. I. In addition to Pigment Red 254, C.I. is an anthraquinone pigment with an excellent contrast ratio. I. Pigment Red 177 is used as the main pigment, but each has advantages and disadvantages, and C.I. I. The development of an alternative material for Pigment Red 177 is desired.

Patent Document 1 describes a specific azo pigment as a pigment having excellent brightness. However, even with this, sufficient brightness could not be obtained, and further improvement was required from the viewpoint of dispersion stability.

Japanese Unexamined Patent Publication No. 2014-160160

The problems to be solved by the present invention are excellent dispersibility when used in a coloring composition for a color filter, high brightness when used in a color filter, good heat resistance and light resistance, and a coating film. It is an object of the present invention to provide a coloring composition for a color filter without foreign matter, and a color filter using the same.

That is, in the present invention, the azo pigment (A1) represented by the following general formula (1) and the azo pigment (A2) represented by the following general formula (2) or the azo pigment represented by the following general formula (3) A pigment composition for a color filter containing (A3), the azo pigment (A1) represented by the general formula (1), the azo pigment (A2) represented by the general formula (2), or the general. The azo pigment (A2) represented by the general formula (2) or the azo pigment (A3) represented by the general formula (3) with respect to the total amount of the azo pigment (A3) represented by the formula (3). The present invention relates to a pigment composition for a color filter having a content of 2.0 to 20.0% by mass.

General formula (1)

[In the general formula (1), _Ra and R _b each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group which may have a substituent. X and Y independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, or a trifluoromethyl group. ]

General formula (2)

[In the general formula (2), _Ra and R _b each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group which may have a substituent. X and Y independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, or a trifluoromethyl group. ]

General formula (3)

[In the general formula (3), _Ra and R _b each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group which may have a substituent. X and Y independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, or a trifluoromethyl group. ]

Further, in the present invention, the azo pigment (A1) represented by the general formula (1) and the azo pigment (A2) represented by the general formula (2) or the azo pigment (A3) represented by the general formula (3). The content of the azo pigment (A2) represented by the general formula (2) or the azo pigment (A3) represented by the general formula (3) is 2.0 to 10.0% by mass with respect to the total amount of The present invention relates to the above pigment composition for a color filter.

The present invention also relates to the above pigment composition for a color filter containing an azo pigment (A1) represented by the general formula (1) and an azo pigment (A2) represented by the general formula (2).

The present invention further relates to the pigment composition for a color filter containing a dye derivative.

The present invention also relates to a coloring composition for a color filter comprising at least a coloring agent and a binder resin, wherein the coloring agent contains the pigment composition for the color filter.

Further, in the present invention, the colorant is further described in C.I. I. Pigment Red 254, C.I. I. The present invention relates to the above-mentioned coloring composition for a color filter, which contains at least one selected from the group consisting of Pigment Red 242 and a brominated diketopyrrolopyrrole pigment.

The present invention further relates to the coloring composition for a color filter, which further contains at least one selected from the group consisting of a photopolymerizable monomer and a photopolymerization initiator.

The present invention also relates to a color filter having a filter segment formed from the coloring composition for a color filter on a substrate.

Furthermore, the present invention relates to a method for producing a pigment composition for a color filter, which comprises subjecting an amine compound represented by the following general formula (4) and a dinaphthol compound represented by the following general formula (5) to a coupling reaction. ..

General formula (4)

[In the general formula (4), _Ra and R _b each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group which may have a substituent. ]

General formula (5)

[In the general formula (5), X and Y are independently hydrogen atom, halogen atom, cyano group, nitro group, alkyl group having 1 to 4 carbon atoms, alkoxyl group having 1 to 4 carbon atoms or trifluoro. Represents a methyl group. ]

The pigment composition for a color filter of the present invention contains an azo pigment (A1) and an azo pigment (A2 or A3) in a specific ratio, so that the azo pigment (A2 or A3) has a sizing effect on the azo pigment (A1). It is possible to provide a color filter which exhibits extremely excellent brightness and dispersion stability, and further has good heat resistance and light resistance.

Hereinafter, the present invention will be described in detail. The "CI" listed below means a color index (CI). In the present specification, the "azo pigment represented by the general formula (1)" may be abbreviated as "pigment" and the "coloring composition for color filter" may be abbreviated as "coloring composition". ..

<Pigment composition for color filter>
<Azo pigment (A1) represented by the general formula (1), azo pigment (A2) represented by the general formula (2), azo pigment (A3) represented by the general formula (3)>
The pigment composition for a color filter of the present invention has an azo pigment (A1) represented by the following general formula (1), an azo pigment (A2) represented by the following general formula (2), or the following general formula (3). It is characterized by containing the azo pigment (A3) represented by (A3) in a specific ratio.

General formula (1)

[In the general formula (1), _Ra and R _b each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group which may have a substituent. X and Y independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, or a trifluoromethyl group. ]

General formula (2)

[In the general formula (2), _Ra and R _b each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group which may have a substituent. X and Y independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, or a trifluoromethyl group. ]

General formula (3)

[In the general formula (3), _Ra and R _b each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group which may have a substituent. X and Y independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, or a trifluoromethyl group. ]

The substituents of the general formulas (1), (2) and (3) will be described below.

The alkyl group having 1 to 4 carbon atoms in R _a and R _b may be linear or branched, and specifically, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec. -Butyl group and tert-butyl group can be mentioned.

Substituents in the phenyl group which may have a substituent in R _a and R _b include a halogen atom (including a fluorine atom, a chlorine atom and a bromine atom), an alkyl group having 1 to 4 carbon atoms, and a trifluoro. Examples thereof include an alkoxycarbonyl group having 2 to 4 carbon atoms such as a methyl group and a methoxycarbonyl group, and substituents are bonded to each other by a divalent group such as a ureyl group (-NHCONH-) to form a ring such as a benzimidazolone ring. May be formed.

The alkyl group having 1 to 4 carbon atoms in X and Y may be linear or branched, and specifically, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl. Examples include a tert-butyl group.

The alkoxyl group having 1 to 4 carbon atoms in X and Y may be linear or branched, and specifically, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, an isobutoxy group, sec-. Examples thereof include a butoxy group and a tert-butoxy group. It is preferably a methoxy group.

Examples of the halogen atom in X and Y include a fluorine atom, a chlorine atom and a bromine atom. It is preferably a chlorine atom.

In the general formulas (2) and (3), when X and Y are not the same substituent, for example, "X and Y are hydrogen atoms or chlorine atoms, and X and Y are not the same", X. Can have two types of structures: a structure 1 in which is a hydrogen atom and Y is a chlorine atom, and a structure 2 in which X is a chlorine atom and Y is a hydrogen atom. Such structures 1 and 2 may be distinguished from a and b.

In the coloring composition of the present invention, from the viewpoint of brightness, dispersibility, heat resistance and light resistance, it is preferable that either R _a or R _b is a phenyl group which may have a substituent. More preferably, the substituent is a hydrogen atom. Further, at least one of X and Y is preferably a halogen atom, and preferably a chlorine atom. Further, it is more preferable that both X and Y are chlorine atoms.

The pigment composition for a color filter of the present invention contains an azo pigment (A1) and an azo pigment (A2 or A3) in a specific ratio, so that the azo pigment (A2 or A3) has a sizing effect on the azo pigment (A1). Although it exhibits extremely excellent brightness and dispersion stability, the azo pigment (A2) is more preferable than the azo pigment (A3) from the viewpoint of brightness and dispersion stability.

The coloring composition of the present invention may have a chemical structure of the general formulas (1), (2) and (3), or a polymorph of each, or may be a pigment having any crystal form. , So-called polymorphs, which may be mixed crystals of pigments having any crystal morphology. The crystal morphology of these pigments can be confirmed by powder X-ray diffraction measurement and X-ray crystal structure analysis.

Specific examples of the azo pigment of the present invention are shown in Table 1 below, but the present invention is not limited thereto. When X and Y are not the same, the azo pigment (A2) and the azo pigment (A3) may contain two types of structures a and b, as described above.

<Production method of azo pigment (A1) and azo pigment (A2) (Scheme A)>
The azo pigment (A1) and the azo pigment (A2) can be obtained by a conventionally known production method. The azo pigment (A1) and the azo pigment (A2) are cups of amines (diazo component) represented by the following general formula (4) and dinaphthol (coupling component) represented by the general formula (5). It can be obtained by ring reaction.

General formula (4)

[In the general formula (4), _Ra and R _b each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group which may have a substituent. ]

General formula (5)

[In the general formula (5), X and Y are independently hydrogen atom, halogen atom, cyano group, nitro group, alkyl group having 1 to 4 carbon atoms, alkoxyl group having 1 to 4 carbon atoms or trifluoro. Represents a methyl group. ]

In the coupling reaction, the acidity of the diazonium salt obtained by diazotizing the amines represented by the general formula (4) with nitrite, nitrite or nitrite in an acidic solution containing hydrochloric acid, sulfuric acid, acetic acid or the like. This is done by adding an alkaline solution of the coupling component to the solution. The alkali metal hydroxide used to dissolve the coupling component, such as sodium hydroxide, is preferably in an amount sufficient to neutralize the acid liberated from the diazonium salt.

The coupling reaction is preferably carried out in a pH range of 4 to 6, and at that time, a buffer solution such as acetic acid may be used. Further, the coupling reaction is carried out in the range of 5 to 100 ° C., and the reaction proceeds rapidly. Further, since the obtained azo pigment is highly insoluble, it can be easily isolated from unreacted substances and by-products by filtration, and a highly pure pigment can be obtained. The coupling reaction can also be carried out in the presence of an organic solvent, lubricant, dispersant or emulsifier.

The dinaphthol represented by the general formula (5) is obtained by subjecting 2-hydroxy-3-naphthoic chloride represented by the following formula (6) to a diamine represented by the following general formula (7) by a condensation reaction. Can be done. In the condensation reaction, a molar ratio of 2: 1 is preferable.

Equation (6)

General formula (7)

[In the general formula (7), X and Y are independently hydrogen atom, halogen atom, cyano group, nitro group, alkyl group having 1 to 4 carbon atoms, alkoxyl group having 1 to 4 carbon atoms or trifluoro. Represents a methyl group. ]

When synthesizing the carboxylic acid chloride as represented by the formula (6), it is preferable to dry the corresponding carboxylic acid in advance or remove water by azeotropic distillation in an organic solvent. A chlorinating agent is used to chlorinate the carboxylic acid. The chlorinating agent is phosphorus pentachloride, phosphorus trichloride, preferably thionyl chloride. The chlorination reaction is preferably carried out in, for example, tetrahydrofuran (THF), pyridine, N-methyl-2-pyrrolidone (NMP), monochlorobenzene, dichlorobenzene, toluene, xylene, trimethylbenzene, nitrobenzene, or thionyl chloride. ..

The condensation reaction of carboxylic acid chloride and diamine is preferably carried out in an anhydrous solvent. Specific examples thereof include tetrahydrofuran (THF), pyridine, N-methyl-2-pyrrolidone (NMP), monochlorobenzene, dichlorobenzene, toluene, xylene, trimethylbenzene and nitrobenzene.

The carboxylic acid chloride used is preferably isolated, but it is also possible to omit this isolation step and carry out a direct condensation reaction.

<Production method of azo pigment (A1) and azo pigment (A3) (Scheme B)>
The azo pigment (A1) and the azo pigment (A3) can be obtained by a conventionally known production method. The azo pigment (A1) and the azo pigment (A3) condense the carboxylic acid chloride of the azo compound represented by the following general formula (8) and the diamine represented by the general formula (7) at a molar ratio of 2: 1. It can be obtained by reacting.

General formula (8)

[In the general formula (8), _Ra and R _b each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group which may have a substituent. ]

The carboxylic acid chloride represented by the general formula (8) is a azo compound obtained by coupling a diazo compound of amines represented by the general formula (4) with 2-hydroxy-3-naphthoic acid. It can be obtained by chlorinating the carboxylic acid derivative.

<Miniaturization of colorants>
In order to obtain high brightness and dispersion stability when the pigment composition of the present invention is used as a coloring composition, the pigment particles are refined by salt milling, acid pacing treatment or the like as necessary to obtain a color. It can be suitably used as a filter pigment. The primary particle size of the pigment is preferably 10 nm or more and 50 nm or less.

Salt milling is a machine in which a mixture of a pigment, a water-soluble inorganic salt, and a water-soluble organic solvent is heated by a kneader such as a kneader, a 2-roll mill, a 3-roll mill, a ball mill, an attritor, or a sand mill. After kneading, the water-soluble inorganic salt and the water-soluble organic solvent are removed by washing with water. The water-soluble inorganic salt acts as a crushing aid, and it is considered that the pigment is crushed by utilizing the high hardness of the inorganic salt during salt milling, which causes an active surface and crystal growth. There is. Therefore, during kneading, crushing of the pigment and crystal growth occur at the same time, and the primary particle size of the pigment obtained differs depending on the kneading conditions.

In order to promote the crystal growth of the pigment by heating, the heating temperature is preferably 35 to 150 ° C. The kneading time for salt milling is preferably 2 to 24 hours from the viewpoint of the balance between the particle size distribution of the primary particles of the salt milled pigment and the cost required for salt milling.

By optimizing the conditions for salt milling the pigment, it is possible to obtain a pigment having a very fine primary particle size, a narrow distribution width, and a sharp particle size distribution. In particular, it is preferable to use a dye derivative in combination.

Further, as the water-soluble inorganic salt used for salt milling, sodium chloride, barium chloride, potassium chloride, sodium sulfate and the like can be used, but sodium chloride (salt) is preferably used from the viewpoint of price. From the viewpoint of both treatment efficiency and production efficiency, the water-soluble inorganic salt is preferably used in an amount of 50 to 2000 parts by mass, and most preferably 300 to 1200 parts by mass with respect to 100 parts by mass of the pigment.

