JP2018145312A - Diketopyrrolopyrrole pigment composition, composition for color filter using the pigment composition, and color filter - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a diketopyrrolopyrrole pigment composition having excellent dispersibility and dispersion stability, causing no crystal deposition of the pigment in a heating process, and suitable for manufacturing a color filter having high lightness and high contrast.SOLUTION: The diketopyrrolopyrrole pigment composition comprises a diketopyrrolopyrrole pigment represented by formula (1), a diketopyrrolopyrrole pigment represented by formula (2), and a diketopyrrolopyrrole pigment represented by general formula (3), in which a mass ratio of the diketopyrrolopyrrole pigment represented by formula (1) to the diketopyrrolopyrrole pigment represented by formula (2) is 70:30 to 20:80. In a powder X-ray diffraction measurement using CuKα line, the diketopyrrolopyrrole pigment composition shows no maximum peak in the diffraction angle (2θ) range from 5 to 12°.SELECTED DRAWING: Figure 1

Description

  The present invention relates to a color liquid crystal display device, a color filter pigment composition for use in the production of a color filter used in a color imaging device and the like, a coloring composition, and a color filter formed using the same.

  In Patent Document 1, by using a brominated diketopyrrolopyrrole pigment and at least one diketopyrrolopyrrole pigment having a specific structural formula in combination, high crystallinity, high contrast, and crystal precipitation of the pigment due to the heating process are suppressed. A pigment composition for a color filter is disclosed. However, the market demand for improvement in optical characteristics in recent years is remarkable, and further improvement in brightness and contrast is required.

International Publication No. 2012/102399

  An object of the present invention is a diketopyrrolopyrrole pigment composition that has excellent dispersibility and dispersion stability and does not cause pigment crystal precipitation in the heating step, and is suitable for producing a color filter with high brightness and high contrast. Is to provide.

  As a result of extensive research, the present inventors have found that a brominated diketopyrrolopyrrole pigment, C.I. I. In the case of a pigment composition containing Pigment Red 254 and a diketopyrrolopyrrole pigment having an asymmetric substituent having a specific structure introduced at a specific ratio, each of the diketopyrrolopyrrole pigments contained alone exhibits a powder X-ray diffraction pattern Or a mixed crystal showing a specific powder X-ray diffraction pattern different from the superposition of those powder X-ray diffraction patterns. Surprisingly, the use of the diketopyrrolopyrrole pigment composition of the present invention in a pigment composition for a color filter is much higher than conventionally known diketopyrrolopyrrole pigments and diketopyrrolopyrrole pigment compositions. The present inventors have found that brightness and contrast are exhibited, and that other problems described above can be solved.

  That is, the present invention provides a diketopyrrolopyrrole pigment represented by the formula (1), a diketopyrrolopyrrole pigment represented by the formula (2), and a diketopyrrolopyrrole pigment represented by the general formula (3). It is a diketopyrrolopyrrole pigment composition to be contained, and the mass ratio of the diketopyrrolopyrrole pigment represented by the formula (1) and the diketopyrrolopyrrole pigment represented by the formula (2) is 70:30 to 20 And a diketopyrrolopyrrole pigment composition having no maximum peak in the range of diffraction angle (2θ) = 5 to 12 ° in powder X-ray diffraction using CuKα ray.

[In General Formula (3), R ¹ is a hydrogen atom, a halogen atom or a cyano group, and R ² and R ³ are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or a substituent. It may be a phenyl group. ]

  The present invention also provides the diketopyrrolopyrrole having a mass ratio of 50:50 to 20:80 of the diketopyrrolopyrrole pigment represented by formula (1) and the diketopyrrolopyrrole pigment represented by formula (2). The present invention relates to a pyrrole pigment composition.

  In the present invention, the diketopyrrolopyrrole pigment content represented by the general formula (3) is 1% by mass to 15% by mass with respect to the total amount of the diketopyrrolopyrrole pigment composition. The present invention relates to a pyrrole pigment composition.

  Moreover, this invention relates to the coloring composition for color filters containing the said diketopyrrolopyrrole pigment composition, binder resin, and the organic solvent.

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

  Furthermore, this invention relates to the color filter which comprises the filter segment formed from the said coloring composition for color filters.

  According to the present invention, a diketopyrrolopyrrole pigment composition that has excellent dispersibility and dispersion stability, and does not cause pigment crystal precipitation in the heating step, and is suitable for producing a color filter with high brightness and high contrast. Can be provided.

1 is an X-ray diffraction pattern of the diketopyrrolopyrrole pigment composition produced in Example 4. FIG. FIG. 2 is an X-ray diffraction pattern of the diketopyrrolopyrrole pigment produced in Comparative Example 1. FIG. 3 is an X-ray diffraction pattern of the diketopyrrolopyrrole pigment produced in Comparative Example 2. FIG. 4 is an X-ray diffraction pattern of the diketopyrrolopyrrole pigment composition produced in Comparative Example 11.

  Hereinafter, the present invention will be described in detail. Note that “CI” described below means a color index (CI).

<Diketopyrrolopyrrole pigment composition>
First, the diketopyrrolopyrrole pigment composition of the present invention will be described.
The diketopyrrolopyrrole pigment composition of the present invention is represented by the diketopyrrolopyrrole pigment represented by the following formula (1), the diketopyrrolopyrrole pigment represented by the following formula (2), and the general formula (3). Containing diketopyrrolopyrrole pigments.

[In General Formula (3), R ¹ is a hydrogen atom, a halogen atom or a cyano group, and R ² and R ³ are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or a substituent. It may be a phenyl group. ]

  Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Two or more kinds may be used in combination. Of these, a chlorine atom and a bromine atom are preferable.

R ¹ is preferably a hydrogen atom, a chlorine atom, or a bromine atom from the viewpoint of color characteristics, and the substitution position is preferably a para position.

  The alkyl group having 1 to 12 carbon atoms may be linear or branched, and is not particularly limited. However, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, Examples include tert-butyl group, pentyl group, hexyl group, heptyl group, octyl group, decyl group, dodecyl group, 1,5-dimethylhexyl group, 1,6-dimethylheptyl group, 2-ethylhexyl group and the like. From the point of contrast and the effect of suppressing crystal precipitation, an alkyl group having 4 to 8 carbon atoms is preferred.

  Examples of the phenyl group which may have a substituent include an alkyl group having 1 to 4 carbon atoms, a trifluoromethyl group, a halogen atom, a nitro group, a cyano group, a carbamoyl group, a sulfamoyl group, and an alkoxyl having 1 to 4 carbon atoms. And a phenyl group having a substituent such as a group. More specifically, phenyl group, p-methylphenyl group, 4-tert-butylphenyl group, p-nitrophenyl group, p-methoxyphenyl group, p-chlorophenyl group, 2,4-dichlorophenyl group, 3-carbamoyl A phenyl group and the like can be mentioned, but are not particularly limited. Among these, a phenyl group substituted with a halogen atom or an alkoxyl group having 1 to 4 carbon atoms or an unsubstituted phenyl group is preferable, and an unsubstituted phenyl group is more preferable.

R ² and R ³ are each independently preferably a hydrogen atom, a phenyl group or an alkyl group having 4 to 8 carbon atoms from the viewpoint of contrast and crystal precipitation suppression effect, and a hydrogen atom or an alkyl group having 4 to 8 carbon atoms. More preferably, it is a group.

  Specific examples of the diketopyrrolopyrrole pigment of the general formula (3) that can be used in the present invention are listed below, but are not limited thereto.

  The diketopyrrolopyrrole pigment represented by the formula (1) and the diketopyrrolopyrrole pigment represented by the formula (2) may be produced by a succinate synthesis method or various commercially available products may be used. it can. In the succinic acid ester synthesis method, 2 mol of 4-bromobenzonitrile or 2 mol of 4-chlorobenzonitrile is added to 1 mol of succinic acid diester in an inert organic solvent such as tert-amyl alcohol. In the presence of an alkali metal alkoxide, a condensation reaction is carried out at a high temperature of 80 to 110 ° C. to produce an alkali metal salt of a diketopyrrolopyrrole compound, and subsequently to the alkali metal salt of the diketopyrrolopyrrole compound, A diketopyrrolopyrrole pigment can be obtained by protonation with water, alcohol, acid or the like. At this time, the size of the primary particle diameter obtained can be controlled by the temperature in protonation, the type, ratio and amount of water, alcohol or acid. The production method of the diketopyrrolopyrrole pigment is not limited to this method.

  The diketopyrrolopyrrole pigment represented by the general formula (3) is described in, for example, the document Synth. Commun. , 1988, 18, 1213 and Tetrahedron, 58 (2002) 5457-5565. The production method of the diketopyrrolopyrrole pigment represented by the general formula (3) is not limited to this method.

  The diketopyrrolopyrrole pigment represented by the general formula (3) is a mixture of the diketopyrrolopyrrole pigment represented by the formula (1) or the diketopyrrolopyrrole pigment represented by the formula (2). Can also be synthesized. This can be achieved by utilizing a method using at least two structurally different benzonitrile compounds in the succinate synthesis method. Specifically, in the method described in International Publication No. 2009/081930, a plurality of benzonitrile compounds to be used are 4-bromobenzonitrile and a benzonitrile compound represented by the following general formula (4), or , 4-chlorobenzonitrile and a benzonitrile compound represented by the following general formula (4), whereby a diketopyrrolopyrrole pigment of the general formula (3) is mixed with a brominated diketopyrrolopyrrole pigment, or C. I. It can be manufactured as a mixture with Pigment Red 254.

[In General Formula (4), R ² and R ³ are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or a phenyl group which may have a substituent. ]

  The diketopyrrolopyrrole pigment composition of the present invention is characterized by having no maximum peak in a diffraction angle (2θ) = 5 to 12 ° in powder X-ray diffraction measurement using CuKα rays. Brominated diketopyrrolopyrrole pigments and C.I. I. In the diketopyrrolopyrrole pigment such as CI Pigment Red 254, the maximum peak in the diffraction angle (2θ) = 5 to 12 ° in the powder X-ray diffraction measurement using CuKα ray is (0 of the diketopyrrolopyrrole pigment crystal lattice. It is a signal indicating the crystallinity of the 20) plane. The diketopyrrolopyrrole pigment composition of the present invention can be obtained by any production method as long as it does not have a maximum peak in the range of diffraction angle (2θ) = 5 to 12 °. However, when a diketopyrrolopyrrole pigment composition is obtained by the method for producing a diketopyrrolopyrrole pigment composition described later, a diketopyrrolopyrrole pigment represented by formula (1), represented by formula (2). The coexistence of the diketopyrrolopyrrole pigment and the diketopyrrolopyrrole pigment represented by the general formula (3) results in a mixed crystal, and the crystallinity of the (0 20) plane is remarkably reduced, or (0 2 0 ) It is preferable because it does not have crystallinity in the plane direction and does not have a maximum peak in the range of diffraction angle (2θ) = 5 to 12 °.

