JP2018165768A - Color filter pigment composition, method for producing the same, color filter coloring composition, and color filter - Google Patents

Abstract

An object of the present invention is to achieve excellent dispersibility when used in a color filter coloring composition, high brightness when used in a color filter, good heat resistance and light resistance, and coating film foreign matter. It is providing the coloring composition for color filters which does not have, and a color filter using the same. The object is to provide an azo pigment (A1) represented by the general formula (1) and an azo pigment (A2) represented by the general formula (2) or an azo pigment represented by the general formula (3). A color filter pigment composition comprising (A3), the azo pigment (A1) represented by the general formula (1) and 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 problem is solved by the color filter pigment composition having a content of 2.0 to 20.0% by mass. [Selection figure] None

Description

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

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

  Patent Document 1 describes a specific azo pigment as a pigment having excellent luminance. However, even with this, sufficient luminance cannot be obtained, and further improvement has been demanded from the viewpoint of dispersion stability.

Japanese Unexamined Patent Publication No. 2014-160160

  The problems to be solved by the present invention are excellent in dispersibility when used in a coloring composition for a color filter, high brightness is obtained when used in a color filter, heat resistance and light resistance are good, and a coating film An object of the present invention is to provide a coloring composition for a color filter free from foreign matter, and a color filter using the same.

  That is, the present invention relates to an azo pigment (A1) represented by the following general formula (1) and an azo pigment (A2) represented by the following general formula (2) or an azo pigment represented by the following general formula (3). A color filter pigment composition comprising (A3), the azo pigment (A1) represented by the general formula (1) and 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 General Formula (1), R _a 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 each 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 General Formula (2), R _a 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 each 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 General Formula (3), R _a 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 each 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 present invention also provides an azo pigment (A1) represented by the general formula (1) and an azo pigment (A2) represented by the general formula (2) or an 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 It is related with the said pigment composition for color filters which is.

  Moreover, this invention relates to the said pigment composition for color filters containing the azo pigment (A1) represented by General formula (1), and the azo pigment (A2) represented by General formula (2).

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

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

  In the present invention, the colorant may further be C.I. I. Pigment red 254, C.I. I. It is related with the said coloring composition for color filters containing at least 1 sort (s) chosen from the group which consists of pigment red 242 and brominated diketopyrrolopyrrole pigment.

  Moreover, this invention relates to the said coloring composition for color filters containing further at least 1 sort (s) chosen from the group which consists of a photopolymerizable monomer and a photoinitiator.

  Moreover, this invention relates to the color filter which comprises the filter segment formed from the said coloring composition for color filters on a board | substrate.

  Furthermore, this invention relates to the manufacturing method of the pigment composition for color filters characterized by carrying out a coupling reaction of the amine compound represented by following General formula (4), and the dinaphthol compound represented by following General formula (5). .

General formula (4)

[In General Formula (4), R _a 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 General Formula (5), X and Y are each independently 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 trifluoro Represents a methyl group. ]

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

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

<Pigment composition for color filter>
<Azo Pigment (A1) Represented by General Formula (1), Azo Pigment (A2) Represented by General Formula (2), Azo Pigment (A3) Represented by General Formula (3)>
The pigment composition for a color filter of the present invention includes an azo pigment (A1) represented by the following general formula (1) and an azo pigment (A2) represented by the following general formula (2) or the following general formula (3). The azo pigment (A3) represented by these is included in a specific ratio.

General formula (1)

[In General Formula (1), R _a 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 each 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 General Formula (2), R _a 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 each 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 General Formula (3), R _a 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 each 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. Specifically, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec -A butyl group and a tert- butyl group are mentioned.

Examples of the substituent 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 trifluoro Examples thereof include an alkoxycarbonyl group having 2 to 4 carbon atoms such as a methyl group and a methoxycarbonyl group, and a divalent group such as a ureyl group (-NHCONH-) and the substituents are bonded to each other 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. Specifically, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, sec-butyl Group and tert-butyl group.

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

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

  In the general formulas (2) and (3), when X and Y are not the same substituent, for example, “when X and Y are a hydrogen atom or a chlorine atom, and X and Y are not the same”, X Two structures are possible: Structure 1 in which is a hydrogen atom and Y is a chlorine atom, and Structure 2 in which X is a chlorine atom and Y is a hydrogen atom. Such structure 1 and structure 2 may be distinguished from a and b.

As the coloring composition of the present invention, from the viewpoint of luminance, 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. Moreover, it is preferable that at least one of X or Y is a halogen atom, and a chlorine atom is preferable. Moreover, it is more preferable that both X and Y are chlorine atoms.

  The pigment composition for a color filter of the present invention contains the azo pigment (A1) and the azo pigment (A2 or A3) at a specific ratio, so that the azo pigment (A2 or A3) has a particle size adjusting effect on the azo pigment (A1). The azo pigment (A2) is more preferable than the azo pigment (A3) from the viewpoint of luminance and dispersion stability.

  The coloring composition of the present invention may have a chemical structure of the general formulas (1), (2) and (3), or tautomers thereof, or may be a pigment having any crystal form. Further, it may be a mixed crystal of pigments having all crystal forms called so-called polymorphs. The crystal form of these pigments can be confirmed by powder X-ray diffraction measurement or 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 to these. In addition, when X and Y are not the same, as described above, the azo pigment (A2) and the azo pigment (A3) may include two types of structures a and b.

<Method for Producing 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 prepared by coupling an amine (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 General Formula (4), R _a 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 General Formula (5), X and Y are each independently 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 trifluoro Represents a methyl group. ]

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

  The coupling reaction is preferably performed in the pH range of 4 to 6, and a buffer solution such as acetic acid may be used at that time. In addition, the coupling reaction is performed 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 performed in the presence of an organic solvent, a lubricant, a dispersant, or an emulsifier.

  Dinaphthol represented by the general formula (5) is obtained by subjecting 2-hydroxy-3-naphthoic acid chloride represented by the following formula (6) and a diamine represented by the following general formula (7) to a condensation reaction. Can do. In the condensation reaction, a molar ratio of 2: 1 is preferred.

Formula (6)

General formula (7)

[In General Formula (7), X and Y are each independently 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 trifluoro Represents a methyl group. ]

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

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

The carboxylic acid chloride to be used is preferably isolated, but it is also possible to carry out the condensation reaction directly without this isolation step.

<Method for Producing 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) are obtained by condensing a carboxylic acid chloride of an azo compound represented by the following general formula (8) and a diamine represented by the general formula (7) at a molar ratio of 2: 1. It can be obtained by reaction.

General formula (8)

[In General Formula (8), R _a 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 an azo compound obtained by a coupling reaction between a diazo compound of an amine represented by the general formula (4) and 2-hydroxy-3-naphthoic acid. Carboxylic acid derivatives can be obtained by chlorination.

<Miniaturization of colorant>
In order to obtain high brightness and dispersion stability when the pigment composition of the present invention is a colored composition, the color of the pigment composition is reduced by subjecting the pigment particles to fineness by salt milling, acid pasting treatment, or the like as necessary. It can be suitably used as a filter pigment. The primary particle diameter of the pigment is preferably 10 nm or more and 50 nm or less.

  Salt milling is a process in which a mixture of pigment, water-soluble inorganic salt and water-soluble organic solvent is heated using a kneader such as a kneader, two-roll mill, three-roll mill, ball mill, attritor, or 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 works as a crushing aid, and it is thought that the pigment is crushed using the high hardness of the inorganic salt during salt milling, thereby generating an active surface and causing crystal growth. Yes. Accordingly, during kneading, the pigment is crushed and crystal growth occurs simultaneously, and the primary particle diameter of the pigment obtained varies 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 the salt milling is preferably 2 to 24 hours in view of the balance between the particle size distribution of the primary particles of the salt milled and the cost required for the salt milling.

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

  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 cost. 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, from the viewpoint of both processing efficiency and production efficiency.

  The water-soluble organic solvent functions to wet 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 to be used. However, since the temperature rises during salt milling and the solvent is likely to evaporate, those having a high boiling point of 120 ° C. or higher are preferable from the viewpoint of safety. Such as, 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, and most preferably 50 to 500% by weight, based on the total weight of the pigment (100% by weight).

  When the salt is milled, a resin may be added as necessary. Here, the type of resin used is not particularly limited, and natural resins, modified natural resins, synthetic resins, synthetic resins modified with natural resins, and the like can be used. The resin used is solid at room temperature, preferably insoluble in water, and more preferably partially soluble in the water-soluble organic solvent. The amount of 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 functions to wet 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 to be used. However, since the temperature rises during salt milling and the solvent is likely to evaporate, those having a high boiling point of 120 ° C. or higher are preferable from the viewpoint of safety. Such as, 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, and most preferably 50 to 500% by weight, based on the total weight of the pigment (100% by weight).