The water-soluble organic solvent has a function of wetting the pigment and the water-soluble inorganic salt, and is not particularly limited as long as it dissolves (mixes) in water and does not substantially dissolve the inorganic salt used. However, since the temperature rises during salt milling and the solvent easily evaporates, a high boiling point having a boiling point of 120 ° C. or higher is preferable from the viewpoint of safety. Such examples include, for example, 2-methoxyethanol, 2-butoxyethanol, 2- (isopentyloxy) ethanol, 2- (hexyloxy) ethanol, diethylene glycol, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol. , Triethylene glycol monomethyl ether, liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, liquid polypropylene glycol, etc. Is used. These water-soluble organic solvents are preferably used in an amount of 5 to 1000% by weight, most preferably 50 to 500% by weight, based on the total weight of the pigment (100% by weight).

When the pigment is salt-milled, a resin may be added if necessary. Here, the type of resin used is not particularly limited, and a natural resin, a modified natural resin, a synthetic resin, a synthetic resin modified with a natural resin, or the like can be used. The resin used is preferably solid at room temperature, water-insoluble, and more preferably partially soluble in the water-soluble organic solvent. The amount of the resin used is preferably in the range of 2 to 200% by weight based on the total weight of the pigment (100% by weight).

The water-soluble organic solvent has a function of wetting the pigment and the water-soluble inorganic salt, and is not particularly limited as long as it dissolves (mixes) in water and does not substantially dissolve the inorganic salt used. However, since the temperature rises during salt milling and the solvent easily evaporates, a high boiling point having a boiling point of 120 ° C. or higher is preferable from the viewpoint of safety. Such examples include, for example, 2-methoxyethanol, 2-butoxyethanol, 2- (isopentyloxy) ethanol, 2- (hexyloxy) ethanol, diethylene glycol, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol. , Triethylene glycol monomethyl ether, liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, liquid polypropylene glycol, etc. Is used. These water-soluble organic solvents are preferably used in an amount of 5 to 1000% by weight, most preferably 50 to 500% by weight, based on the total weight of the pigment (100% by weight).

When the pigment is salt-milled, a resin may be added if necessary. Here, the type of resin used is not particularly limited, and a natural resin, a modified natural resin, a synthetic resin, a synthetic resin modified with a natural resin, or the like can be used. The resin used is preferably solid at room temperature, water-insoluble, and more preferably partially soluble in the water-soluble organic solvent. The amount of the resin used is preferably in the range of 2 to 200% by weight based on the total weight of the pigment (100% by weight).

<Dye derivative>
When a pigment derivative is used, it is required that the color tone of the pigment composition is not impaired as much as possible. From the viewpoint of hue, as the dye derivative, an anthraquinone derivative, dianthraquinone derivative, thiazine indigo derivative, azo dye derivative, quinophthalone derivative, quinacridone derivative, diketopyrrolopyrrole derivative, naphthol derivative, or dinaphthol derivative is preferably used. However, it is more preferably an azo dye derivative, a naphthol derivative, or a dinaphthol derivative. These dye derivatives are preferably used in an amount of 2 to 30% by weight, most preferably 5 to 20% by weight, based on the total weight of the pigment (100% by weight).

(Specific examples of anthraquinone derivatives)
Specifically, as the anthraquinone derivative, a compound represented by the following formula (9) can be used, but the anthraquinone derivative is not limited thereto.

(Specific example of dianthraquinone derivative)
Specifically, as the dianthraquinone derivative, a compound represented by the following formula (10) can be used, but the dianthraquinone derivative is not limited thereto.

(Specific example of thiazine indigo derivative)
Specifically, as the thiazine indigo derivative, a compound represented by the following formula (11) can be used, but the present invention is not limited thereto.

(Specific example of azo dye derivative)
Specifically, as the azo dye derivative, compounds represented by the following formulas (12) to (14) can be used, but the azo dye derivative is not limited thereto.

(Specific example of quinophthalone derivative)
Specifically, as the quinophthalone derivative, compounds represented by the following formulas (15-1) to (15-13) can be used, but the quinophthalone derivative is not limited thereto.

(Specific example of quinacridone derivative)
Specifically, as the quinacridone derivative, a compound represented by the following formula (16) can be used, but the derivative is not limited thereto.

(Specific example of diketopyrrolopyrrole derivative)
As the diketopyrrolopyrrole derivative, specifically, a compound represented by the following formula (17) or formula (18) can be used, but the derivative is not limited thereto.

(Specific example of naphthol derivative)
Specifically, as the naphthol derivative, compounds represented by the following formulas (19-1) to (19-8) can be used, but the naphthol derivative is not limited thereto.

(Specific example of dinaphthol derivative)
Specifically, as the dinaphthol derivative, compounds represented by the following formulas (20-1) to (20-2) can be used, but the dinaphthol derivative is not limited thereto.

<Coloring composition for color filters>
The coloring composition of the present invention contains a pigment composition containing an azo pigment represented by the general formulas (1), (2) and (3) of the present invention as an essential component, and is organic in addition to a binder resin, if necessary. It is composed of a solvent, a dispersion aid, a photopolymerizable monomer, a photopolymerization initiator, a sensitizer, and other auxiliary components.

The content of the pigment composition containing the pigment composed of the compounds represented by the general formulas (1), (2) and (3) of the present invention of the present invention can be adjusted as necessary, but the coloring composition The content is preferably 0.01 to 50% by mass, more preferably 0.1 to 30% by mass.

<Binder resin>
Examples of the binder resin contained in the coloring composition for a color filter of the present invention include conventionally known thermoplastic resins and thermosetting resins. Examples of the thermoplastic resin include acrylic resin, butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, and polyurethane resin. , Polyester resin, vinyl resin, alkyd resin, polystyrene resin, polyamide resin, rubber resin, cyclized rubber resin, celluloses, polyethylene (HDPE, LDPE), polybutadiene, polyimide resin and the like.

When used as a coloring composition for a color filter, a resin having a spectral transmittance of preferably 80% or more, more preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region is preferable. When used in the form of an alkali-developable colored resist, it is preferable to use an alkali-soluble vinyl-based resin in which an acidic group-containing ethylenically unsaturated monomer is copolymerized. Further, in order to further improve the photosensitivity, an energy ray-curable resin having an ethylenically unsaturated active double bond can also be used.

Examples of the alkali-soluble resin obtained by copolymerizing an acidic group-containing ethylenically unsaturated monomer include a resin having an acidic group such as a carboxyl group and a sulfone group. Specifically, as the alkali-soluble resin, an acrylic resin having an acidic group, an α-olefin / (maleic anhydride) maleic anhydride copolymer, a styrene / styrene sulfonic acid copolymer, an ethylene / (meth) acrylic acid copolymer, or Examples thereof include isobutylene / (maleic anhydride) copolymer. Among them, an acrylic resin having an acidic group and at least one resin selected from a styrene / styrene sulfonic acid copolymer, particularly an acrylic resin having an acidic group, is preferably used because of its high heat resistance and transparency.

As an energy ray-curable resin having an ethylenically unsaturated active double bond, a polymer having a reactive substituent such as a hydroxyl group, a carboxyl group or an amino group is substituted with a reactive substituent such as an isocyanate group, an aldehyde group or an epoxy group. A resin is used in which a (meth) acrylic compound having a group or silicic acid is reacted to introduce a photocrosslinkable group such as a (meth) acryloyl group or a styryl group into the polymer. Further, a polymer containing an acid anhydride such as a styrene-maleic anhydride copolymer or an α-olefin-maleic anhydride copolymer is half-esterified with a (meth) acrylic compound having a hydroxyl group such as hydroxyalkyl (meth) acrylate. Esterified ones are also used.

As the thermoplastic resin, a resin having both alkali-soluble performance and energy ray-curable performance is also preferable as the photosensitive coloring composition for a color filter.

Examples of the monomer constituting the thermoplastic resin include the following. For example, methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, 2-Ethylhexyl (meth) acrylate, cyclohexyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, isobornyl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) (Meta) acrylates such as acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, methoxypolypropylene glycol (meth) acrylate, or ethoxypolyethylene glycol (meth) acrylate,

Alternatively, (meth) such as (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, diacetone (meth) acrylamide, or acryloylmorpholin. Acrylamides, styrene, styrenes such as α-methylstyrene, vinyl ethers such as ethyl vinyl ethers, n-propyl vinyl ethers, isopropyl vinyl ethers, n-butyl vinyl ethers, or isobutyl vinyl ethers, vinyl acetate, or fatty acid vinyls such as vinyl propionate. Kind.

Alternatively, cyclohexylmaleimide, phenylmaleimide, methylmaleimide, ethylmaleimide, 1,2-bismaleimideethane 1,6-bismaleimidehexane, 3-maleimide propionic acid, 6,7-methylenedioxy-4-methyl-3-maleimide Kumarin, 4,4'-bismaleimidediphenylmethane, bis (3-ethyl-5-methyl-4-maleimidephenyl) methane, N, N'-1,3-phenylenedimaleimide, N, N'-1,4- Phenylened maleimide, N- (1-pyrenyl) maleimide, N- (2,4,6-trichlorophenyl) maleimide, N- (4-aminophenyl) maleimide, N- (4-nitrophenyl) maleimide, N-benzyl Maleimide, N-bromomethyl-2,3-dichloromaleimide, N-succinimidyl-3-maleimidebenzoate, N-succinimidyl-3-maleimidepropionate, N-succinimidyl-4-maleimidebutyrate, N-succinimidyl-6-maleimide Examples thereof include N-substituted maleimides such as hexanoate, N- [4- (2-benzoimidazolyl) phenyl] maleimide, and 9-maleimide acrydin.

In particular, it is preferable to have a structural unit derived from N-substituted maleimide, and among them, cyclohexylmaleimide, methylmaleimide, ethylmaleimide, and 1,2-bismaleimideethane are preferable, and cyclohexylmaleimide is particularly preferable, from the viewpoint of heat resistance.

Examples of the thermosetting resin include epoxy resin, benzoguanamine resin, rosin-modified maleic acid resin, rosin-modified fumaric acid resin, melamine resin, urea resin, and phenol resin.

When the coloring composition for a color filter of the present invention contains a thermosetting resin, it is more preferable in terms of heat resistance. For example, an epoxy resin and a melamine resin can be used more preferably, and a melamine resin is more preferable. Of these, a melamine compound having a methylol imino group or a condensate thereof is more preferable.

The thermosetting resin is preferably added in the range of 5 to 60 parts by weight with respect to 100 parts by weight of the colorant. If it is less than 10 parts by weight, the effect of improving heat resistance and light resistance becomes small, and if it exceeds 60 parts by weight, the developability at the time of alkaline development deteriorates, which is not preferable.

The weight average molecular weight (Mw) of the binder resin is preferably in the range of 5,000 to 100,000, more preferably in the range of 8,000 to 50,000 in order to preferably disperse the colorant. The number average molecular weight (Mn) is preferably in the range of 2,500 to 50,000, and the Mw / Mn value is preferably 10 or less.

Here, the weight average molecular weight (Mw) and the number average molecular weight (Mn) are determined by connecting four separation columns in series in gel permeation chromatography "HLC-8120GPC" manufactured by Tosoh Corporation, and using Tosoh stocks as fillers in order. It is a polystyrene-equivalent molecular weight measured using tetrahydrofuran as the mobile phase using "TSK-GEL SUPER H5000", "H4000", "H3000", and "H2000" manufactured by the company.

When the binder resin is used as a coloring composition for a color filter, from the viewpoint of dispersibility, developability, and heat resistance, a carboxyl group that acts as a pigment adsorbing group and an alkali-soluble group during development, a pigment carrier, and an organic solvent. The balance of the aliphatic group and the aromatic group that act as an affinity group for is important for dispersibility, developability, and durability, and it is preferable to use a resin having an acid value of 20 to 300 mgKOH / g. If the acid value is less than 20 mgKOH / g, the solubility in a developing solution is poor and it is difficult to form a fine pattern. If it exceeds 300 mgKOH / g, no fine pattern remains.

The binder resin can be used in an amount of 20 to 500% by weight based on the total weight of the coloring composition. If it is less than 30% by weight, the film forming property and various resistances are insufficient, and if it is more than 500% by weight, the pigment concentration is low and the color characteristics cannot be exhibited.

<Organic solvent>
In the coloring composition of the present invention, the pigment composition is sufficiently dispersed and permeated into the carrier, and the pigment composition is applied onto a substrate such as a glass substrate so that the dry film thickness is 0.2 to 5 μm to form a filter segment. Organic solvents can be included to facilitate this. The organic solvent is selected in consideration of the solubility of each component of the coloring composition and the safety in addition to the good cloth property of the coloring composition.

Examples of the organic solvent include ethyl lactate, benzyl alcohol, 1,2,3-trichloropropane, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane, and the like. 2-Heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexene-1-one, 3,3,5-trimethylcyclohexanone, ethyl 3-ethoxypropionate, 3-methyl -1,3
-Butandiol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, 3-methoxybutyl acetate, 4-heptanone, m-xylene, m-diethylbenzene, m -Dichlorobenzene, N, N-dimethylacetamide, N, N-dimethylformamide, n-butyl alcohol, n-butylbenzene, n-propyl acetate, o-xylene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene , P-Chlorotoluene, p-diethylbenzene, sec-butylbenzene, tert-butylbenzene, γ-butyrolactone, isobutyl alcohol, isophorone, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether , Ethylene glycol monoethyl ether acetate, ethylene glycol monotersial butyl ether, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, diisobutyl Ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone, dipropylene glycol dimethyl ether, dipropylene glycol Methyl ether acetate, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol Diacetate, propylene glycol phenyl ether, propylene glycol monoethyl ether, propylene glycol monoethyl ether Telacetate, propylene glycol monobutyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, benzyl alcohol, methyl isobutyl ketone, methylcyclohexanol, n-amyl acetate, acetic acid Examples thereof include n-butyl, isoamyl acetate, isobutyl acetate, propyl acetate and dibasic acid ester.

Among them, glycol acetates such as ethyl lactate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, and ethylene glycol monoethyl ether acetate, because the coloring composition of the present invention has good dispersion. It is preferable to use aromatic alcohols such as benzyl alcohol and ketones such as cyclohexanone.