  The diketopyrrolopyrrole pigment composition of the present invention has a mass ratio between the diketopyrrolopyrrole pigment represented by the formula (1) and the diketopyrrolopyrrole pigment represented by the formula (2) of 70:30 to 20:80. When the mass ratio of the diketopyrrolopyrrole pigment represented by the formula (1) exceeds 70% by mass, the contrast and the crystal precipitation suppressing effect are not sufficient. Moreover, when the mass ratio of the diketopyrrolopyrrole pigment represented by Formula (1) is less than 20 mass%, the brightness is not sufficient. At this time, the X-ray diffraction pattern of the diketopyrrolopyrrole pigment composition is obtained by the diketopyrrolopyrrole pigment represented by the formula (1) and the production method of the diketopyrrolopyrrole pigment composition described later and A mixed crystal having a specific X-ray diffraction pattern, which is a feature of the present invention, in which the respective X-ray diffraction patterns of the diketopyrrolopyrrole pigment represented by the formula (2) are superimposed according to the mass ratio. However, it has a maximum peak in the range of diffraction angle (2θ) = 5 to 12 °.

  That is, a diketo containing a diketopyrrolopyrrole pigment represented by formula (1), a diketopyrrolopyrrole pigment represented by formula (2), and a diketopyrrolopyrrole pigment represented by formula (3) In the pyrrolopyrrole pigment composition, the diketopyrrolopyrrole pigment represented by the formula (1) and the diketo represented by the formula (2) preferably in the production process of the diketopyrrolopyrrole pigment composition described later. When the mass ratio with the pyrrolopyrrole pigment is 70:30 to 20:80, a mixed crystal having no maximum peak in the range of diffraction angle (2θ) = 5 to 12 ° in X-ray diffraction measurement is obtained. It is possible to obtain a diketopyrrolopyrrole pigment composition that does not cause crystal precipitation of the pigment in a high degree, high contrast, and heating process. In order to further increase the contrast ratio within the range not impairing the brightness, the mass ratio of the diketopyrrolopyrrole pigment represented by the formula (1) and the diketopyrrolopyrrole pigment represented by the formula (2) is 50 : It is preferable that it is 50-20: 80.

  In the diketopyrrolopyrrole pigment composition of the present invention, the content of the diketopyrrolopyrrole pigment represented by the general formula (3) is preferably 1% by mass to 15% with respect to the total amount of the diketopyrrolopyrrole pigment composition. It is mass%, More preferably, it is 3 mass%-10 mass%. It is preferable that the content of the diketopyrrolopyrrole pigment represented by the general formula (3) is 1% by mass or more and 15% by mass or less because the contrast, the crystal precipitation suppressing effect, and the brightness are all good.

  In the diketopyrrolopyrrole pigment composition of the present invention, a diketopyrrolopyrrole pigment represented by formula (1), a diketopyrrolopyrrole pigment represented by formula (2), and a dike represented by formula (3) The mass ratio of the ketopyrrolopyrrole pigment can be analyzed using HPLC, TOF-MASS, FD-MASS, LC-MASS or NMR. Alternatively, as disclosed in JP-A-08-199085, a diketopyrrolopyrrole pigment composition is obtained by stirring at room temperature with di-tert-butyl dicarbonate and 4-dimethylaminopyridine in tetrahydrofuran. After conversion to a soluble diketopyrrolopyrrole compound, analysis using NMR, MASS, LC-MASS, or the like may be performed. Alternatively, the above analysis may be performed after the hydrogen of the NH group of the pyrrolopyrrole ring is substituted with an alkyl group using an alkyl halide or the like and converted into a soluble diketopyrrolopyrrole compound.

(Dye derivative)
In the diketopyrrolopyrrole pigment composition of the present invention, a dye derivative can be used for the purpose of suppressing pigment crystal growth and improving pigment dispersibility. Examples of the dye derivatives used in the present invention include diketopyrrolopyrrole derivatives, benzoisoindole derivatives, anthraquinone derivatives, dianthraquinone derivatives, thiazine indigo derivatives, azo dye derivatives, quinophthalone derivatives, and quinacridone derivatives. Examples of the structure of the dye derivative include, but are not limited to, the dye derivative represented by the following formula (5).
P-Lm Formula (5)
[In the formula (5), P represents a diketopyrrolopyrrole residue, a benzoisoindole residue, an anthraquinone residue, a dianthraquinone residue, a thiazineindigo residue, an azo dye residue, a quinophthalone residue, or a quinacridone residue. M is an integer of 1 to 4, L is independently —OH; —SO ₃ H, —COOH, monovalent to trivalent metal salts of these acidic groups, alkylammonium salts A phthalimidomethyl group which may have a substituent; a group represented by the following formula (a), (b), (c), (d), (e), or (f); _{-SO 2 -, - CO -,} - CH 2 -, - CH 2 NHCOCH 2 -, - CH 2 NHSO 2 CH 2 -, or a direct bond, Y is, -NH -, - O -, - S- Or a direct bond, n is an integer from 1 to 10, R ₁₆ and R ₁₇ are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 30 carbon atoms, an optionally substituted alkenyl group having 2 to 30 carbon atoms, or R ₁₆ and R ₁₇ are a heterocyclic ring which may have a substituent, and further contains a nitrogen, oxygen or sulfur atom, and R ₁₈ , R ₁₉ , R ₂₀ , R ₂₁ and R _22. Are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted alkenyl group having 2 to 20 carbon atoms, and R ₂₃ is The substituent is represented by the formula (a) or the formula (b), and R ₂₄ is a chlorine atom, -OH, an alkoxyl group, a substituent represented by the formula (a) or the formula (b). , Z represents —CONH—, —NHCO—, —SO ₂ NH—, or —NHSO ₂ —. R ₂₅ is a hydrogen atom, —NH ₂ , —NHCOCH ₃ , —NHR ₂₆ , or a substituent represented by the formula (c), wherein R ₂₆ is a carbon that may have a substituent. It is a C2-C20 alkenyl group which may have a C1-C20 alkyl group and a substituent. ]

  Examples of the monovalent to trivalent metal include sodium, potassium, magnesium, calcium, iron, and aluminum. Examples of the alkylammonium salt include ammonium salts of long-chain monoalkylamines such as octylamine, laurylamine, and stearylamine, or palmityltrimethylammonium salt, dilauryldimethylammonium salt, and distearyldimethylammonium salt. A quaternary alkyl ammonium salt is mentioned.

  As the phthalimidomethyl group which may have a substituent, the alkyl group which may have a substituent, the alkenyl group which may have a substituent, or the heterocyclic substituent which may have a substituent, , Halogen atoms, nitro groups, cyano groups, carbamoyl groups, N-substituted carbamoyl groups, sulfamoyl groups, N-substituted sulfamoyl groups, alkoxy groups having 1 to 20 carbon atoms, alkylthio groups having 1 to 20 carbon atoms, and the like. However, it is not limited to these.

  The dye derivative is a sulfonation reaction by heating in sulfuric acid or fuming sulfuric acid, a phthalimide methylation reaction in which dehydration condensation with N-hydroxymethylphthalimide is carried out in sulfuric acid, and chlorosulfonated using chlorosulfonic acid and thionyl chloride, It is synthesized by a known production method such as sulfonamidation reaction in which an amine component such as dimethylaminopropylamine is reacted.

  Examples of the amine component used to form the substituent represented by the above formula (a), formula (b), and formula (c) include dimethylamine, diethylamine, methylethylamine, N, N-ethyl. Isopropylamine, N, N-ethylpropylamine, N, N-methylbutylamine, N, N-methylisobutylamine, N, N-butylethylamine, N, N-tert-butylethylamine, diisopropylamine, dipropylamine, N , Nsec-butylpropylamine, dibutylamine, di-sec-butylamine, diisobutylamine, N, N-isobutyl-sec-butylamine, diamylamine, diisoamylamine, dihexylamine, dicyclohexylamine, di (2-ethylhexyl) amine , Dioctylamine, N, N- Tyloctadecylamine, didecylamine, diallylamine, N, N-ethyl-1,2-dimethylpropylamine, N, N-methylhexylamine, dioleylamine, distearylamine, N, N-dimethylaminomethylamine, N, N- Dimethylaminoethylamine, N, N-dimethylaminoamylamine, N, N-dimethylaminobutylamine, N, N-diethylaminoethylamine, N, N-diethylaminopropylamine, N, N-diethylaminohexylamine, N, N-diethylaminobutylamine N, N-diethylaminopentylamine, N, N-dipropylaminobutylamine, N, N-dibutylaminopropylamine, N, N-dibutylaminoethylamine, N, N-dibutylaminobutylamine, N, N-diiso Tylaminopentylamine, N, N-methyl-laurylaminopropylamine, N, N-ethyl-hexylaminoethylamine, N, N-distearylaminoethylamine, N, N-dioleylaminoethylamine, N, N-distearyl Aminobutylamine, piperidine, 2-pipecoline, 3-pipecoline, 4-pipecoline, 2,4-lupetidine, 2,6-lupetidine, 3,5-lupetidine, 3-piperidinemethanol, pipecolic acid, isonipecotic acid, methyl isonipecotate , Ethyl isonipecotate, 2-piperidineethanol, pyrrolidine, 3-hydroxypyrrolidine, N-aminoethylpiperidine, N-aminoethyl-4-pipecoline, N-aminoethylmorpholine, N-aminopropylpiperidine, N-aminopropyl- -Pipecoline, N-aminopropyl-4-pipecoline, N-aminopropylmorpholine, N-methylpiperazine, N-butylpiperazine, N-methylhomopiperazine, 1-cyclopentylpiperazine, 1-amino-4-methylpiperazine, 1- Examples thereof include, but are not limited to, cyclopentylpiperazine.

  In addition, when a substituent is introduced into the azo dye, the azo dye derivative can be produced by introducing the substituent into a diazo component or a coupling component in advance and then performing a coupling reaction.