  When the salt is milled, a resin may be added as necessary. Here, the type of resin used is not particularly limited, and natural resins, modified natural resins, synthetic resins, synthetic resins modified with natural resins, and the like can be used. The resin used is solid at room temperature, preferably insoluble in water, and more preferably partially soluble in the water-soluble organic solvent. The amount of 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 using a pigment derivative, it is required that the color tone of the pigment composition is not impaired as much as possible. From the viewpoint of hue, anthraquinone derivatives, dianthraquinone derivatives, thiazine indigo derivatives, azo dye derivatives, quinophthalone derivatives, quinacridone derivatives, diketopyrrolopyrrole derivatives, naphthol derivatives, or dinaphthol derivatives are preferably used as the dye derivatives. More preferred are azo dye derivatives, naphthol derivatives, and dinaphthol derivatives. These dye derivatives are preferably used in an amount of 2 to 30% by weight, and 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 an anthraquinone derivative, the compound represented by following formula (9) can be used, However, It is not limited to these.

(Specific examples of dianthraquinone derivatives)
As the dianthraquinone derivative, specifically, a compound represented by the following formula (10) can be used, but is not limited thereto.

(Specific examples of thiazine indigo derivatives)
As the thiazineindigo derivative, specifically, a compound represented by the following formula (11) can be used, but is not limited thereto.

(Specific examples of azo dye derivatives)
As the azo dye derivative, specifically, compounds represented by the following formulas (12) to (14) can be used, but are not limited thereto.

(Specific examples of quinophthalone derivatives)
As the quinophthalone derivative, specifically, compounds represented by the following formulas (15-1) to (15-13) can be used, but are not limited thereto.

(Specific examples of quinacridone derivatives)
As the quinacridone derivative, specifically, a compound represented by the following formula (16) can be used, but is not limited thereto.

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

(Specific examples of naphthol derivatives)
As the naphthol derivative, specifically, compounds represented by the following formulas (19-1) to (19-8) can be used, but are not limited thereto.

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

<Coloring composition for color filter>
The coloring composition of the present invention includes a pigment composition containing the azo pigment represented by the general formulas (1), (2), and (3) of the present invention as an essential component, and in addition to a binder resin, an organic material is used as 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 compound represented by the general formula (1) or (2) or (3) of the present invention can be adjusted as necessary. It is preferable to contain 0.01-50 mass% in a thing, and it is more preferable to make it contain 0.1-30 mass%.

<Binder resin>
Examples of the binder resin contained in the colored 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 resins, vinyl resins, alkyd resins, polystyrene resins, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polyethylene (HDPE, LDPE), polybutadiene, polyimide resins, and the like.

  When used as a coloring composition for a color filter, the spectral transmittance is preferably 80% or more, more preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region. Moreover, when using with the form of an alkali image development type colored resist, it is preferable to use the alkali-soluble vinyl resin which copolymerized the acidic group containing ethylenically unsaturated monomer. 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 resins having an acidic group such as a carboxyl group or a sulfone group. Specific examples of the alkali-soluble resin include an acrylic resin having an acidic group, an α-olefin / (anhydrous) maleic acid copolymer, a styrene / styrene sulfonic acid copolymer, an ethylene / (meth) acrylic acid copolymer, or Examples include isobutylene / (anhydrous) maleic acid copolymer. Among these, at least one resin selected from an acrylic resin having an acidic group and 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.

  Energy ray curable resins having ethylenically unsaturated active double bonds include reactive substitution of isocyanate groups, aldehyde groups, epoxy groups, etc. on polymers having reactive substituents such as hydroxyl groups, carboxyl groups, amino groups, etc. A resin in which a photo-crosslinkable group such as a (meth) acryloyl group or a styryl group is introduced into the polymer by reacting a (meth) acrylic compound having a group or cinnamic acid is used. In addition, polymers containing acid anhydrides such as styrene-maleic anhydride copolymer and α-olefin-maleic anhydride copolymer are half-esterified with a (meth) acrylic compound having a hydroxyl group such as hydroxyalkyl (meth) acrylate. A modified version is also used.

  A thermoplastic resin having both alkali-soluble performance and energy ray curing performance is also preferable as the photosensitive coloring composition for color filters.

  The following are mentioned as a monomer which comprises the said thermoplastic resin. 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) Acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, methoxypolypropylene glycol (meth) acrylate, or ethoxypolyethylene Glycol (meth) acrylate of (meth) acrylates,

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

Alternatively, cyclohexylmaleimide, phenylmaleimide, methylmaleimide, ethylmaleimide, 1,2-bismaleimide ethane 1,6-bismaleimidehexane, 3-maleimidopropionic acid, 6,7-methylenedioxy-4-methyl-3-maleimide Coumarin, 4,4′-bismaleimide diphenylmethane, bis (3-ethyl-5-methyl-4-maleimidophenyl) methane, N, N′-1,3-phenylenedimaleimide, N, N′-1,4- Phenylene dimaleimide, 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-succin Midyl-3-maleimidobenzoate, N-succinimidyl-3-maleimidopropionate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidohexanoate, N- [4- (2-benzimidazolyl) phenyl N-substituted maleimides such as maleimide and 9-maleimide acridine.

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

  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.

  The coloring composition for a color filter of the present invention preferably includes a thermosetting resin in terms of heat resistance, for example, among them, an epoxy resin and a melamine resin can be more suitably used, and a melamine resin is particularly preferable. Of these, a melamine compound having a methylolimino 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 the amount is less than 10 parts by weight, the effect of improving heat resistance and light resistance is reduced, and if it exceeds 60 parts by weight, the developability deteriorates during alkali development, 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 disperse the colorant preferably. The number average molecular weight (Mn) is preferably in the range of 2,500 to 50,000, and the value of Mw / Mn is preferably 10 or less.

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

  When using a binder resin as a coloring composition for a color filter, from the viewpoint of dispersibility, developability, and heat resistance, a carboxyl group, a pigment carrier, and an organic solvent that act as a pigment adsorbing group and an alkali-soluble group during development. The balance between the aliphatic group and aromatic group acting 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. When the acid value is less than 20 mgKOH / g, the solubility in the developing solution is poor and it is difficult to form a fine pattern. When 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 formability and various resistances are insufficient, and if it exceeds 500% by weight, the pigment concentration is low and color characteristics cannot be expressed.

<Organic solvent>
In the coloring composition of the present invention, the pigment composition is sufficiently dispersed and infiltrated in a carrier, and applied to a substrate such as a glass substrate so as to have a dry film thickness of 0.2 to 5 μm to form a filter segment. An organic solvent can be included to facilitate the process. The organic solvent is selected in consideration of the good cloth properties of the colored composition, the solubility of each component of the colored composition, and the safety.

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, 2-heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, ethyl 3-ethoxypropionate, 3-methyl -1,3
-Butanediol, 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 dible ether, ethylene glycol Monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monotertiary 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, di Propylene 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 Acetate, 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, dibasic acid ester and the like.

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

An organic solvent can be used individually by 1 type or in mixture of 2 or more types. Moreover, since the solvent can adjust the coloring composition to an appropriate viscosity and can form a filter segment having a desired uniform film thickness, the total weight of the coloring composition is based on (100% by weight), and is 500 to 4000% by weight. It is preferable to use it in the quantity.

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

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

(Resin type dispersant)
The resin-type dispersant has a pigment-affinity part that has the property of adsorbing to the colorant and a part that is compatible with the carrier, and functions to adsorb to the colorant and stabilize dispersion on the carrier. It is. As the resin-type dispersant, an acidic resin-type dispersant is preferable, and an acidic substituent, an aromatic group, or the like is added to the main chain or terminal of the linear resin, the main chain or side chain of the comb-like resin, in a block or randomly. What has is preferable. Specifically, polycarboxylic acid esters such as polyurethane and polyacrylate, unsaturated polyamide, polycarboxylic acid, polysiloxane, long-chain polyaminoamide phosphate, hydroxyl group-containing polycarboxylic acid ester, modified products thereof, poly ( An amide formed by a reaction between 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 High molecular compounds, polyesters, modified poly (meth) acrylates, ethylene oxide / propylene oxide adducts, phosphate esters, and the like are used. These may be used alone or in admixture of two or more, but are not necessarily limited thereto.