As the organic solvent, one type can be used alone, or two or more types can be mixed and used. Further, since the solvent can adjust the coloring composition to an appropriate viscosity and form a filter segment having a desired uniform film thickness, 500 to 4000% by weight based on the total weight of the coloring composition (100% by weight). It is preferable to use the amount of.

<Dispersion aid>
When the colorant is dispersed in the carrier, a dispersion aid such as the above-mentioned pigment derivative, resin-type dispersant, or surfactant can be appropriately used. Since the dispersion aid is excellent in dispersing the colorant and has a great effect of preventing the reaggregation of the colorant after dispersion, a coloring composition obtained by dispersing the colorant in the carrier using the dispersion aid was used. In that case, a color filter having a high spectral transmittance can be obtained.

From the viewpoint of improving the dispersibility of the colorant, the amount of the dye derivative is preferably 0.5% by weight or more, more preferably 1% by weight or more, and most preferably 1% by weight or more, based on the total amount of the colorant (100% by weight). 3% by weight or more. Further, from the viewpoint of heat resistance and light resistance, it is preferably 40% by weight or less, more preferably 35% by weight or less, based on the total amount of the colorant (100% by weight).

(Resin type dispersant)
The resin-type dispersant has a pigment-affinitive moiety having a property of adsorbing to the colorant and a moiety compatible with the carrier, and has a function of adsorbing to the colorant and stabilizing dispersion on the carrier. Is. As the resin-type dispersant, an acidic resin-type dispersant is preferable, and acidic substituents, aromatic groups, etc. are block or randomly added to the main chain or end of the linear resin and the main chain or side chain of the comb-shaped resin. It is preferable to have. Specifically, polycarboxylic acid esters such as polyurethane and polyacrylate, unsaturated polyamides, polycarboxylic acids, polysiloxanes, long-chain polyaminoamide phosphates, hydroxyl group-containing polycarboxylic acid esters, modified products thereof, and poly ( An amide formed by the reaction of a lower alkyleneimine) and a polyester having a free carboxyl group, a salt thereof, or the like is used. In addition, water-soluble resins such as (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylic acid ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol, and polyvinylpyrrolidone, and water-soluble. Polymer compounds, polyesters, modified poly (meth) acrylates, ethylene oxide / propylene oxide adducts, phosphoric acid esters and the like are used. These can be used alone or in admixture of two or more, but are not necessarily limited to these.

A polymer dispersant having an acidic functional group is preferable because the viscosity of the dispersion becomes low and a high contrast is exhibited with a small amount of the dispersant added, and examples of the acidic substituent include a phosphate group and the like. Examples thereof include a sulfonic acid group and a carboxyl group. In addition, trimellitic acid and / or pyromellitic acid partially esterified are preferably used.

The resin type dispersant is preferably used in an amount of about 5 to 200% by weight, more preferably about 10 to 100% by weight, based on the total amount of the colorant.

Commercially available resin-type dispersants include Dsperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, 170 manufactured by Big Chemie Japan. , 171, 174, 180, 181, 182, 183, 184, 185, 190, 2000, 2001, 2020, 2025, 2050, 2070, 2095, 2150, 2155 or Anti-Terra-U, 203, 204, or BYK- P104, P104S, 220S, 6919, or Lactimon, Lactimon-WS or Bykuman, etc., SOLSPERSE-3000, 9000, 13000, 13240, 13650, 13940, 16000, 17000, 18000, 20000, 21000, 24000, manufactured by Japan Lubrizol. 26000, 27000, 28000, 31845, 32000, 32500, 32550, 33500, 32600, 34750, 35100, 36600, 38500, 41000, 41090, 53095, 55000, 76500, etc., BASF's EFKA-46, 47, 48, 452 4008, 4009, 4010, 4015, 4020, 4047, 4050, 4055, 4060, 4080, 4400, 4401, 4402, 4403, 4406, 4408, 4300, 4310, 4320, 4330, 4340, 450, 451, 453, 4540 , 4550, 4560, 4800, 5010, 5065, 5066, 5070, 7500, 7554, 1101, 120, 150, 1501, 1502, 1503, etc., Ajinomoto Fine Techno Co., Ltd. Ajispar PA111, PB711, PB821, PB822, PB824, etc. Can be mentioned.

(Surfactant)
Surfactants include sodium lauryl sulfate, polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium stearate, sodium alkylnaphthalin sulfonate, sodium alkyldiphenyl ether disulfonate. , Anionic surfactants such as monoethanolamine lauryl sulfate, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, monoethanolamine styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate, etc. Nonionic surfactants such as polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate, polyoxyethylene sorbitan monostearate, polyethylene glycol monolaurate, alkyl Examples thereof include chaotic surfactants such as quaternary ammonium salts and their ethylene oxide adducts, alkyl betaines such as alkyldimethylaminoacetate betaine, and amphoteric surfactants such as alkyl imidazoline, which may be used alone or in combination of two or more. They can be mixed and used, but are not necessarily limited to these.

When the resin type dispersant and the surfactant are added, the blending amount is preferably 0.1 to 55% by weight, more preferably 0.1 to 45% by weight, based on the total amount of the colorant (100% by weight). Is. When the blending amount of the resin type dispersant and the surfactant is less than 0.1% by weight, it is difficult to obtain the effect of addition, and when the blending amount is more than 55% by weight, the dispersion is adversely affected by the excessive dispersant. May exert.

<Photopolymerizable monomer>
The photopolymerizable monomer that can be added to the coloring composition for a color filter includes a monomer or an oligomer that is cured by ultraviolet rays or heat to produce a transparent resin, and these may be used alone or in combination of two or more. It can be mixed and used. The blending amount of the monomer is preferably 5 to 400% by weight based on the total weight of the colorant (100% by weight), and more preferably 10 to 300% by weight from the viewpoint of photocurability and developability. preferable.

Examples of monomers and oligomers that are cured by ultraviolet rays or heat to produce a transparent resin include methyl (meth) acrylate, ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, and 2-hydroxypropyl (meth) acrylate. , Cyclohexyl (meth) acrylate, β-carboxyethyl (meth) acrylate, polyethylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, triethylene glycol di (meth) acrylate, tripropylene glycol di ( Meta) Acrylate, Trimethylol Propanetri (Meta) Acrylate, Pentaerythritol Tri (Meta) Acrylate, Pentaerythritol Tetra (Meta) Acrylate, 1,6-Hexanediol Diglycidyl Ether Di (Meta) Acrylate, Bisphenol A Diglycidyl Etherdi (Meta) acrylate, neopentyl glycol diglycidyl ether di (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, tricyclodecanyl (meth) acrylate, ester acrylate, methylolated melamine (Meta) acrylic acid ester, epoxy (meth) acrylate, various acrylic acid esters such as urethane acrylate and methacrylic acid ester, (meth) acrylic acid, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol tri Examples thereof include vinyl ether, (meth) acrylamide, N-hydroxymethyl (meth) acrylamide, N-vinylformamide, acrylonitrile, and the like, but the present invention is not limited thereto.

<Photopolymerization initiator>
When the photosensitive coloring composition for a color filter is cured by ultraviolet irradiation to form a filter segment by a photolithography method, a photopolymerization initiator or the like is added to prepare a solvent-developed or alkali-developed colored resist material. It can be prepared in the form. When the photopolymerization initiator is used, the blending amount is preferably 2 to 200% by weight, and 5 to 150% by weight from the viewpoint of photocurability and developability, based on the total amount of the colorant. More preferred.

Examples of the photopolymerization initiator include 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl-2-hydroxy-2-methylpropan-1-one, 1-hydroxy). Cyclohexylphenylketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropa-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- Acetphenone compounds such as [4- (4-morpholinyl) phenyl] -1-butanone or 2-benzyl-2-dimethylami-1- (4-morpholinophenyl) -butane-1-one; nzoin, benzoin methyl ether , Benzoin ethyl ether, benzoin isoprol ether, or benzoin compounds such as benzyl dimethyl ketal; benzophenone benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenylbenzophenone, hydrosibenzophenone, acrylicized benzophenone, 4-benzoyl-4'-methyl Diphenisulfide, or benzophenone compounds such as 3,3', 4,4'-tetra (t-butylperoxycarbonyl) nzophenone; thioxanthone, 2-chlorthioxanthone 2-methylthioxanthone, isopropylthioxanthone, 2,4-diisopropyl Thioxanthone compounds such as thiosanton or 2,4-diethylthioxanthone; 2,46-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) --triazine, 2- (p-methoxyphenyl) ) -4,6-bis (trichloromethyl) -s triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine 2-piperonyl-4,6-bis (trichloromethyl)- s-triazine, 2,4-bis (lichloromethyl) -6-styryl-s-triazine, 2- (naphtho-1-yl) -4,6 bis (trichloromethyl) -s-triazine, 2- (4-methoxy) -Naft-1-yl) 4,6-bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl- (pipenyl) -6-triazine, or 2,4-trichloromethyl- (4'-methoxystyryl) Triazine compounds such as -6-triazine; 1,2-octanedione, 1- [4- (ferthio)-, 2- (O-benzoyloxime)], or O- (acetyl) -N -Oxym ester compounds such as (1-enyl-2-oxo-2- (4'-methoxy-naphthyl) ethylidene) hydroxylami; bis (2,4,6-trimethylbenzoyl) phenylhoffin oxide, or 2, Phosphine compounds such as 4,6-trimethylbenzoyldiphenylphosphine oxide; quinone compounds such as 9,10-phenanthrene quinone, camphorquinone, and eranthraquinone; borate compounds; carbazole compounds; midazole compounds; or Titanocene compounds and the like are used.

These photopolymerization initiators can be used alone or in admixture of two or more at any ratio as required. These photopolymerization initiators are preferably 2 to 200% by weight based on the total amount of the colorant in the coloring composition for a color filter (100% by weight), and 5 from the viewpoint of photocurability and developability. More preferably, it is ~ 150% by weight.

<Sensitizer>
Further, the photosensitive coloring composition for a color filter of the present invention may contain a sensitizer. Examples of the sensitizer include chalcone derivatives, unsaturated ketones such as dibenzalacetone, 1,2-diketone derivatives such as benzyl and camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, and anthraquinone derivatives. , Xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, oxonoal derivatives and other polymethine dyes, acrydin derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, idrin derivatives, Azulene derivative, azurenium derivative, squarylium derivative, porphyrin derivative, tetraphenylporphyrin derivative, triarylmethane derivative, tetrabenzoporphyrin derivative, tetrapyrazinoporphyrazine derivative, phthalocyanine derivative, tetraazaporphyrazine derivative, tetraquinoxalyloporphyrazine derivative , Naphthalocyanine derivative, Subphthalocyanine derivative, Pyrylium derivative, Thiopyrylium derivative, Tetraphyllin derivative, Anuren derivative, Spiropyran derivative, Spiroxazine derivative, Thiospiropirane derivative, Metal allene complex, Organic ruthenium complex, or Michler ketone derivative, α-Acyloxy ester , Acylphosphine oxide, methylphenylglycolate, benzyl, 9,10-phenanthrene quinone, camphorquinone, ethyl anthraquinone, 4,4'-diethylisophthalofenone, 3,3'or 4,4'- Examples thereof include tetra (t-butylperoxycarbonyl) benzophenone and 4,4'-diethylaminobenzophenone.

More specifically, Ogawara Nobu et al., "Dye Handbook" (1986, Kodansha), Ogawara Nobu et al., "Functional Dye Chemistry" (1981, CMC), Ikemori Chuzaburo et al., And " The sensitizers described in "Special Functional Materials" (1986, CMC) can be mentioned, but are not limited thereto. In addition, a sensitizer that absorbs light from the ultraviolet to the near infrared region can also be contained.

Two or more sensitizers may be used at an arbitrary ratio, if necessary. When the sensitizer is used, the blending amount is preferably 3 to 60% by weight based on the total weight of the photopolymerization initiator contained in the coloring composition (100% by weight), and is photocurable. From the viewpoint of developability, it is more preferably 5 to 50% by weight.

<Amine compounds>
In addition, the coloring composition for a color filter of the present invention may contain an amine compound having a function of reducing dissolved oxygen. Examples of such amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, and 2-dimethylaminobenzoate. Examples thereof include ethyl, 2-ethylhexyl 4-dimethylaminobenzoate, and N, N-dimethylparatoluidine.

<Leveling agent>
It is preferable to add a leveling agent to the coloring composition for a color filter of the present invention in order to improve the leveling property of the composition on a transparent substrate. As the leveling agent, dimethylsiloxane having a polyether structure or a polyester structure in the main chain is preferable. Specific examples of the dimethylsiloxane having a polyether structure in the main chain include FZ-2122 manufactured by Toray Dow Corning Co., Ltd. and BYK-333 manufactured by Big Chemie Co., Ltd. Specific examples of dimethylsiloxane having a polyester structure in the main chain include BYK-10 and BYK-370 manufactured by Big Chemie. Dimethylsiloxane having a polyether structure in the main chain and dimethylsiloxane having a polyester structure in the main chain can also be used in combination. The content of the leveling agent is usually preferably 0.003 to 0.5% by weight based on the total weight of the coloring composition (100% by weight).

A particularly preferable leveling agent is a kind of so-called surfactant having a hydrophobic group and a hydrophilic group in the molecule, which has a hydrophilic group but has low solubility in water, and when added to a coloring composition, the same. It is useful to have a feature of low surface tension lowering ability and good wettability to the glass plate despite low surface tension lowering ability, and the amount of addition does not cause defects in the coating film due to foaming. Those capable of sufficiently suppressing chargeability can be preferably used. As a leveling agent having such preferable properties, dimethylpolysiloxane having a polyalkylene oxide unit can be preferably used. The polyalkylene oxide unit includes a polyethylene oxide unit and a polypropylene oxide unit, and dimethylpolysiloxane may have both a polyethylene oxide unit and a polypropylene oxide unit.