  In addition to the method of mixing the diketopyrrolopyrrole pigment with the pigment when it is dispersed in the pigment carrier, the method of using the pigment derivative is a method of mixing in water or an organic solvent at the time of pigment production, or co-dissolving at the time of dissolution precipitation. Examples thereof include a method for precipitation and a method for addition during wet kneading. The method of mixing the dye derivative in water or an organic solvent at the time of pigment production, the method of co-precipitation at the time of dissolution precipitation, and the method of adding at the time of wet kneading express the effect of suppressing the crystal growth of the diketopyrrolopyrrole pigment, In order to exhibit the effect of suppressing crystal growth, it is required that the dye derivative is efficiently adsorbed on the surface of the diketopyrrolopyrrole pigment and is not easily desorbed. For this reason, the structure of the pigment derivative is often considered to have a partial chemical structure similar to the pigment used. For these reasons, when producing a diketopyrrolopyrrole pigment, a dye derivative having a diketopyrrolopyrrole structure, a thiazineindigo structure, a benzoisoindole structure, or a quinacridone structure is generally effective. is there.

  Moreover, when using a pigment derivative, it is required not to impair the color tone of the diketopyrrolopyrrole pigment as much as possible. From the viewpoint of hue, it is preferable to use a diketopyrrolopyrrole derivative, a benzoisoindole derivative, a thiazineindigo derivative, an azo dye derivative, or a quinophthalone derivative that exhibits yellow, orange, and red.

  The blending amount of the pigment derivative is preferably in the range of 0.5 to 40% by mass based on the total amount of the pigment composition (100% by mass). More preferably, it is the range of 3-35 mass%. When the amount is 0.5% by mass or less, the crystal growth suppressing effect is not sufficient, and when it is 40% by mass or more, the good color tone of the diketopyrrolopyrrole pigment is impaired.

  Hereinafter, although the specific example of the pigment derivative used for this invention is described, it is not limited to these.

(Specific examples of diketopyrrolopyrrole derivatives)
As the diketopyrrolopyrrole derivative, specifically, a compound represented by the following formula (6) or formula (7) can be used, but is not limited thereto.

(Specific examples of benzoisoindole derivatives)
As the benzoisoindole derivative, specifically, a compound represented by the following formula (8) can be used, but is not limited thereto.

(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, a compound represented by the following formula (12), formula (13), or formula (14) can be used, but it is not limited thereto.

(Specific examples of quinophthalone derivatives)
As the quinophthalone derivative, specifically, compounds represented by the following formulas (15-1) to (15-17) 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.

<Method for producing diketopyrrolopyrrole pigment composition>
When the diketopyrrolopyrrole pigment composition of the present invention is subjected to a known pigmentation step (also referred to as conditioning or finishing step), the diketopyrrolopyrrole pigment represented by the formula (1), the formula (2) ) And a diketopyrrolopyrrole pigment represented by the formula (3) can coexist. Alternatively, the diketopyrrolopyrrole pigment composition of the present invention precipitates pigment particles by protonating an alkali metal salt of a diketopyrrolopyrrole compound in the course of a succinate synthesis method for producing a diketopyrrolopyrrole pigment. In the process of making it, it can obtain also by mixing the metal salt of the diketopyrrolopyrrole pigment represented by Formula (1)-Formula (3). For example, the diketopyrrolopyrrole pigment represented by the formula (1) was adjusted separately for the metal salt of the diketopyrrolopyrrole pigment represented by the formula (1) obtained in the process of producing the succinate ester synthesis method. A metal salt of a diketopyrrolopyrrole pigment represented by formula (2) and a metal salt of a diketopyrrolopyrrole pigment represented by formula (3) are mixed, and water, alcohol, The diketopyrrolopyrrole pigment composition of the present invention in the form of a mixed crystal can be obtained by protonation using an acid or the like. At this time, a pigmentation step may be further added to the water-containing cake or dried product of the obtained diketopyrrolopyrrole pigment composition.

  Known pigmentation processes include a salt milling process in which a water-soluble inorganic salt and a water-soluble organic solvent are added to the pigment and kneaded, a solvent heating process in which the pigment is heated and stirred in the presence of the organic solvent, and the pigment is dissolved in a good solvent. For example, a dissolution and precipitation treatment in which the precipitate is reprecipitated with a poor solvent. In the diketopyrrolopyrrole pigment composition of the present invention, a salt milling treatment or a dissolution precipitation treatment is preferably performed, and a salt milling treatment is more preferably performed.

  Salt milling is a process of heating a mixture of pigment, water-soluble inorganic salt and water-soluble organic solvent using a kneader such as a kneader, trimix, two-roll mill, three-roll mill, ball mill, attritor or sand mill. Then, after mechanically 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 considered 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. Therefore, the crushing of the pigment and the crystal growth occur simultaneously during kneading, and the primary particle diameter of the pigment obtained varies depending on the kneading conditions.

  In order to promote crystal growth by heating, the heating temperature is preferably 35 to 150 ° C. When the heating temperature is less than 35 ° C., crystal growth does not occur sufficiently, and the shape of the pigment particles becomes undesirably close to amorphous. On the other hand, when the heating temperature exceeds 150 ° C., crystal growth proceeds excessively and the primary particle diameter of the pigment increases, which is not preferable as a colorant for a color filter. The kneading time for the salt milling treatment is preferably 2 to 24 hours from the viewpoint of the balance between the particle size distribution of the primary particles of the salt milling treatment pigment and the cost required for the salt milling treatment.

  By optimizing the conditions for salt milling the pigment, a pigment having a very fine primary particle diameter, a narrow distribution width, and a sharp particle size distribution can be obtained.

  As the water-soluble inorganic salt used for the salt milling treatment, 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% by mass, more preferably 300 to 1200% by mass, based on the total amount of the pigment composition (100% by mass) from the viewpoint of both processing efficiency and production efficiency.

  The water-soluble organic solvent is not particularly limited as long as it functions to wet the pigment and the water-soluble inorganic salt and dissolves (mixes) in water and does not substantially dissolve the inorganic salt to be used. However, a high boiling point solvent having a boiling point of 120 ° C. or higher is preferable from the viewpoint of safety because the temperature rises during salt milling and the solvent is easily evaporated.

  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 and the like are used. The water-soluble organic solvent is preferably used in an amount of 5 to 1000 parts by weight, more preferably 50 to 500 parts by weight, with respect to 100 parts by weight of the pigment composition.

  When carrying out the salt milling treatment, the above-mentioned dye derivative may be used in combination to improve the kneading efficiency, which is very effective for making the pigment finer and sized. In the refinement of the diketopyrrolopyrrole pigment composition of the present invention, it is preferable to use the dye derivative, but the invention is not limited thereto. The amount of the dye derivative used is preferably in the range of 0.5 to 40% by mass, which does not affect the color tone, that is, based on the total amount of the pigment composition (100% by mass).

  Moreover, when performing a salt milling process, you may add resin as needed. The kind of resin used is not particularly limited as in the case of dissolution and precipitation, 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 organic solvent. It is preferable that the usage-amount of resin is the range of 5-200 mass parts with respect to 100 mass parts of pigment compositions.

  Moreover, when performing a salt milling process, you may contain additives, such as a resin type dispersing agent and / or surfactant, as needed. Although the kind of additive is not specifically limited, The resin type dispersing agent and / or surfactant which are mentioned later are used preferably. The amount used when adding the resin-type dispersant and the surfactant is 100 parts by mass of the pigment composition, preferably 0.1 to 55 parts by mass, and more preferably 0.1 to 45 parts by mass.

  The dissolution precipitation treatment is a treatment in which the pigment is once dissolved with a good solvent, diluted with a large amount of poor solvent and reprecipitated, and then the solvent is filtered off or distilled off.

  Here, the good solvent is not particularly limited as long as it can dissolve the diketopyrrolopyrrole pigment composition, but inorganic acids (sulfuric acid, fuming sulfuric acid, chlorosulfonic acid, hydrochloric acid, phosphoric acid, etc.), aqueous solutions thereof, organic acids ( Dichloroacetic acid, methanesulfonic acid, etc.), inorganic bases (sodium hydroxide, potassium hydroxide, calcium hydroxide, etc.) and their aqueous solutions, organic bases (triethylamine, diazabicycloundecene, sodium methoxide, etc.), alcohol solvents ( Methanol, n-propanol, tert-amyl alcohol, etc.), ketone solvents (methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, etc.), ether solvents (tetrahydrofuran, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, etc.), sulfoxy Solvent (dimethyl sulfoxide, hexamethylene sulfoxide, sulfolane, etc.), ester solvent (ethyl acetate, acetic acid-n-butyl, ethyl lactate, etc.), amide solvent (N, N-dimethylformamide, 1-methyl-2- Pyrrolidone, etc.), aromatic hydrocarbon solvents (toluene, xylene, etc.), aliphatic hydrocarbon solvents (octane, etc.), nitrile solvents (acetonitrile, etc.), halogen solvents (carbon tetrachloride, dichloromethane, etc.), ionic A liquid (1-ethyl-3-methylimidazolium tetrafluoroborate or the like), a carbon disulfide solvent, or a mixture thereof can be given. The amount of the good solvent used is not particularly limited as long as it is an amount capable of dissolving the diketopyrrolopyrrole pigment composition, but from the viewpoint of industrial economy, the total amount of the pigment composition is 100 (mass%) as a standard. It is preferable that it is -5000 mass%, and it is more preferable that it is 500-3000 mass%.

  The temperature at which the pigment composition is dissolved is preferably -10 to 200 ° C, more preferably -10 to 130 ° C, and further preferably -10 to 100 ° C.

  The poor solvent is not particularly limited as long as the diketopyrrolopyrrole pigment composition is precipitated when mixed with a solution containing the diketopyrrolopyrrole pigment composition dissolved in a good solvent. Suitable examples include water, hydrochloric acid, aqueous sodium hydroxide, and the like. The amount of the poor solvent used is preferably 50 to 5000 parts by mass and 100 to 3000 parts by mass with respect to 100 parts by mass of the solution containing the diketopyrrolopyrrole pigment composition from the viewpoint of industrial economy. It is more preferable.

  The temperature at the time of precipitation is preferably −10 to 150 ° C., more preferably −5 to 130 ° C., and further preferably 0 to 100 ° C.

  By optimizing the conditions for dissolving and precipitating the pigment, a pigment having a very fine primary particle diameter, a narrow distribution width, and a sharp particle size distribution can be obtained.

  Moreover, when carrying out dissolution precipitation, a pigment derivative may be used in combination as appropriate, which is effective for making the pigment finer (fine particles) and adjusting the particle size. In the refinement of the diketopyrrolopyrrole pigment composition of the present invention, it is preferable to use the dye derivative, but the invention is not limited thereto. The amount of the dye derivative used is preferably in the range of 0.5 to 40% by mass, which does not affect the color tone, that is, based on the total amount of the pigment composition (100% by mass).

  Moreover, when performing melt | dissolution precipitation, you may add resin as needed. 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 organic solvent. It is preferable that the usage-amount of resin is the range of 5-200 mass parts with respect to 100 mass parts of pigment compositions.