  Among the above-mentioned dispersants, a polymer dispersant having an acidic functional group is preferable because the viscosity of the dispersion is reduced with a small addition amount and high contrast is exhibited. Examples of the acidic substituent include a phosphate group, Examples include sulfonic acid groups and carboxyl groups. Further, 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 based on the total amount of the colorant, and more preferably about 10 to 100% by weight from the viewpoint of film formability.

  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 SOLPERSE-3000, 9000, 13000, 13240, 13650, 13940, 16000 manufactured by Nihon Lubrizol Corporation, such as Lactimon, Lactimon-WS or Bykumen. 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, 31845, 32000, 32500, 32550, 33500, 32600, 34750, 35100, 36600, 38500, 41000, 41090, 53095, 55000, 76500, etc., manufactured by BASF 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, 1 01,120,150,1501,1502,1503, etc., Ajinomoto Fine-Techno Co., Ltd. of AJISPER PA111, PB711, PB821, PB822, PB824, and the like.

(Surfactant)
Surfactants include sodium lauryl sulfate, polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium stearate, sodium alkyl naphthalene sulfonate, sodium alkyl diphenyl ether disulfonate , Anionic surfactants such as monoethanolamine lauryl sulfate, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate ester, Polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene Nonionic surfactants such as alkyl ether phosphates, polyoxyethylene sorbitan monostearate and polyethylene glycol monolaurate, chaotic surfactants such as alkyl quaternary ammonium salts and their ethylene oxide adducts, alkyldimethylamino Examples include amphoteric surfactants such as alkylbetaines such as betaine acetate and alkylimidazolines, and these can be used alone or in admixture of two or more, but are not necessarily limited thereto.

  The amount of the resin-type dispersant and surfactant added 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). It 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 added effect. May affect.

<Photopolymerizable monomer>
Photopolymerizable monomers that can be added to the color filter coloring composition include monomers or oligomers that are cured by ultraviolet rays or heat to produce a transparent resin, and these are used alone or in combination of two or more. It can be used by mixing. The 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 ( (Meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, 1,6-hexanediol diglycy Luether di (meth) acrylate, bisphenol A diglycidyl ether di (meth) acrylate, neopentyl glycol diglycidyl ether di (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, tricyclodeca Nyl (meth) acrylate, ester acrylate, methylolated melamine (meth) acrylate ester, epoxy (meth) acrylate, urethane acrylate and other acrylic esters and methacrylate esters, (meth) acrylic acid, styrene, vinyl acetate, Hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth) acrylamide, N-hydroxymethyl Examples include, but are not necessarily limited to, til (meth) acrylamide, N-vinylformamide, acrylonitrile and the like.

<Photopolymerization initiator>
When the photosensitive coloring composition for color filters is cured by ultraviolet irradiation and a filter segment is formed by a photolithographic method, a photopolymerization initiator or the like is added to add a photopolymerization initiator or the like to a solvent developing type or alkali developing type coloring resist material. It can be prepared in the form. The blending amount when using the photopolymerization initiator is preferably 2 to 200% by weight based on the total amount of the colorant, and 5 to 150% by weight from the viewpoint of photocurability and developability. More preferred.

  As photopolymerization initiators, 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl-2-hydroxy-2-methylpropan-1-one, 1-hydroxy Cyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinoprop-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1- Acetophenone-based compounds such as [4- (4-morpholinyl) phenyl] -1-butanone or 2-benzyl-2-dimethylami-1- (4-morpholinophenyl) -butan-1-one; nzoin, benzoin methyl ether , Benzoin ethyl ether, benzoin isopropyl ether, or benzyldi Benzoin compounds such as tilketal; benzophenone benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4′-methyldiphenisulphide, or 3,3 ′, 4 Benzophenone compounds such as 4′-tetra (t-butylperoxycarbonyl) nzophenone; thioxanthone, 2-chlorothioxanthone 2-methylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthiosantone, 2,4-diethylthioxanthone, etc. Thioxanthone compounds; 2,46-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -triazine, 2- (p-methoxyphenyl) -4,6-bi (Trichloromethyl) -striazine, 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- (naphth-1-yl) -4,6bis (trichloromethyl) -s-triazine, 2- (4-methoxy-naphth-1-yl) Triazines such as 4,6-bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl- (piphenyl) -6-triazine, or 2,4-trichloromethyl- (4′-methoxystyryl-6-triazine) 1,2-octanedione, 1- [4- (ferthio)-, 2- (O-benzoyloxime)], or O- (acetyl) -N- (1- Oxime ester compounds such as benzyl-2-oxo-2- (4′-methoxy-naphthyl) ethylidene) hydroxylami; bis (2,4,6-trimethylbenzoyl) phenyl phosphine oxide, or 2,4,6- Phosphine compounds such as trimethylbenzoyldiphenylphosphine oxide; quinone compounds such as 9,10-phenanthrenequinone, camphorquinone and elanthraquinone; borate compounds; carbazole compounds; midazole compounds; or titanocene compounds Is used.

  These photopolymerization initiators can be used alone or in combination 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 color filter coloring composition (100% by weight), and 5 from the viewpoint of photocurability and developability. More preferably, it is -150 weight%.

<Sensitizer>
Furthermore, the photosensitive coloring composition for a color filter of the present invention can contain a sensitizer. Sensitizers include chalcone derivatives, unsaturated ketones such as dibenzalacetone, 1,2-diketone derivatives such as benzyl and camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives , Xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, oxonol derivatives, etc., polymethine dyes, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, idrin derivatives, Azulene derivatives, azulenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, tetrabenzoporphyrin derivatives, te Lapyrazinoporphyrazine derivatives, phthalocyanine derivatives, tetraazaporphyrazine derivatives, tetraquinoxalyloporphyrazine derivatives, naphthalocyanine derivatives, subphthalocyanine derivatives, pyrylium derivatives, thiopyrylium derivatives, tetraphyrin derivatives, annulene derivatives, spiropyran derivatives, spirooxazines Derivatives, thiospiropyran derivatives, metal arene complexes, organoruthenium complexes, or Michler's ketone derivatives, α-acyloxy esters, acylphosphine oxides, methylphenylglyoxylate, benzyl, 9,10-phenanthrenequinone, camphorquinone, ethyl Anthraquinone, 4,4′-diethylisophthalophenone, 3,3 ′ or 4,4′-tetra (t-butylperoxycarbonyl) benzopheno And 4,4′-diethylaminobenzophenone.

  More specifically, edited by Shin Okawara et al., “Dye Handbook” (1986, Kodansha), edited by Shin Okawara et al., “Chemistry of Functional Dye” (1981, CMC), edited by Tadasaburo Ikemori et al. Examples include, but are not limited to, sensitizers described in "Special Functional Materials" (1986, CMC). In addition, a sensitizer that absorbs light from the ultraviolet region to the near infrared region can also be contained.

  Two or more kinds of sensitizers may be used in any ratio as required. The blending amount when using the sensitizer is preferably 3 to 60% by weight based on the total weight of the photopolymerization initiator contained in the colored composition (100% by weight). From the viewpoint of developability, it is more preferably 5 to 50% by weight.

<Amine compound>
Moreover, the coloring composition for color filters of this invention can be made to contain the amine compound which has a function which reduces the dissolved oxygen. Such amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminobenzoate. Examples include ethyl, 2-ethylhexyl 4-dimethylaminobenzoate, and N, N-dimethylparatoluidine.

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

  Particularly preferred as a leveling agent is a kind of so-called surfactant having a hydrophobic group and a hydrophilic group in the molecule, having a hydrophilic group but low solubility in water, and when added to a coloring composition, It has the characteristics of low surface tension reduction ability, and it is useful to have good wettability to the glass plate despite its low surface tension reduction ability. Those that can sufficiently suppress the chargeability can be preferably used. As a leveling agent having such preferable characteristics, dimethylpolysiloxane having a polyalkylene oxide unit can be preferably used. Examples of the polyalkylene oxide unit include 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 end of dimethylpolysiloxane is bonded, and dimethylpolysiloxane. Any of linear block copolymer types in which they are alternately and repeatedly bonded may be used. Dimethylpolysiloxane 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 thereto.

  An anionic, cationic, nonionic or amphoteric surfactant can be supplementarily added to the leveling agent. Two or more kinds of surfactants may be mixed and used.

  Anionic surfactants added to the leveling agent as auxiliary agents include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkyl naphthalene sulfonate, alkyl diphenyl ether disulfonic acid Sodium, lauryl sulfate monoethanolamine, lauryl sulfate triethanolamine, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate Examples include esters.