In addition, the bonding form of the polyalkylene oxide unit with dimethylpolysiloxane includes a pendant type in which the polyalkylene oxide unit is bonded in the repeating unit of dimethylpolysiloxane, a terminal-modified type in which the polyalkylene oxide unit is bonded to the terminal of dimethylpolysiloxane, and dimethylpolysiloxane. It may be any of the linear block copolymer types that are alternately and repeatedly bonded. Didimethylpolysiloxane having a polyalkylene oxide unit is commercially available from Toray Dow Corning Co., Ltd., for example, FZ-2110, FZ-2122, FZ-2130, FZ-2166, FZ-2191, FZ-2203, FZ. 2207, but is not limited to these.

It is also possible to supplementally add anionic, cationic, nonionic, or amphoteric surfactants to the leveling agent. Two or more kinds of surfactants may be mixed and used.

Anionic surfactants to be added as an auxiliary to the leveling agent include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkylnaphthalin sulfonate, and alkyldiphenyl ether disulfonic acid. Sodium, monoethanolamine lauryl sulfate, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate Examples include ester.

Examples of the chaotic surfactant added as a supplement to the leveling agent include alkyl quaternary ammonium salts and their ethylene oxide adducts. Nonionic surfactants to be added to the leveling agent include polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate, and polyoxyethylene sorbitan monostearate. , Polyethylene glycol monolaurate and the like; alkyl betaines such as alkyldimethylaminoacetic acid betaine, amphoteric surfactants such as alkyl imidazoline, and fluorine-based and silicone-based surfactants.

<Curing agent / curing accelerator>
Further, the coloring composition for a color filter of the present invention may contain a curing agent, a curing accelerator, or the like, if necessary, in order to assist the curing of the thermosetting resin. As the curing agent, phenol-based resins, amine-based compounds, acid anhydrides, active esters, carboxylic acid-based compounds, sulfonic acid-based compounds and the like are effective, but the curing agent is not particularly limited to these, and is a thermosetting resin. Any curing agent may be used as long as it can react with. Further, among these, a compound having two or more phenolic hydroxyl groups in one molecule and an amine-based curing agent are preferably mentioned. Examples of the curing accelerator include amine compounds (for example, dicyandiamide, benzyldimethylamine, 4- (dimethylamino) -N, N-dimethylbenzylamine, 4-methoxy-N, N-dimethylbenzylamine, 4-methyl). -N, N-dimethylbenzylamine, etc.), quaternary ammonium salt compounds (eg, triethylbenzylammonium chloride, etc.), blocked isocyanate compounds (eg, dimethylamine, etc.), imidazole derivative bicyclic amidin compounds and salts thereof (eg, eg) Imidazole, 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 4-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, 1- (2-cyanoethyl) -2- Ethyl-4-methylimidazole, etc.), phosphorus compounds (eg, triphenylphosphine, etc.), guanamine compounds (eg, melamine, guanamine, acetoguanamine, benzoguanamine, etc.), S-triazine derivatives (eg, 2,4-diamino-6) -Methacryloxyethyl-S-triazine, 2-vinyl-2,4-diamino-S-triazine, 2-vinyl-4,6-diamino-S-triazine isocyanuric acid adduct, 2,4-diamino-6- Methacryloyloxyethyl-S-triazine, isocyanuric acid adduct, etc.) can be used. These may be used alone or in combination of two or more. The content of the curing accelerator is preferably 0.01 to 15% by weight with respect to the total amount of the thermosetting resin.

<Other colorants>
The coloring composition for a color filter of the present invention contains the pigment composition of the present invention as a colorant, but a pigment composition such as another pigment or dye as long as the effect of the present invention is not impaired for the purpose of adjusting the chromaticity or the like. You may use the thing together. The colorants that may be used in combination will be described below.

For example, C.I. I. Pigment Red 7, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 57: 1, 81, 81: 1, 81: 2, 81: 3, 81: 4, 122, 146, 168, 169, 176, 177, 178, 179, 184, 185, 187, 200, 202, 208, 210, 242, 246, 254, 255, 264, 270, 272, 273, 274, 276, 277, 278, Red pigments such as 279, 280, 281, 282, 283, 284, 285, 286, or 287 can be mentioned. Examples of the red dye include xanthene type, azo type (pyridone type, barbituric acid type, metal complex type, etc.), disazo type, anthraquinone type and the like. Specifically, C.I. I. Examples thereof include salt-forming compounds of xanthene-based acid dyes such as Acid Red 52, 87, 92, 289 and 338.

In addition, C.I. I. Pigment Orange 43, 71, or 73 and / or other orange pigments and / or C.I. I. Pigment Yellow 1,2,3,4,5,6,10,12,13,14,15,16,17,18,24,31,32,34,35,35: 1,36,36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, Yellow pigments such as 193, 194, 198, 199, 213, 214, 218, 219, 220, or 221 can be used in combination. Examples of orange dyes and / or yellow dyes include quinoline dyes, azo dyes (pyridone dyes, barbituric acid dyes, metal complex dyes, etc.), disazo dyes, and methine dyes.

From the viewpoint of brightness, preferred dyes to be used in combination include azo-based, naphthol-azo-based, diketopyrrolopyrrole-based, anthraquinone-based, and quinophthalone-based dyes. Specifically, C.I. I. Pigment Red 176, 177, 254, 242, C.I. I. Pigment Yellow 138, 150, brominated diketopyrrolopyrrole pigments. Among these, particularly preferable dyes are C.I. I. Pigment Red 254, C.I. I. Pigment Red 242, and a brominated diketopyrrolopyrrole pigment.

When the above other dyes are used in combination with the pigment composition of the present invention, the pigment composition of the present invention is preferably in the range of 10% by weight to 100% by weight in the total amount of the colorant (100% by weight). More preferably, it is in the range of 30% by weight to 100% by weight.

<Other additive components>
The coloring composition for a color filter of the present invention may contain a storage stabilizer in order to stabilize the viscosity of the composition over time. Further, an adhesion improver such as a silane coupling agent can be contained in order to enhance the adhesion with the transparent substrate.

Examples of the storage stabilizer include quaternary ammonium chlorides such as benzyltrimethyl chloride and diethylhydroxyamine, organic acids such as lactic acid and oxalic acid and their methyl ethers, t-butylpyrocatechol, tetraethylphosphine, tetraphenylphosphine and the like. Examples thereof include organic phosphine and phosphite. The storage stabilizer can be used in an amount of 0.1 to 10% by weight based on the total amount of the colorant (100% by weight).

Adhesion improvers include vinylsilanes such as vinyltris (β-methoxyethoxy) silane, vinylethoxysilane and vinyltrimethoxysilane, (meth) acrylic silanes such as γ-methacryloxypropyltrimethoxysilane, and β- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, β- (3,4-epoxycyclohexyl) methyltrimethoxysilane, β- (3,4-epoxycyclohexyl) ethyltriethoxysilane, β- (3,4-epoxycyclohexyl) Epoxysilanes such as methyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, N-β (aminoethyl) γ-aminopropyltrimethoxysilane, N-β (amino) Ethyl) γ-aminopropyltriethoxysilane, N-β (aminoethyl) γ-aminopropylmethyldiethoxysisilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, N-phenyl-γ-amino Examples thereof include aminosilanes such as propyltrimethoxysilane and N-phenyl-γ-aminopropyltriethoxysilane, and silane coupling agents such as thiosilanes such as γ-mercaptopropyltrimethoxysilane and γ-mercaptopropyltriethoxysilane. The adhesion improver can be used in an amount of 0.01 to 10% by weight, preferably 0.05 to 5% by weight, based on the total amount of the colorant in the coloring composition (100% by weight).

<Manufacturing method of coloring composition for color filter>
The coloring composition of the present invention is a mixture of a pigment composition agent, a binder resin, an organic solvent, and other dispersion aids, and various dispersers such as a three-roll mill, a two-roll mill, a sand mill, a kneader, and an attritor. Can be dispersed and manufactured using. Further, the coloring composition of the present invention can also be produced by mixing colorants separately dispersed in a binder resin and an organic solvent.

When the colorant is dispersed in the binder resin using a disperser in this way, the dispersed particle size becomes smaller as the dispersion progresses, the transparency increases, and the contrast ratio increases. Therefore, the smaller the dispersed particle size is, the better. Therefore, good characteristics can be obtained from about 300 nm. On the other hand, as the dispersion progresses and the dispersed particle size becomes smaller, the viscosity of the dispersion tends to increase and the thixotropic property tends to increase. When used as a photosensitive coloring composition for a color filter, it is required to be thin-film coated and the surface of the coating film to be smooth, so that it is required to have a low viscosity and a Neutonian flow. Therefore, in consideration of the viscosity and thixotropic property preferable for normal use, it is preferable to suppress the dispersed particle size to about 100 nm. In this way, by using a colorant having an average primary particle size of 100 nm or less and controlling the degree of dispersion so that the average particle size of the dispersed particles is within the range of 50 nm to 150 nm, the viscosity increase and thixotropic property are minimized. It is suppressed to the limit, and a good pigment dispersion can be obtained.

<Removal of coarse particles>
The coloring composition for a color filter is obtained by centrifugation or filtration using a sintering filter, a membrane filter, or the like to obtain coarse particles of 5 μm or more, preferably coarse particles of 1 μm or more, and more preferably 0.5 μm or more. And it is preferable to remove the mixed dust. As described above, it is preferable that the coloring composition does not substantially contain particles of 0.5 μm or more. More preferably, it does not contain particles of 0.3 μm or less.

<Color filter>
Next, the color filter of the present invention will be described. The color filter includes a filter segment formed by using the coloring composition for a color filter. Examples of the color filter include those including a red filter segment, a green filter segment, and a blue filter segment. The filter segment is coated with a coloring composition for a color filter by a spin coating method or a die coating method, and then ultraviolet rays or the like. It is formed on the substrate by irradiating the active energy ray of No. 1 to cure the portion to be the filter segment and then developing it. The red filter segment in the red filter segment is formed from a coloring composition or a photosensitive coloring composition containing the coloring agent of the present invention.

The green filter segment can be formed by using a conventional green coloring composition containing a green pigment and a pigment carrier or a green photosensitive coloring composition. Examples of the green pigment include C.I. I. Pigment Green 7, 10, 36, 37, 58 and the like are used. In addition, blue pigments such as aluminum phthalocyanine can also be used.

Further, a yellow pigment can be used in combination with the green coloring composition or the green photosensitive coloring composition. Examples of the yellow pigment that can be used in combination include C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, Yellow pigments such as 193, 194, 198, 199, 213, 214, 218, 219, 220, or 221 can be mentioned. It is also possible to use a salt-forming compound of a basic dye or an acid dye that exhibits yellow color in combination.

The blue filter segment can be formed by using a conventional blue coloring composition containing a blue pigment and a pigment carrier or a blue photosensitive coloring composition. Examples of the blue pigment include C.I. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64 and the like are used. Further, a purple pigment can be used in combination with the blue coloring composition or the blue photosensitive coloring composition. Examples of the purple pigment that can be used in combination include C.I. I. Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, 50 and other purple pigments can be mentioned. Further, a salt-forming compound of a basic dye or an acid dye exhibiting blue or purple can also be used. When a dye is used, a xanthene dye is preferable in terms of heat resistance and brightness.

<Manufacturing method of color filter>
The color filter can be manufactured by a printing method or a photolithography method. The formation of the filter segment by the printing method can be patterned only by repeating printing and drying of the coloring composition prepared as the printing ink, and therefore, as a manufacturing method of the color filter, it is excellent in mass productivity at low cost. Furthermore, with the development of printing technology, it is possible to print fine patterns having high dimensional accuracy and smoothness. In order to perform printing, it is preferable that the composition is such that the ink does not dry or solidify on the printing plate or on the blanket. It is also important to control the fluidity of the ink on the printing machine, and the viscosity of the ink can be adjusted with a dispersant or an extender pigment.

When the filter segment is formed by the photolithography method, the coloring composition prepared as the solvent-developing type or alkali-development type colored resist material is applied onto a transparent substrate by coating a play coat, a spin coat, a slit coat, a roll coat, or the like. By the method, the coating is applied so that the dry film thickness is 0.2 to 5 μm. If necessary, the dried film is exposed to ultraviolet rays through a mask having a predetermined pattern provided in contact with or without contact with the film. Then, after immersing in a solvent or an alkaline developer or spraying the developer with a spray or the like to remove the uncured portion to form a desired pattern, the same operation is repeated for other colors to manufacture a color filter. be able to. Further, in order to promote the polymerization of the colored resist material, heating can be applied as needed. According to the photolithography method, a color filter having higher accuracy than the above printing method can be manufactured.

At the time of development, an aqueous solution of sodium carbonate, sodium hydroxide or the like is used as the alkaline developer, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used. Further, an antifoaming agent or a surfactant can be added to the developing solution. In order to increase the ultraviolet exposure sensitivity, the colored resist was applied and dried, and then a water-soluble or alkaline water-soluble resin such as polyvinyl alcohol or a water-soluble acrylic resin was applied and dried to form a film for preventing polymerization inhibition by oxygen. Later, UV exposure can also be performed.

The color filter of the present invention can be produced by an electrodeposition method, a transfer method or the like in addition to the above methods, but the coloring composition or the photosensitive coloring composition of the present invention can be used in any method. The electrodeposition method is a method of manufacturing a color filter by electrodepositing each color filter segment on the transparent conductive film by electrophoresis of colloidal particles using the transparent conductive film formed on the substrate. .. Further, the transfer method is a method in which a filter segment is formed in advance on the surface of a peelable transfer base sheet, and the filter segment is transferred to a desired substrate.

Before forming each color filter segment on the transparent substrate or the reflective substrate, a black matrix can be formed in advance. As the black matrix, a multilayer film of chromium or chromium / chromium oxide, an inorganic film such as titanium nitride, or a resin film in which a light-shielding agent is dispersed is used, but the black matrix is not limited thereto. It is also possible to form a thin film transistor (TFT) on the transparent substrate or the reflective substrate in advance, and then form each color filter segment. Further, an overcoat film, a transparent conductive film, or the like is formed on the color filter of the present invention, if necessary.