  Moreover, when performing melt | dissolution precipitation, you may contain additives, such as a resin type dispersing agent and / or surfactant, as needed. Although the kind of additive is not specifically limited, The resin type dispersing agent and / or surfactant which are mentioned later are used preferably. The amount used when adding the resin-type dispersant and the surfactant is 100 parts by mass of the pigment composition, preferably 0.1 to 55 parts by mass, and more preferably 0.1 to 45 parts by mass.

  The diketopyrrolopyrrole pigment composition of the present invention can be used as a colored composition when used in combination with a binder resin and an organic solvent. Moreover, you may use together coloring agents other than the diketopyrrolopyrrole pigment composition of this invention.

<Other colorants>
The coloring composition of the present invention may be used in combination with other colorants such as pigments and dyes other than the diketopyrrolopyrrole pigment composition of the present invention in order to adjust the chromaticity. Specific examples of other colorants are shown 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 colorants to be used in combination are C.I. I. Pigment red 177, 254, 242, C.I. I. Pigment yellow 139, 150, and 185.

  When a colorant other than the diketopyrrolopyrrole pigment is used in combination, the diketopyrrolopyrrole pigment composition of the present invention is preferably in the range of 40% by mass to 100% by mass in the total amount of the colorant (100% by mass). . More preferably, it is the range of 60 mass%-100 mass%.

<Binder resin>
Examples of the binder resin contained in the colored composition 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 ethoxypoly (Meth) acrylates such as tylene glycol (meth) acrylate, or (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, dye (Meth) acrylamides such as acetone (meth) acrylamide or acryloylmorpholine, styrenes such as styrene or α-methylstyrene, ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, or isobutyl vinyl ether Examples thereof include vinyl ethers, vinyl acetate, and fatty acid vinyls such as vinyl propionate.

  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-sc N-imidyl-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.

  Examples of the thermosetting resin include epoxy resins, benzoguanamine resins, rosin-modified maleic acid resins, rosin-modified fumaric acid resins, melamine resins, urea resins, and phenol resins. Especially, an epoxy resin and a melamine resin are used more suitably from a viewpoint of heat resistance improvement.

  The weight average molecular weight (Mw) of the binder resin is preferably in the range of 5,000 to 80,000, more preferably in the range of 7,000 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 40,000, 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 the binder resin is used as a coloring composition for a color filter, an aliphatic group and an aromatic group which act as an affinity group for a pigment adsorbing group and an alkali-soluble group during development, a pigment carrier and a solvent. The balance is important for pigment 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, a fine pattern does not remain by development.

  The binder resin can be used in an amount of 20 to 500% by mass based on the total mass of the colorant. If it is less than 20% by mass, the film formability and various resistances are insufficient, and if it exceeds 500% by mass, the pigment concentration is low and color characteristics cannot be expressed.

<Organic solvent>
In the colored composition of the present invention, the pigment is sufficiently dispersed in a pigment carrier, and applied to a glass substrate or the like so as to have a dry film thickness of 0.2 to 5 μm to form a filter segment. In order to facilitate, an organic solvent is included. The organic solvent is selected in consideration of good applicability of the coloring composition, solubility of each component of the coloring composition, and 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 dibutyl 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, dipropylene glycol monomethyl ether, diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene glycol Monoethyl ether, propylene glycol monoethyl ether 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, Louis Seo ketone, methyl cyclohexanol, acetic acid n- amyl acetate n- butyl, isoamyl acetate, isobutyl acetate, propyl acetate, and dibasic acid esters.

  Among them, since the solubility of each component of the coloring composition and the coating property of the coloring composition are good, ethyl lactate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl It is preferable to use glycol acetates such as ether acetate, aromatic alcohols such as benzyl alcohol, and ketones such as cyclohexanone.

  These organic solvents can be used individually by 1 type or in mixture of 2 or more types. Moreover, since the organic solvent can adjust the coloring composition to an appropriate viscosity and can form a filter segment with a desired uniform film thickness, the total mass of the colorant is based on 100 mass%, and is 500 to 4000 mass. % Is preferably used.

<Pigment dispersion>
In the coloring composition of the present invention, the diketopyrrolopyrrole pigment composition of the present invention is mixed with a kneader, a two-roll mill, a three-roll mill, a ball mill, a horizontal sand mill, in a colorant carrier composed of the binder resin and an organic solvent. It can be produced by finely dispersing using various dispersing means such as a vertical sand mill, an annular bead mill, or an attritor. In addition, the colored composition of the present invention may be prepared by dispersing the diketopyrrolopyrrole pigment composition of the present invention and other colorants at the same time in a colorant carrier, or by mixing separately dispersed in a colorant carrier. You may do it.

  Further, when the colorant is dispersed in the colorant carrier, a dispersion aid such as the above-described dye derivative, resin-type dispersant, surfactant, or the like may be appropriately contained. Since the dispersion aid has a great effect of preventing re-aggregation of the colorant after dispersion, the color composition obtained by dispersing the colorant in the colorant carrier using the dispersion aid has contrast and viscosity stability. Become good.

(Resin type dispersant and surfactant)
The resin-type dispersant has a pigment-affinity part having a property of adsorbing to the colorant and a part compatible with the colorant carrier, and adsorbs to the colorant to disperse the colorant to the colorant carrier. It works to stabilize. Specific examples of resin-type dispersants include polycarboxylic acid esters such as polyurethane and polyacrylate, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, and polycarboxylic acid alkylamine salts. , Polysiloxane, long-chain polyaminoamide phosphate, hydroxyl group-containing polycarboxylic acid ester, modified products thereof, amides formed by reaction of poly (lower alkyleneimine) and polyester having a free carboxyl group, and salts thereof Oil-soluble dispersants such as, (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylic acid ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol, polyvinylpyrrolidone, etc. Resin, water-soluble polymer, polyester, modified poly Acrylate-based, ethylene oxide / propylene oxide addition compound, phosphate ester-based and the like are used, they can be used alone or in admixture of two or more, not necessarily limited thereto.

  Commercially available resin-type dispersants include Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, and 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 -SOLPERSE-3000, 9000, 13000, 13240, 13650, 13940, 160 manufactured by Nippon Lubrizol Corporation, such as P104, P104S, 220S, 6919, or Lactimon, Lactimon-WS or Bykumen, etc. 0, 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, 31845, 32000, 32500, 32550, 33500, 32600, 34750, 35100, 36600, 38500, 41000, 41090, 53095, 55000, 76500, etc., 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 1101,120,150,1501,1502,1503, etc., Ajinomoto Fine-Techno Co., Ltd. of AJISPER PA111, PB711, PB821, PB822, PB824, and the like.

  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 lauryl sulfate monoethanolamine, lauryl sulfate triethanolamine, ammonium lauryl sulfate, monoethanolamine stearate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate; 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.

  In the case of adding a resin-type dispersant and a surfactant, the total amount of the colorant is based on (100% by mass), preferably 0.1 to 55% by mass, more preferably 0.1 to 45% by mass. . When the blending amount of the resin-type dispersant and the surfactant is less than 0.1% by mass, it is difficult to obtain the added effect. When the blending amount is more than 55% by mass, the dispersion is affected by an excessive dispersant. May affect.

  The colored composition of the present invention can be used as a photosensitive colored composition by further adding a photopolymerizable monomer and / or a photopolymerization initiator.

<Photopolymerizable monomer>
Photopolymerizable monomers that may be used in the photosensitive coloring composition include monomers or oligomers that are cured by ultraviolet rays or heat to produce a transparent resin, which are used alone or in combination of two or more. Can be used. 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>
In the photosensitive coloring composition, when the composition is cured by ultraviolet irradiation and a filter segment is formed by a photolithographic method, a photopolymerization initiator is added in the form of a solvent development type or alkali development type colored resist material. Can be adjusted.

  Examples of the photopolymerization initiator include 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1- Hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1 Acetophenone compounds such as-[4- (4-morpholinyl) phenyl] -1-butanone or 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one; benzoin, benzoin Methyl ether, benzoin ethyl ether, benzoin isopropyl ether, or Benzoin compounds such as dimethyl dimethyl ketal; benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, or 3,3 ', 4 Benzophenone compounds such as 4,4'-tetra (t-butylperoxycarbonyl) benzophenone; thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, 2,4-diethylthioxanthone, etc. 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxy) Phenyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine, 2-piperonyl-4,6-bis (trichloro) Methyl) -s-triazine, 2,4-bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2 -(4-Methoxy-naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl- (piperonyl) -6-triazine, or 2,4-trichloromethyl- Triazine compounds such as (4′-methoxystyryl) -6-triazine; 1,2-octanedione, 1- [4- (phenylthio)-, 2- (O-benzoyloxime) )], Or oxime ester compounds such as O- (acetyl) -N- (1-phenyl-2-oxo-2- (4′-methoxy-naphthyl) ethylidene) hydroxylamine; bis (2,4,6- Phosphine compounds such as trimethylbenzoyl) phenylphosphine oxide or 2,4,6-trimethylbenzoyldiphenylphosphine oxide; quinone compounds such as 9,10-phenanthrenequinone, camphorquinone and ethylanthraquinone; borate compounds; carbazole A imidazole compound; a titanocene compound, or the like.

  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 mass based on the total amount of the colorant in the photosensitive coloring composition (100% by mass), and 3 to 3 from the viewpoint of photocurability and developability. More preferably, it is 150 mass%.

<Sensitizer>
Furthermore, the photosensitive coloring composition 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, and other polymethine dyes, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, Azulene derivatives, azurenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, tetrabenzoporphyrin derivatives, Trapirazinoporphyrazine derivatives, phthalocyanine derivatives, tetraazaporphyrazine derivatives, tetraquinoxalyloporphyrazine derivatives, naphthalocyanine derivatives, subphthalocyanine derivatives, pyrylium derivatives, thiopyrylium derivatives, tetraphylline derivatives, annulene derivatives, spiropyran derivatives, spirooxazine 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 mass, based on the total weight (100% by mass) of the photopolymerization initiator contained in the photosensitive coloring composition, and is photocured. Is more preferably 5 to 50% by mass from the viewpoint of the property and developability.

<Amine compound>
In addition, the coloring composition or the photosensitive coloring composition can contain an amine compound that functions to reduce 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 or the photosensitive coloring composition. 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-310 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. The content of the leveling agent is usually preferably 0.003 to 0.5% by mass based on the total weight of the colored composition or the photosensitive colored composition (100% by mass).

  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>
In order to assist the curing of the thermosetting resin, the coloring composition or the photosensitive coloring composition may contain a curing agent, a curing accelerator, and the like as necessary. As the curing agent, phenolic 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- Til-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, 0.01-15 mass% is preferable with respect to thermosetting resin whole quantity (100 mass%).