  Examples of the chaotic surfactant that is supplementarily added to the leveling agent include alkyl quaternary ammonium salts and their ethylene oxide adducts. Nonionic surfactants added to the leveling agent as auxiliary agents include polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate ester, polyoxyethylene sorbitan monostearate And amphoteric surfactants such as alkyl dimethylamino acetic acid betaine and alkylimidazolines, and fluorine-based and silicone-based surfactants.

<Curing agent / Curing accelerator>
Moreover, in order to assist hardening of a thermosetting resin, the coloring composition for color filters of this invention may contain the hardening | curing agent, the hardening accelerator, etc. as needed. As the curing agent, phenol resins, amine compounds, acid anhydrides, active esters, carboxylic acid compounds, sulfonic acid compounds, and the like are effective, but are not particularly limited to these, and thermosetting resins. Any curing agent may be used as long as it can react with the. Among these, a compound having two or more phenolic hydroxyl groups in one molecule and an amine curing agent are preferable. 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 amidine compounds and salts thereof (eg Imidazole, 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 4-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, 1- (2-cyanoethyl) -2- D Ru-4-methylimidazole, etc.), phosphorus compounds (eg, triphenylphosphine, etc.), guanamine compounds (eg, melamine, guanamine, acetoguanamine, benzoguanamine, etc.), S-triazine derivatives (eg, 2,4-diamino-6) -Methacryloyloxyethyl-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. As content of the said hardening accelerator, 0.01 to 15 weight% is preferable with respect to the thermosetting resin whole quantity.

<Other colorants>
The coloring composition for a color filter of the present invention contains the pigment composition of the present invention as a colorant. However, in order to adjust the chromaticity, etc., a pigment composition such as other pigments or dyes as long as the effects of the present invention are not impaired. You may use a thing together. The colorant that may be used in combination is 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, Mention may be made of red pigments such as 279, 280, 281, 282, 283, 284, 285, 286 or 287. Examples of red dyes include xanthene series, azo series (pyridone series, barbituric acid series, metal complex series, etc.), disazo series, and anthraquinone series. Specifically, C.I. I. And salt forming compounds of xanthene 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 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, 181 182,185,187,188,193,194,198,199,213,214,218,219,220, or a yellow pigment 221 and the like can be used in combination. Examples of the orange dye and / or yellow dye include quinoline series, azo series (pyridone series, barbituric acid series, metal complex series, etc.), disazo series, and methine series.

  Preferred dyes to be used in combination include azo dyes, naphtholazo dyes, diketopyrrolopyrrole dyes, anthraquinone dyes, and quinophthalone dyes from the viewpoint of luminance. Specifically, C.I. I. Pigment red 176, 177, 254, 242, C.I. I. Pigment Yellow 138, 150, brominated diketopyrrolopyrrole pigment. Among these, particularly preferred dyes are C.I. I. Pigment red 254, C.I. I. Pigment Red 242, and brominated diketopyrrolopyrrole pigments.

  When the above-mentioned other dyes are used in addition to 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 ingredients>
The coloring composition for a color filter of the present invention can contain a storage stabilizer in order to stabilize the viscosity with time of the composition. Moreover, in order to improve adhesiveness with a transparent substrate, adhesion improving agents, such as a silane coupling agent, can also be contained.

  Examples of storage stabilizers include quaternary ammonium chlorides such as benzyltrimethyl chloride and diethylhydroxyamine, organic acids such as lactic acid and oxalic acid, and methyl ethers thereof, t-butylpyrocatechol, tetraethylphosphine, and tetraphenylphosphine. Organic phosphines, phosphites and the like can be mentioned. 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).

  Examples of the adhesion improver include vinyl silanes such as vinyltris (β-methoxyethoxy) silane, vinylethoxysilane and vinyltrimethoxysilane, (meth) acrylsilanes such as γ-methacryloxypropyltrimethoxysilane, 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-aminopropyltrie Xisilane, N-β (aminoethyl) γ-aminopropylmethyldiethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane, N-phenyl Examples include silane coupling agents such as aminosilanes such as -γ-aminopropyltriethoxysilane, and 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).

<Method for producing colored 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. Various dispersing machines such as a three-roll mill, a two-roll mill, a sand mill, a kneader, or an attritor It can be dispersed and manufactured using. Moreover, the coloring composition of this invention can also be manufactured by mixing what was disperse | distributed in the binder resin and the organic solvent separately for a coloring agent.

  In this way, when the colorant is dispersed in the binder resin using a disperser, the dispersed particle size becomes smaller as the dispersion proceeds, the transparency increases, and the contrast ratio increases. In particular, good characteristics can be obtained from about 300 nm. On the other hand, when the dispersion progresses and the dispersed particle size becomes small, the viscosity of the dispersion increases and the thixotropic property tends to increase. When used as a photosensitive coloring composition for a color filter, it is required to have a low viscosity and a Newtonian flow because it is required to be coated with a thin film and to have a smooth coating surface. For this reason, it is preferable to suppress the dispersed particle size to about 100 nm in consideration of the viscosity and thixotropic property preferable for normal use. Thus, 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 in the range of 50 nm to 150 nm, the increase in viscosity and thixotropic property are minimized. Thus, a good pigment dispersion can be obtained.

<Removal of coarse particles>
The colored composition for color filter is subjected to centrifugal separation or filtration using a sintered filter, a membrane filter or the like, so that coarse particles of 5 μm or more, preferably coarse particles of 1 μm or more, more preferably coarse particles of 0.5 μm or more. It is preferable to remove the mixed dust. Thus, it is preferable that a coloring composition does not contain a particle | grain of 0.5 micrometer or more substantially. 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. A color filter comprises a filter segment formed using a coloring composition for a color filter. Examples of the color filter include those having a red filter segment, a green filter segment, and a blue filter segment. The filter segment is coated with a color filter coloring composition by a spin coat method or a die coat method, and then ultraviolet rays or the like. The active energy rays are irradiated to cure the portion that becomes the filter segment, and then developed to form on the substrate. The red filter segment therein is formed from a coloring composition or a photosensitive coloring composition containing the colorant of the present invention.

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

  Moreover, a yellow pigment can be used together with a green coloring composition or a green photosensitive coloring composition. Examples of yellow pigments 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, Mention may be made of yellow pigments such as 182, 185, 187, 188, 193, 194, 198, 199, 213, 214, 218, 219, 220, or 221. Further, a basic dye exhibiting yellow and a salt-forming compound of an acid dye can be used in combination.

  The blue filter segment can be formed using a normal blue coloring composition or a blue photosensitive coloring composition containing a blue pigment and a pigment carrier. Examples of blue pigments include C.I. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64, etc. are used. A purple pigment can be used in combination with the blue coloring composition or the blue photosensitive coloring composition. Examples of purple pigments that can be used in combination include C.I. I. And violet pigments such as CI Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, and 50. In addition, a basic dye or a salt-forming compound of an acid dye exhibiting blue or purple can be used. When using a dye, a xanthene dye is preferable in terms of heat resistance and luminance.

<Color filter manufacturing method>
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 simply by repeating the printing and drying of the coloring composition prepared as the printing ink. Therefore, the color filter manufacturing method is low in cost and excellent in mass productivity. Furthermore, it is possible to print a fine pattern having high dimensional accuracy and smoothness by the development of printing technology. In order to perform printing, it is preferable that the ink does not dry and solidify on the printing plate or on the blanket. Control of ink fluidity on a printing press is also important, and ink viscosity can be adjusted with a dispersant or extender pigment.

  When the filter segment is formed by photolithography, the colored composition prepared as the solvent development type or alkali development type colored resist material is applied to a transparent substrate such as a precoat, spin coat, slit coat, roll coat, etc. By a method, it applies so that a dry film thickness may be set to 0.2-5 micrometers. If necessary, the dried film is exposed to ultraviolet light through a mask having a predetermined pattern provided in contact with or non-contact with the film. Then, after immersing in a solvent or alkali developer or spraying the developer by spraying or the like to remove the uncured portion to form a desired pattern, the same operation is repeated for other colors to produce a color filter. be able to. Furthermore, in order to accelerate the polymerization of the colored resist material, heating can be performed as necessary. According to the photolithography method, a color filter with higher accuracy than the above printing method can be manufactured.