Hereinafter, the present invention will be described based on examples, but the present invention is not limited thereto. In the examples, unless otherwise specified, "parts" and "%" represent "parts by mass" and "% by mass", respectively.

(Polymerization average molecular weight of resin (Mw))
A method for calculating the weight average molecular weight (Mw) of the resin type dispersant and the binder resin will be described.

In the gel permeation chromatography "HLC-8120GPC" manufactured by Tosoh Corporation, four separation columns are connected in series, and the fillers are "TSK-GEL SUPER H5000", "H4000", "H3000" manufactured by Tosoh Corporation in order. , And "H2000", and polystyrene-equivalent molecular weight measured using tetrahydrofuran as the mobile phase.

(Acid value of resin)
80 ml of acetone and 10 ml of water are added to 0.5 to 1.0 part of the resin solution and stirred to uniformly dissolve the solution. Using a 0.1 mol / L KOH aqueous solution as a titrator, an automatic titrator (“COM-555”” The acid value of the resin solution was measured by titration using (manufactured by Hiranuma Sangyo). Then, the acid value per solid content of the resin was calculated from the acid value of the resin solution and the solid content concentration of the resin solution.

(Method for identifying azo pigments (A1, A2, A3))
An LC-MS spectrum was used to identify the azo pigments (A1, A2, A3) used in the present invention. The measurement of the LC-MS spectrum was performed under the following conditions.

Equipment: UPLC H-Class / XevoTQD manufactured by Japan Waters Corp.
Column: Symmetry C185 micron (Japan Waters Corp.)
Eluent:
(A) H ₂ O
(B) DMF
Eluent conditions: (A): (B) = 10:90 (volume ratio)
Flow velocity: 0.400 ml / min Injection volume: 1 μl
Column temperature: 40 ° C
Measurement wavelength: 300 nm

The obtained compound was identified based on the agreement between the molecular ion peak of the obtained mass spectrum and the mass number obtained by calculation. Further, in the chromatogram obtained at the measurement wavelength under the above conditions, the sum of the area ratio of the peaks of the azo pigment (A1) having two bases bonded to the peaks of the azo pigment (A2 or A3) having one base bonded. From the area ratio, the mass ratio of (A1) and (A2 or A3) was calculated.

<Manufacturing method of dispersant>
(Preparation of Dispersant 1)
60 parts of ethyl acrylate (EA), 40 parts of t-butyl acrylate (t-BA), 90 parts of methyl methacrylate (MMA), methacrylic acid (MAA) in a reaction vessel equipped with a gas introduction tube, a thermometer, a condenser, and a stirrer. 10 parts were charged and replaced with nitrogen gas. The inside of the reaction vessel was heated to 80 ° C., 44 parts of 1,3-dimercapto-2-propanol was added, and the reaction was carried out for 12 hours. It was confirmed by solid content measurement that 95% had reacted. Next, 19 parts of pyromellitic anhydride, 231 parts of cyclohexanone, and 0.40 parts of 1,8-diazabicyclo- [5.4.0] -7-undecene as a catalyst were charged and reacted at 120 ° C. for 7 hours. It was confirmed by measuring the acid value that 98% or more of the acid anhydride was half-esterified, and the reaction was terminated. PGMAc was added to prepare a non-volatile content of 50% to obtain Dispersant 1 having an acid value of 70 and a weight average molecular weight of 10000.

<Manufacturing method of binder resin solution>
(Preparation of acrylic resin solution 1)
196 parts of cyclohexanone was charged into a reaction vessel equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, a dropping tube and a stirrer in a separable 4-neck flask, the temperature was raised to 80 ° C., the inside of the reaction vessel was replaced with nitrogen, and then dropped. From the tube, 37.2 parts of n-butyl methacrylate, 12.9 parts of 2-hydroxyethyl methacrylate, 12.0 parts of methacrylate, paracumylphenol ethylene oxide-modified acrylate (“Aronix M110” manufactured by Toa Synthetic Co., Ltd.) 20.7 A mixture of 1.1 parts of 2,2'-azobisisobutyronitrile was added dropwise over 2 hours. After completion of the dropping, the reaction was continued for another 3 hours to obtain a solution of acrylic resin. After cooling to room temperature, about 2 parts of the resin solution is sampled and dried by heating at 180 ° C. for 20 minutes to measure the non-volatile content, and methoxypropyl acetate is added to the previously synthesized resin solution so that the non-volatile content is 20%. Acrylic resin solution 1 was prepared by addition. The weight average molecular weight (Mw) was 26000.

(Preparation of acrylic resin solution 2)
207 parts of cyclohexanone was placed in a reaction vessel equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, a dropping tube and a stirrer in a separable 4-neck flask, the temperature was raised to 80 ° C., the inside of the reaction vessel was replaced with nitrogen, and then dropped. From the tube, 20 parts of methacrylic acid, 20 parts of paracumylphenol ethylene oxide-modified acrylate (Aronix M110 manufactured by Toa Synthetic Co., Ltd.), 45 parts of methyl methacrylate, 8.5 parts of 2-hydroxyethyl methacrylate, and 2,2'-azobis. A mixture of 1.33 parts of isobutyronitrile was added dropwise over 2 hours. After completion of the dropping, the reaction was continued for another 3 hours to obtain a copolymer resin solution. Next, with respect to the total amount of the obtained copolymer solution, nitrogen gas was stopped, dry air was injected for 1 hour, and the mixture was stirred, cooled to room temperature, and then 2-methacryloyloxyethyl isocyanate (Karens manufactured by Showa Denko Co., Ltd.). A mixture of 6.5 parts of MOI), 0.08 part of dibutyltin laurate and 26 parts of cyclohexanone was added dropwise at 70 ° C. over 3 hours. After completion of the dropping, the reaction was continued for another 1 hour to obtain a solution of acrylic resin. After cooling to room temperature, about 2 parts of the resin solution is sampled and dried by heating at 180 ° C. for 20 minutes to measure the non-volatile content, and cyclohexanone is added to the previously synthesized resin solution so that the non-volatile content becomes 20%. Acrylic resin solution 2 was prepared. The weight average molecular weight (Mw) was 18,000.

<Method for producing a pigment composition for a color filter containing an azo pigment (A1) and an azo pigment (A2)>
The specific method for synthesizing the pigment composition containing the azo pigment (A1) and the azo pigment (A2) is shown below. Other azo pigments according to the present invention can also be synthesized according to a similar scheme.

<Manufacturing method of Ginaftol>
Prior to the synthesis of the azo pigment 1, a method for synthesizing dinaphthol 1 will be described.
The specific method for synthesizing dinaphthol 1 is shown below. Other dinaphthols according to the present invention can also be synthesized according to a similar scheme.

[Manufacturing Example 1] (Manufacturing of Ginaftol 1)
After adding 200 parts of 2-hydroxy-3-naphthoic acid to 1500 parts of tetrahydrofuran (THF), 164 parts of thionyl chloride was added, and the mixture was stirred at room temperature for 2 hours to prepare a 2-hydroxy-3-naphthoic acid chloride solution. Separately, 52 parts of the p-phenylenediamine part was added to 1500 parts of tetrahydrofuran (THF), and the mixture was stirred for 30 minutes while maintaining the temperature at 0 to 5 ° C. The prepared 2-hydroxy-3-naphthoic acid chloride solution was added dropwise thereto over 30 minutes, and after the addition, the mixture was stirred at room temperature for 2 hours. After adding 3000 parts of warm water, the precipitated product was filtered and tetrahydrofuran (THF) was washed with boiling water. The removed wet cake was dried to obtain 200 parts (yield: 93.4%) of dinaphthol 1.

[Production Examples 2 to 14] (Production of Ginaftol 2 to 14)
As shown in Table 2 below, the same operations as in Production Example 1 were carried out except that the type of diamine and the amount charged were changed, and dinaphthols 2 to 14 were obtained with the yields and yields shown in Table 2 below.

<Manufacturing method of pigment compositions for color filters (A1 and A2)>
[Example 1] (Production of red colorant (RP-1))
After adding 89 parts of 3-amino-4-methoxybenzamide to 1730 parts of N-methyl-2-pyrrolidone (NMP), 182 parts of 35% hydrochloric acid was added, and the mixture was cooled to -2 to 0 ° C. After adding 134 parts of a 25% aqueous sodium nitrite solution to this solution, the mixture was stirred for 2 hours while maintaining the temperature at 0 to 5 ° C. to prepare a diazonium solution. Separately, a coupler solution consisting of 120 parts of dinaphthol 1, 221 parts of 25% sodium hydroxide solution, 1640 parts of N-methyl-2-pyrrolidone (NMP) and 490 parts of methanol was prepared. To the prepared diazonium solution, 1585 parts of an acetate buffer solution having a pH of 5.4 was added dropwise, and then the prepared coupler solution was added dropwise over 40 minutes. After completion of the dropping, the mixture was stirred at room temperature for 30 minutes and then kept at 60 ° C. After adding 2000 parts of warm water, the precipitated product was filtered, and N-methyl-2-pyrrolidone (NMP) and methanol were washed with boiling water. 4000 parts of water was added to the removed wet cake, and the mixture was stirred for 2 hours while maintaining the temperature at 80 ° C. After stirring, the reslurry solution was filtered, washed with boiling water, and dried to obtain 201 parts (yield: 96.2%) of azo pigment 1 (mixture of A1-1 and A2-1). As a result of LC-MS spectrum measurement, the content of A2-1 was 2.0% by mass.

Next, 150 parts of the azo pigment 1, 1500 parts of sodium chloride, and 300 parts of diethylene glycol were charged in a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.), kneaded at 70 ° C. for 8 hours, and subjected to salt milling treatment. The obtained kneaded product was put into 5000 parts of warm water, stirred for 1 hour while heating at 70 ° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. for 24 hours. 138 parts of red colorant (RP-1) was obtained.

[Example 2] (Production of red colorant (RP-2))
The same operation as in Example 1 was performed except that 128 parts of dinaphthol 2 was used instead of 120 parts of dinaphthol 1 used in Example 1, and 210 parts of azo pigment 2 (mixture of A1-2 and A2-2) was used. (Yield: 97.0%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-2 was 2.0% by mass. Next, 138 parts of a red colorant (RP-2) was obtained by performing the same operation as in Example 1 except that the azo pigment 2 was used instead of the azo pigment 1 used in Example 1.

[Example 3] (Production of red colorant (RP-3))
The same operation as in Example 1 was performed except that 124 parts of dinaphthol 3 was used instead of 120 parts of dinaphthol 1 used in Example 1, and 210 parts of azo pigment 2 (mixture of A1-3 and A2-3) was used. (Yield: 98.5%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-3 was 2.0% by mass, and A2-3 was a mixture of A2-3a and A2-3b. Next, 138 parts of a red colorant (RP-3) was obtained by performing the same operation as in Example 1 except that the azo pigment 3 was used instead of the azo pigment 1 used in Example 1.

[Example 4] (Production of red colorant (RP-4))
The same operation as in Example 1 was performed except that 133 parts of dinaphthol 4 was used instead of 120 parts of dinaphthol 1 used in Example 1, and 213 parts of azo pigment 4 (mixture of A1-4 and A2-4) was used. (Yield: 96.5%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-4 was 2.0% by mass, and A2-4 was a mixture of A2-4a and A2-4b. Next, 138 parts of a red colorant (RP-4) was obtained by performing the same operation as in Example 1 except that the azo pigment 4 was used instead of the azo pigment 1 used in Example 1.

[Example 5] (Production of red colorant (RP-5))
The same operation as in Example 1 was performed except that 133 parts of dinaphthol 5 was used instead of 120 parts of dinaphthol 1 used in Example 1, and 225 parts of azo pigment 5 (mixture of A1-5 and A2-5) was used. (Yield: 98.5%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-5 was 2.0% by mass. Next, 138 parts of a red colorant (RP-5) was obtained by performing the same operation as in Example 1 except that the azo pigment 5 was used instead of the azo pigment 1 used in Example 1.

[Example 6] (Production of red colorant (RP-6))
The same operation as in Example 1 was performed except that 129 parts of dinaphthol 6 was used instead of 120 parts of dinaphthol 1 used in Example 1, and 211 parts of azo pigment 6 (mixture of A1-6 and A2-6) was used. (Yield: 97.0%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-6 was 2.0% by mass, and A2-6 was a mixture of A2-6a and A6-3b. Next, 138 parts of a red colorant (RP-6) was obtained by performing the same operation as in Example 1 except that the azo pigment 6 was used instead of the azo pigment 1 used in Example 1.

[Example 7] (Production of red colorant (RP-7))
The same operation as in Example 1 was performed except that 137 parts of dinaphthol 7 was used instead of 120 parts of dinaphthol 1 used in Example 1, and 219 parts of azo pigment 7 (mixture of A1-7 and A2-7) was used. (Yield: 97.0%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-7 was 2.0% by mass, and A2-7 was a mixture of A2-7a and A2-7b. Next, 138 parts of a red colorant (RP-7) was obtained by performing the same operation as in Example 1 except that the azo pigment 7 was used instead of the azo pigment 1 used in Example 1.

[Example 8] (Production of red colorant (RP-8))
The same operation as in Example 1 was performed except that 136 parts of dinaphthol 8 was used instead of 120 parts of dinaphthol 1 used in Example 1, and 215 parts of azo pigment 8 (mixture of A1-8 and A2-8) was used. (Yield: 96.5%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-8 was 2.0% by mass. Next, 138 parts of a red colorant (RP-8) was obtained by performing the same operation as in Example 1 except that the azo pigment 8 was used instead of the azo pigment 1 used in Example 1.

[Example 9] (Production of red colorant (RP-9))
The same operation as in Example 1 was performed except that 148 parts of dinaphthol 9 was used instead of 120 parts of dinaphthol 1 used in Example 1, and 229 parts of azo pigment 9 (mixture of A1-9 and A2-9) was used. (Yield: 96.5%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-9 was 2.0% by mass, and A2-9 was a mixture of A2-9a and A2-9b. Next, 138 parts of a red colorant (RP-9) was obtained by performing the same operation as in Example 1 except that the azo pigment 9 was used instead of the azo pigment 1 used in Example 1.