<Other additive components>
The coloring composition or the photosensitive coloring composition may contain a storage stabilizer in order to stabilize the viscosity with time. 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 mass based on the total amount of the colorant (100% by mass).

  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 is used in an amount of 0.01 to 10% by mass, preferably 0.05 to 5% by mass, based on the total amount of the colorant in the colored composition or photosensitive coloring composition (100% by mass). be able to.

<Removal of coarse particles>
The coloring composition and the photosensitive coloring composition are 5 μm or more coarse particles, preferably 1 μm or more coarse particles, more preferably 0.5 μm or more by means of centrifugation, filtration with a sintered filter or a membrane filter, or the like. It is preferable to remove coarse particles and 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 is 0.3 μm or less.

<Color filter>
Next, the color filter of the present invention will be described. The color filter of the present invention comprises a red filter segment, a green filter segment, and a blue filter segment, and the red filter segment therein contains the diketopyrrolopyrrole pigment composition of the present invention. Or it forms from the photosensitive coloring composition.

  The green filter segment can be formed using a conventional green coloring composition comprising a green pigment and a colorant carrier. Examples of the green pigment include C.I. I. Pigment Green 7, 10, 36, 37, 58, etc. are used.

  A yellow pigment can be used in combination with the green 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 containing a blue pigment and a colorant 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. 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 lightness.

<Color filter manufacturing method>
The color filter of the present invention can be produced 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 a solvent developing type or alkali developing type colored resist material is applied on a transparent substrate by spray coating, spin coating, slit coating, roll coating or the like. 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 coloring composition or the photosensitive coloring composition 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 Examples and Comparative Examples, “parts” and “%” mean “parts by mass” and “% by mass”.

<Mass ratio of diketopyrrolopyrrole pigment>
Diketopyrrolopyrrole pigment represented by formula (1), diketopyrrolopyrrole pigment represented by formula (2), and diketopyrrolopyrrole represented by formula (3) in the diketopyrrolopyrrole pigment composition The pigment content was quantified using HPLC. The measurement conditions are as follows.

Apparatus: Gulliver series detector manufactured by JASCO Corporation UV-970 detector manufactured by JASCO Corporation Column: Symmetry C18 manufactured by Waters (5 μm, 2.1 mmφ × 150 mm)
Mobile phase A solution: dimethylformamide / water (1: 1)
Mobile phase B: dimethylformamide / water (97.5: 2.5)
Gradient (Liquid B): 47% → (15min) → 47% → (5min) → 100% → (25min) → 100%
Wavelength: 510nm
Column temperature: 35 ° C
Flow rate: 0.3 mL / min
Sample injection volume: 5 μL (dissolved in N-methylpyrrolidone / 28% sodium methoxide methanol solution)

<X-ray diffraction of diketopyrrolopyrrole pigment>
The powder X-ray diffraction measurement of the diketopyrrolopyrrole pigment composition was carried out according to Japanese Industrial Standard JIS K0131 (general rules for X-ray diffraction analysis) in the range of diffraction angle (2θ) from 3 ° to 35 °. The measurement conditions are as follows.

Apparatus: RINT2100 manufactured by Rigaku Corporation
Sampling width: 0.02 °
Scan speed: 2.0
Divergence slit: 1 °
Divergence length restriction slit: 10 mm
Scattering slit: 2 °
Receiving slit: 0.3mm
Tube: Cu
Tube voltage: 30 kV
Tube current: 30 mA

<Mass average molecular weight (Mw) of binder resin>
The weight average molecular weight (Mw) of the binder resin is a polystyrene conversion measured by using TSKgel column (manufactured by Tosoh Corporation) and GPC equipped with RI detector (manufactured by Tosoh Corporation, HLC-8120GPC) using tetrahydrofuran as a developing solvent. The weight average molecular weight (Mw).

<Production method of diketopyrrolopyrrole pigment>
[Production Example 1] (Production of diketopyrrolopyrrole pigment represented by formula (1))
To a stainless steel reaction vessel equipped with a reflux tube, 200 parts of tert-amyl alcohol dehydrated with molecular sieves and 140 parts of sodium-tert-amyl alkoxide are added in a nitrogen atmosphere and heated to 100 ° C. with stirring to obtain an alcoholate solution. Prepared. 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 for 2 hours at 90 ° C. to obtain an alkali metal salt of a diketopyrrolopyrrole compound. 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 and rotating a shear disk having a diameter of 8 cm at 4000 rpm, the alkali metal salt of the diketopyrrolopyrrole compound 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 compound 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 obtain 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 compound aqueous paste obtained by filtering with an ultrafiltration machine is dried at 80 ° C. for 24 hours and pulverized, thereby diketopyrrolo represented by the formula (1). 150.8 parts of pyrrole pigment were obtained.

[Production Example 2] (Production of diketopyrrolopyrrole pigment represented by formula (2))
Except having changed 153.6 parts of 4-bromobenzonitrile into 117.4 parts of 4-chlorobenzonitrile, it carried out similarly to manufacture example 1, and the diketopyrrolopyrrole pigment 120.7 represented by Formula (2). Got a part.

[Production Example 3] (Production of diketopyrrolopyrrole pigment represented by formula (3-2))
While adding 220 parts of tert-amyl alcohol to the reaction vessel 1 and cooling with a water bath, 32 parts of 60% NaH was added and heated and stirred at 90 ° C. Next, 100 parts of tert-amyl alcohol, 85.0 parts of the compound of the following formula (17) synthesized by the method described in Example 1 of JP-A-2015-168725, and N-butyl-4-cyano were added to the reaction vessel 2. 68.7 parts of benzamide was dissolved by heating and added dropwise to the reaction vessel 1 over 2 hours. After reacting at 120 ° C. for 10 hours, cooling to 60 ° C., adding 400 parts of methanol and 50 parts of acetic acid, separating by filtration and washing with methanol, followed by diketopyrrolo represented by the formula (3-2) 93.2 parts of pyrrole pigment were obtained.

[Production Example 4] (Production of diketopyrrolopyrrole pigment represented by formula (3-5))
The same procedure as in Production Example 3 was carried out except that 68.7 parts of N-butyl-4-cyanobenzamide was changed to 75.5 parts of N-phenyl-4-cyanobenzamide and represented by formula (3-5). 97.6 parts of diketopyrrolopyrrole pigment were obtained.

[Production Example 5] (Production of diketopyrrolopyrrole pigment represented by formula (3-6))
The same procedure as in Production Example 3 was carried out except that 68.7 parts of N-butyl-4-cyanobenzamide was changed to 68.7 parts of N-butyl-3-cyanobenzamide and represented by formula (3-6). 93.2 parts of diketopyrrolopyrrole pigment were obtained.

[Production Example 6] (Production of diketopyrrolopyrrole pigment represented by formula (3-17))
The same procedure as in Production Example 3 was carried out except that 68.7 parts of N-butyl-4-cyanobenzamide was changed to 87.8 parts of N, N-dibutyl-4-cyanobenzamide, and represented by formula (3-17) 105.6 parts of the diketopyrrolopyrrole pigment obtained are obtained.

[Production Example 7] (Production of diketopyrrolopyrrole pigment represented by the following formula (18))
A diketopyrrolopyrrole pigment represented by the following formula (18) is prepared in the same manner as in Production Example 3 except that 68.7 parts of N-butyl-4-cyanobenzamide is changed to 60.9 parts of 4-cyanobiphenyl. 88.1 parts were obtained.

[Production Example 8] (Production of diketopyrrolopyrrole pigment represented by the following formula (19))
The diketopyrrolo represented by the formula (19) was prepared in the same manner as in Production Example 3 except that 68.7 parts of N-butyl-4-cyanobenzamide was changed to 84.1 parts of 4- (octylthio) benzonitrile. 103.2 parts of pyrrole pigment were obtained.

[Production Example 9] (Production of diketopyrrolopyrrole pigment represented by formula (3-12))
While adding 220 parts of tert-amyl alcohol to the reaction vessel 1 and cooling with a water bath, 32 parts of 60% NaH was added and heated and stirred at 90 ° C. Next, 100 parts of tert-amyl alcohol, 74.0 parts of the compound of the following formula (20) synthesized by the method described in Example 3 of JP-A-2015-168725, and N-butyl-4-cyano were added to the reaction vessel 2. 68.7 parts of benzamide was dissolved by heating and added dropwise to the reaction vessel 1 over 2 hours. After reacting at 120 ° C. for 10 hours, cooling to 60 ° C., adding 400 parts of methanol and 50 parts of acetic acid, followed by filtration and washing with methanol, diketopyrrolo represented by the formula (3-12) 85.6 parts of pyrrole pigment were obtained.

[Production Example 10] (Production of diketopyrrolopyrrole pigment represented by formula (3-8))
While adding 220 parts of tert-amyl alcohol to the reaction vessel 1 and cooling with a water bath, 32 parts of 60% NaH was added and heated and stirred at 90 ° C. Next, 100 parts of tert-amyl alcohol, 99.2 parts of the compound of the following formula (21) synthesized by the method described in Example 2 of JP-A-2015-168725, and N-butyl-4-cyano were added to the reaction vessel 2. 68.7 parts of benzamide was dissolved by heating and added dropwise to the reaction vessel 1 over 2 hours. After reacting at 120 ° C. for 10 hours, cooling to 60 ° C., adding 400 parts of methanol and 50 parts of acetic acid, followed by filtration and washing with methanol, the diketopyrrolo represented by the formula (3-8) 103.0 parts of pyrrole pigment were obtained.

[Production Example 11] (Production of diketopyrrolopyrrole pigment represented by formula (3-18))
The same procedure as in Production Example 10 was carried out except that 68.7 parts of N-butyl-4-cyanobenzamide was changed to 87.8 parts of N, N-dibutyl-4-cyanobenzamide, and represented by formula (3-18) Of diketopyrrolopyrrole pigment 115.4 parts.

[Production Example 12] (Production of diketopyrrolopyrrole pigment represented by the following formula (22))
Diketopyrrolopyrrole represented by the following formula (22) is carried out in the same manner as in Production Example 10 except that 68.7 parts of N-butyl-4-cyanobenzamide is changed to 46.8 parts of 4-chlorobenzonitrile. 115.4 parts of pigment were obtained.