  In development, an aqueous solution such as sodium carbonate or sodium hydroxide is used as an alkali developer, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used. Moreover, an antifoamer and surfactant can also be added to a developing solution. In order to increase the UV exposure sensitivity, after coating and drying the colored resist, a water-soluble or alkaline water-soluble resin such as polyvinyl alcohol or a water-soluble acrylic resin is applied and dried to form a film that prevents polymerization inhibition by oxygen. Thereafter, ultraviolet 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 method, but the colored composition or the photosensitive colored composition of the present invention can be used in any method. The electrodeposition method is a method for producing a color filter by using a transparent conductive film formed on a substrate and forming each color filter segment on the transparent conductive film by electrophoresis of colloidal particles. . 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 this filter segment is transferred to a desired substrate.

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

(Resin polymerization average molecular weight (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 “TSK-GEL SUPER H5000”, “H4000”, “H3000” manufactured by Tosoh Corporation in order. , And “H2000” and the molecular weight in terms of polystyrene measured using tetrahydrofuran as the mobile phase.

(Resin acid value)
To 0.5 to 1.0 part of the resin solution, 80 ml of acetone and 10 ml of water are added and stirred to dissolve uniformly, and a 0.1 mol / L KOH aqueous solution is used as a titrant and an automatic titrator (“COM-555”). Titration using Hiranuma Sangyo) and the acid value of the resin solution was measured. And 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 pigment (A1, A2, A3))
LC-MS spectrum was used for identification of the azo pigments (A1, A2, A3) used in the present invention. The LC-MS spectrum was measured under the following conditions.

Apparatus: Nippon Waters Co., Ltd. UPLC H-Class / XevoTQD
Column: Symmetry C18 5micron (Nippon Waters Corporation)
Eluent:
(A) H ₂ O
(B) DMF
Eluent conditions: (A) :( B) = 10: 90 (volume ratio)
Flow rate: 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. Also, in the chromatogram obtained at the measurement wavelength under the above conditions, the peak area ratio of the azo pigment (A1) having two bonded bases and the sum of the peaks of the azo pigment (A2 or A3) having one bonded base From the area ratio, the mass ratio of (A1) and (A2 or A3) was calculated.

<Method for producing dispersant>
(Preparation of Dispersant 1)
In a reaction vessel equipped with a gas introduction tube, a thermometer, a condenser, and a stirrer, 60 parts of ethyl acrylate (EA), 40 parts of t-butyl acrylate (t-BA), 90 parts of methyl methacrylate (MMA), methacrylic acid (MAA) 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 reacted for 12 hours. It was confirmed that 95% had reacted by solid content measurement. Next, 19 parts of pyromellitic anhydride, 231 parts of cyclohexanone, and 0.40 part of 1,8-diazabicyclo- [5.4.0] -7-undecene as a catalyst were charged and reacted at 120 ° C. for 7 minutes. The reaction was terminated after confirming that 98% or more of the acid anhydride had been half-esterified by measuring the acid value. 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 10,000.

<Method for producing binder resin solution>
(Preparation of acrylic resin solution 1)
A reaction vessel equipped with a separable four-necked flask equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, a dropping tube and a stirring device was charged with 196 parts of cyclohexanone, heated to 80 ° C., and purged with nitrogen in the reaction vessel. From the tube, 37.2 parts of n-butyl methacrylate, 12.9 parts of 2-hydroxyethyl methacrylate, 12.0 parts of methacrylic acid, paracumylphenol ethylene oxide modified acrylate (“Aronix M110” manufactured by Toagosei Co., Ltd.) 20.7 A mixture of 1.1 parts of 2,2′-azobisisobutyronitrile was added dropwise over 2 hours. After completion of the dropwise addition, the reaction was continued for another 3 hours to obtain an acrylic resin solution. After cooling to room temperature, sample about 2 parts of the resin solution, heat dry at 180 ° C. for 20 minutes, measure the nonvolatile content, and add methoxypropyl acetate to the previously synthesized resin solution so that the nonvolatile 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 charged into a reaction vessel equipped with a separable four-necked flask equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, a dropping tube and a stirring device, heated to 80 ° C., and the inside of the reaction vessel was purged with nitrogen. From the tube, 20 parts of methacrylic acid, 20 parts of paracumylphenol ethylene oxide modified acrylate (Aronix M110 manufactured by Toagosei 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 dropwise addition, the reaction was further continued for 3 hours to obtain a copolymer resin solution. Next, after the nitrogen gas was stopped and stirred while injecting dry air for 1 hour with respect to the total amount of the copolymer solution obtained, the mixture was cooled to room temperature, and then 2-methacryloyloxyethyl isocyanate (Karenz manufactured by Showa Denko KK). MOI) A mixture of 6.5 parts, 0.08 part dibutyltin laurate and 26 parts cyclohexanone was added dropwise at 70 ° C. over 3 hours. After completion of the dropwise addition, the reaction was continued for another hour to obtain an acrylic resin solution. After cooling to room temperature, sample about 2 parts of the resin solution, heat dry at 180 ° C. for 20 minutes, measure the nonvolatile content, and add cyclohexanone to the previously synthesized resin solution so that the nonvolatile content is 20%. Thus, an acrylic resin solution 2 was prepared. The weight average molecular weight (Mw) was 18000.

<Method for Producing Color Filter Pigment Composition Containing Azo Pigment (A1) and Azo Pigment (A2)>
Below, the specific synthesis | combining method of the pigment composition containing an azo pigment (A1) and an azo pigment (A2) is shown. Other azo pigments according to the present invention can be synthesized according to a similar scheme.

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

[Production Example 1] (Production of dinaphthol 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 stirred at room temperature for 2 hours to prepare a 2-hydroxy-3-naphthoic acid chloride solution. Separately, 52 parts of p-phenylenediamine part was added to 1500 parts of tetrahydrofuran (THF), and then stirred for 30 minutes while maintaining at 0 to 5 ° C. The 2-hydroxy-3-naphthoic acid chloride solution prepared there was added dropwise over 30 minutes, and then 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 hot water. The taken out wet cake was dried to obtain 200 parts of dinaphthol 1 (yield: 93.4%).

[Production Examples 2 to 14] (Production of dinaphthol 2 to 14)
As shown in Table 2 below, the same operation as in Production Example 1 was performed except that the type and amount of diamine were changed, and dinaphthol 2 to 14 were obtained in the yields and yields shown in Table 2 below.

<Method for Producing Color Filter Pigment Composition (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 cooled to -2 to 0 ° C. After adding 134 parts of 25% aqueous sodium nitrite solution to this solution, the mixture was stirred for 2 hours while maintaining 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 acetic acid buffer solution having a pH of 5.4 was dropped, and then the prepared coupler solution was dropped over 40 minutes. After completion of dropping, the mixture was stirred at room temperature for 30 minutes, and further stirred while maintaining 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 hot water. To the removed wet cake, 4000 parts of water was added and stirred for 2 hours while maintaining at 80 ° C. After stirring, the reslurry liquid was filtered, washed with hot 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 into a stainless 1 gallon kneader (manufactured by Inoue Seisakusho), kneaded at 70 ° C. for 8 hours, and subjected to salt milling. The obtained kneaded product was put into 5000 parts of warm water, stirred for 1 hour while heating to 70 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. 138 parts of a red colorant (RP-1) was obtained.

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

[Example 3] (Production of red colorant (RP-3))
The same procedure as in Example 1 was carried out 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) (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, except that the azo pigment 3 was used in place of the azo pigment 1 used in Example 1, the same operation as in Example 1 was performed to obtain 138 parts of a red colorant (RP-3).

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

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

[Example 6] (Production of red colorant (RP-6))
The same operation as in Example 1 was carried out 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) (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, except that the azo pigment 6 was used in place of the azo pigment 1 used in Example 1, the same operation as in Example 1 was performed to obtain 138 parts of a red colorant (RP-6).

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

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

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

[Example 10] (Production of red colorant (RP-10))
Instead of 120 parts of dinaphthol 1 used in Example 1, 138 parts of azo pigment 10 (mixture of A1-10 and A2-10) were carried out in the same manner as in Example 1, except that 138 parts of dinaphthol 10 were 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, except that the azo pigment 10 was used in place of the azo pigment 1 used in Example 1, the same operation as in Example 1 was performed to obtain 138 parts of a red colorant (RP-10).

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

[Example 12] (Production of red colorant (RP-12))
The same procedure as in Example 1 was carried out except that 127 parts of dinaphthol 12 was used instead of 120 parts of dinaphthol 1 used in Example 1, and 211 parts of an azo pigment 12 (mixture of A1-12 and A2-12) (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, except that the azo pigment 12 was used in place of the azo pigment 1 used in Example 1, the same operation as in Example 1 was performed to obtain 138 parts of a red colorant (RP-12).