[Example 10] (Production of red colorant (RP-10))
The same operation as in Example 1 was performed except that 138 parts of dinaphthol 10 was used instead of 120 parts of dinaphthol 1 used in Example 1, and 216 parts of azo pigment 10 (mixture of A1-10 and A2-10) was used. (Yield: 95.0%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-10 was 2.0% by mass, and A2-10 was a mixture of A2-10a and A2-10b. Next, 138 parts of a red colorant (RP-10) was obtained by performing the same operation as in Example 1 except that the azo pigment 10 was used instead of the azo pigment 1 used in Example 1.

[Example 11] (Production of red colorant (RP-11))
The same operation as in Example 1 was performed except that 132 parts of dinaphthol 11 was used instead of 120 parts of dinaphthol 1 used in Example 1, and 211 parts of azo pigment 11 (mixture of A1-11 and A2-11) was used. (Yield: 95.5%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-11 was 2.0% by mass, and A2-11 was a mixture of A2-11a and A2-11b. Next, 138 parts of a red colorant (RP-11) was obtained by performing the same operation as in Example 1 except that the azo pigment 11 was used instead of the azo pigment 1 used in Example 1.

[Example 12] (Production of red colorant (RP-12))
The same operation as in Example 1 was performed except that 127 parts of dinaphthol 12 was used instead of 120 parts of dinaphthol 1 used in Example 1, and 211 parts of azo pigment 12 (mixture of A1-12 and A2-12) was used. (Yield: 97.8%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-12 was 2.0% by mass, and A2-12 was a mixture of A2-12a and A2-12b. Next, 138 parts of a red colorant (RP-12) was obtained by performing the same operation as in Example 1 except that the azo pigment 12 was used instead of the azo pigment 1 used in Example 1.

[Example 13] (Production of red colorant (RP-13))
Examples except that 89 parts of 3-amino-4-methoxybenzanilide was used instead of 89 parts of 3-amino-4-methoxybenzamide used in Example 1 and 120 parts of dinaphthol 1 was changed to 82 parts. The same operation as in 1 was carried out to obtain 168 parts (yield: 98.2%) of azo pigment 13 (mixture of A1-13 and A2-13). As a result of LC-MS spectrum measurement, the content of A2-13 was 2.0% by mass. Next, 138 parts of a red colorant (RP-13) was obtained by performing the same operation as in Example 1 except that the azo pigment 13 was used instead of the azo pigment 1 used in Example 1.

[Example 14] (Production of red colorant (RP-14))
The same operation as in Example 13 was performed except that 287 parts of dinaphthol was used instead of 182 parts of dinaphthol used in Example 13, and 185 parts of azo pigment 14 (mixture of A1-14 and A2-14) was used. (Yield: 98.0%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-14 was 2.0% by mass. Next, 138 parts of a red colorant (RP-14) was obtained by performing the same operation as in Example 1 except that the azo pigment 14 was used instead of the azo pigment 1 used in Example 1.

[Example 15] (Production of red colorant (RP-15))
The same operation as in Example 13 was carried out except that 93 parts of dinaphthol 8 was used instead of 82 parts of dinaphthol used in Example 13, and 193 parts of azo pigment 15 (mixture of A1-15 and A2-15) was used. (Yield: 97.8%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-15 was 2.0% by mass. Next, 138 parts of a red colorant (RP-15) was obtained by performing the same operation as in Example 1 except that the azo pigment 15 was used instead of the azo pigment 1 used in Example 1.

[Example 16] (Production of red colorant (RP-16))
The same operation as in Example 13 was carried out except that 111 parts of dinaphthol 13 was used instead of 82 parts of dinaphthol used in Example 13, and 210 parts of azo pigment 16 (mixture of A1-16 and A2-16). (Yield: 97.0%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-16 was 2.0% by mass. Next, 138 parts of a red colorant (RP-16) was obtained by performing the same operation as in Example 1 except that the azo pigment 16 was used instead of the azo pigment 1 used in Example 1.

[Example 17] (Production of red colorant (RP-17))
The same operation as in Example 13 was carried out except that 88 parts of dinaphthol 14 were used instead of 82 parts of dinaphthol used in Example 13, and 155 parts of azo pigment 17 (mixture of A1-17 and A2-17) was used. (Yield: 96.2%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-17 was 2.0% by mass. Next, 138 parts of a red colorant (RP-17) was obtained by performing the same operation as in Example 1 except that the azo pigment 17 was used instead of the azo pigment 1 used in Example 1.

[Example 18] (Production of red colorant (RP-18))
The same operation as in Example 13 was performed except that 95 parts of dinaphthol was used instead of 82 parts of dinaphthol used in Example 13, and 166 parts of azo pigment 18 (mixture of A1-18 and A2-18) was used. (Yield: 97.9%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-18 was 2.0% by mass. Next, 138 parts of a red colorant (RP-18) was obtained by performing the same operation as in Example 1 except that the azo pigment 18 was used instead of the azo pigment 1 used in Example 1.

[Example 19] (Production of red colorant (RP-19))
The same operation as in Example 18 was carried out except that 95 parts of dinaphthol 5 used in Example 18 was changed to 105 parts, and 161 parts of azo pigment 19 (mixture of A1-18 and A2-18) (yield: 94). 0.7%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-18 was 10.0% by mass. Next, 138 parts of a red colorant (RP-19) was obtained by performing the same operation as in Example 1 except that the azo pigment 19 was used instead of the azo pigment 1 used in Example 1.

[Example 20] (Production of red colorant (RP-20))
The same operation as in Example 18 was carried out except that 95 parts of dinaphthol 5 used in Example 18 was changed to 114 parts, and 158 parts of azo pigment 20 (mixture of A1-18 and A2-18) (yield: 92). 9.9%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-18 was 20.0% by mass. Next, 138 parts of a red colorant (RP-20) was obtained by performing the same operation as in Example 1 except that the azo pigment 20 was used instead of the azo pigment 1 used in Example 1.

<Manufacturing method of pigment compositions for color filters (A1 and A3)>
The specific method for synthesizing the pigment composition containing the azo pigment (A1) and the azo pigment (A3) is shown below. Other azo pigments according to the present invention can also be synthesized according to a similar scheme.

[Example 21] (Production of red colorant (RP-21))
After adding 135 parts of 4-methoxy-3-amino-benzanilide to 1500 parts of water, 221 parts of 35% hydrochloric acid was added, and the mixture was cooled to -2 to 0 ° C. After adding 156 parts of a 25% aqueous sodium nitrite solution to this solution, the mixture was stirred for 30 minutes while maintaining the temperature at 0 to 5 ° C. to prepare a diazonium solution. Separately, a coupler solution consisting of 105 parts of 2,3-hydroxynaphthoic acid, 237 parts of 25% sodium hydroxide solution, and 1500 parts of water was prepared. The prepared diazonium solution and coupler solution were simultaneously added dropwise to 3000 parts of an acetate buffer solution having a pH of 5.4 over 10 minutes. After completion of the dropping, the mixture is stirred at room temperature for 30 minutes, further stirred while maintaining at 80 ° C., the precipitated reactant is filtered, washed with boiling water, dried and dried, and the azo compound represented by the following formula (23) is formed. a 198 parts (yield: 98.0%) was obtained.

To 1350 parts of N-methyl-2-pyrrolidone (NMP), 183 parts of the azo compound a represented by the following formula (23) and 15 parts of N, N-dimethylformamide are added, heated to 85 ° C., and then 63 parts of thionyl chloride. Was added dropwise over 30 minutes. After completion of the dropping, the mixture was refluxed for 2 hours. The above reaction solution was added dropwise to a solution prepared separately by heating 35 parts of 2,5-dichloro-1,4-phenylenediamine and 2250 parts of N-methyl-2-pyrrolidone (NMP) to 85 ° C. over 1 hour. The mixture was heated under reflux for 4 hours. After cooling this reaction solution to 95 ° C., 30 parts of a 28% aqueous ammonia solution and 30 parts of water are added, the mixture is stirred at 95 to 100 ° C. for 30 minutes, and the precipitated reaction is filtered to obtain N-methyl-2-pyrrolidone ( After washing with NMP), methanol, and boiling water, it was dried to obtain 179 parts (yield: 89.1%) of azo pigment 21 (mixture of A1-18 and A3-18). As a result of LC-MS spectrum measurement, the content of A3-18 was 2.0% by mass.

Equation (23)

Next, 138 parts of a red colorant (RP-21) was obtained by performing the same operation as in Example 1 except that the azo pigment 21 was used instead of the azo pigment 1 used in Example 1.

[Example 22] (Production of red colorant (RP-22))
The same operation as in Example 21 was carried out except that 95 parts of 2,5-dichloro-1,4-phenylenediamine used in Example 21 was changed to 105 parts, and the azo pigments 22 (A1-18 and A3-18) were carried out. 173 parts (yield: 86.1%) of the mixture was obtained. As a result of LC-MS spectrum measurement, the content of A2-18 was 10.0% by mass. Next, 138 parts of a red colorant (RP-22) was obtained by performing the same operation as in Example 1 except that the azo pigment 22 was used instead of the azo pigment 1 used in Example 1.

[Example 23] (Production of red colorant (RP-23))
The same operation as in Example 21 was carried out except that 95 parts of 2,5-dichloro-1,4-phenylenediamine used in Example 21 was changed to 114 parts, and the azo pigments 23 (A1-18 and A3-18) were carried out. 170 parts (yield: 84.6%) of the mixture was obtained. As a result of LC-MS spectrum measurement, the content of A2-18 was 20.0% by mass. Next, 138 parts of a red colorant (RP-23) was obtained by performing the same operation as in Example 1 except that the azo pigment 23 was used instead of the azo pigment 1 used in Example 1.

<Manufacturing method 2 of pigment compositions for color filters (A1, A2)>
[Example 24] (Production of red colorant (RP-24))
The same as in Example 1 except that 142.5 parts of the azo pigment 18 and 7.5 parts of the dye derivative represented by the formula (11-3) were used instead of 150 parts of the azo pigment 18 used in Example 18. The operation was carried out to obtain 138 parts of a red colorant (RP-24).

[Example 25] (Production of red colorant (RP-25))
The same as in Example 1 except that 142.5 parts of the azo pigment 18 and 7.5 parts of the dye derivative represented by the formula (12-3) were used instead of 150 parts of the azo pigment 18 used in Example 18. The operation was carried out to obtain 138 parts of a red colorant (RP-25).

[Example 26] (Production of red colorant (RP-26))
The same as in Example 1 except that 142.5 parts of the azo pigment 18 and 7.5 parts of the dye derivative represented by the formula (15-12) were used instead of 150 parts of the azo pigment 18 used in Example 18. The operation was carried out to obtain 138 parts of a red colorant (RP-26).

[Example 27] (Production of red colorant (RP-27))
Same as in Example 1 except that 142.5 parts of the azo pigment 18 and 7.5 parts of the dye derivative represented by the formula (18-5) were used instead of 150 parts of the azo pigment 18 used in Example 18. The operation was carried out to obtain 138 parts of a red colorant (RP-27).

[Example 28] (Production of red colorant (RP-28))
The same as in Example 1 except that 142.5 parts of the azo pigment 18 and 7.5 parts of the dye derivative represented by the formula (19-4) were used instead of 150 parts of the azo pigment 18 used in Example 18. The operation was carried out to obtain 138 parts of a red colorant (RP-28).

[Example 29] (Production of red colorant (RP-29))
Same as in Example 1 except that 142.5 parts of the azo pigment 18 and 7.5 parts of the dye derivative represented by the formula (19-5) were used instead of 150 parts of the azo pigment 18 used in Example 18. The operation was carried out to obtain 138 parts of a red colorant (RP-29).

[Example 30] (Production of red colorant (RP-30))
The same as in Example 1 except that 142.5 parts of the azo pigment 18 and 7.5 parts of the dye derivative represented by the formula (20-1) were used instead of 150 parts of the azo pigment 18 used in Example 18. The operation was carried out to obtain 138 parts of a red colorant (RP-30).

[Example 31] (Production of red colorant (RP-31))
The same operation as in Example 13 was performed except that 688 parts of dinaphthol was used instead of 182 parts of dinaphthol used in Example 13, and 163 parts of azo pigment 24 (mixture of A1-19 and A2-19) was used. (Yield: 96.3%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-19 was 2.0% by mass, and A2-19 was a mixture of A2-19a and A2-19b. Next, 138 parts of a red colorant (RP-31) was obtained by performing the same operation as in Example 1 except that the azo pigment 24 was used instead of the azo pigment 1 used in Example 1.

[Example 32] (Production of red colorant (RP-32))
The same operation as in Example 13 was carried out except that 91 parts of dinaphthol was used instead of 82 parts of dinaphthol used in Example 13, and 184 parts of azo pigment 25 (mixture of A1-20 and A2-20) was used. (Yield: 97.0%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-20 was 2.0% by mass, and A2-20 was a mixture of A2-20a and A2-20b. Next, 138 parts of a red colorant (RP-32) was obtained by performing the same operation as in Example 1 except that the azo pigment 25 was used instead of the azo pigment 1 used in Example 1.

[Example 33] (Production of red colorant (RP-33))
The same operation as in Example 13 was carried out except that 94 parts of dinaphthol 7 was used instead of 82 parts of dinaphthol used in Example 13, and 174 parts of azo pigment 26 (mixture of A1-21 and A2-21) was used. (Yield: 95.0%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-21 was 2.0% by mass, and A2-21 was a mixture of A2-21a and A2-21b. Next, 138 parts of a red colorant (RP-33) was obtained by performing the same operation as in Example 1 except that the azo pigment 26 was used instead of the azo pigment 1 used in Example 1.

[Example 34] (Production of red colorant (RP-34))
The same operation as in Example 13 was performed except that 101 parts of dinaphthol 9 was used instead of 82 parts of dinaphthol used in Example 13, and 175 parts of azo pigment 27 (mixture of A1-22 and A2-22) was used. (Yield: 98.0%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-22 was 2.0% by mass, and A2-22 was a mixture of A2-22a and A2-22b. Next, 138 parts of a red colorant (RP-34) was obtained by performing the same operation as in Example 1 except that the azo pigment 27 was used instead of the azo pigment 1 used in Example 1.