[Production Example 13] (Production of diketopyrrolopyrrole pigment represented by formula (3-10))
While adding 220 parts of tert-amyl alcohol to the reaction vessel 1 and cooling with a water bath, 32 parts of 60% NaH was added and heated and stirred at 90 ° C. Next, 100 parts of tert-amyl alcohol, 82.0 parts of the compound of the following formula (23) synthesized by the method described in Example 7 of JP-A-2015-168725, and N-butyl-4-cyano were added to the reaction vessel 2. 68.7 parts of benzamide was dissolved by heating and added dropwise to the reaction vessel 1 over 2 hours. After reacting at 120 ° C. for 10 hours, cooling to 60 ° C., adding 400 parts of methanol and 50 parts of acetic acid, followed by filtration and washing with methanol, diketopyrrolo represented by the formula (3-10) 91.1 parts of pyrrole pigment were obtained.

[Production Example 14] (Production of diketopyrrolopyrrole pigment mixture (RC-1))
To a stainless steel reaction vessel equipped with a reflux tube, 200 parts of tert-amyl alcohol dehydrated with molecular sieves and 140 parts of sodium-tert-amyl alkoxide are added in a nitrogen atmosphere and heated to 100 ° C. with stirring to obtain an alcoholate solution. Prepared. Meanwhile, 88 parts of diisopropyl succinate, 104.5 parts of 4-chlorobenzonitrile and 19.3 parts of N, N-dibutyl-4-cyanobenzamide are added to a glass flask and heated to 90 ° C. with stirring. Dissolved to prepare solutions 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 for 2 hours at 90 ° C. to obtain an alkali metal salt of a diketopyrrolopyrrole compound. 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 and rotating a shear disk having a diameter of 8 cm at 4000 rpm, the alkali metal salt of the diketopyrrolopyrrole compound 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 compound 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 obtain 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 compound aqueous paste obtained by filtering off with an ultrafiltration machine was dried at 80 ° C. for 24 hours and pulverized to obtain a diketopyrrolopyrrole pigment mixture (RC-1). 143.6 parts were obtained. The content of the diketopyrrolopyrrole pigment represented by formula (2) and the diketopyrrolopyrrole pigment represented by formula (3-17) in the obtained diketopyrrolopyrrole pigment mixture was quantified using HPLC. As a result of analysis, the contents of the diketopyrrolopyrrole pigment represented by the formula (2) and the diketopyrrolopyrrole pigment represented by the formula (3-17) were 90.9% by mass and 9.1% by mass, respectively. Met.

[Production Example 15] (Production of diketopyrrolopyrrole pigment mixture (RC-2))
Except for changing 104.5 parts of 4-chlorobenzonitrile to 180.0 parts of 4-bromobenzonitrile, the same procedure as in Production Example 14 was carried out, and 176.6 parts of diketopyrrolopyrrole pigment mixture (RC-2) was added. Obtained. The content of the diketopyrrolopyrrole pigment represented by the formula (1) and the diketopyrrolopyrrole pigment represented by the formula (3-18) in the obtained diketopyrrolopyrrole pigment mixture was quantified using HPLC. As a result of analysis, the contents of the diketopyrrolopyrrole pigment represented by the formula (1) and the diketopyrrolopyrrole pigment represented by the formula (3-18) were 91.1% by mass and 8.9% by mass, respectively. Met.

<Method for producing binder resin solution>
[Production Example 16] (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, about 2 parts of the resin solution was sampled, heated and dried at 180 ° C. for 20 minutes, and the nonvolatile content was measured. The methoxypropyl acetate was added to the previously synthesized resin solution so that the nonvolatile content was 20 mass%. Was added to prepare an acrylic resin solution 1. The weight average molecular weight (Mw) was 26000.

[Production Example 17] (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 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% by mass. Thus, an acrylic resin solution 2 was prepared. The weight average molecular weight (Mw) was 18000.

<Method for producing diketopyrrolopyrrole pigment composition>
[Example 1] (Production of diketopyrrolopyrrole pigment composition (R-1))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (3-2), 1000 sodium chloride And 120 parts of diethylene glycol were charged into a stainless 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 10 hours. Next, the kneaded mixture is put into warm water, stirred for 1 hour while heating to about 80 ° C. to form a slurry, filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C. for one day and pulverized. As a result, 97.0 parts of a diketopyrrolopyrrole pigment composition (R-1) was obtained.

[Example 2] (Production of diketopyrrolopyrrole pigment composition (R-2))
The diketopyrrolopyrrole pigment of the formula (3-2) was prepared in the same manner as in Example 1 except that 5.0 parts of the diketopyrrolopyrrole pigment of the formula (3-5) was changed to 5.0 parts. 96.8 parts of pyrrolopyrrole pigment composition (R-2) were obtained.

[Example 3] (Production of diketopyrrolopyrrole pigment composition (R-3))
The diketopyrrolopyrrole pigment of the formula (3-2) was prepared in the same manner as in Example 1 except that 5.0 parts of the diketopyrrolopyrrole pigment of the formula (3-6) was changed to 5.0 parts. 97.8 parts of pyrrolopyrrole pigment composition (R-3) were obtained.

[Example 4] (Production of diketopyrrolopyrrole pigment composition (R-4))
The same procedure as in Example 1 was conducted except that 5.0 parts of the diketopyrrolopyrrole pigment of formula (3-2) was changed to 5.0 parts of the diketopyrrolopyrrole pigment of formula (3-17). 97.2 parts of pyrrolopyrrole pigment composition (R-4) were obtained.

[Example 5] (Production of diketopyrrolopyrrole pigment composition (R-5))
The diketopyrrolopyrrole pigment of the formula (3-2) was prepared in the same manner as in Example 1 except that 5.0 parts of the diketopyrrolopyrrole pigment of the formula (3-12) was changed to 5.0 parts. 97.1 parts of pyrrolopyrrole pigment composition (R-5) were obtained.

[Example 6] (Production of diketopyrrolopyrrole pigment composition (R-6))
The same procedure as in Example 1 was carried out except that 5.0 parts of the diketopyrrolopyrrole pigment of formula (3-2) was changed to 5.0 parts of the diketopyrrolopyrrole pigment of formula (3-8). 96.2 parts of pyrrolopyrrole pigment composition (R-6) were obtained.

[Example 7] (Production of diketopyrrolopyrrole pigment composition (R-7))
The same procedure as in Example 1 was carried out except that 5.0 parts of the diketopyrrolopyrrole pigment of formula (3-2) was changed to 5.0 parts of the diketopyrrolopyrrole pigment of formula (3-10). 96.9 parts of pyrrolopyrrole pigment composition (R-7) were obtained.

[Example 8] (Production of diketopyrrolopyrrole pigment composition (R-8))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (3-2) 1) diketopyrrolopyrrole pigment 66.5 parts, diketopyrrolopyrrole pigment 28.5 parts of formula (2), diketopyrrolopyrrole pigment 5.0 parts of formula (3-17) It carried out like Example 1 and obtained 98.2 parts of diketopyrrolopyrrole pigment compositions (R-8).

[Example 9] (Production of diketopyrrolopyrrole pigment composition (R-9))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (3-2) 1) diketopyrrolopyrrole pigment 28.5 parts, diketopyrrolopyrrole pigment 66.5 parts of formula (2), diketopyrrolopyrrole pigment 5.0 parts of formula (3-17) In the same manner as in Example 1, 98.0 parts of a diketopyrrolopyrrole pigment composition (R-9) was obtained.

[Example 10] (Production of diketopyrrolopyrrole pigment composition (R-10))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (3-2) 1) diketopyrrolopyrrole pigment 1) of 1), 76.0 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (3-17), In the same manner as in Example 1, 97.8 parts of a diketopyrrolopyrrole pigment composition (R-10) was obtained.

[Example 11] (Production of diketopyrrolopyrrole pigment composition (R-11))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (3-2) Except for the change to 19.5 diketopyrrolopyrrole pigment of 1), 49.5 parts of diketopyrrolopyrrole pigment of formula (2), and 1.0 part of diketopyrrolopyrrole pigment of formula (3-2), It carried out like Example 1 and obtained 97.5 parts of diketopyrrolopyrrole pigment compositions (R-11).

[Example 12] (Production of diketopyrrolopyrrole pigment composition (R-12))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (3-2) Except for the change to 15.0 diketopyrrolopyrrole pigment of 1), 45.0 parts of diketopyrrolopyrrole pigment of formula (2), and 10.0 parts of diketopyrrolopyrrole pigment of formula (3-2), In the same manner as in Example 1, 97.3 parts of a diketopyrrolopyrrole pigment composition (R-12) was obtained.

[Example 13] (Production of diketopyrrolopyrrole pigment composition (R-13))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (3-2) 12.5 diketopyrrolopyrrole pigment of formula (2), 42.5 parts of diketopyrrolopyrrole pigment of formula (2), 15.0 parts of diketopyrrolopyrrole pigment of formula (3-2), It carried out like Example 1 and obtained 98.1 parts of diketopyrrolopyrrole pigment compositions (R-13).

[Example 14] (Production of diketopyrrolopyrrole pigment composition (R-14))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (3-2) Except for the change to 10.0 diketopyrrolopyrrole pigment of 1), 40.0 parts of diketopyrrolopyrrole pigment of formula (2), 20.0 parts of diketopyrrolopyrrole pigment of formula (3-2), In the same manner as in Example 1, 97.0 parts of a diketopyrrolopyrrole pigment composition (R-14) was obtained.

[Example 15] (Production of diketopyrrolopyrrole pigment composition (R-15))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (3-2) 1) diketopyrrolopyrrole pigment 69.5 parts, diketopyrrolopyrrole pigment 29.5 parts of formula (2), diketopyrrolopyrrole pigment 1.0 parts of formula (3-2) In the same manner as in Example 1, 97.8 parts of a diketopyrrolopyrrole pigment composition (R-15) was obtained.

[Example 16] (Production of diketopyrrolopyrrole pigment composition (R-16))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (3-2) 1) diketopyrrolopyrrole pigment 59.5 parts, diketopyrrolopyrrole pigment 25.5 parts of formula (2), diketopyrrolopyrrole pigment 15.0 parts of formula (3-2) In the same manner as in Example 1, 96.9 parts of a diketopyrrolopyrrole pigment composition (R-16) was obtained.

[Example 17] (Production of diketopyrrolopyrrole pigment composition (R-17))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (3-2) 19.5 parts of diketopyrrolopyrrole pigment of 1), 79.5 parts of diketopyrrolopyrrole pigment of formula (2), and 1.0 part of diketopyrrolopyrrole pigment of formula (3-2), In the same manner as in Example 1, 97.4 parts of a diketopyrrolopyrrole pigment composition (R-17) was obtained.