[Example 13] (Production of red colorant (RP-13))
Example 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 Example 1 was performed 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 mass%. Next, except that the azo pigment 13 was used in place of the azo pigment 1 used in Example 1, the same operation as in Example 1 was performed to obtain 138 parts of a red colorant (RP-13).

[Example 14] (Production of red colorant (RP-14))
The same procedure as in Example 13 was performed, except that 87 parts of dinaphthol 2 was used instead of 82 parts of dinaphthol 1 used in Example 13, and 185 parts of azo pigment 14 (mixture of A1-14 and A2-14) (Yield: 98.0%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-14 was 2.0% by mass. Next, except that the azo pigment 14 was used in place of the azo pigment 1 used in Example 1, the same operation as in Example 1 was performed to obtain 138 parts of a red colorant (RP-14).

[Example 15] (Production of red colorant (RP-15))
193 parts of an azo pigment 15 (mixture of A1-15 and A2-15) was carried out in the same manner as in Example 13, except that 93 parts of dinaphthol 893 was used instead of 82 parts of dinaphthol 1 used in Example 13. (Yield: 97.8%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-15 was 2.0% by mass. Next, except that the azo pigment 15 was used in place of the azo pigment 1 used in Example 1, the same operation as in Example 1 was performed to obtain 138 parts of a red colorant (RP-15).

[Example 16] (Production of red colorant (RP-16))
The same procedure as in Example 13 was performed, except that 111 parts of dinaphthol 13 was used instead of 82 parts of dinaphthol 1 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 mass%. Next, except that the azo pigment 16 was used instead of the azo pigment 1 used in Example 1, the same operation as in Example 1 was performed to obtain 138 parts of a red colorant (RP-16).

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

[Example 18] (Production of red colorant (RP-18))
166 parts of azo pigment 18 (mixture of A1-18 and A2-18) was prepared in the same manner as in Example 13, except that 95 parts of dinaphthol 5 was used instead of 82 parts of dinaphthol 1 used in Example 13. (Yield: 97.9%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-18 was 2.0 mass%. Subsequently, except having used the azo pigment 18 instead of the azo pigment 1 used in Example 1, it carried out similarly to Example 1 and obtained 138 parts of red coloring agents (RP-18).

[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%). As a result of LC-MS spectrum measurement, the content of A2-18 was 10.0% by mass. Subsequently, the same operation as in Example 1 was performed except that the azo pigment 19 was used instead of the azo pigment 1 used in Example 1, and 138 parts of a red colorant (RP-19) was obtained.

[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) 0.9%). As a result of LC-MS spectrum measurement, the content of A2-18 was 20.0% by mass. Next, except that the azo pigment 20 was used in place of the azo pigment 1 used in Example 1, the same operation as in Example 1 was performed to obtain 138 parts of a red colorant (RP-20).

<Method for producing pigment composition for color filter (A1 and A3)>
Below, the specific synthesis | combining method of the pigment composition containing an azo pigment (A1) and an azo pigment (A3) is shown. Other azo pigments according to the present invention can 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 cooled to −2 to 0 ° C. After adding 156 parts of 25% aqueous sodium nitrite solution to this solution, the mixture was stirred for 30 minutes while maintaining 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 a 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 a pH 5.4 acetate buffer solution over 10 minutes. After completion of the dropwise addition, the mixture was stirred at room temperature for 30 minutes, and further stirred while maintaining at 80 ° C., and the precipitated reaction product was filtered, washed with hot water, and dried to be an azo compound represented by the following formula (23) a 198 parts (yield: 98.0%) were obtained.

  To 1350 parts of N-methyl-2-pyrrolidone (NMP), 183 parts of an 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 dropwise addition, the mixture was refluxed for 2 hours. The reaction solution was added dropwise to a solution prepared by heating 35 parts of 2,5-dichloro-1,4-phenylenediamine and 2250 parts of N-methyl-2-pyrrolidone (NMP) at 85 ° C. over 1 hour, The mixture was heated to reflux for 4 hours. After cooling this reaction liquid to 95 ° C., 30 parts of 28% ammonia aqueous solution and 30 parts of water were added and stirred at 95-100 ° C. for 30 minutes. The precipitated reaction product was filtered, and N-methyl-2-pyrrolidone ( NMP), methanol, and hot water, followed by drying 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 mass%.

Formula (23)

  Next, except that the azo pigment 21 was used in place of the azo pigment 1 used in Example 1, the same operation as in Example 1 was performed to obtain 138 parts of a red colorant (RP-21).

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

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

<Method 2 for producing pigment composition for color filter (A1, A2)>
[Example 24] (Production of red colorant (RP-24))
Instead of 150 parts of the azo pigment 18 used in Example 18, 142.5 parts of the azo pigment 18 and 7.5 parts of the dye derivative represented by the formula (11-3) were used. Operation was performed to obtain 138 parts of a red colorant (RP-24).

[Example 25] (Production of red colorant (RP-25))
Instead of 150 parts of the azo pigment 18 used in Example 18, 142.5 parts of the azo pigment 18 and 7.5 parts of the dye derivative represented by the formula (12-3) were used. Operation was performed to obtain 138 parts of a red colorant (RP-25).

[Example 26] (Production of red colorant (RP-26))
Instead of 150 parts of the azo pigment 18 used in Example 18, 142.5 parts of the azo pigment 18 and 7.5 parts of the dye derivative represented by the formula (15-12) were used. Operation was performed to obtain 138 parts of a red colorant (RP-26).

[Example 27] (Production of red colorant (RP-27))
Instead of 150 parts of the azo pigment 18 used in Example 18, 142.5 parts of the azo pigment 18 and 7.5 parts of the dye derivative represented by the formula (18-5) were used. Operation was performed to obtain 138 parts of a red colorant (RP-27).

[Example 28] (Production of red colorant (RP-28))
Instead of 150 parts of azo pigment 18 used in Example 18, 142.5 parts of azo pigment 18 and 7.5 parts of the dye derivative represented by the formula (19-4) were used. Operation was performed to obtain 138 parts of a red colorant (RP-28).

[Example 29] (Production of red colorant (RP-29))
Instead of 150 parts of the azo pigment 18 used in Example 18, 142.5 parts of the azo pigment 18 and 7.5 parts of the dye derivative represented by the formula (19-5) were used. Operation was performed to obtain 138 parts of a red colorant (RP-29).

[Example 30] (Production of red colorant (RP-30))
Instead of 150 parts of the azo pigment 18 used in Example 18, 142.5 parts of the azo pigment 18 and 7.5 parts of the dye derivative represented by the formula (20-1) were used. Operation was performed to obtain 138 parts of a red colorant (RP-30).

[Example 31] (Production of red colorant (RP-31))
The same procedure as in Example 13 was performed, except that 882 parts of dinaphthol 6 was used instead of 82 parts of dinaphthol 1 used in Example 13, and 163 parts of azo pigment 24 (mixture of A1-19 and A2-19) (Yield: 96.3%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-19 was 2.0 mass%, and A2-19 was a mixture of A2-19a and A2-19b. Next, except that the azo pigment 24 was used in place of the azo pigment 1 used in Example 1, the same operation as in Example 1 was performed to obtain 138 parts of a red colorant (RP-31).

[Example 32] (Production of red colorant (RP-32))
The same procedure as in Example 13 was carried out, except that 91 parts of dinaphthol 4 was used instead of 82 parts of dinaphthol 1 used in Example 13, and 184 parts of azo pigment 25 (mixture of A1-20 and A2-20) (Yield: 97.0%) was obtained. As a result of LC-MS spectrum measurement, the content of A2-20 was 2.0 mass%, and A2-20 was a mixture of A2-20a and A2-20b. Subsequently, the same operation as in Example 1 was performed except that the azo pigment 25 was used instead of the azo pigment 1 used in Example 1, and 138 parts of a red colorant (RP-32) was obtained.

[Example 33] (Production of red colorant (RP-33))
174 parts of azo pigment 26 (mixture of A1-21 and A2-21) were carried out in the same manner as in Example 13 except that 794 parts of dinaphthol 1 was used instead of 82 parts of dinaphthol 1 used in Example 13. (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, except that the azo pigment 26 was used in place of the azo pigment 1 used in Example 1, the same operation as in Example 1 was performed to obtain 138 parts of a red colorant (RP-33).

[Example 34] (Production of red colorant (RP-34))
The same procedure as in Example 13 was performed, except that 101 parts of dinaphthol 9 was used instead of 82 parts of dinaphthol 1 used in Example 13, and 175 parts of azo pigment 27 (mixture of A1-22 and A2-22) (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. Subsequently, the same operation as in Example 1 was performed except that the azo pigment 27 was used in place of the azo pigment 1 used in Example 1, to obtain 138 parts of a red colorant (RP-34).