[Example 35] (Production of red colorant (RP-35))
Instead of 89 parts of 3-amino-4-methoxybenzanilide used in Example 18, 89 parts of 3-amino-4-methoxy-3'-chlorobenzanilide was used, and dinaphthol 5 was changed from 95 parts to 83 parts. The same operation as in Example 18 was carried out except for the change, and 166 parts (yield: 97.7%) of azo pigment 28 (mixture of A1-23 and A2-23) was obtained. As a result of LC-MS spectrum measurement, the content of A2-23 was 2.0% by mass. Next, 138 parts of a red colorant (RP-35) was obtained by performing the same operation as in Example 1 except that the azo pigment 28 was used instead of the azo pigment 1 used in Example 1.

[Example 36] (Production of red colorant (RP-36))
Instead of 89 parts of 3-amino-4-methoxybenzanilide used in Example 18, 89 parts of 3-amino-4-methoxy-3'-trifluoromethylbenzanilide was used, and 95 to 67 parts of dinaphthol 5 was used. The same operation as in Example 18 was carried out except that the parts were changed to parts, and 151 parts (yield: 96.8%) of azo pigment 29 (mixture of A1-24 and A2-24) was obtained. As a result of LC-MS spectrum measurement, the content of A2-24 was 2.0% by mass. Next, 138 parts of a red colorant (RP-36) was obtained by performing the same operation as in Example 1 except that the azo pigment 29 was used instead of the azo pigment 1 used in Example 1.

[Example 37] (Production of red colorant (RP-37))
Instead of 89 parts of 3-amino-4-methoxybenzanilide used in Example 18, 89 parts of 3-amino-4-methoxy- (2'-chloro-5'-trifluoromethyl) benzanilide was used and dinaphthol. The same operation as in Example 18 was carried out except that 5 was changed from 95 parts to 67 parts, and 151 parts (yield: 97.0%) of azo pigment 30 (mixture of A1-25 and A2-25) was obtained. It was. As a result of LC-MS spectrum measurement, the content of A2-25 was 2.0% by mass. Next, 138 parts of a red colorant (RP-37) was obtained by performing the same operation as in Example 1 except that the azo pigment 30 was used instead of the azo pigment 1 used in Example 1.

[Example 38] (Production of red colorant (RP-38))
Instead of 89 parts of 3-amino-4-methoxybenzanilide used in Example 18, 89 parts of 3-amino-4-methoxy-N-methylbenzamide was used, and dinaphthol 5 was changed from 95 parts to 128 parts. Except for the above, the same operation as in Example 18 was carried out to obtain 151 parts (yield: 97.0%) of azo pigment 31 (mixture of A1-26 and A2-26). As a result of LC-MS spectrum measurement, the content of A2-26 was 2.0% by mass. Next, 138 parts of a red colorant (RP-38) was obtained by performing the same operation as in Example 1 except that the azo pigment 31 was used instead of the azo pigment 1 used in Example 1.

[Example 39] (Production of red colorant (RP-39))
Instead of 89 parts of 3-amino-4-methoxybenzanilide used in Example 18, 89 parts of 3-amino-4-methoxy-N-butylbenzamide was used, and dinaphthol 5 was changed from 95 parts to 104 parts. Except for the above, the same operation as in Example 18 was carried out to obtain 183 parts (yield: 95.0%) of azo pigment 32 (mixture of A1-27 and A2-27). As a result of LC-MS spectrum measurement, the content of A2-27 was 2.0% by mass. Next, 138 parts of a red colorant (RP-39) was obtained by performing the same operation as in Example 1 except that the azo pigment 32 was used instead of the azo pigment 1 used in Example 1.

[Example 40] (Production of red colorant (RP-40))
Instead of 89 parts of 3-amino-4-methoxybenzanilide used in Example 18, 89 parts of 3-amino-4-methoxy-N and N-dimethylbenzamide were used, and the amount of dinaphthol 5 was changed from 95 parts to 119 parts. The same operation as in Example 18 was carried out except for the change, and 205 parts (yield: 94.8%) of azo pigment 33 (mixture of A1-28 and A2-28) was obtained. As a result of LC-MS spectrum measurement, the content of A2-28 was 2.0% by mass. Next, 138 parts of a red colorant (RP-40) was obtained by performing the same operation as in Example 1 except that the azo pigment 33 was used instead of the azo pigment 1 used in Example 1.

[Example 41] (Production of red colorant (RP-41))
Instead of 89 parts of 3-amino-4-methoxybenzanilide used in Example 18, 89 parts of 3-amino-4-methoxy-N and N-diethylbenzamide were used, and the amount of dinaphthol 5 was changed from 95 parts to 104 parts. The same operation as in Example 18 was carried out except for the change, and 182 parts (yield: 94.3%) of azo pigment 34 (mixture of A1-29 and A2-29) was obtained. As a result of LC-MS spectrum measurement, the content of A2-29 was 2.0% by mass. Next, 138 parts of a red colorant (RP-41) was obtained by performing the same operation as in Example 1 except that the azo pigment 34 was used instead of the azo pigment 1 used in Example 1.

[Example 42] (Production of red colorant (RP-42))
The same operation as in Example 1 was carried out except that 162 parts of dinaphthol 13 was used instead of 120 parts of dinaphthol 1 used in Example 1, and 239 parts of azo pigment 35 (mixture of A1-30 and A2-30) was used. (Yield: 95.2%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-30 was 2.0% by mass. Next, 138 parts of a red colorant (RP-42) was obtained by performing the same operation as in Example 1 except that the azo pigment 35 was used instead of the azo pigment 1 used in Example 1.

[Example 43] (Production of red colorant (RP-43))
The same operation as in Example 1 was performed except that 129 parts of dinaphthol 14 was used instead of 120 parts of dinaphthol 1 used in Example 1, and 207 parts of azo pigment 36 (mixture of A1-31 and A2-31) was used. (Yield: 94.9%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-31 was 2.0% by mass. Next, 138 parts of a red colorant (RP-43) was obtained by performing the same operation as in Example 1 except that the azo pigment 36 was used instead of the azo pigment 1 used in Example 1.

<Comparative Example Method for Manufacturing Pigment Composition for Color Filter>
[Comparative Example 1] (Manufacturing of red colorant (RP-44))
The same operation as in Example 21 was carried out to obtain the azo compound a represented by the above formula (23). To 1350 parts of O-xylene, 183 parts of azo compound a and 15 parts of N, N-dimethylformamide were added, heated to 85 ° C., and then 63 parts of thionyl chloride was added dropwise over 30 minutes. After completion of the dropping, the mixture was refluxed for 2 hours. The above reaction solution was added dropwise to a solution prepared separately in which 35 parts of 2,5-dichloro-1,4-phenylenediamine and 2250 parts of O-xylene were heated to 85 ° C. over 1 hour, and the mixture was heated under reflux for 4 hours. After cooling this reaction solution to 95 ° C., 30 parts of a 28% aqueous ammonia solution and 30 parts of water are added, and the mixture is stirred at 95 to 100 ° C. for 30 minutes, and the precipitated reactant is filtered to form O-xylene, methanol, and boiling water. After washing with, it was dried to obtain 177 parts (yield: 88.0%) of azo pigment 37 (A1-18). As a result of LC-MS spectrum measurement, the content of A1-18 was 100% by mass. Next, 138 parts of a red colorant (RP-44) was obtained by performing the same operation as in Example 1 except that the azo pigment 37 was used instead of the azo pigment 1 used in Example 1.

[Comparative Example 2] (Manufacturing of red colorant (RP-45))
The same operation as in Example 18 was carried out except that 95 parts of dinaphthol 5 used in Example 18 was changed to 150 parts, and 152 parts of azo pigment 38 (mixture of A1-18 and A2-18) (yield: 75). .0%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-18 was 40.0% by mass. Next, 138 parts of a red colorant (RP-45) was obtained by performing the same operation as in Example 1 except that the azo pigment 38 was used instead of the azo pigment 1 used in Example 1.

[Comparative Example 3] (Manufacturing of red colorant (RP-46))
The same operation as in Example 21 was carried out except that 35 parts of 2,5-dichloro-1,4-phenylenediamine used in Example 21 was changed to 55 parts, and azo pigments 39 (A1-18 and A3-18) were carried out. 161 parts (yield: 80.1%) of the mixture was obtained. As a result of LC-MS spectrum measurement, the content of A3-18 was 40.0% by mass. Next, 138 parts of a red colorant (RP-46) was obtained by performing the same operation as in Example 1 except that the azo pigment 39 was used instead of the azo pigment 1 used in Example 1.

<Manufacturing method of other red colorants>
[Production Example 15] (Production of red colorant (RP-47)): PR254
Commercially available C.I. I. Pigment Red 254 (PR254) (BASF's "Irgafore Red B-CF") 150 parts, sodium chloride 1500 parts, and diethylene glycol 250 parts are charged into a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and 10 at 60 ° C. It was kneaded for hours and treated with salt milling. The obtained kneaded product was put into 5000 parts of warm water, stirred for 1 hour while heating at 70 ° C. to form a slurry, filtered and washed with water repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. for 24 hours. 138 parts of red colorant (RP-47) was obtained.

[Production Example 16] (Production of red colorant (RP-48)): PR177
C. I. Pigment Red 254 (BASF's "Irgafore Red B-CF"), C.I. I. Pigment Red 177 (PR177) (“CROMOPHTAL RED A2B” manufactured by BASF) was changed in the same manner as in the production of the red colorant (RP-47), and 138 parts of the red colorant (RP-48) was obtained. ..

[Production Example 17] (Production of red colorant (RP-49)): PR242
C. I. Pigment Red 254 (BASF's "Irgafore Red B-CF"), C.I. I. Pigment Red 242 (PR242) (Sandorin Scarlet 4RF manufactured by Clariant) was used in the same manner as in the production of the red colorant (RP-47), and 138 parts of the red colorant (RP-49) was obtained.

[Production Example 18] (Production of red colorant (RP-50)): PR176
C. I. Pigment Red 254 (BASF's "Irgafore Red B-CF"), C.I. I. Pigment Red 176 (PR176) (“Novoperm Carmine HF3C” manufactured by Clariant AG) was changed in the same manner as in the production of the red colorant (RP-47), and 138 parts of the red colorant (RP-50) was obtained. ..

[Production Example 19] (Production of red colorant (RP-51)): PO38
C. I. Pigment Red 254 (BASF's "Irgafore Red B-CF"), C.I. I. Pigment Orange 38 (PO38) (“Novoperm Red HF part” manufactured by Clariant AG) was changed in the same manner as the production of the red colorant (RP-47), and 138 parts of the red colorant (RP-51) was obtained. It was.

[Production Example 20] (Production of red colorant (RP-52)): Brominated diketopyrrolopyrrole pigment In a stainless steel reaction vessel equipped with a reflux tube, 200 parts of tert-amyl alcohol dehydrated with alkoxide under a nitrogen atmosphere. , And 140 parts of sodium-tert-amyl alkoxide was added and heated to 100 ° C. with stirring to prepare an alcoholate solution. On the other hand, 88 parts of diisopropyl succinate and 153.6 parts of 4-bromobenzonitrile were added to a glass flask and heated to 90 ° C. with stirring to dissolve them to prepare a solution of a mixture thereof. The heated solution of this mixture was slowly added dropwise to the alcoholate solution heated to 100 ° C. at a constant rate over 2 hours with vigorous stirring. After completion of the dropping, heating and stirring were continued at 90 ° C. for 2 hours to obtain an alkali metal salt of a diketopyrrolopyrrole pigment. Further, 600 parts of methanol, 600 parts of water, and 304 parts of acetic acid were added to a reaction vessel with a glass jacket, and the mixture was cooled to −10 ° C. This cooled mixture was cooled to 75 ° C. using a high-speed stirring disperser while rotating a share disk having a diameter of 8 cm at 4000 rpm, and the alkali metal salt of the previously obtained diketopyrrolopyrrole pigment was obtained. The solution was added in small portions. At this time, the rate at which the alkali metal salt of the diketopyrrolopyrrole pigment is added at 75 ° C. while cooling so that the temperature of the mixture consisting of methanol, acetic acid, and water is always maintained at −5 ° C. or lower. Was added in small portions over approximately 120 minutes while adjusting. After the addition of the alkali metal salt, red crystals were precipitated and a red suspension was formed. Subsequently, the obtained red suspension was washed with an ultrafiltration device at 5 ° C. and then filtered to obtain a red paste. This paste was redispersed in 3500 parts of methanol cooled to 0 ° C. to prepare a suspension having a methanol concentration of about 90%, and the paste was stirred at 5 ° C. for 3 hours to perform particle sizing and washing with crystal transition. Subsequently, the water paste of the obtained diketopyrrolopyrrole pigment was filtered by an ultrafiltration membrane, dried at 80 ° C. for 24 hours, and pulverized to obtain 150.8 parts of the brominated diketopyrrolopyrrole pigment. Got C. I. Pigment Red 254 (BASF's "Irgafore Red B-CF") was changed to a brominated diketopyrrolopyrrole pigment in the same manner as in the production of the red colorant (RP-47), and 138 parts of red coloring were performed. The agent (RP-52) was obtained.

<Manufacturing method of coloring composition for color filter>
[Example 44] (Preparation of coloring composition (RM-1))
The mixture having the following composition is stirred and mixed so as to be uniform, and then dispersed for 5 hours on an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) using 0.5 mm diameter zirconia beads, and then 5 The mixture was filtered through a 0.0 μm filter to prepare a coloring composition 1 (RM-1).
Red colorant (RP-1): 10.0 parts Dispersant 1: 3.0 parts Acrylic resin solution 1: 35.0 parts Propylene glycol monomethyl ether acetate: 52.0 parts

[Examples 45 to 86, Comparative Examples 4 to 9] (Preparation of coloring compositions (RM-2 to 49))
Coloring compositions (RM-2 to 49) similar to the coloring composition (RM-1) except that the red colorant (RP-1) was changed to the pigment composition (red colorant) shown in Table 3. ) Was prepared.