[Example 18] (Production of diketopyrrolopyrrole pigment composition (R-18))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (3-2) 17.0 parts of diketopyrrolopyrrole pigment of 1), 68.0 parts of diketopyrrolopyrrole pigment of formula (2), 15.0 parts of diketopyrrolopyrrole pigment of formula (3-2), In the same manner as in Example 1, 96.4 parts of diketopyrrolopyrrole pigment composition (R-18) was obtained.

[Example 19] (Production of diketopyrrolopyrrole pigment composition (R-19))
42.7 parts of diketopyrrolopyrrole pigment of formula (1), 42.7 parts of diketopyrrolopyrrole pigment of formula (2), 4.5 parts of diketopyrrolopyrrole pigment of formula (3-2), formula (8 -1) 10.0 parts of a benzoisoindole derivative, 1000 parts of sodium chloride, and 120 parts of diethylene glycol were charged into a 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 10 hours. Next, the kneaded mixture is put into warm water, stirred for 1 hour while heating to about 80 ° C. to form a slurry, filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C. for one day and pulverized. As a result, 97.1 parts of diketopyrrolopyrrole pigment composition (R-19) was obtained.

[Example 20] (Production of diketopyrrolopyrrole pigment composition (R-20))
Diketopyrrolopyrrole was carried out in the same manner as in Example 19 except that 10.0 parts of the benzoisoindole derivative of the formula (8-1) was changed to 10.0 parts of the thiazineindigo derivative of the formula (11-6). 97.7 parts of pigment composition (R-20) were obtained.

[Example 21] (Production of diketopyrrolopyrrole pigment composition (R-21))
Diketopyrrolo was prepared in the same manner as in Example 19 except that 10.0 parts of the benzoisoindole derivative of the formula (8-1) was changed to 10.0 parts of the diketopyrrolopyrrole derivative of the formula (7-6). 98.2 parts of pyrrole pigment composition (R-21) were obtained.

[Example 22] (Production of diketopyrrolopyrrole pigment composition (R-22))
A diketopyrrolopyrrole pigment composition was prepared in the same manner as in Example 19 except that 10.0 parts of the benzoisoindole derivative of the formula (8-1) was changed to 10.0 parts of the quinophthalone derivative of the formula (15-1). 97.5 parts of product (R-22) was obtained.

[Example 23] (Production of diketopyrrolopyrrole pigment composition (R-23))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 52.5 parts of diketopyrrolopyrrole pigment mixture (RC-1), 1000 parts of sodium chloride, and 120 parts of diethylene glycol were added to a 1 gallon kneader made of stainless steel (Inoue Seisakusho). Manufactured) and kneaded at 60 ° C. for 10 hours. Next, the kneaded mixture is put into warm water, stirred for 1 hour while heating to about 80 ° C. to form a slurry, filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C. for one day and pulverized. As a result, 97.9 parts of a diketopyrrolopyrrole pigment composition (R-23) was obtained.

[Example 24] (Production of diketopyrrolopyrrole pigment composition (R-24))
47.5 parts of diketopyrrolopyrrole pigment of formula (1) and 52.5 parts of diketopyrrolopyrrole pigment mixture (RC-1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), diketopyrrolo Except having changed to 52.5 parts of pyrrole pigment mixtures (RC-2), it carried out like Example 23 and obtained 97.0 parts of diketopyrrolopyrrole pigment compositions (R-24).

[Example 25] (Production of diketopyrrolopyrrole pigment composition (R-25))
In a stainless steel container, 275.0 parts of an alkali metal salt solution of a diketopyrrolopyrrole compound prepared by the method described in Production Example 1, and an alkali metal salt of a diketopyrrolopyrrole compound prepared by the method described in Production Example 14 303.0 parts of the solution was added, and the mixture was stirred and mixed at 75 ° C. for 30 minutes to obtain a mixed solution of diketopyrrolopyrrole compound alkali metal salt. 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. Using a high-speed stirring disperser, rotate the shear disk having a diameter of 8 cm at 4000 rpm, and add a small amount of the alkali metal salt mixed solution of the diketopyrrolopyrrole compound obtained above. Added in increments. At this time, the rate of addition of the alkali metal salt of the diketopyrrolopyrrole compound 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 obtain 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 compound aqueous paste obtained by filtering off with an ultrafiltration machine was dried at 80 ° C. for 24 hours and pulverized to thereby obtain a diketopyrrolopyrrole pigment composition (R-25). ) 150.3 parts were obtained.

[Example 26] (Production of diketopyrrolopyrrole pigment composition (R-26))
A stainless steel container was charged with 1000 parts of tert-amyl alcohol in which 150 parts of a 28% sodium methoxide methanol solution was dissolved, 47.5 parts of a diketopyrrolopyrrole pigment of formula (1), and a diketo of formula (2). 47.5 parts of pyrrolopyrrole pigment and 5.0 parts of diketopyrrolopyrrole pigment of formula (3-17) were added and stirred for 2 hours. Thereafter, a solution of the diketopyrrolopyrrole pigment composition was added little by little while stirring 10,000 parts of water. The obtained diketopyrrolopyrrole pigment composition suspension was filtered, washed with water, dried overnight at 80 ° C., and pulverized to obtain 95.5 parts of a diketopyrrolopyrrole pigment composition (R-26). .

[Comparative Example 1] (Production of diketopyrrolopyrrole pigment composition (R-27))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (3-2) Except having changed into 100.0 parts of 1) diketopyrrolopyrrole pigment of 1), it carried out like Example 1 and obtained 98.4 parts of diketopyrrolopyrrole pigment (R-27).

[Comparative Example 2] (Production of diketopyrrolopyrrole pigment composition (R-28))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (3-2) Except having changed to 100.0 parts of diketopyrrolopyrrole pigments of 2), it carried out like Example 1 and obtained 98.6 parts of diketopyrrolopyrrole pigments (R-28).

[Comparative Example 3] (Production of diketopyrrolopyrrole pigment composition (R-29))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (3-2) A diketopyrrolopyrrole pigment composition was prepared in the same manner as in Example 1 except that 95.0 parts of the diketopyrrolopyrrole pigment of 1) and 5.0 parts of the diketopyrrolopyrrole pigment of the formula (3-2) were changed. 97.8 parts of (R-29) was obtained.

[Comparative Example 4] (Production of diketopyrrolopyrrole pigment composition (R-30))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (3-2) The same diketopyrrolopyrrole pigment composition as in Example 1 except that 95.0 parts of the diketopyrrolopyrrole pigment of 2) and 5.0 parts of the diketopyrrolopyrrole pigment of the formula (3-2) were changed. 98.1 parts of (R-30) was obtained.

[Comparative Example 5] (Production of diketopyrrolopyrrole pigment composition (R-31))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (3-2) Example 1 except that 50.0 parts of diketopyrrolopyrrole pigment of 1), 45.0 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (18) 1 and 97.3 parts of diketopyrrolopyrrole pigment composition (R-31) was obtained.

[Comparative Example 6] (Production of diketopyrrolopyrrole pigment composition (R-32))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (3-2) Example 1 except that 50.0 parts of diketopyrrolopyrrole pigment of 1), 45.0 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (19) 1 and 97.6 parts of diketopyrrolopyrrole pigment composition (R-32) was obtained.

[Comparative Example 7] (Production of diketopyrrolopyrrole pigment composition (R-33))
Except for changing 47.5 parts of the diketopyrrolopyrrole pigment of the formula (1) and 47.5 parts of the diketopyrrolopyrrole pigment of the formula (2) to 95.0 parts of the diketopyrrolopyrrole pigment of the formula (22) In the same manner as in Example 1, 95.9 parts of a diketopyrrolopyrrole pigment composition (R-33) was obtained.

[Comparative Example 8] (Production of diketopyrrolopyrrole pigment composition (R-34))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (3-2) 10.0 parts of diketopyrrolopyrrole pigment of 1), 18.0 parts of diketopyrrolopyrrole pigment of formula (2), 2.0 parts of diketopyrrolopyrrole pigment of formula (3-17), In the same manner as in Example 1, 97.2 parts of a diketopyrrolopyrrole pigment composition (R-34) was obtained.

[Comparative Example 9] (Production of diketopyrrolopyrrole pigment composition (R-35))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (3-2) 1) diketopyrrolopyrrole pigment 10.0 parts, diketopyrrolopyrrole pigment 88.0 parts of formula (2), diketopyrrolopyrrole pigment 2.0 parts of formula (3-17) In the same manner as in Example 1, 97.9 parts of a diketopyrrolopyrrole pigment composition (R-35) was obtained.

[Comparative Example 10] (Production of diketopyrrolopyrrole pigment composition (R-36))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), 5.0 parts of diketopyrrolopyrrole pigment of formula (3-2) A diketopyrrolopyrrole pigment composition (R) was prepared in the same manner as in Example 1 except that 50.0 parts of the diketopyrrolopyrrole pigment of 1) and 50.0 parts of the diketopyrrolopyrrole pigment of the formula (2) were changed. -36) 98.8 parts were obtained.

[Comparative Example 11] (Production of diketopyrrolopyrrole pigment composition (R-37))
47.5 parts of diketopyrrolopyrrole pigment of formula (1), 47.5 parts of diketopyrrolopyrrole pigment of formula (2), and 5.0 parts of diketopyrrolopyrrole pigment of formula (3-2) are stirred at high speed. By stirring and mixing with a disper, 99.9 parts of a diketopyrrolopyrrole pigment composition (R-37) was obtained.

  The contents of the produced diketopyrrolopyrrole pigment compositions 1 to 37 are shown in Table 1.

<Method for producing colored composition for color filter>
[Example 27] (Preparation of colored composition (RP-1))
The following mixture was stirred and mixed to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) using zirconia beads having a diameter of 0.5 mm, and then a 5 μm filter. To prepare a colored composition (RP-1).
Diketopyrrolopyrrole pigment composition (R-1) 11.0 parts Dye derivative Formula (15-1) 1.0 part Acrylic resin solution 1 40.0 parts Propylene glycol monomethyl ether acetate 48.0 parts

[Examples 28 to 52] (Coloring composition (RP-2 to 26))
A color composition was carried out in the same manner as in Example 27 except that the diketopyrrolopyrrole pigment composition (R-1) was changed to the diketopyrrolopyrrole pigment composition (R-2 to 26) shown in Table 2. A product (RP-2 to 26) was obtained.

[Comparative Examples 12 to 22] (Coloring composition (RP-27 to 37))
A coloring composition was obtained in the same manner as in Example 27 except that the diketopyrrolopyrrole pigment composition (R-1) was changed to the diketopyrrolopyrrole pigment composition (R-27 to 37) shown in Table 2. A product (RP-27 to 37) was obtained.

<Evaluation of coloring composition for color filter>
The following evaluation was performed about the obtained coloring composition (RP-1 to 37). The evaluation results are shown in Table 2.