[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 were used, and dinaphthol 5 was changed from 95 parts to 83 parts. Except having changed, it carried out similarly to Example 18 and obtained 166 parts (yield: 97.7%) of azo pigment 28 (a mixture of A1-23 and A2-23). As a result of LC-MS spectrum measurement, the content of A2-23 was 2.0 mass%. Next, except that the azo pigment 28 was used in place of the azo pigment 1 used in Example 1, the same operation as in Example 1 was performed to obtain 138 parts of a red colorant (RP-35).

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

[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 were used and dinaphthol was used. Except that 5 was changed from 95 parts to 67 parts, the same operation as in Example 18 was performed to obtain 151 parts (yield: 97.0%) of azo pigment 30 (mixture of A1-25 and A2-25). It was. As a result of measuring the LC-MS spectrum, the content of A2-25 was 2.0% by mass. Next, except that the azo pigment 30 was used in place of the azo pigment 1 used in Example 1, the same operation as in Example 1 was performed to obtain 138 parts of a red colorant (RP-37).

[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 were used, and dinaphthol 5 was changed from 95 parts to 128 parts. Except for this, the same operation as in Example 18 was performed to obtain 151 parts (yield: 97.0%) of an 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, except that the azo pigment 31 was used in place of the azo pigment 1 used in Example 1, the same operation as in Example 1 was performed to obtain 138 parts of a red colorant (RP-38).

[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 were used, and dinaphthol 5 was changed from 95 parts to 104 parts. Except for this, the same operation as in Example 18 was performed to obtain 183 parts of azo pigment 32 (mixture of A1-27 and A2-27) (yield: 95.0%). As a result of LC-MS spectrum measurement, the content of A2-27 was 2.0% by mass. Next, except that the azo pigment 32 was used in place of the azo pigment 1 used in Example 1, the same operation as in Example 1 was performed to obtain 138 parts of a red colorant (RP-39).

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

[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, N-diethylbenzamide were used, and dinaphthol 5 was changed from 95 parts to 104 parts. Except having changed, it carried out similarly to Example 18 and obtained 182 parts (yield: 94.3%) of the azo pigment 34 (mixture of A1-29 and A2-29). As a result of LC-MS spectrum measurement, the content of A2-29 was 2.0% by mass. Next, except that the azo pigment 34 was used in place of the azo pigment 1 used in Example 1, the same operation as in Example 1 was performed to obtain 138 parts of a red colorant (RP-41).

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

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

<Method for producing pigment composition for comparative color filter>
[Comparative Example 1] (Production of red colorant (RP-44))
The same operation as in Example 21 was performed to obtain an 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 63 parts of thionyl chloride was added dropwise over 30 minutes. After completion of the dropwise addition, the mixture was refluxed for 2 hours. The above reaction solution was added dropwise to a solution prepared by separately heating 35 parts of 2,5-dichloro-1,4-phenylenediamine and 2250 parts of O-xylene at 85 ° C. over 1 hour, followed by heating under reflux for 4 hours. After cooling this reaction liquid to 95 ° C., 30 parts of 28% aqueous ammonia solution and 30 parts of water were added and stirred at 95-100 ° C. for 30 minutes, and then the precipitated reaction product was filtered to obtain O-xylene, methanol, and hot water. After washing with, dried to obtain 177 parts of azo pigment 37 (A1-18) (yield: 88.0%). As a result of LC-MS spectrum measurement, the content of A1-18 was 100% by mass. Next, except that the azo pigment 37 was used in place of the azo pigment 1 used in Example 1, the same operation as in Example 1 was performed to obtain 138 parts of a red colorant (RP-44).

[Comparative Example 2] (Production 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). 0.0%). As a result of LC-MS spectrum measurement, the content of A2-18 was 40.0% by mass. Next, except that the azo pigment 38 was used in place of the azo pigment 1 used in Example 1, the same operation as in Example 1 was performed to obtain 138 parts of a red colorant (RP-45).

[Comparative Example 3] (Production of red colorant (RP-46))
The same operation as in Example 21 was performed, 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 used. 161 parts (yield: 80.1%). As a result of LC-MS spectrum measurement, the content of A3-18 was 40.0% by mass. Subsequently, the same operation as in Example 1 was performed except that the azo pigment 39 was used in place of the azo pigment 1 used in Example 1, to obtain 138 parts of a red colorant (RP-46).

<Method for producing other red colorant>
[Production Example 15] (Production of red colorant (RP-47)): PR254
Commercially available C.I. I. 150 parts of Pigment Red 254 (PR254) (“Irga Fore Red B-CF” manufactured by BASF), 1500 parts of sodium chloride, and 250 parts of diethylene glycol were charged into a 1 gallon kneader (manufactured by Inoue Seisakusho Co., Ltd.) at 10 ° C. The mixture was kneaded for a time and subjected to salt milling. The obtained kneaded product was put into 5000 parts of warm water, stirred for 1 hour while heating to 70 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. 138 parts of a red colorant (RP-47) was obtained.

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

[Production Example 17] (Production of red colorant (RP-49)): PR242
C. I. Pigment Red 254 (“Irgafore Red B-CF” manufactured by BASF) I. Except having changed to pigment red 242 (PR242) (Sandorinscarlet 4RF made by Clariant), it carried out similarly to manufacture of a red coloring agent (RP-47), and obtained 138 parts of red coloring agents (RP-49).

[Production Example 18] (Production of red colorant (RP-50)): PR176
C. I. Pigment Red 254 (“Irgafore Red B-CF” manufactured by BASF) I. Pigment Red 176 (PR176) (“Novoperm Carmine HF3C” manufactured by Clariant) was used in the same manner as in the production of the red colorant (RP-47) to obtain 138 parts of a red colorant (RP-50). .

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

[Production Example 20] (Production of red colorant (RP-52)): Brominated diketopyrrolopyrrole pigment 200 parts of tert-amyl alcohol dehydrated with molecular sieves in a stainless steel reaction vessel equipped with a reflux tube in a nitrogen atmosphere And 140 parts of sodium-tert-amyl alkoxide were 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 dissolved by heating to 90 ° C. with stirring to prepare a solution of these mixtures. The heated solution of the mixture was slowly dropped into the alcoholate solution heated to 100 ° C. at a constant rate over 2 hours with vigorous stirring. After completion of the dropwise addition, heating and stirring were continued at 90 ° C. for 2 hours to obtain an alkali metal salt of a diketopyrrolopyrrole pigment. Furthermore, 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 cooled to -10 ° C. While cooling this mixture with a high-speed stirring disperser, rotating a shear disk having a diameter of 8 cm at 4000 rpm, the alkali metal salt of the diketopyrrolopyrrole pigment obtained above was cooled to 75 ° C. The solution was added in small portions. At this time, the rate of addition of the alkali metal salt of the diketopyrrolopyrrole pigment at 75 ° C. while cooling so that the temperature of the mixture consisting of methanol, acetic acid and water is always kept at −5 ° C. or lower. Was added in small portions over approximately 120 minutes. After addition of the alkali metal salt, red crystals were precipitated to form a red suspension. 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 re-dispersed in 3500 parts of methanol cooled to 0 ° C. to make a suspension with a methanol concentration of about 90%, and stirred at 5 ° C. for 3 hours to perform particle sizing and washing with crystal transition. Subsequently, the diketopyrrolopyrrole pigment aqueous paste obtained by filtration with an ultrafilter was dried at 80 ° C. for 24 hours and pulverized to obtain 150.8 parts of a brominated diketopyrrolopyrrole pigment. Got. C. I. Except for changing Pigment Red 254 ("Irgafore Red B-CF" manufactured by BASF) to a brominated diketopyrrolopyrrole pigment, it is carried out in the same manner as the production of the red colorant (RP-47), and 138 parts of red coloring An agent (RP-52) was obtained.

<Method for producing colored composition for color filter>
[Example 44] (Preparation of colored composition (RM-1))
A mixture having the following composition was stirred and mixed so as to be uniform, and then 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. It filtered with a 0.0 micrometer filter, and the coloring composition 1 (RM-1) was produced.
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 colored composition (RM-2 to 49))
The colored composition (RM-2 to 49) was the same as the colored composition (RM-1) except that the red colorant (RP-1) was changed to the pigment composition (red colorant) described in Table 3. ) Was produced.