<Evaluation of coloring composition>
The dispersibility of the obtained coloring composition and the heat resistance, light resistance, and foreign matter evaluation of the coating film produced using the same were carried out by the following methods. The results are shown in Table 4.

(Dispersibility evaluation (viscosity characteristics))
The initial viscosity of the obtained colored composition at 25 ° C. was measured using an E-type viscometer (“ELD-type viscometer” manufactured by Toki Sangyo Co., Ltd.). Separately, 25 g of the pigment dispersion was allowed to stand at 40 ° C. for 24 hours in a sealed state in a glass container, and then the viscosity was measured by the same method as described above to obtain the viscosity over time. The viscosity of the coloring composition was synonymous with dispersibility.
⊚: When the viscosity change rate is less than ± 5% and no sediment is formed. (Extremely good)
◯: When the viscosity change rate is ± 5% or more and less than ± 10%, and no sediment is formed. (Good)
Δ: When the viscosity change rate is ± 10% or more and less than 20%, and no sediment is formed. (Defective)
X: When the sediment is formed even if the viscosity change rate is ± 20% or more or the viscosity change rate is less than ± 20%. (Extremely bad)

(Heat resistance evaluation)
The obtained coloring composition was applied onto a glass substrate having a thickness of 100 mm × 100 mm and a thickness of 1.1 mm using a spin coater so that the dry film thickness was 2.0 μm, and then dried at 70 ° C. for 20 minutes. Then, it was heated at 230 ° C. for 60 minutes and allowed to cool to prepare a coated substrate (one aspect of a color filter). The chromaticity ([L * (1), a * (1), b * (1)]) of the obtained coating film at the C light source is measured by a spectrophotometer (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.). Measured using. After that, as a heat resistance test, the mixture was heated at 250 ° C. for 1 hour, the chromaticity ([L * (2), a * (2), b * (2)]) with a C light source was measured, and the following formula was used. , Color difference ΔEab * was obtained and evaluated in the following four stages.
ΔEab * = √ ((L * (2) -L * (1)) 2+ (a * (2) -a * (1)) 2+ (b * (2) -b * (1)) 2)
⊚: ΔEab * is less than 1.0 (extremely good)
◯: ΔEab * is 1.0 or more and less than 2.5 (good)
Δ: ΔEab * is 2.5 or more and less than 5.0 (defective)
X: ΔEab * is 5.0 or more (extremely defective)

(Light resistance evaluation)
A coated substrate is prepared by the same method as the heat resistance evaluation, and the chromaticity ([L * (1), a * (1), b * (1)]) at the C light source is measured by a spectrophotometer (Olympus optics). The measurement was performed using "OSP-SP100" manufactured by the same company. Subsequently, an ultraviolet cut filter (“COLORED OPTICAL part LASS L38” manufactured by Hoya Co., Ltd.) was attached on the substrate, and after irradiating with ultraviolet rays for 100 hours using a 470 W / m ² xenon lamp, the chromaticity with the C light source ( [L * (2), a * (2), b * (2)]) was measured, and the color difference ΔEab * was obtained by the above formula and evaluated by the same criteria as the heat resistance.

(Evaluation of foreign matter on the coating film)
The obtained coloring composition was applied onto a 100 mm × 100 mm, 1.1 mm thick glass substrate using a spin coater so that the dry film thickness was 2.0 μm, and then dried at 70 ° C. for 20 minutes. Then, a coated substrate was prepared by heating and allowing to cool at 230 ° C. for 60 minutes. For evaluation, surface observation was performed using a metallurgical microscope "BX60" manufactured by Olympus System Corporation. The magnification was set to 500 times, and the number of particles that could be observed in any five fields of view by transmission was counted. It was evaluated on the following four stages.
⊚: The number of foreign substances is less than 5 (extremely good)
◯: The number of foreign substances is 5 or more and less than 10 (good)
Δ: The number of foreign substances is 10 or more and less than 60 (defective)
X: The number of foreign substances is 60 or more (extremely defective)

The coloring composition using the colorant of the present invention gave good results in dispersibility, heat resistance of the coating film, light resistance, and foreign matter in the coating film. The coloring composition using the azo pigment (A2) or the azo pigment A1 containing the azo pigment (A3) in a specific ratio was excellent in dispersibility, heat resistance, light resistance, and foreign matter in the coating film. Further, the coloring composition using an azo pigment in which one of Ra and Rb is a phenyl group and X and Y are both chlorine atoms was particularly excellent in heat resistance and light resistance. Further, the coloring composition using the azo pigment containing 2% by mass of the azo pigment A2 was particularly excellent in dispersibility. Further, the one using the dye derivative was particularly excellent in terms of foreign matter in the coating film.

<Manufacturing method of photosensitive coloring composition for color filter>
First, a coloring composition using the photosensitive coloring composition was prepared.

(Preparation of coloring composition (RM-50)): PR254
The mixture having the following composition is stirred and mixed so as to be uniform, and then dispersed for 5 hours on an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) using 0.5 mm diameter zirconia beads, and then 5 A colored composition (RM-50) was prepared by filtering with a 0.0 μm filter.
Red colorant (RP-47): 10.0 parts Dispersant 1: 3.0 parts Acrylic resin solution 1: 35.0 parts Propylene glycol monomethyl ether acetate: 52.0 parts

(Preparation of coloring composition (RM-51)): PR242
A coloring composition (RM-51) was prepared in the same manner as the coloring composition (RM-50) except that the red colorant (RP-47) was changed to the red colorant (RP-49).

(Preparation of Coloring Composition (RM-52)): Brominated Diketopyrrolopyrrole Pigment Coloring Composition (RM-50) except that the red colorant (RP-47) was changed to the red colorant (RP-52). A coloring composition (RM-52) was prepared in the same manner as in the above.

[Example 87] (Preparation of photosensitive coloring composition (RR-1))
The mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a 1 μm filter to prepare a photosensitive coloring composition (RR-1).
Coloring composition (RM-1): 20.5 parts Coloring composition (RM-30): 22.5 parts Acrylic resin solution 2: 8.2 parts Photopolymerizable monomer ("Aronix M402" manufactured by Toagosei Co., Ltd. ): 2.8 parts Photopolymerization initiator (BASF's "Irgacure 907"): 2.0 parts sensitizer (Hodogaya Chemical Co., Ltd. "EAB-F"): 0.4 parts propylene glycol monomethyl ether Acetate: 43.6 parts

[Examples 88 to 131, Comparative Examples 10 to 26] (Photosensitive coloring compositions (RR-2 to 62))
The ratio of the coloring composition to the combination of the coloring composition shown in Table 5 and the chromaticity of x = 0.640 and y = 0.330 with the C light source at the time of coating film evaluation (total amount of the coloring composition). Photosensitive coloring compositions (RR-2 to 62) were obtained in the same manner as in Example 87 except that the ratio was changed to 43 parts.

<Evaluation of photosensitive coloring composition for color filters>
The brightness (color characteristics) of the red coating film produced using the obtained photosensitive coloring composition was evaluated by the following method. Table 5 shows the evaluation results.

(Brightness Y (C) evaluation)
The obtained photosensitive coloring composition is applied onto a glass substrate having a thickness of 100 mm × 100 mm and 0.7 mm to a thickness of x = 0.640 and y = 0.330 with a C light source, and after drying. , Ultraviolet rays of 300 mJ / cm ² were irradiated using an ultra-high pressure mercury lamp. Further, a red coating film was obtained by heating at 230 ° C. for 60 minutes. Then, the brightness Y (C) of the obtained coating film was measured with a microspectrophotometer (“OSP-SP200” manufactured by Olympus Optical Co., Ltd.). Regarding the brightness Y (C), if it is 0.2 points or more, it can be said that there is a clear difference.

From the results in Table 5, it was clarified that the examples using the colorant of the present invention were excellent in brightness in forming the color filter. In particular, C.I., which has been conventionally used as a bluish pigment. I. Pigment Red 177 and C.I. I. The effect of improving brightness was confirmed by using it instead of Pigment Red 176.

<Making color filters>
A green photosensitive coloring composition and a blue photosensitive coloring composition used for producing a color filter were produced. For the red color, the photosensitive coloring composition (RR-30) of the present invention was used.

(Preparation of Green Photosensitive Coloring Composition 1 (GR-1))
The mixture having the composition shown below is uniformly stirred and mixed, dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) for 5 hours using zirconia beads having a diameter of 0.5 mm, and then 5.0 μm. The green coloring composition 1 (GM-1) was prepared by filtering with the filter of.
Green pigment (CI Pigment Green 36): 6.8 parts Yellow pigment (CI Pigment Yellow 150): 5.2 parts Resin type dispersant (BASF "EFKA4300"): 1.0 part Acrylic Resin solution 1: 35.0 parts propylene glycol monomethyl ether acetate: 52.0 parts

Next, the mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a 1 μm filter to prepare a green photosensitive coloring composition 1 (GR-1).
Green coloring composition 1 (GM-1): 42.0 parts Acrylic resin solution 2: 13.2 parts Photopolymerizable monomer ("Aronix M402" manufactured by Toa Synthetic Co., Ltd.): 2.8 parts Photopolymerization initiator ( BASF "Irgacure 907"): 2.0 parts Sensitizer (Hodogaya Chemical Industry Co., Ltd. "EAB-F"): 0.4 parts Ethylene glycol monomethyl ether acetate: 39.6 parts

(Preparation of Blue Photosensitive Coloring Composition 1 (BR-1))
The mixture having the composition shown below is uniformly stirred and mixed, dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) for 5 hours using zirconia beads having a diameter of 0.5 mm, and then 5.0 μm. The blue coloring composition 1 (BM-1) was prepared by filtering with the filter of.
Blue pigment (CI Pigment Blue 15: 6): 7.2 parts Purple pigment (CI Pigment Violet 23): 4.8 parts Resin-type dispersant (BASF's "EFKA4300"): 1.0 Part Acrylic resin solution 1: 35.0 part Propylene glycol monomethyl ether acetate: 52.0 part

Next, the mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a 1 μm filter to prepare a blue photosensitive coloring composition 1 (BR-1).
Blue coloring composition 1 (BM-1): 34.0 parts Acrylic resin solution 2: 15.2 parts Photopolymerizable monomer ("Aronix M400" manufactured by Toa Synthetic Co., Ltd.): 3.3 parts Photopolymerization initiator ( BASF "Irgacure 907"): 2.0 parts Sensitizer (Hodogaya Chemical Industry Co., Ltd. "EAB-F"): 0.4 parts Ethylene glycol monomethyl ether acetate: 45.1 parts

(Making color filters)
A black matrix was patterned on a glass substrate, and the photosensitive coloring composition 1 (RR-1) of the present invention was applied onto the substrate with a spin coater to form a colored film. The coating film was irradiated with ultraviolet rays of 300 mJ / cm ² using an ultra-high pressure mercury lamp via a photomask. Next, the unexposed portion was removed by spray development with an alkaline developer consisting of a 0.2 wt% sodium carbonate aqueous solution, washed with ion-exchanged water, and the substrate was heated at 230 ° C. for 20 minutes to obtain a red filter segment. Was formed. The red filter segments formed were x = 0.640 and y = 0.330 at the C light source. By the same method, the green photosensitive coloring composition 1 (GR-1) is x = 0.300, y = 0.600, and the blue photosensitive coloring composition 1 (BR-1) is x = 0.150, y. A green filter segment and a blue filter segment were formed so that = 0.060, and a color filter was obtained.

By using the photosensitive coloring composition (RR-30) of the present invention, it was possible to produce a high-luminance color filter.

Claims (8)

The azo pigment (A1) represented by the following general formula (1) and the azo pigment (A2) represented by the following general formula (2) or the azo pigment (A3) represented by the following general formula (3) are included. A pigment composition for a color filter
The sum of the azo pigment (A1) represented by the general formula (1) and the azo pigment (A2) represented by the general formula (2) or the azo pigment (A3) represented by the general formula (3). The content of the azo pigment (A2) represented by the general formula (2) or the azo pigment (A3) represented by the general formula (3) with respect to the amount is 2.0 to 20.0% by mass. Pigment composition for color filters.
General formula (1)
[In the general formula (1), _Ra and R _b each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group which may have a substituent. X and Y independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, or a trifluoromethyl group. ]

General formula (2)
[In the general formula (2), _Ra and R _b each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group which may have a substituent. X and Y independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, or a trifluoromethyl group. ]

General formula (3)
[In the general formula (3), _Ra and R _b each independently represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a phenyl group which may have a substituent. X and Y independently represent a hydrogen atom, a halogen atom, a cyano group, a nitro group, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, or a trifluoromethyl group. ] With respect to the total amount of the azo pigment (A1) represented by the general formula (1) and the azo pigment (A2) represented by the general formula (2) or the azo pigment (A3) represented by the general formula (3). Claim 1 in which the content of the azo pigment (A2) represented by the general formula (2) or the azo pigment (A3) represented by the general formula (3) is 2.0 to 10.0% by mass. The pigment composition for a color filter according to. The pigment composition for a color filter according to claim 1 or 2, which comprises an azo pigment (A1) represented by the general formula (1) and an azo pigment (A2) represented by the general formula (2). The pigment composition for a color filter according to any one of claims 1 to 3, further comprising a pigment derivative. A coloring composition for a color filter comprising at least a coloring agent and a binder resin, wherein the coloring agent contains the pigment composition for a color filter according to any one of claims 1 to 4. The colorant is further C.I. I. Pigment Red 254, C.I. I. The coloring composition for a color filter according to claim 5, which contains at least one selected from the group consisting of Pigment Red 242 and a brominated diketopyrrolopyrrole pigment. The coloring composition for a color filter according to claim 5 or 6, further comprising at least one selected from the group consisting of a photopolymerizable monomer and a photopolymerization initiator. A color filter comprising a filter segment formed from the coloring composition for a color filter according to any one of claims 5 to 7 on a substrate.