(Evaluation of contrast ratio of coating film)
The obtained colored composition was applied onto a glass substrate having a size of 100 mm × 100 mm and a thickness of 0.7 mm so that x = 0.640 was obtained with a C light source and dried. Furthermore, the red coating film was obtained by heating at 230 degreeC for 60 minutes. About the obtained red coating film, the contrast was measured by the following method.

A method for measuring the contrast ratio of the coating film will be described. The light emitted from the backlight unit for liquid crystal display passes through the polarizing plate, is polarized, passes through the dried coating film of the colored composition applied on the glass substrate, and reaches the polarizing plate. If the polarizing planes of the polarizing plate and the polarizing plate are parallel, light is transmitted through the polarizing plate, but if the polarizing plane is perpendicular, the light is blocked by the polarizing plate. However, when the light polarized by the polarizing plate passes through the dried coating film of the colored composition, scattering by the pigment particles occurs, resulting in deviation in a part of the polarization plane. When the amount of light transmitted through the plate is reduced and the polarizing plate is perpendicular, a part of the light is transmitted through the polarizing plate. This transmitted light was measured as the luminance on the polarizing plate, and the ratio (contrast ratio) between the luminance when the polarizing plate was parallel and the luminance when it was orthogonal was calculated.
(Contrast ratio) = (Luminance when parallel) / (Luminance when direct)
Accordingly, when scattering occurs due to the pigment in the coating film, the brightness when parallel is reduced and the brightness when perpendicular is increased, the contrast ratio is lowered. A color luminance meter ("BM-5A" manufactured by Topcon Corporation) was used as the luminance meter, and a polarizing plate ("NPF-G1220DUN" manufactured by Nitto Denko Corporation) was used as the polarizing plate. In the measurement, a black mask with a 1 cm square hole was applied to the measurement portion in order to block unnecessary light.

(Evaluation of initial viscosity)
The viscosity of the colored composition was measured at 25 ° C. using an E-type viscometer (“ELD viscometer” manufactured by Toki Sangyo Co., Ltd.) on the day of adjusting the colored composition.
○: Initial viscosity is 50 mPa · s or less Δ: Initial viscosity is 50 or more and less than 150 mPa · s ×: Initial viscosity is 150 mPa · s or more

(Evaluation of stability over time)
For samples that were allowed to stand at 40 ° C. for 7 days from the day of preparation of the coloring composition, after returning the sample temperature to 25 ° C., the viscosity with time was measured according to the above viscosity measurement method, and the rate of increase with time was determined from the following formula. It was.
Thickening ratio with time = (viscosity with time) / (initial viscosity) x 100 (%)
The viscosity stability was evaluated based on the viscosity increase rate with time. If the thickening ratio with time is 80% or more and less than 120%, it can be practically endured. When the viscosity is reduced or increased beyond this range, when the colored composition is coated on the glass substrate, it cannot be applied under the same coating conditions, resulting in a problem in productivity. . More preferably, it is 90% or more and less than 110%.
○: Thickening rate over time 90% or more and less than 110% Δ: Thickening rate over time 80% or more and less than 90%, or 110% or more and less than 120% ×: Thickening rate over time or less than 80% or 120% or more

<Method for producing other colored composition>
(Preparation of colored composition (RP-38))
The mixture of the composition shown below is stirred and mixed uniformly, dispersed with picomil for 8 hours using zirconia beads having a diameter of 0.1 mm, and then filtered through a 5 μm filter to prepare a colored composition (RP-38). did.
Dianthraquinone pigment (PR177-1) 10.8 parts Dye derivative represented by formula (9-5) 1.2 parts Acrylic resin solution 1 40.0 parts Propylene glycol monomethyl ether acetate 48.0 parts

<Production method of photosensitive coloring composition>
[Example 53] (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 photosensitive coloring composition 1 (RR-1).
Colored composition (RP-1) 38.4 parts Colored composition (RP-38) 3.6 parts Acrylic resin solution 2 13.2 parts Photopolymerizable monomer ("Aronix M400" manufactured by Toagosei Co., Ltd.) 8 parts Photopolymerization initiator ("Irgacure 907" manufactured by BASF) 2.0 parts Sensitizer ("EAB-F" manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts 39.6 parts of ethylene glycol monomethyl ether acetate

[Examples 54 to 78] (Preparation of photosensitive coloring composition (RR-2 to 26))
The colored composition (RP-1) is changed to the colored composition (RP-2 to 26), and further the colored composition (RP-2 to 25) and the colored composition so as to have the same chromaticity as Example 53 A photosensitive coloring composition (RR-2 to 26) was produced in the same manner as in Example 53 except that the ratio of (RP-38) was adjusted.

[Comparative Examples 23 to 33] (Preparation of photosensitive coloring composition (RR-27 to 37))
The colored composition (RP-1) is changed to the colored composition (RP-27 to 37), and the colored composition (RP-27 to 37) and the colored composition so as to have the same chromaticity as Example 53 are obtained. A photosensitive coloring composition (RR-27 to 37) was produced in the same manner as in Example 53 except that the ratio of (RP-38) was adjusted.

<Evaluation of photosensitive coloring composition>
The following evaluation was performed about the obtained photosensitive coloring composition (RR-1 to 37). The evaluation results are shown in Table 3.

(Color characteristic 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 = 0.328 in a C light source, and dried. 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. Then, the brightness (Y) of the obtained coating film was measured with a microspectrophotometer (“OSP-SP200” manufactured by Olympus Optical Co., Ltd.).

(Evaluation of crystal precipitation on the coating film surface)
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 = 0.328 in a C light source, and dried. Then, ultraviolet rays of 300 mJ / cm ² were irradiated using an ultra high pressure mercury lamp. Subsequently, after heat treatment at 230 ° C. for 60 minutes, the heat treatment at 240 ° C. for 60 minutes was repeated twice. The coating film surface of the substrate after the heat treatment was observed with an optical microscope, and the presence or absence of crystal precipitation was determined according to the following criteria.
A: After heat treatment at 230 ° C. for 60 minutes, after further heat treatment at 240 ° C. for 60 minutes, and further at 240 ° C. for 60 minutes, no crystal precipitation ○: After heat treatment at 230 ° C. for 60 minutes and further at 240 ° C. for 60 minutes There is no crystal precipitation, but there is crystal precipitation in the second heat treatment at 240 ° C. for 60 minutes. Δ: There is no crystal precipitation in the heat treatment at 230 ° C. for 60 minutes. Crystal precipitation after heat treatment for 1 minute

  From the results of Table 3, in color filter formation, the diketopyrrolopyrrole pigment represented by the formula (1), the diketopyrrolopyrrole pigment represented by the formula (2), and the general formula (3) in the present invention. In the diketopyrrolopyrrole pigment composition containing the diketopyrrolopyrrole pigment, the mass ratio of the diketopyrrolopyrrole pigment represented by formula (1) and the diketopyrrolopyrrole pigment represented by formula (2) is Diketopyrrolopyrrole pigment composition that is 70: 30-20: 80 and does not have a maximum peak in the range of diffraction angle (2θ) = 5-12 ° in powder X-ray diffraction measurement using CuKα ray The examples using the color were excellent in brightness and contrast ratio, and were able to suppress the crystal precipitation of the pigment due to the heating process.

<Color filter manufacturing method>
[Production Example 18] (Preparation of green photosensitive coloring composition 1 (GR-1))
A mixture having the composition shown below is 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 a 5 μm filter. To produce a green colored composition 1 (GP-1).
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

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 green photosensitive coloring composition 1 (GR-1).
Green coloring composition 1 (GP-1) 42.0 parts Acrylic resin solution 2 13.2 parts Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 2.8 parts Photopolymerization initiator (manufactured by BASF) "Irgacure 907") 2.0 parts Sensitizer ("EAB-F" manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts Ethylene glycol monomethyl ether acetate 39.6 parts

[Production Example 19] (Preparation of blue photosensitive coloring composition 1 (BR-1))
A mixture having the composition shown below is 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 a 5 μm filter. And blue colored composition 1 (BP-1) was produced.
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 part Acrylic Resin Solution 1 35.0 parts Propylene glycol monomethyl ether acetate 52.0 parts

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 (BP-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 (manufactured by BASF) "Irgacure 907") 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 is patterned on a glass substrate, and the photosensitive coloring composition (RR-8) of the present invention is formed on the substrate with a spin coater so that x = 0.640 and y = 0.328. It was applied to form a colored film. The film was irradiated with ultraviolet rays of 300 mJ / cm ² 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 sodium carbonate aqueous solution to remove the unexposed portion, and the substrate was washed with ion-exchanged water, and the substrate was heated at 230 ° C. for 20 minutes to obtain a red filter. A segment was formed. In the same manner, the green photosensitive coloring composition 1 (GR-1) was formed to a thickness such that x = 0.300 and y = 0.600, and the blue photosensitive coloring composition 1 (BR-1) was added. The film was applied to a thickness of x = 0.150 and y = 0.060, respectively, to form a green filter segment and a blue filter segment to obtain a color filter.

  By using the photosensitive coloring composition (RR-8) of the present invention, it was possible to produce a color filter having excellent brightness and contrast and having no pigment crystal precipitation in the heating step.

Claims (6)

A diketopyrrolopyrrole pigment represented by formula (1), a diketopyrrolopyrrole pigment represented by formula (2), and a diketopyrrolopyrrole pigment represented by formula (3) A pigment composition, wherein the mass ratio of the diketopyrrolopyrrole pigment represented by formula (1) and the diketopyrrolopyrrole pigment represented by formula (2) is 70:30 to 20:80, and A diketopyrrolopyrrole pigment composition having no maximum peak in the range of diffraction angle (2θ) = 5 to 12 ° in powder X-ray diffraction using CuKα rays.

[In General Formula (3), R ¹ is a hydrogen atom, a halogen atom or a cyano group, and R ² and R ³ are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or a substituent. It may be a phenyl group. ]   The diketopyrrolopyrrole according to claim 1, wherein a mass ratio of the diketopyrrolopyrrole pigment represented by the formula (1) and the diketopyrrolopyrrole pigment represented by the formula (2) is 50:50 to 20:80. A pyrrole pigment composition.   The diketopyrrolopyrrole pigment content represented by the general formula (3) is 1% by mass to 15% by mass with respect to the total amount of the diketopyrrolopyrrole pigment composition. Ketopyrrolopyrrole pigment composition.   The coloring composition for color filters containing the diketopyrrolopyrrole pigment composition as described in any one of Claims 1-3, binder resin, and the organic solvent.   Furthermore, the coloring composition for color filters of Claim 4 containing at least 1 type 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 of Claim 4 or 5.