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

(Dispersibility evaluation (viscosity characteristics))
About the obtained coloring composition, the initial viscosity in 25 degreeC was measured using the E-type viscosity meter ("ELD type viscosity meter" by the Toki Sangyo company). 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 time-dependent viscosity. The viscosity of the coloring composition was synonymous with dispersibility.
A: When the viscosity change rate is less than ± 5% and no sediment is formed. (Very good)
◯: When the viscosity change rate is ± 5% or more and less than ± 10%, and no precipitate is formed. (Good)
Δ: Viscosity change rate is ± 10% or more and less than 20%, and no sediment was formed. (Bad)
X: The case where the precipitate was produced even if the viscosity change rate was ± 20% or more or the viscosity change rate was less than ± 20%. (Very bad)

(Heat resistance evaluation)
The obtained colored composition was applied to 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, Subsequently, the coating-film board | substrate (one aspect | mode of a color filter) was produced by heating and cooling at 230 degreeC for 60 minute (s). The chromaticity ([L * (1), a * (1), b * (1)]) of the obtained coating film with a C light source was measured with a microspectrophotometer ("OSP-SP100" manufactured by Olympus Optical Co., Ltd.). And measured. Further, as a heat resistance test, the sample was heated at 250 ° C. for 1 hour, and the chromaticity ([L * (2), a * (2), b * (2)]) with a C light source was measured. The color difference ΔEab * was determined and evaluated in the following four stages.
ΔEab * = √ ((L * (2)-L * (1)) 2+ (a * (2)-a * (1)) 2+ (b * (2)-b * (1)) 2)
A: ΔEab * is less than 1.0 (very 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 (defect)
×: ΔEab * is 5.0 or more (very poor)

(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)]) with a C light source is measured with a microspectrophotometer (Olympus Optics) It measured using "OSP-SP100" by a company. Subsequently, an ultraviolet cut filter (“COLORED OPTICAL part LASS L38” manufactured by Hoya Co., Ltd.) was applied on the substrate, and irradiated with ultraviolet rays for 100 hours using a 470 W / m ² xenon lamp, and then the chromaticity ( [L * (2), a * (2), b * (2)]) were measured, and the color difference ΔEab * was determined by the above formula and evaluated according to the same criteria as heat resistance.

(Coating foreign material evaluation)
The obtained colored composition was applied to 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, Subsequently, the coating-film board | substrate was produced by heating at 230 degreeC for 60 minutes, and standing to cool. The evaluation was performed using a Olympus system metal microscope “BX60”). The magnification was 500 times, and the number of particles that were observable in arbitrary 5 fields of view through transmission was counted. Evaluation was made in the following four stages.
A: Less than 5 foreign objects (very good)
○: The number of foreign matters is 5 or more and less than 10 (good)
Δ: The number of foreign matters is 10 or more and less than 60 (defects)
×: The number of foreign matters is 60 or more (very bad)

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

<Method for producing photosensitive coloring composition for color filter>
First, a colored composition used by the photosensitive colored composition was prepared.

(Preparation of colored composition (RM-50)): PR254
A mixture having the following composition was stirred and mixed so as to be uniform, and then 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. It filtered with a 0.0 micrometer filter, and the coloring composition (RM-50) was produced.
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 colored composition (RM-51)): PR242
A colored composition (RM-51) was produced in the same manner as the colored composition (RM-50) except that the red colorant (RP-47) was changed to the red colorant (RP-49).

(Preparation of colored composition (RM-52)): Brominated diketopyrrolopyrrole pigment Colored composition (RM-50) except that the red colorant (RP-47) was changed to the red colorant (RP-52) A colored composition (RM-52) was prepared in the same manner as described above.

[Example 87] (Preparation of photosensitive coloring composition (RR-1))
A 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 colored composition (RR-1).
Colored composition (RM-1): 20.5 parts Colored 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 ("Irgacure 907" manufactured by BASF): 2.0 parts Sensitizer ("EAB-F" manufactured by Hodogaya Chemical Co., Ltd.): 0.4 parts Propylene glycol monomethyl ether Acetate: 43.6 parts

[Examples 88 to 131, Comparative Examples 10 to 26] (Photosensitive Coloring Composition (RR-2 to 62))
The ratio of the coloring composition to match the chromaticity of x = 0.640, y = 0.330 with the C light source at the time of coating film evaluation and the combination of the coloring composition shown in Table 5 (total amount of the coloring composition) A photosensitive colored composition (RR-2 to 62) was 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 filter>
Evaluation of the brightness | luminance (color characteristic) of the red coating film produced using the obtained photosensitive coloring composition was performed with the following method. Table 5 shows the evaluation results.

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

  From the results in Table 5, it was revealed that the examples using the colorant of the present invention were excellent in luminance in forming color filters. In particular, C.I. conventionally used as a bluish pigment. I. Pigment red 177 and C.I. I. By using it instead of Pigment Red 176, the effect of improving the brightness was confirmed.

<Production of color filter>
The green photosensitive coloring composition and the blue photosensitive coloring composition used for preparation of 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))
A mixture having the composition shown below was stirred and mixed uniformly, and 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 colored composition 1 (GM-1) was produced by filtering with a filter.
Green pigment (CI Pigment Green 36): 6.8 parts Yellow pigment (CI Pigment Yellow 150): 5.2 parts Resin-type dispersant ("EFKA4300" manufactured by BASF): 1.0 part Acrylic Resin solution 1: 35.0 parts Propylene glycol monomethyl ether acetate: 52.0 parts

Next, a 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 Toagosei Co., Ltd.): 2.8 parts Photopolymerization initiator ( "Irgacure 907" manufactured by BASF): 2.0 parts Sensitizer ("EAB-F" manufactured by Hodogaya Chemical Co., Ltd.): 0.4 parts Ethylene glycol monomethyl ether acetate: 39.6 parts

(Preparation of blue photosensitive coloring composition 1 (BR-1))
A mixture having the composition shown below was stirred and mixed uniformly, and 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 colored composition 1 (BM-1) was produced by filtering with a filter.
Blue pigment (CI Pigment Blue 15: 6): 7.2 parts Purple Pigment (CI Pigment Violet 23): 4.8 parts Resin-type dispersant ("EFKA4300" manufactured by BASF): 1.0 Parts Acrylic resin solution 1: 35.0 parts Propylene glycol monomethyl ether acetate: 52.0 parts

Next, a 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 Toagosei Co., Ltd.): 3.3 parts Photopolymerization initiator ( "Irgacure 907" manufactured by BASF): 2.0 parts Sensitizer ("EAB-F" manufactured by Hodogaya Chemical Co., Ltd.): 0.4 parts Ethylene glycol monomethyl ether acetate: 45.1 parts

(Production of color filter)
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 was irradiated with 300 mJ / cm ² of ultraviolet rays through a photomask using an ultrahigh pressure mercury lamp. Next, spray development was performed with an alkaline developer composed of a 0.2% by weight aqueous sodium carbonate solution to remove unexposed portions, followed by washing with ion-exchanged water. The substrate was heated at 230 ° C. for 20 minutes to obtain a red filter segment. Formed. The formed red filter segment was x = 0.640 and y = 0.330 with a C light source. By the same method, green photosensitive coloring composition 1 (GR-1) x = 0.300, y = 0.600, blue photosensitive coloring composition 1 (BR-1) x = 0.150, y = 0.060, a green filter segment and a blue filter segment were formed to obtain a color filter.

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

Claims (9)

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,
Total 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. Color filter pigment composition.
General formula (1)
[In General Formula (1), R _a 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 each 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 General Formula (2), R _a 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 each 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 General Formula (3), R _a 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 each 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), 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 color filters described in 1.   The pigment composition for a color filter according to claim 1 or 2, comprising an azo pigment (A1) represented by the general formula (1) and an azo pigment (A2) represented by the general formula (2).   Furthermore, the pigment composition for color filters as described in any one of Claims 1-3 containing a pigment derivative.   A color composition for a color filter comprising at least a colorant and a binder resin, wherein the colorant comprises 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, comprising at least one selected from the group consisting of Pigment Red 242 and a brominated diketopyrrolopyrrole pigment.   Furthermore, the coloring composition for color filters of Claim 5 or 6 containing at least 1 sort (s) chosen from the group which consists of a photopolymerizable monomer and a photoinitiator.   The color filter which comprises the filter segment formed from the coloring composition for color filters as described in any one of Claims 5-7 on a board | substrate. A method for producing a pigment composition for a color filter, comprising 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 General Formula (4), R _a 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 General Formula (5), X and Y are each independently 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 trifluoro Represents a methyl group. ]